Five Minutes with Angel Investor Dave McClure

Angel investor Dave McClure has a talent for gathering budding entrepreneurs, technologists and venture capitalists for a positive exchange of ideas and experiences. One need only attend a Startup2Startup meeting in Palo Alto — a monthly dinner that acts as a kind of night school for first-time founders — for proof.

Last week, I chatted briefly with McClure about how the evenings come together, and why he introduced them earlier this year.

What do you most try to emphasize at your dinners?

It’s mostly about helping the next generation of entrepreneurs learn the ropes, which, given the downturn, is more important than ever. People are interested in the lessons learned by people who’ve been there before. A lot of the inspiration for the dinners came from Round Zero, a similar style event that used to take place from ’98 to 2002 and focused on new startups and first-timers.

The dinners always feature guest speakers. Next week’s, with Y Combinator’s Paul Graham, will mark your seventh event. Will you continue to organize one meet-up a month for as long as you can take it?

We’re going to take December off, but we’ve gained a relative lot of momentum in a short period of time.

I’m more challenged to figure out how we keep the dinners the right size, of around 100 people. We usually have 12 tables, although because [our last speakers] Reid [Hoffman] and Matt [Cohler] were so popular, we had 14 tables last month.
How do you try to strike on the right balance of entrepreneurs and investors, so that no one feels like they’re being preyed upon?

It’s a lot more art than science. As far as the makeup goes, a fair amount of attendees are people in the Y Combinator universe. [Y Combinator is a three-year-old company that provides seed financing, guidance, and killer contacts to nascent startups.] Or it’s other people who are in Silicon Valley for a week or a month and for whatever reason, I’m accessible to them.

The nice thing is that we have a good flow of investors and experienced entrepreneurs who are making recommendations for new talent. So it’s not all coming from me now.

I know you don’t like to invite the same people more than twice. How many guests are new each month?

About half the audience is new each time.  Repeat attendees are usually moderators, sponsors, and a few other folks who’ve been invited back. 

The group’s appeal is its ability to identify up and coming talent. I think the challenge is keeping yourself aware of new folks but keeping your filter high enough that you’re investing your energies in the best and brightest.

What was your table talking at your last dinner? I noticed you seated yourself with Reid and Matt.

I don’t usually seat myself with the speakers, I give other people the opportunity to do that, but I did indulge myself. We sort of had two topics going on: The downturn and social networking. We talked about social networking platforms, including about LinkedIn’s newest release and what Facebook has done right or maybe not right.

I think there was probably cautious optimism around Facebook at our table. The current trendy opinion is that the bloom is off the rose, but I personally can’t see how you can look at a 100 percent or greater annual growth and not think that’s a great thing, even if they’re upside down on infrastructure costs. Monetization is very good from what I understand and if they figure out better models in the future, they’ll be very, very profitable. There was still substantial optimism at our table.

Have some lasting connections come out of these dinners? Have any entrepreneurs been funded thanks to the VCs or angels they’ve eaten beside?

I don’t know whether there’ve been specific fundings, but several hires have come out of the meetings, which makes me very happy. It’s really fertile ground for making connections quickly.

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