👉 Take the free 10-day FiiRE guide to find out how financially flexible you actually are: https://affordanything.com/fiire Jack Raines got rich in his 20s — including turning $6,000 into $400,000 trading SPACs. But some of his best financial advice for your 20s has very little to do with making more money. In this episode, we talk about career risk, golden handcuffs, status, feeling behind, when it makes sense to prioritize money, and the trading experience that turned $6,000 into $400,000 before costing him roughly $200,000 from the peak. Jack Raines is a writer, investor at Slow Ventures, and author of Young Money: A Field Guide to Wealth and Purpose in Your Twenties. Chapters: (2:00) He liked his boss on a dating app (6:57) Two very different ways to spend your twenties (17:56) Why grad school became his built-in sabbatical (19:16) Why 30 gets judged harder than 24 (34:12) The real cause of career apathy (39:20) His best fix for feeling stuck (46:27) Same decision, right at 24, wrong at 34 (1:01:43) What's really keeping you in a job you hate (1:14:12) Why more money doesn't fix stress (1:17:56) Turning $6,000 into $400,000 in a stock bubble ❓GOT A QUESTION? WE'D LOVE TO HEAR IT https://affordanything.com/voicemail 🎧 NEVER MISS AN EPISODE Apple Podcasts: https://affordanything.com/applepodcasts Spotify: http://affordanything.com/spotify 🤗JOIN OUR PRIVATE COMMUNITY: https://affordanything.com/community 🤗STAY IN THE LOOP: https://affordanything.com/newsletter 🛠 TOOLS AND RESOURCES: 👉 Jack's new book, Young Money: A Field Guide to Wealth and Purpose in Your Twenties → https://amzn.to/4xGw67h 👉 Nick Maggiulli's The Wealth Ladder, the six-level wealth framework Paula references → https://amzn.to/4wydTrF 👀 WATCH THIS VIDEO NEXT: Nick Maggiulli: The Wealth Ladder Has Six Rungs (and Most People Never Climb Past Four) → https://www.youtube.com/watch?v=K6-AudcRa2o 👋 SAY HI ON SOCIAL: Facebook: https://facebook.com/affordanything Instagram: https://instagram.com/paulapant X: https://x.com/affordanything #PersonalFinance #GoldenHandcuffs #FinancialFreedom https://youtu.be/YZ5RriISKk8?si=dCnwCaE5Aw2o3Egs