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You're listening to Startups for the Rest of Us. I'm your host, Rob Walling. In this episode, I talk with Jason Cohen. You might know him online as a smart bear. He's been blogging for almost 20 years at asmartbear.com. He has started two unicorns including WP Engine of which I was an angel investor. It was my first ever angel investment back in 2011. And Jason has just been a longtime supporter of MicroConf and now Tiny Seed. He has given several talks at MicroConf, including one that is widely considered to be the best talk ever given at a MicroConf. And I think it's the best talk ever about bootstrapping startups. And we talk about that in this episode. I actually struggled to title this episode because we talked about so many topics including mistakes founders make in the early days. We wrap it up with a discussion about AI and where Jason feels like the opportunity would be if he was starting over today. But in the end, we cover some meaty topics. And Jason is just so thoughtful and deliberate in his thinking and so clear in his thinking. I have infinite respect for him and it was a pleasure to have him on the show today. Jason's actually going to be speaking at MicroConf US in Portland in just a couple months. Tickets are selling fast and we will sell this event out. microconf.com/us if you're interested. And the promo code you'll want to use is rob50 for $50 off. And with that, let's dive into our conversation.
Jason Cohen, welcome to the show.
Hey, thanks for having me. It's always great to talk.
It feels criminal that this is your first appearance on Startups for the Rest of Us.
I know. I don't understand. Maybe because I was busy the last 15 years. I don't know.
So, yeah. What have you been up to, man? Growing another unicorn. No, it really I mean, you and I talk often enough that I just And you've spoken at MicroConf so many times that it just feels like you're a staple in the ecosystem. And when producer Ron and I were talking, it was like, how has Jason never been on the show? Like, that's not great.
Well, I mean, you were an angel investor in WP Engine. So, you know, you're probably happy that I stayed focused on that instead of doing podcasts.
Heck yes, man. That bought our house, paid cash for our house. It was great. So, a lot of folks will be familiar with you as the founder of WP Engine as well as Smart Bear, which was the software company before that. Both are unicorns at this point and you've been a longtime blogger at asmartbear.com. Hundreds of essays if I were to guess, but what did I miss in that intro? Like how else would you like folks to know who you are and what you do?
I think that's good. That's my best work.
Well, that's your best work in the rearview mirror. I want to call people's attention to Hidden Multipliers at hiddenmultipliers.com. It's your first book that you have for pre-order right now.
That's right. Yeah. So, I'm not here to promote it. Although, maybe we can do another one where I am there to promote it. I don't know. But yes, I've been writing for 18 years like you said. But one of the things I felt was I've been writing on all these topics, but there's no central idea. There's no central framework. It's just a bunch of random stuff. And so when things would come up in conversation or online or whatever, and I'll say, 'Oh yeah, I wrote about that over here.' It was so scattered. And people would say things like, 'Do you have just like stuff about marketing?' And I'm thinking, 'Yeah, kind of scattered over a million things.' You know, this is not very accessible. So the purpose of the book wasn't just to take every idea and make it organized, but rather I thought, I wonder if I do have any central concepts. Do I have a philosophy? I don't even know. And so for maybe a year, I just thought like I don't know. I don't know that if I have one. And so I didn't want to just write an anthology. But then there was this common thread I found in at least a lot of the things that I think which is that there are these small things that make an inordinate difference in companies and of course every company's different and all that. So all those normal things apply but there are some things which are systematic and mechanical about how companies work or how people buy things or how human nature is, how teams work, or even about like A/B testing and the math behind that like certain things which are true because they're built into how it normally works and that's why these things where a small change can make a big difference that's why that's so common because it's based in some systematic fact about the world or how things work. And then another criteria I found that was interesting is of course if you can raise money or apply a lot of new money and teams to something there's many possibilities and that's good. Maybe you should do that. But most of the time we have a team, we have a budget and we need to do things within that team and that budget. So if the feeling is man I'm not growing as fast as I want or I'm not as profitable as I want or I'm not getting this or that goal that I want. Usually the answer is not oh I gotta go raise a bunch of money right like almost always even if you have raised money that's usually not the answer right usually it's like but we have people doing stuff even if it's one person and surely we could be doing something a little bit better so this was this extra criteria that I thought was interesting to add on top of this small things make big effects it's systematic so it's usually true you can pretty much rely on it and this idea of I've got to do it with my current team and budget so it has to be doing something differently but not some kind of big investment or something like this. And I found that there were these things which fell into this category. So that's how I defined this idea of a hidden multiplier. Multiplier being this notion. And then hidden is another funny word. Sometimes these things are hidden just because you didn't know it. Sometimes you did know it, but it's on a to-do list with 10 things and you didn't realize how important it was. So it's hidden in that sense. I once had a great strategist tell me a lot of times what's wrong with a strategy is not that we didn't know something, it's that we didn't realize how important that thing was. So these can be like that or maybe you did know it but you didn't know what to do or you were scared to do something about it. So without an explanation of what do I do? It just sort of hangs out there. And the form I see that in is people will say I already knew that and then you look at their actions and you're like well you're not acting like you know that. So it's like effectively you don't know that right? And so that's what I mean by hidden. This kind of somehow or another you're not taking advantage of it. So that's what this book is like 10 of these hidden multipliers, one per chapter, just going in great depth of course about what is it, motivating it, proving it with examples, and then saying of course what to do.
And this is I was surprised to hear that this is majority new material that you obviously use some concepts and ideas from your blog, but yeah, you've been hammered on this original work for what, a year now?
Yeah. I didn't want it to just be an anthology or a rehash of the blog, but obviously there's some stuff in there that is in the blog because these are I've had certain ideas in the last 18 years. Some of them are good and so you know that's only natural. But yeah, I didn't want it to just be a rehash.
There are a lot of founders out there that are successful and they never but they aren't public about their thought process or their mental frameworks and maybe they don't have any. Maybe they just figured out in its instinct. Maybe they get lucky, whatever. Then there are folks that are successful and they are public about what made them successful and then there's two camps there. I'll see someone do a talk and they'll say, 'This is why I was successful' and you're like, 'No, it's not.' Like you're full of either you're lying to yourself or you're lying to me, you know, like you're delusional. But then there is this small small camp of folks and this is all arbitrary designation based on my opinion or your opinion who have found success and think critically about what they've done and try to extract higher level learnings that go beyond just their end of one or two and that tend to when you hear what they say Paul Graham's one of these guys right Joel Spolski yourself when you hear what they say you're like yeah no that generally tracks that's a really unique insight that sounds obvious in retrospect but no one has said it in that way before okay so I totally put you in that bucket and it's very rare. There are not thousands of these people in the world in the startup space. You know, maybe there are hundreds. I don't know if we were to quantify it. So, I guess I'm just wondering how you got there. Like, have you always been a critical thinker analyzing your own behavior and what's going on around you and trying to framework things or did this kind of evolve for you as you were starting companies? You're like, 'Oh, I'm learning a thing and I should just share that with the world on this blog that you started in what 2007 or 8,' right?
For me, writing is thinking and I have this drive to teach. Both my parents were teachers. I think it's literally in the DNA. And of course, we all know that if you want to learn something the best, you teach it. On the other hand, can you teach something you've never done? A lot of people do. This just not me, right? So, I think that's another reason people like it is at least this came from experience. And so what generally happens is I'll have a thought either because I observe it in some other company, I observe it in our own company, we've learned something, something went wrong, something went right. And that'll give me an idea for a thing. Like maybe it's a framework or a concept or a story or something. But in writing it out, I often find, wait, maybe that's not right or maybe I don't even agree with myself and I haven't even published it yet, you know, and or maybe I do like it and I'm just even more excited about it because oh look, I'm finding other examples. I don't know. Like I could get more excited. So, I mean, I have hundreds of things in draft that I'll never write because I don't actually believe it or I haven't figured it out well enough. I haven't sorted it out well enough for myself to put it out there. So, a lot of these things are, oh, it seemed to be right. We wrote it down, then we tried it at WP Engine, say, especially if it's a framework. We probably I mean, I can name them where we did like we tried it and then we iterated on that and we tried it again with a different team and then we iterated. And so, the result when it comes out, it's like, wow, this seems really thought out. I was like, 'Yeah, that's because we actually did this and iterated on it and I tried to explain it as best as I could and if you write for a long time, maybe you're better at writing, you know, hopefully, right? So, okay, now I can do that.' So, yeah, often that's where that comes from. Having said that, I don't think the goal, at least not for me, is to convince everybody that I'm right. It's equally valuable if someone reads an article of mine and says, 'I don't believe this is total crap. I don't believe this at all. I believe the opposite.' No, it's this. You know that's perfect because what's happened is you've gained greater clarity on what you do believe what is your philosophy or your values or how you operate or what's important or how you you know something important you've now gotten greater clarity on because I was a foil that was not what you thought and that led you to what you do think in greater relief and that will make you better make you stronger and clearer in whatever direction you're going. So to me, the goal is that this kind of like, ooh, now I think X or now I'm clear on why. That's the goal, which is not the same thing as agreeing, right? So that's fun. Obviously, there's a constructive and not constructive way for people to say that online. You get both. But I love it when people have the opposite view. Also, we all know that for every piece of advice or observation in business, the opposite is true of some companies that are successful. And both it and its opposite are true of companies that fail. We know that all four of those are populated with companies populated with examples. And so once again, there's no way I'm going to think that that means I'm right all the time. But again, if someone can get clarity, that's really useful. So, how do you do that? You have to say something useful, something real, something specific, hopefully in a way that's relatively well put so that it's enjoyable to read. And by doing that, you know, hopefully someone will get something out of it.
I'm curious, you know, a lot of the stuff that you write about has to come from firsthand experience because you've started four companies, two are unicorns, but you're also an angel investor and an advisor. Were you kind of a founding member of Capital Factory in Austin, am I remembering that correctly? So you've been exposed to dozens if not hundreds of startups. Do you feel like more of your knowledge and information that you share comes from your firsthand experience or from the experience with other companies advising on the internet or otherwise?
I would say when it comes to specific things like this decision framework or this prioritization or this workshop that's coming from WP Engine that's coming because we tried things and this seemed to be something that worked for us or for some teams and so that seemed worth sharing. When it comes to more strategic or high-level long-reaching things some of that's my own experience but a lot of that is like oh man I've seen this like 20 times which obviously doesn't mean I saw it in my own one to four examples. So the 30th time you hear someone pitch something and you go, 'Oh my god,' you know that's coming from a breadth. So I would say where personal psychological stuff obviously starts from myself, but a lot of that is in talking to other founders where there's certain kinds of things where you know 80% of the time that I share, oh yeah, I felt like this or I felt like that and you know almost all the time the other person's like, 'Oh my god, I thought it was just me or I can't believe you're admitting that.' And that again is some kind of not universal but pretty useful good truth there that's coming from talking to other people right that's the only validation that it's not just me.
So you have what I believe is widely agreed to be the best MicroConf talk that's ever been given. And I know I make you blush when I say this but that you just you mic dropped with this talk back in 201 I don't remember if it was 13 or 14 but it's called Designing the Ideal Bootstrap Business. And I was in the room when you gave that talk and I was just I was holding my head. I was like, 'Oh, like as you were giving it and then you got done and I turned to whoever was next to me and I said, I don't think I'll ever give a talk that good. That's the best talk I've ever seen.' It was huge. And I'm serious. Like and it has lived on and I still believe I was trying to pull it up on YouTube right now, but I believe it might be the most popular talk on our entire what used to be the MicroConf channel has now been renamed to Rob Walling. But 510,000 views.
That's awesome. You know what? Here's something funny about that which should be inspiring to you or you know to the listener and to myself when I'm thinking about things like my own book, which is I thought that that talk was haphazard. It didn't have a good arc. It didn't have like a narrative arc. I felt like I did have a good personal emotional close to it, but I didn't feel like it came full circle. I felt like it was a shotgun of different ideas rather than a conceptual framework, a tree with branches. Instead, it was just like stuff everywhere. So, I felt when I made it, I am confident that the individual ideas here are useful. So, I think this talk will be useful. I just don't think it'll be good in I mean, literary is too strong a word, but good in these other kind of structural ways like a Seth Godin talk is, for example. So I was like, 'Oh well, hopefully being useful is good enough, especially for this audience, which I think it is.' And yet, as you say, people loved it anyway. And so one of the lessons for me about that art side of things, going with what you just feel, what you are passionate about, and the things you're excited about, that's actually good. That's what people are here for. Probably every single idea in that talk you can read a blog post about somewhere. So that's not really about everything's a brand new invention. Although I did there were certain things in there that I at least at the time I hadn't seen elsewhere. But they probably were elsewhere. I just hadn't seen it, you know, but it was more the exposition. So like when I think about my book, there's certain things like maybe it's too long. Maybe I go into too much detail about certain things. I don't write like Hemingway. I use long sentences and semicolons and em dashes. I don't have tiny little sentences and I don't write for a fifth grader and all that stuff. So is that bad? because quote unquote that's what a business book should be unquote right well I don't and so I think on that artistic side of things I'm comfortable saying well I'm going to go with what I am and that talk is a good example of that for me.
Yeah and it's inspired a lot of folks I mean I hear people mentioning it on podcasts and on Twitter to this day so folks haven't watched that it's on YouTube and they should go find it but I kind of want to contrast that or attach that to an essay you wrote called Excuse Me Is There a Problem because in your talk about Designing the Ideal Bootstrap Business. There's some filters for kind of finding an idea and finding the right type of business for bootstrappers, right? But if someone has a business that checks all those boxes, it's recurring revenue, it's a good market, there's maybe no enterprise sales, if folks are solo in your essay that excuse me, is there a problem? You show that maybe that's still not good enough.
