Jason Calacanis
45 statements across 8 episodes · 17 bullish · 12 bearish · 4 people on the record · first statement Jun 1, 2015 by Jason Calacanis · said 109 times in 36 episodes since 2015 · across every show →
On the record as a speaker too: Jason Calacanis's record, appearances and statements → this page counts the times other people say the name.
Mentions by year
brought up most by Harry Stebbings (57), Kevin Hartz (8), Ben Nader (4), Brian Wong (3), Ryan Hoover (2), Katie Stanton (2), Ed Sim (2), Richard Hanson (1)
tap a year for its mentions
2026 21 mentions in 3 episodes 7 per episode
- Anthropic Files to Go Public | Cognition Raises $1BN at $26BN Valuation | The 996 Work Ethic · 20VC with Harry Stebbings
- Zuckerberg Back on X Challenging Codex & Claude Code | SK Hynix’s $26BN IPO · 20VC with Harry Stebbings
- 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
- every mention in 2026, scene by scene →
2025 26 mentions in 4 episodes 7 per episode
- Why VC Today is Worse than 2021 · 20VC with Harry Stebbings
- Will Cursor Kill Figma? Lightspeed Raises $9B & OpenAI’s $1B from Disney & #1 App in App Store · 20VC with Harry Stebbings
- Databricks at $100BN, CoreWeave’s $11B Debt Bet & Nubank’s $2.5B Profit Shocker - Ep.19 · 20VC with Harry Stebbings
- 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
- every mention in 2025, scene by scene →
2024 8 mentions in 1 episode
2023 8 mentions in 3 episodes 3 per episode
- Beezer Clarkson: Are LPs Open for Business & Why Do LP Incentive Mechanisms Need to Change? | E1073 · 20VC with Harry Stebbings
- Christian Lanng: "How Being a Founder Almost Killed Me" | E1065 · 20VC with Harry Stebbings
- Tim Urban: How "Wait But Why" Grew to 600k Readers; AI's Revolutionary Impact on Media | E1048 · 20VC with Harry Stebbings
- every mention in 2023, scene by scene →
2022 3 mentions in 3 episodes 1 per episode
- Brad Gerstner: How I Pick Companies; Lessons from Warren Buffet; Chamath vs Gurley | E935 · 20VC with Harry Stebbings
- Logan Bartlett: WTF is Happening at Growth Stage Investing? | 20VC #920 · 20VC with Harry Stebbings
- Henri Pierre-Jacques: How I Founded Harlem Capital; Our $134M Fund | 20VC #901 · 20VC with Harry Stebbings
- every mention in 2022, scene by scene →
2020 5 mentions in 3 episodes 2 per episode
- 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
- 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
- 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
- every mention in 2020, scene by scene →
2018 10 mentions in 3 episodes 3 per episode
- 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
- 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
- 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
- every mention in 2018, scene by scene →
2017 2 mentions in 2 episodes 1 per episode
- 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
- 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
- every mention in 2017, scene by scene →
2016 8 mentions in 7 episodes 1 per episode
- 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
- 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
- 20VC: 500 Startups' Dave McClure on Whether Unicorns Are Necessary For Venture Returns & Why Ownership Is Not The Math To Think About When Investing
- 20VC: Creating A Competitive Process Between VCs & Having Bill Gurley As A Board Member with Aaron Hirschhorn, Founder & CEO @ DogVacay
- 20VC: Sprig's Gagan Biyani on The 3 Principles Of Fundraising and Building The World's Largest Restaurant
- 20 VC: Niccolo De Masi @ Glu Mobile on Private Market Valuations, Being A Public Market CEO & The Trends Of Mobile Gaming
- 20VC FF 028: Where To Start Your Startup and Single Founder vs Co-Founder Model with Richard Hanson, Co-Founder & CEO @ HiringScreen
- every mention in 2016, scene by scene →
2015 18 mentions in 7 episodes 3 per episode
- FF 011: 'The Savviest Investors Don't Ask What If' with Ben Nader, CEO & Founder @ Butterfleye
- 20 VC FF 018: Brian Wong, Founder @ Kiip on Raising $30m in VC Funding by 24
- 20 VC FF 026: Ryan Hoover, Founder @ ProductHunt on Relationship Building, Habit Forming and The Vision for ProductHunt
- 20 VC 092: The Repeatable Playbook of SaaS with Ed Sim, Founding Partner @ BoldStart Ventures
- 20 VC 079: BETAWORKS WEEK: East vs West Coast Investing with Peter Rojas, EIR @ Betaworks, Co-Founder @ Weblogs & Engadget
- 20 VC 071: Pre-Seed Investing, Why Now Is The Best Time with Nicholas Chirls @ Notation Capital
- James Altucher: Ideas, Investing and Entrepreneurs
- every mention in 2015, scene by scene →
Everything said about Jason Calacanis, oldest first
Jun 1, 2015 bullish
Jun 1, 2015 neutral
Jun 1, 2015 neutral
Calacanis Synergizes Live Events to Fill 40% of Podcast Content
“You have to remember, when I do the launch festival three days, I do probably 25 interviews. We take the top 10 of those based on how the crowd reacts, and we make them into probably eight episodes. Some of them are like, you know, you put two together. So may…”
Jun 1, 2015
Calacanis: Uber and Thumbtack had a combined $9M valuation at first round
“Thumbtack and Uber, You know, they were nine million dollars, and they're like, well, we only want one million dollars more. I was like, no, no, combined. Their valuation was nine million combined when I invested in their first rounds”
Jun 1, 2015 bullish
Jun 1, 2015 positive
Jun 1, 2015
Calacanis: Podcasting requires two years of unpaid work to succeed
“The only way it worked is if some crazy maniac with a really good reputation and network was willing to work for free for a couple of years, and then the podcast would magically work in year four or five, like Adam Carolla's is, or Kevin Pollack's is, or Leo L…”
Jun 1, 2015 bullish
Calacanis: This Week in Startups will hit $1 million in annual revenue
“This week in startups is now, it's 5000 dollars in advertisement. We do a 104 episodes a year, two ads, so it's 208 ads a year. Some people get discounts. I mean, it's going to hit a million dollars in revenue. And there's like four or five full-time people on…”
Jun 1, 2015 negative
Jun 1, 2015
Calacanis: Enduring repeated career crises builds fearlessness and emotional resilience
“I think now, you know, as you get older, you can kind of, you see the arc of your career, so you don't let the little things, you know, you can survive stuff. So, like, surviving the internet bubble bursting, surviving nine-eleven, surviving the financial cris…”
Jun 1, 2015
Jun 1, 2015 positive
Jun 1, 2015 positive
Calacanis Chooses VC Partners Over Firms, Recommends Roelof Botha
“Listen, you know, I like partners, not firms, so I would step back, and I would, you know, do it that way, and then I would also look at who's good at media, right? So I would look at who has backed media companies, who wants to work with media companies, who …”
Jun 1, 2015
Jun 1, 2015
Calacanis has dissolved investment deals and returned equity to incompatible founders
“If I don't like the person, I literally have had one or two people who, you know, wasn't working out, and I just said to them, like, listen, take my money, give me my money back, take your stock back, we'll rip up the agreement, I don't need you to pay me what…”
Jun 1, 2015
Jun 1, 2015
Jun 1, 2015
Jun 1, 2015 negative
Jun 1, 2015 bullish
Jason Calacanis: Smartphone supply chain advances are driving drone convergence
“Drones, three-D printing, and virtual reality and machine learning and the on-demand economy, these, like, sort of trends are all starting to merge and sort of build off each other, and really build off the back of smartphones, whether it's the sensors in the …”
Jun 1, 2015 positive
Jun 1, 2015 bullish
Sep 4, 2015
Aug 14, 2017
Aug 14, 2017 negative
Aug 14, 2017 positive
Aug 14, 2017 negative
Calacanis: YC partners fully fund top 10 batch companies before Demo Day
“People who are part of their inner circle invest in the companies long before the schmucks who come to Demo Day get a chance to invest in them. So pretty much if you're in the audience at Demo Day, you're kind of the sucker at the table. The best 10 companies …”
Aug 14, 2017 negative
Aug 14, 2017
Oct 18, 2023 bullish
Oct 23, 2025 bearish
Calacanis: Enterprise AI Buyer Demand Will Drop to 5% Within 24 Months
“They got the price of the vendor right, but the soft costs, the training, the onboarding, the business process change were the highest it's ever been in their lifetimes. They're not going to do that every year. And so we may go back to five percent being in ma…”
Oct 23, 2025 bearish
Oct 23, 2025 negative
Oct 23, 2025 bullish
Calacanis: Present VC market is the easiest ever for investing
“Yeah, because there's because there's so many entrepreneurs. There's so much change. Change is when you make money, right? Change is when you make money in venture. There's so much change. There's so many great entrepreneurs, and we don't have to worry about g…”
Oct 23, 2025 bullish
Oct 23, 2025 bullish
Calacanis: AI apps will consume 1,000x more compute via continuous inference
“Smart folks are going to figure out already how to use a thousand times more inference and compute than we're using today. Because instead of running a little one-off thing, right, or even using lovable for an hour, and then letting the servers with no load go…”
Dec 18, 2025 bearish
Jason Calacanis: Cursor will maim Figma and SaaS incumbents by lowering NRR
“I think the bigger risk for so many vendors is that it maims Figma... HubSpot and box and even anthropic using it, they don't leave, they renew, they don't buy as many seats, right? Because the team is also using cursor, but of course they don't churn. The log…”
Dec 18, 2025 neutral
Calacanis: UiPath NRR dropped from 140% at IPO to 107%
“Come, 1.8 billion in ARR, but he's got 98% GRR and a 107% NRR. Okay. So mathematically one problem is his NRR has fallen from the 140% peak at the IPO because people aren't buying that much more for UiPath, but he's got 98% GRR, 98% retention.”
Dec 18, 2025 negative
Calacanis: One-year equity cliffs hinder poaching talent in competitive markets
“And so on the one hand, it seems like a dumb idea, like you're creating mercenaries and perhaps you are, but in the age and you're asking someone that's 18 months into somebody else to leave and wait 12 months to make a dollar. That can be a tough sell in, in,…”
Mar 5, 2026 neutral
Jun 4, 2026 positive
Jun 4, 2026 positive
Jun 4, 2026 bearish
Calacanis: AI Startups Will Eventually Re-Bloat to Historic Headcounts
“And so even, and so our startups that we're excited about, I think ultimately they will achieve the same historic level of bloat, maybe half the size, but they will get as bloated as they can because they will have much larger, broader product lines.”