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Jason Cohen
Founder & Chief Innovation Officer, WP Engine

69: Sound, Actionable Advice with Jason Cohen

📅 Jun 06, 2026 The Next Track 70 MIN 1 VIEWS 206 SEGMENTS · 2 SPEAKERS
Derrick is away, so Ben welcomes Jason Cohen, CTO of WP Engine and four-time entrepreneur. Jason knows a thing or two about startups and mentoring them to achieve profitability and growth. Jason is a straight talker and tells it like it is to get to solutions sooner. He encourages bootstrap founders to find an advisor who aligns with their goals. You need to know how to take advice and use advice that is right for you and your business. Even if you get great advice, think for yourself! Today’s Topics Include: • Advice is not enough; luck, execution, and other pieces...

What Jason Cohen said

Written from the verified transcript and checked against it. Every figure links to the moment it was said.

Jason Cohen, founder and CTO of WP Engine, discussed the nature of good advice, arguing that most advice is context-dependent and often reflects the advisor's own goals, so it must be tailored to the advisee's situation. He emphasized the importance of constraints and filters in decision-making, and the value of being a 'learning machine' that can pivot quickly. Cohen advised the host on Tuple, a remote pair programming tool, urging him to consider selling an imperfect product now, leveraging the developer audience's understanding of technical challenges, and exploring viral business models. He also shared insights on selling to developers, noting the difficulty of reaching budget holders, and recommended a bottom-up sales approach. Cohen concluded by plugging WP Engine and his blog, asmartbear.com.

Key takeaways

  1. Constraints and filters, even arbitrary ones, are valuable because they reduce options and help you make decisions and get to work.
  2. For Tuple, Cohen suggested selling the product now, even if imperfect, because customers may value the transformation over latency.
  3. A viral business model, where the nth person can invite the n+1th for free, could be key to Tuple's success.
  4. Open sourcing parts of Tuple could engage the developer community, but it's a lot of work and may not be worth it at this stage.

Numbers and commitments

FigureWhat it refers toTypeAt
615 WP Engine employee count metric 0:47
3,000 People on Tuple's email list metric 36:09
$8,000 Pre-sold revenue for Tuple's paid alpha metric 34:27
5K of MRR per month Threshold for a paid marketing channel to be considered working guidance 31:08
10 or even 100 times Potential revenue increase per customer in larger organizations guidance 56:07
13 years Length of time writing on asmartbear.com metric 1:10:38

Chapters

  1. 0:00Advice and its context
  2. 13:02Learning machine and agility
  3. 15:08Embracing humanity and smallness
  4. 19:06Filters and constraints in decisions
  5. 24:53The trap of doing what you love
  6. 34:18Health check on Tuple
  7. 38:50Selling an imperfect product
  8. 45:51Engaging the developer audience
  9. 57:48Viral business models for dev tools
  10. 1:09:10Closing remarks and plugs

Questions asked in this interview

12
  1. 2:38Have you seen Paul Graham give advice to startups?
  2. 4:44And did you come to that conclusion because you had bad advice in the past that wasn't tailored for you?
  3. 9:05Do you still advise people at Capital Factory?
  4. 9:31Does this position, your philosophy on advice come from trying to advise other people on the regular?
  5. 19:06Do you have any like favorite filters that you apply right now these days or in the past?
  6. 30:35Is it like everything else where you just learn it by doing and try to figure it out?
  7. 35:49So, is it like desktop sharing but you're super smart about diffs, sending diffs and compressing that and I don't know, things?
  8. 36:49Do you understand the transformation that is?
  9. 41:48Like am I crazy to not keep doing that?
  10. 54:55Anything else jump out to you or should we just wrap it?
  11. 57:48And then your friends can't use it with somebody else. And does that make sense?
  12. 1:06:06Is that the play with the viral situation?
Host 0:00 ↗
Hey everybody. Normally I would be starting off this podcast by welcoming Derrick, but instead I have a guest. Derrick has left me all alone to fly solo, but fortunately I have a co-pilot today and it is Mr. Jason Cohen. Hey Jason.
Jason Cohen 0:13 ↗
Thanks for having me. It's good to be here. I didn't realize I had to fly though. I guess I need to put the booze down now.
Host 0:20 ↗
Yeah, you can't, you people can't see this, but Jason is chugging from a large bottle of bourbon regularly.
Jason Cohen 0:26 ↗
It was a large bottle of bourbon.
Host 0:27 ↗
Yeah, exactly. Now it's just a bottle. So in just in case you have not heard of Jason, he is a four-time entrepreneur. He's done bootstrapping, he's done fundraising. Currently he is the CTO of WP Engine, which you started off bootstrapping and then raised money for and now is enormous, like 700 employees or something.
Jason Cohen 0:47 ↗
Only 615.
Host 0:50 ↗
Okay. So a relatively small enterprise.
Jason Cohen 0:54 ↗
Well, if you establish the baseline at 700, then it's small.
Host 0:58 ↗
That's true, yes, comparatively. So we'll go back and edit this.
Jason Cohen 1:01 ↗
Logic, you know, you have to set the frame up and then it can feel like it's expensive or not.
Host 1:08 ↗
I can't, anchoring is such a powerful, ridiculous brain hack. I can't even believe it's like legal. Like you shouldn't be able to do it.
Jason Cohen 1:13 ↗
Well, fortunately you know it. Although even when you know it, it's still difficult to ignore it.
Host 1:19 ↗
That's the thing, yeah. Like if only knowing your cognitive biases meant they didn't work anymore.
Jason Cohen 1:24 ↗
Right.
Host 1:26 ↗
Yeah, that'd be great. So I saw you on Justin's podcast and live stream extravaganza and I really liked what you were saying. I appreciate your sort of semi-contrarian, no BS, tell it like it is attitude, I guess. And also I didn't realize that you did podcasts. So I was like, all right, I got to get him over here.
Jason Cohen 1:45 ↗
Well, I don't know if I would say it's contrarian. That's a joke.
Host 1:48 ↗
Um yeah, that's fair. Yeah, not so much contrarian, but...
Jason Cohen 1:51 ↗
By saying it's not semi-contrarian. Okay, never mind.
Host 1:53 ↗
Yeah, right. You backed yourself into a tautology, anti-tautology. I appreciate anyone that will talk straight with people. And I got the sense that like Justin was kind of hoping you would say, 'Yeah, you can work on this business about 10 hours a week and that'll be fine. Like, don't worry about it too much.' And you were like, 'Nope. No way. Sorry.'
Jason Cohen 2:12 ↗
Right. What's nice about being straight, even if it kind of hurts, is that you can get right to the solutions. Like, just stop beating around the bush about what's going on or what's wrong and just, nobody's fault. Like, just stop it. Let's just call it what it is and then let's spend all the time thinking about, 'But what could we do? What are some options? Can we weigh those? What could I try?' Like, let's just get to that part and stop arguing about whether you know, how that works. Let's just get to it.
Host 2:38 ↗
Have you seen Paul Graham give advice to startups?
Jason Cohen 2:41 ↗
Um I'm not in person. Of course, I think many of us have seen the advice in the form of blog posts and tweets. I think it's a great example of there's a common phrase people give advice to themselves. Meaning, but what I would sort of amend a little and say, people have a certain thing in mind when they give advice and it's often themselves because we're all egotistical and of course, I'm not an exception. But there's certain goals you have in mind or a certain context. Like for him, it's you got to change the world and make something huge and so that's the context. And so the advice is in that context. And so is that advice still accurate if you're a bootstrapper and you don't want to be the next Facebook? Is that still the... And you don't want to be a Y Combinator company, which of course is what the advice is tuned for, Y Combinator style companies. So if that's not you, then is the advice right? And the answer is sometimes because some advice is more universal or maybe, you know, there's other reasons why it's right for you. And maybe it's not. So the closer you can get to an advisor who either naturally is aligned with you because they have the same kinds of goals and attitudes and world views and life tradeoffs and other things as you. And so even though they're talking about themselves that it works, that's one way. Or someone who's conscientious and sort of aware enough to ask lots and lots of questions first to try to understand those very same topics so that hopefully the advice is tuned.
Host 4:01 ↗
So, the reason I brought him up in particular is because I feel like he has a like 0% buffer before he's like, 'Stop talking. I have another question for you.' kind of thing. Like the questions are great and his suggestions, at least for the type of companies he advises, I think are great. It's like if you had to condense everything down into 10 minutes, he's just dispensing with all of the sort of pleasantries, subtleties, all that normal social stuff.
Jason Cohen 4:24 ↗
That's good. They're boring anyway.
Host 4:27 ↗
Yeah. And especially if you're advising like 100 companies or whatever they were doing. I have to imagine you really need to do that. You touched on this thing that I wanted to ask you about, which is advice that's any good starts with like an hour of the advisor asking you questions about what your goals are.
Jason Cohen 4:43 ↗
Yeah.
Host 4:44 ↗
And did you come to that conclusion because you had bad advice in the past that wasn't tailored for you?
Jason Cohen 4:50 ↗
I'm not sure how I came to that conclusion, but I think it's more as I give advice to others, I've realized that I'm speaking from my own experience and all those other things I just mentioned. I don't have to repeat them. And that's not necessarily right for people. I also, I don't know, maybe it's a decade ago had a presentation, you know, one of these go-to conferences presentation on this topic of advice and how to know if the advice is good, how to take advice. And I started with this premise, which I think is still true, which is if you find any advice whatsoever, I can find you someone else who's very smart and successful who will tell you to do the opposite. No matter what. Anything. The thing about needs, you know, being able to do it on the side. DHH says you can do it 10 hours on the side, even though that's not actually what they do with 37signals, it turns out. But anyway, Zell says so. You can find it. And he's smart and very successful, so what the hell? And then you can find many people saying, 'No, you have to work very hard.' Easy to find both sides. You could find people that say, 'You have to be good at social media like Twitter.' And there are other people that say, 'Look, I built a million, a hundred million dollar bootstrap business without ever using social media.' It's easy to find all those. So, given that, what do you then do? Because that means none of the advice is necessarily the make or break. And probably it's not true either that like, 'Well, that's because advice is just good and bad and you can't tell.' Like probably all that advice is good for somebody and all of it is bad for somebody, probably. So, then it's not really about the advice, is it? It's really about like, 'Okay, so how do I know what's right for me?' And so that's how I eventually got to this notion of it has to be tuned to your context, goals, etc. All those things we just said would go into more detail on those things, I guess. And so then the advice giver is usually not introspective enough or conscientious enough to know that. Therefore, they're just giving advice. So, therefore that's not helpful. So, the conscientious person knows this and therefore asks a bunch of questions, 'What are you trying to achieve in what time frame? Do you care about money more than being at home? Do you care about changing the world and if so, what does that even mean to you?' Because it means very different things to different people, as it should. Right? And I mean there's maybe 20 questions, big questions like that easily that you could ask to really understand what a person's trying to do and what their strengths are and what they should avoid and help they may need or things they should ignore. Then you start getting into, 'Okay, here are some real options that address the situation you're in and are consistent with things you're actually trying to do.' And now we're into the realm of good advice or at least the chance of good advice.
Host 7:26 ↗
Right. Yeah, it might still be bad.
Jason Cohen 7:29 ↗
Yeah, well who knows? You can't run life twice, right? You can only run it once. Which is all just to say, don't obsess about the damn advice. Try to think for yourselves. Try to limit it to a couple of main things that you're going to decide based on, a couple of main ideas. And then move on because even if you have great advice from a really good advisor, it's still not, it still maybe, who knows.
Host 7:49 ↗
Totally.
Jason Cohen 7:50 ↗
The exception is when it's very black and white stuff such as, 'Hey, what's the employment law in Texas about X?' Okay, now that there's an answer. And so that's good. You can get an advisor that gives you the answer and that's a good thing. And if you learn that, then you have some experience you can bring forward. Good. So that I mean there is such a thing as stuff that's just correct. But it's very, it's few and far between and usually not the strategic important stuff.
Host 8:14 ↗
I like this actually point here of even if the advice were perfect for you, like amazing advice period and perfect for you, even then that's not really enough. Like all you know is like a blueprint at this point, but everything after this is execution, which is the hard part.
Jason Cohen 8:29 ↗
And random and luck and stuff like that.
Host 8:32 ↗
Yeah.
Jason Cohen 8:32 ↗
Maybe you say, 'Look, there's these three options.' And you weigh it all and option A is the best way to reduce risk and increase upside. And maybe let's just say for the sake of argument you could prove it, even though you can't. Then you prove it. Right, but there's still a chance for upside and there's a chance for risk. And so even if it was the best bet, it doesn't mean it comes up right. You know, the best poker players clearly have skill. That's why they're always at the last table because skill. But they don't always win because luck.
Host 9:01 ↗
Right? Like...
Jason Cohen 9:03 ↗
So the same thing except we have less skill and there's more luck.
Host 9:05 ↗
Do you still advise people at Capital Factory?
Jason Cohen 9:07 ↗
Only like one or two because I don't have any time and I certainly haven't done any new investments in a long time because WP Engine has taken all the time and I don't want to dilute time and I am clear that I want to do WP Engine and I want to be at home. And since I'm clear on those two things, I don't do other stuff. I used to have other hobbies and I used to mess with companies at Capital Factory more and now I don't because I'm clear on that.
Host 9:31 ↗
Does this position, your philosophy on advice come from trying to advise other people on the regular?
Jason Cohen 9:36 ↗
Yes, especially in the early days of Capital Factory, which is sort of like Austin's version of what started out as Austin's version of Y Combinator when both were small, when it was like a class of five or 10 for a summer. That's what we did, too. Now, Capital Factory is hundreds of companies. Some are co-working, some are inside of a funding program. There's a whole bunch of stuff going on with it. But early on, there were many startups that came through, some of which were in a program, so they were, you know, kind of intense advisory and investment. And others sort of just there, and so by observation, you can see some things. And just by talking to a lot of founders, you sort of get a certain sense of different kinds of personalities and what things and you kind of see what things work. None of that's very scientific, obviously, but you do get a gut feel of stuff, and that's where this comes from. I don't have data that shows you should ask the following questions, right? This is just experience in trying to formulate something.
Host 10:28 ↗
Right. And did you experience like finding your advice kind of out of joint with the people that you were talking to that made you realize like, 'Oh, I'm not thinking enough about the context of these people I'm advising.'
Jason Cohen 10:38 ↗
Yeah, so what would happen is they would say, 'Well, here's our situation.' And let's say, especially in the context of an incubator, you're usually talking about raising money, because that's what incubators sort of gear you to, most of them, not all. A lot of times, the idea wasn't very big or the traction wasn't very good. The story wasn't really one that would excite an investor. And so, I would say that. I'd say, 'Look, you know, you're saying these things and an investor's turned off when you say that because, you know, whatever the reason is.' You emphasize the team, but this team is not very investable because you don't have previous experience. Now, if you were just bootstrapping, who cares? Don't even have a team slide. In fact, don't have a slide. You get back to work. What are you doing? Right? The very fact that you're pitching means you're pitching to an investor. Like, I don't know why else you'd pitch. And then, this team slide is bad because these are not the qualities that an investor is looking for. But, there are different qualities we can emphasize that are what the investor's looking for. And you could be more honest going back to what you just said about appreciating being honest and straightforward. Just be honest and say, 'Look, this isn't the normal team that you see.' So, then how would you overcome that with an investor? If the team isn't normally investable because you don't have prior successes, blah blah blah, what would you do? Well, you could say, 'Well, we could prove that we are a learning machine. We could prove that every month we learn stuff, change it, and the business gets materially better. And we never stop doing that.' In other words, we could overcome the fact that we don't have previous success to point out by saying, 'We are such an engine for building a great company that we know how to do this.' And then you just really emphasize it. Have proof points. Show, 'Look, we saw this, so we changed that, and then this was the result. We saw this other thing, we changed this, and this result was negative. So, we did this, and then it was positive.' And then you tell these stories, and no one cares what your bio is because who cares? You're able to do this, and that's obvious. So, let's deemphasize the team and emphasize these other things. Now, all this though is talking to someone in the sense that they want to go raise money. But then sometimes at the end of all that they go, 'But you know, honestly, I don't care about impressing that person.' I'm like, 'Well, what? You don't?' And they're like, 'No.' 'Why not?' 'Because I don't want to raise money. I don't want anyone telling me what to do.' 'Well, then why are you in a pitch practice?' 'Oh, they just said it would be good practice.' But see, so the whole thing is like, 'Wait a minute, the goals were different. So, none of this advice was any good.'
Host 12:57 ↗
Yeah. You just said something there I liked a lot, which is you characterized a company as a learning machine.
Jason Cohen 13:02 ↗
Mhm.
Host 13:02 ↗
I dig that a lot.
Jason Cohen 13:04 ↗
You're constantly failing. You're constantly not doing the right thing, and you have no resources at all. You don't have brand recognition, you don't have money, you don't have a big customer base to motivate you. Your social media has four followers. Like, you don't have enough time. You have nothing. All right? So, one of the few things that you have when you're little is you can change directions really fast. Because you don't have any of those things like customers, you can make changes. You can change the product or the brand or how you sell or the pricing or what features are there or delete features. You have the ability to move really fast. So, you should do that. Like you should use the advantage that you have that your bigger competitors cannot do. It's one of the few things you can do. Another one is being really human. Big companies, every time you call them you get a different person. It's the nature of it. You're not when you're little. You should use that. You should be on the home page and you should be on social and so that people have a personal connection. That doesn't scale. That's okay. Who cares? A, maybe you never want to scale, so that's fine. Or B, you do, but like first you have to get to the point where scaling is a problem. So, move in ways that a big company cannot do. So, these are some of the few advantages you have. So, to me like you must take advantage of them since you have so few advantages when small. You got it. And so, one of them is this agility that you just mentioned, which is to learn fast and react to it. A big company can't, even if a big company learns fast, it can't react fast. And also it probably doesn't learn fast. And so, be a learning machine that's always getting better. And that is a good recipe for since most of what you're doing isn't quite right yet by definition.
Host 14:43 ↗
You touched on something that stands out to me a lot, which is embracing your humanity and your smallness. And I've seen friends running like one-person businesses that talk about themselves as a 'we' in their like marketing copy. And I know why you would do that. I understand the feeling of smallness or insignificance I think that would have caused you to do that. But I think we're on the same page that this just, you're abandoning something actually that's useful.
Jason Cohen 15:08 ↗
So, the issue with that and I've done it too. I did it at Smart Beer for sure. So, it's not like I'm not guilty of these things. All right. The problem is that you cannot in fact act like a bigger company. You will not deliver like a larger company will deliver. And that will come out. And then it's embarrassing. Because then it's clear that you've kind of lied. The usual reason why you say 'we' and act like it's huge is like, but see this way people will trust us and become customers of us. And what will happen is though they expect 'we' to answer the phone and emails all the time. Because 'we' is enough people to do that. And when they do then they talk to you, they talk to different people because there's 'we'. They talk to the same person all the time, it's not 'we' and they detect that. So in other words you're doing it to build trust, trust that you're big but you've done exactly the opposite. You've destroyed trust because you lied and it's going to come out when they interact with you. 'How come you barely ever release features and barely answer the email?' 'Well because there's one of me.' Now on the other hand if you're honest in the first place there's one of me, people are actually happy with it. 'Why does the email take so long?' 'Because it's just me.' 'Oh cool.' Like it's just the reverse, it's like that's awesome. I'm so glad I'm supporting an independent person. That's badass. 'Oh the server went down.' 'Yeah because it's just me.' 'Oh that's okay man.' And that happened to us at WP Engine early on when our servers went down. They were like, 'Hey I know you're trying something brand new that's really cool man.' Now if one server out of 7,000 goes down for 4 seconds there's a Twitter storm. Like, 'Hey, that's not what I'm paying for.' And they're not wrong, it's just it's a totally different thing. Again take advantage of the thing you can take advantage of which is that humanity, it's great. And you can't have servers up all the time when you're one person or whatever the equivalent is for your product, right? So don't set the expectation and then actually you get a lot of benefit of the doubt. You want to raise prices? As a big company there's a lot of, 'Well, why are you raising prices? Because you just want to pad the bottom line or whatever.' When you're one person and you send out that email going, 'Hey everybody I'm just me. I'm just trying to make ends meet. I need to raise prices a little bit more so I can hire one person.' What does everybody say? 'That's awesome. Great.' What? Great that I raised prices? You know, so I mean, talk about an advantage.
Host 17:31 ↗
I'm trying to grow a baby company right now, and one of the first things we did was like slap a picture of me and my two co-founders on our landing page. It's like, 'This is Ben, Spencer, and Joel, and we're trying to make this company happen. And like, here we are, and here's our smiling faces, and like, we're glad you care about this at all because we're literally just three guys in Joel's second bedroom trying to make this thing work.'
Jason Cohen 17:49 ↗
Right. It's great, and you get these loyal people because by supporting you, they're kind of part of it, and they are.
Host 17:56 ↗
Totally. Yeah, and like by podcasting about it and tweeting about it and sharing good and bad things, people are like totally feel connected to the journey.
Jason Cohen 18:03 ↗
Yeah. Someday, it won't be there. Well, maybe not. Maybe it'll stay there forever. It'll be small. Like 37signals have kept it forever. So, I don't want to say it will never, it will end. It may not end. But or maybe it will. It can end. That can happen.
Host 18:17 ↗
Oh, yeah.
Jason Cohen 18:18 ↗
Sure. But you want to take advantage of it while you can.
Host 18:20 ↗
There's a bunch of great reasons to tell people like the behind-the-scenes stuff, I think. Like, just philosophically, I'm into that. Like I like to share the good and the bad and let people see what it's really like. And it tends to, I think people think of it as a cost, but I think of it basically as a positive where it's like people get bought into the journey. It becomes like a drama they're following along with, and that just only helps.
Jason Cohen 18:40 ↗
And they're even part of it by supporting the business.
Host 18:43 ↗
I've literally had people reach out to me and be like, 'I don't even think I need your product, but I'd be happy to like send you like prepay you for something just to kind of support the effort.'
Jason Cohen 18:49 ↗
See? Yeah. So cool. You can't buy that. Like Google cannot spend any amount of money on ads to make that happen for Google, right? It's cool. Like you have something even Google can't do. That's amazing. So, do it. So, don't hide behind a 'we' where you just threw away that advantage.
Host 19:06 ↗
You touched on something, this concept in your conversation with Justin that I liked a lot where you're saying, 'When it comes to making decisions, I really like filters.' As in like you just decide a thing and that lets you eliminate a whole class of decisions. Do you have any like favorite filters that you apply right now these days or in the past?
Jason Cohen 19:24 ↗
It depends a lot on the decision. Like a hiring decision, product strategy decision, should you move? Like there's pretty different filters you would then apply for those things. So, I don't know about favorite filters, but I would say you can't have too many, which is nice. Like you can have too many priorities. Well, this is important and so is this and so is this and so is this and then you can't really make a decision because these options are going to have different peaks of what things they're good at and what they're not and then you're confused. So, more priorities, identifying more important things does not actually make it easier to make the decision. Filters, which are thresholds or negatives, make it easier because they cut out things until there's not many options left, which is good because that's helping you focus on making a decision. So, you can't have too many, so that's good. You can have 20, it's all right. But so like if you're hiring for someone, are there some of them based on culture, others based on things that they've accomplished or things that other people say about them when you go around. Like there's a lot of things you could sort of pile on there that you're...
Host 20:32 ↗
Mhm.
Jason Cohen 20:32 ↗
You know.
Host 20:32 ↗
I feel like you've kind of touched on one possibly. This is, I'm not sure this is exactly a filter, but like you said earlier, I do two things. Like I've decided that my life has space for two. Home and WP Engine are them. Therefore, I have a filter and I know I don't need to go work at Capital Factory right now.
Jason Cohen 20:47 ↗
That's right. Yes, constraints are useful for making decisions and you know, especially bootstrapped entrepreneurs don't like constraints. It's the whole idea. I don't want a job. I don't want this. I can be my own boss and do whatever I want and then you of course you realize very quickly like this doesn't feel like doing anything I want. This feels like I'm being crushed all the time. About to die. This does not feel like freedom at all. And then you say things like, but at least it's mine, which is true, but you're still being crushed. And then later on it's still crushing because like you know, you have employees and you really feel like you're still serving them. They're all people that either have expectations or you know, you want to provide for them and so forth and so it's still crushing and because so are the customers because they give you money and of course you're trying to make them happy. Like this whole thing if you don't have a boss and in a sense it's like no, kind of everything is a constraint and coming back on you. It's just not exactly what you thought it was. You know, sometimes these things sound so trite. There are two things or you know, you can like Peter Thiel says, you can only focus on one thing at a time or whatever you know, all these little rules. And like now, they're probably all sort of extreme in a way that makes them a bit ridiculous. The reason why they're kind of useful anyway is exactly that it reduces options. And that is good because you sit there and you look at the blank screen and think, what should I do? What should I work on? Should I write another blog post? Should I write this feature? Which feature should I do? Constraints like, let's say you arbitrarily said, here's my schedule for the day. From here to here I write code and then from here to here I do this. Like well, you don't have to restrain yourself like that. You can do anything you want with the whole day. Yeah, I know, but if I do that, I'll make sure that I'll do some of this and some of that and overall globally I want to do that. So although it's artificial, I'm going to do it anyway. Same thing with a diet. Which diet is right? I don't know. Haven't we learned that that's not just not the right question anymore? But it's also probably true that it just, anything that says, well, you can have this but not this and it's sort of arbitrary, whatever. Yeah, but if that just means you eat less and more healthily, it's probably good. Right? So yes, but the constraint is helpful because it helps you make a decision and stop thinking about it and whatever it is is probably okay. I feel that way about a lot of frameworks in business. This is a framework for product strategy. Here's another framework for figuring out how to do... Like it's not really about what's the best framework or proving that this framework is right or there's four things that this... Well, not three, not five. Sure, maybe. Like it's not really about the... It's just having any framework just kind of stops a certain part of the conversation. You start filling in boxes instead of being stuck with too many ways to think about it. And that's why it's helpful. And so I do like frameworks and I do like some of these sort of truly arbitrary rules that self-impose arbitrary rules. I like that because it just lets you get to some answers.
Host 23:42 ↗
Yeah, and get to work.
Jason Cohen 23:44 ↗
Get to work, yeah.
Host 23:45 ↗
Stop the planning phase. There's a part I want to quote from a blog post you wrote, which is kind of getting a little bit back to this advice, like what's good advice and how do you recognize it and all that and I'm going to quote you which says, 'As you accumulate a set of principles that you have a lot of energy for. You throw yourself into it and run to the extreme. Doing that is perhaps one of the truly universal rules of success that you are all in. Applying an extreme amount of energy is more important than exactly which path you're taking.'
Jason Cohen 24:11 ↗
Yeah. That sounds really good. That was really like crazy.
Host 24:15 ↗
That's good. It's pretty good. You can print that.
Jason Cohen 24:17 ↗
Yes. There's a funny story about, there's a mathematician named Littlewood in the UK. This is probably late 1800s or so and he was proofreading a manuscript by somebody else and there was this quote in there and it wasn't attributed to anybody and he made a note in the margin that says, 'This quote is amazing. I wish I had said it.' And in the final version it said it attributed to Littlewood. He had said it and forgot.
Host 24:47 ↗
That's amazing.
Jason Cohen 24:48 ↗
Anyway, so I feel like that with the old blog post. Like, 'Oh, that's pretty good.'
Host 24:51 ↗
Totally. Yeah, I've had that same experience.
Jason Cohen 24:53 ↗
It's better than I come up with now. Doing it so I don't like the whole follow your passion. That's crap. Like you know, you can be passionate about stuff and chess and that doesn't mean you should make a company doing chess. That's I think that's silly. But I do believe in there's things where you do naturally throw yourself into it and it doesn't have to be a topic like chess. It can be designing things or writing prose or writing code or whatever kind of creation thing that you like. Clearly, if you're in your zone, if you're in the flow and you have energy for it many hours a day not because you have to and you're not upset after, but because you love it and time flies by and you don't realize and you forgot to pee and all that. That's the good kind of all in. It's clear that being in that is more productive and fulfilling, both. So and of course you can't be in there all the time. But seeking things where that can happen, that's just logical. And exactly to this point of you don't know what advice is right. Actually, there's probably many paths to success and failure. Therefore, pick the ones that more naturally fit you because whatever that is, at least you'll maximize whatever that option was. And even if you make some math that says that some other option was better. But what if you can't execute that better? Then it's still not better. So going back to that notion of what drives you in that way that helps you say, look, even if it's a second best option in some objective sense, it may be first best in terms of your ability to execute and that's a way to ask what can I execute well. The trap is especially when you're a founder because that means you don't have a boss telling you what to do or holding you accountable. The trap is that you do the thing that you love, the flow thing and not do the thing the business needs you to do. So if you're an engineer, the classic version is I will add another feature today. When what you probably need to do is double the amount of traffic coming to the website because you don't have enough sales. Almost always the problem with any company is not enough sales. And I'm not saying that because VCs and growth, I'm talking about bootstrap companies, blah blah blah. Like probably the most impactful thing you could ever do is increase sales 10%. If you could add one feature and double sales, then freaking add that feature. But I'll bet you that one feature won't double sales. But there's other things you could do that actually might. And so there's no doubt that it's better for the health of the business to double sales in the next say 1 to 3 months than to add the feature that doesn't double sales. But you love adding the feature and you know which feature to add. And you will have customers that will genuinely be delighted to have that feature. Those are all true. Therefore, you do it instead of doing the thing you need to do. And since there's no one telling you what to do, you know, the trap is to do the flow thing instead of the thing that must be done or should be done instead.
Host 27:40 ↗
Mhm. But it's way less scary to add the feature. I already know how to do it.
Jason Cohen 27:44 ↗
Exactly. And that's why we, you know, the world is littered with sort of version 1.2 products that no one buys or not enough people buy. And here's another way to look at it. Look at all the risks in a business. Again, bootstrap, forget all the VC crap. Just bootstrap business. What are all the risks? Can I get enough customers? Will they pay the price that I need them to pay? Or will they stay around if it's recurring revenue business long enough for that to work? Can I do the tech support? Can I make an ad where they can tell in a fraction of a second, this is for me? Because that has to be pretty compelling and use exactly the right words because it's in the middle of all those other ads. It's the same thing with your home page or landing page because same thing. They land on it and you get 1 second. They better go, 'Whoa, nice.' That's a very difficult reaction to create in somebody in 1 second. Can you do that? Can you cheaply enough acquire those eyeballs to go say that thing to then come in? There's lots and lots of questions. All these have to be more or less in the affirmative for the business to work. And I still didn't say features yet. So here's the one thing I know for sure and a good engineer can do. I know for sure that engineer can build the features. There's actually very little risk of building the features. But, will that same engineer be able to do everything else I said? Almost for sure not. That's where all the risk is. Zero risk in building, I'm exaggerating. Zero risk in building the software, 100% risk in all the other things a business requires to exist. So, what do we spend our time on? The thing that has no risk at all because we know how to do it. That's why it's not risky. So, a good rule of thumb is to keep in mind like the one or two things a business really needs to change. It's probably more sales and that's it. But, it could be other things. But, it's probably more sales. And then ask, the things I'm doing today, is it causing that thing to increase? If the answer is no, it's a problem. Now, of course, that's a rule of thumb because you have to do your taxes and that doesn't make revenue happen. Of course, you have to do it, right? So, no kidding. There's stuff you have to do. And of course, you need to make features because actually that is tied to revenue because if it doesn't do enough, then they won't buy it or they won't stay or whatever. So, that is true. Maybe you have huge cancellations due to lacking three features. That is a good reason to go to the features because it's for growth. Now we're talking. You're getting people in the door, but then they're leaving. Fix the reason why they're leaving. Oh, now we're talking. Yeah, exactly. Why get even more people in the door if they're just going to leave? Good point. So, that would be a reason to do features in order to grow. Good point. But, usually we're simply avoiding the things that need to be de-risked and need to be addressed. And so, keeping in mind what is the number one, maybe two, like real actual business priorities that you need to be pushing forward and making sure what you're doing is actually doing that.
Host 30:35 ↗
I'm probably your target market in that rant right there. So, I'm a technical person. I know how to write code pretty well, but I'm in the CEO role for this, and I'm on sales and marketing duty and try to make sure that actually happens. Assuming that I've drunk the Kool-Aid, which I have, I agree I shouldn't be writing code. That's not going to help the business that much. And I want to get better at this stuff in a hurry. Is there anything beyond just like build the learning machine, try to get awesome, pay attention to what works, try lots of stuff, see what works for you? Is it like everything else where you just learn it by doing and try to figure it out?
Jason Cohen 31:08 ↗
Well, one has to get help from people who have done it and are good at it. Help could mean advisors, but not advisors in general, advisors just on this topic. Sometimes you pay people for that, sometimes you don't. Help could mean, yeah, learning really fast, just deciding like I need to be an expert in some of this stuff in 3 months. And that means I can't be an expert in all of it, because that's just ridiculous to say I can be an expert in all of it in 3 months. So, I got to pick something to become an expert in. So, what am I going to pick? Well, what of these things might move the needle on the business, again probably new customers or something like this. And also seem tractable. Like, build a whole sales force. Well, that doesn't even make sense. I don't, you know, you can't even hire. We don't have money to do that. So, like that's not even on the table. So, stop. So, maybe not sales. Or maybe it's self-fulfilling sales or maybe it's building an email list or maybe it's I need to get one paid marketing channel to work. Doesn't matter which one, but like one has to work. So, I'm just going to, I have to go ape and do nothing but live in paid marketing places doing experiments and blah blah blah, trying to make one work. Because if I can unlock one, then we can pour money into the one because we can afford to because it's working. And then once that's established, then you could take a breath and ask, 'What's next? Do I try to find another one? Maybe it is time for sales. Maybe I can hire someone at this point. Maybe hire someone part-time.' I don't know, but I have a few options once I have one working. So, just getting one working really well, that's my goal. And I'm going to define really well as it's pulling in, it's creating, you know, 5K of MRR per month or I don't know, just make up a threshold that says that's really doing something. So yeah, just trying to focus down on one thing and then there's probably a few options of how to get there. At WP Engine, there were some things like AdWords where I was able to find there's sometimes consultants who will work on, it's not quite pro bono, but like on a performance contingency. So, like if you don't get at least this much, you know, the cost per conversion has to be at least X or else, you know, I don't pay you or I pay you some minimum amount. On the other hand, if you blow it out of the water, you can make a bunch of money, like that kind of stuff. So, that can work sometimes for a bootstrap company who was like, yeah, if it fails, I can afford it. And if it doesn't fail, then I will have unlocked something that I can afford to pay for and then I can, you know, revisit at the end of that contract period what to actually do to make it sustainable. So, I did that at WP Engine, so that's possible. Same kind of thing with, well, really any paid stuff. It could be AdWords, it could be other channels, it could be affiliates is another whole universe that's a whole different sort of a thing. It could be email marketing, although I think that's more of a longer-term play like content marketing is where you can't just do it and get a return. You have to do it and work it. And so, it's strategic, but it may not be fast. And that might be okay. You might be all right with strategic and slow. We're already doing content marketing, which is that, so maybe it's okay. Or you might say, 'Look, I am already doing stuff that's strategic and slow. I need some things that are not slow. I need some things where I pay a dollar and get a customer this month.' So, that's what I need to focus on, right?
Host 34:18 ↗
Can I describe where we're at and just have you like ask me questions and do a health check? I'm like I'm at the doctor's and you're just like, 'Let's check this and make sure this is okay.'
Jason Cohen 34:26 ↗
All right.
Host 34:27 ↗
All right, so we started this company back in May. It's me and two co-founders. We're all technical. It's called Tuple. And our goal is to build an app that lets you do remote pair programming. So, two people on one computer writing code together. We think all the solutions out there are pretty crappy because you need to make something that's really, really fast, screamingly fast. And the existing things out there have too much latency and people don't like them. I started off by doing pre-sales. So, I reached out to a bunch of people. I have a bit of an audience. I came to this with an audience, which is nice. I've been working in public for a long time. So, I had a bit of a Twitter following and some email people and a podcast. And through that, started getting people on an email list and actually populated a paid alpha. So, it's pre-sold about $8,000 worth of people on that. So, we have a handful of teams and a handful of individuals who have said, 'Yeah, I want to try it. I want to be your first customers.' We're hoping to launch that alpha early next year. Get the first people in there. We have a bit of a like minimal viable versus smallest lovable product thing where if our whole pitch is like it's going to be really fast. And we know that's the most important thing, but it's really hard to make it really fast. So, we're kind of racing the clock to make it fast enough by the time that we want to hit.
Jason Cohen 35:40 ↗
Do you have to use a certain IDE? Like it integrates with something?
Host 35:43 ↗
No, it's a desktop app, so it could be anything.
Jason Cohen 35:46 ↗
So, you can use your terminal, your IDE, whatever you want.
Host 35:49 ↗
So, is it like desktop sharing but you're super smart about diffs, sending diffs and compressing that and I don't know, things?
Jason Cohen 35:56 ↗
That's right. Yep. And like really good keyboard support and dual mouse and also pairing specific features. Like I can send you a link and it auto opens in your browser so we can look at the same Stack Overflow article really easily, kind of thing.
Host 36:08 ↗
That's nice.
Jason Cohen 36:09 ↗
The interest is great. We got through like 3,000 people plus on our email list. People are asking me pretty frequently to get into the next alpha beta. Like I'm telling people no and they're like, 'No, please. I really want to.' So, like the market feels very there where people are dissatisfied by the existing tools. We've promised a lot and it's a kind of a hard thing to deliver. So, that's like one of my concerns is like we it's I think we eventually will have a great product that will deliver on these things that we're saying, but to do it fast is hard. So, we're kind of in this thing where it's like we should get something out there and get the feedback, but also like it's going to take a while to get it to where we want to be, of course. So we have this sort of push-pull going on.
Host 36:49 ↗
So, first of all, I'm kind of hung up on this thing of like, if it's not really, really, really good then the business isn't going to work. I do see that in the long run. Like, why would someone love, like not just like, but love the tool? Like, latency that's so low that you don't even know what's going on? Totally is that, especially with developers. So, like, 'Well, how does it work?' You know, like, I get it. That's I totally agree. But, this whole thing of like, well, we launched in May, except it's still in alpha and we're as far away it's still going to be hard to get the stuff we want and yet everyone's asking for it. So, to me that sounds like a contradiction. You're saying the customers are saying, 'I want to pair program with it.' And you're saying, 'No, you don't understand. No, you don't.' Cuz it's not a little bit faster. So, you know, one thing to consider is they may be wrong because, like you said, you may be promised a certain thing and that's what they're thinking and they won't get it and they'll be upset. So, they may be incorrect. But, what if they're correct? What if you're right about the in the long run about having the best product? But, what if you're wrong about what people will pay for today, pay for now? So, for example, if I'm used to a workplace that has pair programming and on the other hand, the engineers in the building say we'd really like to work from home sometimes, but there's no way to make those two things work. Pair programming and working from home is hard to do simultaneously. So, here's Tuple, a way to do that. And they're like, 'Oh my god, I could transform the way that I work.' Except you're saying because the latency is 100 milliseconds, not 50 milliseconds, I'm not allowed to do that. Dude, I will take a slightly higher latency so I can work from home. Do you understand the transformation that is? The difference between not having to commute at all and having a slower than it will be Tuple changes my life. And the other part makes me go from Tuple is required to and also I love it even more.
Jason Cohen 38:50 ↗
Why would you stop one until you have the other? Bad. No, no, no, let him do it. So, I don't know which one's right because, you know, maybe you're right. Like the experience is so bad right now that actually they would be disappointed. I don't know. But my guess is usually creators are extremely self-critical.
Host 39:08 ↗
Mhm.
Jason Cohen 39:08 ↗
If it's not all the things that you imagine, it's just not good enough and you're in fact not even proud of it. And you certainly feel bad charging money for it cuz not that good. But this is the wrong mentality for a new product. It's the right mentality for a new mature product and maybe even a mature company who can't really have a crappy product cuz it would be contra brand otherwise. Fine, but none of these things are relevant to you or me for that matter, right? There are those phrases like if you're not embarrassed by your first version, then you release too late and all that kind of stuff. And you know that cuz you said SLP and all that stuff. So, you know all that. But still maybe you're doing it anyways. Maybe allowing all those people to do it and charging them for it even would work. And they would say yes. And then look, your company would have a lot more revenue, which would be great. It would help you do everything. Revenue solves all problems. And so, you know, maybe they're wrong cuz they don't understand how bad the experience is, but maybe they're right. Maybe they don't even need link sharing. Maybe there are certain use cases like the one I just mentioned, but there's probably I'm sure there's other more common ones where No, you don't understand. They have zero. You help them go from zero to something and that's huge and they'll pay for it already. Then you can go file the edges so you can charge more or they can be more thrilled and tell their friends cuz it's that good. Yeah, then. But going from zero to something could change a lot of people. So one is remote workers just in general like companies that have remote at all. Also I would ask like who what kinds of organizations are obsessed with pair programming at all like whether or not it's remote. So like if I'm an extreme programming organization then I have to. I doubt there's very many of those, but just you know, whoever whatever is, you know, maybe some famously are. If I'm just obsessed with pairing at all, I might need this. I mean, who knows like who knows what the use cases are even if I'm in the same office, it might still be there might still be a reason why we don't like it's actually nice not to sit next to each other for some reason. You know, even we only have 610 total people and we have engineering on three different floors right now. So we have pairing rooms, but sometimes they're full. So like even if everyone's in the building, you might need this. I don't know. So I wouldn't arbitrarily restrict those use cases. Maybe someone would pay for it. So I think it's good to maintain that high standard for what you think is good. That's good. But it's bad if it means like I feel bad about charging or I'm not sure if I like then it's bad.
Host 41:48 ↗
Yeah. Okay. So like one of my options is like just keep going full speed ahead on the sales. We could almost certainly close more people. Like there are people that want to sign up to like pay to be in the beta that launches at some unknown date in the future. Like am I crazy to not keep doing that?
Jason Cohen 42:05 ↗
Well, why would you not take their money?
Host 42:07 ↗
I guess for focus because we're sort of at the point where the cash in the bank is useful, but we're not hurting for it. And so like me doing like product management, for example, and like testing that the app out with people and things like that is seemingly more useful right now.
Jason Cohen 42:25 ↗
Well, putting money in the bank is one utility of revenue, but not the only one.
Host 42:30 ↗
Mhm.
Jason Cohen 42:31 ↗
It's a commitment by the and a signal by that customer.
Host 42:35 ↗
Mhm.
Jason Cohen 42:36 ↗
And that is valuable.
Host 42:38 ↗
Yeah.

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APA

Cohen, J. (2026, June 6). 69: Sound, Actionable Advice with Jason Cohen [Interview transcript]. The Next Track. CEOInterviews.AI. https://ceointerviews.ai/interview/973376/

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Jason Cohen. "69: Sound, Actionable Advice with Jason Cohen." The Next Track, 6 Jun. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/973376/.

BibTeX
@misc{cohen2026_973376,
  author       = {Jason Cohen},
  title        = {69: Sound, Actionable Advice with Jason Cohen},
  howpublished = {Interview transcript, The Next Track. CEOInterviews.AI},
  year         = {2026},
  month        = {jun},
  url          = {https://ceointerviews.ai/interview/973376/},
  note         = {Speaker-attributed transcript with timestamps}
}