When you were 17, what did you want to be?
Oddly enough, I always knew I wanted to do entrepreneurial things. But I didn’t know any entrepreneurs, and I didn’t have any in my family. I didn’t really know anybody who did anything like that. I’ve always been interested in starting businesses. And I’ve always been sort of part of that realm, starting my own, or being part of startups.
I think I was mostly attracted to the independence of it. I just like to start stuff. I also don’t really like working for other people, I don’t like the corporate checks and balances thing, I’m not very good at that. Not necessarily so I can have a fancy car and a yacht, but so I can have the freedom to focus on all the other things I’m actually really passionate about. It’s a way to give back. If you have a bunch of money, you can start to dictate the way the human species is going. Thank god a guy like Bill Gates is the richest guy in the world, right? Because what is he using it for? To save babies lives, literally.
I knew I wanted that independence, I just didn’t know exactly what it was. I knew independence, I knew entrepreneurial, but I didn’t know anything beyond that.
How did you decide to attend University of Miami?
I applied randomly, and I probably could have used your help because I applied to just three schools. I didn’t measure whether they were a reach or not, I just picked ones that were far away. University of Miami, Emory, and Pitzer. So random. I just knew that they were far and I wanted to get out of the Northeast. Not that I didn’t love my family or anything I just wanted to go somewhere else.
University of Miami gave me a lot of money. My mom was heavily pushing me that way. She understood finances much better than my 18-year-old stupid self did. It was a good choice. It’s a pretty good academic school compared to what you might think of it. [Donna] Shalala, President Clinton’s Secretary of Health and Human Services, was the university President for 14 years, and she really turned it around. It did used to be Suntan U, totally. But they turned it around in that period, especially for science.
How did you choose your major?
I started as a philosophy or history major. I was always interested in those subjects, but then I didn’t know what I was going to do with those. It’s that translation that I guess is behind this whole project, like what am I gonna do, open a philosophy shop?
I ultimately chose finance, because I knew there wasn’t going to be any kind of nest egg waiting for me, so I needed to be able to make money right out of school. I think being more practical was part of it, but I just didn’t know anything about business. I thought this was the way you make money, to get independence so I could get into the things I really cared about. I don’t remember my exact decision; I just thought finance was a good way to make money. When I was in college, everyone was like finance, finance, finance. That’s where everyone makes all their money, like Wolf of Wall Street. But now, it’s like tech, tech, tech. You should be coding, you should start a business. Wall St. moved to University Ave. in Palo Alto.
But as far as majors, there are a few areas I still think are valuable. I think being strategic with people is insanely interesting when you get into the nuts and bolts of it. Coding can be really complex, but this statement always means this statement. With people you can be this way one day, and tomorrow you can be a completely different person. So it’s actually way more dynamic to read people. I never really valued that in college. If I were going to go through school again, I would have chosen philosophy. Just to learn how to think is so valuable. And I would take more advantage of the learning experience outside the classroom in college. You’re connected to so many different institutions. Like there’s an innovation lab at University of Miami that I never even knew about, which I obviously should have. And I’d meet a ton more people. I’d walk up and introduce myself to everybody. Like a crazy person. I’m never bored by people’s stories.
How did you get from college to where you are now?
I graduated and then I went and taught snowboarding in Park City for 6 months, which is what you do with a finance degree. It was a great time. And then I got a real job doing hedge fund consulting. I did the finance thing for like a year and a half, and hated it. I pretty much knew after a month that I couldn’t do it. I get antsy sitting in our workspaces even though I’m out and about all the time. So that’s also when I got into real estate.
I started house flipping for fun. I was working 100 hours a week, then I would get home and work on the house, but it was honestly a blast. And that was what brought me back to wanting to start businesses again. I liked managing the project. It was on me if it failed, which it didn’t, but it could have. It was during the housing crisis, so I couldn’t have picked a worse time. I probably could have made more money if there hadn’t been a global collapse of the housing economy. But it was fine and not long after that I quit the hedge fund job.
The girl I was dating at the time was from Maui. We started a tax prep business on Hawaii. It never really made much money; I think it was an excuse to move to Hawaii and surf. After that we moved to San Francisco and tried to do a few different things. The main thing I did was test prep to give me flexibility to do other projects. And then I ended up starting my own tutoring company because it’s good money and it allowed me to pursue my obsession with playing tennis while I was still young and could do it.
And then a few years ago, one of my best friends from University of Miami started up a sports analytics company and he asked me to come along. We would strap people up with sensors and then feed all that biometric data back through an app. It was me and him at first, and a tech guy who helped build the product itself. Initially, I was the director of business development, growing a sales team, and I was eventually going to be CEO. We were starting to get a little bit of traction, and then, last summer, our investors backed out at the last minute. We didn’t have enough time to go out and get another round of funding, so we pulled the plug. I think we were a little too early, honestly. I think in a couple of years when the technology is better, there will be a lot of companies doing what we were doing. But it was fine, because then I stumbled upon We Roam.
I’d actually had an idea for this, but it’s obviously taking a risk and I just wasn’t in a position to do that myself. I was doing research on the industry and We Roam was doing it the way I would have, from a professional angle. I just happened to email them, and Sean [Harvey], co-founder of We Roam, just happened to be in San Francisco that week. We met up for a beer and love blossomed and here we are.
Looking back, what seems clear to you now?
It’s hard for me to look back and say this is what I did wrong, this is what I did right. I honestly think that, so much of it you can’t correct. You’re so much a product of where you came from. I think I would trust my gut a little more. I would not have waited for permission, even from that young of an age, thinking I’m not old enough to do that. Who cares? Just do it. There are plenty of young people who do amazing things.
Maybe I should have just been an entrepreneur at 18. Maybe I shouldn’t have gone to school, maybe I should have saved myself that debt. But the experience was amazing and look at how many things I learned. If you go the college path, balance that fire in the entrepreneurial sector. If it works, you’ll grow into it. Mark Zuckerberg was a young CEO, but he’s pretty darn good at it now.
When you’re 17, you think you’re going to be farther along. You think you’re going to exit some businesses or be an expert at something. I think a lot of it is just being patient. Putting your head down and putting the work in. It happens at different times for everyone. I just try to be grateful and be patient. I think our generation and millennials have a pretty unrealistic idea of how long it will take. Even if you’re the hardest worker, the most badass networker ever, it’s still going to take a ton of time. Maybe your whole life.