A Candid Conversation with Matt Colyer

Matt Colyer has been in startups for his entire working career. That’s five years now; he graduated Olin class of ’07, and immediately started his own business. That particular startup didn’t pan out, but he’s remained a staunch startup developer ever since. He has recently launched a new company, Easel, cofounded with Ben Ogle.

Matt and Ben rolled into Yerba Buena gardens, downtown San Francisco, on bicycles. Over a chess table in the shade, Matt and Ben told me about Easel and what it’s like to live and breathe startups. Matt explained his love for working through ever-changing problems and learning on the fly.

FRANKLY: Can you start off with a brief description of Easel?

COLYER: Easel is a visual design tool. We want to improve how people create web sites. Right now, people use Photoshop, but Photoshop is really meant to edit pictures. We think there’s a real opportunity to make a tool that’s actually built for designing web sites, and do it online.

OGLE: It’s for professional teams, who are going to write layout code themselves. We’re really focused on making sure that they can get their ideas out more efficiently.

COLYER: So that’s our idea. We’re going through the Y Combinator right now. Our plan is to raise money and then start building a team. We have a minimum viable product online now.

We’re definitely interested in talking to Olin students who are interested in working at startups, because we’re going to need to hire engineers as we grow.

FRANKLY: Based on your LinkedIn, it looks like you’ve only worked at startups?

COLYER: Yeah, that’s pretty much true. After Olin, I knew that’s what I wanted to do. I did Y Combinator while I was at Olin, back in 2006. It was a different program back then, it wasn’t nearly as prestigious. Paul, the creator of Y-Combinator, wanted juniors and seniors. So we interviewed with him and were ultimately accepted. The idea was, you’d take your summer off, and ideally quit school. I took my junior second semester off. And that was Flagr.

After doing that, I knew that that this was what I wanted to do. I have always been a programmer, but building companies and building products is more interesting. I still think of myself as a maker, but making organizations.

People from Olin get that, because Olin is about creating organization, and building what doesn’t exist yet. There are a lot of similarities. I went to a startup college, then I went to startups—I’ve been doing startups for the last twelve years of my life!

FRANKLY:When you launch a startup, does that come with a fear of failure?

COLYER: No. I mean, you don’t really think about it.

OGLE: There’s no fear of failure. Are you kidding me? There’s fear of doing the wrong thing.

COLYER: Well, but that’s not failing. That’s different.

FRANKLY: What is the wrong thing?

OGLE: It’s doing something that isn’t blatantly wrong, so that you fail, but it’s a little wrong, so you don’t get the uptake you could if you were doing the right thing. That’s what I’m worried about.

COLYER: That’s an interesting point about failure: what is failure? A startup, to be successful, is like a rocket ship- if you’re doing well. One mode of failure that people don’t often think about is the startup that goes sideways. It’s like Ben was saying: you work really, really hard, and you just keep doing the same stuff, but nothing ever takes off. It’s painful, because it’s not clearly wrong, because you’ve got something, but it’s also not clearly right. I think that’s probably the worst state to be in. Because if you fail, and run out of money, it’s pretty clear you’re done.

But it’s unclear when you’re not totally succeeding and not totally failing.

The reason I like startups, and part of the reason I went to Olin is, I feel like there’s a lot less politics involved, and it’s just a more efficient organization.

I’ve worked in big organizations. My last startup that I was at before this, Typekit, got aquired by Adobe. So I was part of Adobe for about six months. Adobe is a 10,000 person company. And the things that happen in a 10,000 person company are vastly different than things that happen in a 20-person company.

There are definitely challenges with a 20-person company, too; you have personalities. If one person on your team really doesn’t mesh with you, you can’t hide. You kind of have to confront it. But you don’t have to file expense reports every week, and all the other stuff that goes with a big company. There’s definitely a tradeoff.

I think that most Olin students, at least in my experience, are much more suited to startups, because there’s a wide variety of tasks. I think this is something that Olin students really understand: they want to do twenty different things, and do them all well, and have an interesting time learning the next thing. I know that if I had to do the same thing over and over again for four years, it’s just not interesting to me. In a startup, that’s the ideal employee. The thing that you start, when you’re the first employee, is not the thing that you’re going to be doing in two years. You need somebody who is excited about learning these different things, and taking on things that they don’t know how to do, and just figuring them out.

FRANKLY: What became of Flagr?

COLYER: It was a really good learning experience. You can’t get education like that. You can’t learn faster than by failing, and doing it yourself. One of the interesting things you learn about startups, is it’s essentially like you’re dating somebody—

OGLE: Like you’re marrying somebody.

COLYER: So there’s drama, and there’s fights, and there’s messy breakups. There’s definitely team dynamic issues. We were all young, and didn’t necessarily have the expertise in doing this, so we just went all in, and tried to figure it out, and ultimately the team didn’t really work out.

And on top of that, one of the things they were focusing on then, was Paul told you not to have a business model.

OGLE: Paul being Y Combinator.

COLYER: And so, we didn’t have a business model. And so when we ran out of money, we didn’t have any more money.

Some people say now that it was a company ahead of its time. 2006 was before the iPhone. The idea behind Flagr was that it was a mobile location startup. Somewhere between FourSquare and Yelp. Except that the only thing people could do on their phones was text. There was no Google Map on your phone. There was no GPS.

So there was a variety of issues. The idea was ahead of its time, the technology wasn’t there, the team—we weren’t experienced, and we didn’t have a business model. So if you add all those things together, there was pretty much no way we were going to succeed.

FRANKLY: Did you learn as much from your other startup experience as from Flagr?

COLYER: I think so. They’ve all been very different.

OGLE: He got to see one work! He got to see Typekit really work.

COLYER: Yeah, the last one I went through, I actually went through a successful startup.

I was the first engineer who wasn’t a founder. I went with them all the way from six people sitting around a table with laptops hitting into each other, to the point where we got acquired by Adobe and moved into their offices. It’s a huge learning experience to see, when it works correctly, what it looks like. And also going through the acquisition process, and understanding how things actually come out in the end, when things are successful.

FRANKLY: What were you most involved in at school?

COLYER: I did NOTE, which took donated computers, refurbished them and gave them to families who needed them.

And I played on the soccer team—do you guys still have a soccer team?

FRANKLY: Did any particular teacher or class stand out as influential to you?

COLYER: Mark was a really good advisor. I talked to him while I was doing Flagr. I still get advice from him, and just check in and see how things are going.

The most influential class was probably UOCD. I still think that’s the most valuable thing that Olin provides. People are starting to catch onto it out here [in San Francisco].They’re starting to understand the importance of design. But they don’t really know what that is. They’re like, we need someone to make it pretty.

It’s the opening for Olin students come in and say, you need something pretty, but you also need to understand what people are trying to do with the product, and really understand them. That was an eye-opening thing for me; I had never heard about it before I got to Olin.

FRANKLY: Do you feel that Olin prepared you well for startups?

COLYER: I think so. I think the biggest thing is the willingness to do stuff that you don’t know how to do.

FRANKLY: Do you have any advice for Oliners wanting to start their own companies?

COLYER: Well, definitely wait until after you graduate. You can’t do both. I think some Olin students try, and I think it’s admirable, but I think it’s too hard. And outside investors don’t want to take that risk. It’s just one more thing that can go wrong.

Dropping out I think is a bad idea too, because if it does fail, you need to be able to go on to the next thing. It’s more difficult to get hired if you don’t have a degree. I also think there’s just important stuff you learn during college.

OGLE: What about finding the right people? Because you’re married to these people.

COLYER: Yeah. The number one thing when you’re starting a startup, is to get the right people. And pretty much everything else, you’ll work it out. Find the right people and don’t give up.

OGLE: Even when it looks like it’s going to break.

COLYER: Just keep going. If you have money in your bank account.

FRANKLY: How did you know when you were going to start Easel?

COLYER: We’d been talking about it for a while. There’s only certain people that you meet during your life that you’re willing to do a startup with. So it’s when the opportunity presents itself. And you know, just jump on it.