In the world of Silicon Valley venture capital, there's no name more iconic than Draper, the name that literally started it all. So when five Drapers from three generations get together to share their collective wisdom with a crowd of entrepreneurs, it's worth paying attention. 

That was the scenario a few days ago at Hero City in San Mateo, where Adam Draper, founder of the Bitcoin-focused startup accelerator Boost, interviewed four members of his family before an audience of Boost participants and Draper University students. On his panel: his grandfather, Bill Draper, co-founder of Sutter Hill Ventures; his father, Tim Draper, cofounder of Draper Fisher Jurvetson; his sister, Jesse Draper, host of "The Valley Girl Show"; and his brother, Billy Draper, a Facebook alum who now works with his father at Draper Associates. 

How do you maintain a venture capital dynasty across the decades? Not by being infallible. Bill recalled declining to invest in Apple Computers after a colleague went to meet Steve Jobs and reported back, "He smells and he's arrogant." Tim topped that by recounting how he missed out on making early investments in Facebook, Yahoo and Google. "My judgment, maybe not that good," he joked. "So if I turn you down, don't feel too bad." 

His advice, on the other hand, is spot on. Read on to see what other tips venture capital's first family had for entrepreneurs. 

Your brilliant idea is probably not just your brilliant idea.

There's a pretty good chance 50 other people just thought of it, too, says Tim. That doesn't mean you should give up, though. Instead, ask yourself: If we're all right, and this idea is something that catches on, what can I do to take advantage of the new market it creates? "If you can abstract one level further, you can maybe come up with something that all 8 billion of us will end up using," he says. 

Pick a co-founder who's not too much like you. 

Startups where the co-founders want to do the same job are destined for conflict, says Billy. 

Don't shoot yourself in the foot by being paranoid in a pitch meeting. 

You may think you're being prudent by protecting your secrets, but if you don't share your whole game plan with a potential investor, it's just going to look like you don't have one. "Don't be covetous of that," Tim says. "There's no reason to hold back."

Ask for money. 

It seems obvious, but it's a mistake entrepreneurs make all the time, says Adam. Not asking for money leaves investors thinking maybe you just came to network or pick their brains. Don't trust them to read your mind. "Say, 'I would like some money,'" he says. 

Be nice to everyone if you can.

The world is small, and you never know whose goodwill you're going to need next week, says Jesse. 

Don't be afraid to horse trade. 

Favors-for-favors is an old-school way of doing business, but there's a reason it's still around, says Tim. "And stick to your word. If you do horse trade, make sure you really fulfill your end."

An idea isn't everything. Don't give up if yours sucks. 

Make a good enough impression and a VC might be willing to help you come up with an idea worth backing, says Adam. "I find it difficult to turn down an entrepreneur who's both passionate and knowledgeable about their space," he says.

Never stop pitching.

The way to skeptic-proof your presentation is to go over it constantly with friends and family members until you're sure you've spotted every flaw and perfected your elevator pitch, Tim says. "Practice talking to people about your idea, anyone who will listen," he says. 

Don't use the fickleness of fortune an excuse.

"The whole thing is luck," says Bill, "but you have better luck if you work hard."

 

 

 

 

Published on: Apr 30, 2015