Madvertising by AdQuick — Advertising, Marketing & Ad Tech Podcast · AdQuick

Jack Raines: internet entrepreneurship, gen z, personal finance and more | E59

·40 min·2 clips

The hosts push Jack on LinkedIn’s ‘cringe’ culture, and he calls it the most valuable social platform on the planet.

1. Madvertising by AdQuick features Jack Raines talking about internet entrepreneurship, Gen Z, personal finance, and LinkedIn. 2. Host Adam and guest Jack Raines matter because Jack writes Young Money and Adam frames the marketing angle. 3. The episode asks how a finance blogger built an audience, monetized attention, and made a career move into venture capital. 4. Jack says he is moving from New York to San Francisco for three months, then back to New York, then out to SF for at least a year. 5. He says a partner in San Francisco told him, “you should move out here and work for me for a little bit,” after he applied for a job in New York. 6. Jack explains that he used to work in corporate finance, hated it, quit, traveled before business school, and then helped run the finance meme page Liquidity. 7. He says Liquidity had about 700,000 followers across Instagram and Twitter and a newsletter with about 100,000 readers. 8. Jack says the newsletter job paid him $500 a week while he was hostel-hopping Spain. 9. He says watching newsletter ads showed him how directly attention and distribution could be monetized. 10. He says he thought that reaching 50,000 subscribers could support “a couple hundred thousand dollars a year” from weekly ads. 11. Jack describes how he used Twitter replies and viral posts to send people to Young Money, and he says a tweet with 1,000 likes could bring in about 300 newsletter subscribers. 12. He says Elon Musk buying Twitter made newsletter growth harder and that Twitter was more fun “three years ago.” 13. Jack says he copied Tim Urban and Morgan Housel, then started drawing stick-figure thumbnails in Fire Alpaca for his pieces. 14. He says AI thumbnails all look like “the same type of good,” while rough cartoons stand out because they feel human. 15. Jack argues that people connect more with imperfect human-made work than with polished machine output, even when the machine is technically strong. 16. He says a similar logic applies to Christopher Nolan crashing a real 747 in Tenet instead of relying only on CGI. 17. On money in your 20s, Jack says he prefers a mix of grinding and living, especially if someone is building a career or taking a low-paid apprenticeship. 18. He says saving aggressively for money you will spend at 70 or 80 is a poor use of cash when you are 23 or 24. 19. The episode has a conversational, high-energy interview style with long back-and-forth riffs and personal examples. 20. People interested in media growth, Gen Z behavior, or LinkedIn should listen, while listeners wanting a tightly structured finance lecture may skip it.

As heard by us

A grounded conversation about money, career moves, and the value of early experience.

Jack takes money and career talk in a practical direction, with a clear focus on how early choices can shape the rest of a working life. The conversation moves from blogging and finance to venture capital and personal finance, but it never drifts far from real examples, which…

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Why you'd press play

You want career advice that sounds like a real person, not a template.

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