During our third annual Vator Splash NY, we had a panel that featured Chris Fralic from First Round Capital, angel investor Deborah Jackson, Micah Rosenbloom from Founder Collective, Ben Lin from Great Oaks Capital Management, and Lewis Gersh from Metamorphic Ventures. Rick Heitzmann of FirstMark Capital moderated the panel, and he asked a really interesting question: What’s a company you can’t talk about without wincing because you wished you had invested in it? (I can’t imagine Rick’s one to talk, since he was one of the first investors in Pinterest, so, probably no regrets there, but whatevs.)
The investors on the panel had some interesting misses to talk about.
“General Assembly is one—those guys built a brand and put themselves in the middle of New York, and now everyone goes there,” said Chris Fralic. “You hear people say “I’m going to GA,” and you instantly know what they’re talking about.”
But there was also some cautionary language.
“We have what we call our ‘unportfolio,’ but it’s a hard question to answer. What you think you wish you should have been in right now might be tomorrow’s shit show,” said Lewis Gersh.
Deborah Jackson had a big miss…
“I wish I had invested in Twitter. I was skeptical when I first heard about it, but I’ve met so many people who have found their voice and amplified their voice on Twitter. We’ve seen on an international level that it can change countries.”
And then there was Micah Rosenbloom, who totally pinned the blame on his wife.
“I was pitched by two women from HBS who had an idea for selling beauty products online, and I went to my wife and told her about it and she said, ‘I would never sign up for something like that.’ So I ended up not investing in Birchbox.”
Ben Lin admitted to passing up a chance to invest in Airbnb, but he wasn’t the only one who was skeptical about it in its early days.
“When I heard about Airbnb, I thought it was the dumbest idea ever,” said Fralic. “I thought who would do that? And now here we are, we’ve invested in DogVacay, which is an Airbnb for dogs…” [Note: DogVacay won Vator Splash LA over the summer.]
Hindsight is 20/20 and all that jazz.
For the entrepreneurs out there, let this be a lesson to you: VCs can and do pass up really great ideas, so don’t lose heart.
Image source: maniacworld.com