Last night at the Tribeca Cinemas, Fred Wilson spoke to John Heilemann in a live interview. The crowd was a nice mix of Columbia Business School Alumni, New York Magazine subscribers, and New York techies (there was even a nice crowd of nextNYers representing).

For the most part, the evening was about Fred and his views of web trends and his investment thesis. Only the last question of the night addressed the “New York question”, which was slightly disappointing for folks who read Fred’s blog regularly and wanted to hear an evening more focused on starting a company in New York City, as it was supposed to be the main theme of the event. Nonetheless, Fred’s insights are valuable for anyone in the industry, so the following are my best attempt at organizing my notes from Fred’s comments:

Difference between Flatiron Venture Partners (Fred’s fund during the first boom and bust) and Union Square Ventures:

• Flatiron was “pure opportunistic chutzpah”, which had a “lets invest in anything” approach to the internet in 1996.
• Side thesis with Flatiron: We can make money in New York City.
• Interesting fact about Flatiron: Flatiron invested $500 million from August 1996 to August 2000. Then $70 million during its remaining time in operation.
• Union Sq. set out with only $125 million to invest.

One of the best analogies of the night — judging from how often it was brought up at the open bar after the discussion — was Fred’s statement that “VC investing is a lot like poker.” With seed money being the first ante, it’s all about keeping the initial investment just low enough that you can see the “flop” and make your decision to continue playing or throw your cards in. This, again, highlighted a difference between Union Sq. and Flatiron, because when you invest $10 million as a first round - which was common at Flatiron - it’s hard to fold a hand you’ve put so much into, according to Fred.

Heilemann also asked why it seemed that all the most important web companies of today came out of the “doldrums” of 2003 — arguably a low point for the internet. Fred responded that he was fundamentally a contrarian, so “that makes complete sense” that the best would be created when everyone felt the worst. Fred mentioned his contrarian view again when asked about the possible bubble in 2.0 right now. “It’s getting easy to be an entrepreneur,” he added, and that’s not good. However, here are reasons Fred says 2006 is not 2000:

• There’s not an IPO market.
• A lot of companies actually have revenue now.
• Google insures revenue because it has created a results oriented marketplace for advertisers.

Regardless of bubble or not, Fred said it is in his investment thesis to put money in 5 companies a year, whether that year is 2000, 2003, or 2006.

More on Fred’s investment thesis:

• Company must be disruptive. Indeed.com is a classic case of how a company that’s disruptive. On a side note, he expects Indeed to reach profitability sometime within the next 9 - 12 months.
• Doesn’t matter if it’s a product or a company, as long as it can reach $10 - 30 million EBTIDA in the near future, because then it’s easy to devise an exit strategy.

On the upsides and downsides of being a known blogger:

• It’s humanizing, making social relations easier to manage. “It’s an ice breaker.”
• 50,000 people read his blog: “I don’t know most of them, but they know me.”
• On the downside, the need to post everyday gets overwhelming.
• Having so many readers prohibits him talking about his family very much.
• Professional privacy of colleagues suffers.
• When asked if the hyping of companies on his blog ever hurt him, Fred pointed squarely at MyBlogLog as an example where he helped hype a company and was then unable to close a deal with them before they got acquired.

Fred on starting up in New York City:

• You need good tech people when you start a company. There aren’t a lot of good technologists in New York.
• Nonetheless, there’s “a vibrant start-up culture in New York City.”
• And, among other 2nd tier web start-up cities (i.e. not the Valley), Fred claimed that New York has the best ecosystem and is easiest to start a company in, adding “it’s easier than ever before” to start a company in NYC.

Lastly, Fred mentioned that you need 3 founders for a company: A marketing guru, a product guru, and a tech guru. On his note that there are too few tech gurus in New York City, I have to provide this anecdotal evidence: After the discussion, I spoke with two teams of young entrepreneurs. Both teams were comprised of a product guy and a marketing guy, while they outsourced the tech to someone else. “Do you know of any good programmers?” one of them asked me. “I outsource too,” I had to respond.

Nate Westheimer is a Lower East Side-based entrepreneur working on a social networking product now in stealth mode. He blogs at innonate.com