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.

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