Charlie O'Donnell tells us why he sometimes wishes he'd never heard of venture capital in this episode of The Deal's Behind the Money online video show. We spoke with the co-founder of Path101 Inc. soon after he presented at Silicon Alley Insider's Startup 2009 contest, in which his career development site was one of 10 finalists.
Thanks in part to his organizing nextNY, a networking group joined by nearly 2,000 of New York's tech-savvy 20- and 30-somethings, O'Donnell was also a runner-up for the 2009 Silicon Alley Award for The Man, which was won by his former boss, Union Square Ventures co-founder Fred Wilson. O'Donnell served as an analyst at Union Square, and both Wilson and co-founder Brad Burnham are among Path101's distinguished list of angel investors. The startup has raised $550,000 from individuals and NYCSeed, which invested $200,000 recently.
"People would tell me, 'Oh, you're lucky that you used to work for a venture fund because you understand what they want,' " O'Donnell wrote in his This is Going to Be Big blog recently.
"In hindsight, I don't know about that. I might have been better off not knowing that VC existed, aiming for profits from the beginning -- and then just being nicely surprised if some dude shows up at my door with a few million in cash asking to buy a minority stake in my business."
"Is Path101 still raising a round this year?" we asked.
"We're always raising," O'Donnell chuckles in the video. You can watch it below or download it on iTunes.
For more on both Wilson's and O'Donnell's thoughts about how the venture capital business is changing and what effect the changes will have on entrepreneurs and startups, see Honey, I shrunk the VCs in the current issue of The Deal magazine.
Check out The Deal's other Startup 2009 video interviews, including our chat with Mahalo.com founder Jason Calacanis, who calls Wikipedia founder Jimmy Wales a "poser," not an entrepreneur, but also names some 20-something entrepreneurs he respects, including Tumblr Inc. founder David Karp. Click here to watch our conversation with Karp, whose Tumblr won the 2009 Silicon Alley Award for Most Loved Product or Service, and here for our talk with Cheryl Milone, founder of Article One Partners, who took home the grand prize, a $25,000 investment from Boston VC firm General Catalyst Partners. And stay tuned: We'll be posting several more videos from Startup 2009 later Friday and next week, including ones with Venrock partner David Pakman and General Catalyst partner George Bell, who were both judges in the competition.
Also see the slideshow from Startup 2009, with first-rate photos of the event taken by photographer Michael Seto, with whom we enjoyed working. - Mary Kathleen Flynn