Social Scene: VCJ Conference

Mark Suster had Internet TV on the brain, Todd Chaffee regretted the one that got away and Aaron Levie dazzled the crowd with his fundraising tales and the way Mark Cuban became an early investor.

Those were some of the highlights from the Venture Alpha conference at the InterContinental Mark Hopkins hotel on Oct. 20. It was the first conference for VCJ, and probably the best measure of its success was how soon after it was done, we kept getting asked when the next one will take place. No word yet, but stay tuned.

For now, we can recount what happened at our conference, which featured more than three dozen speakers, including VCs, angels, LPs and an entrepreneurial keynote by Levie, CEO and co-founder of Box.net. Interview by Alastair Goldfisher of VCJ, Levie shared an interesting anecdote about Cuban, one of the first investors in Box. “He’s everything you see on TV and more,” he said. “He’s as erratic, crazy and visionary as his blog and TV make him appear.”

Cuban invested about $350,000 in Box after Levie sent him an email asking him to write about the company on his blog. About a year later, when Box indicated that it wanted to “go bigger in the freemium direction,” Cuban said he didn’t really believe in the model. So when Box.net raised its next venture round, it used part of that capital to repay Cuban, who didn’t ask for a penny more than the $350,000 he put in. “He doesn’t act rationally,” joked Levie, who keeps a photo of Cuban on the wall in Box’s office in Palo Alto, Calif. Box has now raised more than $162 million in total capital.

Chaffee, general partner of Institutional Venture Partners, may have helped the firm make late stage bets in Twitter and other successes, but he says he missed out on another big one. Asked about his “biggest mistake,” he said it was not investing in Apple 10 years ago, before Steve Jobs turned the company around. “We saw it, but didn’t move on it,” he said. “I missed a 30x. That was stupid.”

Suster, the blogger and general partner from GRP Partners, delivered a keynote address at the end of the day in which he said that Internet TV will be the next hot investing trend. Not that anyone has been paying much attention to him, Suster told the conference crowd: “I’ve walked up and down Sand Hill Road and not a single person agrees with me.”

The conference then ended with cocktails at the Top of the Mark. And with views like that of San Francisco, no one wonder everyone was looking forward to the next conference.

Here are some pictures from the day. Photos by Oscar Urizar.