Episode 45: Keith Rabois - Managing Director at Khosla Ventures

**SPEAKER_1** (0:00)
This week on Generating Alpha, I sat down with Keith Rabois, one of the most influential operators, investors, and builders in Silicon Valley history. Keith is a managing director at Khosla Ventures and a founding member of the legendary PayPal Mafia. He's been instrumental in building some of the most important companies of our generation, serving as an early executive at PayPal and LinkedIn, and later as COO of Square during its hyper growth phase. As an investor, he's backed companies like Airbnb, DoorDash, YouTube, Yelp, Affirm, Ramp, among many others. For over two decades, he's operated the highest level of company building, product development, and venture capital, shipping entire markets and mentoring the next generation of founders. In our conversation, we talked about how Keith thinks about identifying and backing breakthrough companies, what he learned working alongside Peter Thiel, Elon Musk, and Jack Dorsey, the principles that separate world class operators from everyone else, his contrarian views on talent, culture, and scaling, and much more. If you enjoyed this episode, please follow the podcast and rate it a 5 stars on Spotify, subscribe on YouTube, and share it to anyone who you think might find it valuable. Thank you, and I hope you enjoy listening. Thanks, Keith, for coming on. I really appreciate it.

**SPEAKER_2** (1:15)
Pleasure to be with you.

**SPEAKER_1** (1:16)
Well, I want to start off where I always do, at the beginning. If I'm correct, you grew up in Edison, New Jersey. Tell me a little bit about your childhood, what your early environment looked like.

**SPEAKER_2** (1:26)
Yeah, that's true. I grew up in Edison, New Jersey. I spent the first 18 years of my life in New Jersey. I went to public schools in New Jersey. I thought I was on this pre-law, pre-political trajectory, so was pretty much intending to stay on a very conventional professional path and did all the things one does to get into a good college, all these extracurricular activities.
I probably was president of somewhere between three and seven different clubs simultaneously, and did a lot of debate and Model UN stuff, played some soccer, high school newspaper, blah, blah, blah, blah, blah. Crazy enough was even Treasurer of the French Honor Society. Everything from the sublime to the ridiculous.

**SPEAKER_1** (2:16)
After high school, you went out west to Stanford in the late 80s. During a very interesting time in Stanford history, during which the Stanford Review started, also during the tail end of the Cold War, where I'm sure many of those controversies got brought up on campus. I'm interested in just how that time shaped you as a person, how you got to meet those people early on at Stanford, that ultimately ended up working with the rest of your career. Tell me about that four years at Stanford.

**SPEAKER_2** (2:39)
Sure. I went to Stanford in the late 80s, finished in the early mid-90s and studied political science. On the Cold War stuff, interestingly enough, we were covering a lot of my majors was political science and strategic political science. We were covering a lot of debates about realism and idealism and liberalism, and how those should be applied to military doctrine in the Cold War, political doctrine and political competition with the Soviet Union. Obviously, a lot of that got obviated a few years later. Although the structural strategic planning elements of political science, Clausewitz, et cetera, are never out of date. The nuclear deterrent strategy and things like that still apply in many ways, like how to think through in more of a multi-power world than a bipolar world. But fundamentally, that stuff is really useful and still is. But again, I was calibrated towards like, how do I get into a really attractive law school as a high credentialist kid? I did get involved in the Stanford Review by accident. The first day, literally the first day of my freshman year, I was sitting in my freshman dorm room. This guy shows up and delivers what was actually the second edition of the Stanford Review, this is September 1988
I look at it and I'm like, what is this? There's some photo of like cartoonish photo of Ronald Reagan on the cover, I believe. It looks interesting. I started a conversation with the person who's hand delivering this to my dorm room, which is basically how content got delivered back then by all organizations, flyers, pamphlets, etc. It turned out this guy delivering to my dorm room was Peter Thiel.
So I got involved and recruited into the Stanford Review, started writing for the review, editing the review, spent many years of my career in college working on the review, writing for the review, editing the review, recruiting the review, but it's all very spontaneous. I got to know Peter quite well, mostly through the Stanford Review and other projects like that. Didn't really ever think it would evolve into a business kind of connection. Peter was on the fast track. He was about a few years older. I think he was a junior at the time, maybe he was a senior, and he was on the fast track to law school. He wound up attending Stanford Law School, clerking for an appellate court judge in the 11th Circuit, and then working at this law firm, Sullivan & Cromwell. I thought that was my also natural trajectory, and in fact, I followed most of that. I went to law school, clerked on the Fifth Circuit, which used to be part of the 11th Circuit, used to be part of the Fifth Circuit, so pretty similar. Wound up working at the exact same law firm of Sullivan & Cromwell. He was smart enough to quit after three months and five days, realized he didn't want to be a transactional attorney for the rest of his life. Probably fairly prescient. It took me three and a half years after clerking to figure out that I probably shouldn't be a litigator for the rest of my life, but eventually wound up in the same place.