Jun 1, 2015 · 55m · 20vc
Jason Calacanis: The World's Greatest Angel Investor
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of The 20 Minute VC, host Harry Stebbings interviews angel investor and media host Jason Calacanis about his investment philosophy, podcasting operations, and personal backstory. Calacanis shares insights on identifying passionate founders, navigating venture capital dynamics, overcoming personal adversity, and his goal of becoming the greatest angel investor in history.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 12.3% of the talking time here. How this is scored →
Harry as informed peer 3.1 Guest teaching 4.8 Guest disagreement 2.4 Harry pushing back 1.9
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 15:45 Jason's email rant against elite VC firm
Jason reads a scorching email he sent to top-tier VCs who passed off his recommended founders to junior staff, telling them directly that they are playing the game wrong.
Hardest push from Harry ▶ 8:15 Harry pushing Jason on angel rankingsHarry refuses to accept Jason placing himself merely in the top 10, pushing him into the top 3 while challenging Sacca's current active status as an angel investor.
Biggest teaching moment ▶ 45:40 Jason schooling YC founders on valuation trapsJason breaks down why YC founders taking $10 million valuations from unhelpful dentists and unsophisticated angels are making a severe strategic mistake compared to early Uber and Thumbtack rounds.
Harry holds his own ▶ 8:15 Harry naming elite angels and market benchmarksHarry demonstrates strong market expertise by immediately benchmark-matching Jason against Chris Sacca, Tim Ferriss, and Gil Penchina, expertly driving the industry comparison.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| The Economics, History, and Future of Podcasting | 2 | 5 | 1 | 1 | Harry asks broad questions about podcasting economics and mentions the audio app Raw. Jason details his six-year history in podcasting, advertising revenue metrics ($5k per sponsor), and platform distribution trends. | |
| Investing in Uber and Betting on Serial Founders | 3 | 4 | 1 | 1 | Harry demonstrates familiarity with Red Swoosh's exit size and Jason's past commentary on founder passion. Jason explains his thesis on betting on founders during their third or fourth swing at bat. | |
| Spotting Entrepreneurial Passion and Setting Historic Angel Goals | 2 | 5 | 2 | 2 | Jason outlines his psychological filter for evaluating founder passion and states his explicit ambition to be the greatest angel investor in history, placing himself in the top 10. | |
| Ranking Top Angel Investors and Exploring Dual Scorecards | 6 | 4 | 1 | 5 | Harry actively challenges Jason's modest top 10 ranking by placing him in the top 3 alongside Sacca, Ferriss, and Penchina, while questioning Sacca's current status as an active angel. Jason responds by detailing his external and internal personal scorecards. | |
| Collaborative Investing and Evolving Beyond a Cutthroat Reputation | 3 | 4 | 2 | 3 | Harry asks probing questions about work-life balance and public perception. Jason discusses syndicate collaboration with top VCs and candidly addresses his past reputation as a aggressive public fighter. | |
| Confronting High-Profile VCs Over Respecting Founder Time | 4 | 4 | 6 | 4 | Jason recounts a confrontation with a top VC firm, reading a scathing email he sent them for disrespecting his portfolio founders. Harry attempts to name the firm, while Jason forcefully condemns VCs who do not respect founder time. | |
| Dream Venture Partners and Launch Content Syndication Strategy | 3 | 4 | 1 | 1 | Harry asks Jason to select his dream syndicate team. Jason lists core partners and explains his content strategy for syndicating Launch incubator and conference material into his podcast feed. | |
| Refining Interview Craft and Long-Term Media Trajectory | 3 | 5 | 2 | 3 | Harry asks about key inflection points in Jason's broadcasting career. Jason candidly admits his early shows sucked and outlines his long-term ambition to become the world's best interviewer. | |
| Scaling Launch Conferences and Reflecting on Iconic Interviews | 2 | 4 | 1 | 1 | Harry asks about future plans for Launch and favorite podcast guests. Jason breaks down audience preferences across news roundtables, deep profiles, and tactical tutorials, while reflecting humbly on his Brooklyn roots. | |
| Maintaining Hunger Through Work Ethic and Early Hardships | 3 | 5 | 1 | 1 | Harry asks if Jason ever stops to celebrate achievements. Jason shares his mental rule of putting framed press coverage in the closet to stay hungry, reflecting on his early days working three manual labor jobs. | |
| Overcoming Father's Business Failure and Early Career Crises | 2 | 5 | 1 | 1 | Harry inquires about pivotal life moments. Jason recounts watching federal agents seize his father's bar at gunpoint for back taxes when he was 17, and surviving both the dot-com crash and 9/11 in New York. | |
| Gaining Perspective, Mindset Practices, and Relational Capital | 3 | 5 | 2 | 1 | Harry references Jason's early investment in Calm. Jason shares his philosophy on gaining perspective through hardship, emphasizing that business failure is insignificant compared to personal loss. | |
| Tesla Serial Number One and Recent Investments | 4 | 4 | 1 | 2 | Harry brings up Jason's ownership of Tesla Model S serial #1 and asks what price would convince him to sell. Jason lists recent investments in Bento, One Drop, Hyperloop, Butterfly, and Birdie. | |
| Evaluating Drones, 3D Printing, and Virtual Reality Simulations | 3 | 5 | 1 | 1 | Harry asks what technologies have recently impressed Jason. Jason outlines the convergence of drones, 3D printing, machine learning, and VR, illustrating how remote VR training could democratize complex skills like surgery. | |
| Critiquing Higher Education Debt and Analyzing Bitcoin's Trajectory | 3 | 6 | 6 | 1 | Harry asks about higher education and Bitcoin. Jason strongly critiques university debt as indentured servitude and labels Bitcoin founders as overhyped with poor execution. | |
| Navigating Tech Valuations and Launch Incubator Model | 3 | 7 | 6 | 2 | Jason critiques Y Combinator valuation inflation ($10M cap for early startups) and warns against taking money from inexperienced angel investors, contrasting it with his small-cohort incubator model. | |
| Critiquing Spray-and-Pray Capital and Pitch Best Practices | 4 | 6 | 6 | 2 | Harry asks directly about Dave McClure's investment methodology. Jason sharply criticizes the spray-and-pray approach, advising high-volume accelerators to do half as many deals twice as well. | |
| Analyzing Elon Musk's Inhuman Fearlessness and Business Supremacy | 3 | 5 | 2 | 3 | Harry asks about Elon Musk's influence. Jason analyzes Musk's superhuman risk tolerance, quoting Musk's advice that most people overestimate downside risk. |
Statements from this episode (36)
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…”
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…”
Calacanis: This Week in Startups averages 150,000 downloads per episode
“150,000 downloads per episode.”
Calacanis: Travis Kalanick Was Sued for $250B Over Scour
“He had just been sued for a quarter of a trillion dollars by the movie companies.”
Calacanis: Serial Founders Peak on Their Third or Fourth Startup
“People on their third, fourth swing at bat can do really well, whether it's Evan Williams with Twitter. He did he did Odeo and then blogger before that, but Twitter obviously was his third time up at bat. So I love founders when they're at the third time at ba…”
Jason Calacanis passed on early angel investments in Twitter and Zynga
“I had passed on investing in Twitter and I passed on investing in Zingo, which are two of my very good friends.”
Calacanis aims to become the greatest angel investor of all time
“I'm gonna be one of the greatest angel investors of all time, which is really my goal right now. I wanna be the best angel investor in the history of angel investing”
Calacanis ranks himself among the top 10 most desirable angel investors
“In terms of desirability, I'm definitely in the top 10.”
Calacanis: Chris Sacca is hands down the top angel investor
“So if you were doing SaaS, you know, I put Gil ahead of myself and Tim Ferriss, and maybe, you know, on par with Sokka. I mean, Sokka's just a whole nother level. So I put Sokka as number one hands down right now.”
Calacanis: Competitive motivation is immature, yet exceptionally powerful
“If you look at Maslow's hierarchy of needs, if you look at the dynamics and the psychology of motivation, competitive motivation is a very immature motivation. It also happens to be perhaps one of the most powerful.”
Calacanis details early Uber investment alongside Bill Gurley and Shervin Pishevar
“I was the angel investor in Uber, Bill Gurley did the A round, Shervin did the B”
Calacanis was Thumbtack's second investor before bringing Sequoia to the deal
“I was the second investor in Thumbtack after Marco's parents, and then roll off, I brought him The A round, I brought him the B round, I brought him the C round, and Roloff eventually and Sequoia did the B round.”
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 …”
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…”
Calacanis: Displaying past press clippings breeds complacency
“Once I start putting that shit on the wall, I'm going to start living in the past, and I'm actually going to think like, I'm successful.”
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…”
Calacanis: Mahalo laid off 75 staff following Google Panda update
“So, like, surviving the internet bubble bursting, surviving nine-eleven, surviving the financial crisis, surviving Mahalo getting hit by the Google Panda update, laying 75 people off, all this shit.”
Calacanis refuses to do business with people he isn't friends with
“So I don't really work with people if I'm not friendly with them. Like, if I don't have a friendship with you know, I don't really need to be in business with you.”
Calacanis pledges to invest in Travis Kalanick's next company if Uber fails
“Travis and I are very good friends, you know, from Uber and have been for a long time. And we, I would be good friends with him if his company failed, and I would invest in his next company”
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…”
Calacanis owns Tesla Model S serial number 00001
“Yeah, I have serial number zero zero zero zero one, yeah.”
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 …”
Jason Calacanis: VR will succeed in video games, adult entertainment, and education
“So I think that stuff is really going to work for video games and adult entertainment, and it could work for education.”
Jason Calacanis: College is the biggest ripoff on the planet
“College is the biggest ripoff on the planet.”
Calacanis: Limit college debt to one year's prospective salary
“I don't think you should go more than one year salary in debt.”
Calacanis: Bitcoin has an equal chance of reaching $1,000 or $0
“I think Bitcoin has an equal chance of going to zero as it does to a thousand dollars again.”
Calacanis: Bitcoin founders are all hype and lack execution
“Really the founders in the Bitcoin space are not doing a great job. I mean, I think they're all hype and very little execution.”
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”
Calacanis: Far more tech unicorns exist outside Y Combinator than inside
“There's many more unicorns outside of there's many more unicorns outside of Y Combinator than in it.”
Calacanis: 500 Startups would be twice as successful doing half as many deals
“I think if they can maybe, I think they would be twice as successful if they did half as much. That would be my, that is my advice to Dave. Do half as many deals, but do them twice as well”
Calacanis: Accelerator cohorts of 120 companies harm participating startups
“I do think that a 120 companies at Y Combinator and whatever Dave's doing is, it's just, it's not good for the startups.”
Calacanis: Y Combinator triples startup valuations while Launch Incubator doubles them
“I would say that Y Combinator's program does triple your valuation, and mine probably only doubles it, you know.”