Keith Raboy, every mention

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every year anyone Harry Stebbings 57Max Altman 6Matthew Prince 4Glenn Solomon 3Bill Gurley 3Semil Shah 2Ooshma Garg 2Nikhil Basu Trivedi 2Mike Duboe 2Michael Eisenberg 2

Verbatim, from the transcripts: the passages where Keith Raboy comes up

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Flexport CEO: Two Questions Every Founder Needs to Ask · 20VC with Harry Stebbings Jun 20, 2026 · 4 mentions

  • ▶ 5:45 Harry Stebbings I love Keith Raboy who says that actually he likes to sense check his deals with friends, and if they don't think that his deal is stupid or crazy, he's not doing his job. 2 times in the scene
  • ▶ 28:36 Harry Stebbings Well, because you, you're essentially feeding data back to the CCP would be the fear from Keith Reborn and others, and that actually CCP-funded open source models are powering the majority of early-stage Silicon Valley companies.
  • ▶ 30:37 Harry Stebbings And when I think about China, I, sadly, these days, I think about a mutual friend of ours, Keith Reboig, given his very open concerns around China, and it goes to something you said to me before, which was, going back to kind of venture…

Jake Paul: Traditional VC is Toast & Attention is More Valuable than Cash · 20VC with Harry Stebbings Apr 18, 2026 · 1 mention

  • ▶ 12:39 Harry Stebbings Keith Raboy from CoSla and previously Founders Fund said that it's really important to know what we sell as investors, like what our product is.

20VC: Max Altman on The New Seed War: Can Anyone Compete with Sequoia and a16z | Leaving $2BN on the Table with Reddit | Lessons from Backing Rippling at $25M Post | Why Climate Tech is a Mirage and Disaster Nov 21, 2025 · 6 mentions

Plural Partner, Taavet Hinrikus: Why Founders Will Realise Multi-Stage Funds Damage Seed Rounds · 20VC with Harry Stebbings Apr 28, 2025 · 1 mention

Nabeel Hyatt, GP @ Spark Capital: To Win in AI, Investors Need to Change Their Approach | E1255 · 20VC with Harry Stebbings Feb 3, 2025 · 2 mentions

  • ▶ 22:23 Harry Stebbings Keith Raboy says on the show, and very publicly, the best founders don't need the help of a VC. 2 times in the scene

Hussein Kanji, Founder @Hoxton Ventures: Why AI Means London Can Compete with the US | E1248 · 20VC with Harry Stebbings Jan 20, 2025 · 2 mentions

  • ▶ 0:57 Harry Stebbings I remember Keith Raboy telling me in a show
  • ▶ 31:56 Harry Stebbings So, like, Keith Raboy, who's a friend and been on the show a couple of times, he always says, like, the best founders don't need your help.

Alexis Ohanian: The Full P&L Breakdown of the World's Most Valuable Women's Sports Team | E1187 · 20VC with Harry Stebbings Aug 7, 2024 · 2 mentions

Michael Eisenberg: How China Could Overtake the US in the AI Race | E1167 · 20VC with Harry Stebbings Jun 19, 2024 · 1 mention

  • ▶ 1:00:11 Harry Stebbings So Keith Raboy on the show said he's worst at sourcing, and as time, relevance, and that sourcing is his biggest challenge.

Danny Rimer: The Biggest Lessons from Missing Snap, Airbnb, Spotify and Facebook | E1166 · 20VC with Harry Stebbings Jun 17, 2024 · 2 mentions

  • ▶ 36:06 Harry Stebbings You said the word relevant there, and it made me think of a show I did with Keith Raboy, um, and we talked about sourcing, selecting, and servicing, like kind of three core pillars of venture, um, and he said his biggest weakness is… 2 times in the scene

Tom Hulme: Lessons from a 24x Angel Track Record, 275x on Robinhood & Making Billions on Uber |E1150 · 20VC with Harry Stebbings May 8, 2024 · 1 mention

  • ▶ 6:26 Harry Stebbings Or they want the one investor, Peter Fenton, or you name it, Keith Raboy, who they've worked with before, knows amazing, and the rest just give me passive.

Christian Hecker & Johan Brenner: The Biggest Fundraising Lessons Having Raised $1.3BN | E1116 · 20VC with Harry Stebbings Feb 16, 2024 · 3 mentions

20VC: Doug Leone, Bill Ackman, Bill Gurley and Orlando Bravo on "Does Price Matter"; When to Pay Up vs When to Stay Disciplined, The Biggest Lessons on Price Discipline from 8 of the World's Best Investors Feb 9, 2024 · 2 mentions

  • ▶ 9:37 Harry Stebbings It was interesting, Keith Raboy actually said on a different podcast that the only firm to have retained price discipline, the only firm, was Benchmark. 2 times in the scene

The Ultimate AI Roundtable: What Happens Now in AI, Why Google are Vulnerable | E1085 · 20VC with Harry Stebbings Nov 24, 2023 · 1 mention

  • ▶ 33:14 Harry Stebbings and oh my god, we have an amazing show coming on Monday with Keith Raboy and Mike at Traba, and so stay tuned for that, because that is a fantastic show.

Harry debates Cloudflare CEO Matthew Prince: "Should startups target niche markets?" · 20VC with Harry Stebbings Oct 24, 2023 · 2 mentions

  • ▶ 7:56 Matthew Prince And, and there's a judge at the end of it who, and I can't remember who the judge was, but Keith Raboy was on the panel. 2 times in the scene

Matthew Prince: The Two Biggest Mistakes Every Founder Makes | E1072 · 20VC with Harry Stebbings Oct 16, 2023 · 2 mentions

  • ▶ 37:09 Matthew Prince And, and there's a judge at the end of it who, and I can't remember who the judge was, but Keith Raboy was on the panel. 2 times in the scene

Nikhil Basu Trivedi: Why 99% of AI Investments Will Go Bust | E1057 · 20VC with Harry Stebbings Sep 6, 2023 · 2 mentions

  • ▶ 19:15 Nikhil Basu Trivedi Yeah, like I remember having a chat with Keith Raboy about this, where he was just like, look, I just look for sort of founder plus keynote, that's my stage. 2 times in the scene

Jason Lemkin: Every VC has a FRAUD in their portfolio; The IPO market is about to EXPLODE | E1046 · 20VC with Harry Stebbings Aug 9, 2023 · 1 mention

Mike Duboe: Top 5 Lessons Scaling Stitch Fix to IPO; Why CAC/LTV is a BS Metric | 20VC #978 · 20VC with Harry Stebbings Feb 16, 2023 · 2 mentions

  • ▶ 32:15 Mike Duboe Just, you know, I think about it, but like one, one principle I like going back to Keith Raboy gave this awesome talk like eight years ago at startup school on being a great operator. 2 times in the scene

20VC: Why Operating Experience Becomes Irrelevant Fast and Operators Often Give Bad Advice to Founders, Is Silicon Valley Really Dead? Are Gen Z the Most Entitled Employees? What Will Happen to a Generation of Pre-PMF Companies with $50M in the Bank with Nov 23, 2022 · 1 mention

Mike Chalfen: How to Build Anti-Fragile Venture Portfolios Today | 20VC #904 · 20VC with Harry Stebbings Jul 8, 2022 · 2 mentions

  • ▶ 21:13 Harry Stebbings I do want to ask, I had Keith Raboy on the show recently, and he said his acid test for whether he's still a good VC is whether at least half of his friends laugh at all of his deals. 2 times in the scene

Henri Pierre-Jacques: How I Founded Harlem Capital; Our $134M Fund | 20VC #901 · 20VC with Harry Stebbings Jun 24, 2022 · 1 mention

  • ▶ 6:09 Harry Stebbings When we think about pricing, I just had Keith Raboy on the show, and he was like, the thing I wish I knew from the start of my career in venture is that C&A, just price just really doesn't matter.

20VC: Bill Gurley and Michael Eisenberg on The First Signs of an Impending Bust, What Happens with a Market Crash, How Do Public Markets Impact Private Valuations & The Biggest Lessons from 20 Years Investing in Venture Dec 6, 2021 · 3 mentions

  • ▶ 16:52 Bill Gurley I think a good example, I'd say, is Keith Raboy with things like Open Door, his current roll-up of Amazon stores or Shopify stores. 3 times in the scene

20VC: NEA's Scott Sandell on SPACS and Why Liquidity is One of the Challenges of our Time, Why We Are At An Inflection Point For Secondaries & Why There Is Nothing To Suggest The Boom Will Not Continue Mar 11, 2021 · 1 mention

  • ▶ 1:25 Harry Stebbings And speaking of amazing products with Carter there, Founders Fund's Keith Raboy believes that the best way to run finance at any growing company is to adopt Ramp, the fastest growing corporate card in America.

20VC: Aleph's Michael Eisenberg on Why Generalists Over Specialists, Why Boutique Smaller Firms Over Multi-Stage Firms, Portfolio Construction Theory, Capital Concentration Limits and How To Think Through Reserve Allocations with Market Cycles in Mind? Feb 8, 2021 · 2 mentions

  • ▶ 22:24 Michael Eisenberg Return profile than we are, and if you need multiple on a billion and a half dollar fund, you need to own 30% of Opendoor, you need to own percent of whatever Keith's working on now, and Brian, so that's the way I think about the problem,… 2 times in the scene

20VC: Lessons From Working with Bill Gates, How To Lead Without Authority and The Difference Between Leadership and Management & How Fundraising Changes In A COVID World with Quentin Clark, Managing Director @ General Catalyst Dec 28, 2020 · 1 mention

  • ▶ 18:46 Harry Stebbings It reminds me of Keith Raboy who does a smoothie test with interns, where he gives them a diet test, get me a smoothie in 10 minutes, and then with every test he does more and more, and two weeks in they should be doing something

20VC: Zach Weinberg on Whether A Company is a Democracy, The Importance of Ownership, The Rise of Pre-Emptive Rounds, Multi-Stage Funds Entering Seed and How he Approaches Both Risk and Personal Capital Allocation Nov 6, 2020 · 8 mentions

20VC: Upfront's Mark Suster on COVID Redefining What A Great Company Looks Like and What Valuations Look Like, Why Pay-To-Play Is Back On The Table & Why We Will See The Death of Party Rounds Apr 20, 2020 · 1 mention

  • ▶ 32:47 Mark Suster But virtually every company has that, you know, Keith Raboy at Square in the early days with Jack, when Jack was working across multiple companies, but there's a million examples of great compliments to founders that really help build…

20VC: Ash Fontana on The 5 Core Characteristics That Make Data Valuable, What VCs Can Learn From Italian Craftsmen and Howard Marks & The Importance of Vertical Integration In Scaling Today Nov 18, 2019 · 1 mention

20VC: Haystack's Semil Shah on Whether Founders Are Bypassing Seed Funds in Favour Of Less Dilutive Multi-Stage Funds, How Fund Strategy Changes With Fund Scaling & Why The Hardest Challenge is Price Discipline Sep 16, 2019 · 2 mentions

  • ▶ 11:00 Semil Shah But if you're trying to win and compete against a friend like Keith Raboy at Founders Fund, or against Arifjan Mohamed, who's done three or four seeds, two of which have gone on to billion-dollar companies from Lightspeed, or Ping Li at… 2 times in the scene

20VC: Being A Wartime Leader in a Time of Peace, Why Marketing Channel Diversification Is Like The Life of A Scientist and Why Small and Mighty Beats Loud and Weak with Ooshma Garg, Founder & CEO @ Gobble Nov 9, 2018 · 20 mentions

20VC: Elad Gil's High Growth Handbook on The Commonalities of The Truly Great CEOs, How To Hire The Very Best Execs, Why Cash is A Defensible Moat Today & The Pros and Cons of M&A and IPOs Jul 17, 2018 · 2 mentions

  • ▶ 37:13 unnamed speaker You know, I touch upon this in my book in a, in a conversation with Keith Raboy from COSA. 2 times in the scene

20VC: Lessons From Slack and Opendoor on Price Sensitivity, Why The Best CEOs Are Able To Manage Momentum and Why Being A Board Member is a "Full Contact Sport" with Glenn Solomon, Managing Partner @ GGV Capital May 29, 2018 · 4 mentions

  • ▶ 21:58 Glenn Solomon I met with lots and lots of companies and entrepreneurs in and around that space and ultimately got very excited when I heard about the launching of Open Door, and I asked Keith Raboy, who gave a great interview with you on your show not… 3 times in the scene
  • ▶ 29:29 Harry Stebbings So fantastic to have Glenn on the show there, and as Glenn mentioned in the episode, you can check out the episodes also with Sam Orman and Keita Raboy.

20VC: The Core Lessons From Building a 150 Startup Angel Portfolio, Why Founders Who Angel Invest Have Such Strong Advantages and Why The Lean Startup Makes Less and Less Sense Today with Adrian Aoun, Founder & CEO @ Forward May 25, 2018 · 1 mention

  • ▶ 27:29 Adrian Aoun Now, the investors that I went with in forward, people like Founders Fund or Kosla, Keith Raboy at Kosla, who I know has been on your, uh, your show.

20VC: What Is Core To The Best Investor - Founder Relationships, The Biggest Risk For Founders In The Early Days & Why EQ Is The Most Important Trait For Managers with Jack Altman, Founder & CEO @ Lattice Nov 3, 2017 · 1 mention

  • ▶ 6:10 Jack Altman So you scour your network, you look for diamonds in the rough, as Keith Raboy has said, you let people work on creative schedules if that's sort of what you need to do to get them to help you.

20VC: YC's Daniel Gross on How YC Can Democratise AI & Reduce Incumbency Advantages, Why ML Enabled Software Will Eat The Software That Ate The World & Whether AI Will Produce Independent Companies or Be Technology within Incumbents Aug 21, 2017 · 1 mention

  • ▶ 6:28 Daniel Gross And then, 800,000 dollars in angel funding from a few folks, including many who you've interviewed on the show, like Keith Raboy.

20VC: Building Shopify From $5m To IPO, Why The Future Of Retail Is Not Online vs Offline & Why Law School Is Like Finishing School For Entrepreneurs with Harley Finkelstein, COO @ Shopify May 12, 2017 · 1 mention

  • ▶ 30:07 Harry Stebbings As always, I so appreciate all your support, and I cannot wait to bring you next Monday's episode with Keith Raboy at Coastal Adventures.
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