Nov 27, 2023 · 1h 6m · news
Keith Rabois & Mike Shebat: Creating an Olympian Mindset to Work Ethic| E1087 · 20VC with Harry Stebbings
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In this energetic episode of 20VC, host Harry Stebbings sits down with investor Keith Rabois and Traba CEO Mike Shebat to discuss the uncompromising "Olympian" work ethic, aggressive in-person culture, and rigorous execution strategies required to build generational, multi-billion-dollar technology companies.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 15.4% of the talking time here. How this is scored →
Harry as informed peer 4.0 Guest teaching 4.3 Guest disagreement 2.9 Harry pushing back 4.0
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:00:02 Keith rejects remote work advocates on Twitter
Keith forcefully dismisses online critics of his in-person stance, pointing out that commenters who have never built successful companies do not understand why GitLab was a rare open-source exception.
Hardest push from Harry ▶ 59:44 Harry directly challenges Keith's anti-remote stanceHarry refuses to let Keith's blanket ban on remote startups pass without scrutiny, explicitly bringing up high-profile counterexamples like GitLab and Zapier.
Biggest teaching moment ▶ 35:18 Keith explains why LinkedIn underperformed its potentialKeith reframes LinkedIn's $24B outcome as a relative failure of execution, educating the host on how 35-hour workweek norms prevented the platform from surpassing Facebook.
Harry holds his own ▶ 55:06 Harry delivers a definitive rule on pitching investorsHarry confidently asserts a core fundraising rule that founders should never waste energy educating obtuse investors, which Keith fully endorses and expands upon.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Introductions of the Guests and Traba's Mission | 1 | 2 | 1 | 1 | Harry introduces the guests and opens up the topic by asking about Traba's culture doc and what an Olympian work ethic means. Mike lays out Traba's 12-hour work days and in-office expectations without friction. | |
| Keith Rabois on Historical Work Ethic and Unicorn Success | 1 | 4 | 2 | 0 | Keith explains that extreme effort is standard across 80%+ of top companies, illustrating how early PayPal prohibited living far from the office. Harry listens as Keith elaborates on inputs driving top outcomes. | |
| Addressing the Sustainability of High-Intensity Work Schedules | 3 | 4 | 3 | 5 | Harry challenges the non-stop intensity model by citing common feedback he receives about burnout and sustainability. Mike and Keith reframe sustainability around momentum and elite athletic training. | |
| Maintaining Peak Team Alignment and Individual Commitment | 4 | 4 | 2 | 6 | Harry uses an athletic rest-day analogy to question whether extra working hours hit diminishing returns. Mike and Keith reframe time allocation around high leverage and off-field preparation like studying film. | |
| Debating Side Projects versus Pure Professional Focus | 6 | 3 | 3 | 5 | Harry takes a firm stance against side projects, recalling a debate with Jack Altman and asserting employees should focus on core mastery. Mike strongly agrees while Keith nuances the role of broad reading. | |
| Keith Rabois on the Brutal Trade-Offs of Dual Operating Roles | 5 | 4 | 2 | 7 | Harry directly confronts Keith on his dual roles as VC partner and CEO, asking if one is effectively a side project. Keith candidly acknowledges the tension and time trade-offs of operating. | |
| The Recruiting Magnet of a High-Performance Culture | 3 | 5 | 6 | 3 | Harry brings up the European perspective on work-life balance, prompting Keith to forcefully dismiss European work ethic and note the absence of giant tech companies created in Europe since 1990. | |
| Filtering Out Complacency and Embracing Far-Right Outcomes | 2 | 3 | 2 | 2 | Harry asks about public pushback on social media regarding Traba's culture. Mike explains he explicitly filters for far-right bell-curve performers who want extreme commitment. | |
| Balancing Startup Cash, Generational Wealth Equity, and Title Red Flags | 4 | 3 | 2 | 3 | Harry probes compensation strategy, asking if Traba pays a cash premium to demand higher effort. Mike explains balancing Series A cash discipline with heavy equity upside. | |
| Can High-Velocity Startup Culture Scale Beyond Series A? | 3 | 5 | 2 | 4 | Harry asks whether high-intensity startup culture inevitably regresses to the mean as companies scale. Keith cites Apple and Amazon as exceptions while explaining how network effects protect scaling businesses. | |
| Hiring Cultural Fits and Correcting Alignment Missteps | 3 | 4 | 1 | 5 | Harry asks Keith when culture breaks and interrupts to clarify what 'fixing a person' practically means. Keith and Mike explain immediate management feedback and Andy Grove leverage frameworks. | |
| Celebrating Wins While Resisting the Traps of Complacency | 5 | 3 | 2 | 4 | Harry shares his personal management view that celebrating wins breeds complacency. Mike agrees on avoiding complacency but explains why celebrating team milestones maintains morale. | |
| Visions of Greatness and the Cautionary Tale of LinkedIn | 3 | 6 | 5 | 3 | Keith delivers a notable critique of LinkedIn, asserting it only achieved 5-20% of its potential despite a $24B acquisition due to French engineers working 35-hour weeks instead of maintaining an Olympic work ethic. | |
| Optimizing Your Twenties for Long-Term Career Velocity | 3 | 5 | 4 | 4 | Harry contrasts working late in one's twenties with traveling and seeing the world. Keith aggressively reframes relaxing in your twenties as professional suicide, citing top tech founders and Thiel Fellows. | |
| The Early Origins of Relentless Resourcefulness | 6 | 4 | 1 | 2 | Harry posits a thesis that great founders show early adolescent entrepreneurial traits. Both guests validate Harry's observation using examples like Trey Stevens and Paul Graham's essays. | |
| Debating the Merits of First-Time Founders and Cultivating Culture | 7 | 6 | 5 | 7 | Harry explicitly challenges common VC wisdom by stating he dislikes first-time founders due to avoidable mistakes. Keith counters forcefully, arguing first-time founders are better on average due to unconstrained ambition. | |
| Transitioning from Army to Navy Seal Mindset | 5 | 5 | 2 | 6 | Harry pushes Keith on how to handle underperforming portfolio founders who refuse advice. Keith explains the realistic 40% hit rate in venture capital and his approach of playing back exaggerated feedback. | |
| Filtering Investor Advice and Applying Frameworks | 3 | 4 | 1 | 3 | Harry asks Mike how he filters investor advice without over-weighting prominent board members. Keith notes that every successful business is a unique cult requiring specific decision frameworks. | |
| Challenging Mainstream Advice: Apple, Google, and Startup Philosophy | 4 | 6 | 5 | 3 | Harry asks about universal management frameworks. Keith sharply criticizes standard transparency advice, highlighting Apple's extreme secrecy and calling Google's 20% side-project time inapplicable to non-monopolies. | |
| Pitching the Right Investors vs. Mediocre Ones | 6 | 5 | 4 | 5 | Harry offers a firm VC rule: founders should never waste time educating investors who don't grasp their market. Keith agrees strongly, advising founders against practicing pitches on mediocre investors. | |
| Remote Work Exceptions and Airbnb's World-Class Network Effects | 6 | 6 | 7 | 7 | Harry directly challenges Keith's anti-remote rule by bringing up counterexamples like GitLab and Zapier. Keith pushes back aggressively, explaining he personally sourced GitLab as a rare open-source exception. | |
| Quick-Fire Round: Interest Rates, Competition, and Life Lessons | 4 | 4 | 2 | 3 | Harry executes a quickfire round covering interest rates, competition, and VC talent development. Keith outlines why Founders Fund needs younger talent to evaluate future generations of founders. |
Statements from this episode (46)
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.”
Shebat: Workers should approach joining startups like joining Olympic sports teams
“I do believe strongly that everyone should be joining a company, more like an Olympic sports team. You need that level of commitment, you need that level of being all in.”
Mike Shebat: Traba will become the AWS of labor for global supply chains
“I'm the CEO of a company called Trava, and we're a labor marketplace that connects workers with open shifts in the light industrial industry, and our mission is to empower both businesses and workers to reach their full productivity and potential. So what that…”
Shebat: Traba requires 12-hour in-office workdays Monday through Thursday
“So what it means in practice at Trava is we're all committed to at least 12 hour days, Monday through Thursday. Friday, we're working late, but people do tend to go out on, on Friday night. But it's an in-office culture”
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.”
Rabois: Only 3 of 254 early PayPal employees lived in San Francisco
“There was three people out of 254 people in the company that, when we sold the company, that could live in San Francisco because the company was based in Palo Alto. There was no extra time to commute between Palo Alto and San Francisco.”
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.”
Shebat: Late-night team presence compounds startup execution speed
“The reason why I wanted to change the mindset is because if you know that not only you, but all your colleagues are also going to be there at eight PM, you're not even thinking about pushing it out the next day. You're doing it that night. And then at scale, l…”
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 advises VCs against simultaneously acting as company founders
“So there are real, real trade-offs to company building. I would not recommend that.”
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.”
Rabois: No $100 billion European tech company has been created since 1990
“There hasn't been a hundred billion dollar European company created since 1990.”
Shebat: Candidates overly focused on job titles are an immediate red flag
“If they're way too focused on title, it's an immediate red flag.”
Shebat: Candidates prioritizing cash over equity present a yellow flag
“People that are way too focused on cash. Versus the equity. I do think that's more of a yellow flag.”
Rabois: Network effects offset the inevitable regression of employee quality at scale
“I think you definitely do past X thousand employees see some regression to the mean, and the art is constructing some accumulating advantages, let's say a network effect before that happens, because the momentum of a network effect can offset some of the slipp…”
Keith Rabois claims Amazon and Apple scaled to 10,000 workers without regressing
“Both Amazon and Apple were able to scale to Call at least 10,000 employees without regressing.”
Rabois: Almost all successful CEOs procrastinate on firing culturally misaligned employees
“Almost every other CEO I know, including ones who've been incredibly successful, probably procrastinates on that conversation a little too long.”
Shebat: Most Y Combinator startups fail because they get complacent post-graduation
“Why most Y Combinator startups that graduate Y Combinator end up not making it. And it's because they get complacent and they lose momentum.”
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, …”
Rabois: LinkedIn should have been more valuable than Facebook
“LinkedIn by any measure was Yeah, pretty successful. Certainly impact, you know, acquisition, twenty four billion or so. Truthfully, probably hit somewhere between five and 20% of its, you know, potential because it didn't do some of these things. Like, I, in …”
Rabois: LinkedIn developed a mediocre culture because early engineers wanted 35-hour weeks
“Yeah, we didn't have an Olympic work ethic. We had a bunch of French engineers that wanted to work 35 hours a week. At the time, In 2003 to five, when the company was really founded, most people thought the internet was dead, so we didn't, Reid Hoffman, who fo…”
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.”
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…”
Rabois: Tech opportunity cost in your twenties is uniquely high
“In technology, the opportunity cost in your twenties is very high. If you look at a lot of people who have been most successful, the foundations of their career are in their twenties.”
Rabois: Most of the best people I have ever worked with started as interns
“Most of the best people I've ever worked with in my career were actually interns.”
Founders Fund's Trey Stephens Got Into Georgetown After Camping Outside Admissions
“Like there's actually a general partner of founders fund named Trey. We were just at his 40th birthday party. And one thing that was mentioned was that he didn't get into Georgetown the first time. And he literally went and like set up a tent in front of the a…”
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.”
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.”
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.”
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.”
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…”
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.”
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.”
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.”
Rabois: Practices that work at Apple cannot work at Google
“Like, nothing that works at Apple would work at Google. Like, everything Google does is completely antithesis of Apple, and so that's why you have to have, like, a philosophy that accommodates successful examples, and then you apply that philosophy to what you…”
Rabois: Google's 20% time policy is catastrophic for non-monopoly startups
“If you have a monopoly, for example, Google has this 20%, you know, side project bullshit where they used to. If you have a monopoly business with 99% gross margins or 90% margins, maybe letting your employees waste time once in a while maybe isn't catastrophi…”
Rabois: Great Investors Consistently Focus on the Same Core Pitch Drivers
“There's usually two or three things that matter, and when you talk to a really good investor, it's so consistent how they dial into the same two or three things.”
Rabois: Founders Fund will not invest in remote-first startups
“We at Founders Fund have pretty much put a light in the sand that we won't invest in remote companies because we've just watched 50 years that there's almost no examples of people building companies that way.”
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…”
Rabois calls Airbnb the best network effect business he's ever seen
“They have the best network effect business I've ever seen.”
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.”
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…”
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…”
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.”