Episode 825 | Talking Tailwind CSS and Founder Fitness (with Adam Wathan)

Rob Walling:
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I’m your host, Rob Walling, and in this episode, I welcome Adam Wathen, co-founder of Tailwind CSS to the show. And in this show, we actually talk about two very disparate topics because I had originally invited Adam on to talk about founder fitness or just staying fit as a founder. This isn’t about lifting a bunch of weights and spending two hours in the gym every day. It’s actually about how to do it as quickly as possible and staying in half as decent shape as you’re running an all encompassing company that takes all your energy, time, and focus. And I invited him on, and then in the meantime, he has posted about how they had to do pretty dramatic layoffs at Tailwind. And so in this episode today, we dive into those two topics. First, an update on Tailwind Labs and how they’re doing as a company and everything that went down there. 

And then we switch it up and head into Founder Fitness. Before we dive into my conversation with Adam, MicroConf Europe tickets are on sale. This year, MicroConf Europe is in Recyvec, Iceland at the stunning Harpa Concert Hall. Dates are September 21st through the 23rd of 2026. We’ve already announced our first couple speakers, but I would guess we will sell out long before we announce all the speakers. Two speakers in addition to myself include Agnes Giannisane of Agelics and Corey Haynes of Conversion Factory. You can head to microConfEurope.com to grab your ticket. Tickets will never be less expensive than they are today. And as you know, ticket prices go up every month or two, and we’ve sold out every event for the past several years. So if you want to come hang out with me and I don’t know, about 150, 175 of your favorite bootstrapped founder friends, should head to microConfEurope.com. 

And with that, let’s dive into my conversation with Adam. Adam Wavin, thanks for joining me on the show.  

Adam Wathan:
Thanks for having me, sir. How’s it going?  

Rob Walling:
It’s going really well, man. I can’t believe … Is this the first time you’ve been on startups  

Adam Wathan:
For the rest of us? Yeah, I’ve never been on this show  

Rob Walling:
Before.That’s an oversight on my part. You’ve spoken at MicroConf, we’ve hung out, we’ve had dinner, we’ve had drinks and talked email for years, but I just sometimes it’s  

Adam Wathan:
An open- Yeah, no. Well, I’m excited to be on because I’ve been listening to the show since a long time before we ever met or I got to speak at MicroConf or even attend MicroConf. So it’s definitely awesome to be on.  

Rob Walling:
And there’s a kind of coincidental timing because producer Ron had told me, “Hey, we should do an episode about founders and fitness,” because there was a TinySeed Slack thread that kind of went wild. People talking about getting in shape and not just about lifting weights, you can get that anywhere or fitness, but it’s like as a founder, usually with a family, how do you do this? And so I went on X and said, “Who should I invite on to talk about this? ” And several people mentioned you. So I went to invite you around the holidays, and then within a few days, you had that podcast episode where you’re like, “We laid off 75% of our engineering tier, whatever.” And I’m like, “Oh my gosh.” So it’s brutal. It’s usually the worst day of a founder’s journey when that happens. And I feel like I want to talk about both basically. 

It would be an oversight not to talk about your experience. And then I want to hear an update too, because there was such a public outreach and that podcast episode is called Adams Morning Walk, and I think it’s episode three or four that basically went viral. And I think Jason Fried was commenting on it and it just blew up and there was this whole people wanting to sponsor. And people in Slack groups I’m in were like, “I’m buying … I don’t even use Tailwind and I’m going to buy a license right now.” So it was like a  

Adam Wathan:
Real- Yeah, it was crazy. Yeah.  

Rob Walling:
So we’ll get to that point, but take us back to, because when I think of Tailwind CSS and Tailwind Labs, which is I think your company around the open source project, last I heard publicly, you’re doing millions a year in revenue. It’s not recurring, but it is one-time purchases, right?  

Adam Wathan:
Yeah.  

Rob Walling:
And you had a small team of six, seven, eight people, so something like that?  

Adam Wathan:
Yeah. We’re eight people kind of at our biggest. Yeah.  

Rob Walling:
And so plenty of budget to handle people, but then you described this slide in revenue that you’ve seen over the past, what is it, 12 to 18 months. You want to talk people through what happened?  

Adam Wathan:
Yeah, like two years. Yeah. I guess so. I mean, I don’t know how far back we go, but basically tailwind, obviously a really popular project kind of becomes sort of a de facto standard it feels like for building new front ends for websites. We sort of hit a peak, I would say, in revenue at the beginning of 2023. So this was kind of like right before ChatGPT first came on the scene and people started getting excited about AI. And also just right at sort of the peak of tailwinds, I guess you would say growth, it sort of feels like it’s sort of saturated the developer market at this point. Everyone’s heard of it at this point, whereas kind of back then people were still coming into it and switching to it from other things. So right around that time is like when we were sort of doing the best and I think there was a bunch of factors there. 

Again, our business model was like one time sales. So the more new people are finding out about it, the better for us versus just like the market saturation sort of point. There also wasn’t as many people building like competing products, which that never lasts forever, but that’s like a nice spot to be in, especially not as much like free open source competition. And yeah, the AI stuff hadn’t really happened yet. And then, I mean, we were doing like really, really well at the beginning of 2023. We’ve always tried to pay people more than they’d probably get somewhere else. That’s something I’ve taken a lot of pride in is no one ever asked for a raise at this company ever and everyone got them multiple times. Yeah. So we were doing really well then and then things like started to sort of slow down gradually over time. 

But the way I described it on the podcast is it really felt like a sort of boiling the frog scenario because it was just happening so gradually that in my mind, like every month just kind of felt like, “Oh, we’ve sort of hit the bottom.” You know what I mean? Yeah, we had like this really booming period, but it’s like dropped off and we’ve sort of hit like a stable floor. And it sounds like sort of silly to say that and even just like talk about me passively making assumptions about that. But I think probably like a lot of founders can empathize with just like, you’re not primarily like a CRO at the company or a CFO or whatever, right? It’s not like I’m spending all day every day analyzing spreadsheets and doing forecasts. I’m like working on the product, trying to figure out what we should do next, whatever. 

As long as you can pay the bills and it feels like there’s money left over in the bank account at the end of the day, I didn’t analyze it that deeply. And eventually towards the end of last year, I decided, you know what, I should really just make sure that my assumptions about things being like stable are correct. And when I actually like plotted out the trend, I realized that revenue was dropping like pretty consistently by say like 15 grand a month and it kind of dawned on me that like I’m not really going to feel this until like we crossed that threshold where it’s like dropped enough to be like a real problem. It feels like a very black and white thing. It’s like everything’s fine and then all of a sudden you don’t have enough money to pay people. And I realized if the trend continued, like we weren’t going to be able to make payroll within about like six or seven months. 

Yeah. So that’s when it kind of became sort of a bit of an emergency and I realized, okay, so what are my options here? I can either keep trying to sort of like turn things around and get back to the point where we can still afford the team that we have, which obviously that’s what everybody wants. That’s what I wanted regardless of what I did, but ultimately decided like no matter how hard I try to do that, that’s what I’ve been trying to do for the last two years and none of the things that we’ve tried have really like fixed it and turned us back into sort of growth mode. No matter how hard I tried to do it, I don’t actually have control over it. You know what I mean? All I can do is try to affect it as much as possible. So it kind of felt irresponsible to me to just not try to make changes that sort of planned for the worst case scenario because the last thing I wanted to do was not be able to turn around and then one day just have to tell everyone, “Hey guys, sorry, we can’t afford to keep everyone around and we don’t have enough money in the bank to kind of provide you with a solid severance for transitioning to the next thing.” I wouldn’t be able to live with myself doing that because I just know how stressful that would be for people. 

So instead just made the decision, okay, well, let’s cut the expenses now while we can still give everyone a really healthy severance and make it not like a stressful situation for them and help them find their next thing and then figure out how to turn it around from there. And in terms of like what I sort of thought happened, it sort of blew up because it was like a GitHub issue where someone was trying to add support for like markdown LLM endpoints to our docs and I had sort of like not prioritized it because I was busy trying to like make the business work. And one day someone just posted like a sort of rude entitled comment in it just saying like, “When is someone going to look at this? It’s been this many months or whatever.” And that was like the same day that I’d laid everyone off and it just was like the perfect storm of like, “Okay, this has just gotten under my skin.” So I just replied to it and I just sort of explained like, “Listen, this feature that you want to add is going to just make less people come to our website and traffic is already down by like 40%, which means revenue is down by a lot because our website is the distribution for our product.” And me spending time working on this feels like it’s in like conflict with our own business model. 

And right now I’m already in this situation where we just had to lay all these people off. So how can I justify spending this time on that, right? Yeah. So that’s what ended up blowing up into the big news story was like, okay, Taylor Labs just laid off a bunch of people because of AI, which I don’t think is necessarily the whole story, but I do think is like a big part of the story. And what we’ve been trying to figure out ever since then is how can we sort of swim downstream instead of upstream because AI has basically been our competition ever since it showed up. And I don’t really want it to be that way because I’m hugely excited about it and I use it every day and it’s like changed the way that I work. And so it’s really just sort of like, ah man, it sucks to feel like this technology that I’m personally excited about is in competition with our business. 

And surely there’s got to be some way to like reimagine what we do to sort of work in this new world. And that’s kind of what we’re kind of working on now. But yeah, when I put that podcast out, it really, I don’t even know why I put it out. I’ve been doing this podcast where I just sort of candidly talk about what problems I’m working on once a week or something like that. And I don’t think I had tons of listeners at the time because it wasn’t really intended to be that. It was really just like what’s on my mind, I’m walking the dog using like a little battery powered lav mic, you know what I mean? It’s not a highly produced thing, but that ended up really blowing up and tons of companies kind of came out of the woodwork to sort of sponsor the project, which we’d been having trouble sort of finding sponsors for the project before then. 

And yeah, like honestly really changed the direction of our business financially. Now there’s enough coming in from just company sponsorships to cover our expenses without us even worrying about the products. So that was nice. But yeah, it was really just a crazy, unexpected sort of whirlwind … It makes me think of like the whole just luck surface area thing. You talk about things, you put yourself out there and like things can happen. But yeah, there was no strategic goal when I released that podcast. I was just venting about something, you know? But yeah, so anyways, whatever. I’m all over the place with this story here, but that kind of gets us to today.  

Rob Walling:
No, this is good. You recapped it. Yeah. I was going to joke that in your Morning Walk podcast, I love your Foley work and how you insert fake footstep noises and fake leaves wrestling in the background because I know you’re in some studio. Saying hello to fake neighbors and- Exactly. It’s great. You got AI go. We’re good for you. Yeah. I mean, there’s a few things I want to touch on and we’re also going to talk about fitness and how you’ve really reworked your body in the latter half of the podcast, but there’s a couple things that I’m wondering, and I’ve heard you talk about them over the years that I’m wondering if you and I could Monday morning quarterback them and say like, if three years ago you had tried this, do you think as the founder or as a co-founder, I guess, and most knowledgeable person on this, do you think this would have changed things or not? 

And there’s a couple things. One is recurring revenue.  

Adam Wathan:
Yeah. No, let’s talk about it.  

Rob Walling:
Yeah. I heard you talk about it on your podcast because someone wrote in to start to the rest of us and said, Adam Wathen was talking about this and Hackers Incorporated, I think was your show.  

Adam Wathan:
Yeah, yeah.  

Rob Walling:
And you were talking about how it wouldn’t work being recurring. And then Ruben and I, here answered the question of like, here’s how we might think about. We have like 23 years. I didn’t hear that 

One. Oh really? Oh, I should send it to you. It’s probably like a year old now, maybe more. And all that said, when you posted the episode about how you had to lay people off, there were some private Slack groups I’m in where founders were like, “Oh, I wish she just charged a subscription because I would pay a yearly and annual fee for it. ” And look, I’m not saying that three people saying this in Slack groups means you should have or anything, but of course I’m the recurring revenue guy. I believe I’ve done one time sale businesses, I’ve had them and I remember how swingy they were because in the 2008 financial crisis, I lost 90% of my revenue from one month to the next. And I was like, “Fuck, it’s because it’s not recurring.” And I think you’ve commented that you’re down maybe 70% from peak revenue. 

And so the thought I have, and I know it’s dicey because you have, it’s tricky because you have a developer component and should you charge, because what is it like three or $400 one time? Is that about what it is?  

Adam Wathan:
Yeah.  

Rob Walling:
Could you charge that? The question is, could you charge that every year or would you charge 400 upfront and then charge $100 or $200 a year as a maintenance fee, something like that. Do you feel like looking back to four or five years, do you wish you’d done that or do you … I guess what are your  

Adam Wathan:
Thoughts on it? Yeah, that’s a good question. I honestly don’t think so. There’s some things that I maybe would’ve done differently. I think we probably could have done subscriptions for team licenses from day one, which would’ve honestly probably been enough to make a pretty substantial difference because I just don’t think businesses are as sensitive to the one time versus subscription thing, especially if it was just like an annual thing as maybe individuals. And I think there’s more justification for it too, because you have different people joining the company and leaving the company and you want to keep maintaining access for those people, whatever. But sort of like the strategy for us when we picked the one time pricing model was, it was really thinking about how value is delivered in the shape of the product at the time. It’s a bunch of website templates and components and stuff like that and you could subscribe and download everything and then cancel and have everything and then come back six months later, subscribe for one month again and download anything new and then leave. 

And that just felt like it’s not the same as like a SaaS product where you’re coming in there and using it every single day. I think like an annual subscription could have maybe worked, but I still believe that like our conversion rate was a lot higher because there wasn’t that like subscription friction. And a big part of our mentality for it too was like, oh, I don’t know how long Tailwind’s going to be popular for all this developer tooling goes in cycles. It really feels like capitalize on the moment and basically just like sack away as much profit as we can as a company in case one day this all goes away. And maybe that decision contributed to that outcome in some ways, but also at the same time, like I did get what I wanted out of it. I’ve never made it a secret that like the business has done really, really, really, really well for the founders while paying people extremely well and creating I think a really fun and relaxed and interesting place to work for the people that work here. 

But at the same time, like, okay, even if I’ve put away enough money that it feels like I’ve basically gotten an exit out of this business in a lot of ways, that doesn’t mean that once the cash flow and expense balance is like out of whack, we still have to make changes at the company, which sucks because it doesn’t make sense to personally subsidize a business that’s not working on its own, of course. And I think that’s like a topic that I think the general public hasn’t run a business, I think maybe does have a little bit of a hard time empathizing with, but any business owners I’ve talked to, of course, understand that. You wouldn’t invest your own money into a business that’s not working, which is basically what you’d be doing then. And then you’re also stringing people along, like keeping them in a job at a company that isn’t working, you know what I mean? 

They should be taking different opportunities than doing something else anyways. I guess I believe that we would have had to figure out a way to make it feel more like a subscription product to really justify a subscription. And maybe that’s like what we should have focused on. And I’ll say like the next thing that we’re working on, we are planning for it to be subscription revenue, you’ll be happy to hear. But yeah, I don’t know. I guess I just feel like if we went back in time and made a subscription for everyone from the beginning, I still have those same concerns about really high churn, like the sort of churn that people have on subscription education products, which I think is a historically really challenging thing. I also just think like we would have just made less total in revenue along the way. And if we found ourselves in this current environment where like people are still choosing to use AI to like generate UI stuff instead of paying for a product, they would have canceled anyways. 

So I obviously, I can’t go back and AB test it, you know what I mean? But I guess my point is, I don’t really look back with regret as if we made a mistake because like obviously it sucks to lay people off and be in this situation where revenue is dropping. When I really zoom out, I still feel like it’s still been a really great outcome for me and I’m still like really grateful for how things have played out. So I don’t know, but I’d be really curious to hear like what you think for sure. Well,  

Rob Walling:
And there’s two things. You said it’s a great outcome for you. I actually would argue it’s been a pretty good outcome for your team. Even those that got laid off were paid, I believe above market salaries and you gave them generous severance and yes, it sucks to be laid off, but you took care of those folks.  

Adam Wathan:
Yeah.  

Rob Walling:
So, but yeah, let me weigh in on the subscription. I think an annual subscription would have worked. That’s my gut. You think so? Yeah. And that it would have given you … Well, here’s what it would have done. You’re right. You would have had probably less of the boom, boom years when you were making loads of money, but I think it would have been more stable. It would have grown, grown, grown, grown, grown, and then maybe if anything, it would have plateaued. And it’s just recurring revenue is so, especially annual, it slides so much slower than any type of one time.  

Adam Wathan:
So do you think we should have just done like the same kind of get your foot in the door price and then either recur at that same price annually or maybe like a lower amount to sort of …  

Rob Walling:
Somewhere in there. I probably gut feel would have been like, look, if it’s 399 upfront, you get updates and stuff as long as you pay the 399 every year. You can use it in perpetuity, but you don’t get what, updates or support. I mean, that’s usually what comes with an open source project and then every year everyone gets to evaluate. And you’re right, I do think your churn would be higher than like enterprise SaaS or Salesforce, but I think it would have been significantly low. Monthly would have been a disaster. I don’t think you all would have done monthly.  

Adam Wathan:
Yeah. Monthly, I don’t think would have worked. I guess in my head, I had pictured it as like, “Well, if the lifetime is this, then the annual has to be less than that. ” And you’re kind of saying, “Eh, not the case.”  

Rob Walling:
I would be super curious to see. And even if you were to do a 399 upfront and then it’s 199 a year, it’s still something, but I don’t know why you wouldn’t just do 399. That’s probably where I would have leaned, but the other thing is, and I want to ask your opinion on this because I don’t know the business well enough, is one thing I see working, there’s only a couple tinySeed companies that are dev components. I mean, maybe it’s two or four, it’s very small. They’re also seeing impact by AI, being heavily impacted by it by the way, because people aren’t thinking about a component anymore when AI can just go write all the code as you’re seeing. But one of the ways that they make quite a bit of money is they do have their developer two to $400 thing, but then they have their mid-market, five or 10 grand thing a year that’s for, we’ll call it enterprise. 

Usually enterprise is more like 35K and up and maybe you could have that too, but even just a five or $10,000 package that is, it’s for teams, but it’s also when they want more support and they want … There’s stuff you throw in that enterprises care about. And the churn on those, I think would have been very, very low would be my gut.  

Adam Wathan:
Yeah. Yeah. Once you got in the door there, those contracts, they collect dust in some folder for  

Rob Walling:
Years,  

Adam Wathan:
I  

Rob Walling:
Guess. They do. And if you had to go through procurement, then you make it 35K and up. I mean, that’s kind of a rule of thumb. But I’m wondering, aside from just not wanting to do that, because enterprise is not fun and may hiring a manager, aside from that  

Adam Wathan:
Reason- Well, honestly, we’re doing quite a bit of that now with the partner program.  

Rob Walling:
That’s what I was guessing. Yeah. I was wondering if you wished you’d done that earlier, if you think that would have worked, because that was always something I thought, man, I think these orgs would pay a lot more than 300 a month.  

Adam Wathan:
Yeah, we probably should have, honestly. I think I took an irrational amount of pride in trying to build an open source thing that was sustained on real profits from making a real product that delivered actual value. And I hated the idea of feeling like we were making it work on donations. I wanted it to feel like the market was making it work, which I think I’ve changed my opinion on that a little bit in the sense that I think we are providing real value to the companies that are part of our partner program. Yeah. I don’t think people tend to just give people money for nothing. If they’re choosing to give you money for what you’re offering, then they’re seeing value in it. Whether that’s like the exposure that they’re getting from the website or just having a more direct connection with our team to kind of like skip the line when they have bug reports and stuff like that.  

Rob Walling:
And wanting it to exist, man. I mean, there are companies I’ve worked at where when we would implement a technology sidekick, for example, when we were like, “We can only give him,” Mike Perham who runs it, right? We can only give him $1,000 per Sidekick instance. I was like, I actively want to support this more because we had so much infrastructure built on Sidekick. I think there’s that. I want this to exist. I don’t want it to be abandoned. The Twitter puts out a UI framework and we were using it at drip and guess what? Two years later, nobody’s maintaining it. And so I think there’s more value. To me, it was never a donation. It’s A, we do get priority support and I remember that being important for us because we had some downtime or some glitches on a Saturday.  

Adam Wathan:
Yeah. I mean, for a product like Drip, your Q is-  

Rob Walling:
Incredibly important.  

Adam Wathan:
That is some of the most critical infrastructure for the whole product, right?  

Rob Walling:
And so for you, I think if there’s a company, I mean, if there are companies that want to pay 10 grand or 35 grand or whatever the number is that’s significantly more than 400, I don’t see it as a donation, man. I see it as them. And it’s not just like, “Oh, let’s support this project.” It’s like, no, this product is critical because it’s in our application and thousands, if not tens of thousands of lines of code and we want it to exist. So that’s more of what I was thinking.  

Adam Wathan:
Yeah. And a lot of people see that, which is good. It’s like an insurance policy, which I think … Yeah. So I mean, I’m glad we ultimately did that. That’s like worked out really well, especially with that podcast that came out. It just created this perfect storm where we had magazines writing articles about the impact of AI on our business and other businesses now kind of wanting to be on the good side of that PR and sponsoring us and stuff. So yeah, that really was a welcome surprise, of course, just having all that stuff set up to even be able to take advantage of that moment. So really grateful that that worked out the way it did, for sure.  

Rob Walling:
That’s great to hear. I’m glad. It’s kind of a happy ending for now.  

Adam Wathan:
Yeah. Yeah. And we’ve got stuff that we’re excited about now. Now we’re working on, we kind of pre-announced this like Ui.sh is the product that we’re trying to build now, which is the idea is to basically augment the AI tooling that people already use to be able to produce better front end code, better design, sort of take all of what we’ve learned building stuff over the years and sort of teach the robots how to do that so that you can get some of those benefits in the stuff that you’re doing. And I mean, it seems like an obvious thing for us to work on. And it seems more obvious than ever now that I’ve been working on it for a while and feel like I’m making it work and know how to make it work. But the AI stuff really is such like a black box full of so much trial and error that until you feel like you have the secret passphrase to get it to do exactly what you want, sometimes it feels like, how am I supposed to make this thing even do what I want? 

But I think we’re going to be allright for sure.  

Rob Walling:
Glad to hear it. Well, let’s wrap up that thread and move on to founder fitness. Thanks for talking us through that, man. I know it can be hard. Yeah. I think to talk about stuff that isn’t working or hasn’t worked, and I appreciate your openness and honesty both before this and on the show.  

Adam Wathan:
It’s good to have places to talk about it, honestly, and to have the opportunity to talk to people with tons of experience like yourself that can help with ideas. And I think suffering in silence is the wrong play when you’re in these situations. You need that outside perspective.  

Rob Walling:
Yeah. I’m really glad it turned around. I was definitely rooting for you. I  

Adam Wathan:
Appreciate it. There were a lot of  

Rob Walling:
Replies to your Twitter threads, but I was in there. I was like, “Man, I hope you pull through.” Well, let’s switch it up and talk about founders and fitness. And it’s a total right turn. Yeah.  

Adam Wathan:
Total 180s. This is  

Rob Walling:
So much easier to talk about. Realistically, the reason you came across my radar I think is because you talked about it on your podcast, Hackers Incorporated, former podcast. I don’t know that you do it anymore, but you talked about it, you lost 70 pounds, you got to about 12% body fat and you still, do you still bench 315? Dude, that’s a lot of  

Adam Wathan:
Weight. I can still bench 315, but I’m not a 12% body fat.  

Rob Walling:
Yeah, which is fine. We’re not holding you to that. But the idea is that you are a co-founder of a business, you care about it a lot. You work on it hard, you have a family, you’re a dad, and most of us are like, “How can we fit this in? ” And you’ve talked about having really short workouts. And this is the thing I want to start with because I’m most interested in this because I’ve recently … I don’t like working out, but I like being in shape. That’s just how I’m working. Some people really enjoy working out too, and I envy them. That’s not me. So I’ve recently dropped from like three sets of whatever to … I’m doing two sets with higher weights to failure, whatever. It’s stuff that I’ve heard on the internet and my 15 year old tells me to do. 

And so I’m trying to cut it down. I’ve been getting it down to about 20 minutes and it’s twice a week for me, man, of three. Three is big victory, but twice a week is like plenty. I’m six foot two and I’m pretty slender. It’s not like I need to work out all the time. But you’ve won upped me. You didn’t just six minute abs. You seven minute abs to me because you have 15 minute workout sessions.  

Adam Wathan:
Yeah. So I’m actually not training that way right now, but I can talk about a lot of different stuff. So stop me whenever, but I’ll explain sort of what I was doing there. So when I was like, I really made this commitment to sort of like shed a bunch of weight because I was very overweight and I think like anyone who’s ever been overweight, once a week they have that day where it’s like, “Man, I’m going to turn this around. I got to get in shape, whatever.” And for me, how I got that process started at the time that really made it happen was I knew like I need to find some way to basically be spending money on this so I am taking it seriously. I know what a lot of people do. A lot of people who have a hard time going to the gym like signing up for like classes at the gym or like group classes because it goes in your calendar and it’s not just like something that you’re going to make time for like, “Oh, I think Tuesday afternoon, I’m going to go to the gym and get in an hour or whatever.” It’s on your calendar like a dentist appointment. 

And for a lot of people, they That’s enough to get them to go. I wanted the same thing for just eating healthier and controlling my portions better and all this stuff because ultimately that’s what the losing weight comes down to. It’s hard to just exercise that away. A lot of that is changing bad habits and bad relationships. You have food and stuff. So I found this service called My Body Tutor where it was a couple hundred bucks a month and you worked with a coach who would basically, you do a phone call once a week, but they would also text you every single day. And you had to fill out a log at the end of the day and send it to them with like, “Here’s a picture of every meal I had today, a bunch of really interesting questions. How well did you sleep?” There’s gratitude journaling in there. 

There’s a lot of stuff that’s just all kind of comes together to sort of get you into a more positive, healthy mindset and helps you sort of maintain these habits. And for me, it was just like, okay, if I need to send pictures of what I’m eating to someone who I don’t know every single day and I’m spending a couple hundred bucks a month on it, my hope is that that’s going to be enough to get my ass in gear. And it worked really well for me in that sense because it’s really hard to send a picture of like a blizzard from Dairy Queen to some really in shape fitness coach that you’re working with and not feel like an idiot. So that was sort of like the first step for me that really helped me sort of like get into that habit. And once you sort of have that chain going, it’s a lot easier to be like, “Okay, well I’ve eaten well and stuck to my calorie budget for the last two weeks. 

Do I want to throw that away today?” It’s like the Jerry Seinfeld don’t break the chain thing. So that’s like the summary of really like what worked well for me there. And of course there’s like a lot of different strategies that you can actually implement to do better with your eating. Things like eat super, super slow, take a drink of water between like every bite. Don’t do anything while you’re eating. Make eating as boring as possible so you don’t, so you want to be done with it and get back to what you were doing. If you’re sitting there eating lunch and like browsing your phone, it’s way easier to like eat more because you’re sort of entertained. But if it’s like, no, it’s just me and this plate and I just want this to be over with because I want to get back to those interesting project I was working on. 

Yeah, you tend to not eat as much. But when it comes to the workouts, historically I’ve done like a lot of heavy weight training because I used to compete in power lifting and I kind of got into that because through a bunch of different attempts at getting into like working out, I think like most people get into working out because they want to look better. I think that’s generally why people do it. And it takes a lot of time to see visual improvements there. So it can be hard to sort of stay motivated to stick with it. But then I sort of got into strength training over just like working out to look better and now you’re like keeping track every day of like, “Okay, I did this many reps or I lifted this much weight.” And you can actually see improvements there like day to day, week to week. 

And that’s actually really motivating because you can see, okay, well, I benched 185 for 10 reps last week and this week I got it for 11. It’s like, “Yeah, this is awesome. I’m making progress.” You sort of get addicted to it because that feedback cycle is so much shorter versus like taking pictures every day and hoping that you start to look like you’ve put on some muscle or something because that could take months and months and years and years really, right? I just really got into that. And I’m sort of an extreme person with like most things that I do and sort of like the extreme version of going to the gym doing strength training is like competing in power lifting and trying to like lift more than everybody else and lift as heavy as you can. So I kind of got into that. But that form of training didn’t really work well when I was trying to cut down a bunch of weight because no matter what, unless like you’ve never been to the gym, if you’re trying to lose weight, like you’re going to get weaker in the gym because your body doesn’t have as much fuel as it did before and your body isn’t this perfectly efficient machine that can burn only fat and not lose like any lean body mass or any muscle or anything. 

So if I was going trying to squat heavy and bench heavy and whatever at the gym, my numbers were going to go down and I worried that that was going to sort of like hurt my excitement and motivation. So I wanted to restructure my workouts into something that felt like getting lighter and losing fat was going to like make my performance at those workouts better. So I started doing these like weighted vest circuits and it’s something I picked up from this guy, Jim Wenler, who’s like anyone who’s like been into power lifting will know who this guy is, but he’s just like a really longtime well-known strength coach guy. And I’ve read his stuff for years and he talked about doing this stuff. And basically I just threw on like a 20 pound weighted vest and I would do like three to five rounds of a circuit where I was doing like some planks, which I incorporated because I’ve had a lot of back injuries over the years and I found that kind of really fixed that for me. 

And then like weighted pushups or weighted dips with the weight vest and then just body weight squats with the weight vest or maybe holding a kettlebell or something like that. And then like chin ups if you can do them, which I know not everyone can, especially with the weighted vest, but I would do like say 15 squats with like a kettlebell plus the weight vest, 10 pushups and then like five chin ups. And I would do three to five rounds of that. And the nice thing was like, as you get like lighter, all those movements get easier, which means you can sort of complete it in a faster time. So I was like tracking the time that was taking me to do this and it was maybe taking me like 15 to 17 minutes to do five rounds and eventually got that down to like eight or nine minutes to get through five rounds. 

And I would just go for a walk with the dog in the morning for like 30 minutes with the weight vest on and then just go straight to the garage to the gym after and do that workout. And I would do that like five days a week. And I felt like, honestly, I felt better than like I’ve ever felt in my life like doing those workouts. And it’s not as heavy and I don’t think you’re going to build as much muscle as you’re going to build doing like heavy squats and stuff like that, but you can make it harder for yourself just by just like trying to increase the velocity, for example, that you’re doing a pushup. If you push yourself up kind of at like a comfortable pace versus like try to really throw yourself up as hard as you can, you can make like a set of 10 pushups like way harder, you know what I mean? 

And you can increase it to up to 10 rounds or something if you really wanted to. But I found like for me, the sweet spot was like three to five, depending on how much time I had that day. And maybe on the last round I would do like more reps of each exercise and just really try to get like a pump or something. It was really awesome and I felt like it really improved my cardio too without having to do like kind of more traditional boring cardio. Well, I find it boring anyways. So yeah, that really worked well for me because it worked with the weight loss goal that I had. It kept the workouts nice and short and they’re not like super intense workouts that you get super sore from. So you can kind of do it every single day, which is good for kind of building that habit, same with like the eating. 

It’s so simple and it just, it worked really well for me.  

Rob Walling:
What I like about it is it crushes the, I don’t have time peace because that’s always for me is I don’t have time to do this for an hour or whatever. We have dumbbells up in the … We have a rooftop deck and there’s an area there where we have dumbbells and the three of us who live here now, because we have a 15 year old and Sherry and I, we share them. And so I don’t have a weighted vest, but I do similar circuit workouts that are just … And I’m breathing heavy. And again, by the time I get to about 20 minutes, I’m usually like, “Man, I’m so done with this. ” And I always feel guilty about that because I used to. Look, when I was in high school and college, I was an athlete, I ran track, played football, and I mean, I’d work out two straight hours, like four days, four or five days a week, alternating legs and everything. 

And there’s just no chance I’m going to do that. And so I always feel like a failure. So it kind of made me feel a little better of like, because I’m fine with my results, you know what I mean? Again, I don’t like working out, but I like being in shape just because I like feeling that. So I find it really fascinating because I haven’t heard anyone else talk about doing … I mean, you’re talking about doing an eight to 12 minute workout and that’s pretty amazing.  

Adam Wathan:
Yeah. I do think like the 80 / 20 on that stuff is a lot … You can get a lot more results and a lot less time than I think people think they need. And that type of workout too, you don’t need to go to a gym to do that. You don’t need any equipment except for like chin-ups or something, but you can find some … I mean, you can get a doorway chin-up bar that you can put over the trim and throw a resistance band around it or something if you’re not strong enough to do a chin-up to make it a little bit easier. And that’s basically all you really need. You’re not going to get into like competitive bodybuilder physique or anything doing that, but you’re going to be in the 1% if you’re consistent with it.  

Rob Walling:
Did getting in shape, do you feel like it made you a better founder? Did you notice a difference in your energy or your decision making, how you handled stress?  

Adam Wathan:
That’s a good question. It’s a little tricky. I think yes overall, but I’ll caveat that by saying at that specific time period in my life, I was so focused on dropping all that weight and getting in shape that it actually made it hard for me to give the business as much attention as I was just giving that mission of just trying to fix my health. For me, I’ve always struggled with eating my whole life. So the amount of discipline and sort of willpower that it took really sort of drained my battery personally. So there was kind of two elements to it there. I definitely, I slept better, I felt better, I definitely had more energy and I’m sure all that was good for me. But yeah, to be perfectly honest, for me specifically, that became like my obsession at that time. I don’t think it needs to be that way for people, but I was in a situation where I just had a problem and I just really needed to focus on solving it. 

And that became sort of my focus at that time. So  

Rob Walling:
Wrapping us up on this topic and then I’ll let you go, you’ve mentioned a couple times that you no longer do that workout style, you’ve changed. What are you doing now and why?  

Adam Wathan:
So mostly out of just like, it’s nice to do something new once in a while, but now my business partner, Steve, works with me at my house like three days a week. That’s something we started doing at the, maybe mid last year or early last year. And I have a really nice gym set up at home and he likes to train, but doesn’t do a good job of sticking to it by himself. So now that he works here with me, me and him will go down to the basement and work out in the nice gym doing real weight training with barbells and stuff for an hour, two or three times a week. And it feels like we have the time for it because we’re down there doing it together and we talk shop the whole time. And I think both of us end up coming away from that with lots of new ideas and stuff. 

It never feels like something that we’re trying to make time for. So we’ve kind of transitioned back to sort of that type of training. And I think like I do have a hard time doing it by myself. I think like that’s the other tip that I would give anyone who’s trying to like … It’s similar to doing a class. If you can find like a training partner, both of you might not feel like working out that day, but unless both of you come out and say it, you’re going to expect that the other person’s expecting you to be there and say, you know what I mean? So that accountability, I think really helps. And also just like makes it, I don’t know, maybe not everyone’s this way, but I just find it so much more fun to just have someone to chat with and to sort of … Yeah, it creates like a little bit of a competitive atmosphere. 

Not that you’re competing with each other, but it’s almost like someone’s there watching you. You want to put in some good work because like someone’s sort of observing you and you want … Yeah. So I think that’s been huge for us is just like being able to actually work out with your co-founder is awesome.  

Rob Walling:
Yeah, totally. That’s a nice luxury you guys have, that you live close enough. Well, man, thanks so much for finally coming on the show.  

Adam Wathan:
Yeah, no, thanks for having me.  

Rob Walling:
Folks want to keep up with you on X. You are Adam Wathan, W-A-T-H-A-N. And of course, if they want to rapidly build modern websites without ever leaving their HTML, tailwindscss.com.  

Adam Wathan:
And without ever leaving your terminal now-  

Rob Walling:
That’s what it is. That’s our H1, I’m just reading it. Thanks again for joining me, man.  

Adam Wathan:
Awesome. Thanks, Rob.  

Rob Walling:
Thanks again to Adam for taking time out of his busy schedule to come on the show and tell us about his experiences, both growing, tailwind labs, having to make the hard decision of letting some of his people go and about how he’s been staying in shape these past couple years. Thanks to you for listening this week and every week. This is Rob Walling signing off from episode 825. Much like the track, Her Majesty by the Beatles, the hidden track at the end of Abbey Road, this is the hidden track of this episode of Startups for the Rest of Us. In it, I ambush Adam Wathen with trivia questions, five of them. Oh God. And I’ve picked a topic that I don’t know if he knows anything about, but I asked ChatGPT to give me 10 trivia questions. We’re only going to do five of them. 

I’m going to pick them about tailwind CSS.  

Adam Wathan:
Oh God, all right. And  

Rob Walling:
I am  

Adam Wathan:
Fascinated.  

Rob Walling:
Me too. I’m fascinated. Well, sometimes ChatGPT pulls out such random crap that it’s like, what is the this? You know what I mean? It can go so detailed, but I asked it for difficulty. Normally I go difficulty one to 10, 10 questions, and then I kind of pick through and the last one is a 10. I said difficulty three to 10 because I didn’t want any gimmes, any gimmes for you.  

Adam Wathan:
Okay. No, all right. It’s going to be like, what is the commit hash of the 90%?  

Rob Walling:
Yeah, totally, totally. And you’re like, 9A, four, B.  

Adam Wathan:
Yeah. Oh, I know  

Rob Walling:
This.  

Adam Wathan:
I got a tablet too on my wrist. All right, let’s go.  

Rob Walling:
I have ambushed many a person with this. It’s always people I feel comfortable with that I like, that I’ve met in person, and so I hope you consider it a privilege and not a  

Adam Wathan:
Dick  

Rob Walling:
Move by me. All right, first question, difficulty three. And if you say these are wrong, that’s the other thing is there’s a chance that ChatGPT is just wrong. It’ll be interesting. All right. What core philosophy differentiates tailwind CS from to traditional CSS frameworks like bootstrap?  

Adam Wathan:
I don’t know how you give a correct answer to this, but I would identify, I would say the core philosophy is heavy reliance on presentational classes and building things out of tiny utility classes directly in your markup.  

Rob Walling:
That’s what ChatGPT says it’s a utility first framework instead of prebuilt components. It provides low level  

Adam Wathan:
Utility  

Rob Walling:
Classes. So nice. Difficulty four. So you’re one for one. What configuration file is typically used to customize a tailwind projects design system, colors facing and break points?  

Adam Wathan:
Yeah. Okay. So prior to January 2025, this would be your tailwind.config.js file or tailwind.config.ts or whatever. But nowadays, you configure tailwind in a CS file, which can be named whatever you want. It’s just like whatever you decide to call your CS file.  

Rob Walling:
Dude, that’s a great answer. ChatGPT just says tailwind.config.js. So you nailed it. You gave the bonus answer. You’re like, get current. Two for two, man. All right. What feature introduced in Tailwind 2.1 allowed developers to write arbitrary values directly inside square brackets, like top dash square bracket 117 pixels?  

Adam Wathan:
So there’s two possible answers. One is just the feature was just called arbitrary value support, but the thing that enabled it was our just in time engine.  

Rob Walling:
Perfect. Its answer is arbitrary value support via the JIT engine.  

Adam Wathan:
Okay. There you  

Rob Walling:
Go. Dude, it’s like you know … It’s  

Adam Wathan:
Like I made it.  

Rob Walling:
It’s like you know everything about this. Okay. So for the last two, I’m going to go to difficulty nine and difficulty 10. We’re going to go nuclear because these feel way too easy and we’ll see if we can stop you. In tailwind, what directive is used inside a CSS file to inject base styles, components and utilities?  

Adam Wathan:
So it’s at tailwind base at tailwind components and at town utilities, but that’s also not really true in the latest version. In a ChatGPT world, that’s true. Yeah.  

Rob Walling:
I love this. You are nailing this dude. Does that seem like a difficulty nine to you? That  

Adam Wathan:
Seems prettyeasy. No, that’s not. That seems very  

Rob Walling:
Simple.  

Adam Wathan:
Yeah, that’s like a getting started documentation thing. You need to type that to make it work.  

Rob Walling:
Yeah. I don’t know what ChatGPT killing me. Oh, that one’s interesting. What controversial design decision did tailwind embrace that many early critics objected to?  

Adam Wathan:
Is it just the utility class thing in general? I think that was the thing that people really just … It’s not semantic, it’s not going to be maintainable. Separation of concerns. These are the terms that would be thrown around, I think generally. Yeah.  

Rob Walling:
That’s it. The answer, writing lots of utility classes directly in HTML markup, arguing that ugly markup was preferable to context switching into separate CSS files and dealing with naming abstractions.  

Adam Wathan:
Dude. There’s no harder ones. I don’t know that ever … Okay, so the content key is where you specify all the paths to all of the files in your project that might contain tailwind classes that we need to scan through to figure out what utility classes that you’re using. But it was introduced in V2.1, not V3. And the problem that it just … I mean, that’s the thing that makes it possible for Tailwind to just produce the smallest possible output instead of being like a multimegabyte CS file that contains every single utility possible in the framework, which really slowed down development speed and dev tools performance in browsers specifically.  

Rob Walling:
So yeah, you nailed that. And it says it replaces the old purge configuration from V2 and earlier. Is that true?  

Adam Wathan:
That’s true. That’s true actually. Yep. All right. I’ll give you everything. If  

Rob Walling:
I had said, what did it replace? I think you would’ve gotten to it.  

Adam Wathan:
No, you did say that and I literally forgot that that was called that before.  

Rob Walling:
Yeah. No, that’s good. I think let’s try one more. Why can’t you use @apply with every possible tailwind utility? For example, some responsive or pseudo class variants. What’s the underlying limitation?  

Adam Wathan:
Dude, that’s a super dated-  

Rob Walling:
Is it?  

Adam Wathan:
Question. Yeah, you can.  

Rob Walling:
See, I give up. We give up. That’s it. Oh, I love this, dude. I think you’re like seven out of seven or something like that. Congratulations,  

Adam Wathan:
Man. Well, the purge one, I feel a bit of shame in getting the purge. You’re  

Rob Walling:
Like,  

Adam Wathan:
“I get  

Rob Walling:
Maybe an A minus on this test.” No, that was great, dude. Thanks for playing along. Your prize is in the mail.  

Adam Wathan:
Cool. All right. Thanks, man.