Jason Calacanis, every mention

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every year anyone Harry Stebbings 57Kevin Hartz 8Ben Nader 4Brian Wong 3Ryan Hoover 2Katie Stanton 2Ed Sim 2Richard Hanson 1Peter Rojas 1Jason Lemkin 1

Verbatim, from the transcripts: the passages where Jason Calacanis comes up

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Zuckerberg Back on X Challenging Codex & Claude Code | SK Hynix’s $26BN IPO · 20VC with Harry Stebbings Jul 16, 2026 · 6 mentions

  • ▶ 41:27 Harry Stebbings Me and Jason were messaging earlier this week about Jason Calacanis' syndicate or investing activity where he basically said, hey, due to popular demand, I'm moving where we'll be investing from very early to later stage growth… 6 times in the scene

Anthropic Files to Go Public | Cognition Raises $1BN at $26BN Valuation | The 996 Work Ethic · 20VC with Harry Stebbings Jun 4, 2026 · 14 mentions

  • ▶ 1:25 Harry Stebbings The question that I'm going to start on, Jason, is one that you just highlighted brilliantly, I think, which is Anthropic files to go public. 4 times in the scene
  • ▶ 16:01 unnamed speaker And I meant to go back and look at the statement and Jason is better at me at looking things in real time.
  • ▶ 30:23 Harry Stebbings Jason, I thought your statement here was, was a good one.
  • ▶ 39:52 unnamed speaker I don't know if it would be interesting to see Jason as part of managing that spend. 2 times in the scene
  • ▶ 1:00:00 unnamed speaker And it's exactly what you said, Jason.
  • ▶ 1:04:02 unnamed speaker And a second comment is maybe Jason's right, have a go, knock yourself out. 3 times in the scene
  • ▶ 1:27:00 unnamed speaker I also like what Jason said is that you're right. 2 times in the scene

20Growth: The $6.6B Growth Engine Behind ElevenLabs | Why ElevenLabs Do Not Have PMs | The 7 Part Launch Playbook to Crush All Launches with Luke Harries, Head of Growth @ ElevenLabs Jan 11, 2026 · 1 mention

Will Cursor Kill Figma? Lightspeed Raises $9B & OpenAI’s $1B from Disney & #1 App in App Store · 20VC with Harry Stebbings Dec 18, 2025 · 10 mentions

  • ▶ 0:52 Harry Stebbings Uh, Jason, you look very smart today. 3 times in the scene
  • ▶ 25:19 unnamed speaker The question is, you're right, so I suppose to take your point, Jason, if you think the capex cycle has two more years of strong legs, then you could see these guys rebound, and if you think we may have found an equilibrium, but they're… 2 times in the scene
  • ▶ 58:55 unnamed speaker And my guess is, this is Jason, Captain Albies.
  • ▶ 1:11:00 unnamed speaker You're exactly right, Jason. 3 times in the scene
  • ▶ 1:18:29 Harry Stebbings Yeah, Jason, you just need to argue.

Why VC Today is Worse than 2021 · 20VC with Harry Stebbings Oct 23, 2025 · 14 mentions

  • ▶ 6:12 unnamed speaker Sorry, Jason, go there on that one.
  • ▶ 10:25 unnamed speaker So I agree with you on the TAM, Jason. 2 times in the scene
  • ▶ 46:51 Harry Stebbings And for those that don't know, Rory, how would you, or Jason, how would you describe it?
  • ▶ 57:42 unnamed speaker It'll just because, oh my God, to Jason's point, we over extrapolated on one year's adoption and we thought everyone's going to buy this in three years and we're going to need
  • ▶ 1:12:05 Harry Stebbings Do you agree with that Jason?
  • ▶ 1:20:41 Harry Stebbings And I'm, I am making it up, but Jason, you gave me the inspiration for this. 4 times in the scene
  • ▶ 1:25:53 unnamed speaker And the reason is something Jason mentioned earlier. 4 times in the scene

Databricks at $100BN, CoreWeave’s $11B Debt Bet & Nubank’s $2.5B Profit Shocker - Ep.19 · 20VC with Harry Stebbings Aug 21, 2025 · 1 mention

20VC: ElevenLabs Head of Growth on Why You Do Not Need PMs | The 7-Part Launch Playbook That Gets 700K+ Views Per Product | The Truth About CAC, Payback & Performance Marketing in AI with Luke Harries May 23, 2025 · 1 mention

Kevin Hartz: "How I Lost Airbnb at Seed Because of an Exploding Term Sheet" | E1180 · 20VC with Harry Stebbings Jul 22, 2024 · 8 mentions

  • ▶ 21:57 Kevin Hartz Jason Calcanis loves to talk about his investment in Uber. 8 times in the scene

Beezer Clarkson: Are LPs Open for Business & Why Do LP Incentive Mechanisms Need to Change? | E1073 · 20VC with Harry Stebbings Oct 18, 2023 · 5 mentions

Christian Lanng: "How Being a Founder Almost Killed Me" | E1065 · 20VC with Harry Stebbings Sep 27, 2023 · 2 mentions

  • ▶ 15:53 Harry Stebbings I remember Jason Calacanis told me with podcasting, he said, it's very simple. 2 times in the scene

Tim Urban: How "Wait But Why" Grew to 600k Readers; AI's Revolutionary Impact on Media | E1048 · 20VC with Harry Stebbings Aug 14, 2023 · 1 mention

  • ▶ 1:00:50 Harry Stebbings I was running the other day listening to you on This Week in Startups with Jason, uh, who we both like very much.

Brad Gerstner: How I Pick Companies; Lessons from Warren Buffet; Chamath vs Gurley | E935 · 20VC with Harry Stebbings Oct 10, 2022 · 1 mention

  • ▶ 32:43 Harry Stebbings I think it was Chamath on the panel that you and Gurley and Jake Allen and Sachs did together who said, you would never be investing in this period of uncertainty with valuations being so transient and fluid because it's almost…

Logan Bartlett: WTF is Happening at Growth Stage Investing? | 20VC #920 · 20VC with Harry Stebbings Aug 30, 2022 · 1 mention

  • ▶ 6:05 Harry Stebbings As a pre-seed investor in B-Real, I now feel like Jason Calacanis with Uber in this moment.

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

  • ▶ 42:38 Henri Pierre-Jacques So I'm not, I'm not a big reader, um, I'm a big podcast listener, and right now I'm definitely obsessed with, uh, with All In, with Chamath and Jason, and I listen to it every Saturday.

20VC: Calm Founder Alex Tew on What It Takes To Build Viral Products Today, The Current State of Customer Acquisition Costs, What Makes The Best Brands Sep 11, 2020 · 2 mentions

  • ▶ 0:29 Harry Stebbings TPG, and then some very cool names, including Ashton Kutcher, Harry Styles, Brad Feld, and Jason Calicanis.
  • ▶ 3:19 Harry Stebbings I've heard so many great things, both from Jason Calacanis, Michael Acton-Smith, and Alexander Will.

20VC: Ashton Kutcher on Early Lessons From Investing in Airbnb and Spotify, Why VC Ownership Requirements Are Becoming More and More Egregious & What Being Good At Product Truly Means Feb 17, 2020 · 1 mention

  • ▶ 6:25 Ashton Kutcher I went up to TechCrunch.com and I started meeting folks and met Jason Calacanis and Kevin Rose and Mark Cuban and the list goes on and on and on of folks she introduced me to or set up a meeting with and started just learning and being the…

20VC: Moxxie Ventures' Katie Stanton on What It Takes To Raise A First Time Fund As A Solo GP, The Entrance of Multi-Stage Funds Into Seed Rounds and The Inverse Relationship of Those That Fund Diverse Managers and Those That Say They Do Jan 27, 2020 · 2 mentions

  • ▶ 32:46 Katie Stanton And then very begrudgingly, I thought Jason Calacanis' book on angel investing was really good for new investors, and I do recommend the audio version because he's very entertaining. 2 times in the scene

20VC: The Mindset The Best Investors Assume When Assessing Opportunities, Why So Many Hardware Startups Fail Today & The Right Way To Think About Employee Retention with Andrew Farah, Founder & CEO @ Density Sep 7, 2018 · 2 mentions

  • ▶ 0:26 Harry Stebbings The startup that measures real-time occupancy of every room in your office, and to date, they've raised over sixteen million dollars in funding from some great friends of the show in the form of Founders Fund, Mark Suster at Upfront,…
  • ▶ 12:59 Andrew Farah But I heard something a long time ago on a podcast by Jason Calacanis, who's one of our investors and is on our board.

20VC: Lessons From 2x $Bn Exits in Trulia and lastminute.com, 3 Leading Indicators That Suggest Potential Marketplace Success & Why We Are Going To See A Fundamental Change To The World of VC with Pete Flint, Managing Partner @ NFX Jul 9, 2018 · 4 mentions

  • ▶ 5:39 Harry Stebbings You mentioned on your time with Last Minute when you were on Twist with Jason, you mentioned that there were things you did right and things you did very wrong with Last Minute.
  • ▶ 14:40 Harry Stebbings I'm really intrigued because in your episode with Jason, you stated your role to discover network effect businesses before they take flight.
  • ▶ 17:07 Harry Stebbings Now, there was one element from your interview with Jason on this week in startups that I, that I struggled with, and it was the element that kind of network effect businesses are the cheapest to build.
  • ▶ 19:31 Harry Stebbings Oh, you're setting me up too well here, Pete, with that capital efficiency focus, because with Jason, you said about being at Trulia, and during that time, you had a culture of frugality, but were aggressive on market share, and listening,…

20VC: Thumbtack's Marco Zappacosta on The 3 Core Elements To All Board Meetings, Raising $250m from Sequoia and Why You Have To Win Supply Side Acquisition First For Marketplace Success Apr 20, 2018 · 4 mentions

  • ▶ 0:34 Harry Stebbings To date, Thumbtack has raised over two hundred and seventy million dollars in funding from some of the very best in the industry, including Sequoia Capital, Capital G, Google's Growth Arm, Ali and Hattie Partovi, Scott and Siam Bannister,…
  • ▶ 23:43 Harry Stebbings I think I have to ask this is not in the schedule, but what's it like having Jason Calacanis as an angel? 3 times in the scene

20VC: Why Not Every Element of A Scalable Business Has To Scale, Why You Should Be Bearish on Retail & Why Fewer Businesses Are Getting Started Today Since The Great Depression with Brad Hargreaves, Founder & CEO @ Common Aug 11, 2017 · 1 mention

  • ▶ 28:53 Harry Stebbings As always, we so appreciate all your support, and I cannot wait to bring you Monday's episode with Jason Calacanis.

20VC: The 7 Requirements For Startup Scaling, Why VCs Must Approach Every Conversation with A Yes Mentality & Why We Will See The Humanisation of Technology with Renata Quintini, Partner @ Lux Capital Aug 9, 2017 · 1 mention

  • ▶ 31:15 Harry Stebbings As always, I so appreciate all your support, and I cannot wait to bring you Friday's episode with Jason Calacanis.

20VC: Investing Lessons From Fred Wilson & Brad Feld and Why Fundraising Is An Art & Not Everyone Can Be An Artist with Howard Lindzon Founder @ Stocktwits & Managing Partner @ Social Leverage Oct 17, 2016 · 1 mention

  • ▶ 2:57 Harry Stebbings As many of my listeners know, I'm a bit of a stalker when it comes to research on the guests, and I know that you were a hedge fund before, hedge fund manager before, and being a stalker, I am, I heard you in an interview three years ago…

20VC: 500 Startups' Dave McClure on Whether Unicorns Are Necessary For Venture Returns & Why Ownership Is Not The Math To Think About When Investing Aug 15, 2016 · 1 mention

  • ▶ 24:59 Dave McClure And some people like Jason Calacanis do their writing in kind of newsletter formats as well.

20VC: Why Every Employee Should Re-Apply For Their Job Every Year & The Strategies To Prepare For A Successful Fundraise with Kyle Hill, Founder & CEO @ HomeHero Jul 15, 2016 · 2 mentions

  • ▶ 0:37 Harry Stebbings Due to this immense success, Carl's been featured on CNN, Forbes, Wall Street Journal, and many more incredible publications, and Home Hero has raised funds from some of the world's best investors, including Chamath and Mamoon at Social…
  • ▶ 13:33 Harry Stebbings Uh, and you also have Mike, as we said, from science and Jason from launch or previous guests actually.

20VC: Creating A Competitive Process Between VCs & Having Bill Gurley As A Board Member with Aaron Hirschhorn, Founder & CEO @ DogVacay May 13, 2016 · 1 mention

  • ▶ 23:13 Aaron Hirschhorn Jason, uh, Jason's got a great, uh, ticker that he sends out daily from, from inside, which I think has a lot of like snippets and sound bites of, of interesting news.

20VC: Sprig's Gagan Biyani on The 3 Principles Of Fundraising and Building The World's Largest Restaurant Apr 8, 2016 · 1 mention

  • ▶ 7:16 Harry Stebbings And obviously I'm a huge fan of, uh, Jason Calacanis, ex guest of the shows this week in startups.

20 VC: Niccolo De Masi @ Glu Mobile on Private Market Valuations, Being A Public Market CEO & The Trends Of Mobile Gaming Feb 19, 2016 · 1 mention

  • ▶ 1:50 Harry Stebbings I'm such a huge fan of yours, having listened to your interview with Cara and Jason, and, and being a big fan of Glue, so

20VC FF 028: Where To Start Your Startup and Single Founder vs Co-Founder Model with Richard Hanson, Co-Founder & CEO @ HiringScreen Jan 1, 2016 · 1 mention

  • ▶ 22:15 Richard Hanson I do have a soft spot for Jason, and, um, I would say Brad Feld and Feld Thoughts is, um, is also very good.

20 VC FF 026: Ryan Hoover, Founder @ ProductHunt on Relationship Building, Habit Forming and The Vision for ProductHunt Dec 11, 2015 · 2 mentions

  • ▶ 12:31 Ryan Hoover The three that I listen to, um, a lot of mine are really focused on startups and that kind of thing, so I'm actually excited to explore non-startup, non-technology podcasts, but a few that I love are This Week in Startups with Jason… 2 times in the scene

20 VC 092: The Repeatable Playbook of SaaS with Ed Sim, Founding Partner @ BoldStart Ventures Nov 30, 2015 · 2 mentions

  • ▶ 21:51 Ed Sim I love Jason Kalkanis' launch ticker. 2 times in the scene

20 VC FF 018: Brian Wong, Founder @ Kiip on Raising $30m in VC Funding by 24 Oct 23, 2015 · 3 mentions

  • ▶ 24:06 Brian Wong You know, funnily enough, this is just top of mind, is I found some of Cal Canis' hugely long rambling email newsletters pretty interesting. 3 times in the scene

20 VC 079: BETAWORKS WEEK: East vs West Coast Investing with Peter Rojas, EIR @ Betaworks, Co-Founder @ Weblogs & Engadget Oct 14, 2015 · 2 mentions

  • ▶ 0:30 Harry Stebbings Prior to joining Betaworks, he was VP of strategy at AOL, and he was also the co-founder of several startups, including WebBlogs, Inc., with previous guest Jason Calacanis, which was acquired by AOL in 2005.
  • ▶ 5:33 Peter Rojas And so I left and helped start Weblogs Inc. with Jason Calcanis and Brian Alvey.

20 VC 071: Pre-Seed Investing, Why Now Is The Best Time with Nicholas Chirls @ Notation Capital Sep 14, 2015 · 1 mention

FF 011: 'The Savviest Investors Don't Ask What If' with Ben Nader, CEO & Founder @ Butterfleye Sep 4, 2015 · 7 mentions

  • ▶ 0:28 Harry Stebbings Including our dear friends and past guests, Brad Feld and Jason Calacanis, who I would like to say a special thank you to for introducing us to Ben.
  • ▶ 15:20 Harry Stebbings And you've also raised funding from our dear friend and previous guest, Jason Kalkanis.
  • ▶ 22:20 Ben Nader Jason's stuff. 4 times in the scene
  • ▶ 25:17 Harry Stebbings As always, all the items and resources mentioned in today's show, including Jason's link to LaunchTicker and BradFeldsFeld.com, can be found on the blog at www.TheTwentyMinuteVC.com.

James Altucher: Ideas, Investing and Entrepreneurs Jun 4, 2015 · 1 mention

  • ▶ 0:03 Harry Stebbings On Monday's episode, we had the legendary Jason Calacanis, and I'm so thrilled to welcome James Altichip to the show today.
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