Formerly at Stickybits / Turntable.fm, The NE Patriots / The Kraft Group, Massive Inc., Microsoft. Winner of the 2011 Startup Bus (TripMedi). Tech Obsessed. Boston Sports Fan. Food Lover. Yogi. Outdoors Man. Friend.
Has the change from entrepreneur at a startup like Stickybits/Turntable.fm to VC been as you had expected? Any surprises?
Before I joined Stickybits I was an investor and biz dev hustler at Massachusetts-based The Kraft Group so going back to the other side of the table wasn't too much of a shock. What surprised me the most, however, was how my experience at Stickybits / Turntable.fm helped me become a much more effective investor and advisor because I developed a new perspective on product, risk taking and hustle.
I was also surprised with the differences between being a tech investor in NYC and a tech investor in Boston. The startup community in NYC feels about twenty five times the size of the startup scene in Boston both in terms of people, diversity of talent, and quality companies. In fact, in my first three months at Lerer Ventures I've met with hundreds of entrepreneurs just starting out or looking for funding. The entrepreneurs in our community are building companies in just about every sector imaginable -- security, fashion, art, e-commerce, ad tech, fin tech, big data, social, gaming, green tech, med tech and even hardware. No wonder why the Boston investors are flocking here on a weekly basis.
Finally, I've learned quickly that being an investor and helping run a seed fund is extremely challenging and time consuming. Believe it or not, I now work more hours and sleep less than I did while I was at Stickybits / Turntable.fm. I don't mind the hard work and hustle because I truly love my job and the NYC tech community.
What’s your biggest professional regret?
While I'm a firm believer that everything happens for a reason, my biggest professional regret is not moving forward with Mike Karnjanaprakorn to build Skillshare. When I was living in Boston, Mike K. visited me for a weekend "think tank" session at my apartment where we discussed, debated and explored a variety of disruptive start up ideas. By the end of the weekend, Mike and I had created the idea for Skillshare and we were convinced that we were going to disrupt community based education. A month passed and I ultimately decided not to purse the opportunity with Mike (and Malcolm) because I had my "dream job" at The Kraft Group and wasn't ready to take a big risk.
Since then Skillshare has emerged as one of the most promising startups in NYC and the company has raised money from some of the top VCs in the country including Union Square Ventures, Spark Capital, Founder Collective and SV Angel. I'd be lying to you if I told you that I didn't want to be a part of it in some way. There's no denying that Skillshare has the potential to be a category defining company built in NYC just like Meetup, Kickstarter, and Etsy.
That said, I truly couldn't be happier for Mike and Malcolm because they have a once in a lifetime position to create a disruptive and global brand. The experiences I've had in place of Skillshare have been nothing short of fulfilling and rewarding. I wouldn't have been able to work at Stickybits / Turntable and Lerer Ventures. I also wouldn't have worked closely with amazing people like Billy Chasen, Seth Goldstein, The Lerer's and Eric Hippeau. Those experiences and people have helped shape me into the person I am today so I have no reason to ask what if.
What’s it like being a Boston sports fanatic here in New York?
It all depends on the season and the year. When the Pats, Sox, Celt's and B's are winning championships and beating the NY teams, I love being a Boston sports fan in NYC :)