Ryan Carson with Shane Mac

Alright, hey there.

We have Ryan Carson here today. He's the CEO of Treehouse. And Ryan, thank you for joining us.

Nice to be here. It's an honor. Thanks.

Alright, so I've read a lot of your stuff and I love your kind of different stance on building a company, on doing things a little different, on creating a culture. And a lot of the things I read from you are all about creating a culture and, you know, even more importantly, or harder, or for better or for worse, creating a remote culture. And so I would love to ask you, like, why does culture matter?

Okay. I've realized is that the reason why we have a really healthy culture at Treehouse is not related to our good benefits, or even the way that we do things, you know, email updates or tools that we use or systems or, or anything like that. I, what I realize now, it distills all the way down to the core mission of the company. And our mission is something, um, that everybody in the company feels so passionate about that it ends up filtering into everything and allows people to basically be positive and excited about what we're doing no matter what happens. So our mission is very simple: to bring affordable technology education to the world so that they can change their lives and the world around them. So it's a very humanitarian mission, but clearly it's connected into building a big, exciting business as well. So everybody in the company feels we're so excited about what we're doing that it seems to trump any, any, uh, trouble that we have being a remote team. So this— we're up to about 55 or 60 people now, and, um, I would say about 50% of them are in our office in Orlando, and the rest of us, including myself, are not in Orlando. We're totally remote. So I'm in the UK, um, and I'm going to move to the States soon, to Portland, but, but I'll still be remote in a sense. Um, so, so we've managed to grow from basically, you know, one person in the beginning, me, plus, plus two people, the first guys I hired, you know, to 55 people in about, about sort of 14 months. Um, so pretty quick, and most of that growth has happened in the last six months, um, without losing any, any excitement. In fact, it seems to be getting crazier, and it seems to be getting that people are even more passionate about what we do. So I've thought about that. So we were sitting around talking about last time I was in Orlando, like, how weird that we've accelerated the growth of the company so fast. And most startups start to fall apart culturally when that happens, you know, the wheels start to fall off and people get disenchanted and disconnected and confused about what's going on. And yet we seem to be getting stronger and And all the folks that I talked to said, I think it's because what we're doing matters. And so, and somebody wrote an article about that, that, you know, hit Hacker News and went up the ranks. And it was basically about how the confusion is, you know, a lot of startup founders think that culture means, you know, simple things like Nerf guns and, you know, good lunches and, you know, and nice air on chairs and, you know, stuff like that. Whereas that, that just kind of makes life a little nicer, you know, it's great and everything, but if it doesn't create culture. So yeah, I think we're basically lucky to be doing something that we're both passionate about, but also could be a really big business. So, so that's, I think, what's related to that. And most founders, know they have that kind of spidey sense about if they're doing something that they think deep down matters. Like if you got them really, really drunk and they were talking to their mom or somebody they trusted, you know, what would they say about their business? And if in 10, 20 years' time from now they're going to actually believe it mattered. So, and I've done businesses where I, looking back, I didn't really think it mattered. Actually, why I sold my last business. There's a part of me that was like, you know what, doing events and conferences is exciting and there is a place for that, but I don't actually feel that I'm going to make a net positive impact on the world for the long term by doing that. So that's why we sold it and focused solely on Treehouse.

So let me dive into that because you say You, about 50 to 60 people. I mean, I think the number that most people throw out is around 30, is when things start to get a little, 30 people is where you go from everyone just does stuff and you're all hacking around to like, oh crap, we need some process or something. And you're at 50, you're mostly, or half remote, half in Orlando?

Pretty much, yep.

But like functionally, so the idea, you're lucky to have education. Like how big can education go? Like it's a pretty massive thing and I think it's, one of the most important things in the world. So I totally understand how you think like the idea, but are there functional things you do to like set the tone? I'm just trying to understand this from like if someone's here that they have a 3-person startup and they're gonna go to 50 people. Like do you, is it about getting people all bought into the vision from day one? Is it about employee onboarding? Do you do weekly updates? Are there things that you have like a manifesto that everyone has to buy into before they ever even thought about being hired? Do you fire people faster? How do you like, I'm really interested in like the functional? I don't know if you can go into this, but like, that's kind of what I'm interested in, and I would love to hear your thoughts on that.

Of course, let me dig into that. So, um, what we do is, um, I, I, I visually and verbally, you know, I'll hop on Skype and I will communicate the vision of the company to all new employees. And so, and because I'm passionate about it, I can speak in a way about it that really is— it's kind of primal and sort of You know, it's very passion-driven. So I think it all starts from the fact that the CEO and founder has to be able to communicate why what they're doing matters all the time. So you start the first time someone joins and you schedule a meeting and you literally talk them through, you know, what are we doing here and why does it even matter? You know, and that conversation usually lasts, you know, 15 minutes or so. And then after that, it's about reiterating it basically every week. So every week I do a video update, and I used to be able to do this over our— we used to get together using Coda meeting every Monday, and the entire company would gather around. But actually, we grew to the point where we couldn't physically fit the camera on. And then at that same point, it became logistically impossible. It became logistically inefficient to get everybody in front of the camera. It was like, oh, John's in the bathroom, and, you know, I don't know where so-and-so is. And eventually became this big time suck. It was like to get everybody in front of GoToMeeting for 15 minutes took an hour. And then multiply an hour times, you know, 30 people, and you're wasting 30 hours, you know, productivity with a 15-minute meeting. So I was like, damn, we can't do this anymore. This is— but I thought this is really important. So So basically I started recording a video and uploading it to Vimeo and password protecting it. And basically I talk for 5 to 8 minutes about, and I start off with a really encouraging tweet about Treehouse in there. It's amazing. Every week we get someone saying that we changed their life. So I just read it out like, hey, you know, you know, so-and-so said that, you know, said this and it's something amazing and inspiring. And then I'm like, okay, that's— I want to give you guys the big picture, so let's talk about it, you know. And then we, you know, I explain what stuff we're doing, why it matters. And then I'll reiterate, hey guys, don't forget that we are changing people's lives. And if at the end of our lives we're going to look back at what we did here and, and know that it mattered, if it'll be probably the one thing that we do in life that will— that we'll all be proud of, you know. And I, I say that kind of stuff all the time. And then at the end, I'll close with another positive tweet and then I'll just send out an email and say, hey guys, here's the update if you wanna watch it. And crazily, everyone watches it. Like I think some people multiple times, you know? So that's a good way. I think it has to come from the top and then from the managers, this constant emotional reiteration of the mission. And it can't— and the problem— this is why founders who are doing businesses that don't matter have a serious problem. Um, you know, if you are, you know, doing some, you know, some banal business that, you know, throws off cash but actually is stupid, you're never going to be able to get your team to care, right? Um, and, and this may sound really harsh, but this is why I stopped doing events. I mean, my last business that I sold, I was like, this doesn't matter. You know, I did some events that connected people and encouraged people and that mattered. But as soon as it became into this business where we had to generate revenue, we had to get sponsors in, it became this thing that didn't matter. And I got to get out. So, you know, sold it. And that's because I couldn't, as the founders, talk to the company with any sort of conviction and say what we did mattered. So that's kind of— so weekly reminders of the mission from the top with an emotion, you know. And then we do something really important, which is quarterly we get together physically. So we fly everybody into Orlando. And it's crazy, you know, there's like 55 people flooding into town. You know, we all sleep on each other's floors or in hotels. and then we work at the office for a week together. And that physicality, that meeting together in person quarterly really matters. I can tell like that, that's the glue that actually holds this crazy, you know, machine, you know, in place. So that, that really works. And that's expensive, you know, a lot of flights, a lot of hotels, a lot of food costs, but it's totally worth it. Um, and then we have a couple of other things. Um, we, we use TriNet for our HR. So, um, you know, it's just a great way of getting people onboarded and getting all the stupid stuff taken care of. Like, hey, here's how you contribute to your pension plan. And, you know, here's your healthcare and that stuff that's important, but you don't want it to become something that consumes someone's whole job. So the onboarding process, we use Trello, um, and we have an onboarding, uh, board in Trello. And basically each step, you know, is very important things. And as soon as we hire someone, we put them on that board and we start moving them through. And then part of, you know, some of those tasks are basically things like, you know, explain the mission statement, you know, so you take them through the whole thing.

Sorry, you still there?

Did I lose you? Are you still there?

No, I think we're good.

Still here.

So I just wanted to— I wanted to ask one, one thing. So you talk a lot about doing something that really matters, uh, and you talk a lot— you're all remote. So I wanted to ask, um, have you done anything that didn't work? Have you done anything in this company or the last or something you've learned that it's probably a bad idea for culture or actually was, didn't actually have any impact, it didn't actually matter at all?

Yeah, it's a good question. Yeah, I've done lots of stuff that doesn't, that hasn't worked, but I'm trying to pick a good one. Yeah, we, I tried to do this one thing where I tried to standardize. So I read a book called The E-Myth. And E-Myth is all about systematizing your company. And the problem is, is that I took it too much to heart and I tried to systematize everything. And one of them was how people answer the phone. So I wrote a little script so that they would say something. And the intention was good, like, hey, we want to consistent. Positive customer experience. So let's tell everyone exactly what they should say. But it totally backfired. I mean, everyone felt weird about it. They came across as robot, you know, like on the phone, and it just totally backfired and everybody hated it. And what I realized is actually, you know, we need to give people permission to be human and, and be friendly, and that's all that we need to do. And after we did that, it really worked a lot better.

So would your advice be, if you actually want to build a good culture, is to go into a market or an idea that matters and will make an impact on the world versus trying to build a functional process or culture or team around something that just doesn't matter?

Oh man, 100%. Yeah, yeah, without a doubt.

How would you say that Zappos does it?

Zappos basically founds their very company on the fact that their job is to make people happy. So the way they do that is by offering good customer service. You could say like, give me a break, like selling shoes or bags or whatever, it doesn't matter, who cares? But actually, people want and need those things and when they're going to buy them, If they have a customer experience that makes their life a little better and they smile, that is worth doing. So I think they basically empower their whole team to do whatever it takes to make customers happy. And then that's why their culture is so good. Because, and they, you know, they grew, they, it's really interesting. They went from nothing to thousands of employees and then got acquired and yet still have a good culture. You know, so I think it's all about that kind of messy letting people be human thing. And of course, that means you'll have to ask some people to leave the company because they, they, they act, you know, wrongly or weirdly, and then you'll have to get rid of them. But the truth is, most people, when you give them freedom to be human and positive, they actually do really cool things. So I think that's what's going on. And I also think you can't systematize it too much. There's things you can do like let's help people advance through their careers. Let's, you know, let's let them win financially. Let's do those things. But actually, when it comes to being happy, it's always a constant sort of, hey, how are people doing? And let's adapt. You know, you look at kind of companies that are old now and they've sort of systematized to the point where it's kind of like, all right, The kind of humaneness has been, you know, has been metricized out of this, you know, it's— and then even though it's efficient, it actually isn't very, very nice. So my belief, but I'm young and I'm inexperienced compared to that, like, this is the biggest company I've ever run, you know, at 55, 60 people. And it's the— and the longest I've ever run a business is about 5 years. So I don't I don't really know what I'm talking about. When I've been doing triathlons for 20 years and we have 1,000 people, maybe I'll know better.

We'll do another interview then. I think this is very insightful. For myself and anyone who watches it, I think it's awesome to see a company grow very quickly and also go after an idea that education is a huge space. Most people would argue that it's pretty broken and there needs to be better access to be able to learn. I wanted to thank you for taking the time today. I enjoyed it. And I hope that everyone goes and checks out Treehouse. And thank you again for coming.

Thanks for having me on. It was awesome.