In this episode of Startups For The Rest Of Us, Rob and Mike talk about bootstrapping versus funding. It is a common question new entrepreneurs ask themselves and based on an article on the subject, the guys comment and elaborate on some of these questions.
Items mentioned in this episode:
Rob: In this episode of Startups For The Rest Of Us, Mike and I talk about 19 questions to ask when considering bootstrapping versus raising funding. This is Startups For The Rest Of Us episode 411.
Welcome to Startups For The Rest Of Us. The podcast that helps developers, designers, and entrepreneurs be awesome at building, launching, and growing software products whether you’ve built your first product or you’re just thinking about it. I’m Rob.
Mike: And I’m Mike.
Rob: We’re here to share our experiences to help you avoid the same mistakes we’ve made. Where this week, sir?
Mike: Well, there is a book recommendation that you’ve given awhile ago called, The Hard Thing About Hard Things. I’ve commented it, I’ve bought the book, but I haven’t read it yet. I’ve been kind of diving into that a little bit. I find it fascinating probably more so from a historical perspective because Ben Horowitz, who’s the author, he’s talking about his journey through the startup after he had left PayPal, and running this other company, and they basically only had one customer that was providing 90% of the revenue and basically spun that business off into its own separate entity and got rid of a bunch of assets with it, and talks about he built up the company from there.
What I find fascinating about it is that the new company is called Opsware. I remember back in those days when I was doing sales demos and presentations and stuff, I was actually in some cases, competing against Opsware.
Rob: That’s a trip. That book–it is brutal. Have you finished it?
Mike: I’ve not, no.
Rob: I was so stressed. It’s a good book but I don’t know if I could listen to it again because what he has to go through to grow and keep his company from basically going under and then he sells it for $1 billion or multiple billions of dollars and then he starts Andreessen Horowitz—that part is not in the book but he talks a little bit about it—but he is the Horowitz of Andreessen Horowitz. I remember listening to it and being like, “Yup, I could not have done this. I would have imploded.” It is, The Hard Thing About Hard Things is a good title for it.
Mike: Yeah, definitely. I do not think that I would have wanted to go through all the stuff that he’s gone through especially just the financial challenge of trying to go public at the time that he did, right after the economy kind of cratered. What did he say? Like there was 200 plus IPOs the year before and then there was 6 or 12 or something like that the year that he did it. Wow!
Rob: It’s crazy. He went public, he didn’t get acquired, I forgot what…
Mike: No, he went public first and it was in a bad environment. The reason they went public was because they couldn’t get anymore investment capital from investors. Then it was a bunch of years later, like 2007 or something like that where they ended up selling to HP for, I think, it was $1 or $2 billion.
Rob: Got it. That was my memory, but I have forgotten they went public. It’s agonizing. It really is the shoot for the $1 billion exit. You don’t need to be a several hundred-million-dollar revenue journey raising venture capital and all that stuff. A lot of it just did not sound like something I ever want to experience in my life, even for payout like that. I don’t it’d be worth it.
Mike: How about you? What’s going on this week?
Rob: Well, you and I just had a conversation before this episode started recording. We are evaluating potentially having sponsorships on Startups For The Rest Of Us. If you are a company, whether you’re a startup or if you think that you would be interested in reaching the Startups For The Rest Of Us audience—it’s a lot of bootstrappers but it’s also a lot of people running six and seven figure businesses, drop us a line at questionsforstartupsfortherestofus.com and just put “Sponsor” or “Sponsorship” in the subject line, and we’ll talk about it.
Obviously, as a listener, we’re been doing this for eight years, and we appreciate the trust that you put in Mike and I to produce high-quality content and to deliver value to you. We have no intention of “screwing up” the podcast by adding a bunch of sponsorship roles in the thing and interrupting your flow, but we are at a point where it does cost us money and it does cost us time away from our businesses to do this, so we’re just evaluating it. It’s a preliminary thing, we definitely have not made up our mind about it, but we do want to explore this as an option.
Mike: Again, that email address is questionsforstartupsfortherestofus.com and just put “Sponsorship” or “Sponsor” in the subject line, and we’ll take a look at it. Again, we’ll just kind of evaluate how things go. To reiterate what Rob had said, we appreciate you guys listening and we don’t want to screw up the whole thing. I think like a lot of things that we’ve done at MicroConf every year I think is just kind of a play it safe approach, but at the same time, look for ways to change things to make things better.
Rob: Yeah, we’ve experimented a lot with things at MicroConf over the years. Some have worked, some haven’t. But one thing that I think we’ve done a good job is recognizing when they work and don’t and basically changing it up when things don’t. Even if we try it, if it suddenly becomes a […] or something like that, I could imagine pivoting.
Today, we’re going to be running through an article by a listener and commenter name Don Gooding. The title of his article is Bootstrapping versus Venture Capital: 19 Questions to Ask. But what I find interesting about the article is it’s not just about venture capital, it is about angel investment as well. But before we get there, we have a comment from Adam on episode 406, and 406 was five episodes ago when you and I discussed, “Should bootstrappers raise money?” was the title of the episode. Adam said, “I’m so glad you jumped in, Mike, and said something about Rob hitting 21k MRR saying that it wasn’t a fair comparison.” Because I believe I was saying, “Drip hit 21k MRR quickly and if it took me four years to get there then I would’ve […] it down.” And you said, “Well, that’s not a fair comparison because you’re in a different place and if you’re building something on the side, maybe it is four years.”–to that point.
Back to Adam. He says, “I’m still trying to hit 21k MRR after four year, but I don’t think I’m failing at what I’m doing. Maybe an episode on what you think that growth is, that people should be aiming for, this was a good episode. A follow-up question to Mike would be, why have you or have you not fun strapped Bluetick?”
Mike: Oh, that’s a good question that I don’t have a good answer for.
Rob: It’s something evaluated, no?
Mike: Oh, yeah. I’ve looked at it a couple of times. I had a few conversations privately with people I know who have raised money, and just asked them what their take on it was, what their experiences was after going through it, what were the drawbacks, what would they have done differently. I got a sense that it was going to be rather complicated and time-consuming, and I didn’t have the time to spend on it. I continue to kind of look at it and continue to think about but it’s not something where I’ve said, “Yeah, I definitely want to do that. I’m all in. I’m going to dedicate the next X weeks or months whatever going out and raising funding.”
I’ve probably spent a lot more time working on getting Bluetick to a better place. I think I have been open about the fact that early on, I had hired a bunch of contractors to build a lot of the core infrastructure of Bluetick. Quite frankly, it was not done very well so there’s a lot of things that are generally screwed up and it makes it difficult to make changes. I would prefer to move fast if I can help it, but the problem is a lot of the architecture and the choices that were made at the time make that difficult. I have a hard time pulling away from those things and doing some of the clean-up work to basically make myself be able to move faster.
Because I feel like if I had like a pile of money, I would feel obligated to expand things a lot quicker and maybe even more than I’m possibly comfortable with, and I just know that there are certain parts of the app that if I were to dump 50 or 100 users on it all at once, it’s not going to scale very well. There are certain processes that need to run and it’s just not going to take a large influx of people very well. It can do it, I’d probably have to tweak a couple of settings to make it happen, but I’m not real comfortable doing that. I think it’s partly out of obligation, partly out of complexity and the time that I would have to spend on it.
Rob: You have technical debt already.
Mike: Yes. I think you have technical debt as soon as you write a single line of code.
Rob: Well, not if it’s fully unit tested, though. I think of […] there’s that, I don’t if it’s a joke or it if it’s truly the definition but it’s like, “Legacy code is code that is not highly unit tested.” Yeah, you have a little bit of technical debt but to hear that it’s hard to make changes, that’s a real bummer to hear given how early stage you are, and that you’re a technical founder. That’s the whole point of us being technical founders, that’s our skill set, we shouldn’t have that.
Mike: Maybe I should caveat that a little bit more. It’s not that it’s hard to make changes, it’s that I feel uncomfortable making changes to certain places because they’re not as well unit tested as I would like them to be. The software does a lot. There’s some changes I’ll just push out. It’s just like, “Hey, this is a frontend UI changes, it’s not that big of a deal.” But then when you get into things like, how mailboxes are stored and how the data is synchronized, I’m real hesitant to make changes to those because there is, in one particular case I can think off the top of my head, there was literally no way for me to unit test it whatsoever.
It’s hard to justify going in there and just making whole scale changes that would make things easier because I know that it’s working and if it breaks, it does a lot of work every second, and things could go seriously sideways very, very quickly. The new build server I put in place a couple of weeks ago would actually make rolling back pretty easy, but then I’d have to go through and figure out what in the code broke. Again, it’s not easy to unit tested that piece.
Rob: Yeah, I feel like, “Next time, should we just build, I don’t know, simple project management that just pulls things out of databases. It’s that no connections to any external sources and no queues. I don’t want any queues, I want everything synchronize.
Mike: Honestly, that’s part of it is the queues and stuff that I have to deal with. Queues processing, storing data, being able to filter certain things out and, “Oh, somebody deleted this piece of data.” It kind of sucks to have things moving while you’re also writing the code on it. I’m sure you went through this with Drip. There’s so much…
Rob: That’s SaaS though.
Mike: I know. It’s like open heart surgery–it feels like sometimes.
Rob: Yeah, every time we did anything meaningful to scheduling or, I mean there’s all kinds of stuff that’s so easy to screw up. If you can figure out a way to smoke earn—not smoke test—but to get you in a test on that stuff because the fact that you don’t feel comfortable making changes to a part of your app, that’s going to be a hindrance forever. It’s not going to get better, it’s only going to get worst especially if it grows, if you start hiring people, that’s a big red zone there that I think you need to think about remedying early.
Mike: Yeah. […] is there’s a component that I’m using where to get into the technical details of it, there’s a C# Class and I have to serialize it. In order to do that, in order to store the data. The problem is they’ve marked it as sealed which means I can’t inherit from it, which means I can’t really do anything with it. I’ve been working with them to try and figure out like, “Is there a way I can get an interface for this or something like that so that I can create it?” Because they don’t have a public constructor for it because it’s a sealed class, it’s encapsulated in the assembly, I can’t narrow from it either. I really don’t have any other options other than faking it which is what I’ve done so far. I basically have my own object that very, very closely mimics theirs, but it’s not perfect, and that’s the problem. I’ve found a few edge cases here and there, it’s kind of scary. I’m hoping it will come up with a solution sooner rather than later, but I’ve been working with them for probably six months on it.
Rob: One minute while I update my spreadsheet. Let’s see, apps to not start as an unfunded single founder, email marketing for writer, cold email outreach–the list is getting longer and longer. It’s like, these things don’t seem that complicated when you look at it from the outside. “I want to build an ESP. This is going to be a piece of cake.” said Derek and I before we wrote code.
Mike: I think anything where you have an outside dependency that you don’t completely control or have complete access to, that’s where it gets hard. Or you’re relying on events coming in to the system and you have to do data processing on.
Rob: Alright. Well, let’s keep moving on with this episode. Our second comment on episode 406 was from Don Gooding. He linked over to a few articles he’s written and one of them which we’re going to discuss today. His comment was, “I write a lot about bootstrapping versus venture capital or angel funding. They’re definitely a bunch of issues to consider both early and later. I hope you’ll consider the following posts helpful and not spammy.” and I do consider them helpful. He links to three different articles. His blog is fourcolorsofmoney.com. Don, if you’re listening, register the 4colorsofmoney and also, redirect that over because I tried that as well and it just goes nowhere.
He linked to the first article which is, Bootstrapping Versus Venture Capital: 19 Questions to Ask–we’re going to talk about that today. He also linked to another article called, The Bootstrap to Funding Pivot Playbook which is about bootstrapping first and then raising funding later. He talks about revenue financing in that one. Then his last article is, Revenue-Based Financing: Five Different Options and he walks thru them which is pretty interesting.
His site is called Four Colors of Money because he looks at bootstrapping, he looks at grants, he looks at grant and equity–those are the four colors. He’s obviously—having read through it—pretty knowledgeable about this stuff. Again, we will include those three links in the show notes. You can always go back on those comments on episode 406 if you wanted to see his full comment.
But today, we are going to talk through his article Bootstrapping Versus Venture Capital: 19 Questions to Ask. We won’t have time to go through all 19 question, but the idea here is to think about whether you can and should bootstrap or whether you need to raise funding.
His first question is, “How much of your own capital do you have. Do you have a way to self-fund it?” Self-funding and bootstrapping sound like they’re the same thing, but they’re different. Bootstrapping is truly having almost no money. A few hundred dollars, a thousand dollars, a couple thousand dollars, and then growing a business based purely on its revenue and profits.
Self-funding is if I have $1000 in the bank or $200,000 in the bank, or I had another business that was throwing off money or another income stream that was throwing off money that I could then take and start my next business from.
Self-funding is a lot of what I did. In the early, early days, I bootstrapped everything right out of consulting revenue but spent very little money. Then the more business revenue I had, I stayed consulting during the day full-time, and I took that business revenue and used it to self-fund the next thing, and the next thing, and the next thing, and each of them got bigger and bigger. It took me a long time to get from having .net invoice doing $300 a month, 10 years later, even longer, 11 years later, it’s Drip doing seven figures a year and having exit.
I didn’t have to raise during that time because I self-funded, but it took me a lot longer than if I had come up with an idea and just raised funding early on. That’s kind of how I think about the trade-offs is I believe it takes longer if you’re in a self-fund unless you do have a rich uncle or a trust fund. But his first question to think about is how much capital on your own do you have that you can invest in the business?
Mike: I feel like this is more of a runway question because the money itself, you either have to when the business itself is generating money, how much is left over for you to leave versus how much are you going to be able to put back into the business. If you’re running a business on the side or on nights and weekends and stuff like that, then you presumably have a full-time job, and that is keeping your self alive and your family fed while the business is getting the rest of the profits. But at some point, things are going to transition, and you have to make some choices about like what your future looks like, do you have enough money to be able to spend $1000 on ad words or something like that to test out a market? You may even need that money early on.
That comes down to the fundamental question that he’s got here is, how much of your own capital do you have? Can you afford to run experiments early on? Do you have more time on your hands or do you have more money? This is getting more at the money side of the equation. If you have plenty of time, if your timeline is five years, you can take as long as you want to do most things. Certain industries of course will move very quickly, and competitors will swoop in, not ideal if you’re trying to take five years to do it but certain ones you can do that.
I think Patrick McKenzie, with Bingo Card Creator, he slowly built that up. Nobody else wanted to get into market because there wasn’t a lot there. But he was still able to make a pretty good business out of it. He just took a really long time to do it.
Rob: His next few questions look at ways that if you don’t have the money to self-fund, ways to look around and see if you can essentially raise funds but not from venture capitalists or angels. His second question is, how likely it is you can raise funds from family or friends. Third question is, “Can your product support a Kickstarter style campaign?” which I believe a lot of people overlook. Info products and even some software, not B2B, but have to really be B2C in general can use Kickstarter as well as obviously physical products would be a great way to do it. His fourth one is, “Will customers pay you well in advance of you delivering your product or service?” Can you essentially pre-sell it? His fifth one actually is, “Does it qualify for a grant?” I don’t think that applies to most of our listeners nor any business I’ve ever started, but it is one of the colors of money that he talks about.
Mike: You know, I’ve thought about this kind of crowd funding. I’ve heard people gone down that path, not on Kickstarter, but someplace else, I can’t remember the name of it.
Rob: Like Indiegogo or something?
Mike: I think, yeah, it was Indiegogo. The general consensus was people are much more willing to fund individual ventures and things where there’s a physical product. But when it comes to software, people are not particularly interested. Maybe that’s just because it’s kind of self-selecting where the people who are building those generally are targeting them at businesses versus if you’re going to do something where it’s like, “Oh, this is a way to organize baseball cards,” or something like that, if it’s something that has a wider appeal and it’s a non-business use, you’ll find the hobbyist into that or the people who are prosumers, so to speak, they are going to be into it, and they would probably fund it. But if you’re going to try and create a CRM or something like that, who’s going to fund that? I can’t think of anyone who would want to willingly throw in money unless it was for their own business at which point, it’s not really for the greater good so to speak.
Rob: Totally. When I look back at the 173 Kickstarter projects that I’ve backed. Mike, did you hear what I just said?
Mike: Oh my god.
Rob: Oh, no. That’s the number of successful projects I’ve backed. I’ve 185 Kickstarter projects. Oh, the humanity, Mike. It’s so embarrassing. I just love Kickstarter. But I don’t think I’ve backed a single piece of software. My taste, it’s a lot of graphic novels, it’s a lot of table top games, it’s a lot of little tech gadgets. There was a Kano–the open source computer that I could teach my kids how to put computers together and do that stuff. A lot of it is some learning, some teaching, and some gadgetry and stuff. I think that my gist is that my taste are not uncommon. I do agree that in trying to launch a project in Kickstarter would be hard. But there are a lot of listeners who are not just trying to do B2B software as we’ve talked about.
I’m going to skip over a couple of these questions. But another couple of questions that I think are interesting to ask because they imply that you should probably raise some type of at least angel and potentially go after venture funding. One is, “Do you think it will take more than $100,000 and/or longer than one year to develop your product or service to the point that it is generating revenue?” Another question is, “Does your business have network effects where only one or two companies will end up with 80% or 90% of the market?” because that’s a super protectable. There’s a moat around that product or around that business. That is something that can very likely be fundable.
Another questions is, “Do you have large capital equipment or other fixed investment needs that aren’t debt financeable?” those three would obviously imply that you probably need to raise some kind of funding.
Mike: Well, I look at those things as potential disqualifiers as well because if it’s a network effects type of business where only a couple of companies are going to end up with a large percentage of the market, to me, that’s kind of a disqualifier unless you’re going to go raise money, and which I guess is kind of what he’s saying, but you have no idea if other people are going to answer in there who have a lot more clout than you. That’s why you should probably go raise funding if you’re going to go for something like that. But you’re also going to look at that particular thing and say, “This is a disqualifier for me. I’m not just going to go in that direction because I don’t want to raise money.”
Rob: Another good one I like that he asks is, “Do you have potential customers that will see your small sizes of risks? For example, a potential career–a limiting decision.” In other words, if you’re selling to banks, large institutions, they’re going to require that you have some kind of backing, right? I shouldn’t say require. They’re going to be unlikely to go with a single founder building software out of his/her garage.
I remember talking to someone at Gumroad actually, because Gumroad was kind of bootstrapped early on, and they raised a big round, I believe it was 7 million if my memory serves me right. I was saying, “Why did your raise the round?” He said, “Well, we wanted to become a credit card processor.” And to actually process credit cards, you need a bunch of money in the bank. They just won’t let a bootstrapper do that, or a self-funded company do it. I think that’s definitely a case if you’re trying to start a Stripe or even a Gumroad which seems it could be a bootstrappable company, there maybe a case where you need to pony up and raise a little bit of money.
Mike: That’s just a social proof of creditability factor. You’ve got people who have been willing to invest $7 million in you than it serves to the banks as like, “Oh, these people have convinced these other seemingly smart people to give them $7 million. Clearly, they’re onto something and they know what they’re doing.” Doesn’t mean that that’s true, it just means that that’s what their perception is. You’re really just playing off their perceptions.
I think there’s certainly situations where you can either skirt that or use it to your advantage for a relationship or something like that. If the […] that you’re getting after like you get an introduction into them. That way, you’re not going in completely cold. If you can get those introductions from somebody that they trust, then that’s going to help out a lot. That’s a place where if you go into different reseller channels, and there’s tens of thousands of resellers across the world, that their sole business is to go in and sell software to other businesses.
There’s a bunch of large value-added resellers like Dell and HP, in companies like that where they have entire channel programs set-up such that they’re going to and work with small businesses or they will escort small businesses into a deal in order to provide the credibility, and then everything goes down on their paperwork.
That’s how Dell and HP have, like massive services businesses, it’s because they have all the relationships already, they have sales fields reps, they walk in because they have a relationship or they can just make a phone call and say, “Hey, I’m your Dell rep and I’d like to come in and talk to you.” And then they talk to you and find out what your problems are, and they escort a small partner in the door.
If you can get some of those relationships, you can basically get escorted in. You don’t need to have that $7 million in the bank or you don’t have to hire 300 sales people or call center in order to do outbound cold calling in order to find your leads. You can leverage those partners to help walk you in.
Rob: His last few questions are really surrounding this topic of, “Are you a fit for angels and VCs?” One is, “Will your business support growing sales by 50-100% annually for 5-7 years? Will annual sales reach $15-$50 million with that timeframe?” high-growth, right?
Another question is, “Are you comfortable selling your business in order to provide your investors their return in five to seven years?” or maybe earlier for VCs. “Are you comfortable sharing control of and decision making for your company with investors? Is your team plan and pitched in the top 10 percent of companies seeking financing in your region?” All interesting things to think about.
Mike: I think that a lot of those are hard questions to answer too. I’ll say they’re very personal questions and depending on the time and day that somebody asked you, you might also change your mind. It could be hard to come up with a solid answer that you stick with.
Rob: Yup. I would agree. I think these are good things to think about. I think long time listeners of the podcast will have heard us discuss these types of thought processes before. Well, if you’re new to the podcast, you probably think, “Boy, these guys really talk about funding a lot for a bootstrapping podcast.” because in the past five episodes we’ve talked about it twice.
But I do think that it’s becoming more and more relevant. I don’t expect us to talk about it every five episodes by any stretch, but it does seem to be this emerging trend that is coming into the startups space. I think back to 2007 to 2009 or ’10, and I was using a lot of email marketing in my info products, and then I started bringing them into software products and kind of the startups space, it was definitely this emerging trend that I recognized. I talked about it at BOS.
Split testing was something I had seen in info and people in the startups were not doing that, that also became a trend that took off. There’s a bunch of things that have come from different angles. Even customer development and a lot of lean startups stuff was taken from the automotive. You see these trends coming in.
While startups and software have traditionally been VC funded and the trend that you can I have been a part of is this bootstrapping and self-funding kind of spearheading it, I would say, or I mean at least part of the folks who have really driven it over the past eight plus years. I think we look back and the first time I had said “fun strapping” on the podcast was in 2013 or 2014. It’s becoming just a little bit more common for folks to raise a round and not go institutional, which is another trend that I see, not infiltrating because that sounds like it’s a bad thing, it’s just another trend in the space. I think we’re just continuing the dialogue about it to keep abreast of what we see is happening.
Mike: Yeah. Things just change over time. As time goes on, the entire software space has become more and more competitive. I mean, eight years ago when we started podcasting, it was easier to launch products in terms of getting in front of customers. Now, there’s lots of competitions. You have to have a more polished product, it’s got to be further along, it’s got to solve more of the customer’s problems because they’ve got other things that they can pay attention to.
It just makes it, I’ll say a little bit more challenging to launch a product today than it is yesterday, than with the day before. As time goes on, I think that that trend is just going to continue. I say that the natural evolution is you have to have more resources in order to launch something. It’s kind of where the industry is headed. I’m not going to say that that’s where it will end up and that you’re always going to have to raise funding in the future because I don’t think that’s true. But I do think that there are certain types of businesses where it makes a lot more sense to raise some funds than it is to not, especially with certain life circumstances as well.
Rob: Yup. The good news is that it’s easier, I would say, than it has been in the past to get some type of small amount of funding with a lot fewer strings attached than say, 10 years ago. On the flipside, like you said, I believe there’s always going to be bootstrapping. That’s not going to go away. There’s always going to be folks who are hacking away, launching small software products, getting a lot of learning, getting some revenue. I think that’ll last forever and I think that’s a really great thing.
I’ve said this before, we live at an amazing time in history where even 30, 40 years ago, you couldn’t do any of this, and 100 years ago it’s even worst. But now, someone with some type of technical acumen can basically start a whole side business and really never leave their house and have this thing making money while you sleep. It’s always been the big draw I think for a lot of us. Part of it might eb the adventure and the active creating, I think that’s a big deal, but to be able to literally make money from nothing more than your skill and your computer is just mind-blowing. When I think back to being a kid, I was in junior high in high school and it was like, “Well, I don’t really want to work in a cubicle but were my options?” Right? In the mid to late ‘80s. This stuff was just coming about and I didn’t know much about it but the fact that we live at this age–consider ourselves lucky.
Mike: I think at the end of the day when you’re trying to evaluate whether or not to raise funds, it’s all about that trade-off of time versus money. Do you have money to burn? Burn is probably not the great way to put it, but do you have money to spend in order to learn quickly or are you okay taking a much longer time to do it, and doing things slow and steady based on what your financial situation is like, your personal life, and how much time you have available. That’s going to be different for everyone. That’s what generally governs these types of decisions for most people. I think that about wraps us up for today.
If you have question for us, you can call it into our voicemail number at 1-888-801-9690 or you can email it to us at firstname.lastname@example.org. Our theme music is an excerpt from We’re Outta Control by MoOt used under Creative Commons. Subscribe to us in iTunes by searching for startups and visit startupsfortherestofus.com for a full transcript of each episode. Thanks for listening. We’ll see you next time.
In this episode of Startups For The Rest Of Us, Rob and Mike answer the question of should bootstrappers raise money? The guys distinguish the difference between venture capital and angel investing and how raising an angel round may be a good fit for some types of entrepreneurs.
Items mentioned in this episode:
Mike: In this episode of Startups For The Rest Of Us, Rob and I are going to be talking about whether bootstrapper should raise money or not. This is Startups For The Rest Of Us episode 406.
Welcome to Startups For The Rest Of Us. The podcast that helps developers, designers, and entrepreneurs be awesome at building, launching, and growing software products, whether you build your first product or you’re just thinking about it. I’m Mike.
Rob: And I’m Rob.
Mike: And we’re here to share our experiences to help you avoid the same mistakes we’ve made. What’s going on this week, Rob?
Rob: We have new iTunes reviews.
Mike: Oh, cool. What do we got?
Rob: This one from Find Fitness Pros. It says, “This is my go-to podcast every Tuesday morning. Rob and Mike continue to give their insights, not just info on exactly what to do,” and from Nathan Bell, he says, “Great information. I listened to one episode and I’m hooked. It was full of great information I can easily implement. Some of the info was a little bit advanced for me currently, but I’m confident that by selectively listening to more, I will pick up more.”
Those are a couple of new iTunes reviews that we have. I used to keep a worldwide tally of it using CommentCast and when I moved to my new computer, I don’t have the .exe or what is it called, it’s a .app I guess in Mac. I don’t have the executable anymore and you can’t download it anywhere. So I moved over to mypodcastreviews.com but it only gives me reviews, not ratings. We’re up to almost 600 worldwide ratings, I believe. People don’t necessarily need to write sentences or whatever, but I don’t have that tally anymore. Certainly, we’re above 600 at this point.
Now, what I have is I have 347 worldwide reviews and that’s a lesser number. I want to get back to the world’s rating. I think the guy at My Podcast Reviews says that they are going to add ratings but neither here nor there, the more reviews or ratings we get, the more likely people find the show, the more motivation it gives us. If you feel like we’ve given you some value as a listener to the show, it would be awesome if you can open iTunes or Stitcher and just give us a five-star review. Really appreciate it.
Mike: The solution to not having that app that gives you the numbers is just make up a number. So we’re at 3000 reviews I think.
Rob: That’s right. 3422 reviews. That’s great. How about you, man? What’s going on this week?
Mike: Well, this morning, I published a public API for Bluetick. Of course, I say it’s a public API but there’s actually only one person who actually knows about it.
Rob: It’s in beta?
Mike: Yeah, basically.
Rob: Early access, good.
Mike: I had a prospect who wanted to sign on and they’re like, “Yeah, I really need to have a public API that is available for me and Zapier wasn’t going to work for them. Basically as I said, I spun it out because I heard from a bunch of customers that I currently have, and I started talking to them about, “What is it that you need?” and trying to figure out what’s the minimum that I could build that this particular prospect or customer would need to get started. They only needed four things. Build those, put them into it, and then there’s all the infrastructure changes that needed to go into it.
It took a week-and-a-half just to do the infrastructure changes but now the best stuff if all taken cared of. I got that published out there and waiting for them to start using it, and then figure out what needs to change. I already made it very clear upfront, like, “Hey, here are some things that I know we’re going to change, and then over here, based on what you tell me, other things could change, so treat this as an absolute beta. Eventually at some point it will become stable, I guess, and then I’ll start pushing it live to everybody.
Rob: That’s nice. It’s nice to do. You’re basically doing customer development on what is its own little product. You can say it’s a feature but really some entire products are just APIs. You want to get it right from the start, and by start, I mean by the time you publish and people start hooking into it, you can’t change it at that point. I think it’s really good to take this approach of roll it out slowly, roll out one endpoint at a time and really think through how you want to structure it.
I was just on your site trying to guess the URL. I was going to just type in a bunch of stuff so you’re going to see a bunch of 404s in your error logs. Not a hacker, it was me, but I didn’t find it alas.
Mike: No, that sucks. I would tell you if you asked for the right price. Other than that, I also got my first fraudulent charge from Bluetick. It took a lot longer than I expected it to but somebody signed up, then they logged in, and absolutely they didn’t pay any attention to the onboarding emails. Come time when their trial is up, they got charged, and then I forget how long it was later. I was maybe probably three or four days later, I got a notification from Stripe saying, “Hey this charge looks fraudulent,” and I looked at it. I think it’s a debit card too and I was like, “Oh great.” Three hours later though like, “Oh you’ve had a chargeback.” I was like, “Wait, I didn’t even get a chance to decide that to do with this potentially fraudulent charge,” and they already converted it into a chargeback, which cost me an extra $15. Well that sucks, but, oh well.
Rob: Was it a person not using or was it a stolen credit card? Is that what you think? Or do you think that they just went in with the intention that it was their own credit card and they just intended at the whole time?
Mike: I’m not sure. It looks legit. The email address, I couldn’t quite tell whether it was real. I think it was a Gmail email address. I couldn’t really trace it back to a company or anything like that but the name on it seem to match what the email address was. I don’t know. I’m not entirely sure but I think it was from a real estate company or something like that. All right, well, whatever.
Rob: Yeah, that sucks. It’s going to happen. It’s definitely a milestone you don’t want to hit but you’re going to hit it eventually.
Mike: Yup. Certainly not a milestone to celebrate but I definitely hit it.
Rob: Yeah, exactly. Cool. What are we talking about today?
Mike: Today, I thought we would have a discussion about whether or not bootstrapper should be raising money. I guess by definition if you’re raising money, are you no longer a bootstrapper at that point? I think there’s maybe a time during which you are bootstrapping a company and self-funding it. I almost called it self-funding, like should people who are self-funding raise money, but again that would go against it.
The idea came because I saw Justin Jackson had tweeted out a link to an article he wrote over on Indie Hackers called The Bootstrapper’s Paradox. In that article, he shows a graph or what they’re doing for transistor.fm, which is the new startup that he’s working on. Basically it shows a graph of over the course of 60 months was 10% exponential growth and 5% turn. The MRR will get to $21,000. But 60 months is five years of time.
I thought it would be interesting to just have a conversation about this because when I was reading through the tweet that he had put out, there were a bunch of people who chimed in on it, mostly people who were listening to the show would have heard of like Des Traynor, Jason Collin, and Natalie Nagel. They’re giving their thoughts on this stuff and I just thought it would be interesting to talk about it.
Rob: Yeah, that’s for sure. 10% growth every month sounds like an impressive number but when the number starts very small, like $1000 a month, that means you’re growing $100 MRR a month. You just can’t do that early days or if you do, it’s going to take five years. You either need to figure out a way to grow faster or you need to be really patient.
This is a struggle. It’s funny that, Justin called it The Bootstrapper’s Paradox. I don’t know that it’s that as much as this is the reason people raise funding. We know people who are just bootstrapper through and through, you should never raise funding and 37signals used to say that and even mentions it that DHH and Jason Fried took funding from Jeff Bezos two years after launching Basecamp. It wasn’t even funding that went into the company. They took money off the table. If I recall, I think that number is public. I think it’s $10 million that he invested, was my memory and maybe I don’t think I’m making that up. It’s either rumored at that or it was announced.
They had essentially at that point had FU money and it’s really easy to make different decisions or just say, “Hey, we’re going to grow as slow or as fast as we need,” when you have that kind of money in your personal bank account and you’re just running this business day-to-day.
Justin’s article is a bootstrapper’s realization of “Oh Sh*t.” This is why people do raise money. It’s coming to that realization at this point and I think it’s a good thing to call out for sure. I’ve been thinking about this so much so I’m looking forward to today’s episode because in my Microconf talk this year, I talked about things that I learned bootstrapping and then self-funding and then in a venture back company after Leadpages acquired us.
In the last five to seven minutes I did just a little snippet about fundstrapping, which is this term that Colin from customer.io coined, where you’re kind of in-between. You bootstrapped a little bit and you raised a small round. I say it’s between 200,000 and 500,000 and you raise it with the intention of getting to profitability. Without, you’re never going to raise institutional money, or raise it from friends or families or angels, so you don’t give up control, you don’t give up a board seat, you really have the benefits of funding without the institutional chaos of it, the headache.
It wasn’t a throwaway piece but I almost didn’t include it in the talk. That piece has gotten me more emails, more comments, more thoughts, more people came up to me, ask me what that’s like, asked if I would invest or find new people who were doing fundstrapping. It’s just fascinating response to this, this thing that’s been percolating. It’s a long rant on it to start but I just think this is becoming more and more of a viable option and potentially even a necessity as the SaaS market gets more and more crowded.
Mike: Yeah. That’s the part that I think has changed over time, where five or 10 years ago, you could come out with a SaaS and you’d launch it to the public and you would start to grow by virtually the fact that there was nobody else out there or there were very few competitors out there doing what you were doing. Now if you launch anything, you probably got a couple of competitors just right out of the gate. If you don’t, then you probably don’t have a product that’s going to go anywhere. But if you have any competition, it’s probably substantially more competition today than you would’ve had five years ago or 10 years ago. Just by virtue of having launched five or 10 years ago, you were going to be more successful quicker than you would if you did the exact same thing now. It’s going to take longer, which means that you’re going to burn through more runway and it’s just going to be harder.
Rob: Right. Now, five or 10 years ago, there was less competition but the expenses would have been higher, 10 years ago especially because you literally needed a rack server. There was no Amazon EC2. In addition, there was still like when Basecamp first launched on their homepage, they were like, “You don’t have to install any software. No downloads needed.” They were still educating on just the concept of being in the cloud and there were hurdles there.
Mike: That was almost 15 years ago.
Rob: Yeah, that’s true. No, you’re right. That was 2005 or 2006? You’re right, 12 or 13. You’re right. But even with that, say 10 years ago, even with that, it’s still I believe was easier back then. But that doesn’t mean you shouldn’t start something today. It just means you got to house some more, you got to pick a better niche, you got to have more skills, or you need a little more money in the bank.
Whether that means you raise it yourself out of consulting efforts, which is what I did, or if there’s definitely more money being thrown around as funding these days that is, I’m not going to say no strings attached because it’s certainly they take equity, but 10 years ago if you took half-a-million bucks, boy that was typically institutional money, it was a pain in the butt to raise, you are giving up a lot of control, you are giving up a board seat, that is no longer the case. There really is this viable option, this in-between.
Mike: I think if you look at the businesses that, in the past have tried to figure out how to raise capital, one of the things that most people, 15-20 years ago, it was common to say, “Okay, let me go to a bank and get a loan from the bank.” But that is a non-starter for most new businesses. You got SBA loans and things like that where you can use the money to take over an existing business where they’re able to evaluate.
But if you have a business that you’re trying to get off the ground, a bank loan is basically a non-starter, especially when it comes to SaaS because they don’t understand how to calculate how much that business is worth. There isn’t any inventory and with software, it’s going to lag in terms of the revenue over something like a physical goods business, or a coffee shop, or a fitness studio where they know how many people are coming in and they can put a value on the equipment whether it’s the coffee machines or the spin cycles on a fitness studio. Banks are okay with that. They understand that.
But when you got a software business, the expectations today are much higher than they were five or 10 years ago. You have to do a lot more in order to make your product a lot more polished, which means it’s going to take time to do that which burns through your runway. It burns through that money a lot faster today. I guess you wouldn’t burn through it faster. It’s just you burn through more of it than you would have 10 years ago to get to the same point.
Rob: Even if you can get a loan, you have to send a personal guarantee. Now, all your personal assets are on the line. And if you decide to shut the company down, you owe them money. If you borrow $100,000 it’s a big deal. To me, that is more of a risk than I think an entrepreneur should take, unless you’re at the point where you already have, “All right, I’m at $10,000 MRR,” in which case you may or may not need the money, but if you’re at $10,000 MRR, you should raise equity funding anyway.
But if you know the business is going to succeed, that’s fine. When I hear that people charge $50,000 or $100,000 on credit cards to start a SaaS business, I’m like, “Oy vey.” That is going to be catastrophic. That is a really, really stressful way to live and it’s something I would not do, especially when we’re in a space where raising equity capital is relatively inexpensive. Raising a small angel round and selling 10% or even 20% of your company to reduce a lot of stress and to get there faster, I think it’s a pretty reasonable idea these days. It’s not impossible to do, I’ll say.
Mike: I want to talk about that specifically right there. What you just said was raising capital is relatively inexpensive. The reason I like the way that you put that is that when I think of the way I thought about raising funding years ago was that, “Oh, I’m going to have to give up a lot of control, I’m going to have to give up a lot of equity, and I don’t necessarily want to do either of those things.”
But if you’re thinking about putting together a business and you have anybody who’s helping you—a partner or a co-founder, something like that—your immediately giving up 50% of the company anyway, and then there’s a whole lot of difference between doing that and giving up 50% when there’s really nothing there, and yes, it could grow up to be something huge, but you’re giving up 50%.
So there’s like a mental block there of you saying, “Okay, well I’ll raise $250,000 in exchange for 10% of this,” and you don’t want to do that but you’re willing to give up 50% to somebody else when there’s really nothing there that’s being invested except for their time. Do you know what I mean?
Rob: Yeah. It’s cognitive dissonance I believe is the term where two things that don’t agree or paradox, I guess. It’s something in your head you’re rationalizing one way but then you turn around and give away 50% to a co-founder. That’s what you’re saying, It’s like you can give a small amount to get a big chunk of money, or even if it’s a small chunk of money.
Here’s the thing. Let’s say you live in the middle of Minnesota, or the middle of Nebraska, or something and you have an idea and you raised even $100,000 or $150,000 and you paid for your salary for a year or a year-and-a-half. That gives you a year or a year-and-a-half to get to some point of revenue that makes sense. Even if you gave away 15% of your company, you’re valuing it at $1 million right off the bat, or if you give away 20% or $750,000, it still makes your life a lot easier.
I think that’s the realization I’m coming to, is that at Microconf, or through this podcast, or whatever at different conferences, we meet smart people who are trying to launch businesses and something that stands in their way often is that, “I have a wife and kids. I have a house. I can’t do this nights and weekends. But I don’t want to raise funding because it’s really complicated. I don’t know how.”
What’s funny is you outlined this episode and you brought the topic up. But this is something I’ve been thinking a lot about, and there’s a gap here in the space. We do have folks like indie.vc which, if you haven’t heard my interview with Bryce from indie.vc, it’s episode 310 of this podcast, and it’s a more realistic approach to funding. It’s kind of a fundstrapping model. I’d recommend you go listen to that.
In addition, I feel we’re coming to an inflection point where there’s this gap and there’s a level of interest in something, and no one is filling it. No spoilers on what I’m up to next, but I’m starting to feel I might be the person to tackle this, to take it on. I’ve been spreading the word about it. I have been talking about it for years and I’ve been investing in startup like this.
We talk about Churn Buster, LeadFuze, CartHook. These are all small angel investments. I’ve done about 12 angel investments and I think three or four of them were essentially fundstrapped. it’s where they took money from a handful of folks and they never planned to raise a series A. I put my money where my mouth is, but now I’m thinking I only have so much money, how is it that I can take this to the next level in a realistic way. It’s something that’s definitely in the back of my mind and it’s something that I’ve been thinking a lot. Hopefully, we’ll dive into more in the future.
Speaking of that, if you listen to this and your thinking, “Oh, this is an interesting topic,” go to robwalling.com. Enter your email because it’s going to be something that I’m going to be thinking more about in the future as well as on this podcast for sure.
Mike: One of the comments that jumped out of me on the Twitter post that Justin had put out there was from Des Traynor and he said, “I think a second piece people don’t really internalize is that 60 months of the best years of your career is a substantial upfront investment too. Like a seed round but instead of money, it’s your life.”
That’s a fascinating way of looking at this because even back n the day, I would always say, “Oh, well. You know you’re basically trading money for time,” and I don’t think that I really equated time with years of my life. It sounds intuitively obvious. That’s exact same thing. But when you’re in the middle of working on stuff, you don’t think, “Oh, I’m trading five years of my life away of hard toil to get this thing to where it could be a lot sooner if I were just to take some money and trade some of that equity for it.”
Rob: Right. It could feasibly be a lot sooner. It may or may not. Money doesn’t solve all the problems but it certainly makes things, I’ll say less stressful and you having done it with true bootstrapping with basically nothing and doing nights and weekends, to then self-funding with revenue from HitTail going into Drip, and then venture funded. I’ve done all three of these. I will tell you that having that venture money, I didn’t have to raise it and I did attend the board meetings but I didn’t necessarily have to report to the board. My life was less stressful at that point than either of the prior two scenarios.
I think it’s a good point, man. I don’t want to come off. You can tell, I’m coming off kind of pro-raising a small round, and I don’t want to come off too one-sided. We’ve never been anti-funding ever. From the start, Microconf, I think in the original sales letter. It was, we’re not anti-funding. We’re anti everyone thinks the only way to start a software company or a startup is with funding. That maybe from the introduction of my book, actually—Start Small, Stay Small.
Even back then in 2010, I was saying, “Look, raising funding is not evil in and of itself. It’s the things that you have to give up by raising funding. Just know what you’re getting into.” Yes, we have seen founders that get kicked out of their own company. There was, I figure what that app it was. Was it Tinder? Something sold for $460 million. No. It’s FanDuel. It’s sold for $460 million and the founder who started it, and I believe was CEO when it started, he got no money because of liquidation preferences and he’s suing them.
That’s a huge exit. He got I believe it was zero dollars from the exit. There was an article or something that was like, he’s suing them now. If the contract say this is what the liquidation preference is, that’s one thing but he’s suing them because he thinks they screwed with the valuation intentionally and there was fraud or something. He’s not going to win if he just says, “No, that wasn’t the deal,” because he signed the papers. These VCs are not stupid but he’s trying to do that.
Yes, that does happen. But I believe there is a way to do this and I’m seeing it with these smaller SaaS apps. A way to do it without that much stress, without giving up that much equity. Brennan Dunn, RightMessage. That’s another one. I also wrote a check. And Rand Fishkin’s SparkToro. He’s doing the same thing. He’s not calling it fundstrapping, but he said, “Hey, we’re going to raise around, and we’re going to get to profitability, and we don’t want to do institutional money. If you listen to Lost and Founder which is his book, he talks about the perils of all that and you couldn’t read that and say, I can see really they didn’t like – once they raise funding, he really didn’t like it.
You can look and say, “Well, Rand’s anti-funding now.” But no, he’s more anti-institutional money, and there’s a difference. Venture capital is institutional money. These angel rounds tend not to be.
Mike: But I think even back, we’ve talked about it on the podcast before. As you said, we always had the position that, it’s not that we’re anti-funding, we’re anti-this-is-the-only-way-to-do-it. That’s always been my thought behind it. I’ll say the majority of my career and thought process has been like, “Yeah, I really just don’t want to take funding in this more because I don’t want to necessarily give up control.” Back then there weren’t really the options for that. Now, things have changed a lot. It’s not, say, front and center on my radar, but it’s something I’m definitely looking at niche and exploring a little bit more.
I definitely think that—like with Bluetick for example—there’s ways to go further faster, but I just don’t necessarily have the money to be able to do it, which sucks but at the same time, it’s always a trade-off. I think that’s what you always have to consider is, what is the trade-off and what am I going to have to give up in order for me to get X amount of influx and then what are you going to do with that?
You have to have a plan. You can’t just say, “I want to raise money.” You got to have a plan for not just raising money but also what are you going to do with that money when you get it? How are you going to deploy it? How are you going to build the company and how are you going to grow things? You can’t just drop $100,000 in your bank account or $500,000 and say, “Okay great. I’ve raised money. Now what?” They’re not going to give you the money if you don’t have a plan.
Rob: And if you don’t know what you’re doing, money’s not going to fix that. You’re just going to make bigger mistakes. This comes back to the stair-step approach. No chance I would have raised money in 2005-2009 with ,DotNetInvoice, and Wedding Toolbox and just beach towels and stuff. Even if I could have made the case that DotNetInvoice would grow to something, I would have made huge mistakes because I made small ones back then. But I learned and I gained experience and I gained confidence.
By the time I get to HitTail, I remember thinking, “Yeah,” because remember, I bought HitTail for $30,000 and then I grew it up to basically that much MRR per month but end and I value at it. Maybe I should raise a little bit of money in it. It would make this a little easier. But to me, it was the headache of it. I was like, “I do not want to slog around and spend months asking people and the paperwork.” It just felt like a pain in the butt to me. I don’t know if I could have. Did I have the name recognition? Could I have raised enough?
Arguably, yes. By the time I got to Drip, it was definitely like it. If I haven’t had that HitTail money, let’s just say I’d had none of it. I basically used a bunch or revenue from HitTail to fund Drip. If I hadn’t had that? I absolutely would have seriously considered doing what we’re talking about raising a small round. I knew Drip was ambitious, I knew it was going to get big at least by the time we are six or eight months in, and it had a need for that.
That’s what we’re saying here is the words always, never, and should, they’re not helpful words. Don’t say, “I should always raise funding.” “I should never raise funding.” “I should raise funding other people think I should or shouldn’t.” These are not helpful words. Just evaluate things and look at them, and like you said, look at the trade-offs. Pluses and the minuses, and the realities of them, not the FUD. Not the fear, uncertainty, and doubt.
I can tell you the story, “Oh, look. The founder of Fandle. He got screwed by his investors. Therefore, I’m never going to raise investing or I’m never going to raise funds.” That’s dumb. Actually look at the black-and-white of it. I think that’s what we’re talking about today. We;re not saying you should or should not, but it’s look at the reality of it.
Now, you and I talked about this in-depth in episode 211, When To Consider Outside Investment For Your Startup. We went in-depth on what are funds and family round, an angel round, or often called a seed round was. We talked about series A, B, C. Once you get to the serieses, that’s when you get to institutional money, which is when things get way more complicated. Once you raise a series A, it’s the point of no return. It’s implied you’re going to raise a B, a C, and go on to either have this huge exit or an IPO, and it’s growth at all cost for the most part.
But if you’re able to stop before that series A and stick to people who are on board with you, angel investors and such are on board with, “Hey, let’s build a $5 million, $10 million, $15 million company with it, it’ SaaS. Let’s do a 30%, 40%, 50% net margin on this thing.” That’s great. That’s the kind of company I want to build and that’s the kind of company I want to invest in.
But venture capitalists don’t want to invest in that. If that’s not your goal, to go to $100 million and do what it takes to do that, then you don’t want to go down that road. You want to have those expectations clear both in your head upfront, as well as anybody who’s writing you a check.
Mike: Right. The problem with that is that episode 211 when we talked about that, that was four years ago. That’s a long time in internet time.
Rob: I might need to go back and listen to that episode to hear what we said. How much you want to bet? Oh, I’m going to go search it and see if the word fundstrapping if I mentioned it in there.
Mike: I don’t think so. Oh, it is.
Rob: Is it?
Mike: Yup. About 20 minutes in, you said, “I heard the term fundstrapping and I really like it. It was from Colin at customer.io.”
Rob: There it is. In 20 minute then boom. This is 2014, November of 2014 even back then.
Mike: But you were in the middle of Drip at the time, were you?
Mike: Was that right?
Rob: Yup. In the middle of Drip and I was probably already thinking about because at this point, we were growing fast and I was dumping all the money I had into it, both from that revenue and from HitTail, and I was thinking, “Boy, if I had half a million bucks right now, given our growth rate could have raised it. If I had half a million bucks right now, we could grow faster. I can hire more and have more servers and not shut down EC2 instances on the weekend.”
We used to do that to save money that’s insane, that lengths. I remember valuating Wistia versus SproutVideo, and Wistia, for what we need, it was $150 a month and Sprout was $30. It’s a nice tool but now way it was Wistia. I went with SproutVideo because I needed that $120 bucks to pay something else. We had to migrate later and it was a bunch of time and all that stuff. I never would have made that choice if we’d had a little more money in the bank. It’s the luxury of having some investment capital.
Mike: Yeah and unfortunately, you have to make a lot of trade-offs like that. You spend a lot of mental cycles and overhead making those trade-offs and just making the decisions because you don’t have the money, which is a crappy situation to be in. All that said, part of the problem is, you don’t necessarily want to raise money if the idea itself or the business model just simply doesn’t have merit. Maybe that’s partly what those investors are there for is to make sure that they act as something of a filter.
That’s always the problem that I’ve seen with angel investors is that they’re the ones who are in control, not you. Maybe angel investors isn’t the right word, but outside investment where they basically end up getting control of enough of it that you don’t get to make the decisions anymore. They’re the ones who make the decisions whether or not your business is going to succeed based on whether or not you get the money. If you can’t set aside the time, like nights and weekends, to be able to do it, it’s just not going to work out. You need that money in order to make the business work, then it’s going to be a problem for you down the road.
Rob: And that’s the thing is the losing control of your business tends to be if you raised multiple rounds because each round you sell, let’s say, 15%-20% is typical. May 15%-25% and if you do one round, you still have control. You and your co-founder or you if you’re a solo founder still own that 80%. But if you do another round, another right you get two, three rounds in, it’s typically by series C or D where the founders are the minority shareholder and investors now own most of it. If you don’t been on the path, it’s unlikely, or if you just make bad decisions.
I saw someone on Shark Tank where they had no money upfront and they sold 80% of their company to an investor, to an angel investor. Shark Tank was like, “We can’t fund you because you’re working for nothing.” All the work is for the investor. If you make a bad choice, that’s another way to do it too. You do need to educate yourself about it and I think that’s something that some people don’t want to do because it is boring stuff.
I really like the books that Brad Feld does and this one is maybe like venture funding or like a guide to venture funding. I got four chapters in and I just couldn’t stand it because it was all terms. He didn’t write it. It was more of a series that he’s involved in. The terms were just so boring that I stopped. I understand if you don’t want to learn at all. You need to learn enough about it to do it.
I want to flip back to something that Natalie Nagele responded to Justin Jackson and then it was actually just what I was thinking when I saw his graph. It was five years to $21,000 MRR. In all honesty dude, I would shut that business down before I wait it that long. I forget how long it took Drip but it was maybe a year. I don’t think it was even a year from when we launched and it was probably 12-18 months from when we broke around on code, that we had $21,000 MRR.
Drip was admittedly a bit of a Cinderella story. It was fast at growth than most but if you’re growing $100 a month in the beginning and you continue that 10% growth like that, you can’t do that. You need to get it up—
Mike: But I don’t think that’s a fair comparison, though, because if you look at the way Drip was funded into, you said 21 months or so to get to that point? He’s talking about a completed self-funded company versus something where you put money in from HitTail. Those are two entirely different things. I don’t know all about the details of Transistor but my guess is that there’s a huge disparity in terms of the amount of code and the quality of code that needs to go into something like Drip because of the sheer complexity of it versus something like Transistor.
Rob: Yeah, that’s true. I was for the long entrepreneurial journey too, I would say. I had successes that I’ve parlaid into it. You’re right. It’s not a fair comparison. I shouldn’t say with the Drip but…
Mike: I was just arguing about the point of, if it was five years to get to the $20,000 in MRR, should you shut that down? I think it’s a very different answer based on what it is that you’re putting into it. If you’re dumping $200,000 into it, yeah, you probably should shut it down if it’s still going to take you five years to get to that. But if you put nothing into it, or $10,000 into it but it takes five years to get there, it’s like, “Uh, well, I don’t know.” It’s a judgment call.
Rob: It’s interesting and that’s the thing. When I think back in 2005, I started with DotNetInvoice, making a couple of grand a month. It took me until late 2008 to get to where I was making about $100,000 a year, between $100,000-$120,000 a year and that’s when I stopped consulting.
So it took me three and a half years. But again, I did it with no funding and I cobbled it all together myself. That’s the situation we’re talking. I wasn’t doing SaaS. I did it with these multiple products. I think if I was less risk-averse, I’ve could’ve done it faster. I think that’s probably what we’re talking about here. It’s getting a little bit more ambitious and trying to speed things up. How do you do that?
Mike: Part of being more ambitious these days, I think, is because you’re forced to, because of the level of competition that’s out there. You have to do something that’s quite a bit above and beyond what you would have done three or five years ago because the competition is there and people are going to be asking for features that they see in other products that you’re trying to compete against. If you don’t have those features, they’re going to say, “Well, I could pay the same amount of money to you versus this other product and they’ve already got those features so why would I go with you?”
You’re just not able to compete unless you have those features there that you can demonstrate. It’s not even just about the marking. It’s about having the things they need. If you don’t have them, they can’t go with you. It’s not even that they like you. They just won’t do it.
Rob: Yeah and that’s true. Again, funding even the way we’re talking about it, it’s not going to fix all ills. If you pick those markets that’s too small or you don’t build a good product, you’re not going to get to action. Or if it’s a market that people aren’t interested, or you don’t know how to market, you don’t have the experience, you don’t suddenly become an expert startup founder just because you raise funding but if you have the chops and funding is a big piece.
Time is a big piece because you’re only working nights and weekends. You can only put 10 hours a weekend or rather 15 hours. It’s a big difference if you can suddenly go to 40 or 50 hours with two co-founders. It doesn’t fix everything. In addition, does it come with complexity? Yes. You have to report to your investors once a month with an email. You can feel the stress of that.
That was actually something that I asked Justin McGill, Jordan Gal, and Matt Goldman, those are the co-founders of those three businesses that I mentioned earlier, CartHook, LeadFuze, and Churn Buster, and I said, “Hey, do you feel raising this money made things more stressful or less stressful?” They each have their own take on it. If I recall, Justin McGill was like, “It’s more stressful because I feel like if we don’t grow, we’re going to let you guys down.” A lot of the investors he has a lot of respect for. That’s one way it cut through. It can make it more stressful.
I don’t want to put words in people’s mouths but I think Jordan had said, “It’s more stressful but better because it motivates him to succeed.” you got to think about how your personality is and if you feel like it’s going to add more stress, if suddenly five or 10 people that you really respect, that are friends, colleagues, and fellow Microconf attendees write a check to you, how does that make you feel?
Mike: Yeah. I think the answer’s going to be different for every person, especially depending on what your product is like, what the expectations are, how you’ve position it, and how the investor views it. Some investors just say, “Yeah, I may lose all this and that’s totally okay,” and other ones may say, “I have these expectations and you’re not meeting them,” if you miss a deadline or something like that.
There’s a lot of dynamics and complexity there. Some people will thrive in it and some people won’t. I think at the end of the day, I also feel having money has the potential to make the downsides of your product or business model worse. It will just exacerbate some of those issues. If you don’t have a market that you can actually go to, if you think you do but you don’t, and you get a bunch of money in, I think it’s just going to make it worse because yes, you can try a bunch of things and you’ll be able to throw money on it, but then you’re burning more money than you would have otherwise.
Rob: That’s the thing. I know we’re going long on time but really important. I would not raise any type of funding before I have product market fit. That’s a personal thing because (a) your valuation is way last before then, and (b) no one is going to give you money if you don’t have a product, period. You have to have a product these days. You can’t raise money on an idea unless you’re Rand Fishkin, or Jason Cohen, or a founder who’s been there and done that.
You have to have a product, you have to probably be live or at least have beta users, your should have paying customers. That’s a bare minimum to even think about trying to raise funding. You have to get there. You have to write the code, you have to beg, steal and, borrow to get someone to write the code. But the valuation is going to be way less and you’re probably going to burn though a lot of that money just trying to get to product market fit. From the time you launch until you’re part of market fit, I’m going to say it’s 6-12 months if you know what you’re doing.
You see founders like Shawn Ellis, you saw Jason Cohen, you saw me do a Drip. You see people who are pretty good at it and know what they’re doing, and it still takes them six months, and ours still takes 9-12 months to do it. At that point, once you do it and you do kick it in a little bit of that growth mode where it’s like, “Okay people, are really starting to uptick it.” That’s when you pour gasoline on the fire.
But before that, I have seen at least one startup in the last year raise a small round before product market fit, and just burned through it really fast because they staffed up, do a lot of marketing and do a lot of sales, and it just that their churn was so high. That’s typically where you can tell his people aren’t converting to pay it or they aren’t sticking around. There are dangers there. Like a samurai sword, like a said in the past, it’s a weapon that you need to know what you’re doing with to wield well and I think you need to be smart about when you raise.
Mike: Yeah and it sounds like there’s obviously different takes on it. If you want to go down like the VC or angel route, series A funding down the road, I think it’s possible to probably raise money if you have any sort of history or relationship with them, like if you don’t have a product yet. But you’re still also going to get eaten alive in terms of the equity shares and everything.
I think that point that you raised about you have to have a product and you have to have paying customers before you start to go raise money, that’s how you maintain your equity, a fair amount of the equity, enough of the control to be able to what you want, need to with the business, and also be reasonable sure and confident that you’re not going to just waste the investor’s money and burn those relationships. You can use that money for good, and you know what that money will do for you versus you’re still trying to get to product market fit. You don’t know who’s going to but it or who uses it, or why.
Rob: Yeah and the once exception as I’m thinking about it is if you raise a big chunk, let’s say you raise $250,000 or $500,000 and you feel like you need to spend it, and so you staff up but your not part of market fit, you’re going to treat their money. But the exception I can think of, is like I said earlier. What if you just bought yourself 12 months of time and you didn’t staff up but you just worked on it, or 18 months. You didn’t raise this huge amount of money or raise a small amount to just focus on it and work, I could see doing that before product market fit. That would get you to the point where then you can raise that next round.
I’m not trying to be wish-wash but I’m realizing I never said never raise before product market fit but I did say I wouldn’t personally. But I have the resources to get me to product market fit and I could work on a full-time to do that. It’s an exception. If was I doing it nights and weekends, then I would take money before I see I have to think about where the advice is coming from or where the thoughts are coming from. I’m just thinking it through as if I were literally doing this nights and weekends, I would consider taking money as soon as I could. If I was going down this road because going full-time is a game-changer. Being able to focus full-time, being able to leave everything behind is a big deal. It really is and a night and day difference.
Mike: I know there’ll be a range of opinions on it, but I wonder what most investors would think about, somebody saying, “Hey, we got this product. I’ve been working on it and I’d like to get some funding and money in the bank, basically to extend the runway because I got a little bit of something going here, I got partial product in place, I got some customers, but it’s not a lot. I need runway in order to make it work but I don’t know specifically how much runway I necessarily need or how I’m going to get to having $10,000-$20,000 MRR, but I need time to get there. There’s something here but I don’t know what.” I think it’s hard to evaluate for anybody what that looks like.
Rob: Yeah. I don’t know of any investors today that would work with that. I think that’s a good thing to bring up. It’s like, is that a gap in the market then? Could that be a successful funding model of looking at people who essentially have the potential and have, like you said, pre-product market fit but have something to show for it and looking at backing them for a period of time.
Anyway, I love this topic and I think that we’ll probably talking about it again, just soon you’ll be hearing more on it from me, but I feel we might need to wrap this one up today.
Mike: Yeah. Great talk. I like it.
Rob: Me as well. So if you have a question for us about this or any other topic, call our voicemail number 888-801-9690 or email us at email@example.com. Our theme music is an excerpt from We’re Outta Control by MoOt used under Creative Commons. Subscribe to us in iTunes by searching for startups and visit startupsfortherestofus.com for a full transcript of each and every episode. Thanks for listening and we’ll see you next time.
In this episode of Startups For The Rest Of Us, Rob and Mike talk about the 20 podcasts they listen to. They separate the podcasts into three categories, bootstrapping, startups/business, and off topic/entertainment.
Items mentioned in this episode:
- The Art of Product
- Build Your SaaS
- Bootstrapped Web
- Founder’s Journey
- Hooked on Product
- The Tropical MBA
- Indie Hackers
- This Week in Startups
- Stacking Benjamins
- Money For The Rest Of Us
- Planet Money
- Reply All
- Daily Tech Headlines
- Current Geek
- 99% Invisible
- System Mastery
Rob: In this episode of Startups For the Rest of Us, Mike and I talk about 20 podcasts we like. But first, I have a trivia question for you Mike. What color is Mace Windu’s lightsaber?
Mike: It’s purple isn’t it?
Rob: Nailed it. Nice. You are a Star Wars nerd, sir.
Mike: Thank you.
Rob: This is Startups For the Rest of Us episode 395. Welcome to Startups For the Rest of Us. The podcast that helps developers, designers, and entrepreneurs be awesome at building, launching, and growing software products, whether you’ve built your first product or you’re just thinking about it. I’m Rob.
Mike: And I’m Nerdy Mike.
Rob: And we’re here to share our experiences to help you avoid the same mistakes we’ve made. What’s the word this week, Nerdy Mike?
Mike: I almost got you laugh there. I almost got you to totally screw up.
Rob: You almost – to screw up the intro. The reason I ask that question is because A, I got it wrong when I came up on a trivia thing and both of my kids, my 11-year-old and 7-year-old, got it right. We’ve been watching the—I was going to say the Trilogy, but we’ve been watching Star Wars in machete order. So you go four five, two three, we’re about to hit six. I don’t know when we’re going to do Rogue One because it obviously fits between three and four, but you don’t want to watch it first because it’s not the early stuff.
Anyways, I’ve been immersed with Star Wars with the kids for the past couple of weeks. My 11-year-old is rewatching but the seven’s are basically seeing them for the first time. It’s been cool. It’s always fun to watch Star Wars with someone for the first time when they’re enjoying it. But aside from that, what’s going on with you?
Mike: Not much. I’ve got a couple of announcements to make. The first one is about Microcomp Europe. We’re going to be making some announcements in the next couple of weeks about when MicroConf Europe is going to be coming. If you want to hear more about that, make sure that you’re on the mailing list or you can go over to microconfeurope.com. Enter in your email address into the mailing list and if you’re not already added, you’ll be added into there. When you make the announcements in a couple of weeks, you’ll get the emails and start planning accordingly. We’re hoping to have the final location and dates nailed down hopefully in the next two weeks or so, but it’s just taking a little bit more time than we expected.
Rob: It always depends. It’s hard to find the right hotel in the right country on the right dates that don’t conflict with some major, major other event whether it’s another conference or a national holiday or something.
Mike: The other announcement is for MicroConf 2019, which will be in March of next year from the 24th to the 28th. The 24th, 25th, and 26th, that’s Sunday, Monday, Tuesday, that will be growth edition. Tuesday, Wednesday, Thursday is going to be starter editions, so the 26th, 27th, and 28th will be starter edition.
Rob: I’m deleting them all. I’m not even reading them. It’s irritating.
Rob: Hey, everybody, look at this. I’m not doing that.
Mike: It’s ridiculous.
Rob: Yes. Now that I’m seeing it, we’ve talked about that on the show a lot from the kind of company perspective, or the owner, the founder perspective. But now I’m seeing from the consumer perspective, and I hate it already. It’s annoying. People check in the box because they got to check the box.
Mike: Which is interesting because I also see emails from people who are talking about GDPR and it’s clear from the emails that they don’t completely understand what it is that they’re supposed to be doing. I’ve seen all these email coming through. There’s a general trend or thread that you can see, and someone is wrong. I’m not saying I’ve done the research to figure out exactly, and in certain situations whether the vast majority of people are right or the vast majority of the people are wrong, but there’s definitely variations between what some people are doing versus others. I don’t know. It’s totally screwed up and there’s no good answer for it.
Rob: Yes, for sure. On a lighter note, I had mentioned my brother was in town last week. When we were kids, we played obviously, the original Nintendo, the NAS. We played the SEGA Genesis System. He bought it when he was in college. This was the one with Sonic, Altered Beast, and some of those early SEGA classics. Once they got ahead of Nintendo if I recall, and this was the console that—they eventually lost the battle. There’s a good book about this. I wasn’t sure I figure out what the name of it is but it tells the inside story of all that.
When MicroConf Vegas is here, we gave away some of these classic consoles where you spend—it’s between $40-$100 and you can get an SNAS, or an NAS, or a SEGA Genesis System, and it comes with the games built in right on some hard drive. I noticed the SEGA Genesis was $40 on Amazon, so I just bought it while he’s in town, and I’m probably going to sell it on Amazon as a used console here in the next few weeks because I don’t really want to keep it. We had a blast, man.
We hung out a couple of the nights he was here. Just drank some whiskey and played Altered Beast and all the old games you remember from that era for hours and hours.
One thing I was disappointed with, the console’s fine. It’s pretty cheaply made. It’s not made by SEGA. It’s made by some third party and they threw on a bunch of games. They say it has 81 games but it’s really like 40 SEGA games and then 40 games that this company made in the past 10 years that are kind of garbage, so you don’t even play those. But what I did notice is that games like Altered Beast, and there’s couple of adventure games you used to be able to on the original SEGA continue forever and that’s how you would win it. You would just keep hitting start and you had infinite credits, but on this classic console, you don’t. You have two or three credits and once you’re done with it, you’re done.
It took all of the fun out of it because we couldn’t win any of the games. It’s pretty hard to do, but be we just aren’t in our peak chops for these games.
Mike: You’re losers.
Rob: I know. It’s funny though to realize that, “Oh, this isn’t,” I’m like tempted to go buy a real console. The old console you see them on eBay for $20 or $30, get the actual cartridge then you know that you’ll get the original experience. It’s just a bummer that they modified the original experience. I guess that’s how I feel. Why would they do that? Why would they change it from the way it was in the 90s.
Mike: I don’t know. It’s funny you’ve mentioned Altered Beast a couple of times, but I remember in college, there was a contest at the arcade at college where you could win the full version or the stand up version of the Altered Beast game, the arcade version. All you had to do is you had to get the highest score in a certain month. I went down there with a couple of dollars and a friend of mine, and ended up getting the high score and won it for—I spent less than $10 trying to win it.
Rob: That’s crazy for you. Few weeks ago, we had a question from a listener asking what podcasts we are listening to, and every so often, we do this. We probably do it once a year but we do it probably once every 18 months to 24 months because this change, I know it changes for me pretty frequently and it depends on the phase of the product I’m in, or the phase of the business. I know once we sold Drip, I just couldn’t listen to all the growth hacks anymore. It kind of killed me because I wasn’t in the midst of that anymore, so I had to just weed myself off of those.
Depending on what phase you’re at, it depends on what you don’t want to listen to. We picked our top 20 podcasts. We just grouped them into three different areas. We have the bootstrapping crew, we have the startups/business area, and we have off topic. We’re just going to run through these 20 and we’ll list them in the show notes as well. These are what I consider the highest quality and most relevant to our listeners.
There’s certainly some podcasts I listen to that are really infrequent and we exclude them from here. I also listen to a bunch of podcasts about tabletop gaming or role-playing games. Well, we could mention those. It’s probably not interesting to the majority of folks listening, so we won’t cover those. In no particular order, because we just went to our podcast feeds and send them in.
The first product is The Art of Product, and this obviously my Drip co-founder, Derrick, and Ben Orenstein who’s been a MicroConf speaker. They put together a really tight show where they just talk through the updates from the other person, what they’ve been doing in the last week and they’ve gone from—Derrick is working at Drip and Ben had a full time job. Ben went out on his own and did info products. Derrick left Drip and Ben got a full time job and they swapped. Then Ben left and he’s now doing a startup and Derrick’s doing his startup. Really interesting conversation from two smart people who are discussing topics that would be highly relevant to you as a listener of Startups For the Rest of Us.
Mike: The next one on the list is Bootstrapped Web from Brian Castle and Jordan Gal. Brian Castle runs Audience Ops. Jordan runs CartHook, and I think you’re an investor in CartHook as well, right?
Mike: Those two have some really interesting stuff that they talk about. For obvious reasons, they don’t talk about everything that’s going on in their businesses, but it is a fascinating look at the stuff that they are working on. I really like hearing them talk about the stuff that they’re doing and the challenges they’ve run into. There’s just some fascinating topics that come up. Sometimes it’s just not even directly relevant to their business, or about technology, or marketing itself. Sometimes it’s just people management. How do you deal with different situations that come up, or how do you negotiate, or how do you solve a particular problem that was not your own like if somebody got dumped on your lap from some other vendor or partner of yours. How do you move forward from that? How do you recover from a fiasco that is largely out of your control.
Both of them are super sharp guys. I really like listening to them and hearing about it, and then just reconnecting with them. I used to work at MicroConf and Brian also runs a big Snowtime in Conf, so I usually see him when I go to that and it’s a winner as well.
Rob: I’ve been a long time listener of their podcast. I’ve been on on a couple of times, two or three times talking about stuff. Really, can’t recommend it enough. Again, heavy overlap in terms of concepts, topics, and really goals of what you and I espouse on this podcast.
Another podcast, I just recently started listening to it actually, is called Build Your SaaS, and it’s Justin Jackson and his co-founder of Transistor.fm, which is a podcast hosting company. It’s cool. It’s early stage stuff. They’re talking about their pricing. They’re talking about funding versus not and just talking about the two sides of it. I think it’s a fun romp. It’s always fun to hear Justin’s energy on their podcast and they do a good job with it.
Mike: Next one the the list id Rogue Startups from Dave Rodenbaugh and Craig Hewitt. Both of these guys have been long time MicroConf attendees. Craig used to headspoke at MicroConf Europe. I believe it was last year. Dave Rodenbaugh has given an attendee talk at MicroConf in Vegas as well. Dave has transitioned over the years from running just a series of WordPress businesses over onto his SaaS called Recapture. Craig Hewitt has been running Podcast Motor for a long time and he’s starting to branch out into other types of products in the podcasting space.
It’s just interesting hearing the journey over time and the different perspectives that they both bring to the table, partly because Craig moved over to Europe. He lives in France at this point. He Brought his family and two young kids over there. Some of the conversations talk about what it’s like to bring them over, and the differences in the school systems, and the challenges associated with going back and forth as a family, and how to integrate into the local culture and essentially run the business as a location independent business.
Rob: I’ve been a long time listener of Rogue Startups as well and a fan. Dave has multiple WordPress plugins, as well as Recapture.io, which is a small SaaS up he acquired. Craig Hewitt is running a couple of things but really past those is what I know he really focuses a lot of his time on which is podcast hosting. It’s kind of fun to hear their trials, tribulations, victories, and defeats, much in line with the stuff we talk about here.
Next podcast that I’ve enjoyed is Founder’s Journey, and this is from Josh Pigford at Baremetrics. He basically reads his blog post which I enjoy because I don’t read many blogs anymore. Really, I don’t read any blogs. I actually like that I’m able to kind of keep up with his thoughts on entrepreneurship and renting a relatively small startup without having to read text. I can do it while I’m running or riding my bike. It’s cool. It doesn’t have a regular publishing schedule but it’s short. When it comes out, it’s like 10 minutes. Since it is packing a blog post into that 10 minutes, it’s very compact. It feels like a 30-minute episode packed into 10 minutes, which is something I enjoy about it.
Mike: Next one on our list is the Tropical MBA from Dan and Ian. This is probably the single podcast I’ve listened to the longest. I’ve started to listen to it very early on when it came out. I’ve been listening to it for seven or eight years at this point. They have actually more episodes than Startups For the Rest of Us.
Rob: That is unfair.
Mike: I know. I think the thing that strikes me as interesting is that it feels to me like they’ve been on a parallel path with us, or we’ve been on a parallel path with them. Only they were aimed mainly at location independent entrepreneurs versus we focus much more on software entrepreneurs. Their ethos, ideas, and approach towards business really feels like it very much aligns with us. I think that’s why I’ve felt like it resonated so much with me. Dan and Ian had spoken at MicroConf in Europe. It was either 2013 or 2014, I forgot. It was in Prague. It was great to have them up there.
It was the only time we’ve ever had two people give a talk at MicroConf and it was fantastic. They fed off of each other really well and it looked like they rehearsed the entire thing. I imagine that they probably didn’t just because they have that natural interaction between each other that works really, really well. I think that’s part of why I like the podcast so much.
Rob: I’m with you. I’ve started listening really early on. I describe Tropical MBA as our sister podcast. I say that all the time. I feel like we’re two siblings, you know, they say sister cities, that kind of feels the same but in different places. It’s very similar in terms of, like you said, the ethos because it’s about building a life that you want and building a business to help you do that.
Their early focus was on location independence. They were in Bali, the Philippines, and other areas of the world, and you and I are on a different situation. We already had wives and kids when we started this podcast, and so we didn’t talk about the travel aspect of it, but we’re all talking about building a business to help you build a better life. I agree. I really can’t recommend Tropical MBA highly enough and as you mentioned, it’s one of the very few podcasts that has more episodes than we do.
Mike: I think they’re also one of the few people who’s taken over the Startups For the Rest of Us podcast as well. Do you remember the episode—it was the April 1st episode. We let them take over Startups For the Rest of Us and we took over the Tropical MBA for that one day. I think the only other time was when we had our wives come on and do the episode instead.
Rob: That’s right. We need to do another one of those at some point.
Mike: Yes, definitely.
Rob: That was fun. Cool. Our next podcast is a newer one. I think they only have 10 or 11 episodes. It’s called Hooked on Products, and it’s from Phil Derksen and John Turner. Also folks we’ve met through MicroConf long time, actually long time Micro Academy FounderCafe members. They’re hustling, they’re WordPress plugins, they’ve both gone independent at this point after a few years of building and acquiring products. It’s fun to listen to their interviews. Their origin stories are pretty cool. They just released how each of them got to where they are, and that is always fun for me to hear folks talk about that, because the founder’s story, it kind of never gets old hearing how founders got to where they are today.
Mike: The last podcast in our bootstrapping category is Indie Hackers which is run by Courtland Allen who does all the speaking and interviews, and then his brother Channing Allen does all the backend stuff for Indie Hackers. I find this fascinating just because he talks to people that are very early stage all the way up to they’ve sold their business and maybe they made millions of dollars from it.
You get this broad spectrum of people who are building profitable businesses, and you hear about the trials, the tribulations, and the things that have gone really well. You also hear about the things that did not go so well and the mistakes made along the way. I just love hearing that. All the different stories and things that people have run into, because if you’re working on your own business, you have this one view of the world and of your own business, but you don’t necessarily get that perspective that other people might have.
Hearing all those different stories gives you that perspective and makes you think about things that you might not otherwise have thought about that relate to your own business. Did you notice, by the way, in our bootstrapping section, every single person on this list who has those podcasts, all of them have been to MicroConf?
Rob: I know. I know, as we were saying this, I was like, “That’s interesting.” I don’t know why that is. I don’t know if it’s because we know them, I’m more interested in listening to their podcast, or if just people who are going to start a podcast in the space are naturally going to gravitate towards our community because it is their people in essence.
Mike: I don’t know. I’d have to think about that a little bit more, but I just find it interesting and looking at the list afterwards like, “Huh, every single person here, I’ve met them at MicroConf.”
Rob: Yes, that’s cool. Our next category is the startups/business category and this is podcasts that are focused on bootstrapping but they are still relevant to folks who listen to Startups For the Rest of Us.
The first is, if you’re not tired of hearing me every week on Startups For the Rest of Us, you should check out ZenFounder. It’s the other podcast that I co-host. I co-host this one with my wife, Dr. Sherry Walling, who is a clinical psychologist, and I think we’ve been doing this I think three, three and a half years now. It’s crazy to hear that it’s that long because I think we’re on episode in the 150, 160 range. It’s some really good stuff. The Founder Origin Stories have been a big hit where we’ve interviewed founders. Sherry doesn’t jus interview them about how they got there in their business but in their life. Like growing up, all the adversity they faced, how they got to where they are, and there are some amazing stories about folks who were in jail, folks who were almost killed, folks who lost parents, and about how that impacted who they are as a founder. ZenFounder.com or ZenFounder on iTunes if you haven’t checked about it. There are some good stuff coming out of there.
Mike: I definitely recommend ZenFounder as well. It’s been three years. I think it came out in 2015 and I still listen to it all the time. It’s one of those other ones that’s kind of made it into the—I use the app called Cast and it’s in the category called My Top Podcasts, which basically those at the front of the list out of all the other ones that I subscribe to.
Rob: Well, that’s cool. Thanks for the endorsement, sir.
Mike: the next one on our list is This Week in Startups. I started listening to this a while ago. This is run by Jason Calcanis. If you’re not familiar with him, he does a lot of angel investing and talks about startups in the Silicon Valley area. I found that I didn’t necessarily resonate with a lot of the things that were said, but I felt like I needed to be at least aware of the things that were going on. It’s not like being in the Valley is something that I’m really particularly interested in. I don’t want to go out and raise millions of dollars, but I also feel that I shouldn’t be completely ignorant of the things that go on and the types of stories that come out of those.
Obviously, funding works for some people and it doesn’t work for others. I can’t say that I would take that swing for the friends’ approach right now just because of the situation that I’m in, but I can certainly appreciate the value of raising a lot of money and doing something where you wouldn’t be able to do that without that funding, but not everybody can take those chances.
Some of the things that they talk about, I don’t necessarily agree with, but Jason’s definitely got a say something of an over the top attitude about—attitude probably is not the right word, but approach, I’ll say towards business. You should definitely do this. I think it’s just more of him being an extrovert than me being uncomfortable being an introvert.
Rob: Sure. Yes, he’s definitely opinionated. He’s a really smart guy and hard working as well. He kind of pulled himself up by his bootstraps from a very working class family. At first when I listened to it years ago, I was so irritated. I thought he was obnoxious and now, I realize he’s a smart dude who worked his ass off his whole life. I’ve come to respect his opinions. I find that I agree with him more often than not now. Not sure that I did the entire time that I listen to it, but when I disagree with him I can at least say, “Yeah, we just disagree and we see things differently,” kind of in my head. He has such a unique take on a lot of topics. That’s what I like to see. He kind of challenges some of my thinking and some of his guests do, as well.
There’s a really good episode, probably my top three episodes of this podcast are when he interviewed David Heinemeier Hansson, and they talked about funding and they go toe-to-toe, because DHH is very adamant one way and Calcanis really was just like, “Here are examples where that just wouldn’t have worked period.” I actually felt like Calcanis won the discussion. He had really good points about it.
The other one, I liked, Joel Spolsky, he’s been on there once or twice which was always fun because I’ve followed Joel for so long. And then, Chris Sacca did a two-part where he talked about all kinds of stuff. That’s what I like because I never would have followed or even been aware of Chris Sacca, but hearing Calcanis interview him made me think about things in a way that I have never done before. It kind of expanded my horizons.
That’s what I look for in This Week in Startups. I agree with you, a lot of the stuff on there. There’ll be interviews with someone doing some drones startup and I skipped those. I delete those because I just don’t have that much interest. But the news roundtable’s keeping me somewhat in touch with a world that, you’re right, is not our world because it’s more of the Silicon Valley startup, but it is tangentially related.
It’s certainly not a sister podcast, but maybe it’s like a second cousin. There’s something out there that I think is important for us to be abreast of given that we’re in technology.
Mike: It’s the long lost Uncle Joe who comes over and gets drunk and causes a raucous. If we’re talking family relationships, that’s probably it. I think your description of him of being opinionated is probably the one that is most in line with what I was thinking. I couldn’t come up with the right word, the right phrase, and also place the right amount of respect on him, it’s opinionated, it’s definitely it.
He does things and says stuff that I wouldn’t necessarily do myself but I can certainly appreciate the value of going through those steps towards building a business or putting your startup out there. I’m not going to say that it’s for me but that’s partly because, like I said, I’m an introvert and it’s just not for me. It’s not that it’s wrong, it’s just I wouldn’t probably approach it that way.
Rob: Right. And when we say opinionated, that’s not a negative thing. It just what it is. He has strong opinions and sometimes it can come off negative, but other times it’s like, “Wow, he’s really taking a stand here.” I appreciate that and respect that. Again. More often than not, I think he’s on the right track with what he’s thinking.
Our next podcast is really purely for entertainment so I debated whether to put it on here, but it’s kind of like you got to give a nod to Alex Blumberg. It’s StartUp and it is on Gimlet Media. It was Alex Blumberg’s podcast, but essentially, he left This American Life to do StartUp. The first season or two were phenomenal. The most recent seasons, two or three seasons have been less so. They’re interesting but they’re just following stories of stuff.
It’s like Planet Money for startups, but I struggle a little bit with the lack of reality. If you think This Week in Startups interviews a lot of people just raising $20 million, $30 million, at least that is actually happening. A lot of stuff Alex was looking at on the first couple of seasons at StartUp were such a beginner view of things which, I hate to say it that way, it sounds pejorative like I’m saying you should never be a beginner. But it sounds like it never examined the possibility of that bootstrapping or a small angel round is a totally viable option for most businesses. Maybe he wasn’t able to do that but it was never brought up.
It was kind of presented as, “Hey, if you want to start a company, you raise funds.” That really has been the message at the entire time. I don’t love that about it, and frankly I should probably write in or send something just to be like, “Hey, this is another take on it,” but all that to say, it’s entertaining and worth listening to, but I don’t think you can take any business lessons away from it.
Mike: I’m with you on that. I’ve felt the same way about it being and again, you used a phrase and you said, I don’t want to be pejorative about calling it very beginner focused or having that beginner view, because everybody’s got to start somewhere, but it felt like there was no research done to say what are the options here? It was just like, “Hey, go raise funding. This is what will make your business successful.” I don’t know. I listened to it for a while. I haven’t listened to the StartUp in quite some time actually, probably at least a year or so.
Rob: I don’t even remember what the prior season was. There’s one coming out right now that’s fine, but the one before it was okay. I don’t think you’re missing that much. Our last podcast for startups/business is Akimbo, it’s Seth Godin’s podcast. He had said for years he wasn’t doing a podcast because he just didn’t have the time. He has to be really choosy about his projects but he’s doing a podcast now. It comes out every week and he talks about a lot of stuff you’ve heard from him in his books and his talks and such, it’s solid. It’s not blowing my mind because I’ve heard a lot of this from him before because I’ve followed him for years.
I often find that he’s talking about a trend or an idea that I don’t know what to do with. All right, so you have a dip. So what? You know, there’s not enough detail or like, “Okay, culture changes and here’s how it is.” And it’s like, “Okay, so then what do I do with that?” That’s always been my struggle, but at the same time, Seth is a genius and Seth, he sees trends that others of us don’t see. He thinks and he talks about things in a way that most of us do not. I like it because it expands my mind and helps me think about things in a new way.
Mike: Bonus podcast here would also be Seth Godin’s Startup School. That’s a 15 episode podcast. He did it in the past. I think back in 2013 or so. It was an interesting look at the journey of entrepreneurship and all the different things that you could and should be thinking about when you’re trying to build a business. I think it was based off of—didn’t they have a group of people that went through, it was kind of a classroom or a little startup school as he put it, where they put people through this program and a lot of the things that come out of that, or clips from Q&A sessions with the people that were in there.
It’s fascinating to hear the types of questions that they come up with and then his off the cuff answers. Obviously, everything is edited, but still as you said, Seth’s a genius. He sees things that other people don’t and a lot of times, it’s stuff that is even just on the fly he sees it. It’s fascinating to kind of watch him work through something and bring you to a logical conclusion that is also correct and astounding that he came up with it on the spot.
Rob: And like you said, it was 15 episodes and it was done. It was back in 2013. It’s still on iTunes and you can listen to it. I should probably listen to it again because it’s been a few years, but I thought that was really well done.
So now we’re going to dive into our off topic podcast and we have a handful of them, seven or eight. These are things that we like to dig in to. The kind of nerdy pursuits or just edification. I listen to a number of personal finance investing podcasts because it’s always been a hobby. One all throughout there is called Stacking Benjamins, comes out three times a week. It’s got a big audience. They make it entertaining and kind of fun to think about. They look at the headlines. They interview somebody, and they have a discussion, and some trivia and stuff. If you’re into that kind of topic, if it’s a hobby, I think you should check it out and even if not, you can probably learn something about saving for retirement and some money tips and such.
Mike: The next one on the list is Planet Money. I got into this, I forgot how I ended up finding this one, but it’s an NPR podcast. They talk about all these different things related to money, whether it’s a class action lawsuits about civil rights cases, or they have one on called The Less Deadly Catch. The podcast traverses a lot of different business types, whether it’s the vodka industry, or Valentine’s Day, or Super Bowl, they look at money topics related to all different types of businesses, and they drill in specifically into particular problems.
Mostly episodes are pretty short. They’re anywhere between 15 and 25 minutes long. Some of them are a little bit longer than that. They talk about issues related to either having money available or how businesses make money, or things that you wouldn’t necessarily think are obvious. And because it’s an NPR podcast, they have the ability to do some investigative journalism and drill in to things that you would not normally learn about. They’ll send a reporter out to do interviews and find out information and they’ll interview people on the podcast.
Essentially, I find it just educational because there’s lots of business types that I’m not aware of. We’re in the SaaS industry or software industry, and you’ll hear about these things that, I think on the last episode they talked a little bit about Tree House Brewery near where I live and it’s a fascinating business model, but had I not been there, I would not have heard about it, but with Planet Money, you get to hear about those types of things.
Rob: Yes, and Planet Money is a spinoff of This American Life. They did that during a financial crisis. They did maybe a two-parter on what happened trying to unravel and explain, and it was so popular they decided to form an entire podcast and that’s when it started.
Mike: Got it. Yes, that must be where I heard it from.
Rob: My next podcast is another investing podcast. It’s called Money For The Rest of Us. Actually, when I stumbled upon it, I was emailed the guy, David Stein. I was like, “Hey, I run a podcast with a similar name.” He’s like, “I had no idea your podcast was out.” Because we were earlier, right? We’ve been since 2010 or 2011, and then I think his is maybe three years old. He’s like, “I’m so sorry. I hope you don’t feel like I took your thing.” He said he just came up with it out of his own head, so no hurt feelings.
If you go into iTunes and search for the rest of us, you’ll see buckets of podcasts with that name, so it’s not like something we own the trademark on it.
Mike: We don’t have a license to it. We did not trademark that.
Mike: That’s like a big mistake.
Rob: Exactly. But J, David Stein was an institutional money manager. He would advise these endowments and he would help them like colleges and universities. I think it was non-profits only and he would help just manage their money and keep the assets allocated. What I like about him is he’s super even keeled. He’s not sensationalist. He’s not saying, “Buy, buy, buy, sell, sell,” It’s all about asset allocation and big buckets. He’s very calculated and looks at a lot of indicators.
He says he invests at the leading edge of the present. He’s like, “I’m not guessing where the economy is going,” but he does move money in and out of these big asset classes based on, he sees that emerging markets are way overvalued and he’s probably going to eke a little money out of that. He’s pulled money out of that asset. He’s not trying to time the market per se, but like he said, he does at the leading edge of the present, so very smart guy.
The main podcast is good. It’s evergreen content. I don’t get a ton of value out of it. It’s just stuff to think about. His Money For The Rest of Us Plus which is the one you pay for, and it’s very inexpensive. I think it’s probably $20 a month or something like that, or $199 a year. It’s in that rance. In my opinion, is one of the most underpriced things that I pay for. I hope he’s not listening to this, but he could multiply the price by five and I would still pay for it because he gives his take on where the economy is. And it’s not just him making things up, he looks at PMI and all these data sources that he used as a professional money manager. It helps me think through, as I’m moving money in and out of things. I don’t necessarily do the exact thing that he’s doing but at least I have the context for it.
To me it’s more valuable than if I were to pay a money manager to actually be managing my money. He’s giving just tons of really solid information. In the financial investing space, he’s one of the people that I respect most.
Mike: You know what he should do is multiply his price by five and then grandfather people in. That should be your advice to him.
Rob: That should be as long as I get grandfathered, totally.
Mike: The next one on our list is The Daily Tech News. There’s also a spinoff of this to which I hadn’t actually been aware of that you had mentioned to me, which is called Daily Tech Headlines, which is a much shortened version of it. The Daily Tech Headlines is just the headlines themselves. The Daily Tech News Show, they go into the detail on each of the different headlines. I find that a lot of the discussions from The Daily Tech News Show very fascinating.
They have different people who come on and Tom Merritt kind of runs the show for the most part, and there’s different people that he brings on to have discussions about different topics on different days of the week. It comes out every single day. It is somewhat difficult to keep up with all the different discussions, but The Daily Tech Headlines is probably a better place if you just want to hear the headlines, and if you want to drill into those and hear a lot more detail about them, then you can go to The Daily Tech News Show.
Rob: The Daily Tech News Show is what, like 20-30 minutes?
Rob: And The Daily Tech Headlines is four or five, and that’s why I switched. It is five days a week. I couldn’t keep up with the full discussion and I just backed off to the headlines and I’ve really enjoyed doing that. I’m the biggest fan of Tom Merritt. I respect the heck out of him as someone who just, he has opinions but he’s willing to have conversations about them. He’s very well-informed. He doesn’t make rash comments or extremist things in either direction. He’s always pretty even keeled and that’s what I respect about him. He worked with Leo Laporte at TWiT and then left to do his own thing with Daily Tech News Show.
Mike: I always liked how he can see both sides of the argument whether it’s talking about self-driving cars, for example, and what are the moral implications of those things. Not just around the classical question of who do you kill if there’s a mother and a baby in front of you and some construction workers to the side. The car is going to have to choose somebody, who do you choose? He can talk to those things but he can also talk about the fact that these self-driving cars are going to be putting people out of work, truck drivers, for example. And what are the implications of that not just on the economy but the moral implications moving forward.
He’s got very broad view. Like you said, I just respect his opinions on it and him being able to listen to those things and talk about them without necessarily coming down very hand-fisted on a particular point of view.
Rob: One of Tom Merritt’s other podcast that I enjoy is called CurrentGeek. It’s a weekly podcast that they used to do every week. We’ll look at the current weekend geek news, movies, and the light tech stuff. They recently, I think it’s every other week they do that, and now they’re watching some movies, some classic movies and talking about them which is still interesting. When I first heard that they were doing that, I was like, “Oh, no.” Tom and his co-hosts are so entertaining to listen to that I listen to those episodes as well, and then we’re going back and watching pilot episodes of things. They did pilot episodes of Lost in Space. They did Lost. They did Breaking Bad, and Seinfeld. It’s funny to hear them talk through. They do research on it and then they talk about the changes, and what went down. They don’t just talk about the show itself but a lot of the behind the scenes which is fun.
Mike: Next one on our off topic list is 99% invisible. I like this one because it doesn’t tell me anything about startups, or business, or anything like that, but it gives you insight on just interesting stories that you would otherwise have no idea that those things existed, or that somebody had even thought of them. One episode that sticks out of my mind is one where they talked about how buildings are made specifically for high rise buildings, hotels, and things like that. Like if you go to the stairwells, for example, they tend to be just like a giant cinder block. It’s almost like a chimney and their stairs metal is very barren. Almost every hotel that you go into, when you fo to the stairway, there’s nothing there. It doesn’t look pretty in any way, shape, or form. The reason is because they use those as fire escapes because they learned year and years ago that when buildings start to burn down, people need to get out. If those areas of the building catch on fire, people can’t get out. There’s building codes in place that they talked about. They just talk specifically about why those buildings are designed that way and structured that way, and it’s to clue you in. It’s just to help those people get out. Those are the last things of the building that will burn up giving people the most time to get out.
And then, there’s other things. There’s stairs that go nowhere that they’ll talk about or statues in a particular city. Again. It’s the things that you would not otherwise have any idea that they existed except for this podcast, goes out and drills into those things and talks about them. It’s just interesting stories. I use it for more entertainment value than anything else. It’s definitely one to check out if you’ve got some time. The episodes are very well done and very well researched.
Rob: Yes, that’s the thing. It’s an NPR podcast and it’s really well done. The title comes from, like you said, it’s things that most of us don’t think about. They’re kind of invisible to us.
Last three podcasts, I’ll run through quickly, really to do with an honorable mention. The first one is another Gimlet Media podcast called Reply All. I just heard an episode after StartUp at one point, recommended it and I’ve been really impressed with the hosts and the production value of it. It’s a podcast about—I cannot compare it to something.
It’s at a production level of a Planet Money or This American Life, but it’s dealing with more Internet, online stuff, online trends, and memes, and that kind of stuff in a pretty cool and interesting way.
The next podcast is Clay Collins’ podcast about cryptocurrency. It’s called The Flippening. He interview big players. He knows a bunch of the people in the space. It’s interesting to hear him talk to people who are pushing that whole space forward. If you’re already hearing about it, then you may want to avoid this one, but I think that Clay really has his finger on the pulse of where crypto is headed and I do believe that it’s around for long term.
The last one I just added, we we’re talking because I realized, the funniest podcast I listen to is called System Mastery. It’s vulgar as all heck. These two guys are cracking jokes. They will, week to week, I think the main feed is them reviewing old and even new roleplaying game manuals. They read through them and they talk about how the roles are good here and how they’re dumb here, but then they have all these feeds that they’ve combined into one. I hear System Mastery, which is them reviewing these role-playing systems. They also talk about, they do Expounded Universe where they read Star Wars expanded universe novels and they make fun of them because a lot of them are poorly written. They watch movies, which I think is called Movie Mastery. What’s funny is, I would say they make fun of them but they do it—when the movie’s good, they don’t just make fun of it. They talk about how much they like it, but they still do it in a humorous way.
For some reason, I have all that in one feed and I don’t know if that’s because I support them via Patreon or not. It’s either going to be your speed or it’s not because they use a lot of foul language but it’s also really funny. It’s funny if you’re a nerd and you get all their references because they make some deep, deep references. I really like what they’re putting together. I think most of it is improve, which is pretty impressive.
Those are our 20 or 21 podcast that we are liking these days.
Mike: I think that about wraps us up for the day. If you have a question for us, you can call it into our voice mail number, 1-888-801-9690, or you can email it to us at firstname.lastname@example.org. Our theme music is an excerpt from “We’re Out of Control by MoOt” used under Creative Commons. Subscribe to us on iTunes by searching for startups, and visit startupsfortherestofus.com for full transcript of each episode. Thanks for listening and we’ll see you next time.
Rob: Before we go, if you have a podcast you feel like should have made our list, please either email it in or post it to the comments of this episode, episode 395.
Mike: Rob, the interesting thing about recording this episode on the top 20 podcasts that we like is that, I actually stopped listening to podcasts about a month and a half ago.
Rob: Did you? You’re just cold turkey, just all of them.
Mike: It was mainly because what I realized was that as I would listen to podcasts when I was mowing the lawn, or when I was driving, or when I was going to the gym, what I realized was that it made me feel for the most part like I was still working. It just extended my workday especially with any of the podcasts that were about business, startups or anything like that. It just made me feel like I was working all the time.
Rob: Yes, because you’re thinking about work all the time. That makes a lot of sense. I’m glad I didn’t title the episode 20 podcasts we listen to. Podcast we like is accurate, right?
Mike: We, as in you.
Rob: Exactly. My guess is you’ll come back to them at some point, but I hear you. I don’t think that’s a bad thing to do for a season. I certainly have gone through spells where I have cut. I used to listen to 55 podcasts, not all of them get on every week, or whatever I called it way down. I was down to 10, and it was stuff like Daily Tech News Show that didn’t make me feel like I was working because it was more about entertainment and news. I had almost nothing in the startup space and then slowly, I kind of worked my way back into doing that. I think there’s a case to be made for both directions. I think you can swing too far with constantly shoving information in your head and not giving yourself space to feel like you can relax.
Mike: I think it’s also the ability to take a step back. I’ve noticed this in certain situations or certain times of the year where I will be heads down working and not really come up and look at the landscape from a broader perspective or a strategic view of things. If you’re always implementing things, you’re always working in the business, then you’re never necessarily doing the planning stages and looking at the big picture. The problem is I felt like I was getting too far into the weez with all the mechanics and the tactics, things like that, but never actually taking that step back to do any strategy and look at the bigger picture.
Rob: I agree. I think that you need quiet time to be able to do that. If you are busy, because you’re busy with your business, you’re helping with your wife’s business, watching the kids, doing all the stuff you have to do, if you don’t have time during the day to sit back and just think, I don’t disagree that dishwashing, mowing the lawn couldn’t be that time.
These days, I have time during my days now to do that. I’m sitting thinking during the day, so when I am doing dishes or mowing the lawn, I don’t want to keep thinking about stuff. I’m already doing some big picture thinking, so I think it’s kind of a phase you’re in.
The other thing too is a lot of podcasts, they aren’t that constructive. They aren’t necessarily pushing your thoughts or your business forward, whereas audiobooks could be. You can listen to fiction to make yourself feel like you’re really not working. Or some folks I know just go away from podcast and go audiobooks only because they an information dense resource.
Mike: That’s a big difference between something like an audiobook versus a podcast, whereas a podcast is much less directed and focused on a particular thing. You can get an idea of what a podcast is about from the title or from the description, but that doesn’t necessarily mean that it’s going to be helpful to you versus a book, where if you buy a book about a very particular topic like sales strategies, or how to use Facebook ads or something like that, it’s going to be very focused on that one thing that you intentionally and deliberately decided that you are going to learn more about versus a podcast, where you might pick up some things and you might not, but it’s probably not going to be terribly actionable versus something like a book or an instruction manual.
Rob: That totally makes sense.
Mike: The other thing is it kind of makes me think about the conversations we had on a podcast about the consumption versus production modes between people. Should we be making things or consuming, it’s hard to do both at the same time. Right now, I’m producing stuff so it’s hard for me to consume stuff at the same time. It just makes my brain go sideways a little bit I guess.
Rob: Big time. I put up a blog post at one point. It was producer versus consumer or something like that. If you Google that, you can find it. There’s a really good comment thread after I published it. It was a good conversation about this. What I proposed there, I don’t think I talked about phases. I said certain people produced a lot of stuff and certain people consume a lot of stuff, and what I’ve realized since then, it’s not people, it’s phases.
That’s what you’re talking about now. What I find is, when I’m done with a hurdle, let’s say I sold a business, or I’m done growing it, or whatever, then I want to consume a bunch of stuff because I’m trying to figure out what to do next and taking a lot of information helps. But as soon as you focus on the goal, because you know exactly what your goals are this year, right? You’re growing Bluetick and you’re doing it this way.
You don’t need a bunch of information. You just need that point in time learning. I’m going to do Facebook ads next week so I got to learn that—Boom, do it, launch it. You don’t want just a bunch of inputs about things that are going to distract you in essence.
Mike: I find that the podcasts in general are distracting because they’re making me think about things that are not nearly as relevant to me as I need them to be. It’s better if I just take that time to think about the business itself and what I’m going to do next versus what other people are doing in their own businesses. As entertaining as it is, it doesn’t actually help me.
Rob: That’s right. Cool, man. We should probably wrap this.
Mike: All right. Well, take it easy. Talk to you next time.
Rob: Peace out.
In this episode of Startups For The Rest Of Us, Rob and Mike take some listener questions about hiring VA’s, struggling with engineering, and bootstrapping versus raising funding.
Items mentioned in this episode:
- Dear FCC
- Fearless Salary Negotiation
- Virtual Staff Finder
- Scaling SaaS
- Meet Edgar
Rob: In this episode of Startups For the Rest of Us, Mike and I discussed hiring VAs, struggling with engineering, bootstrapping versus raising funding, and more listener questions. This is Startups For the Rest of Us episode 340.
Welcome to Startups For the Rest of Us, the podcast that helps developers, designers, and entrepreneurs be awesome at building, launching, and growing software products, whether you’ve built your first product or you’re just thinking about it. I’m Rob.
Mike: And I’m Mike.
Rob: We’re here to share our experiences to help you avoid the same mistakes we’ve made. What’s the word this week, sir?
Mike: I have a website for you. It is called gofccyourself.com.
Rob: Really, I’m clicking on it right now. That sounds dubious. Is this safe for work, as they say?
Mike: It is safe for work. This is actually created by the Last Week Tonight show with John Oliver. The idea behind them putting together this website was that there’s some pending discussions inside the FCC about whether to deregulate certain parts of the internet specifically as it relates to internet service providers. It allows them to essentially self police themselves in a way that they decide whether or not what they’re doing is morally correct and net neutral, which is obviously not a good thing for net neutrality in general.
The FCC has made it very difficult to get to the page where you can actually leave comments in support or against this particular piece of decision making in the process. John Oliver and his team put together this website. It’s essentially just a redirect that takes you directly to the place where you can fill out the form and leave a comment.
If you’re interested in contributing your voice to that net neutrality legislation, then go over to gofccyourself.com. I’ve already done it. It does take a few minutes. I thought it would take two minutes so I’m hesitant to say that because it took me like 10 but I think that it’s well worth putting your voice into for them to hear it.
Rob: It looks like there’s another URL, dearfcc.org.
Mike: It’s the same type of thing except that, I believe, it sends a physical letter as opposed to just commenting directly on the FCC’s website.
Rob: Got it, very cool. Hey, we had a comment on last week’s episode. I thought it was a pretty thoughtful comment. I appreciate it. It was from a guy named [00:02:17]. He said, “Hey, first time commentary. Congrats Mike on reaching your MRR milestone. What makes it more impressive is you did it in spite of all the armchair criticism. All the more power to you.” I didn’t even read that part. That’s funny. He said, “I did want to say that hearing Rob talk about hiring an in house nanny and how everyone should get hired help was a little bit perhaps insensitive. Not sure if that’s right word but Mike’s response pretty much sums it up. Similar to a guy who could afford to fly first class and tells everyone they can’t imagine flying economy again and that everyone should fly first class.”
I appreciated his comment. A couple of things, first of all, I felt like the first class analogy was a little, maybe didn’t translate to what I was saying because flying first class is like 5 times, 10 times more than normal flights and the only value is comfort and perhaps snobbery whereas I was genuinely saying outsourcing stuff. It’s not about having a live in nanny. It’s about not mowing your lawn. That’s really what I was talking about.
I had switched topics by this point to if you’re a founder and you’re still mowing your lawn, and you’re pressed for time, and you don’t have time to spend with your kids or work in your company, and you’re still mowing your lawn, or shoveling you snow, or cleaning your own house, that’s not a money decision at that point if you’ve got any type of success.
I used to pay $55 every 2 or 3 weeks for a house cleaner. Most of us can swing that. None of this is stuff that I started doing after I sold my company. I started hiring small amounts of outsourcing over 10 years ago when I was literally making just a normal salary gig but I was trying to do stuff on the side. I wanted to clarify that and also say I apologize if I came off insensitive. Did you feel like I did?
Mike: I don’t think so. I actually thought it was kinda funny when you said I’m not advocating outsourcing your parenting of your kids and I was like, “Why not?” Isn’t that the point?
Rob: Mike’s like, “I am advocating outsourcing raising your kids.”
Mike: I was like, “When did we decide to go against that idea?”
Mike: I could definitely see what you decide could be misconstrued. I don’t think that that was your intent. As you said, the conversation had shifted from one topic to another in the middle of it.
Rob: Right. I don’t think everyone by any stretch should have some type of live in nanny. Sherry and I have been talking about that for five or six years. We haven’t been able to do it. We just didn’t have the house that it worked for back in Fresno. It really doesn’t have anything to do with suddenly having more money. I’m not advocating everyone should get a live in nanny. It’s game changing for us but that’s a personal choice.
The part that I am saying entrepreneurs and founders should do if you’re strapped for time, and all of us are, is that you should be outsourcing more of your day to day groundwork. That’s a decision you’re going to have to make early on. It’s like hiring a VA, I’m going to pound that drum forever, but if you’re still answering your own email support and you’re more than about 3 or 4 months into your product, you’re making a bad choice.
You can try to tell me it’s not a bad choice but I’m going to tell you over and over based on my experience and the experience of everyone who I’ve told this to, who haven’t hired someone says, “Oh my God, why didn’t I do this years ago,” that you should be doing it. It’s a different thing but hopefully that clears it up and is a little more helpful who think I’m some type of pretentious d-bag.
Rob: I’ve always tried to be on this side of that argument.
Mike: I do think that there are certain cases to be made where you don’t outsource that stuff. For example, like mowing the lawn. I find that sort of therapeutic because I listen to my headphones and podcast and stuff like that while I do it. That’s a regularly scheduled thing that comes up versus something like snowblowing the driveway and taking care of that where you’re much less in control of the weather and those things pop up and it needs to be taken care of. That is easier to make that decision on than something like mowing the lawn where it’s predictable, I’ll say.
Rob: Yeah. If you’re saying it’s relaxing for you, that actually is a good argument for it. I would say alright then, that’s not a bad choice. I actually cook quite a bit because cooking is not a chore to me. It’s actually something that I enjoy. I do outsource part of it. A lot of the prep, I use Hello Fresh or Blue Apron so I’m not going out shopping. It’s more expensive for sure but it saves me time.
Cooking itself, the act is similar to what you’re saying. I typically have a glass of wine and I have podcast playing and so it is actually relaxing. That’s a good point too to bring up. It’s only if this is something that’s detracting from your life.
Mike: I think that’s the point. If there are certain things that you can outsource because they are detracting from your life or they’re inconvenient, that was really I think the point that you were trying to make with the nanny. There are times where it’s inconvenient to drop what you’re doing to do something like picking up the kids at a specific time. You don’t have to be the one that does that. Again, that’s very different than being the person that are parenting your kids. Those are just two very, very different things. I think the distinction got muddled in a conversation, that’s all.
I just want to bring up a comment that we got. This one came from Josh Doody. Josh gave an attendee talk at MicroConf. One of the things that he talked about in his attendee talk was about SEO. This relates back to episode 338. He just said, “Hi, I just listened to episode 338. Summary of the Moz case study on ranking number one for competitive head terms. Really good stuff. I heard a couple of things that I’m going to try to keep improving the SEO on fearlesssalarynegotiation.com. I added the episode link in the case study that linked my MicroConf summary page. I think my talk in some of the links on that page could help people get started with SEO. My talk was a one on one level talk where I would say the Moz case study is 201 plus.”
He gives a website URL. It’s joshdoody.com/microconf. We’ll link that up in the show notes. Anyone who wants to go take a look at that, it’s a really good overview of what his talk was and it is some practical strategies if you’re not quite to the level of where that Moz episode that we did and all the different things that they did for SEO. If you’re not quite there yet, head over to this link. Again, it will be on the show notes. It gives a lot of the basic tactics and stuff that you can use to help your website rank in the search engines.
Last before we get started. I did not know this but apparently, for the past two or three years, there has been a Viking combat training facility here in my hometown.
Rob: Do they teach you to fight with the axes?
Mike: I think that they put stuff over the ends of them. I saw them training one day out in a parking lot. They have these giant bo staffs, they almost look like giant erasers or q tips or something like that. They are like padded on ends and they look like they’re ready to beat the snot out of each other in the parking lot.
Rob: That’s awesome. Your town is not that big so it’s kind of odd that you wouldn’t have known that.
Mike: I know. That was the part that struck me as odd. It’s literally called the Viking combat training center.
Rob: That’s fun. Last time we were in Italy, my son and I did gladiator training in Rome. It was like a one or two hour little adventure where we had foam swords and you wore the helmet. The stuff is bulky and heavy. It was super fun to learn kind of the different approaches to combat though.
Mike: What’s on the agenda for today?
Rob: Today, we are answering listener questions, trying to play catch up. I think we have one voice mail and a few written questions. Our first question is from Richard Gorbet. He says, “Hey Rob and Mike, love the podcast. Only one I have to auto download when a new one appears. A couple of years ago, there was a lot of chat about virtual assistants. Is it worth a new topic in one episode as I suspect the dynamics may have changed. I’m thinking from a help desk perspective but many, many uses for a VA. It’s come to my thoughts as my latest ideas about MVP in the next few weeks. Thanks.”
What do you think about this? I don’t know that it’s so much different than the previous thoughts we’ve had. Maybe the specifics of hiring have changed slightly but I think we talked about 15 ways to use a virtual assistant. I think all of that is still the same. That stuff hasn’t changed. What do you think?
Mike: I would agree. I think the specifics of how to go out and find somebody and vet somebody to do those things has definitely changed over the years but I don’t think that the types of stuff that you would have them do is going to change all that much. It’s probably going to be more of an evergreen topic to be honest. It’s just there’s always ways to save yourself time.
The one thing that I think that might change over time is that as the level of skills of people that are available at a certain hourly rate, that dynamic shifts over time. You might be able to find people who are more qualified to do things that are probably further along than what you would think that a typical VA would be capable of. Again, that’s going to be shifting the global economy in terms of who is available at what hourly rate and stuff like that. It’s not really a dramatic shift in what you would have them do. It’s just a matter of what people are skilled at, at a particular hourly rate.
Rob: I actually think the hiring process, at least the one I outlined most recently was through oDesk. That’s still where I would go today. I would use that or I would use Chris Ducker’s service, virtualstafffinder.com. It’s Virtual Staff Finder, that’s the URL. If I recall it was like $300 or $400 to pay them and they basically vet a bunch of candidates and then they give you the top three. They guarantee them, that if they don’t work out in the first whatever days, they’ll replace them and stuff.
If you have the funds, I would do that if you’re in a hurry. If you have less funds and more time, then the oDesk approach that we’ve outlined, I guess it’s Upwork now, the Upwork approach that we’ve outlined in the past is what I would go back to at this point. Thanks for the question.
Our next one is an anonymous question that he actually sent to me directly. He say, “Hi Rob, I’m in the process of creating a B2B SaaS app for universities but I’m struggling with the engineering of the application. What resources such as books, tutorials would you recommend for developing a SaaS app on the web? I’m a huge fan of the podcast and of your book. Thanks for all your help.” What do you think, Mike?
Mike: It’s funny, as I’ve been developing Bluetick, I‘ve come across various topics where this type of thing would be very highly relevant. I’ve looked around and depending on what you’re doing, it can be very difficult to find this type of stuff. It kind of actually spoke the idea of writing the technical side of developing a SaaS application, a book that basically covers that topic. The problem obviously, I just don’t have the time to do that kind of thing.
There’s also just a wide variety of topics that as a SaaS founder, you may run into them and you may not. It depends on the type of SaaS that you’re building and how data intensive it is, how much search you have to do, if you have to do data indexing. A lot of times, you can get away with just very basic stuff and then when it breaks, then you fix it.
I think it’s very easy to go down the path of trying to engineer something to work for the largest case that you could possibly envision your app doing and then get into it and realize that you’re not going to hit that for six months, or a year, or three years. You’ve over engineered the early stage stuff. There are certainly things in Bluetick where we’ve had to rewrite them two, three, there’s sections of the code where I’ve rewritten it four or five times just because the backend stuff has scaled to that point.
Had I sat down and just designed it on day one to try and reach that scale, it would have taken me so much longer to get something out there. I think you really have to just weigh what it is that you’re trying to accomplish and what those short term goals are which your primary ones should be get something working in front of people versus how do I make this thing survive in the long term.
Unfortunately, that’s something that’s sort of diametrically opposed to each other. You don’t want to have to rewrite code more than once or twice if you don’t have to but at the same time, in order to take those shortcuts, you almost need to build those sections of code as prototypes just to get to where you need to be and get that revenue in the door.
In terms of looking around and trying to find specific resources, I’ll be honest, I looked around and I could not find very many. There’s all the generic stuff on how do I build an application or how do I use this particular type of technology, and those are great and helpful but they don’t give you a much broader picture of how do I handle authentication or how do I handle permissions inside of a system.
There are different areas you can go into like claim space authorization and all these different things. At the end of the day, you got to pick what is right for your application and what is going to get you as far along as possible with the least amount of effort.
Rob: The hard part of this is if you get into like how should I do authentication, it’s going to depend from language to language. You should use the built in .NET stuff for .NET but in Rails, you should use the built in Rails stuff. You almost have to go one level higher and talk about concept.
I agree with you. I don’t know of a single good book or tutorial course about really the high level engineering side that’s not language specific. I went to Google and typed in how to build a SaaS application. There’s actually some decent stuff. There’s a good conversation on Quora. There’s a good article on Glenn Stovall’s blog. He’s a MicroConf attendee. He talks about all the technology he would use and it’s like 19 apps in a row. He made the list. Thanks Glenn. I haven’t even noticed that. That’s kind of funny.
That’s where I would start. Again, I don’t know of any tomes, any books, any dead tree of things that are out there. It’s much more going to be about blogs, article here and there. I do know that there are people out there like Derrick, my co founder, has a blog called Scaling SaaS. It’s at scalingsaas.com. He talks about challenges that he’s run into and how he’s fixed them but it’s not a step by step tutorial or a really deep dive into engineering a SaaS app. Perhaps, there is a gap in the market here that someone would be interested in filling.
Or if you have heard of some good resources for stuff like this, feel free to write in questions at Startups for the Rest of Us and we’ll be happy to mention them in a future episode.
Laura: Hi, this is Laura Roeder from Meet Edgar. Hey guys. I was wondering about Rob’s perspective on bootstrapping versus fundraising now that you are operating inside of Leadpages, a funded company. I’m a bootstrapper, I know you guys have been big proponents of bootstrapping over the years. What have you learned being inside of Leadpages about bootstrapped versus funded companies and has it changed your point of view at all about what you might like to do in the future? Thanks.
Rob: This is a really interesting question. The hard part is think about how I run a bootstrap company versus maybe how you run one versus Reuben Gomes versus Josh Pigford. I don’t know if you can say there’s one way to run a bootstrap company and so I can only compare the way I run them with the way that the Leadpages team runs them.
If you think about a funded company in Minneapolis run by Clay Collins and his two co founders, started as a distributed company and then raised funding and grew to 170, 180 employees at this point, it’s probably a different trajectory. They’ve always been profitable. Different trajectory than a funded company in the bay area that maybe B2C, has never been profitable and is hiring a boiler room of bros to make the phone calls.
There are a lot of different ways and thoughts around raising funding and different ways to run a company. I guess I want to couch that in advance by saying it’s only one person’s experience. It’s with basically two companies, comparing them to one another.
The base thing I’ve learned moving to a funded company is that it’s so freeing and amazing to not have to worry about resources, to not have to be concerned with adding a $200 a month server or upgrading the database over to a $2,000 a month box. You know it’s going to fix your problems but you just don’t know if you have the money to do it.
That is gone. I’m not saying money is infinite but compared to the bucket we were in a year ago, before the acquisition, money is essentially as close to that as you can get. Anytime we bring up a problem and we’ll say, “Here’s how to fix it but it’s going to cost this.” The cost is actually the afterthought in the conversation. That’s very freeing and it allows us to operate quickly. We can hire. We can pay market rates. It’s like having the resources, it’s crazy.
Especially because we’re not doing the crazy I’m going to raise $20 million and do the B2C shuffle where we just hire way out ahead of sanity. You hire 20 people before you hit product market fit. We’re not doing that. We’re literally hiring to scale. This is the perfect time at which I would have raised funding if we were going to. It’s a point at which you have product market fit, you’re growing quickly and you’re just pouring money into either scale the marketing or scale the engineering. That’s been cool.
The other thing I’ve learned is that specialization is amazing. The fact that they don’t have people who do support and customer success and marketing, we used to have a Drip when there were five of us. There was one person doing support. To be honest, there’s like eight people doing support for Drip. Marketing is divided into like some people just write blog posts. That’s all they do all day. And then there’s this person and all they do is all the social paid acquisition. There’s this other person and all they do is the search paid acquisition because they have the staff to do that.
Specialization is extremely powerful because you can get so good at stuff. This is when we see these case studies like we talked about last week. It was two weeks ago, about the SEO stuff, the reason those people are so good at that and can write that incredible case study is because that’s all they did. That’s all they did for 90 days straight, was work on that one problem and you can accomplish a lot doing that.
I think another difference and I don’t think it’s not a fun diverse thing but like Drip was an engineering driven culture because I’m an engineer and so is Derrick. Leadpages and marketing is different culture so it’s a different way to look at it, a different way to run a company but that’s not because they’re funded. It’s because they’ve always been that way. Clay, Tracy, and Simon bootstrapped Leadpages to, I don’t even remember what the number was, but it was several million dollars in annual revenue. They kind of are a bootstrapped company that then raised funding.
I think those are some cursory thoughts. I could probably do about a 20 minute rant, not even a rant, just a conversation of me talking about the differences but I think those are probably the most pronounced.
Mike: I think the only thing I’d add to that is that there’s this I’ll say sort of a pervading fallacy that when you start talking to not self proclaimed experts but the people who are leading the masses when it comes to startups, you look at them and your immediate thought is, “Oh, they know what they’re talking about and that’s the way to build a business.”
The reality is that that is true to an extent, however, there are lots of ways to be successful and there’s more than one path to do it. There’s no one true path. There’s no one silver bullet. There’s no one way to do things. There’s lots of ways to do it and be successful. Just because it worked for somebody else, it doesn’t mean it’s always going to work for you and that when you’re looking at those types of examples, that’s one path. There are lots of others that may or may not work for you. It’s about finding what will work for you.
Rob: It’s interesting. There’s always these big things about don’t raise funding because you’ll lose control, or you’re going to make bad decisions because you have too much money, or you’ll feel all this pressure from investors. I’m not the founder or the CEO of Leadpages but I don’t feel like I’ve lost control like we’re being pushed to make bad decisions because we have “too much money,” or that there’s all this pressure from investors. Perhaps the board or the CEO, Clay feels different than that.
It’s not this black and white dichotomy that so many people make it out to be. You and I have never done that. We’ve never been anti funding. We’ve always been anti the dumb B2C startups that have no product trying to raise all this money and go viral. It’s the stupid Silicon Valley stuff.
For 10 years, I’ve been saying there’s a right time and a right place to raise funding. I think it’s post product market fit. You bootstrap to that and then you add the fire to grow the company. Typically, it’s going to be more B2B although if you had a B2C that had hit, I think there’s a good time to raise it as well.
It’s really interesting. There’s a lot more to talk about. Maybe we’ll record an episode in the future and revisit that whole topic.
Mike: Yeah. I think you and I are more anti pipe dream where you have something that you’re putting out there but you’re not charging for it and you don’t have any way of making money. The reason you need funding is in order to increase your reach and get it in front of more people. And then, at some point down the road, you’ll figure out how to make money from it. If you can’t do that very early, then it makes it difficult to build a business out of it.
Rob: Right. We’re anti billing slide decks and asking for permission instead of actually building a company. You should be able to build your company to the point where people want to invest without any funding. It’s very, very rare exceptions. Maybe hardware, although even these days I would say do a kickstarter. Maybe there’s something with incredible computing power, something that you can’t have access to and I would say build something simpler first.
For the most part, most of what we all do, you can bootstrap that to the point where it becomes very interesting to investors.
Mike: I think that about wraps us up for today. If you have a question for us, you can call it into our voicemail number 1-888-801-9690 or you can email it to us at email@example.com.
Our theme music is an excerpt from We’re Outta Control by MoOt used under Creative Commons. Subscribe to us in iTunes by searching for “startups” and visit startupsfortherestofus.com for a full transcript of each episode. Thanks for listening and we’ll see you next time.
In this episode of Startups For The Rest Of Us, Rob and Mike make their predictions for 2016, forecasting bootstrapping related topics as well as the greater technology space.
Items mentioned in this episode:
Mike [00:00]: In this episode of Startups For the Rest of Us, Rob and I talk about our predictions for 2016. This is Startups For the Rest of Us, Episode 270. Welcome to Startups For the Rest of Us, the podcast that helps developers, designers, and entrepreneurs be awesome at launching software products, whether you’ve built your first product or you’re just thinking about it. I’m Mike.
Rob [00:23]: And I’m Rob.
Mike [00:24]: And we’re here to share our experiences to help you avoid the same mistakes we have made. What you doing this week, Rob?
Rob [00:28]: Things are pretty good. It’s the last week of the year and we have a new Drip HQ. We moved offices just a few blocks to a nicer building. We’re up on the second floor now, with a nice view of a busy street, and it feels cool to be downtown and just have a lot of people around. It’s like a 50,000-square foot building here in downtown Fresno, and it’s good to be around even more tech companies. We were around maybe 27-ish small software companies over at the other building, but it was only about 10,000 square feet, and this one just has a larger feel. And it’s new construction retrofitting a 100-year-old building. It’s got a unique vibe to it.
Mike [01:03]: Cool. Did everybody move from the other building over to this one? Or how does that work?
Rob [01:07]: A lot of us did, yeah. It was up to you if you wanted to move. The rent’s a little higher here. And it’s in a different location, so some folks opted to stay at the other one and then were backfilling with other companies. There’s been a nice tech scene that’s formed here over the past few years. And so what’s nice is there’s a waiting list at both buildings, from what I understand, and so we’re able to keep them occupied and keep the energy level. It’s something that I think’s going to be taken up. We’re one of the first companies, but I think there’s maybe a half dozen, that are moved in here, and there’s going to be 40 eventually. So it’s still pretty sparse, but just seeing people on the hallway and being able to look out over a cool downtown street is fun. It’s a different vibe than I’m used to, but it’s neat.
Mike [01:44]: That’s cool.
Rob [01:44]: How about you? What’s going on?
Mike [01:45]: Well, I’ve realized that one of the things that I talked about last week on our yearly goals episode was I was going to try and be writing more. And I realized that I should probably have classified that as more of a success than I think I initially did because I realized that one of the things that I’ve been doing is keeping a journal and writing in it three times a day. And I don’t know why I completely spaced out on that, but I did. So I would probably say that that was much more of a success than I initially had indicated on the podcast even though I write it for myself. But I write in it, like I said, three times a day: once first thing in the morning, and then once in the late afternoon, and then once just before I go to bed.
Rob [02:21]: Yeah, it’s interesting because your goal was actually “Keep up my writing habit.” And that doesn’t necessarily mean publishing, although that’s what I had read it as. I’d assumed that you meant to actually blog and push stuff live. Was that your intent when you said, “Keep up the writing habit,” was just to write and not necessarily to publish?
Mike [02:38]: It was a little of both. I think I had initially intended to publish more, but at the same time, there’s a certain amount of content that you create that you don’t ever necessarily publish either. And what I wanted to do was to make it more of a habit than anything else, so just getting into the habit of writing on a very regular basis as opposed to writing a couple of blog posts or writing a couple of articles or something like that and then not coming back to it for two of three months and just doing zero work on it in any way, shape, or form of writing.
Rob [03:06]: I see some value in writing and not publishing, but I think there’s so much more value in getting it live. And so I would give you a half pass on this.
Mike [03:14]: Sure.
Rob [03:14]: Just on my personal, metric system, my arbitrary, personal metrics.
Mike [03:18]: Yeah, but I think that when I’d looked at that on last week’s episode, I’d looked at it from the perspective of, “Oh, I haven’t really written anything at all.” And that wasn’t necessarily true. I agree with you I’d probably get half credit on that, definitely not full credit of course because I don’t think it got published. There’s a huge amount of work in there that just never got published. But the idea I had in mind was like, “Oh, I was actually writing quite a bit here.” I do think I need to do a better job of publishing more, so that will make its way to the forefront, I think, this year.
Rob [03:45]: Indeed. Other news, wrapping up the year, was able to finally make a solid hire to help with growth. He started last week. So pretty excited about that, able to pull some stuff away from myself and Anna, marketing tasks that we’ve been handling. And he is going to be able to focus on this stuff. And so one example is I was messing around with retargeting and trying to optimize it and get it to the place where it needed to be. And then eventually we stopped it at a certain point, and he is able to spend 30 hours a week basically focusing on this kind of stuff. And so already he came in with a much more advanced- and it’s a time-consuming approach but it’s definitely one that I think has legs. So I’m really looking forward to getting going in January with our ramping back up marketing. Because as of essentially next week, when this episode comes out, that’s when things start to come back alive and all the dips and trials and the dips and growth and all that stuff I think starts to turn around for all of us. And so yeah, I’m always excited to hit the ground running as we enter early in mid-January.
Mike [04:39]: It seems odd to be hiring right at the very end of December.
Rob [04:43]: Yeah, it was a little bit of a coincidence. I think I posted it in November and then really wanted to find the right candidate. Because what’s interesting is there are a lot of developers, as an example, and designers. And they’re not necessarily easy to find really good ones, but they’re out there, and you know how to test for that. But finding someone who has the right mentality, or the right experience, and the right hunger to actually do pretty intense marketing and really go after the growth opportunities, it’s still such a nascent, unique skill set, right? It’s not something I think that’s easy to test for. And so that’s what I did, was went around and around with a bunch of people. And when he finally came on, I realized that it’s actually a pretty good time for him to come on because it’s so quiet.
And so we haven’t launched anything yet, but it’s been all prep work. I got him onboarded, got him in the system in terms of payroll and all that HR stuff, and then got him into our processes. He’s now the blog editor in essence. And he really hasn’t started doing any outreach or doing any of the stuff yet, but he’s all set up to hit it hard next week when everything actually ramps up. So it turned out to be decent timing even though it didn’t first appear it would be.
Mike [05:49]: Very cool. To circle back on one of the things that we talked about last week, was some of the different monthly experiments and things that I wanted to do this year, and you had ask me to come back with a list of these 12 different things. And so what I did was I sat down and I started looking at those, and what I realized was it wasn’t necessarily a series of month-long experiments so much as it was an extension of what I read in a book called Habit Stacking. You can find it on Amazon. We’ll link it up in the show notes. It’s called Habit Stacking: 97 Small Life Changes That Take Five Minutes or Less. And what I want to do is essentially stack a bunch of these things together. And a lot of them are just little things. They’re not necessarily major life alterations or anything like that.
So one of them, for example, is drinking at least eight glasses of water a day, which I did it for a little while, but I didn’t keep up with that habit. So what I want to do is I want to go back to some of these and revisit them and start working on those and try and stack them up over time. And I’ve stumbled across a website called healthmonth.com, which allows you to put forth goals that are essentially measurable, and you can put things like that in there. So whether it’s getting up early, or exercising, or setting aside time to do X, Y or Z, you can track those things in there. And it will go on a month-by-month basis, and you get to essentially measure your progress against that of other people who have set a similar number of goals for the month.
Rob [07:06]: So are you going to report on that weekly, bi-weekly here on the podcast?
Mike [07:10]: Probably not. Because, like I said, there’s a bunch of them in there. But you had asked me to put together what that list was, so I’ll quickly run through them. We’re not going to spend very much on it, I don’t think. But they included things like exercising at least 30 minutes a day for 6 times a week, drinking 8 glasses of water a day, going to bed and waking up early at certain times, no junk foods or snacks after 7.00 PM, setting aside an hour to write for my blog, working at a co-working facility 3 times a week, which is something I’ve tried in the past but it’s never really stuck or worked out for me. So I think I’m ready to go back and try and revisit that and try it for a month or two.
Another one was to track all my food intake every day, meeting 10 new people in a given month. I’m going to specifically target a non-MicroConf month for that. I’m not going to cheat on that one. And then spending 15 minutes a day doing, I think I’d talked about this before, it’s a mental game called SuperNBack which allows you to train your brain to remember things a little bit better. So I’ve got a game called Reactor on the iPad that is really good for that, and then scheduling my work day in advance, and checking e-mail only twice a day, which I do that on occasion, but I’m not real good at limiting myself and checking e-mail twice a day so –
Rob [08:19]: Is each of those a one-month thing then?
Mike [08:21]: Yes, they are. My goal is to say, “Okay, let me take one or two of these and just do that for at least a month and see if I can maintain that habit over the course of the month.” And the goal, of course, is to, by the end of the month, turn it into a habit as opposed to something that I’ve just tried out. And if I need to extend it as something that I’m going to track, I will. But the idea is to be able to take those things and engrain them into my daily routine so that I don’t necessarily have to think about it or track it anymore, I will just do it. And that way, I can drop off my list of things that I want to stick with. And if it turns out that there’s something that I really just don’t enjoy or don’t want to continue with, then I’ll just drop it off. And then the next month I won’t continue tracking that or doing it.
Rob [09:07]: I think if there’s one adjustment I would make, as you said, you want to look at one or two of these things in a given month, and I would definitely not start with that. If you’re going to go January 1, pick one and focus on it. If you try to do too many things, it overwhelms you and it’s hard to change behavior. So at least for the first five or six months, until you get the hang of this, I would probably try to attack one thing at a time, unless you really feel like you can do multiple things.
Mike [09:31]: Yeah, some of them are easy enough. For example, drinking more water per day, that’s not terribly difficult. Really what it boils down to is just remembering to do it. So you can do that with timers. I found that there is a prescription reminder application from I think it’s Walgreens or something along those lines that you can throw something in there and it just reminds you every couple of hours to do something, and I’ve used that in the past.
Rob [09:54]: So you mentioned drinking eight glasses of water per day, but you missed the one of drinking eight glasses of beer a day.
Mike [10:00]: Well, that is in the water. You can call it beer if you want to, but –
Rob [10:04]: Right. Beer, water with hops.
Mike [10:06]: Yes.
Rob [10:06]: All right. Well, let’s dig in today. We’re doing our predictions episode, which is an episode that we like to have fun with, right? We made some predictions about a year ago, and some of them have nothing to do with entrepreneurship. We had predicts about Google Glass, net neutrality. And so we revisit those and we figure out if we had success or totally whiffed on those. And then we look at some predictions moving forward and what we think is going to happen in 2016. I think we each have one or two that might relate to bootstrapping, and then others that we just see in the greater tech space. So why don’t you kick us off with maybe looking back at some of your predictions from 2015?
Mike [10:37]: So the first one I had was that net neutrality is going to take a bigger stage. And the thinking I had behind that was that Netflix had started paying service providers for higher bandwidth to serve up a lot of their content. And internet speeds, in general, have increased by 50% since the beginning of last year. So what I was thinking was that this was going to be essentially a problem for many businesses where they were going to feel that they needed to pay for their content to be served up. And I don’t think that this has really come true. I haven’t seen a lot of battles or a lot of public discussion about people having to pay extra for their content to be served up. And it could just be that Netflix is so large and serves up so much bandwidth worth of content every single night that they’re more of an outlier than anything else.
What I have seen though is an interesting shift in how a lot of the content providers have started to go direct to people. So I think it’s interesting that companies like HBO and Starz and Showtime have started coming out with their own subscription services that essentially bypass the cable networks. So I don’t think that those directly affects net neutrality. I would probably call this one a miss more than anything else, but it’s interesting to see the shift for the content providers to go direct to the consumers rather than directly through cable providers.
Rob [11:55]: Yeah, I’d agree with you on this one. I don’t think you hit the nail on the head, but there’s definitely something cooking there where we’re going to continue to see shifts and conflicts in this space. My first prediction for 2015 was that Twitter would become profitable and it would piss off its users in the process, but it would be a solid opportunity for paid placement or promotion for bootstrappers and startups. And I think that I was wrong on the first two aspects because as far as I know, Twitter was not profitable during any quarter in the previous year. They obviously haven’t recorded Q4 earnings, but in Q3, they were still losing money. I don’t feel like they pissed off their users in the process of not becoming profitable. What I was trying to imply there was that they would become profitable but they would have to just stuff so many ads down our throats that there’d be a backlash. That didn’t happen. Solid opportunity for paid placement and promotion, I do think that one is correct and that Twitter cards and other Twitter paid placement is still a viable alternative, even heading into 2016, to get some cheap clicks.
Mike [12:53]: My second prediction was that the number of startups in the wearables category is going to skyrocket, both in terms of the hardware and software. And I hesitate to say that this was a complete failure or a complete success in either way. It just doesn’t seem to me like there’s been a huge number of startups in this area. Obviously Apple came into this space with the Apple Watch, and Fitbit and a couple of other companies have started pushing their wearables, but it doesn’t seem like the number has skyrocketed. I was thinking it would have much more of an impact than it probably has.
Rob [13:26]: Yeah. I think there hasn’t been enough of a ecosystem around it since the Apple Watch. It didn’t “take off.” I know a lot of people bought it, but it really has not become a day-to-day use thing. I don’t think I’ve seen anybody in a while wearing an Apple Watch, maybe one or two people at a tech conference or something. But it hasn’t become a day-to-day thing like an iPod or an iPhone did that I think the wearables category is either still getting going or it’s dying at this point, and I’m not sure which. I think eventually wearables will find out which form factors work for us, but 2015 was not the year of that, for sure.
Mike [13:59]: Yeah, I have seen a couple of people use them, but I think it’s going to be probably several years before companies really figure out what people even really want from a wearable device.
Rob [14:08]: Yeah, and that’s what we were saying back in 2013. So my second prediction was that video ads, namely YouTube ads, would be a big opportunity for cheap clicks in 2015. And I think this one was a success. I don’t know how bold of a prediction it actually was. I guess the way they could have not been an opportunity for cheap clicks is if a lot of advertisers had jumped in on it and, to be honest, that’s what’s happened with Facebook ads now, right? Facebook is a lot more competitive. They’ve nailed mobile and they’re making buckets of money off of their ad platform. And typically when the provider’s making buckets of money, like a Facebook or a Google, that means it’s not a good opportunity for cheap clicks anymore.
And so that could have feasibly happened with YouTube in 2015. It did not. It is still a big opportunity for both retargeting and just cheap ad clicks in general, if you can figure it out how to make it work and reach your audience. If you haven’t looked into it and you are looking for another paid marketing avenue, YouTube ads continue to be there.
Mike [15:02]: My third prediction was that Google is going to screw all the bootstrap startups and there’s very little we can do about it. And I don’t think that there was any large event that comes to mind in terms of Google making our lives difficult. Obviously they make changes to the UI in some of their different applications and stuff like that, and the cost of doing paid advertising through Google AdWords is really high. But it doesn’t seem to me like there was any one major event that you could point to and say, “Hey, these guys have really screwed over a bunch of people.” I would chalk this up to an inaccurate prediction.
Rob [15:33]: My third prediction was that VR, Virtual Reality, would actually be a hit with the early adopters set in 2015, and that did not come true. I know that a couple of headsets came out. It does not seem, even with the early adopters, to have taken off in any way, shape, or form.
Mike [15:49]: My next prediction was that Google Glass isn’t going to go anywhere fast. And I would say that this one, it’s hard for me to judge on whether or not this prediction is successful because I have not seen very much uptake and people using Google Glass. But just a couple of days ago, Google came out and said, “Hey, we’ve got another version of Google Glass coming out.” I really thought that they were probably going to be shutting it down. But I just don’t see any demand for it. I don’t think that people are going to use it in a widespread fashion. I can definitely see places where people would use it in very specific scenarios, but I just don’t see it becoming widely adopted.
Rob [16:23]: Yeah, it was an experimental form factor and they were pushing the envelope. It didn’t take off. They obviously sold their early $1500 versions. They’ve redoubled, and they’re iterating on a hardware schedule, right? You can’t iterate as fast with hardware as you can with software. I think it will find some niches and it will be really worthwhile for whatever, airplane mechanics or surgeons or something. But I don’t see that this will have mass market adoption. I would agree that if you look back a year ago, we didn’t know if Google Glass was going to take off or if they were going to do an actual consumer version. So I think your prediction came true. The fact that nothing really happened with it is what happened in 2015.
My next prediction is that we would see our first sub-$100-a-year, consumer-level, five-terabyte cloud storage service. And I think the week after I said this, someone said that Microsoft was already offering unlimited cloud storage. And then within the past month, they actually revoked that. I don’t know if you heard about that, but they basically said, “We’re not going to do unlimited anymore.” And they backed it way off to a couple of terabytes, I guess. So I’m not sure if this has happened. I was trying to Google around a little bit before this episode and I didn’t particularly come across a mass-market, five-terabyte, sub-$100-a-year service. Certainly, if it didn’t happen this year, I think it’s going to happen in 2016. But maybe if someone out there knows of a reputable service that’s not some fly-by-night thing in someone’s garage that is actually offering this level of storage for that price, you could hit us up in the comments or via e-mail at firstname.lastname@example.org.
Mike [17:49]: Yeah, it’s interesting because I’ve looked around at that a little bit as well, and you see places where they’re doing unlimited backups for $5 a month for Backblaze and a couple of other service, but that is more of an archiving service. It’s not necessarily real-time like Dropbox, where even Dropbox is what, $15 a month or something like that. You can get a terabyte, but you can’t get five yet. But I think you’re right though. I think that it’s coming.
My last prediction was that cloud platforms and services are going to be viewed as a commodity by the end of the year, with not much differentiation between them other than their brand identity. And I have gone through and poked around the differences between Amazon, like the AWS services, Azure, and Rackspace. And quite frankly, there is very little to differentiate them from one another. They’re all trying to point to Gartner or third-party companies that are doing experiments and research on the platforms to try and find out which one is the fastest and which one is the best. And of course they’re paying these companies to do that research. So it does make it a little bit suspect when they come back and say, “Oh, sure. Microsoft paid us, but we did find that they were faster.” But I don’t see very much difference between any of these different platforms. I just don’t see it. So I would say that this one’s a win.
Rob [18:59]: My last prediction for last year was that we would start seeing 3-D printers in the houses of our early adopter friends and I would call this a miss. I know very few people who have 3-D printers in their homes. I’ve seen them start to get into schools. Several of the schools in our area have them, seeing them more and more in local labs and makerspaces, also saw them for sale at Barnes and Noble the other day. There was a 3-D printer there, which was surprising. But being in the home thing, it just doesn’t seem to be there, and I’m wondering if it’s ever going to have that moment that computers had where suddenly we all owned one, or if 3-D printers are going to continue to be this external service that we see at schools and maybe in offices and facilities that need to print and we’re all just going to do it on-demand instead of owning and maintaining our own 3-D printers.
Are you ready to dive into our predictions for 2016?
Mike [19:46]: Yeah, absolutely. Let’s go.
Rob [19:47]: Why don’t you kick us off?
Mike [19:48]: Well, the first one is an add-on to last year and it’s about the wearables category. And I don’t see this going too far. I think that there’s still going to be a lot of churning in the wearables category and it’s going to be several years before any of these devices become really big. I think that the Apple Watch is not going to be nearly as big as the iPhone or the iPod ever turned out to be. So I think that Apple is, in the coming years, going to be looking to see what other products they can develop. And maybe they’ll launch a new product by the end of the year. I don’t necessarily think that’s the case, but at the same time, the general prediction here is that over the course of the coming year, we’re probably not going to see a lot out of this category. There’s going to be some new announcements here and there, but there’s not going to be anything major that comes out of it.
Rob [20:30]: Ooh, I like this prediction because it feels pretty bold. Because I think we’re ripe for someone to come in and really nail this. And it is most likely going to be Apple with like a V2 of the watch, because that’s when they start getting traction with stuff, but I think somebody’s out there really doing some good work, and there’s a decent chance that we could see someone disrupt this category this year.
Mike [20:48]: Got you. Well, I’ll take the opposed view on that and say, “Not this year.”
Rob [20:51]: Yeah, totally. Well, that’s why I like the prediction, right? That it’s actually bold, and maybe a little bit counter to what I think some other folks might think. My first prediction is that single-round bootstrapping, also known as fundstrapping, will become a common, viable option, both in our circles and elsewhere. I’m just hearing more and more about bootstrappers who are getting to a little bit of traction, let’s say between 5 and 20K MRR, and then raising around to just up the game to grow pretty quick, and then to get to profitability and essentially issue dividends to the investors and then spit off cash, instead of doing these multiple rounds of financing where you’re just trying to get bigger and bigger and bigger, and eventually most of them implode.
And so whether you call it fundstrapping or single-round bootstrapping, this is a term I’m tossing around right now, I am seeing more of it, and my hope is that it does continue to become a pretty viable option in 2016. The reason I like this model is because it counteracts all of the negatives of raising traditional VC funding, right? The thing of someone taking over your board and taking control is gone because there’s no board seats. The idea that you’re pushed to get just get bigger and bigger and bigger and basically destroy a company that could be viable as a million-dollar or five-million-dollar company is gone because that’s not what you’re doing. It also gets around the idea of “I’m going to build slide decks instead of build businesses, and I’m going to spend six months pitching and trying to raise this $2 million thing. And that’s the big victory lap is when I raise the funding.” That goes away because let’s say you’ve already built the business up to a 5 to 20K MRR business, which means you’ve actually done something interesting and you’ve had the rubber meet the road, and then you’re purely raising the fundraising as a growth mechanism, which is always the point where I have thought that funding is a good idea. It’s when you have some traction and you just need to add $1 in order to pull $5 out the other side.
So all that to say I still think bootstrapping is very, very much alive and it’s going to be far more common. But this idea of a [?] raising a single round, single-round bootstrapping as I’m looking at it now I think is something that I’d like to see more of in 2016.
Mike [22:51]: Are there any other specific metrics you’re pointing at for here or you’re looking at for specific websites where there are terms sheets for this type of thing commonly available?
Rob [23:00]: Yeah, I see your point. It’s like, “How do you measure this?” right? Because I basically said it will be a common/viable option. What we’ve already seen in 2015 is Indie.vc has basically an outstanding offer on their website to do this. I have heard David Hauser was on Rocketrip podcast a few weeks ago talking about this kind of stuff, although he’s investing at a higher MRR. I’m doing it. I’ve talked to a couple of other successful folks, who, if I’d mention their name, you would know who they are, and they’re looking to invest in startups like this. Because the interesting thing is these kinds of startups have a huge chance of success, but it’s more of a modest chance of success. So it’s a lower risk than investing in the next Twitter or Facebook, and there’s a lower rate of return as well, right? You’re not going to 10X your money with this. You’re not going to 100X your investment. But you stand a much, much better chance of hey, maybe you earn 10%, 20%, 30% on your money every year as this thing spits off dividends. And so I do see people moving into it. I don’t know that I have an absolute metric of what I think we could measure this by, but it’s just something that I think’s going to become more prominent in 2016.
Mike [24:04]: Yeah, that leads into my next prediction, which is I think that we’re going to see a lot more bootstrappers in our circles concentrating less on making money for the sake of making money and focusing more on doing what they enjoy doing and living their lives on their own terms. And essentially what that amounts to is a less of an emphasis on consumerism and accumulating stuff. Because I think you get to a certain point in your life or your career, and you look at it and you say, “Having the big house or the big mansion on the hill doesn’t really matter so much as the things that you’re doing and the things that you find enjoyable on a regular basis.” And this is another one of those things where I think it’s difficult to measure, but I feel like we’re going to hear a lot more stories about this kind of thing.
Rob [24:43]: My second prediction is that Twitter will become less relevant than it is today. It will return more back to its roots where a lot of journalists are using it, news continues to spread on Twitter and the technorati will use it. But the adoption curve for Twitter I actually think is going to be on the decline. I think it’s going to be ripe for an acquisition. It’s still has been unable to turn a profit. It’s been unable to monetize it’s user base, and it just can’t do that forever. And I think 2016 will spell some changes for it. I still think Twitter is a reasonable communication tool, but it’s definitely a lot different than it was a year or two ago. And unless Jack is able to get in and really turn things around, I think they’re looking to be on the decline in 2016.
Mike [25:25]: My next prediction is that we’re going to see fewer IPOs and more acquisitions in the tech space, especially at the higher end. And the reason I think that is because from the so-called unicorn companies, there’s a lot more of them now than there used to be, the ones that that are valued at a billion dollars or more. And I don’t see a lot of these companies doing anything dramatic or really innovating in their spaces. I think that they’re going to hunker down. And they may run some experiments here and there, but it also feels to me like their main growth strategy is going to be through acquisitions and acqui-hires rather than building their own stuff and extending their reach. And as a result, I think that we’re going to see fewer of these companies actually go through an IPO, and we’re going to see more of them eating each other alive.
Rob [26:09]: That’s interesting. That ties into my third prediction, which is that the public markets will continue to value companies lower than the private markets. This has already started in 2015 where companies being privately held as they raise rounds of funding, they’ll be valued at a certain level, and then they go public and their stock actually drops when they go public. And this was the exact opposite 15 years ago, right? That was the liquidity event and the big payday when everyone doubled their money from the most recent private round. And it’s been the opposite a number of times in 2015. And this ties in with what you’re saying, that unicorns are starting to stagnate.
A lot of them don’t have unit economics that actually make sense. They have literally been paying a dollar to make 50 cents. And they keep saying, “We’re going to make it up in volume.” And certain business models, like in Amazon, you can do that with, but several of these unicorns have forsaken any type of not even just profit, but any type of unit economics that make sense. And so I think we’re going to see some fallout from that, as you predicted, and I think that’s going to continue to result in these public market valuations being lower than private markets, which is going to keep a lot of people private longer, resulting in fewer IPOs.
Mike [27:13]: Yeah, it almost seems to me like the fact that they’re paying more to acquire a customer than they’re making from the customer, it’s not even just that they’re doing that. It’s just that they’re also not maintaining those people as customers moving forward. So you had said that oh well, companies like Amazon can do that and make it up on volume. And I think what you really mean is that because somebody uses Amazon, they’re so happy with it, they will continue to be a long-term customer for it. So depending on how you’re going to measure the cost of acquisition for that customer, maybe it is a dollar and you only make 50 cents from the customer, but over the course of the long term, you’re going to be a Amazon customer for a long time. I looked on my account, and I think I have been an Amazon customer for almost 15 years now. I’ve spent easily tens of thousands of dollars with them. And they’re able to do that. But I think a lot of these companies are just not getting people to come back because it’s interesting for people to check them out. But after that, they have no real reason to come back and buy a lot of other stuff from them.
My last prediction is that drone technology’s going to take some serious step forward. And I base this on the idea that new FAA Regulations that have come out that essentially force people to register any drones that are over eight ounces, and I think it’s about 250 grams or so. And there are a lot of drones that fall into that particular category, but because of that lower weight limit that says, “Hey, anything underneath this limit, you don’t need to register,” I think that there’s going to be a lot of technology advances in the space that make it feasible to have drones that are very small, or I’ll say featherweight or ultra-light or whatever the term is, that they’re going to be using for that these days. But I think that you’re going to see a lot of advancements in the size of the components and the weight reduction and things like that to essentially circumvent the FAA Regulations for registration.
Rob [28:58]: And my fourth and final prediction for 2016 is that virtual reality will actually be a hit this year with the early adopter sets. So this is just carrying last year’s forward. I think this thing’s going to catch. I think VR and AR really have a future. And I hope it doesn’t turn into an AI thing where 10 years down the line, I’m still making the same prediction. But I feel like with the release of the Oculus, which is supposed to happen, what, here in Q1 of 2016, that we’re going to start seeing something catch on because [?], the Internet of Things, wearables, and VR, right? These are the next big things. One of these has to catch.
Mike [29:30]: I think I heard a podcast episode from, was it the Daily Tech News Show, where they talk a little bit about some of these different things. And especially with the VR headsets and things like that, there are certain things that almost need to be in place in order for it to catch on. Like the early days of the internet, you need to be able to buy stuff and you need to be able to not take the headset off in order to interact with the world around you. And if there’s any sort of pay walls inside of a virtual reality system that you have to leave that frame of reference, it’s going to make it difficult for it to catch on.
Rob [030:02]: So those are our predictions for 2016. It’s our last episode of the year, and we will see you in early January. If you have a question for us, call our voicemail at 888-801-9690, or e-mail us at email@example.com. Our theme music is an excerpt from We’re Outta Control by MoOt. It’s used under Creative Commons. Subscribe to us on iTunes by searching for “startups,” and visit startupsfortherestofus.com for a full transcript of each episode. Thanks for listening and we’ll see you next time.