You Can't Buy Back Your 20’s — with Jack Raines

#740: Jack Raines turned $6,000 into $400,000 trading blank-check stocks during the 2020–2021 bubble — and he says it was some of the least fun money he's ever made.

Jack Raines is a writer and investor at Slow Ventures, and the author of the new book Young Money: A Field Guide to Wealth and Purpose in Your Twenties.

In this episode, we discuss:

Why "golden handcuffs" are almost always a choice, not a trap

How to tell if you're staying in a job for the right reasons, or just fear

Why the same decision can be exactly right at 24 and wrong at 34

What actually helps when comparison and "falling behind" turn into apathy

How he turned $6,000 into $400,000 trading a stock bubble, then gave much of it back

Why hitting your number rarely feels like the finish line people expect

Two questions worth asking before you spend years on something that isn't working

This one's for anyone who feels behind, stuck, or unsure if their current path is a smart trade-off or just fear in disguise — Jack's way of thinking about money and time might be the reset you need.

⏱️ TIMESTAMPS

Note: Timestamps may vary slightly depending on dynamic ad placements.

(02:00) He liked his boss on a dating app

(06:57) 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

(01:01:43) What's really keeping you in a job you hate

(01:14:12) Why more money doesn't fix stress

(01:17:56) Turning $6,000 into $400,000 in a stock bubble

🔗 RESOURCES MENTIONED

👉 Take the free 10-day FiiRE money-mindset workbook: if "I make too much to quit" sounds familiar, this helps you find out if that's actually true. → https://affordanything.com/fiire

👉 Jack's new book, Young Money: A Field Guide to Wealth and Purpose in Your Twenties → https://jackraines.blog/book

👉 Nick Maggiulli's The Wealth Ladder, the six-level wealth framework Paula references → https://www.amazon.com/Wealth-Ladder-Proven-Strategies-Financial/dp/0593854039

👉 Freedom, the app Jack and Paula both use to block social media and protect focus time → https://freedom.to

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