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5 min readHow To Pick Startup Winners With Jason Calacanis
Jason Calacanis has invested in 350 companies, runs the largest syndicate in the world with 11,000 accredited investors, and has done over 260 deals. But when he gives advice to new angel investors, his first rule is deliberately boring: for your first 20 investments, only put money into companies that already have products in market and revenue. And put the smallest amount you can — if the minimum is $5,000, ask if you can do $2,000 or even $500. He has people do this to him all the time, and he says yes.
The reasoning is straightforward. New investors have no edge yet. They need to learn how to evaluate deals without risking meaningful capital. Calacanis compares it to learning poker: you can learn the game by buying into a $35 tournament at Hollywood Park Casino, not by sitting down at a $25,000 high-stakes table. The same principle applies to angel investing. His course, Angel University, costs about $300 — all proceeds go to charity — and he considers that a reasonable price for the friction it creates. The book is essentially free. The first investment should be $4,000 or $5,000, and if the minimum is higher, ask if you can do less. He has people ask to put in $500, and he says yes if there is room.
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What you'll learn
- 1 (00:00) **First 20 Angel Investments: Only Bet on Revenue** - Jason's core advice for new angel investors: only invest in companies with products in market and revenue for your first 20 deals, and put in the smallest amount possible.
- 2 (04:04) **VC Liquidity in Crypto: The "Dump on Retail" Problem** - Jason explains why he believes VCs dumping liquid tokens on retail at massive markups is problematic, and why the SEC is likely to act.
- 3 (08:10) **The "I'm an Idiot" Test & Accreditation Reform** - Jason argues for a simple test to let anyone become an accredited investor, rather than basing it on net worth.
- 4 (13:51) **Optimistic Web3 Future: NFTs with Rights & DAOs** - Jason identifies the few Web3 technologies he believes have real, lasting potential.
- 5 (21:22) **Why Most Crypto is Overhyped** - Jason explains why blockchain as a database is slow, why most consumers want central authority in a crisis, and how the ecosystem got co-opted by "bag flippers."
- 6 (27:09) **The NFT Grift: Low Morals, Easy Money** - A discussion on how the 10k PFP NFT cycle was pure arbitrage for people with low morals, and how the host and his co-founder walked away from a project for that reason.
- 7 (30:29) **The Poker Analogy for Investing: Process Over Outcome** - Jason explains his investing philosophy as a process of constant refinement, using a poker lesson from Annie Duke as a metaphor.
+ Full timestamped outline available in the app
Show Notes
Are you ready to start angel investing? In today's episode, we share the secret to creating long-term wealth, explain how to become a “sophisticated” investor, and discuss the downsides of crypto. Hosts Sahil Bloom and Greg Isenberg are joined by guest Jason Calacanis, the creator behind the All-In Podcast, a serial angel investor, and a leading entrepreneurial author. Jason explains the entrance costs to investing, shares why people need to validate their research, and then everyone places their bets on this week's “hot” stocks.
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FROM THIS EPISODE
Jason Calacanis https://twitter.com/Jason
Sahil Bloom: https://twitter.com/SahilBloom
Greg Isenberg: https://twitter.com/gregisenberg
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