Episode 360 | The One Where Rob Takes Over the Show

Show Notes

In this episode of Startups For The Rest Of Us, Rob takes over the show and answers a number of listener questions. Topics include launching a book and dealing with two sided market places.

Items mentioned in this episode:


Rob: In this episode of Startups For The Rest Of Us, I complete my coup to take over the podcast. I kicked Mike off and I’m going to be answering listener questions on my own. This is Startups For The Rest Of Us Episode 360. 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 and I’m here to share my experiences to help you avoid the same mistakes we’ve made. This is a milestone in Startups For The Rest Of Us history. Funny thing happened, as I was planning the podcast this week, I actually wasn’t able to make our normally scheduled time, nor was I able to make several other times that Mike tried to meet up with me to record the podcast. As a result, I proposed that I find a guest. I contacted a couple of guests and neither of them could make it this week. Frankly, the week became pretty crazy. There’s some stuff going on on the personal side that I’m sure we’ll talk about in future episodes as they unfold, but suffice to say it was me basically running from work to home, back to work, back to home, and didn’t check email for a few days.

Before I knew it, it was Friday morning and poor Josh, our editor, was expecting a podcast recording a few days before that. Here I sit with about an hour to put out a podcast episode and I wanted to go through listener questions. I always have thoughts and opinions on the questions that come through and I have done a few solo episodes over on the podcast I do with my wife, zenfounder.com. I figured I’d give it a shot for Startups For The Rest Of Us as well, it will be an interesting experiment. We’ll go through basically our entire backlog, I think we only have four, maybe five for today. I want to talk through the questions and comments, and we have a voice mail as well, and then lend my thoughts on those.

Our first email comes in from someone who prefers to remain anonymous. The subject line is, “THANK YOU. Finally launched, first 24 hours were an awesome success.” He says, “I’ve been to several MicroConfs, three of the last four years in the US, and I’ve been a long time listener of the show since Spring of 2013. After a few different projects and non-starters, last October, I re-focused and went back to what I’m good at, video based, on-demand training. Today, I concluded a 24 hour special launch offer to my subscribers. My first ever launch, and first time taking payments other than as a contractor. After my 24 hour email launch, I wound up with over $100,000 in sales. This was a lot of work and a lot of fun getting ready for launch, including dealing with Hurricane Irma. I wanted to express thanks to you guys for everything you’ve done for micropreneurs like me. I just put the wannapreneur out to pasture. Cheers.”

As usual, we love success stories like this, and this is why Mike and I started the podcast while we run the conference and really why we have Founder Cafe, our online membership site, foundercafe.com. This is the part about making a difference. It’s always interesting to me. I haven’t tended to start companies to make a difference, I’ve tended to start companies to serve a business purpose, to serve a need, and to make money. Whereas the blog, the podcast, the conference, Founder Cafe, just everything, the book, everything that I create, my content, that’s to actually make a difference. I know we make some money from it, but I’ve in my life made ten times more money from actually building software startups, products, and websites for that matter, than I have putting content out.

I know some people want to start companies to make a difference, there’s this Steve Jobs ‘I want to put a dent in the universe’ or you see a lot of folks in Silicon Valley saying they want to change the world with their startup. Personally, that has never been my aspiration. Yet, I have wanted to change the world in some fort or fashion. The fact that the podcast and MicroConf helped this person get to $100,000 in sales in the first 24 hours of launching, and obviously they built up to that. They had a subscriber list, this isn’t some cinderella story of them just putting something out and it’s selling $100,000 in 24 hours. They put in a ton of work, probably took a few years of building a list. I got to say, that’s the way to start the stair step. Congratulations.

Our next email is a question about launching a book as part of the stair step approach. It’s from Arthur Johnson and he says, “Hey Mike and Rob, it was pretty funny for me when you released Episode 350 featuring a listener question about launching books the exact same day I launched my picture book for kids. It’s called The ABCs of Programming. Like Dan, the author of the question, also thought writing a book was the best way to get started on the stair step approach. It’s a simple product, and unlike a SaaS or one-time software, you don’t get bogged down in the code. This has let me focus on learning process, marketing, and advertising. Since both of you have books, do either of you have any tips on launching a book, specifically if you’re doing it at step one of the stair step approach? Thanks, Arthur.”

I think books are a fantastic way to get started on this precisely for the reason that he said. You don’t get bogged down on the code, you also don’t get bogged down in support, and bugs, and all the stuff that goes along with the complexity of code. In addition, people buy more books than they buy software. I buy one or two books a week probably, either physical or audio, and I read most of them. Most people don’t. A lot of people buy a lot of books with the aspiration that they’re going to read them and consume the content eventually and they don’t, whereas people less often buy software out of this excitement to learn something. They typically buy it only when they have an actual task to accomplish.

Something like the ABCs of Programming or anything that’s going to teach my kids programming or make them better at something, entrepreneurship, learning how to manage money, I’m all in on these types of things, especially if it’s written by someone who is putting it on Indiegogo, KickStarter, or someone who I can tell has a lot of love and care for that thing; it’s not just some big publisher putting a book out, but it’s actually an individual who probably has kids themselves for example.

Yes, I think this is a very good idea if you’re thinking about it. I would go to Kickstarter myself, that would be the first thing. There’s a network effect there, there’s a lot of people on there, a lot of them have kids. It’s just something that whether you’re launching a book to kids or not, it’s probably beside the point, but you get the idea here. I’m on Kickstarter a couple of times a week and I’m looking for projects that are interesting and relevant to me. If it can teach me a new skill or teach my kids a new skill, or is kind of a new and unique thinking around a gadget, that’s the kind of approach that I personally would take.

Obviously, if you have your own audience, there’s another approach there. It doesn’t sound like you do, but that’s where you get that network effect from Kickstarter. It’s pretty easy to promote and you’re basically pre-selling, so as long as you have the cover and a few pages, you don’t even have to have printed the thing, you have several months after that to go get it printed. You can go to one of the print houses that are in China that will print hard cover books and you can ship them back here.

Whereas if you pre-launch on your website, there tends to be a little more skepticism about whether you’re actually going to deliver it. I know there are some Kickstarter projects that have never been delivered, but it’s more often than not, especially the high profile ones, they’re gonna deliver something eventually. There’s that confidence level. When I back something on Kickstarter, I do assume that eventually it’s going to come out one way or another, even though Kickstarter does say that it is not a store.

I’m trying to think—I’ve backed probably 150 projects, I have to look at the exact number. I don’t know if there’s one that I’ve never received, there is one that I received probably two years, two and a half years after it was supposed to arrive, and it came just like two weeks ago. I was very surprised by that. But a lot of things like the books, the author, it tends to be a passion project and they tend to be mostly done with the book at least in writing it and getting part of the art done, there’s not a ton of risk in that not getting done unless someone just totally flakes on it.

All that to say, I think launching a book, I would go for that. A Kickstarter thing to get the network effect, and then beyond that of course you’re going to put it on Amazon. I even debate the amount of effort to set up a solo landing page these days for a book like this. I probably always would personally, especially you can get the square space theme or WordPress theme, gets them up there with the gum road purchase button but the advantage of having channels like Amazon or Kickstarter I think is a big deal.

In addition, since it’s called The ABCs of Programming, I might even think about a little bit of Amazon SEO where The ABCs of Programming for Kids is going to get you to rank for that term ‘programming for kids’ because I know that I’ve searched that title, that phrase, probably ten times in the past year just looking for different programming books for kids because I want to teach my kids how to program, I want them to learn. You don’t have to go too far down that road, but it is interesting to think about when you’re one of these big, essentially it’s a search engine.

Google is the largest engine, YouTube is the second largest, and at one time Yahoo! was third and I’m not sure that’s the case anymore. Amazon’s got to be up there in terms of search traffic, and certainly for commerce search traffic, I can’t imagine it’s not number one. Then there’s app stores as well, we’ve talked about the Android App Store, it’s the Google PlayStore now, the iOS App Store, and all those things. These are all search engines where you can get in the line of sight of search traffic. If you are just a little bit clever or a little bit deliberate about thinking through some keywords that people might specifically be searching for—and you don’t want to jack up the title of your book of course—if you think Programming For Kids, and that actually works in this title pretty well, that’s obviously something I would think about as well. I hope that helps, Arthur. Thanks for your question.

Our next question is a voice mail.

Michael: Hey Rob and Mike, Michael Needle here. I’m currently launching [alltheguides.com 00:10:02], an online platform that innovates on the current process for booking and outdoor adventure guides. Before I get to my question, I want to say that I love, love, love the show, thank you guys for all the insights you provide. I found the show a few months ago and I’ve basically gone through all the episodes available on iTunes, really been helpful so far.

In Episode 262, 13 Signs You Should Kill Your Idea, one of the signs is that you’re building a two-sided market, which is exactly what I’m doing. Knowing how difficult this could be, what hints or suggestions do you have for someone who’s committed to doing this exact thing? Any best practices you’re finding in product-market fit, testing traction channels for both sides at the same time which is generally building this type of SaaS app. Thanks in advance for taking the time on this question and thank you again, so much, for producing the show.

Rob: This is a good question. I’m glad that you asked this. There’s a lot of questions about two-sided marketplaces that come through. They are one of those things that once you have a network effect, they’re very powerful, but they’re so hard to get started especially if you’re not raising funding, very, very difficult to pull off.

Two-sided marketplaces, the key is that you have to focus on one side of the market. One side of the market is going to flock to your site once you have the other side and you need to figure out which side to get first. For example, you look at GroupOn, two-sided marketplace. They had to get a bunch of retailers on one side and then there are consumers on the other. Zero consumers will come to that sight until you have some deals, some retail deals. You can promise them deals, you can probably start building a mailing list, but what you really need to do is you need to go out first and you need to get enough retailers on the site that you can start bringing consumers to it.

Once you get a big swath of consumers, you get that snowball going, it’s so much easier to recruit the retailers. You do a little on one side, just enough to get the other side to snowball and avalanche. Once that avalanches, then the second side will be a piece of cake.

In your case, you’re looking for both. Guides, and you’re looking for people looking for outdoor adventures. The strategy I would take is I would—you have even a third channel because this is geographical. It’s not like eBay where there are buyers and there are sellers and they can be anywhere in the world because of the postal service, you have guides and you have consumers. Much like Uber or Lyft, you also have a geographic thing because they need to be together in the same place.

The first thing I would do is geographically limit this and I would pick some type of tourist place, look at them. Number one outdoor adventure spot in the United States. I don’t know if that’s going to be in Colorado, if it’s in California somewhere, but pick that and pick a 40 mile radius or one town and make it work there.

This is what Travis and his co-founder did with Uber. I only keep bringing Uber up because it’s a parallel story of what you need to do to what they did, and they did only black cars, they did only San Francisco. At the start, I’m pretty sure it was one or two of them literally driving black cars, they rented black cars and they were driving themselves just to figure out if this thing would work, and then they started recruiting the black cars. You needed enough black cars that then you could recruit the other side of the deal, the consumers in essence. And then when you had a bunch of consumers, you can get black cars automatically because the black cars want the money. It’s like this back and forth.

For you, I would do the same thing. I would pick a small geography, I would get 10 guides or 20 guides on the platform and they’re going to be the people who are willing to take a flyer on you. I was going to say you can give them a special deal but I don’t even know if you need to, I think when you say that you’re gonna be Uber for outdoor adventure, some people will think that’s cool and some people won’t.

Maybe you talk to five or ten guides. For every one you get to sign up, that’s okay, this is the hustle. You talk to 100 guides, you get 10 or 20 on the platform, then you’re going to go out and you’re going to just blanket that area and you’re going to blanket that internet with whatever you can do, whether it’s Facebook ads, Google Ads, whether it’s retargeting, whether it’s blog posts, whether it’s posting in forums. That’s the online stuff.

And then the offline stuff, assuming people living in that area also need it. I don’t know if everyone’s just flying into town, then offline won’t actually be that helpful. Where are people going to be located locally when they need a guide, are they going to be in REI? Is there a bulletin board in that REI? You can post a flyer or you can post your flyers on the counter at a local outdoor place, or you can make a deal with five of the outfitter shops that they will pitch you.

I don’t know the system, maybe you’re in direct competition with the outfitters and that doesn’t work but you get the idea. It’s like think locally, where would someone be located when they’re looking for this or when they’re thinking about it? There might not be a ton of local opportunities, maybe it’s all online. You got to try both to know what’s going to work and what’s not.

To summarize, I would geographically limit yourself and then I would focus on one side first and that’s going to be really, really hard to get and get just enough that it’s minimally viable, and then I would launch on the other side. You’re trying to bring in all the consumers to basically book the guides that you’ve signed up. You’re taking a small percentage of that, which is the challenge of this thing. Until you get to thousands and thousands of bookings, taking your 10%, 20%, 30% fee, this isn’t going to amount to much. You are definitely going to have a long road ahead of you, but I do wish you good luck on your journey.

Our next question comes from Chris Portier. The subject line is Pet Projects and Learning. He says, “Hey guys, first off, love the show. Been listening for about three to four weeks now on my commute to work, it’s amazing, props to you guys. I work in marketing for a Fortune 50 company and I love what I do, but it isn’t quite aligned with what I want long term. I love learning and I learn best when I have an idea, a theory, or a best practice to put to test in an application. I find it hard to find something that I can do on my own. I really want to learn and work my way up the project ladder to something that is sustainable/impactful. What things could I do/steps could I take to do smaller scale projects where I could take my learnings and put them into practice? Thanks guys. For reference, these are things like best practices, video techniques, targeting techniques, data analysis, and pretty much a little bit of every gospel of marketing.”

I think, Chris, you haven’t heard me talk about the stair step approach to bootstrapping yet and I’m not going to go through it here because it’s like a drinking game at this point, every time I talk about stair stepping, everybody takes a shot. I would recommend a couple things that one, you go search Google for the stair step approach to bootstrapping. You should find a blogpost on my blog, softwarebyrob.com, as well as a prior, at least a couple prior episodes, of Startups For The Rest Of Us. Listen through that and it should give you ideas about how to take something that you can do and launch something.

Whether it’s a book or whether it’s a WordPress plugin or whether it’s a video course, it’s something small. One time sale, typically a single traffic channel, that single traffic channel might be SEO, it might be people finding you in Amazon, it might be you have a small email list even at 500 or 1,000 people, and you’re not going to get rich off this but you’re going to learn so much. You’re going to learn how to make money on a project or a product like you’ve never done before. When you’re used to trading dollars for hours, that first dollar that comes to you that is from something that you made and just made a copy of is incredible, it is life changing. I say that with no exaggeration. It changed my life.

When I see people email in about their first sale, you can tell that it is life changing even if you only make $500 from this first product, it is incredible. The confidence that gives you, the experience you get, you learn what’s hard and what’s not, and you learn what you like to do and what you don’t. Maybe you learn this isn’t for you at all and you just want to be a higher paid, salaried worker, or you want to be a higher paid consultant. That’s a good lesson to learn. It’s a good thing to know instead of sitting there for years pining away thinking that the entrepreneurial life is for you. Odds are, I think once you make the money, you’re going to realize boy, I want to do this again and again and again.

That’s the stair step approach, it’s stepping up from one thing to the next, to the next, and doing what you love. If you’re motivated by learning long term, entrepreneurship is for you. Thanks for the question, Chris. I hope that’s helpful.

My last question for the day is a fun one and it’s from Brad. He says, “I hope you’re well. I’m taking a stab in the dark, I’m writing a blog post for my website on what it takes to be a successful podcaster. I was hoping you’d take a few minutes to add your comments.” He has a forum and I may or may not look at it, but I just thought it was an interesting question.

We do get this now and again of how do you launch a podcast, how have you guys become successful, how do you handle this, how do you handle that? I think the bottom line that I’ve realized is that you can hack initial growth of a podcast, I see folks doing this, I think it’s good, I think it’s basically kind of like doing SEO for iTunes in essence. You launch your podcast, you email your list, you get everybody to download it, and then you catapult to the top on New & Noteworthy. And then you got to build momentum from there.

That’s a great way to launch. That’s a tactic. What I’ve learned and realized through my experience and the experience of watching other people launch a great fanfare and some of whom have stuck around and some haven’t, is that it’s about showing up every week or twice a week or three times a week. It’s about showing up. It’s about relentless execution, which is a phrase that I use often. I don’t know any other way to build a large podcast audience other than to put in the time. You look at the largest podcast in the world, you look at Serial, you look at This American Life, you look at StartUp and The Gimlet Shows. You look at the Tim Ferriss Show.

You look at whoever else, Stacking Benjamins, they put out either a show a week, some put up three shows a week, but they put in time. You know that although Tim Ferriss is the four-hour workweek guy, you know he’s spending a ton of time prepping those guests, booking guests, I know he has people helping him do that for sure. He ships a show or two every week. He didn’t just rest on his laurels and his name and ship a podcast and then not record again. There is an aspect of being entertaining, providing value, and all that stuff. Yes, table stakes. You look at This American Life, amazingly entertaining.

Also, hundreds and hundreds of person hours per episode, but they show up. They ship an episode every week. I think that would be the first takeaway, don’t think that you can do it sporadically, you can do it as you feel like it. At this point, shipping weekly is now table stakes. I think two or three times a week is going to be even better, you’re going to build the audience faster.

The other thing that you should think about is there are really only three values or three pockets of value you can get from a podcast. One is entertainment, two is relationship—it’s a one sided relationship but there is a relationship. The third is tactics, how to. Let’s cover each of those a little more in depth.

You think about entertainment, this is This American Life. That’s a great example, Serial as well. You don’t listen to it because necessarily you have a relationship with anyone in the show or you feel the people in the stories on a long term, ongoing basis. Maybe you might listen to this podcast, Startups For The Rest Of Us, you might listen to Jordan and Brian on Bootstrapped Web. You’re following along on the story, it’s the journey of acquiring HitTail and selling it and launching Drip and being acquired by Leadpages. You listen to Mike go through Audit Shark and through Bluetick and his launch. Over time, there’s a narrative. Again, same with Bootstrapped Web, you follow along on their journeys of launching things. That’s the relationship side of it.

There’s a little bit of entertainment but it’s mostly because you like the people. That’s not how I feel with This American Life, although Ira Glass is obviously an amazing talent. I don’t necessarily listen to it because he’s the host. If they still put out the same quality show and someone else was hosting it, I would listen to it. I’m not sure that I would with Bootstrapped Web because I know the people, same thing with The Art Of Product Podcast. It’s Ben Orenstein and Derrick Reimer who’s my co-founder of Drip. Same thing, it’s their journey and you’re following along as they’re launching and building products.

I don’t want to get confusing here. What I’m saying is that the entertainment piece—I can listen to a comedy podcast, I can listen to a podcast about roleplaying games, and it’s just fun. It’s something to take my mind off of real life, in essence. That’s one thing you can do. If you’re good at that, do that.

The second one is the relationship and that’s building up a long term narrative that people really want to hear. You maybe could say a little bit that Serial is like that, although it’s more the story that you get tied to. Obviously, Sarah Koenig, the host, again if suddenly next season she was not the host, I would still listen to Serial because it’s a good show. For me, that, again, is more about entertainment.

The relationships are when you really start bonding with the people and their stories. If you met them in person, you would feel like you knew them. You can tell, man, I want to be this person’s friend, or maybe I don’t want to be this person’s friend but they’re interesting to listen to. I think sometimes folks listen to Marc Maron which is the WTF Podcast. There’s a bit of entertainment there.

There’s also the ongoing relationship of what is Marc going to do next. If you’ve listened to him for years, you’ve seen his whole journey from the depths of being an interviewer on a small podcast to having his own TV shows come out and really launching himself into fame. There’s a relationship aspect. That’s where the entrepreneur journey that’s going to take years is designed pretty well for that.

The third is the tactical piece. I think tactical can get you started, it’s what gets an initial audience going if you have no name because just coming onto a podcast and starting to tell your story isn’t that interesting, typically, especially if you’re just getting started and you don’t know what you’re doing. A lot of times, something tactical can be there to help people justify listening to it.

When I say you don’t know what you’re doing when you’re just getting started, you certainly know something. If you’re doing anything, you can talk about the experiments you did that week with SEO or AdWords, and then you can put out a podcast about here’s how I failed at AdWords. That becomes something that people can learn from.

Long term, this is feedback we’ve gotten about this podcast, if you listen to 350 episodes of this show, the tactics at a certain point aren’t that helpful anymore because you’ve gotten so far past where tactics are helpful, if that makes sense. I know that for me, a few years into my entrepreneurial journey, most of the podcasts I listen to that talk about five ways to do this, ten ways to do that, had very little value, had tips here and there, and I would always note them down. They had so much value upfront when I was just learning.

When you’re a beginner, you’re just thirsting for knowledge and that would help me, and I’d make notes, and then I’d go in and I’d implement him and I’d see what worked and what didn’t. As time goes on, more of the tactics come from your peers, from mastermind groups, from in depth conversations with friends and colleagues from attending conferences like MicroConf or BOS and getting new ideas from a really crafted one-hour presentation, from trying things on your own, and honestly still from podcasts. I don’t want to downplay that, that even though we put out 350 episodes or even though Conversion Cast has 100 episodes or whatever, trying to think of some other—I used to listen to some SEO podcasts. I still would pick things up because things do change and people try and do interesting things.

I think having a mix of probably two of the three that I just named which are entertainment and the relationship which is kind of long term narrative, and tactics. Having two of those three, you can pick any two, frankly, I think is a good combination to have. Then, just relentlessly executing on it and shipping every week. You’re going to start out pretty crappy, as Ira Glass says, it’s hard to get started creating any type of art because your taste is up here and your ability to produce that art is way down here.

It’s painful to hear yourself write a song or play music or produce a podcast or build a business or write copy or speak on stage because you know what it means to be good at any of those things and you’re going to suck at it for a long time, but you have to suck at it over and over until you get better. Eventually, you will see yourself on stage or you will listen to a podcast episode, or you will look at copy that you wrote six months ago and you will think to yourself that is badass, I’m good at this now.

That’s what relentless execution gets you; it’s showing up everyday and it’s doing shit that scares you.

I’m going to wrap up this episode. I think it’s funny, I don’t actually know if Mike’s going to listen to this, I don’t know if he listens to the show after we record it. He may never know unless you email and taunt him or post a comment, don’t taunt him I’m just kidding. You should totally let us know if this was an interesting format at all or if you feel like eh, we should have two people, I don’t know, I’m just curious. Now and again, it’s not like we’re going to plan to start doing a solo podcast episode, it really, truly was an emergency thing and I wanted to have new content out for you guys next Tuesday but would be interested to hear your thoughts.

You can email us at questions@startupsfortherestofus.com, post a comment on the website at startupsfortherestofus.com. This is Episode 360. You can also call our voicemail number at 888-801-9690. Our theme music is an excerpt from a song called We’re Outta Control by MoOt who was offered up under the Creative Commons license.

It’s actually interesting, go to YouTube and search We’re Outta Control by MoOt and you can hear the whole song, I’m sure they’re in Spotify as well. It’s kind of a trip when you hear it because you’ll hear the intro which is the part that we use. And then when he starts singing the verse, it’s so weird for it to continue and not to fade out after hearing our version hundreds and hundreds of times.

If you’re not subscribed to this podcast, you can search in iTunes or Stitcher, Down Cast, and search for Startups. We’re typically in the Top 3 or 4. You can get a full transcript of each episode at startupsfortherestofus.com.

Thank you for listening and I will see you next time.

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2 Responses to “Episode 360 | The One Where Rob Takes Over the Show”

  1. Rob, Wow! Thanks for the extra effort getting this episode out. Always great to get great information and inspired EVERY Tuesday. Thanks again.

  2. Hey Rob…

    Sorry to hear you are having some issues personally…

    Thanks for delivering this one… In fact I really liked the setup of this where you simply answered listener questions…

    Would be great to have a listener questions episode once a month or something depending on your backlog?

    Thanks again!