Interview by Howie Rhee '04 on May 20, 2011
Funny part about my Duke experience is that I learned entrepreneurship while there...almost against my will. I started as an economics major but never finished it and pivoted towards Public Policy (like so many do...). I never really connected to Duke academically in any meaningful way while I was there. My favorite classes in the end were a whole bunch of American Literature courses I took in flagrant disregard of the career preparatory effort that consumed so many of friends. I was probably best known for being in DSG, but that wasn't quite the right match for me either. Mostly I was lost, not ready to think seriously about what I wanted to do when I grew up and shocked that everyone else seemed so certain.
My true calling was incubating a little project that my parents hoped wouldn't distract me from my studies. While a freshman in Blackwell, I refused to pay Ed and Steve $175 for a loft and took a trip to Home Depot in my roommate's car. With $45 worth of wood and materials, I made the ugliest, most rickety, unsafe loft you've ever seen. I had my roommate sleep on it (sorry Joe!).
Two days later, a fairly unsavvy friend asked me to build one for him as well. And thus, before orientation had even ended, Student Lofts was born and I was an entrepreneur. I didn't think of myself as an entrepreneur, but that's what I was. I built 15 lofts that year and 30 the next. Junior year, I had a team of friends show up in August to build lofts in the outer Wannemaker lots. And senior year, we cornered the market by building a website and putting a flyer in the pre-frosh mailer. Ed and Steve were blindsided. I maxed out 14 credit cards to pay for materials, hired 10 workers from Durham, and sold almost 200 lofts at $200 a pop.
Talk us through the jobs you held after graduation and before business school. How do those connect to your current entrepreneurial activities, if at all?
I wandered a bit after Duke. I skipped on campus recruiting because nothing appealed to me. I ended up teaching English in Japan and then running a Jewish summer camp for 4 years. I learned more about business and startups from running that summer camp than anything I've ever done. Managing people with inspiration instead of discipline. Creating a vision young people can believe in. Challenging people to accomplish things they didn't think was possible. Helping them grow personally. Late nights of pizza and hard work. I did this in summer camp, and it's what I do everyday in startup land.
Much of this I first learned in Tony Brown's leadership class. His leadership map assignment really rocked me. Tony helped me grow as a person, and I will never forget him for that. I try to perform the same task with my summer camp counselors and my startup employees. When I play a meaningful role in their personal development, they stop focusing on salaries and job titles. My job as CEO is to help people achieve things they didn't think were possible. Nothing is more powerful.
Everyone gets something different out of Duke; sometimes it just takes awhile to sink in.
You went to business school in 2006, tell us why you decided business school was right for you.
Business school wasn't right for me.
I loved my time at Tuck. Absolutely loved it. But it wasn't right for me. I applied to business school because I thought it was time to grow up and get a real job. I thought it was time for summer camp and non-profits to be hobbies and for normal business roles to be my career. I never once thought I'd go to learn about entrepreneurship.
I don't regret going to business school because it's a part of who I am, but if I could go back, I wouldn't do it. As I rant about in my blog http://humbledMBA.com, my passion is in startups and business schools are simply not very good at teaching startups.
You founded Openvote while you were in school, and then FlightCaster in 2009 (about six months after you graduated). What was the progression from one to the next?
Openvote was my first ever experience with web startups. Like Student Lofts, I was just drawn to an idea. For Openvote, it was building a platform for community polling and discussion. No experience in web development. No experience in fundraising. I had to learn everything the hard way. The company failed after 2 years of me pouring my heart and soul into it. I lost my investors' money and all of my money (and then some...).
I got a normal job at an advertising agency, working on brand strategies for Gillette. I quit a month later, unbelievably bored and upset with myself. With no money, huge debt, and failure on my resume, I took another swing.
I started FlightCaster days later with one of my best friends.
Tell us about Y Combinator. Describe it briefly for those folks who don't know what it is. What drew you to Y Combinator and what did you get out of it?
Y Combinator with the proverbial napkin business plan. Y Combinator is a seed-stage incubator run by Silicon Valley guru Paul Graham. We were one of 35 companies picked out of 1000 that applied for the program. He pledged a $20k investment, contingent upon us immediately moving from Boston to Silicon Valley. And he gave us 20 minutes to make the decision.
Best decision I've ever made. Y Combinator has it figured out. It is hands down the best way to do a startup. YC helped reformat my thinking about startups, removing business school fantasty-land slideware, for real world advice. Everything came down to the YC mantra: build something people want. With that little nugget at the core, we received mentorship from every top thinker in the startup world: Peter Thiel, Andrew Mason, Mark Zuckerberg, Reid Hoffman, and on and on.
And just as importantly, we met dozens and dozens of YC entrepreneurs that were months or years ahead of us. While the celebrities were great for inspiration, these ground level advisors provided real help everyday. It's this peer-to-peer interaction that excites me so much about what we're building in the Duke community with DukeGEN. We've got some real momentum now, and I'm really excited to see DukeGEN playing a similar role in people's entrepreneurial lives as Y Combinator did for me.
Give us an overview on FlightCaster. What does FlightCaster do, and how is it going as a business?
Some stuff we do is easy. When your plane out of RDU is coming first from JFK first, and it takes off 90 minutes late--odds are, you're going to be 90 minutes late as well. Not super hard to conceptualize.
Building a team of engineers and machine learning scientists that can process a massive amount of data and spit it out in a beautiful mobile app is just a tad more difficult.
We sold the company in December 2009.
What has it been like starting a company in Silicon Valley? How is it different than say starting a company in New Hampshire or North Carolina? Would you recommend it for first time entrepreneurs (to move there)?
Doing a startup in Silicon Valley is like doing politics in DC or movies in Los Angeles or basketball at Duke. It's not only what everyone does, it's what everyone talks about. All the time. When I walk into Coupa Cafe in Palo Alto, half the tables have young entrepreneurs pitching investors over their iPad. It's like the whole Bay Area is all rolled up into Clocktower quad and everyone knows everyone.
You can succeed absolutely anywhere. But in Silicon Valley, your odds of success are much, much higher because you're in a supportive community where ideas, talent, and capital seem to flow endlessly.
For me personally, it's the first place where I've ever felt accepted. Geeks are in charge in Silicon Valley. Nobody cares about pedigree, job titles, or salaries. And everyone is kind of rooting for each other. If you can make it out here, you certainly should. It doesn't disappoint. If you are a first time entrepreneur, ping me when you get here and I'll do whatever I can to help out.
A lot of Duke undergraduates would like to start a company, but feel like they don't have the knowledge or the money to do it. Do you have any advice for them?
Startups take the same amount of time as any other challenging profession. Want to be a lawyer? Spend a pile of money for 3 years of law school and become a lawyer. Want to be an entrepreneur? Spend a pile of money on 3 years worth of failures and become an entrepreneur.
In the hundreds of startups I know, I see no correlation between age and success.
The one thing I know that does correlate with success is technical ability and aptitude for technical ability. The single greatest professional regret I have is not learning to code while at Duke.
If someone is deciding between say a Y Combinator or going to business school - what advice do you have on making that decision? Is one obviously better than the other as a first step towards starting a company?
Y Combinator in a heart beat. From experience, choosing the grad degree will, 98.8% of the time, lead to the decision not to do a startup. At Tuck, we had 250 in our class. And 3 entrepreneurs. While almost all students took entrepreneurship classes, 98.8% chose to accept a huge paycheck from BigCo Inc.
In business school, your friends want to talk about McKinsey, JP Morgan, General Mills, and Blackstone. Entrepreneurs emerge, but always as the exception.
I'm working really hard on my blog: http://humbledMBA.com. I do have a new startup incubating that I'm really excited about it. If you're into commercial real estate or investing in Duke startups, give me a holler and I'll share what we're up to. It's the next big thing ;)
I work extensively with the Network for Teaching Entrepreneurship. We're bringing startup lessons into underserved high schools.
If you're an entrepreneur or a wantrepreneur thinking about taking the plunge, reach out to me on Twitter (@jasonfreedman) or your communication platform of choice. I'll do whatever I possibly can to help you...
Read other profiles of Duke entrepreneurs