Things Worth Learning

Building a Business You Want, with Adam Wathan

Episode Summary

In this episode Adam Wathan, founder of Tailwind, shares his story about moving from working for himself to running as a company. We talk about delegation, building a culture of trust, and building & maintaining a happy and satisfied life.

Episode Notes

Episode Transcription

Matt Stauffer:
Hey, and welcome to Things Worth Learning. I'm your host, Matt Stauffer. This is a show where a curious computer programmer, that's me, interviews fascinating people about their passions.

Matt Stauffer:
Today, my guest is Adam Wathan, the creator of Tailwind CSS. Adam, would you mind telling us a little bit about yourself? Whether it's your personal or your professional life.

Adam Wathan:
Hey, Matt. Thank you so much for having me on. Yeah. Like you said, I'm Adam Wathan. I'm the creator of Tailwind CSS. And these days, I spend my time running a small company of people, maintaining Tailwind and our related stuff full time.

Matt Stauffer:
Yeah. For anybody who doesn't know, because one of their goals, Adam, that you may not know of this podcast is to make this appealing not to just people in the tech world. Tailwind is a way that people use ... So CSS is something used to style websites. So if you're going to have a website, and you want to make this thing green, and this thing blue, you use CSS. But CSS has historically been really difficult for people to ... I mean, there're certain things.

Matt Stauffer:
I'd love to hear your pitch, actually. Your elevator pitch. But it's been very difficult for people to work together as teams to have very consistent things that are also very easy for other people to maintain later. That's the biggest pitch that I've always given for it, is that no matter, whether it's me or somebody else, picking it up two years down the road, Tailwind is the thing that makes it super, super simple. And of course, it all makes it easy to get started at the beginning.

Matt Stauffer:
But I should let you. Is there an elevator pitch that you give to people? Or is that a pretty simple version of it?

Adam Wathan:
Yeah. I don't think I have an elevator pitch really. I guess I would say that, I guess, there are two different parts of working with CSS. One is knowing what all the CSS properties are, what all the features are, what they actually do when you use them and apply them to different nodes on a website. But then the more mysterious side of things, which is, I think, where everyone always tends to struggle, is how do I structure my CSS? What naming conventions do I use? What do I do to make things reusable? What should I base the names on? How many files should I have? Whatever. That's actually the really hard part.

Adam Wathan:
I don't think there's a lot of ... Well, there's a lot of people who have taken stabs at coming up with an approach for handling that side, and put together recommendations and stuff. Tailwind is ultimately another set of recommendations for how to handle that side of things in a way that I found works well for me and seems to work well for lots of other people too.

Adam Wathan:
It happens to be somewhat controversial because it seems to be, in a lot of ways, doing things the way everyone told you not to do them for a long time. Which I think, was maybe why, in my opinion, that's why people were struggling with this stuff for so long. Because there's just been this sort of off limits approach, and everyone's been trying to work in the confines of what they thought was good. It turns out-

Matt Stauffer:
Turns out.

Adam Wathan:
... that in my opinion anyways, and for what seems to have worked for me, the magic bullet has always been hiding in that off limits area.

Matt Stauffer:
That's good. If anybody's really curious about the history of this, Adam is the host of a podcast called, Full Stack Radio. The first ever episode was him describing the early ideas of this, and me being like, "No. That's terrible." I was very embedded in the old way. The OOCSS and the other stuff like that.

Matt Stauffer:
And then, Adam and I worked together during that time he was developing Tailwind and I became a convert. I was like, "Give me early access to Tailwind before it's a thing." I changed my web ... My website was one of the first websites on the internet using it because I was so, so converted from the old ways of thinking. We've been using it since it was beta and were complete ...

Matt Stauffer:
It's I just want people who don't know Adam to understand that what he has done has changed the face of designing and styling websites across the entire internet. All your favorite companies use Tailwind for stuff. So I just want to hype him up because if anybody doesn't know, Tailwind is a really big deal. Adam is a really big deal. He's a very humble guy, which I love and I appreciate, but he's a big deal.

Matt Stauffer:
Okay. Cool. Let's just move onto the question. I won't embarrass you anymore. Do you have any sort of life mantra or phrase or idea that you try to live your life by?

Adam Wathan:
I don't think I can distill anything like that down into a single Tweetable phrase or anything. But something I think about a lot, especially lately when I'm making decisions about things I'm doing and what I'm working on, is just, "Is this actually going to get me closer to the life I want? Or is this just something that I feel like I'm supposed to do because of external factors or external expectations?"

Matt Stauffer:
Yeah, expectations. Yes.

Adam Wathan:
Or what I see other people doing or how I see other people defining success. It's become really important to me in the last couple years, to really define my own version of what success in my life looks like, and make sure that I'm measuring my decisions against that and not against what I see as a more abstract definition of success in terms of the rest of the world.

Matt Stauffer:
I love that because I have joked with the last couple of guests that this podcast is a little bit therapy for me. That's certainly where I am right now. I'm 37 years old, and I'm just now getting to a point of realizing that I've been living the majority of my life according to what the people outside of me, whether it's religion or culture or whatever else it tells me success looks like or tells me doing the right thing looks like. And so, just learning that a life lived allowing everybody else to define what success looks like for us would be one that, I think, we would regret. Right?

Matt Stauffer:
Rather than, "I found what I wanted. I found what was good for me and my family and I ran for it." I love that. Thanks for sharing that.

Adam Wathan:
Yeah. Totally.

Matt Stauffer:
All right. You know that this podcast is about one topic that you're really passionate about. Could you tell me what we're going to talk about today?

Adam Wathan:
Yeah. What I'd really like to talk about today, specifically, is ... How do I want to describe this? Basically, moving from working for yourself to running a company and how challenging that is. And how to, or at least, how I am thinking about trying to make sure that while making that transition I'm still getting the life that I want and not finding myself stuck with something that isn't actually making me happy. Because I think it is way too easy to land in that position, when you're running your own business.

Matt Stauffer:
Yeah. Well, that's super familiar. I mean you and I have talked about this. Every single time one of my friends has gone off on their own, first thing I say is like, "A lot of people think that ... I don't want to work for a boss, and so then I'm going to go work for myself." Thinking that, let's say you're a programmer. That, that means you're going to go be a programmer. Solo work, yes, but the moment you start a company, you're now a business owner more than you're a programmer. Right?

Adam Wathan:
Yeah.

Matt Stauffer:
And for some people, that can be a happy life. And some people, that can't. So I'm really curious to you, what was the transition like for you? You were an employee and then you left. You just worked for yourself for a while, right?

Adam Wathan:
Yeah.

Matt Stauffer:
You wrote books and you did stuff like that. And at some point, you decided I'm going to turn Tailwind into a thing and it's going to become a company. What was the process like for you, transitioning from that to founding a company, basically?

Adam Wathan:
Yeah. When I first went out on my own, I wasn't doing freelancing or any of the sorts of things where it's really obviously why your time would be getting sucked up by things that you don't plan to do. Like negotiating contracts, and trying to find work and all that sort of thing.

Adam Wathan:
I was writing books and creating courses and stuff. Those would happen in these big sprints. And then, I would take a break and work on some interesting things or hack on some stuff where I'd ... A lot of time I'd be doing that while I was working on educational products, too.

Adam Wathan:
That was actually pretty great. I had a lot of freedom doing that, I think. That's where the first version of Tailwind came from. That's where me and Steve eventually had the idea to work on the Refactoring UI book, and had lots of fun coming up with ideas for how to teach some of that stuff, and working on other open source things, rebuilding my own personal website. All the little fun side projects I got to fill my day with, and that was actually really, really nice.

Adam Wathan:
Then Tailwind came out, and it really just took off as a tool, more than I ever expected. Because I had never really intended to even release it, originally. I was just writing it for myself, for some other projects, and I was doing some live streams where people were watching me build out some SaaS ideas. No one cared about any of the stuff I thought they were going to care about. Everyone would just ask me, "What's the CSS framework is this? What's the CSS framework is this?" So I decided to open source it.

Adam Wathan:
And then, I guess it was about a year and a half after releasing it, I decided I wanted to work on it full time. I was supposed to be starting a business actually with someone else, working on a SaaS app idea. And then, when me and Steve released the Refactoring UI book, and Tailwind was getting really popular, I decided to back out of that. Because it just felt like, "Ah, this Tailwind thing is ... There's so much potential here to really make my dent in the universe." It felt like. This was my laravel, if you're thinking of someone like Taylor, what I could be remembered for. That felt like it would be a wasted opportunity to not do that.

Adam Wathan:
So I worked on that, just full time. Getting to one point, working on some videos and documentation and adding new features. The whole while that was all being basically funded by the info products and stuff that I had worked on, like Refactoring UI, the book I did with Steve continues to be really successful to this day without us really doing anything. That gave me a lot of freedom to work on that stuff and not think about making money, which was the dream. That's exactly what I wanted, just to be able to work on the things I find interesting and not really worry about the financial side of things.

Adam Wathan:
Me and Steve wanted to make some Tailwind UI, Tailwind components, Tailwind templates. We had this idea just, if honestly, only to make the community grow and add more awesome stuff. We wanted to design a bunch of stuff, build it, and release it. It made sense to do that commercially, I think, because of course, the info product stuff isn't going to sell for the rest of time.

Adam Wathan:
Me and Steve were already in business together, and that was the perfect overlap of our two skillsets. So we started working on that. I never really had huge expectations for it. I didn't think it was going to do as well as Refactoring UI, for example. But it did way better than Refactoring UI, actually.

Adam Wathan:
We found ourselves in this position where it was like, "Holy crap. We have a lot of expectations on us right now. We have all these support emails coming in. We have issues being opened up in Tailwind. We have people wanting new features because there's so many people using it now. We have to finish all these Tailwind UI components because we erased it in early access and we want to add more. We have all of these people asking us for new designs and stuff." We just found ourselves extremely stressed to the point where we had gone from six months prior, feeling like we had-

Matt Stauffer:
This is the life.

Adam Wathan:
... open rein to do whatever we want and live life and work on fun things to releasing this product that ... I mean, in a lot of ways, I'm sure that it's just psychological, that you could just ignore the pressures and expectations of people. And just be like, "Oh, no. We did that and we've done that. And now we're just going to go back to doing whatever." But for whatever reason, it just didn't feel that way.

Adam Wathan:
It felt like, "Man, we are ... There's a lot of people counting on us now." And in a lot of ways, it felt like we were forced to turn it into a real company. Not because we actually decided, "The next challenge I want to take on in life is becoming CEO of a company and learning how to lead a team and deal with people problems and whatever." Because that, is not interesting to me at all. You know?

Matt Stauffer:
Yeah. Yeah.

Adam Wathan:
But we had to do it, it felt like, because it just felt like we needed help. It felt like, "We can't keep up with stuff. We need to figure out how to use some of the resources that we have, financially, from these products, to get other people to help us so that we aren't drowning."

Matt Stauffer:
Yeah. You actually like the life that you're living, basically?

Adam Wathan:
Yeah. That's how we got to this spot.

Matt Stauffer:
Okay. At that point, you went from the two of us are in business partnership together. And we're both just doing the thing. So even though it was two of you, it was technically a company. It was still just like a designer and a programmer who liked working together, doing some fun stuff together. You didn't have employees. You didn't have business structures. Things are different in Canada than they are in the U.S. but I assume that your incorporation was at least a little bit different.

Matt Stauffer:
Regardless, your day-to-day life was not someone who runs a business. It was still individual contributor, right?

Adam Wathan:
Yeah. It wasn't even ... We weren't even working together really every day. We started the company because there needs to be some entity that receives the money from the book sales. We talk every day because we're great friends. I mean, hacking on things together. But it wasn't like we were spending every day working on projects together.

Adam Wathan:
Steve was working on icons for fun or whatever. I was working on Tailwind features. We'd chat because we're friends and it's nice to have social interactions throughout the day. But we weren't necessarily pushing something forward together every day, all the time. It wasn't until we wanted to start working on the templates that we got focused again on working really in close collaboration.

Matt Stauffer:
When you did that, at some point you all had to make a decision, "Hey, we got this new thing. We're going to hire." Did you actually sit down and decide who's going to take what role? And you're going to do the more CEO leadershipy stuff? What was that process like of making those decisions?

Adam Wathan:
No. Not really. It just kind of just, "There's a fire. Where's some water? Let's ... We need help. We don't know what to do with help, but I think that's what we need." And, "Can we find someone?" We hired Brad, who's the first person that we hired here. I didn't know anything about hiring people. I still basically don't know anything about hiring people.

Adam Wathan:
The way we hired Brad was I sat down and I was trying to think who could we hire. I thought, "What about Brad? He does that VS code extension for Tailwind. He's probably pretty smart and he seems like he knows a lot about this stuff. I'm just going to email him and see if he wants to work here." He's like, "Yes. Sure. I want to work here." So then, he just started working here.

Matt Stauffer:
Easy. Yeah. Hiring is a little bit easier when you're such a desirable place to work. Right? Everyone wants to work at Tailwind.

Adam Wathan:
Yeah. Yeah. Well, we got really lucky there because I've learned since that it is important to be pretty diligent about hiring. But yeah, so we didn't take any of that stuff super seriously in terms of trying to do things right or figure out who would do what role. We just felt that there was so much stuff to do that we needed help. I found out pretty quickly that having help is helpful but it creates more work still. That has been probably the biggest challenge is figuring out how do you get help without it turning into more responsibility and more work, because that's naturally what happens when you involve more people if you're not very, very deliberate about creating systems and stuff for making people able to provide that help without you becoming a bottleneck for it still. That's what it feels like I've been dealing with for the last year and a half, and trying to slowly get better at and find solutions too.

Matt Stauffer:
It's funny because Tighten's been around for 10 years now, and I still think that's what I'm figuring out. Because I think I'm a bottleneck for too many things, because I want my hands in every pie, I want my influence in the culture. We just realized this year, we have an apprenticeship that was my baby, and I'm not at a point where I can give the effort towards it that I should. And they were just, gently, they were like "Matt, we need other people to be running this because we need somebody that has more time and energy than you." I was like, "Ah."

Matt Stauffer:
So what did it look like for you to begin establishing and identifying where are the structures, and where are the places where you're the bottleneck and everything? What does the process look like for you of bringing on your first employee? Because I could imagine, you could bring on your first employee and just get completely sucked up in support. So you had to make some evaluations so just what did that process look like for you?

Adam Wathan:
Yeah. Honestly, still figuring it out. But I can try and share some of the things that at some point we weren't doing, that we are doing now, that I feel like I made things better.

Adam Wathan:
I think the biggest one was adopting the shape up methodology for project planning. So for anyone who's not familiar with that, at its core, it's really just about batching your planning and putting together batches of work that are six weeks long. Where you say, "This is all the stuff you want to get done in the next six weeks."

Adam Wathan:
Then you take a two week break between each one to figure out what you want to do next, and maybe react to any issues that came up based on the work that you did in the previous six weeks. That's eight weeks when you combine the six weeks of work and the two weeks of reaction time. You get six shots of that each year, basically.

Matt Stauffer:
I was just counting them. "How many eight weeks of this do you get?" Right.

Adam Wathan:
It feels like you should have more, but you only get six of those per year, which is really focusing because it helps you figure out, "Okay, everyone has a laundry list of things they want to do in their business and things they want to release and whatever."

Adam Wathan:
If you know you can only do six of them a year, though, it really helps you prioritize. It helps you realize that you have to start working on those things sooner than you think, most of the time. And, putting them on the roadmap earlier than you think for them to actually get done when you actually want them to get done.

Adam Wathan:
The reason this really made a difference for us is because before this, we were flying by the seat of our pants. I would work with Brad, for example, to come up with a project for him to tackle. It would maybe be a four or five day thing. And at the end of that, I'd have to come up with another thing, and then that'd be two or three days. And maybe some of them were two weeks. It was just constantly, "Okay. What do we do next? What do we do next?"

Adam Wathan:
And because of that, I felt like a lot of really important things were just getting kicked down the road because the only things that we were working on were things that I could confidently hand off with five minutes of preparation, because we were planning at the last minute.

Matt Stauffer:
Yeah. You were in the middle of doing something else when he needed from you. Yeah. For sure.

Adam Wathan:
That was super stressful because I always felt like there was this ticking time bomb of, "Oh, crap. Someone's going to need direction from me soon. Someone's going to need direction from me soon."

Adam Wathan:
So by doing the shape up stuff, instead I just write up this big message for the team at the beginning of the six weeks. "Here's all the projects we're going to do this week. Here's all the information that I think we need to do them." I only give as much information as necessary because I want people on the team to have as much influence on actual solutions and stuff as possible. But I try to at least cover, "Here's the things I think you're probably going to ask me." So you just have that information right away and you don't feel blocked.

Adam Wathan:
The nice thing about that is generally, I'm basically free for six weeks after doing that. That's not really true because always things come up that decisions need to be made and sometimes you need to make sure we're prioritizing things properly and stuff like that. Because it feels like my job is to have this big picture view of everything that's happening, and whether things are happening at the right time or whether too much time is being spent on this. That, that person wouldn't really have any idea if they're spending too much time on it or not, because they don't have the full context of what else needs to get done necessarily or whatever. But that made a big difference for us because it let me reclaim some of my time back.

Adam Wathan:
Because like I alluded to, the last thing I wanted when starting a business was to become a leader. The funny thing is, I mentioned at the very beginning of our conversation how something I've been thinking about a lot lately is making sure that I'm making decisions for myself and not for some abstract idea of what I feel like I'm supposed to be doing.

Adam Wathan:
I do feel like when we first started hiring people I put on this hat of, "Okay, I'm going to be a real business owner now. I'm going to do what startups do, and I'm going to ..." I was excited about that. I thought, "Oh, I'm going to be the best boss ever, and I'm going to create this amazing company, and I'm going to be the type of guy that one day is going to write a book about how to run a company."

Matt Stauffer:
Right.

Adam Wathan:
Not to that extreme, but do you know what I mean?

Matt Stauffer:
Yeah. Yeah. I know what you mean.

Adam Wathan:
Really just embracing that or whatever. Eventually, I had this moment where I realized it was a total larp. It felt like playing LinkedIn dress up where I was just cringing at myself for even believing in my head that I was this business guy or whatever. It was just so embarrassing to myself. When I knew, really what I want to do is wake up every day and do whatever I want creatively on whatever I find interesting. And that all I really care about in terms of building a company is making my own life better. That sounds selfish or something, I think, which is a hard thing to wrestle with.

Adam Wathan:
Because I think, and I was super guilty of this too, before I started my own company, there's a lot of just attitudes that exist out in the world from people who have never worked for themselves or tried to build a business where all business owners are these fat cats who are just taking advantage of people and paying people as little as possible so they can be rich-

Matt Stauffer:
Line their own pockets. Yeah.

Adam Wathan:
... and not have to do any work. There's this very like, "Stick it to the man," mentality. That's not even remotely accurate, I don't think. I think maybe there's that's accurate for maybe super giant corporations. But even then, I have so much empathy for the CEO of Time-Warner now, that I wouldn't have had back in the day. Because the reality is, the second you stop receiving a paycheck from your boss and start receiving income from selling products, you're running a business now. Did some switch flip that automatically made you this evil person, trying to take advantage of people or whatever? No. You're just trying to, just like you're trying to have a great lifestyle when you're working for another company, you're just trying to improve your own lifestyle. You want to be happy. You want to look back on the time you spent on this planet and feel like it was well-spent and that you enjoyed it.

Adam Wathan:
So for me, starting a company wasn't about like, "My mission is to create this incredible place to work where everyone is super happy. And my job is to give this gift of creating these amazing careers for people." That's not to say that we don't do that, because of course we do that. But at the end of the day, the brutally honest truth is that, that comes from a place of, "I want people to be happy here because I need their help. And if I don't have help from people, then I'm going to be miserable because I'm going to be stressed and I'm going to be overworked."

Matt Stauffer:
Right.

Adam Wathan:
I think that's probably true of more people than we think. I don't know that, that's ... People are honest enough about that. I love the people who work here and I want them to have great jobs and we've given everyone who works here multiple raises. No one's ever asked for a raise. We give people profit sharing and no one ever asked for that. We give people two weeks off for Christmas, and no one ever asks for it. I just want this to be the best place for people. I just want this to be a company that no one ever quits because I don't want to train people again. I don't want to find people again.

Matt Stauffer:
Right.

Adam Wathan:
You know what I mean?

Matt Stauffer:
Yeah.

Adam Wathan:
At the end of the day, the outcome is the same. But I hate feeling the pressure of what I think the tech industry puts out there in terms of what a CEO is supposed to be or what a boss is supposed to be. I don't think people realize that the people in charge, running these companies, are people themselves with incredible amounts of pressure and struggles to deal with. And it's lonely, because it feels like you can't even be honest or open about any of that stuff.

Adam Wathan:
A big shift that I noticed that I'm still trying to figure out how to deal with is when I was working just by myself, or just with Steve, any problem I had, I could just go to Twitter with. Any single struggle I was having, anything I was trying to figure out, I could go to Twitter with it. I feel like I can't talk about any of the things that I'm trying to figure out publicly anymore. Because there are things like, "What's the best way to give critical feedback to someone on the team when they do something in a way that's different than you think?" As soon as I Tweet that, now everyone on the team's going to think, "Am I the one that is waiting, that he hasn't given critical feedback to?" It's just you can't be open about things.

Adam Wathan:
Even though it's not like there's anything malicious or negative or whatever, but your problems, you need to talk to other people who are in the same position as you and have more experience than you. Yeah. It's hard to even find that. I've been really lucky to even find even a handful of people that I feel like I can talk to about running a company and the challenges that come along with that. But I never anticipated how much different it would be in terms of just feeling like you can't get on your problems at the scale that I was able to do before.

Adam Wathan:
I feel like I'm rambling at this point. I don't even know how we got here or where we came from. But I feel like it's a good time to take a break.

Matt Stauffer:
No. This is fantastic. Well, I mean. Sure. Take a breather.

Adam Wathan:
I'd like to. Yeah.

Matt Stauffer:
I think that one of the really great things that you said there is, that bosses are people and owners and CEOs are people. Like you acknowledge there are certainly circumstances and often more common in the bigger companies where the CEO is making jillions of dollars and the people are mistreated. That certainly exists.

Matt Stauffer:
But when we're talking on these smaller scale things, like what we're talking about, one of the questions to ask to someone is, "Is it valid for an owner of a company to want to optimize their best life, like it is for employees?" I think a lot of the pushback against owners being able to do that is from a world in which it is considered okay for owners to do so, and it's not considered okay for employees to do so. Right?

Adam Wathan:
Mm-hmm (affirmative).

Matt Stauffer:
The employees just have to sit and do the work, and the owners are working on their stock options. But going the whole way in the opposite direction isn't helpful either. "You must endure blah, blah. And you must have these value whatever." So I look a lot at the financial independence and retire early communities. The thing that I like the most about financial independence is they described it like, "You get your job and side hustle, whatever else situation, to the point where you're more able to live the life that you want to live." It doesn't mean not working, but it means doing the type of work that you like doing.

Matt Stauffer:
So a lot of people here, financial independence retire early, and they're like, "Oh, that means you're just never going to work a day in your life." The answer for most people is, "No. I just don't want to ..." I was literally listening to a podcast last night, where she's like, "I had a two hour commute from Brooklyn, New Jersey and a two hour commute back, and I have three kids. I hate that life." So for her, financial independence was getting their finances to the point where she could work near her home. That was literally it. She didn't want to stop working.

Matt Stauffer:
And so for you, I feel like that level, you're not calling it financial independence, but you want your day every day to look like something that you enjoy, and you're working on creating a company in which every day you get to wake up and do something that actually makes you happy. Is that something that's not valid for you? No, it's totally valid.

Adam Wathan:
Yeah. It is. Yeah. That's exactly right. It's hard to achieve. I think that what I'm realizing is it takes a very, very deliberate effort or you fall into this trap of just not having that.

Adam Wathan:
Something that dawned on me in the last couple of months, is financially, I have no reason to work at this point. We've had a lot of success. I've been able to put enough money away that I can take care of my family happily for the rest of my life. But I still don't feel free, because I'm not free of the responsibility that I have to ... Yeah. I mean, I could just delete my GitHub account and make all that stuff private.

Matt Stauffer:
Right.

Adam Wathan:
And just whatever. But I wouldn't be happy with that either. I would feel like I just tarnished the thing I've worked so hard on to, again, make a dent in the universe and have this thing that helped all these people, that you can say, "I did that." You know?

Matt Stauffer:
Mm-hmm (affirmative).

Adam Wathan:
It's what are you supposed to do? If that's important to you, you have to keep it running somehow. It doesn't matter how much money is in your bank account, if you feel like you can't just shut all that down without that making you unhappy then you're stuck anyways. You know?

Matt Stauffer:
Yeah. Yeah.

Adam Wathan:
That has been brutal to deal with. I'm only just starting to try and figure out how to actually deal with that. I don't really even have an answer other than I can say some things that I've tried and some things I'm probably going to try next.

Matt Stauffer:
Yeah. I love that.

Adam Wathan:
But historically, I've always considered myself part of the team in terms of when we have projects, I say, "Person A's going to handle this. Person B's going to handle this, and I'm going to handle this." I think what I'm realizing is I need to make it so I don't actually have to do anything at the company end.

Matt Stauffer:
Yep. That's the trick.

Adam Wathan:
That's what everyone says. This is like the whole e-myth thing and this advice comes from millions of places. But I've always ignored it a little bit, I guess, because I've always thought like, "Well, that's advice for people who are in the build businesses and create passive income and sail across whatever, lifestyle." That's not what I want it to be. I want to work. I want to build things. I want to make stuff. So I never felt like that was applicable to me. I always felt like creating systems at your company to automate this robot that makes you money. That's not my goal. My goal, I'm not interested in building a business. I'm interested in being creative and building tools and doing whatever else.

Adam Wathan:
Know what? This would've been the mantra, honestly, that I should've shared at the beginning. This is my favorite quote of all time, which is from Walt Disney, actually, which is that, "We don't make movies to make money. We make money to make movies."

Matt Stauffer:
That's cool. I like that. Wow.

Adam Wathan:
That is 100% how I feel with the stuff that we work on. The only reason why the Tailwind UI templates cost money is so that I can afford to keep making more Tailwind stuff and whatever.

Adam Wathan:
I think a lot of businesses are the reverse. It's people looking for opportunities to create something that can make money. That's totally fine.

Matt Stauffer:
Yeah. Right.

Adam Wathan:
Everyone who wants to do that is in the right. They're trying to create a lifestyle for themselves. They're trying to figure out how to spend their days doing what they love and not doing a job they don't like or whatever. But for me, it's I guess in some ways, it's the same thing, because I just want to spend my time doing the things I love. It just happens the things I love are the things that benefit the company. That we're able to sell and stuff as well.

Adam Wathan:
But what I'm realizing now, I think, is the only way for me to really feel free is to feel like I can step away from the business for six weeks and come back-

Matt Stauffer:
I was just going to ask that. Yeah.

Adam Wathan:
... and have the business be better. I don't feel like that yet. But I work with a coach who helps me with a lot of this stuff. She has been harping on me for a year, to say, "I think you need to take a break. I think you need to take a break."

Adam Wathan:
Something I've always told her, which I still believe it's true, and I Tweeted something about this the other day, in reply to someone else, is that a lot of the breaks people talk about when they say this stuff is like, "You need to take two weeks off and relax and go on vacation, or whatever." But when you own your own company and when you have a family with two young kids, I feel like vacation is way more stressful than work.

Matt Stauffer:
Yes, it is.

Adam Wathan:
There's no relaxing vacation. I remember the last trip me and my wife took before we had kids. We went to just Clearwater Beach for a week. We just sat by the pool, each with a book in our hand for three hours at a time in the sun, until we felt hungry. It's like, "Are you hungry?" "Yeah, I'm hungry. Let's go walk down the beach until we find somewhere to eat." Just the most relaxing, my favorite trip I've ever been on. Right?

Matt Stauffer:
Yeah.

Adam Wathan:
I never once felt that relaxed since the kids were born.

Matt Stauffer:
No. Definitely not.

Adam Wathan:
I think it's going to be many years until we get to have that again. But anyways, what I've been talking about with my coach is, she's like, "You need to figure out how to be able to take two months off where you don't talk to anyone at the company effectively, and there's two ways to do it." I think one is to just do it and just see what happens. And maybe find out all my fears are totally invalid, and that things will continue to operate, and everything will go smoothly and things will be great. That would be awesome.

Adam Wathan:
The other option is, well maybe if you just put that on the calendar and say, "Okay, from mid-February 'til the end of March, I am just going to be off the grid in terms of what we're doing here." How does that influence what I should be spending my time on right now? That's something I've been wanting to do for six months, is put together a really comprehensive company handbook that covers basically every opinion I have about every single thing that we do here, so it's all written down.

Adam Wathan:
What was helpful to me, and this actually really made me feel like all this was more possible is the other week, I made a list of what would I define success as in terms of me being gone for a week. These are all the things that I would need to happen for me to feel like it went well. Those are things like ... I'll pull up the list right now. I'll share some specific examples.

Matt Stauffer:
Yeah. I love this.

Adam Wathan:
One is there are less GitHub issues open than there were when I left. Or even something as simple as everyone was paid on time. Or a well-written marketing email is sent out for Tailwind UI update that matches or improves on the style of marketing emails I normally write. Or a new headless UI component is added with an API that I didn't design, with great documentation that fits well with the existing documentation.

Adam Wathan:
Before I wrote this list, these were all just abstract fears trapped in my head of like, "Well, this isn't going to go well. This isn't going to go well."

Matt Stauffer:
But that won't happen. Right? Yeah.

Adam Wathan:
"This needs me. This needs me." But as soon as I wrote all this down, and I started going through the list, I felt like, "All I have to do is write a document for each one of these bullet points that includes everything that I think is important to make sure this is possible to happen without me here." That was a real shift in my mindset of what was possible in terms of being able to breakaway from the company.

Adam Wathan:
Because I don't want to not be involved, I want to work on this stuff every single day. But what I'm realizing is the big source of my stress, is I feel like I am required. That is not a good feeling. You want to feel like, "Well, if I don't feel like doing that, the company isn't going to die as a result."

Adam Wathan:
I also want to believe that the more time that I have to not be working on just the day-to-day, writing emails-

Matt Stauffer:
Operations.

Adam Wathan:
... writing documentations, closing GitHub issues, blah, blah, the more I think I can actually offer more to the company.

Matt Stauffer:
Yes. Only do only what you can do. Right?

Adam Wathan:
That and just I need time to be bored. I need time to work on things that might go nowhere. I need time to get excited about something. I don't remember the last time I was really excited about anything I did. It's all just been that to do list. You know?

Matt Stauffer:
Yes.

Adam Wathan:
Of stuff to get through. Yeah. I don't know. My goal, anyways, is over the Christmas break, I want to work on this company handbook. I want to write these documents for all the things on this list that I think will try and ensure that everything can work. And then, I want to take six weeks off towards the beginning of the year.

Adam Wathan:
I want to spend the first three weeks writing two or three songs and recording them. Something that's creative and fun but has nothing to do with programming. You know?

Matt Stauffer:
Yes. Nothing to do. Yeah.

Adam Wathan:
And just see what happens. I don't know. That's what I've been thinking about a lot lately, and some ideas that have me excited for how to hopefully-

Matt Stauffer:
I love that.

Adam Wathan:
... get a better work/life balance and stuff. But yeah, yet to see if it'll actually work. But, yeah.

Matt Stauffer:
One of the things I loved is that when you and I were talking about planning this episode is you have this desire. There's a lot of things that you're an expert on. You're like, "I don't feel like those are the things that I'm passionate about because I already know them super well. I want to talk about something that I'm still in the middle of." I really appreciate your desire to do that because you share as you learn. That's one of the things that got you most popular in the first place, is you're like, "Hey, I learned this thing. Now I'm going to teach you," as I'm learning versus you could've sat in here and talked to me about all sorts of different technical and architecture things that you know backwards and forwards and blown everyone's minds. And instead, you're willing to be vulnerable and say like, "I don't know what the hell I'm doing here." So first of all, thank you for that.

Matt Stauffer:
But second of all, I think it makes it a lot more interesting because when we tell the stories afterwards, we often forget this moment of like, "I'm not sure."

Adam Wathan:
Yeah, definitely.

Matt Stauffer:
Because we're not looking at after your six weeks, telling us about how great it was. I'm really excited for you. I mean, I didn't realize how similar states that we're in, but my executive coach has been like, "There's this book, Good to Great, and talks about how these, the most successful companies do well when the charismatic front leader is able to step away and everything still continues at the same quality level."

Matt Stauffer:
It leads me to asking these questions of what are the things I'm anxious about not going well? So I took a day off, and then I took a week off, and I'm trying to get to the point where I can take a month off. Again, just like you, I would like to spend a little bit of time on a beach or something like that. But just like you said, I miss when I was doing, recording livestream videos about some new technology I've never worked with.

Matt Stauffer:
I picked up NFTs in crypto purely because it was exciting to me. And because I was like, "This is something nobody knows. There's no documentation. I'm just going to have to teach myself. Cool. Let's do it." So I totally feel you on that.

Adam Wathan:
Something I'd actually like to get your input on, I think one of the biggest things I've struggled with and even getting to this point, and why I've maybe resisted trying to do some of these things this way is I've always hated the idea of being very prescriptive with how people work and how they work on projects and stuff. Putting together a handbook or creating systems or writing down guidelines for things always just felt like, "I'm going to make people miserable." Because who wants to be micromanaged that way?

Adam Wathan:
I think micromanagement is a different thing, but that's the fear that's in my head is the second I give up on trying to just hope that everyone feels all the confidence in the world to do things with no direction, I've succumbed to becoming this horrible company where everyone has to do things in a specific way and no one gets to be creative and whatever. I think that's totally unreasonable. I think it's just an exaggerated polarized version of two possibilities. You know?

Matt Stauffer:
Yeah.

Adam Wathan:
But what I think actually changed my mind on that, and I'm curious to see if you remember this because it's related to my time at Tighten, but I started thinking like, "Okay, well I ... What would I want if I was an employee? I would want to feel like I could do, have total control over things and make decisions on things, and do things my way and up to my standards and blah, blah."

Adam Wathan:
But then when I actually think about real experiences I've had at real companies, I think the most frustrated I've ever been at companies is when I feel like other people aren't telling me the way they want things done. You know?

Matt Stauffer:
Yes. Yep.

Adam Wathan:
I remember at Tighten ... And the funny thing is, I think I'm worse for this than the average person. And yet, now I run a company where I want to give everyone full autonomy over everything.

Adam Wathan:
But I remember when I worked at Tighten and when I worked at other places, I felt like I was always asking like, "Would you put this in this file? Or would you put this in this file? I want to do things the way Matt would do them because I want to make sure Matt's happy with it." You know what I mean?

Matt Stauffer:
That's so funny.

Adam Wathan:
When I think about that, it makes me think like, "Well, maybe putting together a handbook or creating systems is going to do the opposite of what I feared." I guess that's what I hope. I think it gives people confidence to do their work really well instead of being constantly second guessing if they're doing things the way that's expected or not expected.

Adam Wathan:
I'm sure there's a balance, but I don't know if that's something you think about much or if my memory of that lines up with your memory of it.

Matt Stauffer:
No, it does. I love that you asked it, because we're in the middle, right now, of writing more processes and I'm very anti-process because I don't want to be like, "Well, we had this ..." Dave Hicking, who works at Tighten, often calls it organizational scar tissue.

Matt Stauffer:
We had this one thing happen wrong, and now, we're going to make a process to ensure that never happens wrong again. You end up basically like with a restaurant, with signs everywhere, "Must wear shoes. Must not throw blah-blah-blah." Because of just all the things that, that happened. We don't want that kind of a company.

Matt Stauffer:
But it's funny because when you had asked those questions, there's a combination of me being like, "Yeah, I want everything to look the way I want." Also, I learned an incredible amount from you as a programmer when you were working for me. I was like, "If you only did the things I did, we would be worse off." I think you also knew that while you were there.

Matt Stauffer:
One of the things I found is that you can set the baseline, and then give people agency and trust to diverge from the baseline when they believe that it's for a good reason. So rather than them always having to ask, "What would Matt want?" Literally, one of the things what you did there was built a continuous integration service that we were joking was just Matt's code reviews as a continuous integration service. Right?

Adam Wathan:
Yeah. Sure.

Matt Stauffer:
Let's all know where the baseline of what the things are that Matt or Adam wants, so that when someone needs to ask that question, it's just very clear. It's like, "Yes, this is what he wants. These are the baselines. These are the expectations." And if you just wanted to follow the rules, you could just follow the rules. But you're a grown human being. You're able to, A, ask for these things to be changed. People know if there's a code style thing or whatever, that I implemented, and code style's simpler, but the start there, and they disagree with it, they'll just say it. They'll say, "Actually, you know what? Because of this, or oh, things have changed." I'm like, "Cool. Sounds good to me." Right? It's not as if I'm defining this as the be all, end all. This is our starting place.

Matt Stauffer:
But further, in a particular circumstance, if it depends which is true for all of programming, ends up being the answer. This one you say, "It depends. And this one depends a different way," then they just do it. They don't worry that I'm going to hound and say, "Didn't you see? The handbook says you're supposed to do blah, blah." So I think you're giving people ... The best creativity for musicians doesn't come from just playing shit. It comes from knowing how to do all the perfect chords and the perfect riffs and doing it right, and then knowing when to break the rules. I feel like it's the same way there. Setting up the basic foundations and then trusting them to know when to go from it, I think is the ... I mean, hearing it that way, does it make sense to you as someone who's been in a situation-

Adam Wathan:
No. It does. Yeah. I like that. It makes ... In my mind I'm thinking like, "Okay, here's all the answers to every question you might have. So you have it. You don't feel like stuck or that you have to ask. But if you have a better idea, like do that. This isn't here to control you, this is here to remove friction on the path to getting the thing done." That's the only goal of everything that's written down here, is it give you all the information you need to make the best decision. Not to prevent you from doing things in a different way when you know there's a better way to do things. I think that's going to be an important and powerful thing to communicate as part of this whole project.

Matt Stauffer:
I love that. We're short on time, but one last thing I want to add. It's harder for Tailwind to do this. But at Tighten, the thing that is making it easiest for me to step away is levels of leadership, which was also something I rejected for ages. I was like, "We're going to be flat. It's going to be me and Dan and the employees." Right?

Matt Stauffer:
What I discovered was, we have apprentices, we have staff or mid-programmers, we have lead programmers, we have a principal programmer. So just from a programming perspective, not even looking at the project management side or ops side, we have all these levels. And previous I would just say, "I just want my fingers in every single pie. I want to be managing everybody."

Matt Stauffer:
But now, I've gotten to the point where, for example, I used to be on every single project call for every single client and read every single GitHub pull request that came in from every project in the entire company. We have, I don't know, 30 people or something like that. I can't do that. I only stopped doing that very recently. Because it's like, "Wait a minute. We have lead programmers in place who I trust, who I know will bring a question up to me if they need." So now there's that layer of disconnect where the lead programmers know what I want or know how to do things well, much better than the staff do, much better than the apprentices do. I trust them to be like a little mini umbrella over the particular piece of the project that they're on. And so, I don't worry about having my ... I stepped away. I unsubscribed from a whole bunch of channels. I unsubscribed from a whole bunch of GitHub things.

Matt Stauffer:
But then, I was like, "Yeah, but that's only a project base." But then Keith, who used to be a senior programmer, is now a principal programmer. His job is to be the umbrella over all of them. So he now handles a lot of their one on ones and he's the one they can go to if they get stuck.

Matt Stauffer:
So again, now I can step away. And even if what we have defined is not there, they now have a person to go to, to ask those questions who's not me. So now I can step back a little bit further.

Adam Wathan:
Totally. Yeah.

Matt Stauffer:
So it's not always just about a process, it's also about trusting people. You may end up finding yourself in a place where you take one of your programmers and say ... And I don't know, because again you guys are small so that might not make sense. But something that allows you to not just put a system in place, but also sometimes put a person in a place to be able to help you with that.

Adam Wathan:
Yeah. Totally. I'm already finding that. Because I think what I wanted for the longest time, was how do I get everyone at the company to know exactly what to do all the time without being told anything. How do I just get people to know that this problem is more important than this problem? Or this problem is more important than this problem? I just want everyone to know that because I feel like I'm the only one who knows all that stuff.

Adam Wathan:
It was demoralizing, basically, feeling like I couldn't come up with a solution to that. Because I think, at the end of the day, it's just it's not totally realistic. But what I realized eventually was that, "Well, it's not so much that I want everyone to always know exactly what to do without anyone offering them any context or any direction or anything, it's that I don't want to be on the hook for all of that myself." You know?

Matt Stauffer:
Yes.

Adam Wathan:
That doesn't mean that everyone has to know everything all the time. It just means that some things I need to know that I don't have to know about. You know?

Matt Stauffer:
Yeah.

Adam Wathan:
There are a lot of things that we've, I've successfully removed myself from. Like customer support, I haven't logged into Help Scout for months, at all, which is wonderful.

Matt Stauffer:
Yeah. Love that.

Adam Wathan:
I'm trying to work towards more of those things being totally off my plate. But that was a breakthrough for sure. Realizing that hierarchy exists for a reason. In terms of just it's easier for me to have three people that I talk to and those three people have three people that they talk to than to try and make everyone magically know what's going on and what should be happening at all times.

Matt Stauffer:
You can also give those people some time and some space to take responsibility for that work and do less individual contributing. So you're starting them a little bit on the process of step away from individual contributing a little bit, be a little bit more responsible for helping other people. But not to the degree that I am, right?

Adam Wathan:
Mm-hmm (affirmative).

Matt Stauffer:
They can get a little bit of that taste without you fully putting them in a CEO role. And so, you're not just putting stuff on their plate without giving their space for it. But that means you have to be intentional about it. You have to be like, "We're doing this. There's a name. We're telling everybody this is the person you go to if you have a question about X, Y, Z." We're giving them some freedom and space and extra pay, whatever, to be able to do that thing.

Matt Stauffer:
But then now, they've accepted that as part of their responsibility. And then, now they come to you when they're stuck, which is much less frequent because you picked people that you trust to be in that space.

Adam Wathan:
Totally.

Matt Stauffer:
If you get to the point where Keith has to ask me about something, I know it's a big freaking deal. Right?

Adam Wathan:
Yeah.

Matt Stauffer:
It's very infrequent and I'm always immediately accessible because I know that Keith filters out 99.9% of the stuff.

Adam Wathan:
The other thing I think is great that I realized was a big help, which is what you're talking about there, is creating, designing things in a way such that when something requires your input, your input is requested rather than you always having this background process of, "I need to check in. I need to check in."

Matt Stauffer:
Yes. Yes.

Adam Wathan:
That will destroy you. You know?

Matt Stauffer:
Yeah.

Adam Wathan:
That's the most exhausting thing in the world is feeling that way. We've tried to create systems, a few systems here that have helped with that, I think. One of the things was a few months ago, I wrote up a post for the company that just said, and this was an expectation that I already had that wasn't communicated and no one knows what to do because it's a perfect example of one of these things, was we have a company wide, call it policy. I hate that word because it sounds like it's got all this baggage associated with it.

Adam Wathan:
But what I wrote up was like, "From now on, I want everyone at the company to merge their own pull requests." That's the rule. Because what was happening is someone would open a pull request and they would feel like, "Okay, someone else has to review this and merge it before it gets pulled in. But as far as I'm concerned, it's off my plate now, because I did my part. I put it into GitHub. It's opened. I've moved on. I'm not thinking about it. Someone else is going to get it merged in." And then, that becomes someone else's problem that they don't necessarily even realize they have a lot of the time. "Oh, there's an open pull request here? What's going on with this? Is this my responsibility? Is it someone else's responsibility?"

Adam Wathan:
So by just making it very clear that if you open a pull request, it will be opened until you click the merge button. Then it's very just it's clear who owns getting that code included into the library or whatever.

Matt Stauffer:
I love that. Yeah.

Adam Wathan:
That doesn't mean you don't get review on it. But it means if you feel not comfortable hitting that merge button, it's on you to get comfortable by-

Matt Stauffer:
Yes, by whatever steps it takes.

Adam Wathan:
... asking for input or whatever. That's changed so much. Because now I feel like, before someone would fix a bug in Tailwind and a pull request would get opened, and it would just sit there, expecting me to review it and merge it. That's not anyone doing anything wrong. That's a totally reasonable assumption.

Matt Stauffer:
Right.

Adam Wathan:
But there was just people thinking that, that made the most sense based on their context and me feeling like, "Uh, this is just drowning me in work that I don't even know that I have, that I feel like I have to be constantly polling these sources to make sure that there's no stuff waiting for me."

Adam Wathan:
But now, I just don't have to think about that. I know that if there's something that requires my input before it can be merged, someone will bug me about it because they feel like-

Matt Stauffer:
They need to do that thing.

Adam Wathan:
... their work isn't done until it's merged.

Matt Stauffer:
That's great.

Adam Wathan:
Things like that have been really helpful and I'd like to figure out ways to codify more of those things. Because I think that's one of the biggest sources of frustration running a company, is just everyone has a different idea of what the right thing to do is. No one is doing things knowingly thinking, "This is a bad way to handle this." Everyone thinks they're handling it at the best way. If you don't address those things, it can breed resentment. You know?

Matt Stauffer:
Mm-hmm (affirmative).

Adam Wathan:
That is a problem I never expected to have to deal with, honestly, as someone running a company. But it's a real one, and I'm trying to get better about that by just recognizing that you can explain that you want something done differently without it being an attack on someone. And basically being able to say, "Listen, I know that you did this, this way for reasons X, Y, Z, which totally makes sense given your perspective."

Matt Stauffer:
Yes. Context. Yeah. Absolutely.

Adam Wathan:
You know?

Matt Stauffer:
Yeah.

Adam Wathan:
"You're not in trouble. You didn't do anything wrong. But I think we should do it this way." That is less, it's harder to get comfortable with that than it sounds. At least for me, because I just don't have any leadership DNA at all. I just want to make things by myself.

Matt Stauffer:
Well, it's interesting because you do have leadership DNA. Because I've had enough conversations with you over the years, to understand that you are extraordinarily thoughtful about what it looks like for you to share and teach and stuff like that.

Matt Stauffer:
But I do think that your ... And I'm just speaking for you, but I feel like your posture towards it is you don't naturally want to tell other people what to do. You want to give them freedom. And so, you are a leader, but I don't think that you're a manager by default. I do think that learning to be a good and caring manager who respects people is really tough. Especially because the last thing, I remember when you were trying to figure out how to promote Tailwind and stuff like that, the number one thing that kept you from doing it is you're like, "I don't want to be a shmoozy, gross salesperson who's always just kind of like pitching the stuff all the time. I just want to put it out there and let people like it."

Matt Stauffer:
I feel like you probably have that same posture towards managing. You're like, "I don't want to tell people what to do all the time and be up in their space. I just want to trust them and respect them."

Adam Wathan:
100%. 100%.

Matt Stauffer:
It's a weird to like-

Adam Wathan:
I'm so afraid of telling, giving people too much input or checking in with people. Yeah. I don't know. It's tough. I think what I'm learning is that I'm like that to extreme detriment, where people would prefer more input than they get a lot of the time.

Matt Stauffer:
More, yeah.

Adam Wathan:
And learning to be comfortable with that, without feeling like I'm stepping on someone's toes has been a big challenge.

Matt Stauffer:
Yeah. One of the things that has been really validating for me is the ... I think you probably heard of the book, Radical Candor. I'm only just now reading the book. But I'd seen a Tech Talk, an article about it that was like, "Oh, that's what we're trying to do."

Matt Stauffer:
I read the intro to the second edition of the book and she said, "I wish I had not called it Radical Candor because a lot of people use that phrase to justify being assholes all the time. I'm just going to tell you whatever I feel." She's like, "My original title for the book that I didn't use because I was worried it would be seen as too feminine is, Compassionate Candor."

Matt Stauffer:
I think that you're an extraordinarily compassionate person. I think it's the candor, the lack of examples of compassionate candor that is making it hard, because you're used to people doing this, beating people over the head with it. I think that candor means ... I don't have the right dictionary definition, but just telling the truth about things. When there's a thing, just say the thing truthfully.

Matt Stauffer:
I think that for me, my goal in this type of situation is to be like, "I'm going to tell you whatever's going on and I'm going to do it lovingly, I'm going to do it respectfully, I'm not going to do it if it's not necessary. But I'm also not going to hold back on what I'm thinking."

Matt Stauffer:
So people at Tighten, who've come from other companies always feel like they have to be dancing around figuring out what I'm not saying. One of the first lessons they have to learn is if I don't like what you did, you're going to hear about it immediately. That sounds a little scary when you're boss says that. But I'm like, "You're never going to have to worry if I don't like what you're doing because you will know and you will trust." The first couple of times it happens, it gives people this confidence that, "If Matt doesn't like it, he's going to have said it." I could be six months in of anxiety and something, and then check it with Matt, and he's like, "Look, I would've told you six months ago if there was a problem."

Matt Stauffer:
I think if you set that expectation up with them, it's hard. Right? It's a new skill, but they're going to feel so respected and cared for, not like you're smooshing on them or anything.

Adam Wathan:
Yeah. I agree. That's something I've been looking into more, and I agree is extremely challenging. For me anyways. It's so natural. But I agree, it's cruel to do it any other way.

Matt Stauffer:
It's selfish, right, because we're protecting ourselves from conflict?

Adam Wathan:
Exactly.

Matt Stauffer:
Yeah, but it's not what they need. Yeah. Dan and I, both are conflict avoiding people naturally, and learning that having conflicty conversations that are uncomfortable for us it was the most valuable skill we were able learn to be better for our employees. Because it was, it was cruel to not share something with them that we knew and we were thinking about. But we didn't want to because we didn't want to feel uncomfortable.

Adam Wathan:
Yeah. I think something I always fear with that ... I mean, that's something I'm trying to get better at right now. I literally had a conversation this morning that was that. It was hard for me, even though it was totally fine.

Adam Wathan:
I always worry that once I'm doing that all the time, I'm not ... I need to balance it out because I don't want people to feel like the only time they hear from me is when something didn't go the way that I want it to. And then, they're going to hate working here and then they're going to quit and then I'm going to be sad.

Adam Wathan:
That's something I would like to figure out how to balance because I feel like giving people positive feedback is not natural for me either. You know?

Matt Stauffer:
Mm-hmm (affirmative).

Adam Wathan:
I don't know if that's common for other people or what the reason for that is. But I feel like a lot of time, it's never not genuine, but it's not natural. I feel like I'm saying something that is out of character for me. If you knew me really, really well, you'd be like, "This isn't Adam saying that."

Matt Stauffer:
This is not ... Yeah. Okay.

Adam Wathan:
Even though, of course, he thinks the work that you did was really good. It's just-

Matt Stauffer:
He's not naturally going to just say it like this.

Adam Wathan:
... I feel like I'm not being me. I don't know how to fix that because I want to be better at that.

Matt Stauffer:
That's tough. Yeah.

Adam Wathan:
You know what I mean? But, yeah. I don't know. That is a big challenge. All of that. Feedback in general is one of the things I struggle the most with as a manager.

Matt Stauffer:
Yeah. My love language is words of affirmation, so giving positive praise is very easy and natural for me, so I can't identify with that. But I can tell you one thing that after you left, that Marge did. She created a channel called Kudos, where people who are probably more natural appreciators go into share and say, "Hey, this person did this and this is really great."

Matt Stauffer:
But I found being in an environment where that kind of appreciation is named and shared and done on a regular basis actually makes other people more likely to do it. So you may find that creating structures and spaces for people to share that, where you're not always necessarily the one doing it, will first of all help the company environment, but also helps maybe make it easier for you.

Matt Stauffer:
But you could also just say ... Set a Friday reminder that says, "Every single Friday ..." My kids' schools do this. Shout out somebody on something that they did really well that week. It just becomes a Friday thing, so it's less like, "Oh, Adam's doing something really weird right now." And we're like, "No, Adam has set up a thing where he's intentionally defining a culture of appreciation at this company. And every Friday, he's going to tell about something that somebody did well." So it is notably structured. It's not going to be like, "Oh, he's doing this really freaking awkward thing."

Adam Wathan:
Interesting.

Matt Stauffer:
But it's structured in a way that is nobody would every doubt that you believe the things that you're saying. You know?

Adam Wathan:
Yeah.

Matt Stauffer:
And then, you don't have to remember it. It's not a pressure that you have to remember to do sometimes. Every Friday, a reminder goes off and says, "Go give somebody kudos."

Adam Wathan:
Yeah. No. That's a great idea. Yeah. You know what? This is tangential but it makes me think of, I think in general, in life, I've always had a hard time complimenting people. That it's just been unnatural for me. I don't know why that is. Just my experience growing up or whatever, just always felt like honestly, more natural to me to put someone down than to say something nice. Because you're a kid in school, and it's you can get everyone to laugh and think that they like you because you said, it's a mean joke or something stupid like that.

Matt Stauffer:
It's rewarded.

Adam Wathan:
I still carry that with me as an adult. But I think one of the things that is stressful for me as someone running a company is it feels like if I openly say something, I feel like I'm not good at giving positive feedback and that's something I struggle with. My fear is that someone's going to say, "Well, if you don't have that skill, you have no business running a fucking company. Who do you think you are? Blah, blah. Leaders are supposed to be compassionate, whatever." It's like, "I didn't want to fucking run a company, I just wanted to make a CSS framework. I was forced into it." You know?

Matt Stauffer:
Yeah. I just want to tell you directly, I don't think you have to be a particular type of person to run the company. I think everybody should have space to run companies because we can build systems and structures that help us, and we can also bring in other people.

Matt Stauffer:
I wasn't the one who made the Kudos channel. I do have an easy time giving compliments to people. But I also think that Marge brings about aspects of our culture. When Marge joined, her job was Operations Coordinator and Content Manager. Right now, we're reworking her role to be more around people because that's what she's really, really good at. Right?

Adam Wathan:
Yeah.

Matt Stauffer:
It's not that I am really good at running onsites. Marge and Anna run great onsites, and that's okay. But I hired them and I give them money and approval to do so. I think anybody who would say, "If you don't have every particular skill that you need to run the company ..." No, that's why you hire people, to do the things ... It's not just to do the things that you already did well, and step away, it's also to do things you don't do well. I am ADHD as hell. I managed our projects at Tighten, okay. But now we've got Dave and Jean and they're like Type A, got everything under control, super structured people and it's way better than it was when I was doing it. Right?

Adam Wathan:
Dave probably has an omni focus tattoo.

Matt Stauffer:
I'm sure he does. Yes. And there's probably one on the other arm. Yeah. Absolutely. Right? That doesn't make me a bad manager because I'm not good at being as structured as they are.

Matt Stauffer:
If I was the one doing that job, then it would make me a bad manager. But recognizing that I'm not naturally good at it, and then helping other people, making space for me to be better, and then helping other people to have space to do it, that's part of leading well.

Matt Stauffer:
So anyway, anyone who told you that or that voice in your head, screw them. You're doing a great job, man.

Adam Wathan:
Thanks.

Matt Stauffer:
I have had enough conversations with you as you have been struggling through how to handle the things that aren't easy and natural for you to be able to say that very truthfully. You're doing a fantastic job and anybody would be lucky to work for you. Which is why, when you guys have job postings, you're completely bombed with everybody wants to work there because they know it's going to be a great place to work.

Adam Wathan:
Thank you. I appreciate that.

Matt Stauffer:
Yeah, and I mean it. I want to talk for hours more, but we're so far passed time. So I'm going to ask you the last question. And anybody who's curious about this kind of stuff please follow Adam on Twitter. Even though he doesn't talk about this stuff as much, and I'll give him the chance to plug in Twitter, there's still just so much of your personality and your presence available, and your online presence is, I think it's something that's good for everybody to have.

Matt Stauffer:
Last question, what insight or support did you either receive or not receive but need when you were younger that you hope more people will give to others? (Silence).

Adam Wathan:
I don't know if this fully fits in that category. But when I think about my experience growing up and how it was maybe different than other people's, and how it helped me get where I am, I was really fortunate to be in a gifted education program my entire time that I was in school.

Adam Wathan:
The thing that I remember most from that is we, for four years, I think it was grade five, six, seven and eight, when I was really in those totally full time program. Every single Friday was this thing called Negotiated Learning Day, where you would define a project that you made up. We'd do two projects a year, I think. We'd make up some project, whatever the hell we wanted. It could be literally anything. You pitched it to the teacher, and they always said, "Yes," or helped you scope it down or refine it or make it better or whatever.

Adam Wathan:
Every single Friday, we got to work on those projects in a different room in the school with no adults in the room the entire day.

Matt Stauffer:
Wow.

Adam Wathan:
Doing, working on it ourselves. Defining our own progress and doing whatever we wanted. I think if I didn't have those experiences growing up, where I was given the freedom to create, I don't think there's any chance that I would've landed where I am now.

Matt Stauffer:
Wow.

Adam Wathan:
And even in high school, when we were still in that program, we were given two weeks to stay at home and work on something ourselves.

Matt Stauffer:
Wow.

Adam Wathan:
Didn't even have to come to school. Miss every class for every other course, whatever.

Matt Stauffer:
Wow.

Adam Wathan:
I just really believe that there's so much power in giving people permission to focus on the things that they're really naturally interested in and not force them to spend time on things that they don't care about.

Matt Stauffer:
That's so cool.

Adam Wathan:
That's something I think about a lot now that I have kids, and how to make sure ... Because I can't guarantee that my kids are going to be in a program like that.

Matt Stauffer:
Right.

Adam Wathan:
I don't know how to solve the problem, but it's something that I think about a lot, is how do you double down on people's interest instead of forcing them to focus on their weaknesses.

Matt Stauffer:
I love that.

Adam Wathan:
I think it's natural to tell people, "Okay, well you got a C in this class. Well, that means you have to spend all your time studying geography because you got a C in it." But if you got an A+ in programming-

Matt Stauffer:
Then go spend less time in it. Right.

Adam Wathan:
... or an A+ in music or something, you don't need to spend as much time on that. Right? It's like, "If this kid got an A+ in programming, then we should be signing him up for a programming club that he could go to on the weekends." Not signing him up for geography tutoring.

Matt Stauffer:
More geography.

Adam Wathan:
That's my opinion anyways. I feel like I got a lot of that support when I was a kid, and got to spend a lot of time doing the things I was really excited about. That created this natural maker attitude.

Adam Wathan:
That I meet so many people now who don't have that. I have to believe those differences in how we were encouraged in school and stuff must've contributed to that. I don't know if that totally fits what you're asking.

Matt Stauffer:
Yeah. Totally does. It's amazing.

Adam Wathan:
But that's what I think about a lot. Yeah.

Matt Stauffer:
And for any parents who are interested in that kind of stuff, that's the foundations of Montessori. The problem is, at least in the U.S., is you can't get Montessori without paying for private schools. Is that even something have you heard of it before?

Adam Wathan:
Yeah. My daughter's in Montessori School here.

Matt Stauffer:
Oh, there you go. See, you already do it.

Adam Wathan:
Yeah. They literally only do it until kindergarten. And then after that, I don't know what she's going to do. But yeah, it's the same thing. One thing I've talked about, this is my dream. I don't know if I would actually find this that fun, but if I was ever going to be totally done with running Tailwind as a company and doing all that stuff, I dream about the next phase of my life being creating a private education stream for people who want to be involved in things like this.

Adam Wathan:
Sometimes I dream about, should we rent a Tailwind Labs HQ in downtown Kitchener or something? Because me and Steve only live 25 minutes away from each other. Rent a building that has a top floor where me and Steve can work and a bottom floor where me and Steve can both drive our kids to work with us in the morning. And we hire two teachers and they are down there and they believe in the same thing that we want.

Matt Stauffer:
Oh, my gosh. That's cool. Yeah.

Adam Wathan:
Find other parents who want to do it, and ...

Matt Stauffer:
That's amazing.

Adam Wathan:
I don't know. That actually gets me pretty excited, the idea of trying to give that opportunity to more people. It's a miracle that I even had what I had because the government paid for a taxi to pick me up at my house and drive me to school every day.

Matt Stauffer:
Wow.

Adam Wathan:
Because my parents didn't have money, we're immigrants from the UK, who moved over here, my dad to work as a CNC operator or machinist, and my mom didn't work, and then she worked retail. The fact that I even got to take part in that at all is crazy.

Adam Wathan:
I have a lot of skepticism around the public education system that most people go through. I can see myself getting more excited about spending time in that, in the future.

Matt Stauffer:
That is really interesting. I am really looking forward to hearing more about it, if that's something you do. I've got young kids and they're in the public education system, but one of the things I did was, when we moved to Atlanta, I spent months researching what schools I wanted to put them in. I picked everything around the schools. Because I'm like, "There's so many other things we can work around. We can live in a smaller house. We can ... Whatever. But if I can't get them this educational experience ..." And of course, lots of parents are that way. But you really want to set them up well, and we can recognize, like you just did, how much those experiences ... My kids are at school more than they're with me every day. Right?

Adam Wathan:
Yeah.

Matt Stauffer:
That's a pretty freaking important thing. But I'd never even had the imagination that you're having here. That's really cool. I know we're super late and I'm sure you have work to get to, but this was freaking fantastic.

Matt Stauffer:
So if people they want to follow you, if they want to support you, if they are interested in Tailwind, or if they're just interested in the way your brain works, what would be the best way to follow you?

Adam Wathan:
Yeah. You can follow me on Twitter @AdamWathan, check out Tailwind CSS at tailwindcss.com. We just did a big major version released last week with a big, new website and stuff like that.

Matt Stauffer:
Love it.

Adam Wathan:
Yeah. That's it.

Matt Stauffer:
Full Stack Radio.

Adam Wathan:
That's where I am these days.

Matt Stauffer:
I know that they're not making new stuff right now, but if anybody's interested, fullstackradio.com has what? 150 episodes or something like that?

Adam Wathan:
Yeah.

Matt Stauffer:
Lots of really good stuff in there.

Adam Wathan:
Lots of content. I'd like to keep doing that occasionally.

Matt Stauffer:
Good. Okay.

Adam Wathan:
I think there'll be a couple of episodes a year, sort of thing.

Matt Stauffer:
Yeah. Just when it comes up just do it. Yeah.

Adam Wathan:
Just when interesting opportunities come up.

Matt Stauffer:
Well, definitely, if you're into it, especially as a programmer, but even if you're not a programmer, there's some on there that ... Just skim through the episodes and look through which titles would make sense, but it's a lot of really great stuff. I will be very direct and honest that Full Stack Radio is very much an inspiration for making this show. Because I was like, "I want to sit with fascinating people who ..." I just wanted the excuse to talk to people who I admire. So thank you for all your inspiration.

Adam Wathan:
Cool.

Matt Stauffer:
And thanks for hanging out today, dude. This was a ton of fun. I do think that I and everyone else is going to learn a ton from it.

Adam Wathan:
Awesome. Thanks, man .

Matt Stauffer:
All right. For the rest of you, until next time, be good to each other.