Naval’s $500 VC fund, the Maduro Polymarket scandal, and NYT defends theft and murder | E2280

Naval’s $500 VC fund, the Maduro Polymarket scandal, and NYT defends theft and murder | E2280

Author: Jason Calacanis April 25, 2026 Duration: 50:20

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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

“Thinking in Bets” by Annie Duke: https://www.amazon.com/Thinking-Bets-Making-Smarter-Decisions/dp/0735216355

“Queen of Chess” trailer: https://www.youtube.com/watch?v=8pmJgtLKBXg

Greenlight app: https://greenlight.com/

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Every week, Jason Calacanis dives headfirst into the swirling vortex of Silicon Valley and global tech with This Week in Startups. It’s a direct line to the conversations shaping our digital future, moving far beyond surface-level news. You’ll hear Jason’s unfiltered analysis on everything from market shifts and media trends to the underlying mechanics of building a business, all delivered with a blend of enthusiasm and seasoned skepticism. The core of this podcast, however, lies in the guests. Jason sits down with the very people driving change-founders who have scaled impossible heights, operators managing daily chaos, and investors who spot trends before they become obvious. These conversations are less like formal interviews and more like insider debriefs, pulling back the curtain on real strategies, painful failures, and unexpected successes. For anyone curious about how technology is built, funded, and ultimately changes the world, this series offers a front-row seat. It’s the context behind the headlines, providing a deeper understanding of the forces at play in startups and technology. Tune in for a consistently engaging and insightful look at the ecosystem, straight from someone who lives and breathes it.
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