Jul 28, 2022 · 1h 12m · startup-ideas
How To Pick Startup Winners With Jason Calacanis
0:00 / 0:00
▶ Watch on YouTube →
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Angel investor Jason Calacanis joins hosts Kyle O'Brien and Greg Isenberg to share actionable frameworks for startup investing, dissect crypto market speculation versus Web3 utility, evaluate public equities, and reflect on media ventures and life perspective.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Greg holds 2.2% of the talking time here. How this is scored →
Greg as informed peer 3.1 Guest teaching 4.6 Guest disagreement 2.4 Greg pushing back 1.6
speaking balance: gold is Greg, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 28:40 Jason Dismisses Toxic Bitcoin Bros
Jason aggressively mocks crypto maximalists who insult skeptics, arguing that every technology in history is eventually superseded and noting he made seven figures while maintaining intellectual honesty.
Hardest push from Greg ▶ 2:30 Kyle Challenges the VC Crypto Dumping PremiseKyle directly questions Jason's viral thesis on VC crypto dumping, arguing that mandatory multi-year vesting schedules for venture investors would prevent short-term retail dumping.
Biggest teaching moment ▶ 8:20 Jason Unpacks Offshore Foundation ArbitrageJason breaks down how prominent venture firms paid massive legal fees to set up Panama foundations to bypass securities laws and liquidate pre-revenue tokens onto retail investors.
Greg holds their own ▶ 46:50 Hosts Feed Balance Sheet Metrics for Live ValuationKyle and Greg demonstrate strong market fluency by quickly pulling up Snap's $4.5B top line and $5B cash balance, allowing them to collaborate with Jason on EV-to-earnings math in real time.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Greg as informed peer | Guest teaching | Guest disagreement | Greg pushing back | Why |
|---|---|---|---|---|---|---|
| Angel Investing Guidelines and Check Sizing | 0 | 1 | 1 | 0 | Introductory cold open excerpt of Jason giving angel investing rules, followed immediately by an ad read by Kyle. No active interview dialogue occurs in this initial segment. | |
| Crypto Liquidity Exploitation and Investor Accreditation | 4 | 7 | 4 | 4 | Kyle questions Jason on VC crypto dumping and asks if multi-year vesting schedules refute the cynical take. Jason delivers an extensive masterclass on offshore legal structures in Panama, regulatory accreditation tests, and how retail investors end up as bag holders. | |
| Web3 Utility and Contract-Based NFT Memberships | 2 | 6 | 2 | 1 | Greg asks an open-ended question about an optimistic 5-10 year view of Web3. Jason reframes the question across the 17 underlying technologies and explains NFT utility in membership models like Soho House or music festivals. | |
| Sponsor Message: Engineering Talent on Lemon.io | 4 | 5 | 2 | 2 | Following a mid-roll ad read, Jason outlines DAO governance issues and slow blockchain databases. Kyle and Greg contribute their own experiences walking away from a quick-cash NFT project with friends due to SEC and moral concerns. | |
| Market Cycles, Valuation Sanity, and Startup Discipline | 4 | 6 | 4 | 3 | Jason draws poker analogies to angel investing and recounts sparring with Bitcoin maximalists over technological obsolescence. Kyle pushes Jason to consider institutional LPs holding the bag on venture crypto markups, but Jason clarifies that sophisticated LPs know the risks. | |
| Public Equities Trading, J-Trading, and Founder Evaluation | 4 | 5 | 2 | 1 | Kyle asks about financial disclaimer culture, prompting Jason to share his public equity 'J-trading' thesis across Stitch Fix, Disney, and Amazon. Kyle shares his own hedge fund interview blunder pitching Stitch Fix, and Jason teaches poker decision-making lessons from Annie Duke. | |
| Public Market Stock Breakdown: Snap vs. BuzzFeed | 6 | 5 | 3 | 2 | Kyle and Greg prompt Jason to evaluate beaten-down tech stocks like Snap and BuzzFeed. The hosts supply key balance sheet data (market cap, revenue, cash reserves), enabling Jason to calculate enterprise multiples live and compare Snap's product innovation to BuzzFeed's terminal media model. | |
| All-In Podcast Dynamics and Future Media Projects | 2 | 4 | 3 | 1 | Kyle asks about the backstage friction and business lessons of the All-In podcast. Jason details navigating four alpha co-hosts, summit equity negotiations, and why he decided to launch separate solo podcasts instead. | |
| Life Perspective, Peak Experiences, and Fatherhood | 2 | 2 | 1 | 0 | Kyle asks about Jason's internal drive. Jason reflects candidly on mortality, his Tahoe mountain lion encounter, and rediscovering childhood joy with his daughters, while Kyle bonds over his newborn son. |
Statements from this episode (20)
Calacanis bought Bitcoin at $2–$3 and $100–$200
“I bought Bitcoin at like two or three dollars, and then again at a 102 hundred dollars.”
Calacanis: 99% of crypto projects are built by grifters or incompetents
“I do think 99% of the ICOs in crypto projects have never materialized into anything reasonable. And I think a significant portion of them have been built by either grifters, incompetent people, or some combination of both.”
Calacanis: VCs paid high legal fees specifically to dump tokens
“You set up these structures, you paid all this legal money because you knew you were going to dump. You knew you were going to clear these positions and you knew it was going to be lucrative. That's why you went through the expense instead of just raising mone…”
Calacanis: Crypto market downturn will trigger hundreds of lawsuits
“And I think this stress test is gonna result in countless And I mean countless lawsuits. Hundreds of lawsuits.”
Calacanis: Blockchain is a terrible database and will always be slow
“The blockchain as a database sucks. You know, everybody knows that it's slow and it's never gonna get super fast. At least not when compared to You know you know, modern day technology that doesn't have to, you know, be immutable and distributed. So it's alway…”
O'Brien: DAOs fail as corporate governance during company crises
“Centralization is good in times of crisis. And like, I think that across decision making authority too. And so when you talk about Dow's, like, I think a lot of the use cases you talked about are interesting in the context of a doubt where you have like you kn…”
Calacanis: Consumers will prefer centralized brands over decentralized crypto versions
“I don't think most consumers would pick the decentralized crypto version over the centralized trusted brand. People are underestimating centralized trusted brands.”
O'Brien: NFT project founders will face lawsuits and SEC enforcement within two years
“And honestly, probably likely that like two years from now, a lot of these people get sued or the SEC comes after you, and I don't want to get banned from, you know, for doing something stupid like that.”
Calacanis: Angel investors should only back revenue-generating companies for first 20 deals
“Like I literally tell people only invest in companies that have products in market and have revenue for your first 20 investments as an angel.”
Calacanis: Bitcoin will eventually be replaced by superior technology
“Bitcoin is a great technology. It's been proven pretty robustly over a decade, but it will be replaced by a better technology. All technologies replaced eventually by a better technology”
Calacanis: Henry Blodget offered me 5% of Insider and I passed
“Yeah, which used to be Silicon Alley Insider, and you offered me five percent of it because I had Silicon Alley Reporter magazine, and I said, nah, you know, just keep it.”
Calacanis bought 5,000 Stitch Fix shares after Bill Gurley's purchase
“I saw Bill Gurley buy a million shares. I know Bill Gurley. He's really smart. He's been with the company forever. Bill Gurley's buying a million shares. Sure. I'll buy my, I bought 5000 shares.”
Calacanis: Disney's streaming bundle will reach one billion subscribers
“I think that between Disney, Hulu, ESPN plus, they're going to get to a billion subscribers.”
Calacanis: LAUNCH averages 70 meetings and two investments per week
“I have 11, I think 10 or 11 people on the investment team at launch. Now we do about 70 meetings a week, probably 50, 60 of them are introductory meetings. And we invest in two companies a week on average. And one of them tends to be a follow on one tends to b…”
Calacanis: Founder charisma can be faked, great products cannot
“You can become really inspired by a founder and they're, they've been trained on how to be charismatic. Now they've kind of unpacked what charisma is. And how to sort of fake it. So it's quite theatrical at times. But you can't fake a great product. You can't …”
Calacanis: Snap CEO Evan Spiegel is a product genius
“And I think Evan Spiegel is a product genius. Like he truly is. If you think about the things Zuckerberg copied from him, ephemeral messaging, lenses, stories, I mean, and glasses.”
Calacanis: Digital journalism is flawed and BuzzFeed could hit zero
“Journalism is a terrible business. There's no path to viral growth here. Every time you grow in order to grow their top line, they're going to have expense. So if you want to get more page views, you're going to have to hire more expensive entitled writers as …”
Calacanis commits $1M to $2M to learn public equity trading
“The way I'm looking at the million or two million dollars I'm gonna put into J trading is that's to get me the edge. That's my MBA.”