Keith Rabois

Keith Rabois was an early executive at PayPal (part of the famous PayPal Mafia), COO at Square, VP of Corporate Development at LinkedIn, and an early investor in Stripe, DoorDash, Airbnb, YouTube, Ramp, and Palantir. Currently he’s managing director at Khosla Ventures. Also, he hasn’t touched a computer since September 2010 (he does everything from an iPad). In our in-depth conversation, Keith shares: 1. The barrels vs. ammunition hiring framework (and how to spot barrels) 2. Why talking to customers is actively harmful for consumer products 3. How to identify undiscovered talent 4. Why the PM role is dying 5. The three traits of the best-performing companies right now 6. The specific interview question he asks every senior candidate 7. Why CMOs (not engineers) are becoming the #1 consumer of tokens — Brought to you by: WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs Vanta—automate compliance, manage risk, and accelerate trust with AI — Episode transcript: https://www.lennysnewsletter.com/p/hard-truths-about-building-in-the-ai-era — Archive of all Lenny's Podcast transcripts: https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 — Where to find Keith Rabois: • X: https://x.com/rabois • LinkedIn: linkedin.com/in/keith • Website: https://www.khoslaventures.com — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — In this episode, we cover: (00:00) Introduction to Keith Rabois (01:59) Why Keith hasn’t used a computer since 2010 (04:52) The team you build is the company you build (07:40) How Keith learned to identify talent at PayPal (10:05) Tactics for getting better at hiring (15:31) The barrels vs. ammunition framework (18:52) What makes someone a barrel (22:36) How to attract the best talent (26:18) Building companies on undiscovered talent (27:53) Why better performance requires more pressure (32:36) Career advice in the age of AI (35:14) The future of the product triad (41:03) Why design and code are merging (49:35) What practicing law taught Keith about entrepreneurship (51:22) Contrarian takes on customer feedback (1:02:33) Identifying great AI opportunities (1:05:13) Advice for evaluating statrups  (1:12:36) Criticizing in public vs. private (1:15:05) Failure corner (1:17:29) Lightning round — Referenced: • Square: https://squareup.com • Jack Dorsey on X: https://x.com/jack • Head of Claude Code: What happens after coding is solved | Boris Cherny: https://www.lennysnewsletter.com/p/head-of-claude-code-what-happens • Simon Willison’s Weblog: https://simonwillison.net • Vinod Khosla on X: https://x.com/vkhosla • Peter Thiel on X: https://x.com/peterthiel • Max Levchin on X: https://x.com/mlevchin • David Sacks on LinkedIn: https://www.linkedin.com/in/davidoliversacks • Tony Xu on X: https://x.com/t_xu • David Sze on X: https://x.com/davidsze • Faire: https://www.faire.com • Max Rhodes on X: https://x.com/MaxRhodesOK • Jeffrey Kolovson on LinkedIn: https://www.linkedin.com/in/jeffreykolovson • Uncapped | Comparative Advantages w/ Keith Rabois: https://www.khoslaventures.com/posts/uncapped-comparative-advantages-w-keith-rabois • Lattice: https://lattice.com • Taylor Francis on LinkedIn: https://www.linkedin.com/in/taylor-francis-4ba49640 • Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead): https://www.lennysnewsletter.com/p/building-product-at-stripe-jeff-weinstein • The art of hiring: insights from Khosla Ventures, Airbnb, Ramp and Traba: https://ramp.com/velocity/the-art-of-hiring-insights • Eric Glyman: Seek out super individual contributors (ICs): https://ramp.com/velocity/the-art-of-hiring-insights#Eric-Glyman:-Seek-out-super-individual-contributors-(ICs) • Eric Glyman on X: https://x.com/eglyman • Mike Moore on LinkedIn: https://www.linkedin.com/in/mike-moore-802223177 • Brian Chesky’s new playbook: https://www.lennysnewsletter.com/p/brian-cheskys-contrarian-approach • Why you should work much harder RIGHT NOW: https://marginalrevolution.com/marginalrevolution/2026/03/why-you-should-work-much-harder-right-now.html • Opendoor: https://www.opendoor.com • The Craft of Early Stage Venture | Peter Fenton, General Partner at Benchmark | Uncapped with Jack Altman: https://www.youtube.com/watch?v=vRiblwiXt-Q • Lovable: https://lovable.dev • The rise of the professional vibe coder (a new AI-era job) | Lazar Jovanovic (Professional Vibe Coder): https://www.lennysnewsletter.com/p/getting-paid-to-vibe-code • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • Marc Andreessen: The real AI boom hasn’t even started yet: https://www.lennysnewsletter.com/p/marc-andreessen-the-real-ai-boom • Jeremy Stoppelman on X: https://x.com/jeremys • The design process is dead. Here’s what’s replacing it. | Jenny Wen (head of design at Claude): https://www.lennysnewsletter.com/p/the-design-process-is-dead • Andy Warhol: https://en.wikipedia.org/wiki/Andy_Warhol • Curation and Algorithms: https://stratechery.com/2015/curation-and-algorithms • Ernest Hemingway: https://en.wikipedia.org/wiki/Ernest_Hemingway • William Shakespeare: https://en.wikipedia.org/wiki/William_Shakespeare • Evan Moore on X: https://x.com/evancharles • Andrew Mason on X: https://x.com/andrewmason • Read Taylor Swift’s Full Viral Speech After Record-Breaking Awards Sweep: https://www.newsweek.com/entertainment/read-taylor-swift-full-acceptance-speech-record-breaking-awards-sweep-11745941 • The Chainsmokers: Stories Behind the Songs, AI’s Impact on Music, and Venture Investing | Uncapped with Jack Altman: https://www.youtube.com/watch?v=9GMSC-2pYnw&list=PLtpH7YnTL8ihy0nR2BV32n5VkRtqlDAS1&index=16 • How to spot a top 1% startup early: https://www.lennysnewsletter.com/p/how-to-spot-a-top-1-startup-early • David Weiden on LinkedIn: https://www.linkedin.com/in/davidweiden • Alfred Lin on LinkedIn: https://www.linkedin.com/in/linalfred • Keith’s post about vertical integration on X: https://x.com/rabois/status/870673635375104000 • Jon Chu on X: https://x.com/jonchu • Kanu Gulati on X: https://x.com/KanuGulati • Rogo: https://rogo.ai • Profound: https://www.tryprofound.com • Basis: https://www.getbasis.ai • Spellbook: https://www.spellbook.legal • Roelof Botha on X: https://x.com/roelofbotha • Delian Asparouhov on LinkedIn: https://www.linkedin.com/in/delian-asparouhov-87447742 • Lessons From Keith Rabois, Essay 1: How to become a Venture Capitalist: https://delian.io/lessons-1 • Velocity over everything: How Ramp became the fastest-growing SaaS startup of all time | Geoff Charles (VP of Product): https://www.lennysnewsletter.com/p/velocity-over-everything-how-ramp • Nuremberg on AppleTV+: https://tv.apple.com/us/movie/nuremberg/umc.cmc.3sg4y0382byupy76bfy7307k4 • Eight Sleep: https://www.eightsleep.com • “NO DAYS OFF”—Bill Belichick on X: https://x.com/SNFonNBC/status/829036279069364224 — Recommended books: • Creativity, Inc.: Overcoming the Unseen Forces That Stand in the Way of True Inspiration: https://www.amazon.com/Creativity-Inc-Overcoming-Unseen-Inspiration/dp/0812993012 • The Jordan Rules: The Inside Story of One Turbulent Season with Michael Jordan and the Chicago Bulls: https://www.amazon.com/Jordan-Rules-Sam-Smith/dp/0671796666 • The Upside of Stress: Why Stress Is Good for You, and How to Get Good at It: https://www.amazon.com/Upside-Stress-Why-Good-You/dp/1101982934 — Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. — Lenny may be an investor in the companies discussed. To hear more, visit www.lennysnewsletter.com

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

From politics to technology to real estate, Keith Rabois has bold predictions for America’s next decade. In this conversation with Erik Torenberg, Keith breaks down why he believes the U.S. is entering a new economic expansion driven by AI, productivity, and sovereign technology. They discuss how AI could lift GDP growth to 5%, why sovereign AI projects are inevitable, and why America can “grow its way out” of debt. Keith also shares his takes on Trump’s second term, the decline of legacy institutions, OpenAI’s dominance, the future of Google and Microsoft, and how startups like Ramp and Opendoor are rewriting the rules of fintech and housing.   Resources: Follow Keith on X: https://x.com/rabois Follow Alex on X: https://x.com/arampell   Stay Updated:  If you enjoyed this episode, be sure to like, subscribe, and share with your friends! Find a16z on X: https://x.com/a16z Find a16z on LinkedIn: https://www.linkedin.com/company/a16z Listen to the a16z Podcast on Spotify: https://open.spotify.com/show/5bC65RDvs3oxnLyqqvkUYX Listen to the a16z Podcast on Apple Podcasts: https://podcasts.apple.com/us/podcast/a16z-podcast/id842818711 Follow our host: https://x.com/eriktorenberg Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures.   Stay Updated: Find a16z on YouTube: YouTube Find a16z on X Find a16z on LinkedIn Listen to the a16z Show on Spotify Listen to the a16z Show on Apple Podcasts Follow our host: https://twitter.com/eriktorenberg Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

(0:00) The Besties welcome Travis Kalanick and Keith Rabois! (3:02) Travis on Pony.ai / Uber rumors and the state of Cloud Kitchens (18:51) xAI launches Grok 4, learning "The Bitter Lesson" in AI (40:36) How Grok can catch ChatGPT in usage, OpenAI's product excellence (46:27) Perplexity and OpenAI building AI-native browsers and taking on Chrome (58:01) Elon's "America Party": is now the right time for a third party, and could he make an impact in 2026? (1:13:12) SCOTUS backs Trump over federal government RIF plans Follow Keith: https://x.com/rabois Follow Travis: https://x.com/travisk Get The Besties All-In Tequila: https://tequila.allin.com Join us at the All-In Summit: https://allin.com/summit Summit scholarship application: http://bit.ly/4kyZqFJ Follow the besties: https://x.com/chamath https://x.com/Jason https://x.com/DavidSacks https://x.com/friedberg Follow on X: https://x.com/theallinpod Follow on Instagram: https://www.instagram.com/theallinpod Follow on TikTok: https://www.tiktok.com/@theallinpod Follow on LinkedIn: https://www.linkedin.com/company/allinpod Intro Music Credit: https://rb.gy/tppkzl https://x.com/yung_spielburg Intro Video Credit: https://x.com/TheZachEffect Referenced in the show: https://www.nytimes.com/2025/06/26/technology/uber-travis-kalanick-self-driving-car-deal.html https://www.youtube.com/watch?v=ZW5fJikPmfM https://grok.com https://www.youtube.com/watch?v=_wTA90BYo30 https://techcrunch.com/2025/01/08/elon-musk-agrees-that-weve-exhausted-ai-training-data https://x.com/ArtificialAnlys/status/1943166841150644622 https://x.com/elonmusk/status/1943192643439337753 http://www.incompleteideas.net/IncIdeas/BitterLesson.html https://x.com/chamath/status/1943177837956968499 https://techcrunch.com/2025/07/09/perplexity-launches-comet-an-ai-powered-web-browser https://x.com/perplexity_ai/status/1942969263305671143 https://x.com/elonmusk/status/1941584569523732930 https://polymarket.com/event/will-elon-register-the-america-party-by https://ropercenter.cornell.edu/presidential-approval/highslows https://news.gallup.com/poll/651278/support-third-political-party-dips.aspx https://www.whitehouse.gov/presidential-actions/2025/02/implementing-the-presidents-department-of-government-efficiency-workforce-optimization-initiative https://www.scotusblog.com/2025/07/supreme-court-allows-trump-administration-to-implement-plans-to-significantly-reduce-the-federal-workforce https://www.afge.org/article/summary-of-afge-lawsuits-against-trump--how-litigation-works https://cei.org/publication/10kc-2025-numbers-of-rules https://www.netflix.com/tudum/articles/american-manhunt-osama-bin-laden-release-date-news

Travis Kalanick

CEO, CloudKitchens (co-founder, Uber)

CloudKitchens

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

Debate between Keith Rabois and Zach Weinberg on what tariffs are actually trying to accomplish. One core theme: Tariffs aren’t fully about “bringing back factories,” but rather a negotiation tool to eliminate foreign trade barriers - ultimately aiming to increase free trade, not restrict it. We also got into: - What each of them would do if they were in charge - Whether the trade deficit is a meaningful metric or just a misunderstood talking point - If tariffs could be part of an initiative to replace income tax — shifting toward a more consumption-based tax system - If tariffs could successfully be used as a non-military tool to reduce drug supply to the US - If there’s a major disconnect between the new administration’s rhetoric and the actual economic goals behind the policy One of the deepest economic conversations from the show’s recent history — and a rare debate where both sides had real logic behind their views. (00:00) Introduction and Host's Biases (00:46) Keith's Perspective on Tariffs (03:05) Zach's Perspective and Clarifying Questions (05:14) Debating Tariff Strategies (07:45) Economic Implications and Free Trade (13:31) Trump's Tariff Policies and Goals (16:57) Global Trade and Protectionism (25:52) Final Thoughts on Tariffs and Trade (29:16) Discussion on Trade Tariffs and Partners (30:17) Impact of Tariffs on GDP and Debt (31:20) Political Coalitions and Trade Policies (32:00) Tariffs as Consumer Taxes (33:30) Debate on Trade Deficit and Tariff Rates (36:53) Regulatory Reforms and Economic Policies (47:25) Fentanyl Crisis and Trade Negotiations (51:06) Closing Remarks and Future Topics Executive Producer: Rashad Assir Producer: Leah Clapper Mixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎙 Listen to the show Apple Podcasts: https://podcasts.apple.com/us/podcast/the-logan-bartlett-show/id1606770839 Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow 🐦 Twitter - https://twitter.com/loganbartshow 🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the Show Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes.

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

Zach Weinberg

Co-Founder

Operator PartnersCurie.BioFlatiron Health

(0:00) The Besties welcome Keith Rabois! (4:01) Keith explains why he returned to Khosla Ventures, the differences between Founders Fund and Khosla, and his husband Jacob Helberg's role in Trump Admin (13:09) Business acumen of Trump's cabinet and appointees, diversity of opinion (25:59) Google's new quantum chip: potential impact on encryption, cryptography, and more (43:50) Apple developing new server chip for AI inference, iOS flop, why its product culture is failing (54:30) TikTok panics after appeals court upholds the "divest-or-ban" law, with a January 19th deadline (1:03:55) State of Venture Capital, why Stripe is still private, thoughts on crypto Follow the besties: https://x.com/chamath https://x.com/Jason https://x.com/DavidSacks https://x.com/friedberg Follow Keith: https://x.com/rabois Follow on X: https://x.com/theallinpod Follow on Instagram: https://www.instagram.com/theallinpod Follow on TikTok: https://www.tiktok.com/@theallinpod Follow on LinkedIn: https://www.linkedin.com/company/allinpod Intro Music Credit: https://rb.gy/tppkzl https://x.com/yung_spielburg Intro Video Credit: https://x.com/TheZachEffect Referenced in the show: https://www.tiktok.com/@frankielapenna/video/7010077215576575238 https://www.axios.com/2024/12/06/trump-billionaires-cabinet-elon-musk https://blog.google/technology/research/google-willow-quantum-chip https://www.nature.com/articles/s41586-024-08449-y https://research.google/blog/suppressing-quantum-errors-by-scaling-a-surface-code-logical-qubit https://quantumai.google/roadmap https://en.wikipedia.org/wiki/Hartmut_Neven https://en.wikipedia.org/wiki/Double-slit_experiment https://www.discovery.com/science/Double-Slit-Experiment https://en.wikipedia.org/wiki/Schr%C3%B6dinger%27s_cat https://www.theinformation.com/articles/apple-is-working-on-ai-chip-with-broadcom?rc=pxkrxo https://x.com/rabois/status/870673635375104000 https://www.amazon.com/Company-Giants-Conversations-Visionaries-Digital/dp/0070329656 https://www.cnn.com/2024/12/09/tech/bytedance-tiktok-halt-us-ban-intl/index.html https://apnews.com/article/tiktok-us-ban-sale-china-congress-de12b4d22aa8095e62cb0982a6e62235 https://apnews.com/article/tiktok-ban-congress-bill-1c48466df82f3684bd6eb21e61ebcb8d https://pitchbook.com/news/reports/q3-2024-pitchbook-nvca-venture-monitor https://www.cnbc.com/2024/12/12/servicetitan-starts-trading-on-nasdaq-after-ipo.html https://www.nytimes.com/2024/12/11/business/dealbook/ftc-trump-ferguson-khan.html https://www.ben-evans.com/benedictevans/2021/6/15/antitrust https://www.bloomberg.com/news/articles/2024-12-05/convertible-bond-arbs-are-making-microstrategy-wall-street-s-hottest-trade

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

Eric Glyman is the Co-Founder and CEO of Ramp, America's fastest growing corporate card and finance automation platform. Under Eric's leadership, Ramp has raised more than $1 billion in financing, with a valuation of $8.1 billion. Prior to Ramp, Eric co-founded Paribus, a price-tracking app to help consumers save money (acquired by Capital One). Ramp recently raised another $150 million series D round co-led by Founders Fund and Khosla ventures, with a post-money valuation of $7.65 billion. Keith Rabois is a Managing Director @ Khosla Ventures and one of the most respected venture investors of the last decade. Keith has led investments in Stripe, Faire, Ramp, Affirm and many more. Prior to Khosla Ventures, Keith was General Partner at Founders Fund, where he led investments for Ramp, Trade Republic, and Aven. In Today's Episode with Eric Glyman and Keith Rabois We Discuss: Behind Ramp's Partnership with Founders Fund & Khosla Ventures How did the first Founders Fund deal come to be? How was the first meeting? What does Keith mean when he says Ramp has the "secret sauce" to be successful? What are 1-2 things Keith thinks Eric is world-class at? What are 1-2 things Eric thinks Keith is world-class at? How did the latest Khosla deal come to happen? Ramp: The Fastest Executing Company on the Planet. How is Eric so good at executing at Ramp? What is his biggest advice to founders on speed of execution? What are Eric's biggest challenges in the next 12 months at Ramp? Why does Keith believe momentum is crucial for early stage startups? What are some easy ways founders can build momentum? How does Eric think AI will accelerate Ramp and the world of finance? Leadership Lessons From the Best Founders What are Keith's biggest lessons from Brian Chesky @ Airbnb? What did Keith learn from Jack Dorsey @ Square about leadership? What does Eric think founders today should build? What should they not build? What did Eric learn from Keith on how founders should measure time & progress? Hiring & Team Management How did Ramp build a solid talent team? What did they do differently? Does Keith & Eric believe it is better to hire externally or promote internally? What is the right balance? Does Keith agree founders should hire & get out the way or micromanage? How many direct reports does Keith think is enough?

Eric Glyman

Co-founder and CEO

RampParibus

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

Keith Rabois is a Managing Director @ Khosla Ventures and one of the most respected venture investors of the last decade. Keith has led investments in Stripe, Faire, Ramp, Affirm and many more. Just last week, Keith announced he would be rejoining Khosla from Founders Fund, where he spent an immensely successful 5 years as a General Partner. Prior to Founders Fund, Keith started his career at Khosla where he spent 6 years and led investments in DoorDash, Opendoor, Webflow and more. In Today's Episode with Keith Rabois We Discuss: 1. The Decision to Rejoin Khosla Ventures: Why did Keith decide to rejoin Khosla Ventures from Founders Fund? What did Keith miss most that Khosla did, that Founders Fund did not? How did Delian take the news? 2. Comparing Two Great Firms: Founders Fund vs Khosla Ventures: Investing Style: How does Keith compare the investing styles when analyzing FF and KV? Price Discipline: Which firm is more price-disciplined? Does price discipline even matter? What are the single biggest mistakes Keith has made on price? How did it change how he invests? Founder Type: What sort of founder would choose KV? What founder would choose FF? How did the depth & quality of investment decision-making compare between KV and FF? 3. What It Takes To Win in Venture in 2024: Liquidity: What have been Keith's biggest lessons on when is the right time to sell positions? Capital Planning: What have been Keith's biggest lessons on the most effective use of reserves? Why does Keith believe if you do not lose some deals as an investor, you are not competing for the right companies? Khosla Ventures recently raised $3BN. How important is the ability to support companies across their lifetime in 2024 vs stage specific? 4. Where is The Best Place to Invest: Why does Keith think seed is the best place to be investing today? Why despite the better risk/reward profile, does Keith think Series A is not the best place to invest? Does Keith believe we will see the return of growth investing in 2024? What does Keith predict for the M&A market in 2024? Did Figma kill all activity? When will the IPO windows open again? Why would Stripe go out this year? 5. Keith Rabois: AMA: Why did Keith not want to start his own fund? Will he ever? What have been Keith's biggest lessons from working with Vinod Khosla and Peter Thiel? What were Keith's biggest lessons from Roelof Botha on what it takes to be an effective board member? How does Keith think about bitcoin in 2024?

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

Keith Rabois is a General Partner @ Founders Fund, one of the world's best venture funds with a portfolio including the likes of Facebook, SpaceX, Anduril, Tesla and many more. For the last 23 years straight, Keith has either invested in or founded a $BN company. Keith is also the Co-Founder and CEO @ Openstore, the company that will buy or run your Shopify business. Mike Shebat is the Founder and CEO @ Traba, the company providing industrial staffing when and where you need it. To date, Mike has raised $49M with Traba from some of the best including Founders Fund, General Catalyst and Khosla Ventures. In Today's Episode We Discuss: 1. What it Takes to Build a Great: Why does Mike expect everyone to work in office 12 hours per day, 4 days per week? At what point does an extra hour of work not lead to more output? What are the expectations in terms of emails, out of office, the weekends? Keith, from the 23 BN companies you have worked with, is this insane work ethic aligned to all of them? Which had it? What did not? What core components of PayPal's work ethic made it so strong? What does Keith mean when he says Linkedin could and should have been 5x bigger? 2. The Hiring Process for the Swat Team: What does the hiring process look like for this type of work environment? What are the signs that someone is really aligned to it vs faking it for the interview process? What have been Keith's biggest lessons on both compensation and title in the hiring process? Why does Keith believe that culture is like concrete? What are the biggest mistakes he has made on culture and what would he have done differently? 3. First-Time Founders, Innate Entrepreneurs & Europe's Failing: Does Keith agree the best founders always show signs of early entrepreneurship in their teens? Why does Keith prefer first-time founders to serial entrepreneurs? Why are they better? Why does Keith believe that Europe has not created a $100BN company since 1990? 4. Remote Work, Network Effects and Baseball: Why does Keith believe being great in venture is like baseball? Why does Keith and Founders Fund not invest in remote teams? How does he explain Gitlab? Why does Keith believe Airbnb has the best network effect he has ever seen?

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

Mike Shebat

Founder & CEO

Traba

Keith is the Co-founder and CEO of OpenStore, a portfolio of brands building its own shopping destination. Before starting OpenStore, Keith was an early executive at companies like PayPal, eBay, LinkedIn, and Square, a co-founder of OpenDoor, and an early investor in companies like DoorDash, Faire, Affirm, Webflow, Ramp, and Stripe, and is also currently a General Partner at Founders Fund Keith started the company in 2021 with co-founders Jack Abraham, Matt Lanter, and Jeremy Wood, and has since raised over $150 million supported by investors like Atomic, Founders Fund, General Catalyst, Khosla Ventures, Lux Capital, and Vine Ventures. — Brought to you by Packsmith, better fulfillment for growing brands. Sign-up here https://bit.ly/PacksmithBanana — In this episode, we discuss: • The 3-minute conversation that started OpenStore • All the problems that still exist in ecommerce • Why Instagram Shopping failed • What Keith and team are building at OpenStore • Why Wish failed • The margin profile of most consumer brands • A crash course on contribution margin and profitability for startup founders • How OpenStore gets 3x higher contribution margin than other consumer brands • As a VC, the one thing Keith looks for in the founders he backs • A framework for founders and investors to consider when incubating companies • Why Keith thinks no great SF-based startups has been founded since March of 2020 • The reasons he moved to Miami • Why he’s bearish on most AI startups • His favorite interview questions for candidates Referenced: • Email Keith - keith@foundersfund.com Where to find Keith: • Twitter: https://twitter.com/rabois • LinkedIn: https://www.linkedin.com/in/keith Where to find Turner: • Newsletter: https://www.thespl.it • Twitter: https://twitter.com/TurnerNovak Production and distribution by: https://www.supermix.io Want to sponsor the show? https://docs.google.com/forms/d/e/1FAIpQLSebvhBlDDfHJyQdQWs8RwpFxWg-UbG0H-VFey05QSHvLxkZPQ/viewform

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

Keith Rabois is a prominent Silicon Valley investor and entrepreneur. He is currently the CEO and founder of OpenStore, and a partner at Founders Fund, a venture capital firm co-founded by Peter Thiel. Prior to this, he served as the COO at Square, a mobile payments company founded by Jack Dorsey, and was also part of the so-called "PayPal Mafia," a group of individuals who co-founded PayPal or worked there in its early days and went on to become successful entrepreneurs and investors. Throughout his career, he has been involved in the founding and growth of many successful technology companies, including Yelp, LinkedIn, and YouTube. In Keith's second appearance on the podcast, he discusses topics such as his dislike for OKRs, his aversion to investing in remote-first companies, and his experiences working with Peter Thiel, Reid Hoffman, and Jack Dorsey. (0:00) Intro (1:14) Welcome back, Keith (5:35) Hating OKRs (10:03) On making decisions (14:09) Not believing in remote work (17:33) Social Issues in the Workplace (19:00) What is the role of a VC? (22:08) Thinking about what can go right (29:35) The "why you" in a potential investment (34:28) Fitting the founder to the story (37:59) The most successful founders are trending older (43:21) The firm brand at Founders Fund (47:57) Lessons learned from Keith's only five bosses in his career (55:48) Thoughts on AI (59:36) Artificial Intelligence in China (1:03:23) What is your most contrarian view today? (1:06:56) On Elon & using Twitter   Show Notes: https://twitter.com/rabois https://www.youtube.com/watch?v=6fQHLK1aIBs https://delian.io/lessons-3   Mixed and edited: Justin Hrabovsky Produced: Rashad Assir Executive Producer: Josh Machiz Music: Griff Lawson   🎙 Listen to the show Apple Podcasts: https://podcasts.apple.com/us/podcast/three-cartoon-avatars/id1606770839 Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1 Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg   🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1   Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow 🐦 Twitter - https://twitter.com/loganbartshow 🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow   About the Show Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes. Executive Producer: Rashad Assir Producer: Leah Clapper Mixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow 📱 X - https://twitter.com/loganbartshow 🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the Show Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member. Tap follow and enable notifications to stay ahead of the game.

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

Multiple time guest and friend of the pod Keith Rabois is back! Jason and Keith talk 2023 macro outlook (1:00), big tech's impact on startups (10:01), advice for founders (18:24), Meta's risky VR bet (27:22), ChatGPT vs Google (39:05), and more! (0:00) Jason intros today's guest: Keith Rabois! (1:00) Keith's 2023 macro outlook and thoughts on startup valuations (8:54) Vanta - Get $1000 off your SOC 2 at https://vanta.com/twist (10:01) What are big tech hiring freezes and RIFs doing to the startup market? Entitlement era coming to an end (18:24) Advice for different archetypes of founders (25:50) Acquire.com - Sign up for FREE at https://try.acquire.com/twist (27:22) Importance of founder authority, Tim Cook taking over for Steve Jobs at Apple, Meta's risky VR bet (37:34) Apply for the LAUNCH Accelerator: https://launchaccelerator.co (39:05) Keith's thoughts on ChatGPT, a new approach to search, and Microsoft taking on Google (53:37) What types of founders is Keith looking to invest in right now? (59:25) OpenDoor thoughts + a little politics FOLLOW Keith: https://twitter.com/rabois FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

Bill Gurley is a General Partner @ Benchmark Capital, Bill, is widely recognized as one of the greats of our time having worked with the likes of GrubHub, NextDoor, Uber, OpenTable, Stitch Fix, and Zillow. Doug Leone is the Global Managing Partner @ Sequoia Capital, one of the world's most renowned and successful venture firms with a portfolio including the likes of Google, Airbnb, Whatsapp, Stripe, Zoom and many more. Keith Rabois is a General Partner @ Founders Fund, one of the best performing funds of the last decade with a portfolio including Facebook, Airbnb, SpaceX, Stripe, Anduril, the list goes on. Arthur Patterson and Jim Swartz founded Accel in 1983. Under their leadership, they have built Accel into one of the most prominent venture firms of the last 4 decades. Michael Eisenberg is a Co-Founder and Equal Partner @ Aleph, with a portfolio including the likes of Lemonade, Melio and HoneyBook, they are one of the leading early-stage firms of the last decade. Sonali De Rycker is a Partner @ Accel, one of the leading firms of the last 3 decades with a portfolio that includes the likes of UiPath, Miro, Spotify and many more incredible companies. Fabrice Grinda is the Founding Partner @ FJ Labs, with over 700 investments, Fabrice has had over 250 exits and built a portfolio including Alibaba, Coupang, Airbnb, Instacart, Flexport, and many more. In Today's Episode You Will Learn: 1.) How does the current environment compare to prior busts? 2.) How will the changing interest rates impact the startup funding climate moving forward? 3.) Why is the rate of inflation the only true metric which reveals the ultimate fate of the economy? 4.) What are the world's leading investors telling their founders? 5.) How are the best investors in the world thinking through reserves management?

Bill Gurley

General Partner, Benchmark

BenchmarkBenchmark Capital

Doug Leone

Global Managing Partner

Sequoia Capital

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

Keith Rabois is a General Partner @ Founders Fund, one of the best performing funds of the last decade with a portfolio including Facebook, Airbnb, SpaceX, Stripe, Anduril, the list goes on. As for Keith, he has led the first institutional investments in DoorDash, Affirm and co-founded Opendoor. He has also led investments in Faire, Ramp, Trade Republic, and Stripe. As an operator, Keith has an unparalleled track record as a Senior Exec at Paypal, he then went on to influential roles at Linkedin and being COO at Square. Finally, as an angel, Keith made early investments into Airbnb, Lyft, Palantir, Wish and more. In Today's Episode with Keith Rabois: 1.) Buy Low, Sell High: What BS! Why does Keith believe that "buy low, sell high" does not work in venture? Why would it lead you to very dangerous investment decisions at the early stage? How does the size of your fund impact the appropriateness of "buy low, sell high"? 2.) The Current Landscape: Does Keith believe the current state of public markets is an over-reaction or a new normal? How does Keith respond to the suggestion that Founders Fund has paused new investments given the uncertainty in the market? How does Keith think about investing through cycles and temporal diversification? How does Keith advise young investors today questioning whether they are actually any good at this? What does Keith believe are his biggest fears and insecurities today? 3.) Outcome Scenario Planning and Competitor Analysis: Does Keith believe outcome scenario planning is important? Why does Keith believe you can always tell your biggest hits early? What have been the core signs for him? What have been some of Keith's biggest lessons from Mike Moritz and Vinod Khosla when it comes to upside maximization? What are the right questions to ask? Why does Keith believe you do need to look through public market comps when investing in startups? 4.) Time Allocation and Losing Faith in Founders: How does Keith approach time allocation across the portfolio? Spend time with the winners or help the struggling companies? What have been his biggest lessons here? What does Keith do when he has lost faith in the founder? How does he communicate it to them? What does Kieth believe VCs do wrong when they no longer believe in the founder or company? 5.) Do VCs Add Value? What does Keith believe is the acid test for whether he is doing his job as a VC properly? Why does Keith believe there are only 5 board members that add true value to their companies at scale? Who is the best board member Keith has ever worked with? Why? Why does Keith believe that age is not your friend as an investor? How does he combat this? 6.) The Downfall of SF and Wokeness: Will we see a reduction of wokeness in companies with the public markets correcting and power shifting from employees to employers? Is Keith concerned by the lack of coherence in the US today when it comes to politics? What are the core reasons for the downfall of SF to Keith? Why does he believe it is a net negative to build a company in SF today? Items Mentioned in Today's Episode: Keith's Most Recent Investment: Found

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

This talk was recorded LIVE at the All-In Summit in Miami and included slides. To watch on YouTube, check out our All-In Summit playlist: https://bit.ly/aisytplaylist 0:00 Tim Urban gives a talk on political discourse in America and explains high-rung vs. low-rung thinking 26:20 The Besties and Keith Rabois join Tim Urban on stage for a roundtable discussion on cancel culture 51:23 Keith Rabois talks about taking a pause on new investments in 2022 and gives his take on other major VC players Follow the guests: https://twitter.com/waitbutwhy https://twitter.com/rabois Follow the besties: https://twitter.com/chamath https://linktr.ee/calacanis https://twitter.com/DavidSacks https://twitter.com/friedberg Follow the pod: https://twitter.com/theallinpod https://linktr.ee/allinpodcast Intro Music Credit: https://rb.gy/tppkzl https://twitter.com/yung_spielburg Intro Video Credit: https://twitter.com/TheZachEffect

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

(04:35) Miami Tech Week is just dangerous being so close to Coachella (08:18) Netflix somehow losing subscribers even though they raised prices and have 98 competitors (24:14) Elon Musk just buying stuff out of spite (29:57) A16Z’s new Accelerator (36:08) Keith Rabois interview and his hottest of takes   Follow the show: https://twitter.com/cartoonavatars https://www.instagram.com/cartoonavatars/ https://www.tiktok.com/@cartoonavatars   Follow the hosts: https://twitter.com/zck https://twitter.com/nikitabier https://twitter.com/loganbartlett   Mixed and edited: Justin Hrabovsky Produced: Andrew Nadeau and Rashad Assir Executive Producer: Josh Machiz Music: Griff Lawson   Reference Links: Netflix stock loss: https://www.cnbc.com/2022/04/19/netflix-nflx-earnings-q1-2022.html Elon Musk twitter funding: https://www.theverge.com/2022/4/21/23033445/elon-musk-twitter-bank-debt-commitment-letter A16Z Accelerator program: https://techcrunch.com/2022/04/18/andreessen-horowitz-a16z-start-seed/ Executive Producer: Rashad Assir Producer: Leah Clapper Mixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow 📱 X - https://twitter.com/loganbartshow 🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the Show Logan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member. Tap follow and enable notifications to stay ahead of the game.

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

World-class investor-operator Keith Rabois is back for his eighth time! But first, Jason breaks down Airbnb’s great Q4 and full-year earnings report (2:42) and how its customer segment is evolving. Then, he briefly covers the SF Board of Education recall (22:58). When Keith joins (31:27), he and Jason discuss: 1. How he called the top of the tech market in November 2021 2. Keith's 2019 prediction that came true 2. Venture Capital's decaying price discipline 3. Facebook's challenge ahead 4. Six predictions for the market Notes 0:00 Jason intros today’s topics: $ABNB full year earnings, SF BOE recall, and a Keith Rabois interview 2:42 Jason breaks down Airbnb’s full year results 11:57 Vanta - Get get $1,000 off automating your SOC 2 at https://vanta.com/twist 13:14 Jason reflects on Airbnb’s roadmap based on clues from their earnings report 21:42 Gun.io - Get $250 off your first developer hire at https://Gun.io/twist! 22:58 SF Board of Education recall, tech people getting involved in government 29:56 Eight Sleep - Go to https://eightsleep.com/twist to check out the Pod Pro Cover and get $150 off at checkout! 31:27 Keith Rabois joins and talks with Jason about calling the top of the tech market in November 43:27 Reflecting on the absence of pricing discipline in VC and how the FED is running out of tools to combat inflation 53:34 Breaking down Facebook’s precarious situation 1:05:16 6 Market predictions Check out Founders Fund: https://www.foundersfund.com FOLLOW Keith: https://twitter.com/rabois FOLLOW Jason: https://linktr.ee/calacanis FOLLOW Molly: https://twitter.com/mollywood

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

Keith Rabois is a General Partner @ Founders Fund, one of the most successful venture firms of the last decade with home runs in the likes of SpaceX, Palantir, Stripe, Anduril, Facebook, Airbnb, Nubank and many more. As for Keith, he led the first institutional investments in DoorDash, Affirm and has also led investments in Ramp, Trade Republic, Faire and Stripe. Prior to venture, Keith had the most stellar operating career, joining PayPal when their monthly burn-rate was $6 million; Keith joined LinkedIn, Slide and Square when they had no revenue. Fun fact, five companies Keith helped build are now publicly traded with market caps >$1 Billion. Three others have been acquired for greater than $1 Billion or are publicly traded IPOs. If that was not enough, Keith is also the Co-Founder and CEO @ OpenStore, acquiring small DTC businesses. In Today's Episode with Keith Rabois You Will Learn: 1.) How Keith first came up with the idea for Opendoor? How a conversation with Peter Thiel led to the founding of the first iteration of the company? Why did it take Keith close to a decade to pursue the idea fully, post having the idea in 2003? 2.) The Market: What made Keith so excited to pursue Opendoor from a top-down market analysis perspective? What does Keith look for in markets he likes to invest in? How did Keith expect the market to change and evolve? What did the market do differently to how Keith thought it would behave? 3.) The Business Model: With debt being the oxygen for Opendoor, how many homes did they need to acquire before they could prove they could price homes accurately? What were Keith's lessons from the first homes they bought? What did not go to plan? Why does Keith disagree, if macro hits real estate, Opendoor's model is challenged? Why does Keith believe it is stronger then? 4.) The Team: What does Keith look for in the founding teams he backs? How does Keith detect diamonds in the rough? How can teams systematically de-risk an opportunity with their experience? With the benefit of hindsight, what would Keith have done differently with the team? 5.) The Funding: Was fundraising for Opendoor always easy? How did the seed round go down? How does Keith feel today about pre-emptive rounds where little company development has taken place? Why did Opendoor decide to SPAC? Why not a direct list? Was this the right choice? What makes for the best SPAC partner?

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

Check out Founders Fund: https://foundersfund.com FOLLOW Keith: https://twitter.com/rabois FOLLOW Jason: https://linktr.ee/calacanis

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

FOLLOW Keith: https://twitter.com/rabois FOLLOW Jason: https://linktr.ee/calacanis

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

Follow Keith: https://twitter.com/rabois Follow Jason: https://linktr.ee/calacanis Thanks to our partners... Gusto - 3 months free at https://gusto.com/twist Dell for Entrepreneurs - Save up to 48% at https://dell.com/twist LinkedIn Jobs - Get $50 off your first job post at https://www.linkedin.com/twist

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

Keith Rabois (Paypal, Linkedin, Square) and SaaStr Founder Jason Lemkin talk about the landscape of SaaS & Cloud fundraising and valuation in 2020. This episode is an excerpt from Keith and Jason's session at SaaStr Summit: The New New in Venture. Full video: https://youtu.be/KxTZfx_QpjY Podcast transcript: https://www.saastr.com/saastr-podcasts-for-the-week-with-keith-rabois-and-jason-lemkin/

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

0:56 Jason intros Keith Rabois and checks in on his quarantine, Zoom's heightened exhaustion factor & more 5:46 What will the lasting impact of COVID be on Silicon Valley & the startup funding landscape? 8:18 How the early 2000's dot-com bust paved way for a generation of new founders & why the PayPal mafia of outsiders thrived in chaos & became the establishment 14:23 What has happened to intellectual debate during COVID-19? What are first principle thinkers and why are they important to problem-solving? 20:53 Is domain expertise overrated? 22:39 Keith's on his pinned tweet about his perceived recipe for startup success 26:50 In which verticals did Keith find outliers using his low-NPS/fragmented/vertical solution strategy? 32:15 History on US relationship with China, has Trump been right on China threat, should US try and bring manufacturing back from China? 44:41 China's involvement with whistleblowers, benefits of litigation knowledge as a VC, world's reaction to China mishandling COVID info 50:40 Has Biden been soft on China? How will that play into the 2020 election? 1:00:51 Why is the stock market bouncing back so quickly with record-setting unemployment numbers? Will there be another correction? 1:03:59 What is Keith seeing across his portfolio? M&A opportunity for companies like Lyft? 1:09:34 Keith shares thoughts on the right time to go public 1:13:50 Impact of 20% unemployment on startups over the next year, mental impact of lockdown & social isolation 1:20:40 Keith's most positive outlook going forward

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

Khosla Ventures partner Keith Rabois talks with Recode's Kara Swisher about the current startup and venture capital landscape, the Trump administration and more. In this episode: (01:18) Rabois's background; (04:28) Becoming a venture capitalist and how Khosla Ventures invests; (09:37) The startup and venture capital landscape; (15:06) Why startup fundraising was unusually hectic in December; (19:15) Investing in healthcare, aerospace and autonomous driving; (26:56) Artificial intelligence; (29:02) Ethical issues in advertising and at Facebook; (36:40) Political advertising and Russian media manipulation; (40:40) The prospect of regulation; (46:32) Saudi Arabia and the murder of Jamal Khashoggi; (50:04) Contrarianism and book recommendations; (53:45) Being conservative and Rabois' friend Peter Thiel; (58:07) What happens to the Trump administration next?; (1:02:16) Who could run against Trump and win?; (1:04:47) Rabois's real estate company Opendoor Learn more about your ad choices. Visit podcastchoices.com/adchoices

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

My guest this week is Keith Rabois. Keith is currently an investment partner at Khosla Ventures, but has a storied and diverse background as an investor, entrepreneur, and executive. He has worked in senior positions at Paypal, LinkedIn, and Square; has led investments in companies like Stripe, YouTube, Palantir, and AirBnB; and started the company OpenDoor, which aims to transform the process of selling a home through technology. One fun fact about Keith is that he may have the most impressive list of bosses I’ve ever seen, which we discuss during the episode. We cover a lot, but one thing we kept returning to was business strategy. Keith’s frameworks for gaining and building strategic power helped me clarify my thinking on the topic, and his examples of contrarian thinking will hopefully make you question some commonly held beliefs. Please enjoy our conversation.   For more episodes go to InvestorFieldGuide.com/podcast. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Show Notes 1:35  (First Question) – A look at his investing philosophy 3:16  – Favorite examples of his own investment history             4:40 – 7 Powers: The Foundations of Business Strategy 5:07 – Understanding what is anomalous in a given investment 7:07 – How much a secret needs to be protected within a business 11:51 – Why accumulating advantage with data is of interest to Keith 15:12 – Digital health companies and ideas that he finds compelling 16:17 – Nuance around financial services that investors should be mindful of 17:56 – How do they evaluate managers ability to recruit talent 19:36 – How similar are the roles of entrepreneur, board member, investor, etc that Keith has had in his career 24:02 – Ways that Keith is a contrarian, including his feelings on “lean startup.” 27:04 – Is problem identification a specific skill set 28:29 – Objection with experimentation/iteration 30:02 – Bad ideas in venture 31:36 – What he likes about Apple             31:51 – Creative Selection: Inside Apple's Design Process During the Golden Age of Steve Jobs 32:26 - Interview questions for identifying great talent 35:41 – Elements of good design 37:14 – Impact of platforms on opening new opportunities 38:42 – His take on valuation in the early stage environment 40:33 – Advice he would give people early in their careers 43:58 – Do high growth companies get beat by established larger businesses 45:25 – Popular narratives that he thinks are just wrong 48:22 – His thoughts on how people should learn, balancing experience vs information gathering 50:00 – Other investors that are taking a unique approach to investing 51:57 – Reflecting on the entrepreneur as a client model of private equity 55:04 – Books that he recommends that is least known             55:18 – The Upside of Stress: Why Stress Is Good for You, and How to Get Good at It 56:30 – Kindest thing anyone has done for Keith   Learn More For more episodes go to InvestorFieldGuide.com/podcast.  Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

Keith Rabois is an investment partner at Khosla Ventures where he has led investments in Stripe, Thoughtspot, HealthTap and Teespring among many others. He also started OpenDoor, which aims to transform the process of selling a home through technology. Keith's unparalleled operational track record does not stop there as he has forged several of the most important new social and commerce platforms over the last decade holding key roles at LinkedIn, Paypal and being COO at Square. As a board member, Keith guided Yelp [NYSE: YELP] and Xoom [NASDAQ: XOOM] from inception to successful IPOs. Simultaneously, he also invested in other like-minded entrepreneurs with early stakes in YouTube [acquired by GOOG], Yammer [acquired by MSFT], Palantir, Lyft, AirBnB, Eventbrite and Quora. In Today's Episode You Will Learn: 1.) How Keith made the move from key executive at LinkedIn, Paypal and Square to being a VC with Khosla? 2.) Question from Lee Hower: What were the biggest learnings from playing a key role at LinkedIn, Paypal and Square? How do they compare to learning from Slide, a not so successful project? Does one learn more from success or failure? 3.) Question from Jason Lemkin: How can founders assess the potential of their teams? How long is it possible to allow individuals to stretch to their roles? What are the signs that people are either exceeding or falling below expectations? 4.) Eric Yuan @ Zoom has previously illustrated the importance to me of sustainable growth. What is Keith's view of this? Why does he not like this term? What are his thoughts on the key constraints on growth for most startups? Items Mentioned In Today's Show: Keith's Fave Book: The Upside of Stress Keith's Fave Blog: Stratechery Keith's Most Recent Investment: Forward As always you can follow Harry, The Twenty Minute VC and Keith on Twitter here! Likewise, you can follow Harry on Snapchat here for mojito madness and all things 20VC. Eight is a sleep innovation company. With their latest product, the Eight Smart Mattress, being a bed that literally tells you how well you slept last night, paired with an intelligent sensor cover that measures the quality of your sleep and delivers a daily sleep report. In order to bring you the best product, Eight used anonymized sleep data and feedback from over 10,000 people, to understand which materials and types of mattresses give customers the best sleep resulting in their unique blend of four responsive and high-density foam layers plus one layer of proprietary technology that helps people track and improve their sleep. You can check it out on Eightsleep.com – and if you use the code 20VC you will get a whopping 20% discount! FullContact provides the ability to organize your contacts, gain rich insights into them and therefore build deep relationships. With features like automatically identifying and merging duplicate contacts to the ability to snap a photo of a business card and FullContact will transcribe them for you, so no more lost and loose business cards at events. It is with these features just being the tip of the iceberg, FullContact really is the best all in one solution for contact management and you can check them out on fullcontact.com.

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

Khosla Ventures investment partner Keith Rabois talks with Kara Swisher about building PayPal before the dot-com crash and the entrepreneurial lessons he applied from that company to later jobs at LinkedIn, Slide, Google and Square. Now, as a venture capitalist, he sees himself as a consulting psychologist for many companies in his portfolio. He also discusses why investors who once feared missing the next Uber are now rejecting startups with high burn rates. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

This episode was recorded at Saastr Annual 2016 and it is an incredible conversation whereby Jason Lemkin deep dives into the career and wisdom of Keith Rabois. For those that do not know, Keith is a legend of the tech industry having helped build some of the most important companies in Silicon Valley including Paypal, Square and Linkedin. He is also a very prominent VC with Khosla Ventures and has recently rejoined the world of operations, looking to disrupt the world of property with OpenDoor. For your chance to win a signed copy of Jason's new book 'How Hyper Growth Companies Create Predictable Revenue', we would be so grateful for you to upvote the episode on ProductHunt! In Today's Show We Cover: Why Keith rejoined the world of operations having been a VC with Khosla? Is domain expertise a good or a bad thing to have when entering an industry? When hiring, how do you achieve the balance of experience and potential? When is the right time to hire a COO? What are the signs? How Did Keith approach hiring in high growth rocketship companies? If you would like to find out more about the show and the guests presented you can follow us on Twitter here: Jason Lemkin Harry Stebbings Saastr Keith Rabois If you enjoyed the conversation with Keith today and want to save your space at what promises to be the best Saastr Annual ever, Saastr Annual 2017! You can buy early bird tickets here!

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore

Keith has been an early executive at startups such as Linkedin, Paypal, Square, and has been an early investor in companies such as Youtube, Airbnb, Palantir, Quora, Yelp, and much more. In this episode we discuss Keith’s story, his thoughts on career strategy, his philosophy on hiring and why its similar to drafting athletes, and much more. This was recorded during the LAUNCH conference earlier this year. Edited by Alex Kontis Feedback to @eriktorenberg Praise to @rabois

Keith Rabois

Managing Director, Khosla Ventures

Khosla VenturesFounders FundOpendoorOpenStore