Aug. 4, 2026

INTERVIEW | Make Money by Building Wealth, Writing Online, and Creating Career Opportunities with Jack Raines

INTERVIEW | Make Money by Building Wealth, Writing Online, and Creating Career Opportunities with Jack Raines
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Jack Raines is an investor at Slow Ventures, author of Young Money: A Field Guide to Wealth and Purpose in Your Twenties, and creator of the popular Young Money Substack newsletter. After graduating during the pandemic, Jack turned an interest in investing into a thriving online platform that led to a book deal with Penguin and a career in venture capital. In this episode, he shares lessons from winning—and losing—money in the stock market, building an audience from scratch, and why creating content can unlock opportunities far beyond direct income.

On this episode we talk about:

  • Jack's early investing journey, including turning $6,000 into $400,000—and the lessons that came with it

  • Why losing money early can make you a smarter long-term investor

  • How starting a Substack newsletter led to a book deal and a career in venture capital

  • The power of building an audience through authentic content and social media

  • Why content creation has become a competitive advantage in venture capital

Top 3 Takeaways

  1. Experience is the best financial teacher. Making mistakes early in your investing journey helps build the judgment needed to make smarter decisions later in life.

  2. Build your own platform instead of waiting for permission. Jack created his own newsletter after being turned down by media companies, which ultimately opened bigger doors than a traditional writing job.

  3. Content creates opportunities beyond revenue. A strong online presence can attract investors, founders, employers, and business opportunities that far outweigh the direct income from publishing.

Notable Quotes

  • "I actually think everybody should lose money at some point, so you know how it feels."

  • "Why not build my own email list and keep the upside and optionality?"

  • "Humor is really good top of funnel—as long as there's something deeper underneath it."

Connect with Jack Raines:

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