Cash is king

Guy Kawasaki warns of VC's half-glass-full sentiment, and why FilmLoop failed while Slide succeeded

In the month of October, we've seen startups such as Zivity, Seesmic, Adbrite, Zillow, and hi5 reduce their headcount to stretch out their dollars. Meanwhile, venture capitalists have been quick to dish out gloom and doom. Venture capitalist Bill Gurley of Benchmark, and angel investor Ron Conway, and partners at Sequoia Capital (whose PPT is embedded below) have told their portfolio companies to reduce costs and save cash. In this segment of "Lessons learned," Guy Kawasaki, author of "Reality Check," investor and entrepreneur, gave similar - while not as harsh - advice to entrepreneurs. Guy stopped by to be our guest host on Vator Box and to talk about his new company, Alltop. (Watch for those segments coming up.)

"Cash is king," he said. Many entrepreneurs lose sight of the fact that they have "a leash for a year," meaning you can "screw up" within that time frame. After that, however, venture capitalists will be quick to turn on you, he warned.

"There comes a point when they flip," he said. (I guess that point is right about now.) "They're going to say, 'I've done enough. It's not working.

"The first board meeting may seem hunky-dory and the next meeting, it'll feel like they're going to shut you down," he explained. Indeed, from the sounds of what Sequoia's partners have said to their portfolio companies, the board meetings are probably starting to feel like the latter rather than the former.

In this interview, we also talk about Guy's setbacks and failures. For instance, Garage Technology Ventures started off nearly a decade ago as a boutique investment bank, in which the partners took a 7% fee for matching entrepreneurs with investors. The problem with that model was that the investing dried up after the Internet bubble, he said. "7% of zero, is zero," said Guy. Today, Garage is a venture capital company that invests in the companies.

"Can the matchmaking model work today?" I asked, referring to a number of sites trying to broker the dealmaking between investors and entrepreneurs. It wouldn't work, said Guy. This is mostly because early-stage startups are raising far less than they were back in 2000, and 7% of $50,000 isn't enough to make a good business, he said. I have my own thoughts on matchmaking, read and watch "Entrepreneur matchmaking sites" for my views.

Another failure of Guy's was FilmLoop, which early on was a fierce competitor to Slide. In fact, they may have had a leg up on Slide. But FilmLoop, which Guy invested in, focused on the desktop. "Max kicked our asses," he said. "It was because we were too proud to change our strategy because we thought we were right and that Max/Slide didn’t understand how people really wanted to share photos... We should have seen the potential of MySpace when it started taking off."  

Guy offers up more advice to entrepreneurs, including not taking cash. You'll have to watch to get the rest of his advice. Be sure to watch my second and third interview segments with Guy in the coming weeks.