Welcome to Breakfast
Every two weeks for the last 5 years, I’ve had breakfast with my grandfather Bill Draper. I call him Pops. Some people call him a legend. This handbook is
my attempt to distill the knowledge of venture capital he’s passed down over eggs and bacon in the 100+ breakfasts we’ve enjoyed together.
I got into venture capital the old-fashioned way. My great-grandfather founded it, my grandfather improved on it, and my dad took it global. My family’s history is synonymous with the history of venture capital in Silicon Valley—it’s hard to talk about VC in the last 70 years and not mention “the Drapers.”
As a result, I know venture capitalism the way a cobbler’s son knows cobbling. It’s the trade/craft that my dad, granddad, and great- granddad all chose to pursue; I was their apprentice, and I’m now a VC too.
I’m proud of that and grateful for it. I started with a leg up on the average new venture capitalist, being raised with stories of the founding of Tesla, Hotmail and Skype. Our dinner table conversations were always about cool ideas and technologies that scale.
With that knowledge, I founded Boost VC, became the first investor in Coinbase, and invested in 400+ startups in my first 12 years as an investor. I’ve written either the first or second check to 7 companies that reached billion-dollar valuations, back when they were two- or three-person teams. And our first fund at Boost returned more capital than 95% of funds that year.
My unique history with this industry got me thinking: How can I give this experience to someone else? How can I start to share what I’ve learned?
Breakfast With Pops is my first attempt to put the most important knowledge into one place. The main character is my grandfather, a.k.a. Pops, a.k.a. William Henry Draper III. He’s the most charming man you could meet, and he’s still sharper than everyone.
Breakfast is at Buck’s restaurant in Woodside, CA. It’s a family restaurant with a secret: VCs have invested in some of the greatest startups in history at these tables. Rumor has it that the Google and Yahoo deals were both put together here. There are a couple of little clues, like the display case labeled “Thanks for the memories!” containing a collection of silicon memory chips made over many years. But there’s also a hanging model airplane and one of Shaquille O’Neal’s basketball shoes.
During one of our breakfasts, if someone were to look at us directly from the side, it would be like looking at a 90-year-old hang- ing out with his 30-year-old self, discussing business, politics and family. We do have a lot in common—except I’m wearing bright orange pants, while Pops is always dressed immaculately in a colorful collared shirt and a sport coat. (One time years ago, he wore this same outfit on a canoe trip, the canoe capsized and flipped him into the water, and, I swear to you, he walked out of the water with the sport coat tossed over his shoulder, looking like Sean Connery in James Bond. He didn’t look wet. He was completely un- shaken, with a grin on his face).
To this day, when I look at Pops, I see the grace of 50 kings rolled into the 6-foot frame of an athletic 90-year-old, although he claims to be shrinking. He still wakes up and uses his stationary bike for 30 minutes before he starts his day.
In 1965, Pops founded Sutter Hill Ventures, where he and his team funded hundreds of early-stage, high-tech companies making semiconductors, defibrillators, copy machines, operating systems, etc.
From 1981 to 1986, he left VC to serve as the Chairman of the Export-Import Bank of the U.S., upon the request of Ronald Reagan. He then jumped over to being Under-Secretary General of the United Nations, where
he ran the United Nations Development program and got to visit 110 countries to aid in their development. In 1994, he co- founded Draper International, the first U.S. venture capital fund to focus on investing in private companies with operations in India. In 2002, he co-founded Draper Richards LP, which invests in American early-stage tech companies, and he also founded Draper Investment Company, which concentrates on seed investments in Europe and Asia. Finally, he co-founded the Draper Richards Kaplan Foundation, the first “Social Entrepreneurship fund,” which backs nonprofits like their startups.
Today, people I’ve never met before sometimes tell me, “Your grandfather was such a great mentor to me!”
I’ve learned from hundreds of breakfasts with Pops that change is a constant, but core values are unstoppable. Even in the fast, ever-changing world of technology, some things don’t change. Pops has dropped the most amazing knowledge bombs on me (and many other people), particularly drilling down on the core elements that make up venture capital investing.
We both hope this handbook helps people who are starting out in early-stage VC: new angel investors, associates at venture funds, and all others who’ve found themselves holding what Pops always calls “the best job in the world.”