Learn by Making Small Bets

Jason Calacanis argues investors should experiment with small stakes, ignore weak social media criticism, and use markets to build judgment.

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This Week In Startups is made possible by:

Northwest Registered Agent - https://northwestregisteredagent.com/twist

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Today’s show:

It’s a News and Off-Duty weekend roundup!

AngelList’s USVC fund is open to anyone with $500, but it’s getting pushback on social media. Do the critics have a point?

A Special Forces soldier made $409K betting on the military’s capture of Venezuelan leader Nicolas Maduro. Is the world just a big casino now?

And a NYT podcast defends shoplifting and explores “social murder.” Find out why Jason says they crossed the line.

Plus: Why you should teach your kids about investment and more, Off-Duty streaming and book recommendations.

Related Links

USVC: https://usvc.com/

AngelList: https://www.angellist.com/

Naval Ravikant on X: https://x.com/naval

“Don’t Listen to the Peanut Gallery; USVC is a Watershed Moment” by Hari Raghavan: https://x.com/haridigresses/status/2047503944839016681

@Covered_Call USVC tweet: https://x.com/covered_call/status/2047020060900733306

Forge Global: https://forgeglobal.com/

Calm: https://www.calm.com/

Full DOJ indictment of Gannon Ken Van Dyke: https://www.justice.gov/opa/pr/us-soldier-charged-using-classified-information-profit-prediction-market-bets

NYT “The Opinions” podcast: “The Rich Don’t Play by the Rules. So Why Should I?” https://www.nytimes.com/video/opinion/100000010849055/the-rich-dont-play-by-the-rules-so-why-should-i.html

Hasn Piker on Twitch: https://www.twitch.tv/hasanabi

New Yorker: Jia Tolentino: https://www.newyorker.com/contributors/jia-tolentino

NYT: Nadja Spiegelman: https://www.nytimes.com/by/nadja-spiegelman

Jia Tolentino on X: https://x.com/jiatolentino

Garry Kasparov on X: https://x.com/kasparov63

Prof G Media: https://www.profgmedia.com/

Kids Investment Club: https://www.kidsinvestmentclub.com/

Time stamps:0:00 Intro

1:18 Naval's $500 VC Fund Explained

5:54 Should You Trust Critics With 2K Followers?

7:21 Learn By Betting — Jason's Philosophy

10:10 Northwest Registered Agent - Get more when you start your business with Northwest. In 10 clicks and 10 minutes, you can form your company and walk away with a real business identity — Learn more at https://www.northwestregisteredagent.com/twist

12:30 The Maduro Polymarket Scandal

13:28 Should the Military Bet on Missions?

19:55 LinkedIn Jobs - Hire right, the first time. Post your first job and get $100 off towards your job post at https://LinkedIn.com/twist

29:32 NYT Defends Theft & "Social Murder"

30:28 There Is No Moral Equivalence

33:41 The Nepo Baby Behind the Article

35:42 Prof G's "Resist & Unsubscribe" Movement

37:54 Walk The Walk — Hasan, Bernie & Performative Outrage

44:49 Teaching Kids About Money

48:21 The Rich Get Richer & The Poor Stay Poor

Off Duty Recommendations

“The Complete Maus” by Art Spiegelman: https://www.amazon.com/Complete-Maus-Art-Spiegelman/dp/0679406417