Love, Passion and the Power of “Why”, with Ryan Carson

Love, Passion and the Power of “Why”, with Ryan Carson

Love, Passion and the Power of “Why”, with Ryan Carson

My guest today is Ryan Carson. Ryan is a longtime entrepreneur who has built four startups, two that got acquired, one that went down in flames, but provided a lot of learning, and a fourth one called “Treehouse,” which is currently doing about $15 million in revenue annually.

Treehouse is an online tech school with about 80,000 enrolled students. Their goal is to take people from zero to job-ready and to teach them how to code, amongst other things.

He was voted EY’s Entrepreneur of the Year, and he’s been a guest on some of the top podcasts, shows like Entrepreneur on Fire, Mixergy, This Week in Startups, and Bloomberg’s Game Plan.

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He’s doing some awesome stuff, but Ryan popped onto my radar because he’s a longtime DREAM THINK DO-er. Like many of you, he reached out a number of times to offer some encouragement and some feedback. After Episode 171, specifically, he sent an email about the five-minute moment concept.

We started going back and forth on that, how it was working for him, and that opened up a whole new subject on the power of “why,” and how being clear on your “why” makes all the difference.

Welcome to the show, Ryan!

Thank you so much.

This is fun. It’s weirdly like a family reunion, but this is the first time where we’re actually talking, so I love it.

I want to talk about the power of “why,” because I know it’s something that’s really helped you to get on track with life and career. But I want to go back a little bit and talk a little heart and head stuff first.

We have a lot of entrepreneurs on DREAM THINK DO. We’re all about helping people get clear on their dreams and goals – so one of the things I wondered, did you always want to be an entrepreneur? Was that your dream as a kid, or was that something that that hit you later?

No. It’s kind of strange. I hear these stories from other entrepreneurs about selling lemonade to their friends in fourth grade and buying bubblegum in bulk so they could then make a profit on it by selling it to their friends, and I didn’t do any of that. This is why I’m excited to talk about my “why,” because the truth is, I’m not really an entrepreneur. I’m someone who is motivated to get a specific thing done in the world, and I’ve realized that building a business to accomplish that is the best way I can do it. I’m not one of those guys that stares at spreadsheets and obsesses about growth.

Right, so for you the entrepreneurial journey is more of a means to an end as opposed to an end itself.


That’s a great insight.

I’m extremely mission-driven, so I can’t wait to kind of dive into that more.

Great. Now, this is somewhat of a loaded question, but I have to ask it. You’ve got three startups that anyone would define as successful. I mean two got acquired. One is rocking, right? And one went down in flames.


I don’t know of an entrepreneur that doesn’t have one of those stories, but what would you say? Which of those experiences helped you the most in getting clear on why you were put on the planet?

I think the failure was the most transformative. I was born and raised in Colorado and actually started off in a very religious home. I’m not particularly religious now. My parents did a really good job of driving into me that people are the most important thing in the world, and serving people and making their lives better is the highest possible calling. I continue to believe that. People are people and stuff is stuff, and I try to keep that really clear. I have some nice stuff now, but it has nothing to do with what’s good, or what’s right, or what makes me happy. So I had this upbringing, and I actually thought I was going to be a pastor for a long time.


I thought, “I love people, I love helping people. Gosh, if I can serve people like that, that sounds really rewarding,” so I was going down that path. I ended up studying computer science in college, but the plan was always to end up serving people somehow. I applied to one college, Colorado State, which was basically the local college. It’s even funnier. The reason why I applied was that my sisters went there, so it was literally like, “Well, my sisters are pretty cool, so why not?”

It worked out for them. Why not?

So I went there, and I enjoyed my experience. This was ’96 to 2000, and the internet was becoming…a thing. I remember checking my email for the first time and seeing websites for the first time. The whole time though, I believed that I had to figure out a way to make people’s lives better. Maybe that would be by leading a church. Maybe it would be by building something to make people’s lives better, but it had to be attached to that.

Then I thought about how I had never lived outside of Colorado. So I thought I’d roll the dice and see what happened. I watched the movie Notting Hill around this time…

Oh, I love that film, yeah.

Exactly. Hugh Grant and Julia Roberts, right? It’s funny because there are two classes of men in the world, I would say. There are men who appreciate romantic comedies, like me and you, and there are men who do not.

It’s true. It’s very true.

I watched it, and I thought, “So, Hugh Grant’s life looks pretty amazing.” And I said, “I’ll move to London.” Boom.

I think one of my strengths in life is also one of my weaknesses, which is I am naively optimistic, and I’m just prepared to try anything. I was raised by parents who love me, who supported me. I wasn’t afraid of just surviving as a kid. I had a foundation where, pretty much, I could try anything. So I was able to just say, “Who cares? I’m going to move to England, and the worst thing that could happen is I’ll move back or whatever.” So I bought a plane ticket, and I remember my mom cried so hard, and I was like, “Mom, what is the deal? I’m just going to go for a year. Come on.” Of course, she knew the way that the world works and the way life works, and it turns out I stayed there for 12 years.

Because you met a girl.

Exactly, I met a girl, so just like in Notting Hill, but not.

Anyway, all of a sudden, I live in England. I really care about people, and I want to make the world better, and I understand technology, but now what?

Yeah. How do I put all that together?

Yes, and I was like, “Well, the path of least resistance is being a web developer. I mean I can literally do that. It’s easy. It’s high-paying.” So I did that, and it led to my first company, which was very simple. The idea was, “I need to send large files. I can’t send them through email. It’s a really dumb problem, and I’m actually not passionate about it at all, but it is a path to freedom. I could run a little company. I could try to make a go of it. It doesn’t tick, really, in my box of helping people or a deep why, but it’s kind of the next practical step.”

I think that’s kind of a theme in my life is what is the next viable practical step here? I try not to overthink it too much. It was perfect timing because Jill and I, we had met, fell in love, and I had been working for this web development company, and we decided to get married.

I was living in London, not like Hugh Grant! Jill lived in Bath, England, and she actually had a successful career as a magazine editor. She had this kind of cosmopolitan kind of sexy life, and I was this nerdy web developer.

So it was just like Notting Hill. This is great. I love it.

Let me pause because I do have to tell the story of when we actually met for the first time, because it is a little bit like a movie. I had been doing web development stuff. I had started to build this meetup called By Designers/For Designers. The idea was very simple. There were no social networks. There wasn’t really a way to find people like yourself and encourage each other. I enjoy empowering people, so let’s get people together like me, and let’s talk about our work, and let’s encourage each other, and let’s just go to a bar and talk about web design and web development. We started doing it, and it grew and grew, and we actually called it Creative Fight Club.


Because, like the movie, anyone can run a fight club, and they’re kind of independently run.

I love the fact that we’ve talked about Notting Hill and Fight Club. I think we can check off the manly boxes now. We’re good. Okay.

Yes. I feel a little better now.

I was running this, basically, underground community in my free time. It was just kind of right thing at the right time, didn’t make us a dime. It started getting big, and things started happening all over the world. We built a site for it, and it got kind of big. Eventually, her magazine noticed. She was running the biggest magazine in Britain at the time, about web design. It was a big deal in our industry. It was the magazine. I read it every month, and I got an email that said, “We want to interview you about this thing you’re doing,” and my head fell off my shoulders, basically.

We did the interview, and that was great. I talked with the reporter about how we really needed to start raising money for these events. Would the magazine sponsor them? He told me to ask the editor. So I got all nervous and scared. The editor is super-important. Her name was Jill, and I said, “Would you be willing to sponsor our event? It’ll be a great opportunity for the magazine.” She wrote back and said, “No.”

It was love at first sight, obviously. Yeah.

She said, “We’re not going to spend money on that, but as an editor of the magazine, my job is to keep a pulse on what’s going on, and it would be good for us to meet, so next time I’m in London, let’s have a coffee.” Again, my mind blew up like, “Holy cow.”

Right. What does that mean?

This super important editor wants to meet with me. It’s the biggest meeting of my life, but I didn’t know much about her. I didn’t know she was this super attractive woman, that she was single – because you couldn’t really Google anybody back then.

Right, right, yeah. You didn’t have social media to stalk people legally.

So we set up a meeting for coffee, and I was sitting there super nervous. I was there early and making sure I paid attention and didn’t miss her. The door opens, and this beautiful woman walks in, and she’s holding the magazine, and I thought, “What is going on?”

She was so beautiful and I had to pick up my jaw and stay professional. This was a really important meeting. And the funniest part is, because I was kind of a nerd, I had a Palm Pilot, and back in, this was what, 2001, you could buy this foldable keyboard for your Palm Pilot.

Oh, yeah. I remember. I remember.

I’m like, “I’m going to be super cool. I’m going to get on my Palm Pilot. I’m going to attach my foldable keyboard, and I’m going to take notes while we meet.”

“And she’s going to be so impressed by that.” I was being all professional and taking notes and everything. Then, at the end of the meeting, it’s like 5:00 p.m., and she’s like, “Oh, you know, do you want to go grab a drink?” I was thinking, “What does that mean?”

Yeah, right. Wait a second. My nerd brain is not going to compute.

So are there signals, no signals? I could not tell. We walk to this little bar, and we have a nice chat and a bit of laughing and nothing crazy at all, and it went well. By the end, I’m thinking, “Holy cow. I think I like this woman. I don’t know what to do about this.” Anyway, so I walk her back to the tube station, and then it’s like, “Oh, man. Now do I shake her hand? Do I hug her?”

So, awkward hug. It was the most unromantic thing ever. Then I think I emailed her back and, basically, didn’t give up kind of pursuing her and, eventually, we did go on a proper date, and she said to me, “You know that stupid keyboard that you pulled out? I mean that is just the dumbest thing I’ve ever seen. I almost didn’t want to talk to you ever again after you did that.”

Here you were like, “I’m going to drop a bomb here. Check this out.” I love it. I love that story.

When I first started doing the podcast, I started doing it, like you say, to help people. I thought maybe it could help my business a little bit, but it was mostly about reaching more people this way. I look back on that and realize, “This is one of the best ways to meet freakishly cool people on the planet.”

And here you were creating a Fight Club-esque community, which in and of itself is a win, right? I mean you weren’t making any money, but your network was expanding exponentially.

But then also get to meet the love of your life, thank you very much, right?


I’m guessing it probably didn’t make you a lot of money, but it probably didn’t cost you a lot of money, either, a relatively low risk amid everything else you were doing, but what a great story of reward on many levels of Disney-level romantic comedy ending kind of stuff.

I want to segue into talking about the “why,” because I know that when we started going back and forth on this subject – I believe in the power of the why. I mean, if you know your why, the how will come, right?


I believe in that, but I know you started sharing how important the “why” was for you to be able to stay with it, and your tenacity. In your own words, why was it important for you to figure out your “why” when it comes to your current work and your life?

All right. Yeah, it is the deepest part of my life, so I want to dig into it. This journey, meeting Jill, starting a company, having that company fail, it taught me that I need to build something that is going to make the world a little better. It taught me that there’s a deep, deep part of me that feels this is the only reason I am on this Earth, and so I’ve got to do something that connects to that.

The moment that it became clear to me was when I realized my 4 year computer science degree had nothing to do with my job. What the heck is that about? Because if that’s true, it means that millions of people are missing opportunities. They are being kept out of success. They don’t have the knowledge-base and can’t get these high-paying jobs in tech, and something is fundamentally morally wrong with that.

It just bugged me, and it was just a seed in my mind. It’s not like I woke up and bolted upright and said, “Treehouse.” It was just like, “Hey, something’s wrong here, and I think it’s morally wrong. People should have equal opportunity, and they don’t,” and so it bugged me.

My first business had nothing to do with that. The large file business was kind of a disaster. It didn’t work. I wasn’t passionate about it. Then I saw a friend of mine named Jason Fried who runs Basecamp now. They just kept talking about how they built Basecamp and how they had solved a problem by building a simple app, and charged monthly, and it was transformative. Then they did a workshop, and it was called “How We Built Basecamp,” and I thought, “Wait a minute. They’re essentially teaching people how to change their life by teaching them technology. That’s really all that is.” And because I did this crazy designer Fight Club community thing, I have a crazy network. I actually know everybody in this web design industry. I could ask one of them to teach a class, and that class could give people skills to change their life, and so why don’t we try that? Why don’t we try to do that? That was the beginning of actually doing something about my why.

Then you fast-forward, and you iterate, and you iterate, and you fail, and you iterate. We’ve been through countless things where I have been so discouraged that I’ve doubted to the bottom of my soul if I had what it took to do it. The thing that kept me going was that I went back to the why. The reason why is that if I give someone the ability to create technology, they can change their life, and that just drives me.

I had one particular instance that really was transformative in the past year. We had had a company come inbound and say they wanted to buy Treehouse. I always have those conversations because you learn a lot. At some point it may happen, maybe not, but it’s always worth talking about it and seeing what happens. So we were having this conversation, starting down this path and considering it. It was, theoretically, a great strategic partner and would allow us to reach more people, and that’s the whole reason. That’s my “why,” right?


So we were pretty seriously considering it, and then in the end, it didn’t work out. There were a lot of reasons why. What was fascinating though, I had a conversation with the CEO. I told him over the phone, “I’m really sorry, but I just don’t think we’re the right fit, and I’m just going to carry on my path, and you carry on yours, and I wish you the best.”

And he said to me, “We’re going to crush you.”


And he went on: “Just wait. This is a massive mistake.” No one’s really said that to my face before.


I remember thinking, “Huh.” Thankfully, I was able to keep my composure, and I just said, “I wish you the best, and I’m sure you’ll build a big business without us. I’m sure we’ll build a business just fine, and best of luck.”

At that moment, I realized that all the things that I thought that business was going to do for Treehouse because I couldn’t do them, I had to figure it out. I couldn’t rely on somebody to learn to fix something that I thought I couldn’t do. It was transformative. Then I realized if I really, really believe in this “why,” I have to figure this out. So I began waking up at 4:30 every day and to say, “I’ve got to work really hard, and I’ve got to figure this out. It’s on me. Just because I believe in my “why” doesn’t mean it’s going to happen, and just because I believe it’s moral and good doesn’t mean it’s going to happen.

It was really transformative. I’m working hard, and I don’t compromise my family time, so I wake up at 4:30. I work on Treehouse from 4:30 to 5:45, do a quick workout from 5:45 to 6:30, and then I bring coffee up to my wife in bed, and we have a little chat, and the kids try to wrestle me and get in the way. Then I go to work at 9:00, and I work my behind off until 6:00, and then I turn it off.

That’s awesome.

I just recorded an episode of the podcast recently. It’s all about the concept of post-traumatic growth.

It’s a term that has been around since about 2004, but I wasn’t aware of it until recently. Post-traumatic growth is basically that growth that happens on the other side of trauma, some sort of challenge that you have to push through.

It talks about how the brain actually changes and develops in a way that you can’t go back to your previous self.

That’s exactly what happened to me.

Exactly right. I think we’ve all experienced it, but I had never heard that term before. You’re on the other side of post-traumatic growth, right? You’re experiencing post-traumatic growth. I always say there’s usually scars that go along with the trauma, but those scars can then also be great reminders of making it through, and kicking butt.

I can hear the “why” in your voice when you talk about Treehouse. Some people might say, “Well, gosh. People not having access to that kind of education, that’s a bummer,” right? Where you made it a moral imperative. I heard your heart rate increase when you started talking about it.

What would you say if somebody came up to you and said, “Ryan, I know getting clear on your ‘why’ helped you.” How would you suggest to the person if they said, “Teach me. Teach me”?

I would invite them to start paying attention to the moments where you smile. That happened for me when I did that first in-person training workshop where we were teaching people technology. People were walking up to me and smiling and saying, “Thank you. Thank you for teaching me.” I just thought, “Well, that’s weird. You just paid me a bunch of money. I’m kind of surprised you’re so thankful,” and it clicked, “Oh, my gosh. They are happy because I’ve given them knowledge.” That excites me, so pay attention to those moments where you smile and you didn’t mean to. That’s one thing.

Well, also, in that example, look at those areas where maybe you’re making someone else smile.


Obviously, you were smiling, but also because of something I did, another person smiled.

That’s a good call. You are right.

Part of this transformation I went through when that guy said he was going to crush me: I realized I have to get really good at sales. I always thought I was terrible at sales because I like making people happy. But being good with people – wanting them to be happy and solve a problem –that’s sales!

I believe in what I’m selling. At Treehouse, we teach people technology so they can change their life. I literally believe that’s my “why.” I think listening to people about what they constantly say that you seem to be naturally drawn to or good at, there may be something there. Those are the two things, look for other people smiling or you smiling, and then listen to folks when they give you feedback about things that you’re naturally good at.

I love that. It’s interesting. I talked with a buddy this morning, Adam Carroll, who’s also been a guest on DREAM THINK DO. It’s the total complement to what you’re saying – listen as people would give you a compliment and also receive it.

All right, so I love that. Looking at where am I smiling, where am I maybe creating smiles in others, what’s that feedback from other people, what do people naturally say that I’m good at, what have I seemed to excel at naturally, those types of things, that’s a part of it. I’m also guessing look for those places where your heart races.


Now let’s talk about how you stay there and how you continue to stay reminded of your “why.” What are some of the things you do on the good days and on the sucky days to remind yourself of your why?

Yep. Very simply, I wrote down my why: to bring technology education to as many people as possible so I can change their lives. Then what I would do is I would read it every morning. It’d be the first thing I would do when I get up at 4:30, and it was almost a ritual that would just drive it home. The other thing I would do is I would listen to music. I think music is a powerful, powerful way to alter your feelings. I found a couple key YouTube videos. One guy I absolutely love is Eric Thomas, and he’s got a couple key videos. Some people may make fun of folks that are motivational, but if you’re willing to admit that you need encouragement sometimes, then you can access that and use it.

So true. I love what Zig Ziglar talked about. He said it always amazed him that people would kind of poo-poo the idea of needing daily inspiration, but yet have no problem with the idea that we need to shower daily. He’s like, “For the love of everything holy, do both.” Right?

And with music, I’m with you. It’s amazing what music can do. I’ve got a couple of playlists that I listen to, man, when I want to change my mood, when I want to feel awake, alive.

I mean so, literally, I wake up at 4:30, and the first thing I do is I put on headphones, and I turn on either Spotify or YouTube, and while I’m walking downstairs, I listen to crazy dance music.

So true, and what I love about something like that is it’s immediately implementable, and it’s one of those things that we can do it, but it’s almost in that category where it’s so simple it would be easy to dismiss. Right?

Yeah, yep.

But at the same time, and I’m sure, DREAM THINK DO-ers, we’ve talked about this before. Many of us are tempted to wake up and immediately check social media, email – get on that smartphone. If you’re tempted to do that, why not counter it with something more powerful like a specific playlist, right?


Why not get yourself jacked walking around the house, whatever, eating breakfast and getting ready with the right kind of music. I love it.


Well, I knew this was going to be an awesome conversation, but I had no idea about the Notting Hill … and the Fight Club connection, so that … It’s even better than I thought.

You never know. Thanks. It was fun.

I love what you guys are doing, and I just think it’s a great thing, but I also … I would love to talk with people who have found the thing that helps to make them passionate, and I know Treehouse is going to continue to be a huge success.

I also know that, no matter what, in 20 years you’re still going to be walking out your passion. It’s just going to continue to evolve, right, because you’re clear on it. So even though it might have different iterations, this is something you’re going be able to walk out the rest of your days.

Awesome. Thank you.

How can people find out more about you, Ryan?

Best thing to do is hit me up on Twitter or Instagram. It’s just @ryancarson, one word. Then, if you are interested in learning how to code, just go to

Well, keep bringing the awesome, brother.

I’ll do my best. Thanks so much. It’s been a blast.

All right. I hope you enjoyed that conversation as much as I did.

Let me know what stood out to you.  Leave a comment. I can’t wait to hear from you!

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