Why You Should Take More Risks in Your 20s (ft. Jack Raines)

Why You Should Take More Risks in Your 20s (ft. Jack Raines)

September 7, 2026 · 37 min

About this episode

Jack Raines discusses the importance of taking risks in your 20s and shares insights from his career and new book.

Jack Raines, Venture Capitalist and Author, joins The Rundown to explain why your 20s might be the best time to take bigger risks with your career, money and life. He shares how he turned $6,000 into $400,000 trading SPACs and eventually built a career through writing and posting online. Jack also breaks down the philosophy behind his new book, Young Money , and why he thinks young people should worry less about optimizing every dollar and more about maximizing the unique opportunities of early adulthood. Plus, he and Zaid discuss the value of making financial mistakes while the stakes are still low, building an unconventional career and knowing when to spend money on experiences instead of saving it.

More episodes of The Rundown

Explore listener stats, chart rankings, contacts and more on the The Rundown podcast page.