Show Notes
In this episode of Startups For The Rest Of Us, Rob and Mike ask the question: should you love what you’re working on? The guys talk about this topic in the idea of balancing interests and opportunity. They also ask themselves the question and how it pertains to their lives and businesses.
Items mentioned in this episode:
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 built your first product or just thinking about it. I’m Rob.
Mike: And I’m Mike.
Rob: And we’re here to share our experiences to help you avoid the same mistakes we’ve made. Where this week, sir?
Mike: I started a local D&D meetup group.
Rob: That is so cool.
Mike: A friend of mine and I’ve played with our kids. I’ve got two sons and he has a son and two daughters. One of his daughters played a little bit with us. She was like, “Yeah, this isn’t for me. I hate this. I don’t want to deal with boys.” I think that’s certainly what is was. But the other three, him, and I play. We wanted to start up a group where we’re actually playing with adults because kids can be a little bit difficult to keep on track sometimes.
He knew a couple of people then I started a meetup.com group to try and find at least one more player. There’s five of us now and we’ve met for the first time earlier this week. Started up a game, we expect it to go for a couple of months, we’ll just meet up every week, and see how things go.
Rob: That’s fun. Did you say you just meetup.com?
Mike: Yup.
Rob: Awesome and you’re playing fifth edition?
Mike: Yeah, the latest version. I think two or three other people who we’re playing with haven’t played in 20 or 30 years. Then they went to college, had kids, and got out of bit for a while. Now they’re coming back and so far it’s been good. We only had one session, which was about three hours long, but we spent some time before that at a different time creating characters. It’s good so far.
Rob: Were they marveling at the ascending armor classes and there’s no THAC0. I don’t know if you played second edition, but did they have to read the player’s handbook or you just brought them up to speed verbally?
Mike: Yeah, I caught them up to speed. I was like, “Here’s the differences from when,” because I asked them which versions they played. So up to second edition they have the THAC0 and then in the third edition they switched over to the d20. I just explained those things.
Then one person, he still plays a lot of version 3.5. He’s never played 4 or 5 before. I looked it up and found a place—I think it’s Reddit—where they basically laid out, “Hey, here are the differences between version 3.5 and version 5.
Rob: There’s a lot more similarities than I thought. I know 5 is more stripped down. There’s less feats and there’s a bunch of stuff there. The prestige classes I think are maybe those are only in 4. I never played 3.5 or 4, but I’m pretty familiar with them at this point.
I know there’s always controversy around it, but I played basic, I played expert, then I played first edition. Then I just got familiar with second edition, which is where they introduced THAC0. Pretty sure first edition it was all table-based, is my memory, and then stopped, got into sports, music, and stuff, and then just came back into it as my son got old enough to play.
I remember my nostalgia is for basically probably first edition, maybe basic but the rules are so jenky there that I couldn’t go back to it, but I remember Googling, I’m coming back to D&D. Should I try fifth edition or should I go back to first edition?
There’s all these discussions about it and the general consensus was, especially for bringing new players who’ve never played anything before, bring them to fifth edition. It’s a pretty nice rule set. It’s honed and refined. It’s like a piece of software that’s gotten better. I think there was bloat, perhaps.
People could argue as you got 3.5 and 4. Mostly 4, I think people had some issues with, but then 5 was almost like a partial rewrite or something, or someone refactored a lot of code, added some unit test. It’s a terrible analogy, I don’t want to get into this, but I really get them. When I dove into 5, I was like, “This is a really fun game to play.” It’s so much less about the mechanics of the game, which was my memory of the first edition. All these tables I was looking up and all that stuff. It’s so much less about that. It’s more about getting into the characters, the combat, the adventure, and the fun of it. It was cool. I taught my son I think when he was seven or eight, and he picked up the mechanics pretty quickly.
Mike: I really liked what they did with the fifth edition as well. It’s just so much more streamlined and it’s simpler without being simplistic. That’s probably the best way I would describe it. And you’re right. There’s a lot less reliance on tables and the one thing that I really liked that I’ve read about, which is the difference between 3.5 and 5 is that in older editions, there was a lot of reliance on stacking things to get more powerful.
You’d stack your armor and various other things. In this, you don’t have really have to do that and for the most part it’s just like, “Oh, you have advantage and you get to roll 220 set of die and take the best one.” That’s great except when, as an example I was explaining to these guys like, “Hey, this is what it looks like,” and I rolled 220 and I rolled a one and a two.
Rob: For us, we’re recording a little bit in advance but if all goes well, we have closed on our new house in Minneapolis and frankly, all of our stuff will have been moved because the move is scheduled for just a couple of days after. We’ll be in the process of unpacking boxes and probably hanging things on walls. I’m really looking forward to having that process, the chaos ending because already, I’m sitting at our old house and there’s things off the walls and there’s a few things in boxes.
Everyone is a little bit disjointed. You get that feeling of like, “We’re in process, where was that one thing, I can’t find it,” or it’s even just a visual cue. There’s just some chaos around me and there’s this unsettled feeling I feel like with every family member being in a place that feels like our house but it’s a little different because there’s nothing on the walls as an example. I’m looking forward to feeling better about that.
Mike: Like an Airbnb where everybody moved out and you just walked in.
Rob: Yeah but even worse than that is, it’s our house that’s familiar. Everything’s packed up and stuff. It will be good, but it’s definitely move up for us in terms of the house is bigger and nicer, and we can do things. I’m already looking at what smart home things I’m going to install because we have several Amazon Echos and there’s all the controlling you can do.
Even starting simple stuff like light switches and getting more advanced with security stuff, operating garage door openers, and that stuff. So I’m kind of nerding out on that a little bit. Something I haven’t able to do because all that stuff, I’m not going to invest time in that in a rental, and it really hasn’t come big time into fruition. It’s been a couple of years since I’ve owned a house now, so I’m excited at the potential of geeking out with some of that.
Mike: On my end, the only other thing I have as today, I recently fixed a Javascript bug that would sometimes prevent people from logging into Bluetick. But not all the time and I could never replicate it which sucked.
Rob: Now that sucks.
Mike: It had to do with angular promises with the Javascript and one would trigger and it says, “Oh, go ahead and log in,” then it goes to grab all the data and it doesn’t have the local token saved. It was just a matter of it didn’t fully save it before it had actually tried to reach out and grab all the data that it literally just authorized itself to get.
Anyway, just because there was the race condition, like it worked fine for just about everybody and then there were, I think, it either certain browser combinations, or I couldn’t even nail it down to, say it was just this operating system and this particular situation. If the latency tended to be high enough, then it tended to not work.
Rob: That’s tough, Javascript stuff. Still, a client said Javascript is still so hard. I shouldn’t say so hard. It still has those edge case things where the browsers handle it differently and if can’t reproduce it, how do you fix that stuff? Every once in a while, that’s the thing. Again, if you have 10 users, it’s unlikely that someone happen but when you get 10,000, 30,000 people using your app, bizarre edge cases come up and you just some oftentimes are completely unable to reproduce it. If you can’t reproduce it, you pretty hard to fix it.
Mike: In this case, I went down the path of looking. In Chrome, there’s this ability to say, “Oh, use a different emulator if this was running on a 3G connection or something like that, or even slower.” Even though I still could not replicate it, I’m pretty sure that it had to do with certain types of browser combinations and what other plugins you have loaded. Based on those things, it would either trigger the race condition or it wouldn’t. Sometimes it would work. Actually, the vast, vast majority of the time, it would work fine and then just these little occasions where certain things would be screwed up and it just wouldn’t.
Rob: So cool. Today, we’re going to kind of, I don’t know if it’s a thought experiment as much as it’s a discussion of this topic that come up now and again. I’ll say, not even an inflection point but at a point where I’m thinking about, “Hey, what could happen next for me? What’s going to come next?” I know there are a lot of people are thinking at a given time length, “Hey, what project am I going to work on?” and, “What type of niche should I go after?”
There’s always this balance between balancing your interest in something and the opportunity that it has. I think the question we want to explore today is, do you need to love what it is you’re working on and what that looks like? You can take a business that sells beach towels online, and you could say, “Well, beach towels are awesome and I’m really into them and I collect them and I’m super interested in it.” Or you could say, “Well, I’m not interested in beach towels, but I am interested in ecommerce and ecommerce really excites me.” So you have that interest. Or you could say, “Well, I’m not that interested in ecommerce but I am interested in just running a business, and this is one that I can do in my spare time.” So you have interest there, or it’s kind of a continuum. Or further up, you could say, “I’m not even interested in running a business, but I just want the freedom that it provides.”
One of those four places on the continuum I think is what we’re going to look at today and balancing on one end, there is interest and then on the other end of that spectrum, there’s opportunity. I think potentially if you can get them to overlap, maybe it’s less about two ends of a spectrum and more about, it’s a Venn diagram where you have circles. The circle could be, these are all my interests and that includes role-playing games and it includes stock market investing and it includes Legos and I don’t know, other things that someone might like. Running a business might also be one of those.
An opportunity could be things that overlap with those, like, “Hey, there’s a real good opportunity starting at Lego RPG site that no one’s done and you can make much money at it.” That’s not true because you probably wouldn’t make any money. I know there’s a bunch of opportunities like selling dog food online or starting a business you have no interest in and you got to figure out and evaluate for yourself which of these are you going to go after? How are you going to balance those, I think is a better way to put it.
Mike: You mentioned Venn diagram in there. I think the one misleading thing about using the phrase Venn diagram is most people think of it as this mechanism for overlapping either two or three things, but when you start adding more than three things in, it’s almost like more of a three-dimensional model at that point. It’s still a Venn diagram, but it’s just really much more difficult to visualize because some of those things just don’t overlap at all or they only overlap with everything but it’s also difficult to put them in if it’s actually like a 3D model.
Rob: I think that’s a good point and a Venn diagram or a continuum, a single line, an axis was one thing on one end and one thing on another. These are just really abstractions. It’s ways that we can describe things and at certain points abstractions always break down. I think that is something to keep in mind as we talk this through.
There’s a lot of folks and there’s a lot of conversations that I’ve seen around this idea of should you follow your passion or should you just go after the opportunity. People try to make it binary and they say, “Well, if you just follow your passion, you’ll get there.” Or you purely have to go after opportunity and I believe the conclusion that we’re probably going to get to is that it’s a blend of those. It’s figuring out what you can be passionate or interested in, but also blend out with something that held some opportunity.
To start to think about it, there’s this question that I want to throw out, what drives you? You can answer that in the abstract or you can take a personality test. Have you ever taken the enneagram?
Mike: I don’t think I have, no.
Rob: We’ll link it up in the show notes. You can take it for free online and it’s like the, what is it the Myers-Briggs where psychologists like Sherry says, “You know there’s some value there, but it’s really not scientifically a research.” Perhaps as a psychologist, I would take it with a grain of salt versus a true psychologist-administered test. But there is still some value to these things. I even think StrengthsFinder 2.0 I think is good. It gave me some insight and a little more insight into who I am even if that’s not the most academically rigorous test of anyone.
The reason I bring up the enneagram is you basically take this test online. I think it takes about 20 minutes and then it gives you a couple of numbers, it’s one through nine, and each number corresponds to a personality type. Number three is an example, a lot of folks that I have met in business wind up with this and this is the achiever. There’s always pros and cons and it says the success-oriented pragmatic type, adaptive, excelling, driven, and image-conscious.
I think some startup founders are driven by the achievement. They just want to achieve whether they’re trying to fight this voice in their head. It’s the voice of their father, or the voice of someone who told them they can never succeed, or maybe it’s just a drive they have to make money, maybe it’s just a drive to show everyone or show themselves that they can do it.
But there’s something about just doing it for the achievement’s sake. They don’t necessarily, in my experience, care about the process of getting there, about what they create along the way, or about they could achieve in a business that sells cell phones, or is a GPS startup, or is selling whatever, beach towels online, but if they built an eight-figure business in any of those, they would feel they have achieved something and they’d be happy.
Versus, I believe it’s number six, and I think that’s me. It’s the loyalist. It says the committed, security-oriented type, engaging, responsive, anxious, and suspicious. A big part of the loyalist, when you read through the description is, there’s this sense of creating and needing to create something, put it into the world, to own this creation, to advance it, and to make it interesting.
What was funny is interacting with some folks once Drip was acquired, interacting at leadpages. Several of us took this test and it was pretty obvious there were folks who, it didn’t matter to them what business we were in. They just wanted to go big. Going big for the sake of going big was awesome to them.
For me, it was like, “No, I’m actually here to build stuff.” I’m a banker and I am the guy who writes books, I’m the guy who creates podcast, and create software, and builds interesting things, and hopefully, that’s why I want the money is so that is can go work on these interesting things. It’s to have the freedom to go do interesting things. Not just achieving for the sake of achievement.
Mike: You definitely fit that loyalist. You’re definitely a suspicious and shady-looking guy.
Rob: Hey it is, huh? That’s the thing. When you read any of these, there’s always some negative and it’s like, “Oh, am I really?” And it’s like, “Yeah, I probably am.” I’m probably am all those things. But engaging and responsible certainly fits as well.
The reason I bring the enneagram up is that you can take any number of test, but it’s interesting to spend 20 minutes and get some insight, to read the descriptions and think, “Am I here to achieve?” Because if you are, then your need to love the business or the specific niche, or whatever it is that you’re working on, is probably going to be a lot less than someone who needs to love what it is that they’re working on, and to be enthusiastic about it.
Number seven is an enthusiast. There’s others of these numbers that really point more towards like, “Yeah, you need to love what you do or else you’re going to bail on it.” I think it’s interesting whether you take this or you just think about it to yourself. Certain people know that there’s no chance that they’re not going to be happy working on something that they’re not super interested in everyday.
Mike: I think in general when you take a look at these types of personality tests or things that will help to describe or categorize you, it’s easy to write-off the 20 minutes that it takes to do any one of these and as you said, I think that if it’s not something that it is rigorously given or tested, like if it’s a 15 or 20-minute test, it’s not going to be rigorous.
If you spent an hour answering questions and you’re answering 60, 100, 200 questions or something like that, it’s a little bit more. Those you probably have to take with less of a grain of salt, but regardless which one you take, I think you’re better served by looking at the results of it as in how far you skew in a particular direction, regardless of what direction that actually is.
As you said, every single one of these has pros and cons associated with it. People who exhibit different traits are going to have different interests and they’re going to dislike different things. But when you’re going through those, it’s important to not just take a cursory look at those, like the different personalities or different categories that they could potentially lump you in, and then not even take the test, because taking the test itself is going to tell you how far you skew in one direction or the other.
I can look through these nine or right here for the enneagram and I can probably say, “Oh, well I associate with four or five of them, or even six or seven,” but it doesn’t tell you how strongly you associate with them, and that is even more important than being able to put yourself in one of those categories.
Rob: Yeah, I would agree and I didn’t mean to downplay this from the start. When I say I take it with a grain of salt, I mean, don’t base every life choice on your enneagram result. The enneagram is given to tens of thousands, hundreds of thousands of people. It is research-based and it is like a viable test. But as you said, when it’s only asking so many questions and it’s 20 minutes, there is less rigor there than a test that is. A lot of the psychological battery tests that are given, you’ll sit there for two, three hours for them to get a full picture of stuff. It’s just a nice taste and a nice direction.
I do think I like these things because I always learn something about myself and it’s typically something that’s a little bit of a blind side for me. Typically, I’m like, “Yup. That’s me, that’s me, that’s me,” and then they’ll throw something else in this, it’s like, “Oh, that’s true, but I hadn’t realize that.” It’s one, the anxious or suspicious thing. It’s like, “Yeah, that’s a good point.” I do tend to not trust people until I known them for a while and how is that a plus for me and how is that something that maybe I need to work around.
But I think the interesting thing and a question that’s framed is like, “Are you the type of person who can work on things that they don’t love?” That maybe the question to ask yourself. Certain people just doesn’t know this. I remember Jason Roberts on TechZing used to always say, “I know I’ve got to love it or I’m just not going to do it.” He’s very much a passion player. He would only start ideas that were super exciting to him and he could never go into a niche that was selling beach towels or he would have completely peered out.
Whereas for me, my goal of financial independence was more important to me than needing to love that I was selling the duck boat plans and the bonsai tree ebook, in the early days, the beach towels and stuff. Those are high probability of success things for me based on my tool belt and I was able to build those collectively into six-figure income and replace everything. I bought my own freedom. Then I moved more into things that I enjoyed. That’s when I started doing HitTail, and Drip, and even during that time I was seen doing MicroConf and this podcast. The stuff was part of that.
Again, I hope it’s a spectrum or if it’s a line or whatever, but I always think about this one example of, to optimize for opportunity, you could sell coffins online. To optimize for interest, if you love watching movies, you could review movies online, or if you role-playing games, you could review role-playing games online. Those two are massively in tension. The role playing games and the movie reviews is going to be so hard to make a full-time living at that. Yes, there’s a handful of people who do it, but it’s really, really hard and it’s a ton of work.
Compared to selling something that’s really boring like accounting software or coffins online. I see it partially as a joke, but I remember a venture capitalist using this an example of them wanting founders who are really into what they’re doing. This venture capitalist said, “You know during the dot com boom when everything was going online pets.com, grocery delivery and all that, there were entrepreneurs who were pitching them like a really inefficient market is the coffin market.” It’s a cottage industry, the markup is outrageous, people don’t haggle, it’s just this weird time. The guy was like, “There’s a huge opportunity here and we can make a ton of money and save money for consumers.”
I believe that mattresses are like this, too. Mattresses, the markup is always huge and then Casper has come along and I really think there’s ton of opportunity there. The VC said, “I kept asking the guys, ‘Why do you want to do this coffin startup? A funeral startup?’” They’re like, “Well, because there’s opportunity there.” The VC didn’t fund them because he believes that you need to really be into the whole space, love the space, and this and that. That’s fine. That’s his belief. That’s his thesis of funding people.
But I think when you ask yourself, you can have the continuum. You may not love mattresses or care anything about them, but if you’re really interested in building a big business, running Casper would probably be an interesting slush fund thing for you to do if you’re an achiever. If you just want to achieve, you can build that eight, nine-figure business, and really not care much about the product you sell.
Mike: I can think of any number of businesses that I would think it would be interesting to start and go for but that doesn’t necessarily mean that there’s a business opportunity there as well. I think that’s what always bugged me about the do-what-you-love advice. Just because you love it doesn’t mean it can actually make a business. That advice kind of glosses over the fact there may just not be a business there for it. I don’t know. I think there is a difference between doing it because you love it versus doing it because you want to, also making an income from it.
That goes back to the Venn diagrams that you’re talking about. There has to be a clear intersection of multiple things in order for it to work for you based on whatever your goal is. If you just want to do it to have fun, go for it. You don’t also have to make money. But if the Venn diagram includes making a full-time living from it, then the business opportunity has to support that. If it doesn’t, then it’s not going to work.
Rob: Right and some luck if few get to do both. Gary Vaynerchuk loved wine and he turned that into a business. It does happen. It’s just how many other people try to do the exact same thing and it didn’t work versus if there really is opportunity there that the odds of you, even getting a base hit and I think that’s the thing, it’s like are you willing to have a higher chance of success but perhaps enjoy things a little less along the way because you’re not doing everything that you love. Maybe you’re just going for that single or that double, but if it brings you financial freedom that you can then work on stuff you love later, but you’ve got to do a few years of not terrible drudgery. It’s not like you’re working on 9-5 for someone else, but it’s weighing those two things.
I think that leads me to a question of, “Tell me what do you love about Bluetick? Do you love the idea of warm outbound email? Or is it you love building software and want to find a way to make money from it and sustain yourself full time? Is it you love building businesses?” There’s got to be something in there that drives you day to day but I don’t get the feeling that you woke up two years ago and said, “Oh man, all I want to think all the time is email deliverability and how to hook into the Gmail API.”
Mike: Yeah, I definitely did not think of that and of course I don’t hook into the Gmail API because it doesn’t work very well. I think the thing I keep coming back to is that it actually solves a genuine business problem, first of all, and second, I like the people that I work with. Like the customers that come to me and they’re like, “Oh I have this problem and I need to be able to fix it.”
I’ve taken various personality tests in the past and one of the things that tends to come out at or very close to the top of the list almost every time is that I’m a people person. I care very deeply about a much smaller number of relationships, but people is a main focus for me. If I were to sell a business for $20 million and I was the sole stockholder, for example, I wouldn’t just keep it all. My inclination would be to share that the people who have helped get me there.
There’s certainly people who would take the opposite approach and say, “Well, I took all the risk, I did everything, I own 100% of it so I should get everything.” There’s nothing inherently wrong with that, it’s just not my personality.
There’s that side of it that I like helping other people, which partly why I do the podcast, partly why we’ve run Founder Café together and why we run MicroConf. That’s important to me and running Bluetick, I get to work hand-in-hand with a lot of different people and a lot of different businesses, and yes, it ultimately benefits me financially as well, but at the same time I know that deep down I’m actually solving a problem for them and it does help their business.
Rob: I think that’s an important thing to know. You look around at different examples. Think of Dan and Ian with Tropical MBA. I’m pretty sure they weren’t that excited about cat furniture and valet podiums, but they were excited about the prospect of freedom, about the prospect of starting your own business. Ian’s certainly a maker. He’s the designer of the stuff in the early days, and I think they’re excited just about building businesses and such. That’s that balance of they’re excited about enough things about those spaces and they saw tremendous opportunity there that they’re willing to dive in.
I felt the same way about HitTail and Drip. I have always liked SEO, I’ve done a lot of it, and I’ve always done a lot of email marketing, and use many ESPs. But I’m not as passionate about those things as I am, say, some of the hobbies that I do, such as playing guitar, or playing tabletop games, or even personal financing, and stock investing. Those hobby things are just so much harder to turn to real businesses. I kind of combined that opportunity with SEO and email marketing with the interest that I have in those topics, and then build businesses out of them.
I think that that’s probably the conclusion that I leave folks with. You may not be super excited about being on online classified ads, or about selling beach towels, or whatever. But there are other things that you can do and it’s about knowing yourself. You have Jason Roberts, again, coming back to him or someone like him. There are people out there who are just really need to love what they’re working on.
A lot of those folks become indie game developers or they build software for guitar effects. I used to work with a guy who built that on the side because he was so into the music, and that’s all he wanted to do is be around music and that’s cool. But for him, if ever he achieves financial freedom, it’s going to take decades and it’s just a lot more risk there, and a lot less chance of success because you’re stacking the cards against you in exchange for being able to be really passionate about what it is you’re working on. That’s the trade-off that you will have to make.
I think each of us as individuals has to think through that and think about how much it is you desire to work on something you love versus perhaps having more of a chance of that success.
Mike: I’m wondering how much of the decisions that people who are listening to this podcast make or just entrepreneurs in general, I wonder how much of those decisions are influenced more by what they see as a potential business opportunity versus what their interest are because I talked to a lot of people, like, “Oh, I need an idea for my app. I don’t have any ideas.” That’s a very common thing that people will say and most of the time I think it’s because they don’t want to build something that somebody else has built or build a business that is very much like another business.
But at the same time, those things can be very successful and if you have your own take on it, your own ideas about how to take that to fruition, then you can certainly make it work. But if they just don’t have those ideas or they think that they don’t have those ideas, then they’re not going to move forward with them.
Rob: Right, and if you work on a business you hate every day, then obviously, that’s not a good solution either. Honestly, when I look, I think there’s a lot of approaches. We’ve gone through them here. The approach I took was in the early days my interest was financial freedom. I just kind of slogged it away, a bunch of businesses that I didn’t have a ton of interest in, but I was learning and learning is exciting to me. I think a lot of folks in our audience probably feel the same way. Just the act of learning new things could potentially keep their interest. Then as I built more and more of those up, then I was able to go into things that I was more interested in like, let’s say HitTail and Drip, with SEO and email.
Now, I’m at the point where I have the luxury of more time to invest in something I’m working on and it doesn’t need to be that big hit. I may even sway further into, “I’m only going to do stuff that I really, really enjoy.” Maybe it is. Maybe my next thing is nothing like anything I’ve done in the past and it’s truly like, I mentioned it a little bit, “I’m going to build an authority website in this topic that I just think is super interesting, and see what happens.” Maybe I’ll spend two years on it and I enjoy it because it’s a hobby and it never does anything. So what?
Personally, I would have hated doing that 10 years ago because I would have been hating my day job while I did this and I didn’t want to have that pole. I wanted to achieve that freedom first. I do think that there can be steps along the way of shifting and that it’s not this one-size-fits-all or even this permanent approach for each individual.
Mike: I think that’s all an interesting thought experiment. If you have any thoughts of your own, just feel free to head over to the website at startupsfortherestofus.com. Leave a couple of your thoughts in your comments. With that, we leave you for today. If you have a question for us, you can call it in to our voicemail number at 1-888-801-9690 or you can email it to us at questions@ startupsfortherestofus.com.
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Episode 402 | Tactics for Minimizing Disruptions to Your Vacation
Show Notes
In this episode of Startups For The Rest Of Us, Rob and Mike talk about some tactics for minimizing disruptions to your vacation. Sometimes, it’s really tough to feel like you can unplug as an entrepreneur, especially if you’re running a SaaS. The guys breakdown some things you should do for your next vacation.
Items mentioned in this episode:
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 Mike.
Rob: And I’m Rob.
Mike: We’re here to share our experiences to help you avoid the same mistakes we’ve made. How are you doing this week, Rob?
Rob: I’m doing okay. I’m a little tired. We landed back from California. Landed in Minneapolis last night around midnight, hopped a lift with the kids, and got home, and in bed around 1:00 AM. I’m on Pacific time so I had a couple of hour times change this morning trying to get up. It’s a little slow getting going but overall, really enjoyed our time in California.
I had talked about previously that we’re going to spend some time with my family in the Bay Area. Our kids had a music camp in San Francisco and then we went and saw Sherry’s folks up in far north California.
Overall, it was good vacation; some vacation, some kind of work stuff. The camp isn’t exactly vacation because it’s pretty intense music practice for the boys. Each day we have to be present and stuff. It wasn’t like we could just kick back and sip martinis or whatever.
Mike: You don’t get to send them for the day?
Rob: No. That would have been ideal. It’s less at camp. It’s actually called an institute, the Suzuki institute. You go and it’s five or six hours a day of them playing instruments, and the parents have to be involved to a certain extent, so you’re sitting in there with them. That’s where I was like, it’s some vacation and it’s some not-vacation. It’s fun in the afternoons and evenings when we took the boys and did stuff but otherwise, got there and back unscathe, which is good when five people are traveling and we lug a cello with us on the airplane. In true chaotic fashion we were back, like I said, landed last night at midnight and then we close on our new house tomorrow in Minneapolis. We show up and sign papers in the morning.
Mike: Stick around for a while then, huh?
Rob: I know, yeah. That was the decision. We really evaluated it after I left the Drip a couple of months ago. It was a decision point like, “Okay, we’ve been in Minneapolis a little less than two years and we can move anywhere. That always sounds great in theory but when you have no real ties anywhere for work—we have family in California—but there’s no reason for us to live in any particular city. I shouldn’t say no reason. There’s no requirement that we live in any particular city; becomes a very difficult thing to tackle. It’s a paradox of choice, it’s almost too much choice.
We evaluated going overseas, and then we evaluated all these cities on them, basically the west coast, even Austin, Denver, Colorado Springs, and Sherry threw Hawaii or Maui. Actually, all these sound great but then you look at what it’s actually like to live there. You look at the days of sun per year, you look at the cost of living, you look what the traffic is like, and you read on Quora. You say, “What’s it like to live in insert city?” You can start to get a feel for what it might actually be like and certain ones just right off the bat are just removed from the list. There are just deal breakers that come up.
I love the Bay Area, I grew up there, and it’s the tech hub of the world, so to speak. But the cost of living there is outrageous. It always has been but it’s catastrophic, basically, and the traffic, I couldn’t deal with them. I would like to live in parts of LA but the traffic there is–you know, it’s just on and on and on there. There’s just things that knock it off.
It was a long and detailed conversation but eventually we got to the point where we decided that staying here was the best option of all of them. But it was a good exercise to go through, to arrive at a decision, and feel good about it, and then be like, “We’re going to buy a house.” We figured that this is a 10-year decision. We have kids that are basically 7, 8, and 10. In 10 years, they’ll pretty much all be gone from the house. At that point we will very likely either keep the house and get a second one somewhere sunny or we’ll sell the house and completely relocate.
Mike: I would have completely lost the pool on any bets that might have been placed about where you’re going to live after your time at Drip is over. There’s no way I would have picked you sticking around in Minneapolis, like there is no chance.
Rob: I think a lot of people wouldn’t have thought that and told us that, and frankly, I probably would have lost the pool as well. I would have imagined we would probably move back somewhere in California but there, at a certain point, quality of life and other things factor in. We lived in a lot of places. We visited a ton and we’ve lived in a lot.
Every once in awhile, you find a place where it’s like, “Wow, this is a world class city with world class amenities, but without so many of the problems of other cities that we’ve lived in,” including location, cost of living, crime, good schools, you just go on a list of all the things, access to airport, delta hub, all the stuff. As we looked at all the other cities, it was just so hard to even think about giving up each of the things that we have here. I wouldn’t have called it from the start, either. I think Sherry might have. She knew it was a pretty cool city here. I had no idea before we moved here.
That is the story. We close tomorrow and then we basically move over the weekend. The nice part is the house, it’s only a block away so it’s an easy move. I can move my own guitars and expensive stuff without worrying about movers trucking a dent truck.
Mike: Yeah, I think that would have been the deciding factor for me, it was that I wouldn’t have had to move my stuff. That’s why I would have just stayed there.
Rob: Totally. No, I know. I’ll admit that we used to play factor but at this point, we’ve done it enough that’s it’s like, “You know what, it’s a temporary pain. If I want to make it a 10-year decision, I’m going to make the right 10-year decision. Even if stuff gets broken or even if I have to pay more money to have someone move it. Let’s make the right decision for long term.” How about you? What’s going on?
Mike: I have some potentially good news here. The contract is finally signed for MicroConf Europe. That took forever. I saw it in an announcement a couple of weeks ago and I talked about it on the podcast. We hadn’t had signed paperwork in place yet and the problem that we ran into is we actually had to switch hotels in the meantime. It really sucked to have to start this process completely over which is why things stall for so long. We do have the signed paperwork, was sent over this morning, everything should be good to go. MicroConf Europe will be in Dubrovnik, Croatia this year and it will be from the 21st to the 23rd. That’s Sunday, Monday, Tuesday of October.
Rob: Looking forward to it. It’s going to be fun. Buy your tickets now. Oh wait, tickets aren’t even on sale yet. When do tickets go on sale?
Mike: Within the next week or two. I’m probably going to be sending an announcement over the next couple of days and then give people a little bit of time just to make sure that they can check their plans or whatever. I don’t want to drop it on people say, “Hey, here’s the date. By the way, here’s the link to buy tickets.” So give people at least a little heads-up.
Rob: Cool, that’s exciting. Glad to have that locked in. Looking forward to seeing folks there in a few months.
Mike: You had asked for an update on the local meetup that I did?
Rob: That’s right.
Mike: I think there were five of us who showed up? There were a dozen people or so that I invited. Some of them just couldn’t make it because either the day of the week or it was just a little bit too far based on the location. I try to picked something that was central to everybody but obviously, it’s going to be farther for some people than others. For some of them, it will end up being a two-hour drive and it wasn’t going to happen.
But like I said, five or six of us got together and it was a good time. Everybody was just chatting about what was going on in their business, how they were doing things, and what sort of markets they were going after. I think two of them were there who had previously purchased my book and then the other two had come in. They were both at MicroConf. It was nice to see a little mix of those guys and both of the guys who bought my book, I think were also in FounderCafe as well.
Rob: Oh, cool. That’s always fun, man. Glad to hear it went well. What’s going on today?
Mike: Today, we’re going to be talking about tactics for minimizing disruptions to your vacation. The idea for this topic came up because there was a thread inside FounderCafe that was posted for somebody who was asking, “How does everybody else take vacation because I’m worried about things like DDoS attacks or servers going down and this and that.” I thought what we do is we spend an episode looking at different ways that you can mitigate the risks to any of the things that could go on that could just end up disrupting your vacation and make it more stressful to go on vacation than to actually be on vacation.
Rob: That makes sense. I think this is obviously a concern of a lot of founders and I think in the early days it’s hard to even know how to approach it. I do hear this question now and again. This is from a FounderCafe thread that someone posted in and there was some pretty end-up discussion about it. I think we’ve talked about this before in like a Q&A episode, probably 100-200 episodes ago and I think this warrants rethinking and refreshing everyone’s mind about how to pull this off every so often.
Mike: To dive right in, we’ve broken this up into several different areas of what your business is. I think the first place to start with is the place where you probably get a lot of headaches that come out of it which is support request from either your existing customers or from prospective customers. Because you don’t want those things to go unanswered for too long and you just want to make sure that you’re responsive to people so that they don’t say, “Hey, what’s going on? Why is this business that I’ve trusted for so long with my data and my application, why are they not responding to me?”
Ideally, what you would do is you outsource and then empower your support people to do things for you. The problem is that not everybody is in the position where they even have support people and that’s, I think, is the most common situation. If you’re one person and you got your business running, it’s a SaaS application or something like that, how do you respond to those support request while you’re on vacation? You don’t want to be on a ferris wheel or something like that or just about to get on a roller-coaster and suddenly, you check your email and there’s these support requests that seem like they’re emergencies, and you got to deal with them.
Ideally, you outsource that stuff, but at the same time, you can also just do some time boxing here. If you block off a little bit of time in the morning and then again in the evening to handle some of those support cases, you can prioritize them. If it’s something that’s pressing or an emergency of some kind—obviously, there’s varying degrees of that—but if it’s something where it’s a feature request or some data that needs to be added, you can stall for time a little bit, say, “Oh, I can get to that tomorrow or the day after, or give me a couple of days. That’s probably the most common phrase that I use if I’m on vacations. “Give me a couple of days and I’ll get to that.” And then if it stretches from a couple of days to four or five, it’s not usually a big deal especially if it’s early on in your vacation.
Rob: The first piece of advice that I give a lot of folks once they get a business to the point where it’s making any kind of money is outsource your support. This is relevant to vacationing but it’s more so relevant to the other 45 weeks of the year. That depends on how much vacation you take. This is one of the biggest stumbling blocks I see is, founders hanging onto frontline support for too long. It’s always the, “Well, it’s only half hour a day or it’s an hour a day and no one can do it because my product’s really technical.”
It’s the same objections every time and every time once that exact person—I’ve seen this over and over and over—finds the right support person, doesn’t mean you just can hire anybody off the street, you may need to hire someone with a little bit of specialization, you may need to hire someone with prior WordPress knowledge, you may need to hire someone who, I don’t know, is an audio engineer on the side, and then knows audio stuff on the side if you have audio plugins. There are ways to troubleshoot this.
Entrepreneurs don’t say can’t as much as other people, and there are always objections and there are always hurdles, but once I see founders outsourcing this, it’s always the same realization at the end of, “Oh my gosh, I’ve should’ve done that six months sooner. I’ve should’ve done that a year ago.” If you get nothing else from this episode, if you’re still doing support, find someone to do it and then that, of course, will carry over into times like this when you go on vacation. It will be so much easier for you to do it.
Mike: The next one isn’t so much as a full-blown section. It’s just a word of advice and caution, which is learn from wisdom of having done this exact same thing. Do not push new code within a week or two of going on vacation. Just do not do it. It almost doesn’t matter what the code is because I’ve seen code that I push live a couple of weeks before going on vacation. This happened this past year with Big Snow Tiny Conf where I pushed it out, everything looked fine, waited a week, everything was still good, went on vacation, and the very first day of vacation something came up. It wasn’t actually that code. It was code that was even further back from that and the situation did not come up where that bug ended up surfacing to the point where something bad happened and I had to deal with it. The longer you wait between the time you go on vacation and the time where you’ve pushed that new code, the more likely you are identifying any problems with it and be able to fix them.
Rob: You mean I shouldn’t push new code and then hop on a 12-hour plane flight with no internet?
Mike: If you have no customers it’s probably not a big deal. You can get away with it with certain apps. If they’re not logging in very often, if it’s something where it sends them a weekly report or it’s batched, that stuff’s not as big a deal. But if it’s something they’re logging into and they rely on it for their business, depending on how critical it is in their business, it can be a really big deal and you don’t want to screw with other people’s business.
Rob: That’s the thing. If you have a team that is able to monitor and fix things, then you can, I’ll say, break this rule or bend this rule. You can push code a couple of days before you head off for vacation.
We had an informal rule at Drip almost from the start where we would not push code after—it got earlier and earlier in the day—but I would say, it was around 2:00 PM, so we’d really try to push stuff right around lunch or right after lunch. We had several hours to really see them in production. That was after it was fully tested, heavily unit tested, and all that stuff. Then we really tried not to push stuff on Friday. If we’re going to push it on Friday, we would push it in the morning like it was a 10:00 AM stop.
It always varies. If it’s s typo fix or it’s one little Javascript thing on one screen that could potentially break some minor feature, we’re obviously more loose with it. But if it was some major thing about rerouting the email sending through this different pipeline or if it was modifications to the scheduling, email scheduler, like really big, big deals that could really impact someone’s business. Those things we took with a lot of caution.
It wasn’t again, it wasn’t just about vacation but it was just about having sanity check on. If you have a team that can fix it, you have a little more leeway. But especially if you’re a single founder operating on your own, you need to be very cognizant of not breaking your app.
Mike: With BlueTick, most of the activity and usage is during the week and on the weekends it really drops down quite a bit. Like any major changes, I’m typically pushing them on a weekend because it’s going to impact a much lower number of people. During the week, it’s a bigger deal. I can push something over the weekend and monitor it.
As long as I’m not seeing anything major go wrong with like the smaller number of emails are being sent, it’s not as big a deal. But otherwise, other major changes will go live 8:00, 10:00 o’clock at night, and then I just watch it a couple of hours to make sure that nothing major is going on and check it first thing in the morning to make sure nothing else happened. But everyone’s app is different, so you have to take that into account.
The next category to look at is sales and presales. If you are doing demos of any kind—typically you have some sort of a way for people to schedule those—the first thing you should do is just block off your calendar so that people can’t book sales demos with you while you’re on vacation. There’s times where that’s absolutely necessary or where you may need to do a demo for somebody.
I actually have on my calendar, there are certain unlisted links that you can use that will essentially ignore everything and it doesn’t matter. I use those specifically for situations where I really want to talk to somebody or it’s a high-profile customer, I think that it’s going to be a good fit or I’ve been working on for a long time—those I want to give a little bit more priority to. I’m more lenient with those especially in terms of the time of day and things like that. But you don’t want to just let anybody sign up for your sales demos if you’re not going to be around because then you’re still subjecting yourself to the mercy of whoever is putting themselves on your calendar.
Another thing is using an out-of-office responder. Now, I think this is a judgment call. I’ve gone on vacations without putting those in there just because I didn’t want to having sending out messages that says, “Hey, I’m on vacation,” but at the same time, you may want to do that so that it does set expectations. It depends on how much email you get and what types of people you’re getting that email from.
The next thing you can do to help minimize some of the disruptions to your vacation is to hire somebody who is technical to be on-call. This could probably be a lot less expensive than you might think because you’re not actually paying them if they’re not working. You may say, “Hey look, I’ll give you a couple of hundred dollars to be on-call and if there’s issues I’ll send them your way.”
If you’re going to do something like this, obviously you want it to be somebody you can trust. Either a friend, a colleague, a mastermind group member. Those are all great people to turn to. Or if you have a DBA who’s been helping you manage your database, those are all people who are probably going to be at least somewhat familiar with you and the technologies you use. But you can provide them with at least minimal documentation and training on how things are architected, and what would need to be done or what things impact other things in the environment that they may need to look at if there is a problem. Obviously, you need to give them credentials to be able to login and get access to stuff.
Another thing you can look at is having any sort of a hosted infrastructure can be really helpful in this. If you’re using AWS, a lot of those things are generally taken cared of for you. But if you have your own virtual machines, maybe hosted on Rackspace or something like that, those types of companies do have their own support people where you can say, “Hey, let me turn this over to them,” and then they may require an on-going support contract but that might also be something you look at for a much longer period of time and on an ongoing basis.
Rob: This one’s tough. I think if there’s network connectivity issues or if there’s server issues, and you’re on AWS—some of them assume most people are probably on some type of PaaS, Platform as a Service, like AWS or Azure—then you can hand that over to them. But so much of this stuff winds up being application code. That’s a thing that’s changing constantly. That’s a thing that is vulnerable.
I think getting someone up to speed just for a two-week vacation is going to be really, really tough, even if you provide docs and all that stuff. You know how it is. It is such a jungle when you haven’t been working on an app for at least a couple of months and have some exposure. I can imagine if you had a junior developer who you’d ramp up a couple of months. He or she could handle 20% or 30% of the stuff that came up and then escalate to you as needed.
But try to get someone up to speed, just drop them into an app and be like, “Alright, if these things go wrong, try to do this and try to troubleshoot that,” I think this is a really tough approach. I haven’t heard of anyone doing this, I guess, successfully that hasn’t already have that developer doing it on an ongoing basis, whether it’s a contractor who’s worked on the code from now and again.
I like your idea of the DBA. The Drip DBA who worked with us for years and is still the DBA there. He’s a contractor but he would have been able to dip into the application code a little bit because he had enough knowledge of the app just digging around in there.
Mike: I think there’s a difference between having somebody who is technical enough, is the sysadmin, at the sysadmin level versus somebody who, like, “Hey, I need you to go look into this bug,” stuff like that. I’m thinking probably be pushed off to the side for the most part, especially if you’ve done the due diligence to say, “Okay, we’re not going to push any new application code for a week or two.”
Those things should have ironed themselves out for the most part, but then when you get into things like network connectivity issues or the database isn’t responding, things like that, most technical people, I think, should be able to handle that stuff. If you have somebody who’s a DBA or a systems engineer, they can look at that stuff and start troubleshooting them. They’re not so much looking at the application itself. They’re looking at how do all these moving parts touch each other and why are they not working well together. It’s being able to at least identify that type of stuff.
That leads us into the next section which is using third-party monitoring services. Most of us, I think, have our own logging mechanisms of some kind that are either built into the application or are taking those logs and putting them off onto a third-party service. But there’s lots of other third-party monitoring tools that you can use like Pingdom and uptime.com. Rob, you had a […] in here I’d never used or heard of that one, but—
Rob: That’s Laura Roeders’ new startup.
Mike: Ah, okay. Cool. There’s also PagerDuty and Uptime Robot. There’s another service that I use called Datadog, which allows you to essentially constantly monitor what’s going on your servers and get detailed information about performance metrics of the system’s various aspects of it, whether it’s the database, or the application, or just different processes that are running. I use just that because there’s lots of different things that need to be monitored but conjunction of all these things is that, you can use those to figure out what needs to be escalated. If there’s certain things that cross a certain threshold for you to actually pay attention to it, then those are the things that you would need to escalate to either the technical person that you have, or a support person, or even maybe ends up going to you at some point.
Rob: Our next tactic is to turn off your phone and email during the day. Basically, automate any major escalations to SMS and ignore everything else so, ignore your email. Essentially ignore your support queues based on what we’re saying above is to try to get to the point where you can vacation, enjoy, and be present with yourself, or with your family, or whoever you’re on vacation with, and not feel the need to be checking inboxes all day, and not feel like something’s going to slip through and you’re going to miss it, or not to get a ping, a notification on your phone every time an email arrives.
Because of that, it’s catastrophic for enjoying your vacation. I think it’s a big thing. I’m someone who does not get notifications when emails arrive anyways. I think that’s a pretty bad idea for your productivity but if you do that when you’re not vacationing, then you need to turn that off when you are.
Mike: I turn pretty much all notifications on my phone off. The only one that would end up coming up and surfacing for the most part is certain things coming from the server logs, they pop-up on my phone, and then text messages. That’s basically it. Obviously, phone calls will come through but other than that, nothing is pushed to me in an interruptive way.
The last thing to take a look at is do some technical preparation, create a checklist, and use that checklist to look for potential upcoming issues. On this check list you would want to put things like, “Are my SSL certificates going to expire anytime soon? Does the system have enough space? Does it look like it might run out sometime in the near future? What is the CPU usage look like? Do I need to do any sort of upgrades, or give it additional disk space, or plan for more resource capacity in the meantime that would help me get through that and help mitigate any potential problems that would result from, maybe you get an influx of traffic, you get a bunch of sign-ups and your server gets bogged down?” If you upgrade the infrastructure a little bit, then that would help take care of it.
The other thing you have to look at is things that are completely beyond your control. For example, a DDoS attack. What happens if your application or your website suffers a DDoS attack? There’s other things out there, there’s services like Cloudflare that can help you out with that. You can also build redundancy into the application or into the website itself. But again, these are types of things that could come up but they’re also typically lower risk, unless you have a large enough footprint. Early on, these aren’t the things that you probably going to have to worry about too much but even in the case of a DDoS attack, your customers are probably going to be pretty understanding. It’s not like you did something wrong.
Rob: Yeah and these are things that you want to do anyways. This is stuff that helps if you have it during your vacation but any of these things can happen at any time. I’ve had SSL certs expire on me. I think it’s only been once and it was when I acquired an app, and of course, the contact email for the SSL cert expiring went to the old owner, like their personal email, so I didn’t get any emails. Suddenly, boom on a Sunday afternoon—it was HitTail—the Sunday afternoon, the site isn’t SSL anymore, isn’t secure, and Google Chrome has a conniption when that happen.
I remember calling GoDaddy on the phone, Sunday afternoon at 3:00, I’m thinking, “There’s just no chance. This is going to be a 24 hours or something and man, […] help me right away.” I’m assuming this happens to a lot of people because I think it was within 30 minutes they issued a new cert and I was able to get it.
That would be terrible to happen on your vacation. Like you said, you’re out on, what was the example that you used earlier?
Mike: Like on a roller coaster or like on a Ferris wheel.
Rob: Yeah, or I’m thinking we were snorkeling a few weeks ago in Florida, or you’re out on some safari, or you’re doing something where either you have almost no cell service or you just don’t have the headspace or connectivity to handle this well. It’ll be a stressor and kind of ruin that part of your vacation.
These are the kinds of things to have that check list that you’re probably thinking about on an ongoing basis but really revisit before you head off the grid.
Mike: One thing I found a little bit helpful for things like expiring SSL certificates or even domain name renewals is I actually add them into my calendar and create it as a recurring task that needs to be addressed at some point. That way, I actually use Teamwork for that piece of it but all of them are in there, so that I know that even if I don’t get a notification from whoever that is, I still see it as a task that needs to be taken cared of. If I renew for two years, it’s not a big deal. I can just mark them off. But at least that way, I have my own internal notification that serves as something of a backup.
Rob: That’s a nice way to do it.
Mike: Helps you avoid lost domain names, too, because I’ve had that happen which is why I have that system in place now.
Rob: Totally. Email is mostly reliable and that non-mostly part, the part that is outside of them, the most mostly circle can be pretty bad for domain names, SSL certs, and all that. I think that about wraps it up for today.
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Episode 401 | Why You Shouldn’t Listen to Your Customers (And What You Should Do Instead)
Show Notes
In this episode of Startups For The Rest Of Us, Rob and Mike talk about why you shouldn’t listen to your customers. Not all requests are created equal. The guys breakdown customer feature requests into three categories and give tips on how to get the most out of them.
Items mentioned in this episode:
Welcome to Startups For the Rest of Us. The podcast that helps developers, designers, and entrepreneurs be awesome in building, launching, and growing software products whether you built your product or just thinking about it. I’m Rob.
Mike: And I’m Mike.
Rob: We’re here to share our experiences to help people with the same mistakes we made. To where this week sir?
Mike: Well, I submitted the Bluetick Zapier integration to Zapier, to see about promoting it through their public availability process. I’ve already heard back from them. I’ve got a list of things they want to see changed to conform to the standards that they kind of set for everybody to maintain consistency between Zap. I got to go back, and look at those, and make some changes and then publish it but things did not seem to be too terrible.
Rob: Nice, that’s super cool man. Once that goes live, it’s nice to be able to refer customers to Zapier when they’re trying to be something in your app that you haven’t built yet—when you don’t have an integration. That was always the useful piece for us.
Mike: Yeah. Well, the thing is like the Zapier integration is already there, it’s just invite only and there’s a link inside the app where they can click on that link and go over there. The difference is it will be public so that when people are searching inside Zapier to see where there is a Bluetick Zap, they’ll be able to see it but I’ll have them to login in Bluetick first. At that point, they can add it into their account but I guess you can’t ready do anything without an API key anyways.
Rob: I remembered when Zapier promoted HitTail early on we got a bump and then Drip, I remember it was—I think it was more or less, but it definitely in the early days when you’re really scraping and clawing for every customer. I think that you get included in the email newsletter, tweeted out, I think, and every bit helps at that point. Even if you only get a couple new customers from someone hearing about it, it can move the needle for you in the early days.
Mike: Yes. I’m hoping to see that at least through the initial process in the next couple of weeks or so. I don’t know how long it has to be in their beta for before it ends up being live. I think that they said that—when I was looking through the specs—they said, “You should have at least one person using each Zap and you need to have at least 20 active Zaps,” or something like that. They’ve revised their stats page to see if you can actually see more about who’s using it, how many people are using the different Zaps that you’ve published or made available. I’m up to like 400 active or something like that, and only need 20.
Rob: Oh, yeah. That’s a lot more than we went live with it. That’s cool. segment.com will be another one. You’ll probably want to do it at some point—integrate with them. That’s another big hub to get not only the promotion but it’s just nice because people are going to want to create reports or do things with the data that you’re just not going to have the time to build and referring about to Segment, it can help there.
Mike: Yeah. Ultimately, I’ll look into that one as well. The other thing I’m in the middle of right now is kind of specking out with the public APIs going to look like. Everything in there is all used internally inside the app and then I have a specific endpoint that’s used solely for Zapier and then next step is to really kind of take that and say, “Okay, when are we going to make it public?” because there’s a couple of customers who have wanted to use a public API but I told them to kind of hold off and just use Zapier. I had a call this morning with somebody about what the specifics things they needed from a public API from us are. There’s at least one other customer that I want to talk to who I know they do a lot of extensive development work and are using Bluetick as the backend CRM for their entire company. They got several mailboxes attached and they want to be able to use that functionality inside there. I definitely want to have a conversation with them first before I start making anything publicly available.
Rob: That makes sense. For me, I am in California when this episode airs. We’re heading there for about two weeks. We’re going to see different groups of family in different areas and my sons are going to a cello and violin camp—Suzuki String Camp in San Francisco. It should be fun. It’s where I’m from. It’s nice to get back there once or twice a year to kind of see the family and all that.
Mike: Cool. Hopefully you won’t be selling the company while you’re out there.
Rob: I know. That’s the old story right? That I was signing the final docs at the cello camp a couple years ago.
Mike: Getting dirty looks.
Rob: Indeed. Dirty looks from the instructor.
I titled this episode Why You Shouldn’t Listen to Your Customers and What You Should Do Instead. Realistically, it’s about deciding which feature request to build and which not to—not even feature request, just deciding what to build in general. There’s always the popular meme of like launch soon and then your customers will tell you what to build.
I’ve seen struggles with that. Number one, often times your customers don’t know really what they’re trying to do or they’ll tell you to build things that you shouldn’t build but you should do it a different way. Or they’re just going to tell you to build your competitor. They’re going to say, “Hey, I’ve used Infusionsoft and it has these features and you don’t have them. Can you just build this, this, that, and this?” We have these all the time in the early days.
Remember, early Drip user wanted a mobile app. He wanted kind of like an iOS and an android app. He wanted these very specific reports that made sense in Mailchimp but wouldn’t have made sense for Drip to have. He’s not a software person, his idea was just to have this be Mailchimp but with a cleaner interface and that wasn’t what we wanted to build.
It’s really easy when you’re getting multiple feature request per day. I left Drip a couple of months ago, I think we get 150-200 feature requests per month. It’s a substantial line and at a certain point you have to figure out how you’re going to evaluate what to build and what not to build.
I see these like there’s three types of feature request. The first type is—I humorously named this, the crackpots—but it’s kind of odd ball request that you know that there’s no chance you’re going to build, that kind of come out of left field. Some examples of those are, people requiring you or asking you for feature that would require you to build an entirely new product. For example, “Why can’t I use your email service provider to publish blog posts on my WordPress site, or to record my podcast and publish them, or to do all of my social media marketing?” Some people would ask us to, “You do email, I want you to do Facebook, Instagram, Twitter, and do these integrations.” It’s not that we would never build those but people were asking these when we didn’t even have very basic features. In the first year or two, there were folks who were asking for these. It’s just like, “Yeah, I know. There’s no chance we’re going to build that.”
The other one is like asking you to clone your competitors. Like, “It’d be great if you could add a shopping cart, and CRM, and lead scoring.” Basically be Infusionsoft. I was like, “Nope, that’s not our goal.” Or finally, features that are the opposite of your product strengths. I remember someone saying like, “I like that your UI is so streamlined but can you add all these options to fit my rare and unique used case?” They didn’t used those phrases but that’s the kind of stuff that could come across.
Crackpot may not be the best name for them but they’re really the ones that are obvious to you that you shouldn’t build them.
Mike: I think the really nice thing about the crackpot request is that they’re usually very easy to decide what to do about it. You can just say, “No, we don’t do that.” Or, “Here’s something you can sign up for over here and they do that but we don’t.” It’s just very easy to identify them and say—you have to be polite about it—but just say, “No, that’s not something we’re going to do.” Or, “It’s on our roadmap to look at but it’s going to be probably at least six months to a year. It’s not a good fit for you especially if you need it that right now.” That’s the one nice thing or the saving grace about these types of requests because they’re easy to dismiss.
Rob: Yeah, that makes sense. The three types are the crackpot, the no-brainers—which you should build—and the in-betweens. Unfortunately, the crackpot ones are maybe, I’m guessing like 10% of feature request. It’s really a small amount but you’re right, having that certainty is a good thing.
Then, the no-brainers which are the ones where it’s almost like, “Why didn’t I think of that?” If it’s not already on your feature list but you realized, “Man, that’s a really good idea!” I remember Josh Earl, he runs Sublime Text Tips. He also works with John Sonmez at Simple Programmer. He reached out to us in some of the early days of Drip and asked if there’s a way to go back and retroactively add a tag to readers based on things they clicked on the past. It was like, “That was a really good idea.” It wasn’t a huge amount of work at that time. To me, that was like a no-brainer one that both me and Derrick it was like, “Why wouldn’t just we build it?” and we did. I think we are the only tool that does it as far as I know. If you don’t have the kind of the trigger logic and our competitors at the time they click, you cannot go around retroactively tag people. I’ve used this feature all the time. It’s one of those things where if I were to have stop using Drip, I would sorely miss because I will frequently want to go back and do it.
The crackpots are good because they’re definite nos. The no-brainers are good because they’re definite yeses. It makes it a lot easier but I would guess that in total, probably less than a third of your feature request will fit into one category or the other.
Mike: Yeah, for Bluetick, I can’t recall something off the top my head where it has been just a completely crackpot feature request. Most of them have been pretty close to what should be built or what is in kind of on the roadmap but I don’t remember the last time I had something came up that was just out of my field and we’re never going to build.
Rob: Yeah, that makes sense. Then, the third type is the in-betweens. They’re the ones that you actually have to make judgments calls. That’s really what, I think, the bulk of today’s episode is about. It’s about deciding which features to build when customers request them. There’s this whole other path like you’re going to build features that no one requested. If you’re not, then you’re really not innovating. You’re not pushing your product past other competitors. I’m not saying you have to do this but I believe—Derrick and I always had a pretty strong vision for Drip and we were definitely building things that no one was requesting. But, if people are requesting features, I have three questions that we used to ask ourselves. I think that, as a listener to the show, it’ll be helpful.
The first question is ask yourself, what is the used case for this feature request? In layman’s terms, what problem are you trying to solve? I always try to take a step back and people would say, “Hey, can you add a checkbox on this page to modify the setting?” And I would sit, think, and say, “Why do you want to do that?” and almost, in probably 80% of the cases, they didn’t actually want a checkbox there. There was some other party app that wasn’t doing what they wanted and they could go on and use a liquid tab for it. Or, we could add a report that would actually help everyone and that would require them to not need that checkbox.
Often times, there was an alternative way to accomplish this already in Drip or the optimal way to achieve it for everyone to get value—like all the customers to get value—was different than what the person has suggested. Because remember, for the most part your customers are not software people. They don’t know UX, they don’t know apps, they don’t know how to think about what to build to keep a product simple. If you just listen to your customers, you can build a monstrosity.
Mike: One thing that I find very helpful is when you get a support request or a feature request like that, ask them what it is they’re trying to do. That way you’re not guessing what it is that they’re trying to do. Your example, the checkbox, you’re trying to read between the lines to see what it is that they want or what they’re trying to achieve. Sometimes, it’s just not even related to anything that you have or it’s very situational specific inside their business. I find it blatantly asking, what is it that you’re trying to achieve or what problem are you trying to solve—that is really helpful.
Rob: The second question that I used to bring up all the time when someone requested and we start evaluating is like, will more than 5% of our user-base use this feature? More than 10%? More than 20%? As a founder, you have a pretty good feel for your customer-base especially in the early days. It’s just asking yourself, will a lot of people get a value out of it?
The number is our return, maybe your market as well. If at least 15% of people use it then it’s good. Or maybe it’s such a marketable feature that even if only 5% of your users use it but it’s an aspirational or a checkbox feature something like split testing in email marketing apps. We found out that a lot of people requested it and when we built it into campaigns, almost no one uses it. It’s like 1% adoption. But, being able to say that we can split test in campaigns and have it on the marketing side and talk about it during sales calls, it is something that’s just important. Honestly, the Visual Email Builder—I think it’s in beta in Drip now, went live after I left—I bet a lot of people won’t use it. But it is a checkbox item that when, especially larger customers, want to sign up and they’re going to sign a one year contract, they want to make sure you have this, this, that, and this because your competitors have it. At that point, sometimes you have to make a choice of like, “Well, only a fifth of the customers are going to use this thing but it’s going to get us a lot more business.”
Mike: I think a lot of times you’ll see people going if they’re evaluating different products, they’ll compare them to each other and try to say, “Okay, what features does this have and which features does that have?” And something they may not even necessarily use, the fact that it exist and they could use it if they wanted to, is a good selling point. But I have mixed feelings on that just because sometimes people will use it just to make a decision versus wanting to use it.
This is kind of where my hatred of this process comes in but I will see people deciding to implement those features. The vendors will implement that feature and the feature itself just completely sucks but the only reason they built it was so that they can create like that checkbox on their website to say, “Hey, we have this feature.”
Rob: That used to kill me, actually. We had a few competitors build really crappy versions of split testing that were actually harmful. They were not statistically significant. I was face palming because it’s like what they say, they can say they a have split testing but it was a [shit 00:14:27] implementation of it. It’s actually going to be a detrimental to their customers. I could never bring myself to do that in a product like to build something crappy. As a result, stuff for us probably took longer to build than some competitors.
There’s one other trick we used a few times as well and it was in the early days only. It was a larger customer who’s revenue would move the needle. We did build a couple of features that we basically hid in the UI except for a handful of people. Literally, like less than 1% of Drip customers would be able to see this feature and it was a feature that really we didn’t want to build. We didn’t believed it should be in a product but the revenue at that time was just something we couldn’t pass up. We didn’t do it a lot but one of the bigger reasons we didn’t want the feature in it is because it would add more checkboxes and dropdowns—just negatively impact the UX, in essence. Most people weren’t going to use it anyways and so that was a choice to just kind of—we had a feature flag and we don’t want to go into a few accounts. There’s still are a few features in Drip to this day that really only appear for a small subset of customers.
Mike: I think I have access to a couple of these features.
Rob: I bet you do.
Mike: That’s interesting. I did the same thing with Bluetick where there are certain features that you can’t even use inside the app but I have like a backend toolbox application. It allows me to either toggle them on or off or do different things inside of somebody’s account where it achieves what they want but is not something that they could actually do inside the app.
Sometimes, I’ll use that to either test it out in kind of production. For example, one of them was a Bcc field where people like, “When I send emails out, I want to Bcc this other email address.” For a long time that was, you could do it inside the app but there is no way in the UI for the user to see, that it was actually happening. They had to contact me through support and I would actually put it into a field in the database that would make it work. Now, it’s actually ruled out and everybody can use it. I use this kind of mechanism for sort of testing it out with live data to some extent.
Rob: Yeah, that’s really good way to do it. We did that. With any feature roll out that we thought was a risk at all, we would totally feature it temporarily and then slowly enable it for more and more people. Then, in this case, where I’m talking about actually building a feature and never rolling it out to everyone, that was something again, we did that in the early days when we needed to when we’re being scrappy.
I meant to say this at the beginning of the episode but this is actually, this outline is from an unpublished blog post of mine. If I ever get around to finishing that blog post, you may see this on my blog as well. I have additional examples. I can obviously go into more, more things in a 2000-word blog post than we can cover in 25 minutes here. I’ve also considered doing a talk about this. Derrick Reimer, my Drip co-founder did an attendee talk a couple of years ago in Drip on this topic. We have similar takes because we worked together on it. But I feel like we can definitely, potentially be a full 30 or 40-minute talk.
With that in mind, the third question that we used to ask ourselves a lot when we get feature request is, “Does this fit with my vision of what the product should be?” Going back to an earlier example, since Drip was a competitor especially in the early days, it was compared a lot to Infusionsoft. We would get a lot of request to add shopping cart and landing pages and affiliate management—really, things that we didn’t want to build on the product because we didn’t view Drip as, we want to integrate with best in class solutions rather than try to be everything to everyone. We felt like the bloated software just wasn’t, we couldn’t see an example of it in a space where adding all these features has helped anyone. It always makes it a crappy experience.
The fact is when you’re bootstrapping, there’s an opportunity cost. Every hour you spend building features, that’s an hour that you don’t spend becoming the best at what you’re doing. That was where we decided to focus on integration. What’s nice is the integrations were platforms that people were already using like Unbounce, and Shopify, and Stripe, and Gumroad, Leadpages, and PayPal and on and on. We had 35 integrations within probably the first year of being live. It was a nice lift for us in terms of actually getting new customers because all those integrations are—they’re promotional avenues if you can get folks to promote you. But they just make the product more sticky.
This whole ties in the question coming back to it is, “Does this fit my vision of what the product should be?” We always had a pretty strong vision. We want to be a best in class email marketing or marketing automation tool. Therefore, a lot of the request that came through is like, “Huh, yeah, that doesn’t fit with where we want to take the product. We’re just going to have to say no.”
Mike: The part about this, knowing what vision you have for the product is one of those things where it’s a little bit more abstract. You kind of have to step back from the product itself, away from the features and away from the dirty details of how things are implemented and say, “What is the type of person that you want to use this? What is it that you want to empower them to be able to achieve?” Because otherwise, you may have this vision for your product but people come in with feature request and I say, “Oh, this is why I want to do x.”
If it’s one of those in-between things, it could change or alter that vision a little bit and shift it in one direction or another. Sometimes those shifts in direction will isolate or exclude certain types of people as well. It’s something to be a little careful of because your vision can change over time based on the feedback and the feature request you’re getting in. You can easily end up going down the road where you’re tracking the wrong types of people—you’re tracking more of them—but it’s the wrong type of people. They’re having a bad experience because they’re not using your tool correctly or in the way you envisioned and you’re not catering to them anyways. It’s a very slippery slope you can end up on if you’re not very careful about how you’re making those decisions.
Rob: Yeah, that’s a good point. Your vision will likely change over time. In the early days of Drip, my vision was completely different than what Drip became. That was okay but you can hear it was a painful process to make that decision and kind of switch the vision. You can hear it and if you go to startupstoriespodcast.com, there is a 90-minute audio Derrick and I recorder over, I think about nine months. I edited 10 hours of audio down to 90 minutes and you can hear the agonies we’re going through of like, “What should we be building? What actually are we building?” early on. It was one thing then it became essentially an ESP with automation. Decision process is what makes startups hard. We were just trying to find product market fit and therefore our vision had to follow something that was valuable to people.
In the early days, it wasn’t valuable enough. People were willing to pay us but they were not willing to pay us the $49 a month that I want to beat the minimum price point. We had to follow that. Then, once you get past that though, once you start scaling up and growing and you have product market fit, I think it becomes so, so much easier to know what you have, what you’re building, what you should build. It really does get easier. It’s that first year or 18 months that’s really hard to figure out when you don’t have a large customer base and you don’t just have that gut feeling of what you should build based on all your experience.
Mike: Yeah, I totally agree with that. If you’re in a position where you don’t have, I’ll say, a critical mass of users yet, then take a lot of this advice with a grain of salt. Definitely take the feature request with the grain of salt because the decisions that you make now are going to change things in the future and draw or repel certain types of users. That will influence, ultimately, how the product is received in the market and what other features you end up developing.
Rob: I think the thing to remember is you’re always going to get way, way more feature request than you can possibly build. Even when you have 10 users, people are going to be requesting things. As a bootstrapper, time is your most valuable resource. You’re just never going to be able to build anything you want. If you could build everything you want, I don’t know. I questioned if the product would get bloated too fast. It might actually be a benefit that you are time-constrained because I think in the early days, you’re going to want to build anything everyone requests. If you’re able to do that, I think you can potentially build a really crappy, bloated, product.
Mike: Yeah. Definitely the danger in building this many feature is you like is the fact that it makes the interface much more difficult to work with. You have to do a lot more design work with where different things are in the app. A lot of times, as you add features, you have to restructure or re-architect either the different parts of the application itself or the UX which forces underlying changes as well. You’re basically bolting things on after the fact. I think that’s why a lot of people, specially newer developers, tend to say, “Oh, I’d like to rewrite this app from scratch because now we know what we want to build based on the features that we have.” But it’s really tough to do that unless you’re in a situation where you can completely rebuild the app.
I think that David, DHH from Basecamp has talked about this a couple of times where they’ve rebuilt Basecamp from the ground up. As much as I disagree with that decision, I would disagree with it for me and in our situation that kind of makes sense because they can essentially abandon the previous version and say, “Everyone who’s using this, you’re still going to get to use it but anyone new is going to sign up and they’re going to use this newer version and they get to work on new stuff.” But not everyone is in the position where you can basically halt all development on your current app and still be making millions of dollars a year from your current customer bases.
Rob: Yeah. That’s rewriting app—that would be a whole nother episode. I think Basecamp is such an anomaly and such an edge case that very, very few companies will achieve using them as an example is tough just for that reason, because they got in so early and grew so fast. But you’re right. Rewriting an app. I’ve seen several startups do that and I always cringe pretty hard when they talk about doing that because it’s not going to solve all your problems the way you think it will. It’s going to keep you just frozen for six months while you try to rebuild everything.
Mike: Yeah. I think the fallacy there is that you understand how the different pieces fit together so you can reengineer all the stuff to solve your current problems but even after you’ve done that, let’s say, that you can do that in a hour and everything’s completely restructured. Yes, it only cost you an hour but you’re still going to end up getting more feature request that you’re still going to have to bolt on to the application afterwards. At that point, you’re retroactively architecting new features into the architecture and how the UI and UX is all laid out. It just will not solve every single problem that you have. There’s certain problems you’re just going to have to live with.
I think that about wraps it up for today. If you have a question for us, you can call in into our voice mail number at 1-888-801-9690 or you can email it to us at questions@startupsfortherestofus.com.
Our theme music is an excerpt from We’re Outta Control, it’s by MoOt used under Creative Commons. Subscribe to us in iTunes by searching for Startups For the Rest of Us and startupsfortherestofus.com for the full transcript in each episode. Thanks for listening. We’ll see you next time.
Episode 400 | The Importance of Consistency
Show Notes
In this episode of Startups For The Rest Of Us, Rob and Mike talk about the importance of consistency. They reminisce about how the podcast has evolved over the years and the benefits of putting an episode out week after week.
Items mentioned in this episode:
- FounderCafe
- BoardGame Tables
- MicroConf
- Inc.com Article
- Uexpress.com Article
- differenceconsulting.com Article
Welcome to Startups for the Rest of Us, the podcast that helps developers, designers and entrepreneurs be awesome at building, launching, and in growing software products, whether you’ve built your first product; you’re just thinking about it.
Rob: I’m Rob.
Mike: And I’m Mike.
Rob: And we’re here to share our experience to help you avoid the same mistakes we made. 400 Episodes, Sir. Congratulations.
Mike: Thank you. I did it all by myself.
Rob: I know you did. How does it feel?
Mike: I don’t know. I feel very run down today but I don’t think that it has anything to do with Episode 400. I think it has to do with the fact that yesterday was the Fourth of July here so we had a bunch of people over and my kids are away for the week. They’re at Sleepaway Camp. We had a bunch of people over and we’re just like grilling and swimming in the pool, which was 92 degrees or something like that, and we haven’t even kept it covered for several days; it’s just hot as heck.
Rob: Yeah, and you stood out, man. You were hanging out. You drank too much so then you’re hung over and tired today.
Mike: I’m just tired. I’m not hung over. That’s the funny part. I don’t know if it’s funny, but I’m not hung over; I’m just tired. I didn’t sleep very well, I don’t think.
Rob: Yeah, and I feel a little bit the same way you do. We had friends over as well. I’m also kind of tired from the heat and just from whatever else. I think the 400 Episode thing makes me feel, if anything, old. It’s like we’ve been doing this for eight years, I believe. Is that right? Wasn’t it 2010?
Mike: Yes, 2010.
Rob: It was somewhere between February and April of 2010. I could look at the archived pages post, but it’s a long time to do this. We’ve had millions and millions of downloads. I was just looking at the statistics, millions of downloads, tens of thousands of listeners per episode. We’ve built something. We’ve built something pretty special, I think, that resonates with people. We’ll talk more about our favorite episodes and we’d have some listeners who wrote in, and I thought that was really nice. I think it’s a testament that we basically were able to show MicroConf out of the podcast. I don’t know that we could have grown it to what it is without this show. It’s like the entire conference. These days, MicroConf is its own name but, back in the day, we really sold tickets. It was kind of like my email list, your email list and people listening to Startups for the Rest of Us.
Mike: Yeah, and I think that just having that podcast episode that dropped every single Tuesday almost without fail makes people feel that they’re part of something. Then, when you come to MicroConf, you’re meeting the same types of people who were listening to the podcast. As you said, things have grown and people who come to MicroConf don’t necessarily always listen to the podcast. It’s taken a life of its own but, in the early days like that, that was really what drove that audience, I’ll say.
Rob: Yeah, for sure. How about you? What else is going on this week?
Mike: I have a meet-up that I put together this evening. I’m meeting a bunch of people who are either FounderCafe members or attended MicroConf or both this evening over in Worcester. That should be fun. We’re going to head over to British Beer Works or something like that and meet up around six o’clock and just have a couple of drinks, have dinner and just talk business.
Rob: That’s super cool. Did you just initiate that out of nowhere?
Mike: It wasn’t completely out of nowhere. When we set up the slack group for MicroConf, there were a bunch of people in there who were like, “Hey, who’s in the Greater Boston area?” and a few different people chimed in. I think that there was even a private channel that was created for people who are in the Greater Boston area, and then a couple of people mentioned to get in together. What I did was I just went through and looked to see who had come to MicroConf who was in the Boston area and I just emailed them. I have a running list of people that I know who live in the area and I just went through them, emailed them all and said, “Hey, here’s the time, date and place. Who wants to get together?” About half a dozen people or so chimed in and said, “Yeah, absolutely. Let’s go.”
Rob: That’s super cool. That’ll be a nice-sized group, too. I like that size.
Mike: Yeah. We’ll see how it goes.
Rob: Cool. Once you’ve done it, I’m interested to hear how it was on the show.
Mike: Yeah. That’s something we’ve actually talked a little bit about in the past in the background between you and me, just figuring out if that’s something that we wanted to facilitate in different places. I don’t know if there’s a good technical way to manage that, to be honest.
Rob: Yeah, the TropiColombia guys due their juntos, but they do have local meet-ups. It’s definitely possible but it’s always been the question of, “Do we have the bandwidth?” or, “If we don’t do it and we hire someone to do it, how do we make it pay for itself?” basically, right?
Mike: Right.
Rob: We’ve talked about not wanting to run an events business, like we don’t want to be in the events business and yet we throw three events a year already with the three MicroConfs. I think if we did the juntos or something like that, local meet-ups, basically, it would definitely span out itself. I think if we had the aspiration, we could totally pull it off. It’s just not you nor I have ever really wanted to gear up and not work on our software products in order to do that.
Mike: Yeah, I think that’s the biggest issue, is just having the bandwidth to be able to do it and, as you said, without charging for it and hiring somebody to help manage and facilitate all that. It’d be really hard for us to pull it off.
Rob: Yeah. Last weekend, I went to a three-day mastermind retreat, is what I’ call it, and it was the Rhodium Community. You know Rhodium Weekend? Have you heard of it? Chris Yates runs Rhodium, and I have a lot of respect much like I often tell people that MicroConf is the younger sibling of BoS. It’s less expensive, it’s more focused in slightly earlier-stage companies, very few have funding and BoS is a different story. It’s still very much about building real software companies and not with venture-back stuff even though some of them do take venture funding, but I have a lot of respect for BoS.
I also have a lot of respect for Rhodium Weekend. It’s a 100-person event held in Vegas every year. It’s run by Chris Yates, and it is more about buying and selling websites. There’s a lot of talk about internet marketing, but what I found is, like MicroConf, it’s very ethical. Since Chris has built the audience, he’s been very picky about who he lets in and so it’s not the sleazy internet marketing. You can go to a lot of really shitty internet marketing conferences. People are pitching from the stage and that’s not what Rhodium is.
Every year, there’s a Rhodium conference and then he has this mastermind that he runs that Sherrie [ph], my wife is a part of, and it’s a monthly call with about 14 people, and they do hot-seat format. They do all kinds of stuff. Once a year, that small group of 14, goes to a house and stays there for three days and they do a hot-seat format. Sherrie [ph] was unable to make it and there was a seed open so they invited me because I know Chris and I actually knew a few people in the group as well.
For me, I had to really think about whether or not I wanted to do it because of that format. I know you’ve done this with Big Snow Tiny Conf. I’ve never done that. I’ve done really small things with four or five people and then I obviously do MicroConf, but that in-between felt very uncomfortable for me going into it, especially knowing only three people there in advance. I really debated whether to go or not and, in retrospect, it was awesome, like it was really, really good as I kind of knew in the back of mind it would be.
I felt a little introverted and everybody else knows each other really well because they’re on these calls and they hang out, but it was a big deal. It was game-changing for me in terms of my thought process of, “I think I want to do that again.” It makes me really want to do one of the Big Snow Tiny Confsnow that I have more scheduling flexibility. I don’t ski but I’ll drink hot chocolate and read comic books or something while you guys ski or snowboard. I think I want to do it.
The cool thing about it is it really opened my eyes to the value that you can get from a group of that size, and that was my doubt. There were certainly some struggles with it, too. With 15 people, I think in my opinion, it’s just a little bit too big. I would love for it to be 8 to 10, and that would be a perfect size. With all of that said, I can imagine that it might be even more valuable to have everyone having the same type of business or at least similar because they were all over the board.
There were people who literally just build and buy content websites that they monetize with affiliate links and AdSense. There were e-commerce. There were e-commerce drop shippers. There were people who manufactured their own products. There were two or three SaaS. There were some people who just do a lot of SEO and they just build sites and sell them. There’s a real wide variation of who’s done what, and I think that was super helpful but I also imagined, if everyone was SaaS, that there could potentially be more value to it.
Mike: Yeah, and it goes both ways, though, because if you have people who are doing things in different types of businesses, then you get a different perspective than you would if everybody is doing the same type of thing. If everyone was doing SaaS, you don’t get the perspective of, “We’re e-commerce and this is how we do affiliates.” They may view them very differently and you can get really good, solid takeaways from those that you can put together and put forth on your business that are going to work for you. You would not get that if everyone is always talking to the same types of people, I’ll say.
Rob: Yeah, I totally agree. It’s a good point and that absolutely was true. I was surprised how much I had to offer someone doing drop shipping commerce. It was more than I thought. Some hot-seats would start like, “Boy, I’m not sure I have anything to add here,” and then I would have insights. It’s like, “Yeah, that was similar to my experience with Drip.” There’s enough overlap with these businesses–maybe at 60% similarity–because there’s always going to be marketing, and there’s SEO, and there’s affiliate programs or whatever that’s similar. I don’t know. Maybe having everyone working on the same type of thing would take away from that, the variety of thought or whatever.
Mike: Yeah, I definitely think that that’s probably the case. It depends on, specifically, what you’re looking for. You could easily have a group that is all the same types of people than a different group that is very different, and it depends what you’re trying to get out of the group. I think that that’s more the issue than anything else because at Big Snow Tiny Conf, Chad DeShon runs boardgametables.com and he’s got some fantastic ideas but because he’s B2C and he’s selling physical products, he’s not the type of person that I would probably end up in a group with but he’s got fantastic ideas. I’ve seen some of the stuff he’s done and it’s just amazing, and then there’s other ones who are doing more e-commerce-type businesses and we get some great ideas from them people, too.
Rob: Yeah, that makes sense.
Mike: I don’t know. It depends on what you’re looking for.
Rob: For me, where I’m at right now where I don’t really want to start another SaaS app, it was super helpful because I was able to talk to people about what it’s like running an e-commerce shop, not that I’m going to necessarily run one but I at least was able to talk for an hour to someone who’s been running e-commerce, manufacturing their own stuff for 10 years. It’s like, “Wow, those are the headaches of it. I don’t think I want to do that.”
Then, another guy who’s built two authority content sites from scratch, not just these little content sites that have AdSense or whatever but really built something substantial that he sold for I’m presuming six-figure exits–and I don’t know how much they were–but he had a whole process and a whole realm of knowledge that I have just not been exposed to. That was helpful for me to be like, “Yeah, maybe an authority content site is the next thing for me.” It just got me thinking along different lines, which is helpful because I am, at this point, direction-less in the sense of what I am going to do next.
Mike: Yeah, that makes sense. I’m curious to know what was it that you went into, thinking that you were going to get out of it because, obviously, you’ve had some hesitations going into it. I think most of just were the fact that the people in the group probably knew each other. Did you make the mistake of asking if everyone knew who you were?
Rob: Of course not. I never do that. You’ve done that, haven’t you?
Mike: Yes.
Rob: Did you do that at Big Snow Tiny Conf and you’re like, “No, I didn’t mean that. I didn’t mean it that way.”
Mike: Yes, that was my first year because everybody has been talking to each other and I showed up late. I was three hours later than everybody else and it seemed like everyone knew each other. They knew who I was but I wasn’t sure and I just said, “Does anyone here not know who I am?” and as the words left, I’m like, “No!”
Rob: “I mis-phrased that. That’s not what I meant!”
Mike: Everyone laughed. It’s been a running joke for three or four years now.
Rob: That’s funny. Now, Chris had told me that that the folks never knew of me or knew who I was. I don’t know if that’s through being married to Sherrie [ph] because she’s in the group or it’s just that our circles crossed enough. It was nice. There were a few people who just knew me as Sherrie’s [ph] husband and then, when it came up that I was the co-founder at Drip, they were like, “I love Drip.” That was actually cool. I think almost everyone in the group used Drip or uses Drip so that was a touch-point for some folks, which is nice.
Mike: It’s funny that you mentioned overlapping circles because my wife has been spinning up her business and getting into different things with Facebook ad campaigns and this and that. There are certain things that are recommended to her or certain types of products so our circles are starting to overlap in more ways here and there. It’s just funny hearing some of the tools that she’s starting to use, like I either know who that person is or I’ve heard of the tool before and have thoughts and opinions on it.
Rob: That’s funny. You asked me what I thought I was going to get out of it. I thought that being in a room with a dozen successful founders, people who have launched businesses, grown businesses and several who have exited some multiple times, I just thought that there would be interesting conversations and that I would learn something. I went in very deliberately. Within the first day, I knew everybody and so at dinner, I was like, “You know what? I’m really interested in what this guy has to say about content sites, authority sites that have a personality.”
Right now, it’s just kind of article factories, but actually having a point of view in everything. I sat next to him and he asked me a bunch of questions about what I was going to do next and he said, during his process of exiting and then doing his next thing, he made some mistakes so he made some recommendations for that and then I grilled him for quite a while about, “If you’re doing it from scratch, what would it look like if you’d acquire one?” I wanted to pick people’s brains and get an idea of what it’s really like to run all these different types of businesses. I think that’s really what I went in doing.
I came away with not only that knowledge but I was also inspired. I think that, over the past several months, I’m not that motivated to start something new because it’s so much work. As we know and as we talk about on the show and as we’ve lived, it can be really stressful. At this point, I don’t know why I’d put myself through that again, and that’s the struggle, but I also want to do interesting things. I want to work on things that I’m excited about so part of has been helped purely a lot with ZenFounder stuff and gearing up some of that marketing.
In addition to that, I do think that I need a project to just be working on and so I’m trying to strike that balance of having something that’s interesting but not so stressful that I don’t have to work on all the time but I can when I want to. That’s where a SaaS app becomes a really tough sell because it’s just so needy. It’s like having a new baby versus some of these other business models that are a lot easier to have in a mode where you can swoop in, do a bunch of work and then leave it for a while.
Before SaaS, those are the businesses I had and my life was definitely more calm back then. It’s good. That’s what I got out of it, was being opposed to other business models and ways. If I look back at my experience, I’ve always wanted financial freedom and the freedom to work on interesting things and work on what I want. I tried to get that early on with investing in stocks and then I tried to do it via real estate and then I did it via entrepreneurship. Even in the early days, it was not all software. I acquired some e-books, I did had an e-commerce site, I had this whole variety of things and then I got into SaaS. I’ve been through that but it’s like I’ve never been married to a single business model or a single way to make money or have been dogmatic about it. Should we dive into the importance of consistency?
Mike: Sure, why don’t we?
Rob: Hey, it’s the 400th episode, man. We kind of get to do what we want to do today, I think. That’s how I feel about this.
Mike: Technically, we used to do that every time.
Rob: That’s a good technicality. We did get some high-fives and some compliments from a couple of folks. Austin Peak [ph] wrote in and he said, “I just want to thank you. I’ve been listening to your podcast for years and you guys helped inspire me. I can remember the second you changed my life and opened me up to even more business podcasts. It was Episode 240. I was folding laundry in my bedroom. I stopped what I was doing and I wrote down every other podcast you mentioned and it helped change my life.”
That’s kind of cool. Now and again, we get these, “You’ve changed my life,” or, “You really opened my eyes to something that I didn’t see before.” I think you and I take for granted that we just hop on the mic every week, we ship the podcast 20 to 30 minutes, typically, but we really have had a striking impact on a lot of people both through FounderCafe and Micropreneur Academy, MicroConf and the podcast. In fact, I want to roll an audio clip here from Fatcat Apps’ own David Hehenburger.
A3: Hey, Rob and Mike. This is David Hehenburger. I’ve been listening to your podcast since the early days and it’s had a huge impact on me. The biggest thing was when I first listened to the podcast, I was stuck in a consulting business that I wasn’t really trying that much. By listening to your podcast and following your Rob’s advice of stair-stepping, I was able to get out of consulting, launch a number of successful work-less plugins and now, over the last of year, also launched a successful SaaS app. This podcast has just had a huge impact on me. Thanks so much for everything, guys.
Rob: Mike, I don’t think we toot our own horns very much and I think that’s probably a good quality. We come across as authentic on the podcast because we are just who we are, but I think the 400th episode is the time when we can celebrate what we’ve done, what we’ve built and the impact that we’ve had on people. I was perusing our very ancient website, startupsfortherestofus.com. We need a facelift on that thing soon, but there’s a Success Stories tab and we stopped updating this a while ago.
Basically, we did a call at one point for people who had listened to the podcast and launched a product that allowed them to leave their day job. There’s about 20 names on it and, again, we added names for a couple of months and then stopped. I know that there are more people impacted, but Kevin Taylor from Beam Calcs, Duncan Murtagh from Vetter, Tom Fakes from FHRNews, Phil Derksen from WP Simple Pay, David Hehenburger who just sent the voicemail in, Jerome Samuels, Brecht Palombo from Distressed Pro–a lot of folks don’t know that he was an early member of the Micropreneur Academy and said that he implemented a bunch of stuff that we’d mentioned in there–Jordan Sherer from Widefido, Nate Grahek from StickyAlbums–StickyAlbums, as far as I know, is a seven-figure business. He’s very succesful in the photography space and eh had just been a long-time listener, Richard Chen from phpGrid and there are others.
I think it’s cool to do that. I think, for me, a lot of times, it doesn’t feel real. What’s your take on it? How does all that resonate with you?
Mike: I agree with you. I think I’m in the same camp where I don’t think about it often. Occasionally, we will get somebody who writes into us a set of questions at startupsfortherestofus.com and says, “Hey, I just wanted to let you know we did this and would you mind putting our link up under the success stories?” We obviously don’t go and update it a lot but there are occasions where people will write in and say something, saying, “Hey, you changed my life,” or, “We implemented this,” or, “We launched this new app that got me out of a job that sucked.”
We will do that on occasion but I don’t think about it too much, I guess. Maybe I should but I do know that, obviously, I see the stats and stuff. It’s hard, in many ways, to associate an email address or a blip on the screen from some metric someplace with actual people, I’ll say, because there’s that level of abstraction. I actually teach people this when I’m talking to them about Bluetick because in every email address there, there’s a person behind it. You have to treat it that way. I think it’s very easy to lose sight of that especially when you’re looking at all these different marketing tools that measure this or analyze that. It’s like every single one of those has typically keyed off a person.
Rob: Yeah, and I think we made a good move in launching MicroConf. I remember the reason we did it and it was because Micropreneur Academy had a community it was building and we wanted to meet people in person. The fact that we now know, in person, face-to-face, by name, so many podcast listeners, I think, is a unique thing because if we didn’t have MicroConf, how would we have met all these people? Maybe at BoS or maybe at other conferences, but that has helped me understand who are audience is more.
I think it’s also helped shape some of the content that we produce and how we talk on the show. There are days when I will outline a podcast while we’re on the show and I’m saying something almost specifically to one person based on either one conversation I had with them or just the persona of, “Yes, this person with these WordPress plugins, this episode’s for you. These are all my thoughts that I would tell you if I had the time to do an individual call with you but, instead, I’m just going to record this podcast.” I think that’s been helpful to have real people on the other side of the earbuds because a lot of podcasts don’t have that.
Think about if you had 20,000 listeners and you didn’t have a conference. How would you possibly know the people who are listening?
Mike: Yeah, you have absolutely no idea. I do the same thing to some extent as well on occasion in an episode and there was somebody who emailed me earlier in the week or earlier in the month and said, “Hey, what are your thoughts on this?” and, a lot of times, I’ll reiterate them through the course of a podcast episode because you can be a lot more expansive on a podcast episode than you can in an email. I have tried to cut down on the length of the emails that I write these days but it’s easier to talk about it and just do a podcast episode on it than it is to drill into all the little details and edge cases in an email versus somebody asking for advice about a specific thing. Speaking of which, we should also put out a call and say, “If anyone has questions that they want answered for the podcast, this would be a good time to send those in because we’re running low on questions,” I believe. Is that correct?
Rob: That’s correct, yep. If you can, you can call into our voicemail or send us an .mp3 file or even just drop us an email because we are almost out of them so we would get your question quite soon.
Mike: We’re accepting emails now?
Rob: Accepting emails and accepting five-star reviews on iTunes. I’m kidding. I wanted to run through just a couple of favored and most popular episodes but it’s hard to know what resonates with different people. I remember Episode 47 was Movies for Nerds and it was a bunch of startup tales, and I remember that being a big deal for a while. I think it had our highest listenership of our first 50 episodes for quite some time. Then, a favorite is always the podcast for startup founders. Episode 104, 240 and 395 are basically that episode. It’s podcasts and we’ve updated that several times. Then, Episode 255, Moving on from AuditShark, seems to have gotten a spike in listenership on that one and some extra-popularity which I think is interesting. You can still get that one in the podcast feed. I think the feed goes back to Episode 254. Are there any others that you remember offhand or do they all start to blend together at some point?
Mike: I think they blend a lot, to be honest. It’s hard for me to go back and say because I was there for the entire conversation so it’s hard for me to point to any particular one where it’s like, “That really stuck out to me,” or, “I listened to that half a dozen times,” because I was involved in the discussions. There’s not many that really pop out. It’s like, “This is interesting,” although I have heard people who have commented on the Moving on from AuditShark and how difficult that was, especially leading up to that whole decision.
Rob: That makes sense. I have gone back periodically and I’ll just go back and randomly pick 10 episodes. I might go back a year or even a year and a half. I’ll go back to that early podcast feed or as far back as it goes, which I think goes back 150 episodes so I guess that would be almost three years. I’ll listen to 5 or 10 in a row and it’s kind of fun to walk down memory lane. Typically, you’re either working on AuditShark or just moving on. I’m working on Drip or, even before that, HitTail.
It’s interesting for me to see what I agree with that we say and what I disagree with. I think things change that quickly, that there are opinions that one or both of us had that I’m like, “You know what? I don’t think that holds true anymore,” or there’s things that we say that I’m like, “Wow, that’s really insightful. That’s a pretty smart thing. “It’s not patting myself on the back; it’s just like, yeah, Mike and I had a really solid answer to that listener’s questions or a solid take on pre-launch email marketing or that kind of stuff. It’s fun to do that. I don’t do that much but, when I do, there’s definitely some good content on the show, I think.
Mike: One of the things I wonder about is, a long time ago, we’ve made the decision to put the transcripts of all the episodes out there partly for SEO reasons but also just so that it made it easier for us to go back and search through if we’ve found something. I think that we’re still very happy that we made that decision even though it cost money for every single one of those transcriptions, but what I find interesting about what you just said is that when our opinions on something change, there’s still that record of what our opinions were at the time. I wonder if there’s any confusion that could potentially be drawn out of that by people who search for something and then say, “This is what Mike’s and Rob’s opinions were on this back in 2014 or something like that,” and maybe that leads them down the wrong path. I wonder if that’s a nonsensical concern but I’m thinking about that too much.
Rob: I don’t know. People have definitely asked for an updated take on certain topics. I guess it’s hard to know or impossible to know.
Mike: Yeah, you wouldn’t know unless somebody said, “Hey, I followed this advice,” and then you’re like, “Yeah, now that you asked me again, I’m thinking about that and I would do something different now versus then.” That’s part of the value of having that transcript or being able to say, “This is from four years ago or five years ago.” People can also take that in context and say, “It’s from X years ago. Does that still hold true?”
Rob: Yeah, that’s true. I think you’re leading us to the topic of today’s episode, which is probably just going to be a short conversation at this point because I feel like this has been good. Just reminiscing and talking about things, I think, is fun to do. We don’t do that very much and so it’s interesting to think about. We titled this one The Importance of Consistency and I think the consistency of showing up every week has been perhaps one of our biggest weapons or one of our biggest strengths in building the podcast.
I know, early on, we did every week and then we ran at a content about 20 episodes in and then we started going every other week and realized that the listenership was not growing at all. Then, we made it a commitment and we also made it easier. We make it so that we show up, we record and then our editor does everything from there. I think that was a game-changing issue for us, getting someone who we can essentially pay to really get the show produced. That’s the only reason.
I think the two reasons we’ve been so consistent–I know from my perspective–is, number one, because it’s not a ton of work for me. Even in the busiest and most stressful days of growing Drip, selling Drip and all of that stuff, I knew that I could show up on the mic for about 45 minutes and you and I could record and that it would be there. It’s very, very rare that you or I miss an episode because we’re too busy. I know if that ever happens. It’s always because there’s a vacation or we have a scheduling snafu or something.I can’t remember a time where you were like, “You know what? I’m just swamped this week. I can’t record.” It just doesn’t happen. We’ve prioritized it and it’s on both of our calendars. That’s the other thing. If this was a solo podcast, there would be so many weeks where I wouldn’t show up, but the fact that I know that you’re going to be there means I can’t leave you hanging.
Mike: I think that has to do more with accountability and having yourself accountable to somebody else. It’s like a gym partner. If you’re going to the gym by yourself, it’s a lot easier to fall off the wagon than if you know that your buddy is going to meet you there and you’re going to lift weights every Tuesday or four to five days a week at 7:00 AM. Somebody else is depending on you to be there.
Rob: Yeah, that makes sense. As you pulled a couple of references, there’s an inked.com article, differenceconsulting.com and [0:30:13.5] Express. We’ll link them up in the show notes but these are talking about consistency and the power of it.
Mike: Yep, and I think the first one is that, for me at least, consistency builds predictability. For other people, it’s essentially eliminating the unknown. We drop this podcast early in the morning every single Tuesday almost without fail except when there’s a technical glitch. When that happens, there are people who will email us and say, “Hey, I don’t see the episode out there. What’s going on?” Everyone knows it’s going to be there and if there’s something that comes up where we’re going to need to record an episode in advance, we make it happen. We always have a contingency plan. We plan ahead and make sure that that’s going to happen because we know that if we don’t, we’re going to get emails, tweets and things like that like, “Hey, where is the podcast episode?” That happens when there’s a glitch, but we don’t miss the episodes.
Rob: That’s right. Even in the weeks of MicroConf which are super busy and taxing for us, we record ahead, in essence. We get an episode or two ahead. I was thinking there was one episode that was about 40 episodes ago so probably around 360-ish where you went on vacation or something happened last-minute and I was trying to get a guest and I couldn’t.
Mike: It was Episode 360, the one where Rob takes over the show.
Rob: Something happened where my guest fell through and I couldn’t get anybody online. It’s just a solo episode and I comment in the episode like, “I’m doing this because we need to ship something and I’m just going to talk to the mic.” I answered a bunch of listener questions that day and it was actually fun. I wouldn’t want to do it every week but it’s that kind of thing of just making sure that we get something into your earbuds every Tuesday morning.
Mike: Interesting that you said you’re going to talk to the mic.
Rob: I know. Consistency has done a lot for us. It builds trust. It’s predictable so it eliminates unknown for folks, and I think these articles were saying it shows dedication. It shows that we’re committed to something. I think subscribing to a podcast and sticking with it is a commitment. It’s a bummer when I subscribe to podcasts and I get invested and then they just pod-fade and they disappear. It’s like, “Man, this sucked.” I think the fact that we do have this many episodes can be a show of dedication and allows people to trust us more that we’re going to keep shipping.
Mike: Right, and the other thing I think is interesting is that, early on, what our main goal with the podcast was, really, to help promote FounderCafe but I think that that changed over time because we really don’t promote FounderCafe too much on the podcast. In fact, I’ve heard from people, “You should.” People tell us, “You should promote FounderFace a lot more on the show because, then, you get more people into it and you get more conversations and there’s the whole network of facts that can go into that.”
If you are interested, go over to foundercafe.com. There’s an application that you can fill out. It’s $100.00 per quarter and it’s a set of forums that you can join to interact with and ask questions of and get information from people about whatever it is that you’re working on, whether it’s a new marketing campaign or you have a question about how to use a particular product or what other products people would recommend for a certain situation. Definitely go in there and check it out. The application process is really just to help filter people out that are not a good fit. There are people where we’ve essentially turned them away because in the application, we ask what they want to get out of it and, if they’re not going to get out of it, what they would expect, then we’re just going to say, “Hey, look. This is not a good fit for you.”
Rob: Yep. It’s an online community of seasoned entrepreneurs just like you, and we do a really good job with the application process in making sure that we get folks in there who are going to help each other succeed in essence foundercafe.com.
Mike: I think the other interesting thing about the podcast and how we’ve been so consistent over time is that, as I said, we changed what the main reason that we’re doing it early on was but, since then, one of the things that comes to mind is back when we first started the podcast, there really weren’t any other podcasts that were like ours or was catering to our audience. It’s interesting that there are a lot of other podcasts that have popped up that are, in a similar vein, startup founders, working from home, boot-strapped or self-funded and building something and just talking about it. I think it’s really interesting to have seen those but early on–and, again, not to toot our horn here–we’re trailblazing. At this point, we’re no longer trailblazing. We’re like the old horse on the track.
Rob: That’s true. Sometimes, I wonder if someone comes along and says, “You have 400 episodes? That’s either really cool and shows you’re consistent or it’s overwhelming.” They’re like, “Well, I don’t want to get into this show. There’s already 400 episodes. I can’t possibly catch up.”
Mike: I was going to say potentially demotivating to certain people because they’re like, “I would start a podcast but these guys have got hundreds of episodes. Who would listen to me if these guys are going that strong or going for that long?”
Rob: Yeah, I wonder if it cuts both ways. I was thinking more from a listener perspective, someone who decides to subscribe or not. 400 episodes could honestly discourage them because they just can’t catch up. It’s like, “Well, I’ve already missed all that.” It’s like coming into a show or hearing about it when it’s five seasons and it’s like, “Why? I don’t think I really want to watch all that.”
Mike: Yeah, I’m not sure. That can happen with TV shows and stuff like that like The Sopranos. I’m never going to go and watch that. It’s just not going to happen.
Rob: I know. I’ve heard it’s so good but there’s too many episodes. There isn’t too much good TV out these days.
Mike: I think that’s a little bit different from what this podcast offers just because in this podcast, every episode is different and you can take it as a standalone thing versus something like a TV show where if you’re not really involved from the beginning, it can be hard to get in there. I think General Hospital has 14,000 episodes or something like that. It’s some ridiculous thing. They’ve been going since the ’60s or ’70s and they just drop a new one every week. I think Sesame Street has some ridiculous number as well.
Rob: You can drop into them. I think our podcast is more like Law & Order because it’s episodic. It’s like a single episode, start to finish, you can get value out of it or you can follow the story over the years. That’s what I’ve heard from people who liked the podcast, is they say they came for the content, originally, and the tips and the tactics and then they stick around to hear what we’re up to, in essence.
Mike: I guess it can go either way, then. What do you get out of the podcast these days?
Rob: That’s a good question. I don’t know that I’ve asked myself that question in a few years. I think, early on, it was definitely because there was no other content like it and I felt like it should exist in the world. I wanted there to be people talking about this stuff much for the same reason that we had Micropreneur Academy and FounderCafe and MicroConf because we wanted them to exist in a world and we wanted to be part of those communities.
That’s what the podcast was in the early days as well to promote what’s now FounderCafe. Then, over the years, I think, it’s certainly helped with Drip because just having the audience as an early seed, an early customer group, was helpful. These days, I don’t know. I don’t know that I can point directly to something right now that I’m gaining from being on the podcast but I do enjoy it, if that makes sense. I don’t know that I gain anything by playing Dungeons and Dragons with my 11-year-old but it’s fun. I have gotten things out of it in the past. It’s worthwhile, certainly, to show up and do the show because it has yielded so many things, I think, for both of us.
Mike: I think I would call a random benefit generator, like you don’t know what the benefits are. It’s hard to point to any specific thing like, “By doing this podcast, I’m going to get 75 new people added to my product and I’m going to make these certain relationships.” I think it’s just hard to predict those in advance or, even at the time and, say, “Down the road, I’m going to get these benefits out of it.” There’s definitely examples you can point to in the past, but I think that there’s a lot of things that you just get this random set of benefits moving forward that’s hard to nail down and say, “This is what I get out of it.”
Rob: Yeah, that makes sense. Someone said a portion of the value you put into the world, you get a small portion of that back, and I think that’s a really apt and insightful thought, and that has been true in my experience. I think that, by putting the podcast out, there’s value created in the world and they put in the hard work. The founders who listen to this, they put in the hard work. If we had some type of influence or motivation or we provide something for them, I think there’s a lot of value created in the world and a little bit of that does wind up coming back to us, whether it’s the ability to sell at a conference, whether it’s business opportunities or whether it’s if you or I needed to raise funding to do a small, bootstrap kind of angel round.
I think that the podcast has made that so much more possible for us, and we’ve had other avenues as well. Obviously, I still have an email list from my blog. I have the book list. There are other things that we do but the podcast is probably the thing that you and I have done. Certainly, for me, it’s the thing I’ve done with the most consistency because of what we said earlier. We’ve made it pretty streamlined and it’s enjoyable and because of the commitment to do it. Imagine if we missed a week.
Mike: I think the internet would freak out for a little while.
Rob: It would feel really weird to me to not have an episode or if we decided that today was the last show. At 400, we’re just going to be done. That would really be odd to not be putting something into the world. I think that’s the thing, is blogging is so time-consuming and as much as I loved doing it, just once the business has gotten in the way and I needed to focus, I had to stop blogging. I made that decision to do it, but I still want to be able to put thoughts into the world because I am experiencing new things and I feel like I still have things to teach and share with people, and the podcast is such a good way to do that because of the low time commitment.
Mike: I also think that it’s a better medium for doing it than a blog post where somebody might hit upon a blog post and they may or may not read it. If somebody subscribes to your podcast, it becomes a much more intimate experience where they feel invested in the story and the people who are doing the podcast, and I don’t think a blog can raise that level of connection between the reader and the author versus something with a podcast, like you’re in their ear. Your actual value is in their ear.
Rob: It’s definitely much more engaging, and I think we learned that early on. I talked to a few podcasters who are also bloggers and, in our early days, I remember my blogging audience was 10 times the size of the podcast audience but I felt like the podcast audience was so, so much more engaged and so much more willing to interact with us. Now that the podcast audience has grown to what it is, there’s just a lot of value in having people listening in through the earbuds, as you said.
Mike: I guess we should at least give one tip for consistency, though, because we’ve talked about the importance of it but we haven’t actually talked too much about any sort of tips for maintaining consistency. We talked a little bit about having an accountability partner or something along those lines. I think we briefly talked about what the goals are, the benefits of doing something for a while. Do you have a tip that you can share for consistency?
Rob: You just couldn’t let it go, huh? You had to go with the patented Starters for the Rest of Us formula of providing some kind of tip or tactic in every episode.
Mike: You want to give that tip on the next episode? That’ll be the cliffhanger for Episode 400?
Rob: I have a couple of tips and it’s what I’ve just said. If you want to be consistent, have that accountability partner where you have to show up, make it easy or reduce all the friction you can. If you want to be consistent about going to the gym, have all your gym clothes already in the car so you don’t have to look for them in the morning. Just make it easy, and that’s what we’ve done with the podcast, is hiring an editor and making the process so we just let this get put into Dropbox and then it magically shows up in my feed five days later with the transcript and all that. I think those would be my two biggest ones, is remove friction and try to have someone else busting your chops if you don’t show up.
Mike: I think those are good ones to leave off with. If you have a question for us, you can call into our voicemail number at 1-888-801-9690 or you can email it to us at questions@startupsfortherestofus.com. The theme music is 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 the full transcript of each episode. Thanks for listening. We’ll see you next time and thanks for sticking with us for our 400 episodes.
Rob: Nice work, man. High-five on 400 episodes. I’m pretty proud that we’ve done this.
Mike: Me, too.
Episode 399 | How Derrick Reimer is Validating His Ambitious Third SaaS Application
Show Notes
In this episode of Startups For The Rest Of Us, Rob talks with Derrick Reimer, co-founder of Drip, about his new SaaS application Level. They talk about what inspired the idea as well as ways Derrick went about trying to validate it.
Items mentioned in this episode:
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.
Derrick: I’m Derrick.
Rob: We’re here to share our experiences to help you avoid the same mistakes we’ve made. How are you this week sir?
Derrick: Well, I am deep in the process right now of building out some mockups of my new app called Level, to hopefully get some more concrete things in front of some of my early access list folks.
Rob: That makes sense. If folks are interested just right from the top, level.app is the domain name. You have a really tight landing page. If you’re listening to this and you want to see–this is maybe 400 to 500 words of text–and it is on point. You’ve got the headings, you can skim it, at the bottom is fomo, the reserve your handle today, you can claim a little slice of real estate on level.app. Then you have the social proof, right? 3,542 people who have reserved their handle including me, and so if your name is Rob, I’m sorry but I got level.app/rob. How’s the landing page working for you?
Derrick: It’s working really well. That is actually a live query now showing the current count. It works surprisingly well. I wasn’t sure exactly what to expect when I first built that but I figured that the scarcity play would be effective. I and had a few conversations with folks at MicroConf too, about this. I saw their eyes light up, and they’re like, “Oh yeah, make sure to let me know before you do that.”
Rob: That’s when you know you’re on to something.
Derrick: This is a good sign. They can appreciate it from a from a marketing ploy and then they’re like, this kind of instinct of, “By the way, I really want to know when you do that so I can get mine.”
Rob: For those listening, if you don’t know what Level is, it’s an alternative to real time chat designed for the software development workflow. I just pulled that right from your landing page but it’s ostensibly a competitor to Slack but a much less interruptive experience. More asynchronous, not the blinking red dot, I guess it’s not blinking in Slack but everything’s synchronous by default. In Slack and you’re going for the opposite in essence, and this stems from?
Derrick: From really my experience with Slack. My first time using Slack was with Drip when we were a team of like two or three. It was not painful at all at that stage, but gradually, as our team size grew, it started to get a little bit more cumbersome. I remember actually, the first time I was in a “big Slack,” team was in our building back in Fresno. That was like an early warning that, “Hmm, I think this maybe doesn’t scale so well as your team grows.”
The building chat was full of just folks tossing around various pieces of information, most of them not urgent but often pushed through with an @channel or an @here, “Hey, there’s some cookies in the in the kitchen.” And it’s like, “Do I really need to get pulled out a flow to hear that piece of information?” That was like an early sign that Slack seems kind of broken especially when there’s a lot of people chatting back and forth.
That experience was reinforced after we were acquired by Leadpages and we joined the broader company wide chat. There was about 150 people in there, and a really similar experience where a lot of well-intentioned people who weren’t trying to interrupt each other, but the tool just kind of failed as in essence and made it really hard not to accidentally interrupt people’s flow. Level is really kind of a reaction to that problem. I just observed this over the course of years and I just couldn’t get it out of my head, so now I’m building my take at a solution.
Rob: Yup. You wrote a manifesto a few months back and published it on your blog derrickreimer.com. I see now you’ve you republished it at level.app/manifesto. In essence, you’re describing the pain points you’ve just indicated—of the interruptive stuff in your story.
Derrick: Yeah. The manifesto was kind of step one actually for introducing the idea to the world. I didn’t really waste any time after moving on from Drip. I think I’ve published it on my last day at Drip, is when it kind of soft launched. Then the following Monday, I really did a big push in the manifesto. I was just sort of itching to get this out into the world. That promotion was probably, I think it worked really well because it sort of made a splash, it made a bold statement. I was able to gather quite a few email addresses off of that. I think it was maybe 300 to 400 within the first couple of days, and so that gave me a nice launching pad of folks to start engaging with. Obviously, people sharing it around on social helps too. I think that was a really effective strategy for making the first intro to the world.
Rob: II know you had kind of been noodling on it for awhile just in the background in your head and because we’re faced with the limitations of Slack everyday working on the Drip team, and you left Drip was it February of this year or was it March? I guess it was three or four months ago?
Derrick: Yeah, three or four months ago. Beginning of March, yeah.
Rob: Because that’s the more important thing for someone who’s listening to this two years from now, they don’t care what month it is. You hit the ground running. When you published the manifesto, I remember you wrote it up in a Google doc and then you had a couple of friends come in and edit and make suggestions and all that stuff, and then you published. What is it Twitter that gave you most of your sign ups? Because I remember, it didn’t go up in Hacker News, right? It got a few or something but it didn’t make it to the front page which I was frankly surprised by. How do you think you got those 300 or 400 sign up for someone else who’s thinking about doing it?
Derrick: It was predominantly Twitter. I think that was effective particularly for me because this is a product that’s marketed towards developers, and that’s kind of the premier place where designer, developer types hang out online. I think that was where most of my strategy was focused was trying to get people to retweet it, to like it, to share it. I did assemble a list of folks who are in my inner circle, friends of mine who also have a decent following on Twitter and did manual reach out to those folks just to tell them, “Hey, I’m going to be sharing this thing, if you wouldn’t mind, could you please tweet it out to your followers?”
Most people are really eager to help out. I think it’s where a lot of the lift came from. I did actually try running some Twitter ads that day. I didn’t really tuned the audience too much. I just let Twitter auto choose that by hitting the promote button. That drove probably 30% of the impressions for it but zero activity. I would say majority, I think I put in maybe $100 into that just to see if this is going to help provide any additional lift. I think a majority of it was really organic shares on social. I also emailed my own personal newsletter list which is pretty small just like a couple hundred folks on there at the time. I think I generated some shares off of that as well.
Rob: I could imagine that. I remember there were some comments, I think it was on Twitter but my favorite comments are always the ones that completely missed the point of an article. I would spend eight hours writing something. I know you spent a lot of time writing this, and then you have a one sentence that has something that is debatably, maybe factual, and someone rips into that, and you’re like, “Dude, that has nothing to do with the point.” There was one of these sentences we’re talking about, “Yeah, once we started using Slack, it was great. This is not news now, but five years ago, it was pretty groundbreaking.” There were somebody like, “Well, 12 years ago or 15 years ago, I was using IRC.” That’s not really the point, what are we even talking about right? Did you did you have much of that or was it the minority?
Derrick: It was very much the minority. I think it was on Reddit actually, and maybe I sort of attracted some of that flaming because I did post my own manifesto on there which I know is a little bit against the way you’re supposed to use the service. I was like, “Oh, what the heck. I’ll just post it in the developer subletter or whatever.” Some people took issue with the timing of when Chat was invented. The whole notion of arguing that this whole argument is invalid because I got the year wrong on when it came to the forefront, it was just laughable.
Rob: Yeah, it is what it is. Luckily, that tends to be the minority thing but it does always side track. That’s actually one of the reason that I completely disabled comments on my blog. I got tired of those conversations going on. There were good comments, and then just the ones that were irritating, or ill-informed, or just obviously looking to nitpick stuff. That’s just not helpful. That’s been my own personal journey with that.
You posted the manifesto, you got a few hundred emails, and you’re on the Art of Product Podcast with Ben Orenstein, mutual friend of ours, and you’ve been talking about your process through that, so I’m sure that that has helped get other developers interested in what you’re up to and probably slowly built your list over time. Once you had that list, what were your next steps? Because I know that you and I had talked about this a while back. This is a very ambitious project, and it’s either going to be awesome, or you’re just going to get smoked by Slack. They’re just going to stomp you, or not even notice you, and no one’s going to switch because of the high switching costs. It’s one or the other, and you’re fully aware of that upfront. What were your early steps of trying to validate the idea a bit more than just positing, “Hey, I can build a better Slack.” It’s like, “Okay, step two is…” What are you up to next?
Derrick: I was definitely leery of making the classic mistake of taking a little bit of early indication that we’re on to something, and just running with it and not talking to anybody—which is a mistake that I’ve made before in the past—and so many folks do. I really wanted to air on the side of having too many conversations with people to try to asses out is this, “Am I on the right track with this? Is this actually going to sell well in the market?”
I think it was within a few weeks after launching the manifesto, I sent an email out to the list. I decided to email the entire list which looking back was probably should have started with a smaller slice just to gauge what the response rate would be. But I basically emailed out and said, “Hey, thanks so much for signing up. I want to have a conversation with you and hear more about what your pain points have been with real time chat in the workplace. At this point, I’m not trying to propose any solution to you beyond what I’m kind of alluding to in the manifesto. I really just want to hear what particularly about real time chat isn’t working for you enough that you gave me your email address.”
I sent this out and I sent a Calendly link with that so that people could book a 20-minute slot on my calendar. I kind of reserved it to afternoons only, thankfully, to reserve the mornings for productive time. I think I got around 40 people booking time on my calendar.
Rob: Dope. That’s both really good news and also like, “Oops,” Were they 20 minutes each? What was that? 16 hours?
Derrick: Something like that. It turned out to be basically three and a half to four weeks of afternoons booked pretty solid. At first I was like, “Oh boy, this is a lot.” But I think, at the time, it’s early enough, I’m like, “This is probably where my time is best spent. Talking to people and hearing in their words what problems they’re having.” That did help guide the way I would thought about the product. I would say influenced where I thought the biggest emphasis should be.
I wasn’t sure if the emphasis should be on reducing interruptions, or just organizing content better, or should I be focused around really optimizing for asynchronous, where are the pain points actually. It helps clarify my thinking. One of the things that we’ve talked about a lot that helped in the early days of Drip was just getting feedback from people and looking for patterns. What are the things that we’re hearing over and over again, and those are likely to be things that we should be paying attention to. I did spot some of those themes and patterns. Looking back, it was helpful to have a decent sample size. If I’d only talked to 10 or 15 people, then that may not have been enough to spot patterns. I think it was good overall.
Rob: Yeah, I know it was a lot of time. It seems like you were learning quite a bit as you were going, and at that time, you didn’t have any mockups right? You really were just talking through how would this sound, or how would you use this, or that kind of stuff.
Derrick: Yeah. I tried hard not to actually tip my hand on what I was thinking. I just wanted to hear unbiased people’s take on like, “You know, if there’s one thing I could change about Slack.” or I ask questions like, “Do you use Slack threads and what do you think about them?” Or, “Do you use search heavily in Slack?” Just to get an idea of like how much are people relying on the tool to be their source of the repository of historical information, versus how much is just ephemeral conversations that get transferred into project management tools. There was a lot of things I was just trying to learn and SaaS out from people without tipping my hand too much on my thoughts of a solution.
Rob: Right. In the back your mind, obviously, you know that you need some kind of differentiation, pretty strong differentiation from Slack because everyone’s going to immediately compare you to Slack. One thing you’ve chosen is to niche down to developers, right? You know that interruptions piss developers off. It breaks your flow. You and I have experienced this first hand as our development team grew.
I used to tell people snooze your Slack for two hours, do not disturb it during this time, just try to get focus so that we can continue ship code at high velocity. You have that but there was there was one other thing, that early on, you made a decision to do that is potentially risky but it’s another differentiator. You want to talk a little bit about that?
Derrick: Sure. You and I noodled this little bit when I was just in the idea stage, and I think we were having drinks one day and I was like, “Alright. I think I figured out the one thing that’s going to really make Level stand out. Let’s open source it.” You spit your drink all over my face. There are examples of this happening, there’s Discourse, there’s Ghost, there’s GitLab, so there are companies that are already doing this.
Rob: Not in the chat space, those are in other spaces but it’s a mockup.
Derrick: Yeah. I will say there are other open source chat tools but I don’t think they’re really making any kind of headway as a business. They’re just open source only. The model of open source, the core code base, but then charge people for hosted version of the service is basically the model that I’m going for. The thinking behind it is that one, since this product is marketed towards developers, a lot of developers sort of appreciate when things are open source, when they can look at the source and see what’s happening with their data, and just sort of have that transparency, and also be able to download it, and stand up a cluster of servers, and manage it themselves if they really want to do that.
I’m sort of banking on the fact that most companies that have sufficient budget to pay for a tool aren’t going to want to go through the hassle of managing their own servers, and patching them, and keeping them up to date and all that kind of stuff. They’re just going to want to pay me for the hosted version. But if you don’t have the budget or if you’re bootstrapped, and you’re really scrappy, then by all means, download it, stand it up on your serve, and when you’re ready, you can transfer the data into the hosted service.
Rob: This was, in essence, around that you and I kept talking about, how you can have a free plan because I think you need one. We both thought you need one because that’s kind of part of the course in the space, and how are you going to do that as a bootstrapper, and not get killed by hosting costs, or not get killed by support and all that, and this is a way to do two things. That’s pretty ingenious if it works, and it’s, like you said, developers or more tech-oriented folks, this is in essence the free plan in addition to the benefit of it being open source which most people like, and then they can pay you for whatever the hosting, and the support, and as an almost SaaS app.
Derrick: Yeah, exactly. It’s not only the free plan but it also kind of paves the way for potentially offering on-prem if I’m sort of optimizing for the ability to setup the entire service from the ground up easily as opposed to just running a SaaS app or maybe you kind of cobble together your own hosting situation that’s not easily replicable. I think building it in this way paves the path for companies that don’t want to run a hosted service, or trust another company to run a hosted service for them, they can download it, and run it inside their firewall too.
Rob: Yeah, and that’s really interesting. Can you do that with Slack?
Derrick: No, I don’t think so.
Rob: There’s no on-prem version as far as I know. That could be an interesting enterprise play. I know that wouldn’t necessarily be the market you go after first, but if you get traction, you get name brand, and people are like, “Hey, not only is this open sourced–” which big companies tend to. They either hate it or love it, but if they understand it they’ll love it, and then like you said, you can do the on-prem play, and those are super expensive, that would be a really nice, high-end revenue source for you if you’re willing to put up with the headaches.
Derrick: Right. That probably would be down the line where I have traction, and a team, and I could kind of establish a team to run that end without me having to do all the sales and all that kind of stuff.
Rob: Totally, yeah. After you got all of the information from those Skype calls, I know you and I then met. I know you did a bunch of thinking on your own for a couple of weeks and then you were at a point and you said, “You know what, I have thoughts, it’s not ready to go into mockups yet. It’s not ready to build a UI. I have a bunch of ideas about different message types and how to structure these, let’s do wide port session.” And so you and I met at the local library, actually, in a nice little room, and you wanted to talk about I think, the value of that, or what that felt like and just the point of doing that.
Derrick: A lot of times there are these key points when you’re designing products where it’s like, there’s a lot of information scattered about and kind of coalescing that information into something actually tangible. It’s hard to hold that all in one person’s head, I feel like. I tried doing a little bit of solo whiteboarding, and I jotted down in a notebook, and I probably could have arrived at similar conclusions, but I think it would have taken a lot longer and probably wouldn’t have been quite as crisp and clear.
We whiteboarded for probably an hour and a half or two hours. I think we came away with some really concrete takeaways. It kind of started with like, “Okay, I have all these types of messages that people send in Slack. There’s water cooler type chat. There’s people shelling their work. There’s people announcing things to their team. There’s synchronous discussions maybe around an incident, or something happening in production where we’re needed to go back and forth quickly, and there’s people requesting something from someone else, or maybe things blocking their work.”
I had this long list of things. I was like, “Okay, I need to kind of build up what’s similar about these, what’s different, how will the application know what types of message do I need to ask the user to tell the app what type of message this is, or can we infer it. Then, how does this translate into a priority and notifications?” It was sort of like a really central piece of the application. I felt like I couldn’t just start designing UI because it all kind of hinges on how each of these types of messages is treated. I think this was a really good candidate for whiteboarding, and yeah, I felt kind of like we’ve reignited some of the magic from the Drip days–it was really fun too and motivating. I would say, if you’re solo founder, I think it can be really valuable to find a friend that you have good rapport with, and can kind of brainstorm with, and bounce ideas off of, and just get there kind of two brains thinking about the problem, it can often lead to a really great result in the end.
Rob: Yeah. I was, I don’t know–concerned is probably not the right word–but going into it I was like, “Uh-oh, Derrick’s been thinking about this for months and I’m way out of that whole process. Are we going to be able to rekindle the old magic?” On Drip, we just used to whiteboard all the time, and came up with really good stuff–I thought. I use to say, with the two of us in the room, it’s like 10 times better. We catch all the edge cases and it’s like you said, two people holding the whole thing in the collective heads rather than one person trying to do it. There’s always a back and forth, there’s your sanity checking, there’s just the collaboration, it’s just night and day. If you’re standing in front of a whiteboard on your own, I think you and I really found how different that could be when we started collaborating right on Drip.
Derrick: Yeah, because you’re thinking about stuff, and you reach these points where my train of thought hits a dead end. If you don’t have someone there to kind of either pivot it or just pick up where you left off, then it can be a really frustrating process. You feel like you’re slogging through mud, and just having a pair there to help keep things moving. There were times when we would sit there and just kind of stare off in the space for a minute or two, and that’s okay too. It was a really fun exercise.
Rob: I agree. Being comfortable with silence too. We’ve talked about this when I came on your podcast. If you are going to whiteboard with someone, one or two people, I don’t know if we ever found a third who is as in our own heads as we are, as in the flow. We certainly had some good collaborators at Drip but you and I can sit there for five minutes with complete silence and not feel weird. I think that’s a big thing is you let the other person think and you’re thinking as well.
That’s the other thing I think with whiteboarding is oftentimes, if I try to do it on my own, I’ll get to a point and I just get stuck. I just can’t get past this and that’s when you will step in, and be like, “What if we think about this?” It’s like, “Oh.” Now you got us past it, and we’re still in the flow, and then we could finish the whole rest the hour. But I would have stopped there and just got hung up on it for a day, potentially. I think that’s a good point where you’re like, you could have gotten there eventually but it may have taken you weeks, and it was 90 minutes or whatever for us. That was super fun, by the way. I came out of that feeling great.
You came out of that then with kind of a mental model of message types, and not quite UI. I know we threw you why ideas around. We never sketched anything but it was always kind of hand wavy and talking as we’re like, “This alert to do this in this flow.” Then did you go straight from there into mockups or what was your next step? I know there was a vacation in there as well, right?
Derrick: Yeah, I did take a little vacation. I’ve been having this feeling of like a little bit of guilt as a product person that I should be getting some more concrete ideas in front of users to get feedback—sort of what I alluded to at the top of the show. I did try to take a stab at building some mockups. I’ve been working on them for a little while now. It’s taking a lot longer than I expected. I think part of that is that, we had some concrete ideas formed from the whiteboarding session but like we said, they’re not actual envisioning of where the pixels will sit, and how the product will actually form together. It was still a pretty fuzzy vision of it.
It felt like I had a lot more work out of my head than I actually did when I started to lay out UI elements. I think that’s probably true of any idea where it’s easy to sort of picture this thing that’s not actually real, and once you try to make a concrete, it’s like, “Oh, there’s actually a lot here to still think through and work through.” Perhaps actually, we could whiteboard on this again and maybe burst through another kind of wall, or I just need to keep slogging through it and returning back to it every so often, and incrementally building it out.
Rob: Yeah, that makes sense. It sounds like you hit—not a robot necessarily—but it’s a bit harder, a bit more challenging than you thought it would be. Mockups are often like that. You’re almost trying to invent something new and you have to thread a needle because you can’t be Slack but you can’t be email.
Derrick: Most of the difficulty that I’m having is centering around this inbox in Level. That’s one of the core pieces of the product is–it’s something that’s really missing from Slack–is that I want to have one place where I can come to and quickly see, in priority order, all the things that need my attention. Then I can step away for six hours, go into deep focus mode, come back, and feel confident that everything I need to see with relative urgency is it’s all laid out for me just as I want it.
Once you start kind of exploring, “Well, what happens when there’s 100 messages posted in this group and 50 in this group? How does the inbox mutate over times, that things don’t become overwhelming, and it doesn’t devolve into kind of the email inbox mess that so many people experience? How can I actually make good on the promise that I am threading the needle well between email and chat?” Once I overcome this, it’s going to be, hopefully, something really good and is really going to resonate with people. But until then, I don’t feel like I can just start showing these theoretical mockups where I just kind of hand wavy say, “Oh, it’ll be always manageable for you.” I want to give some proof that I’m actually on to something–some framework or some methodology for categorizing and organizing these messages.
Rob: Right. Because the challenge when you’re building something new is to validate your most risky hypothesis–that the ones that are most likely to fail where the risk is. Typically, it’s not the code itself unless you’re going to build—“I’m going to build an AI engine to predict stocks.” Well, it’s like, “Alright, that’s your first thing. Can you even do that?” But here, you know that you can write the code to make messages go in and out of a queue and come out of the things. There’s two risks left that I see. One is, can you design a UI that is novel enough, and does thread that needle between the two, and is 3X better or 5X better than the other experience for a certain group of people. Then the last risk will be, will people pay for it?
You validated that somewhat through building your email list and having this in-person conversations. I’m guessing once you have mockups or at some point you’re probably asked for whether it’s verbal commitments, or you may take money upfront, and I don’t think you’ve decided on when you’ll do that. That is a big issue—building the mockups and figuring out how is this flow going to work, and is it as novel enough and iterating on it until it is.
Derrick: I think this is arguably one of the most important pieces to work out because without this, the whole promise falls down. It’s one thing to just introduce threads for example. Slack has kind of arguably, poorly implemented threads. If I just implemented something that was just like, “Oh, everything’s a thread. That’s great but that still doesn’t solve the problem of not being a complete catastrophe when you step away from it for a long time.” It’s one of the critical moments, I would say.
Rob: Indeed. I want to switch up a little bit. We’ve talked a lot about the specifics of Level and your process of validating it, and getting the design going. I’m curious, this is in essence, kind of the third app or third startup really that you’re launching. I know that you launched a couple that came and went pretty quickly. But then, you had obviously, Drip with me. You did Codetree, codetree.com which is kind of project management that sits on top and you did that on the side. You sold that while we were, actually, right around the time that we sold Drip, you sold that if I recall.
Derrick: I sold that, we sold Drip, and I sold my house when we moved. I had three big sales.
Rob: That was crazy.
Derrick: Talk about massive liquidation.
Rob: I know. This really is, for all intents, your third act here. I’m curious if you think it’s easier this time around, is it harder, is there more pressure. Talk me through the emotional side or the mental side of where you’re at with it.
Derrick: I think it’s unique in that, with Drip, I started out as a contractor, and so I was gathering a paycheck. Then I went full time on it and then we had HitTail bankrolling our efforts a bit. It was a self-funded endeavor that was throwing off enough money for a least a decent paycheck so that I could live. Codetree was a side thing–that was nights and weekends. I was basically sacrificing my free time, but in exchange, it wasn’t really costing me actual money. Now, this is the first time that I’m really, as an adult, going off and saying like, “I’m not going to earn any salary or revenue for the whole time that I’m building this thing, or at least until I launch it.”
I think that that introduces, in itself, a bit of pressure that I’m trying to just like always mentally overcome that. Obviously, selling Drip and Codetree helped give me a little bit of runway so that I can afford to do this. That’s arguably the whole reason why we do this is so that we can afford to work on the things we want to work on. I’ve had to do some things like, set aside my living expenses for the next year, and figure out loosely what my budget’s going to look like, and then make transfers from this account to my checking account, and just say like, “I’m paying myself for the next year. I’m not allowed to think about money or stress about it.” It’s a work in progress but working on trying to do things like that to keep myself sane and not get too stressed out.
Rob: That makes sense. I find it funny you’re like, “This isn’t the first time as an adult,” because you were an adult all the time but now you’re married. You have real expenses. You live in a city where the cost of living is not super high. But Minneapolis is definitely akin to a California city that’s not L.A. or San Francisco. It was similar to Fresno which is not super cheap. It’s not like you’re going to live on $2,000 a month here. Depending on how you live and where you live, it’s a non-trivial sum.
I’m glad you did that. I know that you were stressed early on about burning some cash. As you said, the two exits you have helped bolster that, but I think your wife also distinctly gave you permission. She’s like, “You need to do this. You earned this.” Is that the phrasing? It was something like that. Like, “That’s what you did these other ones.”
Derrick: Exactly. This is not the time now to say, “Oh, I don’t know. Maybe I should keep a job and do this nights and weekends.” She’s like, “No, no. This is the whole reason why you sell companies.” I think she has a lot of wisdom in that.
Rob: Yeah, I would agree. Cool sir. Thanks for joining me today while Mike is out of town filling in our 399th episode.
Derrick: Oh my gosh. You’re one off from 400.
Rob: Isn’t that crazy? We’re going to figure something out to do that’s like a big bang, not just Mike and I talking about five ways to wrap or something. Can we do something different? We were the worst at that. We’ve looked back and I think 300 we may have just done a normal episode, that’s kind of a shame.
Derrick: Yeah, you got to take these milestones and squeeze some juice out of them.
Rob: Yup, yup, celebrate them a bit. Cool sir. Well, if folks want to keep up with you, they can hit level.app yeah and then derrickreimer.com. That’s where you blog now and again about your experience. You’re building Level for developers out there, you’re building it in Elixir and Phoenix.
Derrick: Elixir Phoenix is the web, framework web, kind of the rails of Elixir.
Rob: GraphQL…
Derrick: GraphQL is the API layer, and then Elm on the frontend, so the Elm translates into javascript. It’s a very shiny new tech stack for me. But I’m having a lot of fun building in it.
Rob: Well, I think for most people.
Derrick: Yeah, for most people. It’s a fairly proven technology but still on the newer side. I feel it’s really exciting. It’s predominantly centered around functional programming languages. Elixir and Elm, they’re very functional. It’s a bit different from what I’ve been doing. I’ve been writing Ruby for the past eight years, but yeah, I’m having a lot of fun for it. I’m hoping that the Level codebase can be a good example of like a full-scale SaaS application that’s kind of out there in the world for people to reference.
Rob: Yeah. I obviously don’t know any of the languages you’re using but you have such a good way of organizing our codebases, and your Read Me was super clean. I was like, “Ha, if I had a few extra hours this week, I would just run these commands and try to see if I get this thing right.” It was kind of fun. It was good to see it and then get out there. Cool. Well, thanks again for coming on the show.
Derrick: Yeah, thanks for having me.
Rob: I think that wraps us up for today. If you have a question for us, call our voicemail number at 888-801-9690, email us at questions@startupsfortherestofus.com. Our theme music is an excerpt from We’re Outta Control by MoOt, it’s used under Creative Commons. Subscribe to us in iTunes by searching for Startups. Visit startupsfortherestofus.com for a full transcript of each episode. Thanks for listening. We’ll see you next time.