What were some of your earliest entrepreneurial activities?
I read a Tweet that said something like there’s no entrepreneur that didn’t try to make their first dollar before they were ten, and that’s definitely the case with me. I used to take my older brother’s baseball card doubles and then pack them up, wrapping them in newspaper, and sell them to my classmates. I was a hustler.
I also played around with the Web. I made my first Web page for my Boy Scout troop when I was 11. My second website was for my design agency when I was 12. I posted websites for companies that didn’t exist as my portfolio.
One of the most exciting moments in my childhood was when I got AOL and found that it had this open source graphic design library. I got such a kick out of uploading assets and seeing how many people downloaded them. It was so addictive. I went from being completely isolated to people everywhere using something that I had made with relatively low barriers for me to accomplish it. It didn’t matter that I was 12 and living in Indiana. I could create something of value in the world that people wanted.
Did you study design at college? Or did you have design mentors?
I did the art program at Wake Forest University, mostly self-directed classes. So I’m sort of conflicted about how important classes or mentors are. All of the challenges I faced were necessary for me to become the person that I am. Those barriers differentiate me. Knowing who I ultimately would become, yes, it would have been helpful if I had had a counselor or a teacher who understood design and technology and helped me paint that picture. I really don’t know if that was even possible when I graduated high school, but obviously things are different now.
Did you have any work experiences before college?
When I started saving up for college, I began to sniff around for summer jobs. Through my mom’s friend, I interviewed for a graphic design position at an insurance agency in their video and multimedia department. They said I needed to know Flash, and I didn’t even know what Flash was. But during the interview I figured out that the interviewer didn’t know what it was either. So I lied and then taught myself as I needed on the job.
I also started this online pet store called The Reptile Shack, and it was actually a great business for an 18 year old. I had a quirky friend who turned his bedroom into a huge terrarium with iguanas sleeping with him. He complained to me that he didn’t have access to interesting lizards. We found out that there are a small number of breeders that supply most pet stores in America.
I contacted one in Miami and offered to make them a website. They said they didn’t need one, but then I told them I could make my own website and represent their entire catalog, and then I could send them my orders for them to send out on my behalf. So that’s what we did. They didn’t have an email so I had to print out my orders and I bought a fax machine. They shipped the orders in a box with a sticker I designed.
So Reptile Shack paid for college?
It got me halfway through college, and then I met Ricky Van Veen, who went to Wake Forest with me. Ricky was a celebrity on campus because he was the single guy at school who made money on the Internet in a very obvious way. He founded CollegeHumor in 1999, and it was already big in its first year. There were probably six of us Web geeks on campus that knew each other and wanted to work on the Internet.
So in my junior year, we became friends. Ricky up until then had considered CollegeHumor as beer money. Keep in mind that the dot com bubble had burst, and no one was sure what was happening. He and his partner Josh Abramson started to think that they could make a career out of it. They weren’t technical or product design-focused, so they recruited me and Jake Lodwick as contractors to do development and build out CollegeHumor as a more modern website. Before that, everything was hand-edited HTML.
Josh and Ricky wanted to monetize CollegeHumor. The T-shirt companies consistently bought the most ads and their buying was accelerating. We had this staff of volunteer CollegeHumor writers who came up with great ideas and we asked them to spit them out and then we put them on T-shirts. We launched Busted Tees as a lark, but that’s what truly allowed everything to take off and all of our careers to happen—this silly T-shirt business. We could take more risks because we had significant cash flow. We all felt secure that this could become a real job for us, and Ricky and Josh invited Jake and I to become equal partners in the business, and we all moved to New York together in the summer of 2004.
Were you excited to be in New York?
Moving to New York was incredible for me. I had thought that living in New York was something you do much later in life after you’ve accomplished something. Fresh out of school, with three great buddies, sharing an apartment, it was exciting.
There’s all this talk now about New York beginning to ascend into its place in terms of entrepreneurship, so you can imagine eight years ago how quiet and deflated it was. Less than ten Internet companies were in downtown Manhattan and now there are several hundred. Nick Denton who runs Gawker was the social chairman of all the companies and would host parties. It was a small tight-knit group.
In hindsight, we were pretty obnoxious. A lot of people in New York were grizzled old media types who had jumped to the dot com boom and were now dejected and trying to figure out what to do. And here were these kids with this silly, irreverent website making good money. We were so optimistic. That’s what we brought to New York. If anything, we annoyed everyone because we were oozing enthusiasm.
You founded Vimeo while you were at CollegeHumor. How did that happen?
When Flickr was released, it changed my entire perspective of what the Web could be, what design could be, what online communities could be, and my entire social life in New York became aligned to Flickr. I bought an SLR. I’d find places to photograph, and then I’d rush home and upload my photos. I’d sit there and reload to see who would come and who would favorite them. I started mapping who was who in New York by who was finding my photos and became friends with everybody.
We became photobloggers. It’s a word that sounds so silly now, but at the time it seemed avant-garde. For years, Jake had been obsessed with video. He had his own website with a small following where he released his video blogs. He would shoot a month’s worth of content, edit it down, and then release it. They felt like episodes.
He wanted to make a website where he could post his video clips as he shot them instead of once a month posting one huge monolithic edited cut. This resonated with me because at the same time, Cannon released these cheap PowerShot digital cameras that could record 20-second AVI files. You’d end up with all these video files that you didn’t know what to do with, and Flickr didn’t support them. So Jake made a simple text-based page, and then I chipped in and made the graphical version, which is not too different from what you see today.
We were talking about Vimeo constantly, but we couldn’t get anyone to believe it was viable. Then the SNL skit “Lazy Sunday” went viral on YouTube, another young video upstart. Until then, we had explicitly excluded commercial content from Vimeo because we couldn’t afford the cost of bandwidth. We also were afraid of the legal consequences. We were in New York City, and there was no “get big quick” culture or “what laws?” mentality. In California you do what you want and ask for forgiveness later. New York was much more conservative.
We made a decision shortly after we saw YouTube riding the back of commercial-viral content that we would take a different tact. If YouTube is about consuming video, we wanted Vimeo to be about creating video.
We were obsessed with it. We’d stop working on CollegeHumor at 6:00 p.m. to switch and work on Vimeo. We worked on it constantly for months before our partners gave us the green light to work on it full-time and we hired people to replace us at CollegeHumor.
Tell me a little bit more about how you specifically contributed to Vimeo.
I wanted things to feel as if they were made by a human. I wanted there to be quirks and inconsistencies and for users to feel like it was constantly being touched. I was so enamored with Flickr, so I largely mirrored their UX paradigms with my visual style.
We taped up sketches on a giant wall, and then we would do a combination of us writing and sketching what a page needed to do. We got into a flow where Jake would make a sketch, then I would move it into pixels, and then once it was in Photoshop, we would sit in front of a screen to discuss it.
Jake had made a 0.1 version of Vimeo by himself. Then we developed a process using pen and paper. We taped up sketches on a giant wall, and then we would do a combination of us writing and sketching what a page needed to do. We got into a flow where Jake would make a sketch, then I would move it into pixels, and then once it was in Photoshop, we would sit in front of a screen to discuss it. This is all so common now, but because we had no training, we conceived this process as we went along. For us, that was the quickest and easiest way to communicate.
In our relationship, I was driven by trying to impress him. I still felt very much junior, and so I tried to refine his rough ideas into something that would impress him about the strength of his original idea. And, echoing my teenage years, my childhood, I wanted to be known as a designer, not an entrepreneur. I admired all the makers and designers of web pages on the Web, and still felt I was totally in the freshman class. I put a lot of love into making something unique that would speak to our users, that was arguably different than anything that was out there. It was a very egotistical process.
Were there any specific fears or challenges that you had to overcome during this process?
It was always good. None of us knew fear. There was no reason to fear. We had CollegeHumor as a cushion, so we were never afraid that we would run out of money. I didn’t know anything better. We were constantly marveling at how cool the Web was, and the population of people who were making the Web was so small. We felt so fortunate to be able to make a living doing it. It was only good vibes.
Describe what happened when you sold Vimeo.
In the summer of 2006, we sold the parent company, and unfortunately Vimeo got sucked into this big conglomerate IAC because Connected Ventures owned all the IP. Jake and I wanted to carve Vimeo out of the deal, but IAC said that was a deal breaker, and so we sold it. It broke my heart.
It was a confusing time. At that point I believed, as did many of us in that company, that the most heroic thing to do, the greatest glory, would be to sell our company. That’s what you do. You start companies to sell them. The market seemed like it was sinking, the pending recession was in the air. And we had started this in college, so it felt like we had a long career ahead of us, let’s take some chips off the table and sell this.
We weren’t very sophisticated. In New York you couldn’t bump into someone to advise you on how to sell your company. There was nowhere near the amount of fever and media around entrepreneurship and startup culture. We felt completely in the dark. We had no idea. I thought that I could create more value starting from scratch and owning a hundred percent of a company than by continuing to work under a corporate company.
Do you regret not spinning out Vimeo?
If one of us had any clue what we were doing or what the stakes were, we wouldn’t have done that deal. At that time, there weren’t a lot of Internet companies being bought and sold. Plus, we had no reason to believe that Vimeo was special because everything else we’d tried before that point had worked. So to some degree we were arrogant, and we thought that we had the Midas touch, that we could keep conceiving of successful startups.
Only in the years since have Jake and I realized that there was something very autobiographical about Vimeo. It took the passion of two beginners’ minds, of people who had nothing at stake, whose motivations were completely pure. We made the website for ourselves without any other influence. It spawned this beautiful mission and community, and that’s hard to replicate.
Did you leave Vimeo right after the acquisition?
I didn’t leave right away because we were in the middle of a major redesign, which was the design that existed until six months ago. I stayed for a year after the acquisition because I loved Vimeo. We had worked hard for many years without stopping, and I had money for the first time in my life. We also no longer had majority control in Vimeo, and it felt different. The entrepreneurship was sucked out of the office because it was the four of us hustling, and now we had corporate overlords. There was no incentive to work as hard, and I wanted try something new.
So after you left did you take some time off to reflect?
The phase that I entered lasted about 3 years. I wanted to find camaraderie and people who had pure intention. I wanted to find something that got me excited in the same way as Vimeo had, aligned with my passion. I wanted to work on projects that couldn’t exist in any other time or place or couldn’t be made by anyone else. That comes from a personal place, that’s the sum of the team’s life experiences.
I had this notion that I’d used a whole bunch of my life to create Vimeo. Now I needed to live more life before I had something new to feel and say. It’s like how sophomore albums are so hard to create because your first album took you a lifetime to write. You were in the studio recording it for only a few months, but there was a lifetime of unique perspectives, thousands of decisions that caused you to have the emotions that you had. When you lay that down and the rest of the world hears it for the first time, they’re experiencing a brand new perspective that they’ve never known. So when you go to record your second album, it’s often not surprising to people, and it doesn’t have the same value.
I guess I thought that I could live life a little bit more and meet other people, find something that inspired me, and then restart the process all over again. So after Vimeo, I traveled and bought an apartment in Brooklyn and met a lot of friends. My neighbor Noah Kalina used to call me a “luncher.” I’d schedule an interesting meeting every day for like a year. There’s a lot of value in meeting people, to gather culture and learn.
In 2009, I joined Boxee because I wanted to work on something. I didn’t have a magnum opus that I wanted to make, but I fell in love with the Boxee guys because they reminded me a lot of the Vimeo team. I latched onto Avner Ronen, the CEO, as my mentor. I sat in on board meetings and learned about raising money for the first time. In those years after Vimeo, I began to mature. I observed the startup culture heat up and realized that my partners and I had many successes without having much wisdom. Now I wanted to know how to do it practically and rationally. I didn’t want to wait for that mania to get me working on something again.
How did that lead to founding your startup DIY?
During that time I also got into being outdoors, bought some land, worked on small buildings with friends. I’ve found that building these cabins is the simplest way for me to experience “beginner’s mind” again, the fearlessness and unconstrained creativity that only a beginner can have. I’m so addicted to it, and that’s what I had at Vimeo. There was nothing to lose, and I really miss that feeling. I’m constantly trying to put myself back in that position.
And so building cabins I get that feeling again. Then I’m in a low stakes position and no one’s an expert, so there’s no implied authority over each other. You’re constantly impressed by everything you do, and to an expert it looks like shit, but you don’t know who the experts are and you don’t care. Any incremental learning or improvement is obvious and important.
That’s how I ended up at Foo Camp to give a talk about the future of offline communities. I’m very interested in how this generation is learning how to find and build online communities and how they’ll take that knowledge and apply it to building offline communities. While I was there I met these guys who were building their own techno, rural neighborhood down near Santa Cruz. I felt the electricity. We totally hit it off and now we’re partners.
Describe more what the electricity was like when you first met them.
Put yourself in a position where you are the most fearless and where you feel the most creative… In that position, you start to attract other people because you’re the most attractive version of yourself.
This is a piece of advice for living in general. You have to put yourself in a position where you are the most fearless and where you feel the most creative. For me that is being outside, building these cabins, but it could be anything. In that position, you start to attract other people because you’re the most attractive version of yourself.
You’re radiant. You’re not pretentious. You’re kinder to other people. It’s easier to collaborate. You’re magnetic to the people you will get along with because you’re both achieving this flow state, this singularity, while doing the same thing. That was my strategy. If I couldn’t engender passion while designing websites, I had to find beginner’s mind wherever I could and meet people that way. And I found it.
I was nervous about this talk because I didn’t know if it would resonate with anyone. And then three guys my age were doing the exact same thing except one step ahead of me. As soon as I could, I went down to Santa Cruz and camped out with them. And then I started to make a habit of it, going every six to eight weeks. We talked about how fun it was to build an offline community together and all the skills each of us had to acquire or bone up on to be useful in that setting. You needed to know practical things like carpentry and framing but also a little bit about gardening and farming.
It is so empowering to be self-reliant and independent and to design so many parts of our livelihood. What if we could build a platform where we could teach all creative skills? We kicked ideas around, worked in Google Docs, and at some point we reached a critical mass: “I don’t want to work on anything else. This is exactly what I want to do.”
I’m back at a company that didn’t start off as a business or tech project but solves a curiosity and a really personal need. And because inventing with friends is so fun, we found ourselves thinking about this big idea. So we formulated a plan to turn it into a business so that we could all work on it.
Did you raise money?
Yeah, so by that point I had lots of experience. When I worked at Boxee I’d observed them raise a couple rounds. I got involved in Founder Collective and had done some investing myself.
What was your pitch?
What if you remade the Boy Scouts today? It was simple as that, and our answer to that question resonated with investors because it touches on a lot of themes. Education is malaised. There’s a lot of skills, especially technical skills, that people strive to teach not only for adults but children, too. And there are a lot of education startups but they’re missing passion. We made a compelling case for how we could engender passion in the skill-building process.
Any fundraising tips for designers?
Designers are in a great position because most founders have to rely on English to communicate their idea, and designers can elevate their pitch beyond the language to the visual realm. That is always more impressive. Our pitch process was rapid because we had put so much effort into visualizing our concepts.
I’m always disappointed when I see that founders who have design experience create a deck constrained to wireframes. I think that the onus is on them to go the next step. Your product may not be interactive yet, but there’s nothing keeping you from polishing it, and your effort invested pays off.
Wireframes are design. Obviously it’s the framework of the final experience. But the intangible of the graphic design choices made is important.
Are there any other tips? How you court investors?
It is interesting how earning an investment from a certain investor is a badge of honor. Many entrepreneurs believe that they’re going to get something special from them, like an advantage on top of the money. I think that’s the case only if you make it clear when you agree to take investment that that’s the deal, that you’re expecting feedback. It’s important for you to define how you want them to participate.
After fundraising, what are some of the steps you take in the first 90 days?
Once we got our money, we started running around like chickens with our heads cut off. We were so amped to get started. What happens during the pitch process is that you sometimes end up modifying your ideas in order to make them more marketable. Sometimes you need to push the timescale so that you can propose a bigger version of yourself. In hindsight, I had become so convinced as to what we should be, that I started to believe my long-term vision was the short-term vision. I wish that I had spent more time recalibrating my expectations for the company so that we weren’t trying to do too much too soon.
Were there other key experiences before your recent mobile app was publicly released?
DIY is unique because our members are kids, and so the challenge is that they have inconsistent access to the Web. To reach kids, we needed them to find us, and we assumed that that should be on the iPhone because anecdotally we so often see that the iPhone becomes the VHS or DVD pacifier. Parents now congratulate their kids by buying them the app of their choice.
We ran out of the gate building our iPhone app without much understanding of kids or our network or who we are. We made a lot of assumptions very quickly, and as everyone knows, it’s difficult to iterate on an iPhone app because of the costs of programming Objective C and X Code plus the time for your app to be reviewed and pushed live by Apple. So the cycles are so much longer that our learning was stretched out over a longer period of time.
I wish we had started on the browser on the desktop because on that platform we could iterate the fastest. We’ve since revised our strategy and are developing the iPhone as our background process, and most of our energy is toward iterating on the Web because we can test there much more easily. Once we have got down pat our language choices, our design patterns, then we port them back to the iPhone.
Is there anything that you’ve championed or have gone to bat for?
A couple of my partners don’t have Web backgrounds. They have creative backgrounds where they created very polished products with big budgets and long production schedules. So their instinct is to polish something before you let anyone see it. Early on, I got caught up in that.
We don’t know that any of this stuff we believe is true. We’ve got to build it in its simplest form and put it online as soon as possible. That [allows] the team to interface with our users much sooner.
We don’t know that any of this stuff we believe is true. We’ve got to build it in its simplest form and put it online as soon as possible. That simple wisdom that every startup knows proved itself valuable again, not only because we’re learning a lot, but because it’s allowing the team to interface with our users much sooner.
Something that I often see happening in startups, and it kills, is that the product to be launched is a moving target. They go so long without putting something touchable out there that teams start to wilt and rot because they’re missing such a big part of their life, which is validation and recognition for what they’re making. It’s such an important driver for creative people. If you work in a vacuum for too long, you lose touch with who you’re making it for and who’s using it.
Which brings me to my final question: What impact do you envision your current work will have?
So much Web development feels like we’re strolling down Main Street, pointing at different business, and saying “let’s put it online.” We’ve been creating digital versions of the world that already exists for a decade or more and a lot of that is still going on. There was a lot of money to be made there, and it’s distracting to move beyond it when so much more still can be done. But our generation is ascending to key positions and beginning to inherit infrastructure, and we finally have enough wisdom and life experiences to make big decisions.
With everything that we know now, it’s time to re-imagine what communities, livelihood, education, and communication can be.
The technology and wisdom that we have now should dramatically change what it means to live on earth. The novelty of creating a digital version of analog life has become passe. With everything that we know now, it’s time to re-imagine what communities, livelihood, education, and communication can be.