Keith Rabois

117 statements across 14 episodes · 28 bullish · 20 bearish · 8 people on the record · first statement May 15, 2017 by Keith Rabois · said 174 times in 61 episodes since 2017 · across every show →

On the record as a speaker too: Keith Rabois's record, appearances and statements → this page counts the times other people say the name.

Mentions by year

brought up most by Harry Stebbings (97), Matteo Franceschetti (16), Jason Lemkin (9), Delian Asparouhov (8), Max Rhodes (7), Kevin Hartz (5), Winston Weinberg (4), Samir Vasavada (3)

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2026 12 mentions in 6 episodes 2 per episode
2025 20 mentions in 9 episodes 2 per episode
2024 80 mentions in 17 episodes 5 per episode
2023 23 mentions in 7 episodes 3 per episode
2022 22 mentions in 8 episodes 3 per episode
2021 10 mentions in 7 episodes 1 per episode
2020 3 mentions in 3 episodes 1 per episode
2019 2 mentions in 2 episodes 1 per episode
2018 1 mention in 1 episode
2017 1 mention in 1 episode

every mention, scene by scene, with the transcript →

Everything said about Keith Rabois, oldest first

May 15, 2017
Insight
Rabois: Investors begin losing touch with executive skills after four years
“I've been doing investing now professionally for four years, and at some point you start losing touch with the skills you used to have as a manager, as an executive, as a leader.”
Keith Rabois May 15, 2017 ▶ 19:18 20VC: Khosla's Keith Rabois on How To Create Sustainability Behind Growth, How To Assess The Potential Of Individuals & Teams & The Biggest Takeaways from LinkedIn, Paypal & Square
May 15, 2017 positive
Insight
Rabois: Startups with product-market fit should maximize growth speed
“Yeah, I'm not a big fan of the term sustained growth. I think you should take growth right away. When you have product market fit, you want to take advantage of that and really capture the value as much and as fast as you can. It's a very tumultuous world. Thi…”
Keith Rabois May 15, 2017 ▶ 12:27 20VC: Khosla's Keith Rabois on How To Create Sustainability Behind Growth, How To Assess The Potential Of Individuals & Teams & The Biggest Takeaways from LinkedIn, Paypal & Square
May 15, 2017
Insight
Rabois: Breakthrough ideas require teams to focus on a single priority
“You really do need people to focus on about one thing. If you want breakthrough ideas and tackling that breakthrough idea constantly, consistently, and not allowing them to get distracted with other initiatives.”
Keith Rabois May 15, 2017 ▶ 18:06 20VC: Khosla's Keith Rabois on How To Create Sustainability Behind Growth, How To Assess The Potential Of Individuals & Teams & The Biggest Takeaways from LinkedIn, Paypal & Square
May 15, 2017 positive
Disclosure
Rabois prefers backing startups at the pitch deck stage
“I decided to invest based upon a keynote deck, really, that these guys were going to reinvent healthcare, which sounds like ridiculous, but I like to invest in keynote decks, like Opendoor reinvested when it was just a keynote deck and a team, Ever Album, whic…”
Keith Rabois May 15, 2017 ▶ 28:50 20VC: Khosla's Keith Rabois on How To Create Sustainability Behind Growth, How To Assess The Potential Of Individuals & Teams & The Biggest Takeaways from LinkedIn, Paypal & Square
May 15, 2017 negative
Insight
Rabois: Startups should avoid general managers in favor of functional experts
“Some management lessons about avoiding general managers. We didn't really subscribe to the view that someone was a quote unquote good manager versus someone who was excellent in a particular discipline. And I think there's a lot of truth to that.”
Keith Rabois May 15, 2017 ▶ 9:21 20VC: Khosla's Keith Rabois on How To Create Sustainability Behind Growth, How To Assess The Potential Of Individuals & Teams & The Biggest Takeaways from LinkedIn, Paypal & Square
May 15, 2017
Insight
Rabois: Board members should not express opinions on every topic
“I don't think it's productive to have an opinion on everything. I think deciding where you have a competitive advantage based upon your experiences and skills and have a specific and unique insight where it's worth bringing to bear that skill to a Is a lot of …”
Keith Rabois May 15, 2017 ▶ 20:21 20VC: Khosla's Keith Rabois on How To Create Sustainability Behind Growth, How To Assess The Potential Of Individuals & Teams & The Biggest Takeaways from LinkedIn, Paypal & Square
May 15, 2017
Insight
Rabois: Replace executives whose personal growth lags company velocity
“When the individual's propensity to grow falls below the company's growth rate, I think you need to make a change.”
Keith Rabois May 15, 2017 ▶ 11:12 20VC: Khosla's Keith Rabois on How To Create Sustainability Behind Growth, How To Assess The Potential Of Individuals & Teams & The Biggest Takeaways from LinkedIn, Paypal & Square
May 15, 2017
Insight
Rabois: Top executives plan six months ahead of company needs
“When an executive is really performing, he or she is about six months ahead of the curve in terms of their plans, their initiatives, their thinking. When they're barely hanging on, they're delivering just in time, and obviously if they're not delivering, you c…”
Keith Rabois May 15, 2017 ▶ 11:41 20VC: Khosla's Keith Rabois on How To Create Sustainability Behind Growth, How To Assess The Potential Of Individuals & Teams & The Biggest Takeaways from LinkedIn, Paypal & Square
May 15, 2017
Insight
Rabois: Success is learned from winning teams, not analyzing failure
“I think you can learn from failure what not to do again, and that's probably worth learning, like repeating the same mistakes makes no sense, but you can't learn how to be successful just by avoiding mistakes. The way you learn how to be successful is just You…”
Keith Rabois May 15, 2017 ▶ 7:03 20VC: Khosla's Keith Rabois on How To Create Sustainability Behind Growth, How To Assess The Potential Of Individuals & Teams & The Biggest Takeaways from LinkedIn, Paypal & Square
May 15, 2017
Disclosure
Rabois meets most portfolio company CEOs in person every two weeks
“What I tend to do is I like to meet with most of the CEOs I work with about every two weeks in person, board meetings every, depending upon the maturity of the company, between once a month and once a quarter”
Keith Rabois May 15, 2017 ▶ 16:12 20VC: Khosla's Keith Rabois on How To Create Sustainability Behind Growth, How To Assess The Potential Of Individuals & Teams & The Biggest Takeaways from LinkedIn, Paypal & Square
May 15, 2017
Insight
Rabois: Dot-com bubble forced startups to hire non-tech talent
“I think there was so much hype and so much interest in technology and internet innovation that, and so many companies were being funded that the companies were desperate for talent. So they were willing to hire like people like me who might've had some skills,…”
Keith Rabois May 15, 2017 ▶ 4:04 20VC: Khosla's Keith Rabois on How To Create Sustainability Behind Growth, How To Assess The Potential Of Individuals & Teams & The Biggest Takeaways from LinkedIn, Paypal & Square
May 15, 2017
Insight
Rabois: Top performers often ignore past market downturn risks
“And maybe it makes you a little bit too cautious sometimes because you remember what can go wrong and maybe the people who do the best try to forget that.”
Keith Rabois May 15, 2017 ▶ 5:18 20VC: Khosla's Keith Rabois on How To Create Sustainability Behind Growth, How To Assess The Potential Of Individuals & Teams & The Biggest Takeaways from LinkedIn, Paypal & Square
May 15, 2017 negative
Insight
Rabois: VCs cannot succeed by focusing solely on winning investments
“I don't think you can do the just focus on your winners strategy. I think that causes real problems for you in the future as an investor, because by definition, the number of like non super successful companies you're going to invest in is greater than the num…”
Keith Rabois May 15, 2017 ▶ 15:26 20VC: Khosla's Keith Rabois on How To Create Sustainability Behind Growth, How To Assess The Potential Of Individuals & Teams & The Biggest Takeaways from LinkedIn, Paypal & Square
Sep 30, 2021 negative
Assertion Not checkable as stated
Rabois: Opendoor still executes its pricing model incorrectly eight years later
“The one that I still make fun of JD about is how we did our pricing model, which we still basically don't do correctly. You know, eight years later, we'll eventually fix this, but there's a lot of debate about whether we should have consumers name their own pr…”
Keith Rabois Sep 30, 2021 ▶ 16:20 20VC: The Opendoor Memo: Keith Rabois on The Origins of Opendoor from a Conversation with Peter Thiel, Why Cash is Not a Competitive Moat for Startups Today and What People Misunderstand About Black Swan Events in Real Estate and How it Impacts Opendoor
Sep 30, 2021 positive
Insight
Rabois: Eight hours of sleep is the most important decision for success
“I've always prioritized eight hours sleep in my life. I think it's the most important sort of decision. You can make in terms of health, happiness, professional success.”
Keith Rabois Sep 30, 2021 ▶ 32:22 20VC: The Opendoor Memo: Keith Rabois on The Origins of Opendoor from a Conversation with Peter Thiel, Why Cash is Not a Competitive Moat for Startups Today and What People Misunderstand About Black Swan Events in Real Estate and How it Impacts Opendoor
Sep 30, 2021
Disclosure
Thiel offered $5M in 2003 to fund Opendoor's predecessor
“Peter was willing to fund the company with about five million dollars, but fundamentally, to buy enough homes and prove that you could accurately price the homes, five million was at the very low end of what would be feasibly, statistically, to prove that we c…”
Keith Rabois Sep 30, 2021 ▶ 5:16 20VC: The Opendoor Memo: Keith Rabois on The Origins of Opendoor from a Conversation with Peter Thiel, Why Cash is Not a Competitive Moat for Startups Today and What People Misunderstand About Black Swan Events in Real Estate and How it Impacts Opendoor
Sep 30, 2021
Assertion Supported
Rabois: Opendoor negotiated its second funding round before launching
“So we wound up negotiating the second round pretty much before we actually launched the company.”
Keith Rabois Sep 30, 2021 ▶ 23:04 20VC: The Opendoor Memo: Keith Rabois on The Origins of Opendoor from a Conversation with Peter Thiel, Why Cash is Not a Competitive Moat for Startups Today and What People Misunderstand About Black Swan Events in Real Estate and How it Impacts Opendoor
Sep 30, 2021 neutral
Disclosure
Rabois: Opendoor pursued a SPAC under the misconception it was faster
“The real reason for choosing to go down the SPAC model was I wanted us to be a public company as fast as humanly possible. I had some reasons to believe we could do it a little bit more rapidly through a SPAC. The truth is that's not really true, but it was ea…”
Keith Rabois Sep 30, 2021 ▶ 27:10 20VC: The Opendoor Memo: Keith Rabois on The Origins of Opendoor from a Conversation with Peter Thiel, Why Cash is Not a Competitive Moat for Startups Today and What People Misunderstand About Black Swan Events in Real Estate and How it Impacts Opendoor
May 30, 2022 negative
Disclosure
Rabois: Passing on an early Coinbase meeting was a massive mistake
“Is this the, you know, whatever, let's say Coinbase that I, you know, was introduced to very, very early by Gary, who really, Gary Tan, who really wanted me to invest. And, you know, I basically wrote back. I really didn't want to meet them, even though I actu…”
Keith Rabois May 30, 2022 ▶ 31:03 Keith Rabois: The End of Woke Capitalism; Time Allocation Tips; Silicon Valley vs Miami | 20VC #891 · 20VC with Harry Stebbings
May 30, 2022
Disclosure
Rabois: Airbnb is likely his single best-returning investment
“I've never actually exactly tracked it, but probably Airbnb.”
Keith Rabois May 30, 2022 ▶ 38:18 Keith Rabois: The End of Woke Capitalism; Time Allocation Tips; Silicon Valley vs Miami | 20VC #891 · 20VC with Harry Stebbings
May 30, 2022
Prediction Not checkable as stated
Rabois will quit VC if he loses his founder signal
“As soon as I feel I've lost that ability, I'm gonna have to quit.”
Keith Rabois May 30, 2022 ▶ 36:27 Keith Rabois: The End of Woke Capitalism; Time Allocation Tips; Silicon Valley vs Miami | 20VC #891 · 20VC with Harry Stebbings
May 30, 2022 negative
Opinion
Rabois: Building a tech company in Silicon Valley is an active disadvantage
“And I now believe Silicon Valley is a disadvantage not even neutral, it's an actual disadvantage.”
Keith Rabois May 30, 2022 ▶ 27:48 Keith Rabois: The End of Woke Capitalism; Time Allocation Tips; Silicon Valley vs Miami | 20VC #891 · 20VC with Harry Stebbings
May 30, 2022 neutral
Insight
Rabois: Early-stage VCs must depend on downstream funding rounds
“Any early stage investor, unless they have running a billion dollar plus fund, Has to depend on future financings. Almost no company you or I will ever finance will be profitable on the first tranche of investment.”
Keith Rabois May 30, 2022 ▶ 2:44 Keith Rabois: The End of Woke Capitalism; Time Allocation Tips; Silicon Valley vs Miami | 20VC #891 · 20VC with Harry Stebbings
May 30, 2022 negative
Assertion Not checkable as stated
Rabois: Series C and late-stage VCs lack asymmetric information
“Typically people who are leading these series C and later rounds have no asymmetry of information. They may have asymmetry of closing. Asymmetry of deal flow, but there's no asymmetry of information.”
Keith Rabois May 30, 2022 ▶ 2:14 Keith Rabois: The End of Woke Capitalism; Time Allocation Tips; Silicon Valley vs Miami | 20VC #891 · 20VC with Harry Stebbings
May 30, 2022 positive
Disclosure
Rabois: Founders Fund never replaces founders or forces management changes
“Founders fund, there's only one real answer because we don't replace founders. Most VCs would probably try to change the management team, including the CEO. We, you know, ideologically, philosophically, and effectively, legally just don't do that.”
Keith Rabois May 30, 2022 ▶ 15:47 Keith Rabois: The End of Woke Capitalism; Time Allocation Tips; Silicon Valley vs Miami | 20VC #891 · 20VC with Harry Stebbings
May 30, 2022 bearish
Assertion Not checkable as stated
Rabois and Peter Thiel foresaw the tech market crash in 2021
“Peter and I figured out this market was crashing last summer, and we really tried to stop people from investing at ridiculous prices, but even the founders thought we weren't totally successful.”
Keith Rabois May 30, 2022 ▶ 20:48 Keith Rabois: The End of Woke Capitalism; Time Allocation Tips; Silicon Valley vs Miami | 20VC #891 · 20VC with Harry Stebbings
May 30, 2022
Insight
Rabois: Half of a VC's peers should laugh at their best investments
“My asset test for success as a VC is do half of my friends who are VCs laugh at my investments.”
Keith Rabois May 30, 2022 ▶ 24:48 Keith Rabois: The End of Woke Capitalism; Time Allocation Tips; Silicon Valley vs Miami | 20VC #891 · 20VC with Harry Stebbings
May 30, 2022
Disclosure
Rabois led 14 investments in 2021, but zero in H1 2022
“So I led 13 or 14 new investments or so plus or minus in 21. None, you know, basically halfway through 20, 22.”
Keith Rabois May 30, 2022 ▶ 41:00 Keith Rabois: The End of Woke Capitalism; Time Allocation Tips; Silicon Valley vs Miami | 20VC #891 · 20VC with Harry Stebbings
May 30, 2022 bullish
Prediction Didn’t hold up
Rabois will now exclusively invest in in-person startups
“I really want to invest in only companies that are in person. So I think there's a lot of alpha there. I think in-person companies will be the successful startups. I only want to find founders who are working in person and that's my new investment filter.”
Keith Rabois May 30, 2022 ▶ 26:42 Keith Rabois: The End of Woke Capitalism; Time Allocation Tips; Silicon Valley vs Miami | 20VC #891 · 20VC with Harry Stebbings
May 30, 2022 neutral
Disclosure
Rabois has only led three late-stage investment rounds in nine years
“I've only led in nine years of investing three late stage rounds later stage rounds, series C co-led with Stripe fares series C. I led a founder's fund. And then I invest a lot of money in two late-stage rounds in a company called Ultima”
Keith Rabois May 30, 2022 ▶ 8:09 Keith Rabois: The End of Woke Capitalism; Time Allocation Tips; Silicon Valley vs Miami | 20VC #891 · 20VC with Harry Stebbings
May 30, 2022 negative
Insight
Rabois: Compressed benchmark comps break mid-stage venture valuation math
“I think you do need to think through the market comps. So I think one of the mistakes people have been making over the last shoot, three years is let's say if Shopify is trading at one hundred sixty billion, let's say, then the upside case for things that coul…”
Keith Rabois May 30, 2022 ▶ 6:36 Keith Rabois: The End of Woke Capitalism; Time Allocation Tips; Silicon Valley vs Miami | 20VC #891 · 20VC with Harry Stebbings
May 30, 2022
Assertion Not checkable as stated
Rabois almost never regrets passing on founders he meets in person
“I own basically almost never, possibly never have made a mistake in passing on a founder. I met a person.”
Keith Rabois May 30, 2022 ▶ 29:50 Keith Rabois: The End of Woke Capitalism; Time Allocation Tips; Silicon Valley vs Miami | 20VC #891 · 20VC with Harry Stebbings
May 30, 2022 neutral
Prediction Not checkable as stated
Rabois: Founders Fund gives years of warning before stopping follow-on funding
“I think we'll, we'll be clear that like, look, I wouldn't count on us for additional capital. If there's things we can do to be helpful, you know, we'll, we'll try, but like, we'll give them, you know, a significant advance warning. Let's call it measured in y…”
Keith Rabois May 30, 2022 ▶ 16:15 Keith Rabois: The End of Woke Capitalism; Time Allocation Tips; Silicon Valley vs Miami | 20VC #891 · 20VC with Harry Stebbings
May 30, 2022 negative
Insight
Rabois: Public market comps are irrelevant for seed and Series A
“Most of what I've been successful at are really seed and series A investments, in which case the public comp rules don't really matter, and I don't pay too much attention to them.”
Keith Rabois May 30, 2022 ▶ 7:36 Keith Rabois: The End of Woke Capitalism; Time Allocation Tips; Silicon Valley vs Miami | 20VC #891 · 20VC with Harry Stebbings
May 30, 2022 neutral
Assertion Supported
Rabois: VC investments take 10 to 20 years to reach profitability
“Actually some have, you know, like I'm sure Opendoor actually is profitable, a firm will be profitable, but usually it's a 10 to 15, 20 year journey by the time that happens.”
Keith Rabois May 30, 2022 ▶ 3:16 Keith Rabois: The End of Woke Capitalism; Time Allocation Tips; Silicon Valley vs Miami | 20VC #891 · 20VC with Harry Stebbings
Jun 29, 2022
Assertion Not publicly verifiable
Rabois: Thiel and I saw market crash coming in summer 2021
“Both Peter and I figured out this market was crashing last summer, and we really tried to stop people from investing at ridiculous prices, but even a founder's fund, we weren't totally successful.”
Keith Rabois Jun 29, 2022 ▶ 8:54 20VC: The Memo: Bill Gurley, Doug Leone, Keith Rabois; Investing Lessons from Prior Busts, How Their Investor Psychology Changed, What Can Be Applied To Today's Market
Aug 9, 2023 positive
Assertion Partly supported
Lemkin: Top VCs have made their best investments from cold inbound pitches
“They all have done some of their best investments from cold inbound. All of them.”
Jason Lemkin Aug 9, 2023 ▶ 20:16 Jason Lemkin: Every VC has a FRAUD in their portfolio; The IPO market is about to EXPLODE | E1046 · 20VC with Harry Stebbings
Nov 20, 2023 positive
Disclosure
Franceschetti: Everything at Eight Sleep is public internally except compensation
“Everything is, everything, this is another rule from Keith, I think, from the, his time at Square, where, so essentially everything is public in our company except comp. Usually comp, you don't want to share it, but everything else is shared.”
Matteo Franceschetti Nov 20, 2023 ▶ 1:15:03 Matteo Franceschetti: The Ultimate Hiring Playbook: Five Questions to Ask Every New Hire | E1084 · 20VC with Harry Stebbings
Nov 20, 2023 positive
Opinion
Franceschetti: Paul Graham and Keith Rabois excel at explaining complex ideas simply
“You see people like Paul Graham or Keith or Boyce, right? They are some of the greatest at expressing a very complicated concept with few words in something that I call it the grammar rule by something that my grandma could understand.”
Matteo Franceschetti Nov 20, 2023 ▶ 29:14 Matteo Franceschetti: The Ultimate Hiring Playbook: Five Questions to Ask Every New Hire | E1084 · 20VC with Harry Stebbings
Nov 20, 2023
Insight
Franceschetti: A company's project capacity equals its number of 'barrel' leaders
“Output usually is a function of how many barrels you have. Barrels are people in your company that can get everything done from zero to completion, right? And you have barrels and ammunition. Barrels can lead anything from zero to completion. Ammunition suppor…”
Matteo Franceschetti Nov 20, 2023 ▶ 34:52 Matteo Franceschetti: The Ultimate Hiring Playbook: Five Questions to Ask Every New Hire | E1084 · 20VC with Harry Stebbings
Nov 27, 2023 negative
Insight
Keith Rabois advises VCs against simultaneously acting as company founders
“So there are real, real trade-offs to company building. I would not recommend that.”
Keith Rabois Nov 27, 2023 ▶ 17:12 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Nov 27, 2023 bullish
Opinion
Rabois calls Airbnb the best network effect business he's ever seen
“They have the best network effect business I've ever seen.”
Keith Rabois Nov 27, 2023 ▶ 1:01:05 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Nov 27, 2023
Insight
Rabois: Startups must reset to zero-and-zero after every success
“You know, one metaphor I like to use for this is like, imagine you're playing in a like football, let's say in America, you win the Superbowl. But your own, you have to go back preseason, start all over in training camp, and your record's zero and zero again, …”
Keith Rabois Nov 27, 2023 ▶ 33:55 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Nov 27, 2023
Assertion Not checkable as stated
Rabois: Over 80% of successful startups possess extreme work ethics
“I wouldn't say it's necessarily all of them universally, but more than 80%. It's a very Common characteristic of successful companies.”
Keith Rabois Nov 27, 2023 ▶ 4:14 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Nov 27, 2023 positive
Insight
Rabois: Intellectual preparation during downtime drives breakthrough workplace success
“You don't just go to the field and practice all day, 24 seven. You might study film, and like, you might go home and spend four hours watching video of your opponent, and that makes you more successful. So your body is recovering, your, like, your brain is tra…”
Keith Rabois Nov 27, 2023 ▶ 12:58 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Nov 27, 2023
Disclosure
Rabois: Taking eight years off operating caused severe executive skill atrophy
“Like I took eight years between square and taking over, you know, CEO of open store. It's like muscle atrophy, you know, kind of going with the same metaphor. And it took me the first year at least to get back to be decent as a CEO.”
Keith Rabois Nov 27, 2023 ▶ 17:50 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Nov 27, 2023
Insight
Rabois: Spotting Great Investors Is Harder Than Finding Great Founders
“Projecting who's likely to be a great investor is even harder than figuring out who's going to be a world-class founder.”
Keith Rabois Nov 27, 2023 ▶ 1:04:02 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Nov 27, 2023
Insight
Rabois: Having Kids Forces Time Discipline and Amplifies Professional Success
“So you can be very successful if you have kids. You know, there's touring artists and music that have kids. It requires you to be more disciplined, like about your time allocation. It tends to amplify things if you're really disciplined, maybe even do better w…”
Keith Rabois Nov 27, 2023 ▶ 36:48 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Nov 27, 2023 bearish
Opinion
Rabois: There are currently very few great startups worth investing in
“Well, I'm optimistic. I just don't believe there's a lot of great startups to invest in as a VC. Those are two different things. Like generally you have to be a technology optimist is, you know, Mark adjacent pointed out to be a successful investor. You always…”
Keith Rabois Nov 27, 2023 ▶ 1:03:02 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Nov 27, 2023 bearish
Prediction Not checkable as stated
Rabois: Airbnb founders would not start a remote company today
“And if you ask Brian or Joe, would you start a company from scratch today as a new founder? I can guarantee what that answer is. It's not going to be doing remotely.”
Keith Rabois Nov 27, 2023 ▶ 1:01:10 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Nov 27, 2023 neutral
Insight
Rabois: Open-source companies are rare exceptions for remote work success
“I think you can build an open source company predicated on open source software in a distributor way and distribute away because you have thousands of contributors or hundreds of contributors all around the globe to open source software and you're managing and…”
Keith Rabois Nov 27, 2023 ▶ 1:00:10 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Nov 27, 2023
Insight
Rabois: Every successful company operates as a unique cult
“Every company that's successful is like a cult and every cult that works is unique. And so if you just take general feedback and apply it to a unique situation, it can often be, you know, bad, like really bad.”
Keith Rabois Nov 27, 2023 ▶ 51:05 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Nov 27, 2023
Insight
Rabois: Executive Performance Is Obvious Within 30 Days
“Whereas like an executive, I always know in 30 days whether they're really going to work.”
Keith Rabois Nov 27, 2023 ▶ 1:05:04 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Nov 27, 2023 negative
Disclosure
Rabois: I was too passive in setting OpenStore's culture my first year
“I was a little too, I was a lot too passive in letting the culture formulate in the first year, and I really have struggled to fix that.”
Keith Rabois Nov 27, 2023 ▶ 45:52 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Nov 27, 2023 positive
Opinion
Rabois: First-time founders are on average better than repeat founders
“I think first time founders are actually better on average. Most of the best companies I've invested in are first time founders, not all.”
Keith Rabois Nov 27, 2023 ▶ 44:30 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Nov 27, 2023
Insight
Rabois: Essential Success Traits Are Formed and Evident Early in Life
“Almost every trait That's important. You develop early in your life, and there's evidence of it. So like work ethic, intensity, resilience, resourcefulness, it shows up very, very early.”
Keith Rabois Nov 27, 2023 ▶ 42:59 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Nov 27, 2023 neutral
Disclosure
Rabois: I almost never tell portfolio founders what to do
“I don't expect founders to listen to me, by the way, just to be clear. I almost never tell a founder what to do. I do have feedback and hopefully insightful feedback about my kind of spidey sense of what's working and what's not.”
Keith Rabois Nov 27, 2023 ▶ 48:51 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Nov 27, 2023
Assertion Not checkable as stated
Rabois: Successful DJs Play 300 Shows a Year Before Making It
“Most of the successful DJs I know play like 300 shows a year. Across the world until they make it. And when they make it, they still play a 150 shows a year, traveling all around the globe.”
Keith Rabois Nov 27, 2023 ▶ 8:43 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Nov 27, 2023 neutral
Insight
Rabois: World-class Series A venture capitalists are only right 40% of the time
“If you're world-class, you're right, 40% of the time. And I define venture as heat stage investing, series A investing. 40%, Hall of Fame, Ted Williams, tech category. So, my definition, 40% right is going to lead to 60% not being right.”
Keith Rabois Nov 27, 2023 ▶ 47:55 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Nov 27, 2023
Insight
Rabois: Venture capitalists know within 12 months if an investment is successful
“So, I actually think within 12 months, 90%, 99% of the time, you know whether you've made a good investment, even if the external world doesn't know.”
Keith Rabois Nov 27, 2023 ▶ 1:05:36 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Nov 27, 2023
Insight
Rabois: Founders should operate like Navy SEALs, not the Army
“He actually did give a metaphor of like, I'm operating more like the army where the army is like very much like operational efficient across everything. No, no mistakes. Whereas what I should be doing as a founder is being more like a Navy seal, like going all…”
Mike Shebat Nov 27, 2023 ▶ 46:57 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Nov 27, 2023 bearish
Prediction Open · timeframe Nov 2033
Rabois: Structural inflation will keep interest rates high for a decade
“They're not going much down. I mean, I think we have sustained inflation for structural reasons for a decade. Yeah. Plus or minus, they might be slightly alleviated, but there's a lot of very strong reasons why this zero interest rate or low interest rate envi…”
Keith Rabois Nov 27, 2023 ▶ 1:02:32 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Nov 27, 2023
Assertion Not checkable as stated
Keith Rabois Billed 360 Hours in One Month as Law Associate
“So I remember when I was a lawyer, the last month I was a litigator at Sullivan and Commonwealth in New York. I billed 360 hours. I bet you almost nobody works in the startups, works 300 or 60 hours. That's billed, by the way, not worked.”
Keith Rabois Nov 27, 2023 ▶ 36:23 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Nov 27, 2023
Insight
Rabois: Culture Hardens Like Concrete and Becomes Painful to Fix Later
“Culture is like concrete and in liquid form. Concrete's really valuable, but once it solidifies, it takes like a jackhammer, which is incredibly disruptive, painful, expensive, to break.”
Keith Rabois Nov 27, 2023 ▶ 45:38 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Nov 27, 2023 negative
Insight
Rabois: Founders should never practice their pitches with mediocre investors
“I think we need to, I don't think you should practice your pitch with mediocre investors, because really good investors are going to ask completely different questions.”
Keith Rabois Nov 27, 2023 ▶ 0:03 Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
Jan 12, 2024 positive
Insight
Rabois: Most technology startups are better off going public early
“I'm going to get, I believe that most companies, you know, and I have a chapter in Eli Gill's high growth handbook on the topic in a fairly lengthy core answer as well on, I believe most companies are better Off going public early period.”
Keith Rabois Jan 12, 2024 ▶ 1:11:08 Keith Rabois on Rejoining Khosla Ventures | E1102 · 20VC with Harry Stebbings
Jan 12, 2024 negative
Opinion
Rabois: Europe is economically stagnant and functions as a museum
“You know, Larry Stummer's quote is still pretty good that Europe's a museum. I think that's probably pretty apt.”
Keith Rabois Jan 12, 2024 ▶ 1:13:59 Keith Rabois on Rejoining Khosla Ventures | E1102 · 20VC with Harry Stebbings
Jan 12, 2024
Assertion Not checkable as stated
Roelof Botha: Deciding which first meetings to take is VC's hardest part
“Roloff mentioned this to me. I remember talking to him a year after he joined Sequoia. It was probably like 2004 and we had coffee and I said, what's the hardest part of the job? And he said, deciding which first meetings to take.”
Keith Rabois Jan 12, 2024 ▶ 1:13:07 Keith Rabois on Rejoining Khosla Ventures | E1102 · 20VC with Harry Stebbings
Jan 12, 2024
Disclosure
Rabois: Passed on Robinhood seed after Khosla banned seed board seats
“I had already, like, locked in a turn sheet to lead the series seat for Robin Hood chilling at 20 post, which was pretty expensive, but they came back and Really wanted me to join the board in the seed round, and this was in maybe my second year at KB, so I as…”
Keith Rabois Jan 12, 2024 ▶ 11:57 Keith Rabois on Rejoining Khosla Ventures | E1102 · 20VC with Harry Stebbings
Jan 12, 2024 positive
Assertion Contradicted
Rabois: I have never passed on a multi-billion dollar founder
“Once you get me in the room with founders, I've made those calls really, really well. Like I was mentioning the other day that I'm not sure I've ever passed on somebody that's turned out to be building a multi-billion dollar company, but I have definitely decl…”
Keith Rabois Jan 12, 2024 ▶ 1:12:12 Keith Rabois on Rejoining Khosla Ventures | E1102 · 20VC with Harry Stebbings
Jan 12, 2024
Insight
Rabois: Multi-stage venture investors cannot constantly join seed-stage boards
“You cannot be an institutional investor in a multistage fund, constantly joining boards at Seed, so you have to be very judicious, so the feedback wasn't wrong, it was just wrong as applied to that company.”
Keith Rabois Jan 12, 2024 ▶ 12:38 Keith Rabois on Rejoining Khosla Ventures | E1102 · 20VC with Harry Stebbings
Jan 12, 2024
Disclosure
Rabois: Lost two-thirds of missed deals to the same competitors
“In about 11 years doing this, I think there's somewhere between five or six or so term sheets I've extended where I didn't close them, like I lost to somebody, and the reality is that four of the sticks, or two thirds of them, are the same, are to the same peo…”
Keith Rabois Jan 12, 2024 ▶ 29:39 Keith Rabois on Rejoining Khosla Ventures | E1102 · 20VC with Harry Stebbings
Jan 12, 2024 neutral
Assertion Not checkable as stated
Rabois: Bitcoin adoption is inversely correlated with the rule of law
“So my theory was always from 2013 or 14 that adoption of Bitcoin would globally be inversely correlated to the rule of law in a specific market or specific country. And I think that's proven to be true.”
Keith Rabois Jan 12, 2024 ▶ 1:08:12 Keith Rabois on Rejoining Khosla Ventures | E1102 · 20VC with Harry Stebbings
Jan 12, 2024 neutral
Opinion
Rabois wants his children to have the work ethic of having nothing
“I want them to have the work ethic of someone who has nothing.”
Keith Rabois Jan 12, 2024 ▶ 1:05:45 Keith Rabois on Rejoining Khosla Ventures | E1102 · 20VC with Harry Stebbings
Jan 12, 2024 bullish
Insight
Rabois: Venture funds should make ad hoc follow-on decisions, not reserve
“You're probably better off not reserving, and then making ad hoc decisions based upon the quality of that particular opportunity, which includes who's the investor, what's the traction of the company, what do we believe about the founder, what have we learned …”
Keith Rabois Jan 12, 2024 ▶ 21:16 Keith Rabois on Rejoining Khosla Ventures | E1102 · 20VC with Harry Stebbings
Jan 12, 2024 bearish
Prediction Didn’t hold up
Rabois: Donald Trump will not win the 2024 Republican presidential nomination
“You know, as you've probably seen on Twitter, I don't even believe he's gonna be the Republican nominee for president.”
Keith Rabois Jan 12, 2024 ▶ 1:09:17 Keith Rabois on Rejoining Khosla Ventures | E1102 · 20VC with Harry Stebbings
Jan 12, 2024
Assertion Not checkable as stated
Rabois: Most VCs are terrified to invest based on slides alone
“Most investors are terrified of assessing a team and a keynote deck and handing over one, two, three, four, five million dollars.”
Keith Rabois Jan 12, 2024 ▶ 27:01 Keith Rabois on Rejoining Khosla Ventures | E1102 · 20VC with Harry Stebbings
Jan 12, 2024 positive
Assertion Not checkable as stated
Rabois: I can win 100% of the seed deals I target
“At seed, I can probably close a hundred percent of the things I want to invest in if I want to.”
Keith Rabois Jan 12, 2024 ▶ 30:45 Keith Rabois on Rejoining Khosla Ventures | E1102 · 20VC with Harry Stebbings
Jan 12, 2024 positive
Insight
Rabois: Board members should probe founders with questions, not prescribe answers
“As a board member, one of the best ways is to ask things in terms of questions, not in terms of answers. So you probe by questions, because then you're never leading. You may be leading a little bit, but you're never prescribing, and it's a very big difference…”
Keith Rabois Jan 12, 2024 ▶ 57:13 Keith Rabois on Rejoining Khosla Ventures | E1102 · 20VC with Harry Stebbings
Jan 12, 2024 positive
Assertion Supported
Rabois: Vinod Khosla published papers on AI replacing doctors before 2013
“He was on the, you know, the AI crusade before I even joined KV in 2013. He published papers about, you know, how AI was going to replace doctors in medicine, and this is like before I joined KV, so way ahead of the curve.”
Keith Rabois Jan 12, 2024 ▶ 1:01:57 Keith Rabois on Rejoining Khosla Ventures | E1102 · 20VC with Harry Stebbings
Jan 12, 2024
Insight
Rabois: Startups solidify like concrete post-Series B, making changes painful
“So, early stage companies, it's kind of like liquid concrete. It's very valuable. And then it solidifies. Post Series B, it's totally solidified. And if you want to change something, you know, that's concrete, you have to mold this jackhammer, which is incredi…”
Keith Rabois Jan 12, 2024 ▶ 27:23 Keith Rabois on Rejoining Khosla Ventures | E1102 · 20VC with Harry Stebbings
Jan 12, 2024
Disclosure
Rabois: Lost Rippling seed to Gary Tan over $10M valuation gap
“Rickling came in, Parker came in and we gave a term sheet. It was, you know, obviously controversial at the time, for the seed, and Gary Tan, initialized, also gave a term sheet. And at the time, there was about a ten million dollar gap. I probably offered fiv…”
Keith Rabois Jan 12, 2024 ▶ 11:05 Keith Rabois on Rejoining Khosla Ventures | E1102 · 20VC with Harry Stebbings
Jan 12, 2024
Disclosure
Rabois: Avoided launching a solo fund due to administrative drag coefficient
“Over the years, and I'd say over the fifteen-year time horizon, the last 15 years of my life, I have occasionally thought about, should I start a fund? There's definitely a lot of drag coefficient associated with that that I was not particularly excited with, …”
Keith Rabois Jan 12, 2024 ▶ 49:24 Keith Rabois on Rejoining Khosla Ventures | E1102 · 20VC with Harry Stebbings
Jan 12, 2024 neutral
Insight
Rabois: Venture funding rounds act like poker cards providing priced information
“It's like playing poker, and every round is like a card you're being dealt, and there's different informational content, and there's a different price point for that round, so what's the information you get from that new card, and then what's the price?”
Keith Rabois Jan 12, 2024 ▶ 22:40 Keith Rabois on Rejoining Khosla Ventures | E1102 · 20VC with Harry Stebbings
Jan 12, 2024 bullish
Disclosure
Rabois: Opendoor required a $10M seed round to prove unit economics
“We raised 10 of the seed for Opendoor. That was actually the correct dose. Buying homes, you really can't prove that you can buy cohorts of homes accurately, like priced accurately and resold properly in less, for less than about ten million.”
Keith Rabois Jan 12, 2024 ▶ 26:05 Keith Rabois on Rejoining Khosla Ventures | E1102 · 20VC with Harry Stebbings
Jan 12, 2024
Disclosure
Rabois: Hid Faire seed board seat from Khosla partners for a year
“Fair came back and said, Max said to me, you know, we chatted, I chatted with my co-founders, and, you know, we'll say yes, but you have to join the board, and having learned and been burned by the Robinhood experience, I never really told my partners that I w…”
Keith Rabois Jan 12, 2024 ▶ 13:12 Keith Rabois on Rejoining Khosla Ventures | E1102 · 20VC with Harry Stebbings
Jan 12, 2024
Assertion Not checkable as stated
Rabois: Founders Fund partners operated like independent PMs without collective debate
“Founders Fund, especially when I joined, was very much people running their own investment strategies. Think of it as like a PM running their own investment strategies, and there's a way of syncing and getting a certain number of critical mass and votes to sup…”
Keith Rabois Jan 12, 2024 ▶ 6:13 Keith Rabois on Rejoining Khosla Ventures | E1102 · 20VC with Harry Stebbings
Jan 12, 2024
Insight
Rabois: Sponsoring non-standard venture deals consumes internal social capital
“If I want to do something that's very not standard or very controversial or not expected, I'm kind of burning and consuming some social capital. Now, if I make the right call that That gets paid back with interest, and you know, the next time I want to make a …”
Keith Rabois Jan 12, 2024 ▶ 8:06 Keith Rabois on Rejoining Khosla Ventures | E1102 · 20VC with Harry Stebbings
May 3, 2024
Insight
Rabois: Organizational structures inevitably fail when headcount grows tenfold
“What worked historically sometimes often doesn't work when you multiply the number of people by three, four or five, and it definitely doesn't work when you multiply the number of people by 10.”
Keith Rabois May 3, 2024 ▶ 16:25 Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148 · 20VC with Harry Stebbings
May 3, 2024
Insight
Rabois: A CEO is ultimately responsible for all results and cannot abdicate
“Ultimately CEO is ultimately responsible for everything. There's no excuses. So you can't ever abdicate. There's no such thing as like, I let this person do X, but I'm not responsible for the results when you're CEO.”
Keith Rabois May 3, 2024 ▶ 22:10 Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148 · 20VC with Harry Stebbings
May 3, 2024
Insight
Rabois: A single bad executive hire can destroy a startup's momentum
“It'd be like a topic in itself, but actually, so whereas most wrong as an executive would be on hires, like, you know, one bad hire, just one. Can really set back an organization and undermine the momentum pretty severely.”
Keith Rabois May 3, 2024 ▶ 28:43 Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148 · 20VC with Harry Stebbings
May 3, 2024 positive
Assertion Not checkable as stated
Rabois: Ramp's 2018 pitch notes match its current board discussions
“And if you read the notes today, it is literally just like the board meeting we just finished with the exception of AI. We didn't really talk about it at AI, but everything else in the board meeting today is like, Right on target from this first note in maybe …”
Keith Rabois May 3, 2024 ▶ 1:55 Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148 · 20VC with Harry Stebbings
May 3, 2024
Disclosure
Rabois: I don't build underwriting spreadsheets or target 3x-5x multiples
“I don't like build spreadsheets and I try to underwrite to three X, four X, five X, not what I do at least.”
Keith Rabois May 3, 2024 ▶ 42:44 Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148 · 20VC with Harry Stebbings
May 3, 2024 positive
Insight
Glyman: Mapping business equations creates operational focus and enables rapid scaling
“He talks about this concept of, can you really articulate cleanly your business equations? What are the outputs you're trying to drive? What are the inputs in your business? Can you list that very clearly and map that? And that exercise of mapping, how does ou…”
Eric Glyman May 3, 2024 ▶ 8:14 Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148 · 20VC with Harry Stebbings
May 3, 2024
Disclosure
Rabois: I rebuild my calendar weekly to eliminate unwanted obligations
“Sorry, I don't really have, I like try to redo my calendar every week, so there shouldn't be anything on there that I don't want to be doing.”
Keith Rabois May 3, 2024 ▶ 40:47 Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148 · 20VC with Harry Stebbings
May 3, 2024
Insight
Rabois: Executive capacity for direct reports depends heavily on domain expertise
“Actually, as an executive, when you know certain content areas, subject matters, and, like, you have some ability in that craft, it's a hell of a lot easier to have a direct report there, because you're diving in really quickly to what's key. When you have to …”
Keith Rabois May 3, 2024 ▶ 41:26 Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148 · 20VC with Harry Stebbings
May 3, 2024
Insight
Rabois: Leaders must vary micromanagement based on task maturity and risk
“You actually want to be inconsistent on this, whether you're like quote unquote micromanaging or you're giving a lot of rope because it depends on the task relevant maturity of the person and the project and the consequences to the business.”
Keith Rabois May 3, 2024 ▶ 21:20 Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148 · 20VC with Harry Stebbings
May 3, 2024
Assertion Partly supported
Rabois: PayPal had virtually no successful external executive hires
“And this was definitely the PayPal model. We basically had no external hires that thrived, and so everybody was internally groomed from within.”
Keith Rabois May 3, 2024 ▶ 19:07 Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148 · 20VC with Harry Stebbings
May 3, 2024 positive
Assertion Partly supported
Rabois: Ramp launched card issuing in 50 days versus typical 6-12 months
“So there's a lot of complexity in setting up issuing cards, just the very basic fundamentals usually take an infinite amount of time. Usually six to 12 months is pretty good as someone who's been involved in companies like this for like 20 years. I think Eric …”
Keith Rabois May 3, 2024 ▶ 14:23 Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148 · 20VC with Harry Stebbings
May 3, 2024 neutral
Insight
Rabois: Founders must invert inertia to manually create startup momentum
“A lot of company building is you want to tap into a vein. Like inertia is not your friend. When you start a company, Everything. Time's not your friend. The world doesn't care about you. You have to invert, literally invert inertia. So you have to create momen…”
Keith Rabois May 3, 2024 ▶ 25:17 Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148 · 20VC with Harry Stebbings
May 3, 2024
Insight
Rabois: Artificial startup momentum works initially but cannot scale forever
“I think you can sort of pseudo hack your way into momentum. You can't scale it forever. If you're really hacking it, you're going to have to make the train tracks real, and you're going to have to make the engine that propels things pretty real at some point.”
Keith Rabois May 3, 2024 ▶ 26:18 Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148 · 20VC with Harry Stebbings
May 3, 2024 positive
Insight
Rabois: Starting with a focused product is better than launching a platform
“I think generally you start with product is a much better formula, and it evolves into the platform.”
Keith Rabois May 3, 2024 ▶ 34:14 Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148 · 20VC with Harry Stebbings
May 3, 2024 negative
Disclosure
Rabois: Not raising my valuation offer for Rippling was my biggest mistake
“You know, we talked about the biggest mistake ever was not raising the valuation on rippling.”
Keith Rabois May 3, 2024 ▶ 27:38 Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148 · 20VC with Harry Stebbings
May 3, 2024
Insight
Rabois: PR rarely creates lasting startup momentum without sparking real traction
“I've seen examples where people start with PR. Doesn't usually work, but once in a while, you can get a spark, and then if you see the spark, then you can figure out how to do it more scalably.”
Keith Rabois May 3, 2024 ▶ 26:37 Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148 · 20VC with Harry Stebbings
May 3, 2024 negative
Insight
Rabois: Startups with under 50% internal executive promotions are irresponsible
“Usually you're dealing with a ratio of, you know, 70% internal promotions, and 30%, you're selectively adding new capabilities, so you're always playing around with some ratio. I don't think a hundred percent works, but I also think if you're below fifty-fifty…”
Keith Rabois May 3, 2024 ▶ 19:13 Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148 · 20VC with Harry Stebbings
May 3, 2024 bullish
Opinion
Rabois: Ramp is the best-run private company on the planet
“I think we just finished a board meeting where it's pretty clear that this is the best run private company on the planet.”
Keith Rabois May 3, 2024 ▶ 7:29 Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148 · 20VC with Harry Stebbings
May 3, 2024 neutral
Assertion Not checkable as stated
Rabois: Khosla and Botha warned me 11 direct reports was excessive
“I used to get yelled at. I went pretty flat at square when I was running hot at like 11 and like Vinod and Roloff gave me feedback that that was too much.”
Keith Rabois May 3, 2024 ▶ 41:15 Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148 · 20VC with Harry Stebbings
May 3, 2024
Insight
Rabois: Executives must plan six months ahead to adjust operational levers
“Six months is about where you want someone thinking ahead because not every lever can be tuned in a week. Most can't. Not every lever can be even tuned in a month. So if you think six months ahead though, if you're really consistently six months ahead, most le…”
Keith Rabois May 3, 2024 ▶ 19:57 Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148 · 20VC with Harry Stebbings
May 3, 2024 positive
Opinion
Glyman: Rabois's 'How to Operate' lecture enabled Ramp to scale rapidly
“Change my ability to operate and helped, you know, ramp reach the scale that we're doing quickly is, is this talk he gave a decade ago called how to operate. It's on YouTube. It's free. It is worth a lot more than that. And I recommend everyone watch it.”
Eric Glyman May 3, 2024 ▶ 8:32 Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148 · 20VC with Harry Stebbings
May 3, 2024
Disclosure
Rabois: Most of my successful investment decisions took under three minutes
“On, on almost all the really good investments I've touched, I kind of knew in the 1:03 minutes.”
Keith Rabois May 3, 2024 ▶ 27:10 Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148 · 20VC with Harry Stebbings
Jun 28, 2024 neutral
What-if
Vasavada: Keith Rabois Would Not Have Responded to Cold Outreach
“I don't think Keith would have responded to a cold message. Maybe he would have, but that was really helpful, having them on board.”
Samir Vasavada Jun 28, 2024 ▶ 6:16 Samir Vasavada: The Real Story of Vise: The Regrets, Mistakes and Mis-Hires | E1171 · 20VC with Harry Stebbings
Jul 22, 2024 negative
Disclosure
Hartz dismissed and missed an early investment opportunity in YouTube
“I think of when I was stepping down as CEO of Zoom, Keith and Roloff held a lunch for me in the city, in San Francisco. What was the name of that place? And Keith was talking about this YouTube thing. I was just kind of Burnout of like, you know, it was like a…”
Kevin Hartz Jul 22, 2024 ▶ 34:42 Kevin Hartz: "How I Lost Airbnb at Seed Because of an Exploding Term Sheet" | E1180 · 20VC with Harry Stebbings
Jul 22, 2024
Disclosure
Hartz: Paul Graham rejected his exploding term sheet for Airbnb's seed round
“Little known secret is Keith, Javed and I gave an exploding term sheet to Airbnb, and Paul Graham said no bueno, and teed off on us.”
Kevin Hartz Jul 22, 2024 ▶ 37:25 Kevin Hartz: "How I Lost Airbnb at Seed Because of an Exploding Term Sheet" | E1180 · 20VC with Harry Stebbings
Aug 14, 2024 positive
Opinion
Nejatian: Keith Rabois and Max Levchin are exceptionally aggressive in execution
“And I think it may come out of how they grew in tech, is that they are, I see this with admiration, more aggressive than anyone you can imagine being. They're incredibly kind, but very aggressive, ah, in their execution, in their ambition.”
Kaz Nejatian Aug 14, 2024 ▶ 1:24 Kaz Nejatian: How Shopify Built a $90BN Business to Last 100 Years | E1189 · 20VC with Harry Stebbings
Sep 18, 2025 positive
What-if
Nejatian: Would not have taken Opendoor CEO role without Rabois and Wu
“Wouldn't have taken a job, would not have taken a job without them. Like a strip wouldn't have done it. In fact, I said I won't do it without them.”
Kaz Nejatian Sep 18, 2025 ▶ 19:51 Opendoor CEO, Kaz Nejatian: OpenAI and Oracle, How Can Either Afford to Do This · 20VC with Harry Stebbings
Sep 12, 2026 positive
Assertion Not checkable as stated
Franceschetti: Keith Rabois and Delian Asparouhov did not realize Eight Sleep co-founders were married
“To the point where I think Delian and Keith, when they invested for the first year, they, I, I'm not sure that they were not even, they didn't even know we were married. Obviously, you disclose it when you do a round, so it has been disclosed in every round, b…”
Matteo Franceschetti Sep 12, 2026 ▶ 49:55 Labour, Engineering, Social Media, GrokBots, Cybercabs: 7 Predictions for How AI Changes the World
Sep 12, 2026 positive
Disclosure
Franceschetti: Keith Rabois pushed Eight Sleep for immediate payback from day one
“Well, in our case, we look at the immediate payback period. This is actually something where Keith was really pushy and he was correct since day one. So he wanted us to have an immediate payback period.”
Matteo Franceschetti Sep 12, 2026 ▶ 9:48 Labour, Engineering, Social Media, GrokBots, Cybercabs: 7 Predictions for How AI Changes the World
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