Jack Dorsey, every mention

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every year anyone Harry Stebbings 39Biz Stone 9Keith Rabois 5Chris Sacca 5Max Rhodes 4Avlok Kohli 4Brendan Foody 3Vinod Khosla 2Suranga Chandratilake 2Maor Shlomo 2

Verbatim, from the transcripts: the passages where Jack Dorsey comes up

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Nikesh Arora on the Frontier Model Problem: Breadth vs Depth | The Future of Token Costs · 20VC with Harry Stebbings Jun 22, 2026 · 2 mentions

SpaceX's Financials Leaked: Is it Worth $2TN | Meta Debuts Muse Spark: Are They Back in the AI Race? · 20VC with Harry Stebbings Apr 16, 2026 · 1 mention

  • ▶ 1:07:53 unnamed speaker You have, you know, the block memo and what Jack Dorsey wants to do.

Gokul Rajaram: How to Analyse for Durability and Defensibility in a World of AI · 20VC with Harry Stebbings Mar 16, 2026 · 2 mentions

  • ▶ 1:13:52 Gokul Rajaram All four of them, Larry, Mark, Jack, and Tony, and now Brian Armstrong, um, Bill and Ben at Pinterest. 2 times in the scene

Anthropic vs The Pentagon: Who Wins? | OpenAI's $110BN Mega Round | Cursor Hits $2BN in ARR · 20VC with Harry Stebbings Mar 5, 2026 · 4 mentions

The SaaS Apocalypse: Who Lives & Who Dies | Insight Partners Co-Founder, Jerry Murdock · 20VC with Harry Stebbings Feb 28, 2026 · 1 mention

  • ▶ 50:22 Jerry Murdock So I think Twitter could have been infinitely a more interesting company, but VCs got involved and created politics, and they fired Jack Dorsey early, and I don't know if that was right or wrong, but they created issues, and the company…

Base44’s Founder, Maor Shlomo on How Vibe Coding Will Kill SaaS · 20VC with Harry Stebbings Nov 24, 2025 · 2 mentions

Mercor CEO & Co-Founder, Brendan Foody: How They Grew from $1M to $500M in 17 Months · 20VC with Harry Stebbings Sep 15, 2025 · 3 mentions

  • ▶ 32:33 Brendan Foody Like I remember when I was talking with Jack Dorsey before he invested, one piece of advice he gave me was that we should stay private as long as possible. 3 times in the scene

Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings Jun 16, 2025 · 1 mention

  • ▶ 6:10 Larry Aschebrook Something that was clear there, which was, there's an opportunity to buy shares from these people who have no liquidity, and there, you should be able to make more of a return than, and also, companies wouldn't return my phone call,…

Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148 · 20VC with Harry Stebbings May 3, 2024 · 2 mentions

Keith Rabois on Rejoining Khosla Ventures | E1102 · 20VC with Harry Stebbings Jan 12, 2024 · 3 mentions

Jackie Reses: The Most Powerful Woman in Finance; Making $50BN for Yahoo on Alibaba | E996 · 20VC with Harry Stebbings Mar 31, 2023 · 5 mentions

  • ▶ 35:14 Jackie Reses Really, you know, when Jack created Square was 2009.
  • ▶ 58:28 Harry Stebbings Is it purely David and Jack, and you name the great, great people, or is it the market themselves, the intricacies of them? 2 times in the scene
  • ▶ 1:16:52 Harry Stebbings What's your biggest lesson from working with Jack for many years? 2 times in the scene

Homebrew’s Hunter Walk & Satya Patel: Why $100M is Not Enough to Execute a Seed Strategy | 20VC #972 · 20VC with Harry Stebbings Jan 31, 2023 · 1 mention

William Hockey: How I Founded Plaid; The Ultimate Cold Email Tip; Hiring Lessons | 20VC #955 · 20VC with Harry Stebbings Dec 3, 2022 · 1 mention

  • ▶ 53:55 Harry Stebbings I remember when I was 18, I cold emailed Jack Dorsey when I was in San Francisco, and he responded, and I was like, wow, this works.

Cathie Wood: Elon & Twitter; Why Facebook is a Value Stock Now; ARK's Performance | 20VC #949 · 20VC with Harry Stebbings Nov 14, 2022 · 1 mention

  • ▶ 53:02 Cathie Wood And with Square or Block Cash App, you know, Jack Dorsey is, and Elon, they've been talking.

Kevin Weil: Lessons from Leading Product at Instagram & Twitter | 20VC #934 · 20VC with Harry Stebbings Oct 7, 2022 · 1 mention

  • ▶ 54:44 Kevin Weil I have been so lucky in my career, um, you know, across folks like Kevin Systrom, Jack Dorsey, et cetera.

20VC: Faire's Max Rhodes on Three Steps To Hire the Best Candidates, Why Every Company Should Have a Strategy Doc and How To Do It & The Art of Referencing; How to Get the Most Out of Every Reference Feb 18, 2022 · 4 mentions

  • ▶ 8:31 Max Rhodes I mean, number one is just how product driven square was like Jack is a technologist through and through and a designer cares so much about building great products, like cares maniacally about building great products. 2 times in the scene
  • ▶ 10:30 Max Rhodes Spent time with Jack. 2 times in the scene

20VC: How I Lost a $125M Deal with Yahoo by Being Too Honest, The M&A Meeting with Steve Jobs That Did Not Go Well and How U2's Bono Saved The Day For One Tech Startup with Ali Partovi, CEO @ Neo Jan 21, 2022 · 1 mention

  • ▶ 34:06 Ali Partovi Elon Musk is, you know, simultaneously running multiple companies or Jack Dorsey, but not counting these superhumans, the generally I would say do one thing really well.

Chris Sacca's True Unfiltered Opinion on Facebook and Softbank | Full Interview · 20VC with Harry Stebbings Jan 20, 2022 · 3 mentions

  • ▶ 2:46 Chris Sacca Um, and that annoyed the hell out of Jack, but I, that was, that was real money for me.
  • ▶ 1:03:32 Chris Sacca Doug Leone was like, fuck no, people don't just come to me with deals, but, um, I think, I think Doug was bullshitting, uh, but you know, like Instagram came to me, but like Kevin Systrom literally said, I want three angels, you, Adam…
  • ▶ 1:15:47 unnamed speaker The, the deleterious and destructive effects of their platform being weaponized, and so, you know, I don't know the extent to which Jack is a particularly reflective philosophical individual.

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 · 1 mention

  • ▶ 36:16 Bill Gurley Another one that's very similar, and it wasn't me, it was a different partner, but I don't think I was helpful, was Jack

20VC: Chris Sacca on Coming Out of Retirement To Unf**k The Planet with Lowercarbon, How Chris Evaluates His Relationship To Money Today, Why We Have Bred a Generation of Ass**** Kids, Do VCs Provide Any Real Value and The True Unfiltered Opinion on Faceb Oct 11, 2021 · 3 mentions

  • ▶ 5:33 Chris Sacca That annoyed the hell out of Jack, but that was real money for me.
  • ▶ 57:09 Chris Sacca Kevin Systrom literally said, I want three angels, you, Adam D'Angelo, and Jack Dorsey.
  • ▶ 1:06:48 Chris Sacca And so, you know, I don't know the extent to which Jack is a particularly reflective philosophical individual.

20VC: The Roblox Memo: First Round's Chris Fralic on The 17 Year Journey to Build a $41BN Market Cap Company, Why It Is Way Harder To Increase Ownership Across Rounds Today & What Happens Post SPACMania Apr 29, 2021 · 1 mention

  • ▶ 7:42 Chris Fralic Didn't feel right at the time, and clearly was a big miss for us, but it informed us to not get hung up on price for what we think can be breakout companies, and so one example where we learned and invested at an even higher price was with…

20VC: Greylock's David Sze on His Biggest Lessons Working with Mark Zuckerberg and Reid Hoffman, The Rise of Pre-Emptive Rounds, How To Think Through Price Discipline Today and How Truly Strong Venture Partnerships Function Apr 19, 2021 · 1 mention

  • ▶ 34:27 David Sze Twitter, like, Evan, Biz, and those guys, and Jack, everyone's got their list.

20VC: Wunderlist & Pitch Founder, Christian Reber on His Personal Relationship with Risk, Money, Whether the Sale to Microsoft was a Mistake, What Great Product Designs Means Today & Why Founders Investing External Capital is a Distraction Feb 15, 2021 · 2 mentions

  • ▶ 11:05 Christian Reber Someone called me the Jack Dorsey of productivity lately, and I thought, like, that maybe makes sense.
  • ▶ 33:54 Harry Stebbings So thank you so much for joining me, and I can't wait to see, what was it, the Jack Dorsey of productivity come to life in Europe?

20VC: Twitter Co-Founder Biz Stone on The 3 Stages of Wealth, The Return To Twitter in 2017 and the Associated Missions and Challenges & Why Silicon Valley is not an "Insiders Only" Universe? Jan 8, 2021 · 9 mentions

  • ▶ 5:39 Biz Stone Jack, and so, I'm doing that with Fred now, and it's just something that I did with Ben Finkel, I mean, it's just something that I, I do sort of without trying.
  • ▶ 14:19 Biz Stone I mean, I remember distinctly in the early days when, when Jack was CEO of Twitter the first time, I finally just got frustrated and said, I was upset that the site was down yet again. 6 times in the scene
  • ▶ 17:38 Biz Stone And so, what I did when I came in is, is Jack
  • ▶ 31:41 Biz Stone And that's just because it was Jack, and I knew that Jack was going to build something really cool.

20VC: Why the Theory of Pro-Rata is Often False, How Rolling Funds Impact Both Pricing and Competition & The Biggest Lessons from Working with Jack Dorsey with Avlok Kohli, CEO @ AngelList Venture Dec 21, 2020 · 14 mentions

  • ▶ 5:52 Avlok Kohli Businesses did an amazing job at emphasizing that again and again and again, and you also see it in the way that Jack talks about the customers of Square, so that really left an impression on me. 2 times in the scene
  • ▶ 7:59 Harry Stebbings So when we talk about Jack Dorsey, how can I not ask one question before we move into the rolling funds element, which I'm super excited for, but like, uh, Gokko asked this one. 10 times in the scene
  • ▶ 32:53 Avlok Kohli Definitely Jack Dorsey. 2 times in the scene

20VC: CRV's George Zachary on His Relationship To Money and How it has Changed Over Time, Why The Best Founders Have Often Experienced Parental or Home Instability and The Stories Behind Investing in Unicorns; PillPack, Yammer and Udacity Oct 12, 2020 · 1 mention

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: Vinod Khosla on What Venture Assistance Really Means, Why Many VCs Are Not Qualified To Advise Founders & Why Startups Can Innovate So Much Faster Than Incumbents Feb 24, 2020 · 2 mentions

  • ▶ 24:24 Vinod Khosla It's the kind of founder we like, like Pat Brown at Impossible Foods, or Jack Dorsey at Square, or Patrick Collison and John Collison at Stripe. 2 times in the scene

20VC: Khosla Ventures Founding Partner, Samir Kaul on Why Pro Rata Is A Cop Out, Why He Likes Technical Risk and Does Not Take Market Risk & How To Approach Time Allocation Across The Portfolio In Venture Jan 13, 2020 · 1 mention

20VC: First Round's Josh Kopelman on Why Price Is Both An Art and A Science, Why Ownership Must Be Built on First Check and The Negative Consequences of Attribution in Venture Jan 28, 2019 · 2 mentions

20VC: ClassPass CEO Fritz Lanman on Betting His Career Facebook Would Be A $10Bn Company, Lessons From Travis and Uber on Scaling A Global Marketplace & Whether Growth and Capital Efficiency Are Mutually Exclusive Jul 20, 2018 · 1 mention

  • ▶ 17:56 Fritz Lanman And we had really interesting conversations about that, but ultimately I didn't know much about the space and I met Jack and decided how many chances in your career do you get to bet on somebody like that?

20VC: How Great VCs Handle Themselves In An M&A Process, Why M&A Has Become The Primary Method of Exit & How The Best M&A Teams Operationalise Their Process with James Loftus, Corporate Development Lead @ Square Mar 26, 2018 · 1 mention

  • ▶ 4:45 James Loftus Square came calling with an opportunity to come run their corporate development team, and when I looked at the opportunity that was in front of us at Square, just for the amount of runway we have for the really mission-driven culture,…

20VC: YC's Ali Rowghani on Leadership Lessons From Steve Jobs, Ed Catmull and Jack Dorsey & The 3 Traits All Truly Successful Leaders Share Oct 30, 2017 · 2 mentions

  • ▶ 13:54 Harry Stebbings I remember crying at the movie when I saw it, but I do have to ask, you mentioned some incredible names there, from Steve Jobs to Ed Catmull to working with Jack at Twitter, 2 times in the scene

20VC: How Both Founders & GPs Should Construct Their Pitch, Why VCs Are Eternal Optimists & What Makes The Best Post-Investment VC/Founder Relationship with Brian Ascher, Partner @ Venrock May 31, 2017 · 2 mentions

  • ▶ 12:24 Brian Ascher I remember seeing Jack Dorsey's pitch for squares series a, and he literally started with like, these are 75 things that could kill this company in the short term. 2 times in the scene

20VC: Why Great Founders Are Both Visionary & Stubborn, The Investment Mindset Shift From Angel To VC & How To React When The 'S*** Hits The Fan?' with Jesse Middleton, General Partner @ Flybridge Capital Partners Aug 31, 2016 · 1 mention

20 VC FF 026: Ryan Hoover, Founder @ ProductHunt on Relationship Building, Habit Forming and The Vision for ProductHunt Dec 11, 2015 · 5 mentions

  • ▶ 20:04 Harry Stebbings And then talking of Twitter there, you are a CEO now yourself, you know of the demands and the strains, um, what do you think of Jack Dorsey being CEO of two publicly traded companies soon to be? 5 times in the scene

20 VC 090: Balderton Capital's General Partner, Suranga Chandratillake on What It Takes To Be A Great CEO Nov 23, 2015 · 12 mentions

  • ▶ 6:30 Suranga Chandratilake Um, Jack Dorsey, for example, who, you know, you know, product and technology people who've stayed in charge of their companies and, and being the CEO.
  • ▶ 6:55 Harry Stebbings It's very interesting that you mentioned Jack Dorsey, and I, you know, I'm sure you'll, you'll say yourself that being a CEO is completely overwhelming and full-time job completely, and any work-life balance is very difficult. 10 times in the scene
  • ▶ 9:44 Suranga Chandratilake That sort of, the judgment call of knowing when to be in charge and when to be, um, Jack Dorsey calls it the editor, you know, and not really being in charge, but instead just sort of letting other people flourish, um, is a, is a really…
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