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Jack Raines

Author and writer, Young Money newsletter, Young Money

Search every verified Jack Raines interview, podcast appearance, and on-the-record quote — each transcript cross-checked by AI and human review to confirm speaker identity. Jack Raines, a writer, investor at Slow Ventures, and author of the book *Young Money: A Field Guide to Wealth and Purpose in Your 20s*, has recently launched a weekly show in the Prof G universe. On the show, he analyzes major stories in technology and finance, discussing their implications for personal life and finances. Recent episodes have covered the surveillance economy, including AI glasses and data collection, with a conversation about privacy tradeoffs featuring writer Kyla Scanlon, and Meta’s free AI assistant Muse, where he discussed its potential impact on businesses that rely on customer inertia and the concept of an "annoyance economy." In various podcast appearances, Raines has discussed themes from his book, including career decisions, risk-taking, and financial behavior in one's twenties. He has spoken about his experience turning $6,000 into $400,000 trading SPAC warrants during the 2021 bubble, subsequently losing a significant portion, and has advocated for focusing on career earnings potential over savings rates early in life. He has also commented on social media, describing it as a "massive net negative" for society while crediting Twitter for professional connections, and has discussed the balance between adventure and ambition in young adulthood.

Recent appearances

  • You’re Being Recorded More Than You Think

    October 07, 2026 · 📺 The Prof G Pod – Scott Galloway

    A new show in the Prof G universe by writer and investor Jack Raines! Each week, Jack takes a big story in tech or money and asks what it means for your life and your wallet. Jack Raines explores the surveillance economy, from AI glasses and viral videos to police camera networks. What happens when someone else trades away your privacy – and who benefits when everyday life becomes content and data? Writer and economic commentator Kyla Scanlon joins him to discuss the tradeoffs between privacy, convenience, and safety, and whether AI is solving the problems people actually need help with. Ha…

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  • Meta’s Muse AI Agent Cost $0. What’s the Catch?

    September 30, 2026 · 📺 The Prof G Pod – Scott Galloway

    A new show in the Prof G universe by writer and investor Jack Raines! Each week, Jack takes a big story in tech or money and asks what it means for your life and your wallet. Meta’s new AI assistant, Muse, promises to do more than answer questions. It can shop, handle tedious tasks, and potentially find money you didn’t know you were owed. Jack looks at why Meta is giving it away, what happens to businesses that profit from customer inertia, and whether AI agents could put a dent in the “annoyance economy.” Plus, investor JC Bahr-de Stefano shares what happened when he let an AI agent try to…

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  • He Spent His 20s Exploiting Optionality. He's Doubling Down. | Jack Raines on Knowing When to Commit

    September 30, 2026 · 📺 Epsilon Theory and Cultish Creative

    Jack Raines, author of Young Money and investor at Slow Ventures, joins Matt Zeigler on The Intentional Investor to discuss money, career decisions, and building a meaningful life in your 20s. From making and losing money in the SPAC bubble to leaving his job to travel the world, Jack explores behavioral finance, the opportunity cost of time, and how social media shapes our ideas of success. They also discuss his path from South Georgia to Columbia Business School, the history teacher who changed how he sees human behavior, and why keeping your options open eventually has to give way to choosi…

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  • He Lost $157,000 in 3 Minutes | Jack Raines on the Lesson Winning Never Taught Him

    September 23, 2026 · 📺 Excess Returns

    Jack Raines turned $6,000 into roughly $400,000 trading SPACs, then lost $157,000 in three minutes after taking a very different bet. The author of Young Money joins Matt Zeigler to discuss what that experience taught him about investing risk, the urge to chase more, and the time a growing portfolio can cost you. The conversation follows Jack Raines from SPAC warrants and market narratives to a broader question: how do you allocate money, time, and risk to build a life you actually want? They explore the limits of a trading edge, why cheap stocks can get cheaper, and how debt, career choices,…

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  • time is worth more than money with @Jack_Raines | Ep 79

    September 20, 2026 · 📺 in the trenches by fomo

    In this episode of in the trenches, Jason sits down with Jack Raines, author of "Young Money: A Field Guide to Wealth and Purpose in Your 20s," to talk about the real trade-off underlying every financial decision: time versus money. They discuss his "oh shit" moment on a turbulent flight that reframed how he thinks about mortality, why he quit a stable path to spend a year hostel-hopping through Europe and Latin America, how he turned $6K into $400K trading SPAC warrants, and why he thinks optimizing purely for net worth is one of the biggest traps a 20-something can fall into. Get a front…

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  • Rethinking Money, Time, and What Your Twenties Are For with Jack Raines

    September 11, 2026 · 📺 Justin Castelli

    In this episode of AlignedLife, I sit down with Jack Raines — venture capitalist, Substack writer, and author of the new book Young Money — to talk about what money actually means once you stop treating it as a scoreboard. Jack grew up around entrepreneurial parents and grandparents, which shaped his view of money as fungible rather than scarce. He shares the story of the trip his grandmother took him on to Tanzania at age 11, and the lesson she passed down that money is only worth what you eventually spend it on. We get into why he treated his early twenties as a season for building experien…

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

    September 09, 2026 · 📺 The Rundown

    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 stil…

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  • He Turned $6,000 Into $400,000 Before Turning 24 - Jack Raines

    September 03, 2026 · 📺 Paul Ollinger

    In this episode of Reasonably Happy, I sit down with Jack Raines, writer and investor at Slow Ventures, creator of the Young Money newsletter, which reaches over 60,000 ambitious young professionals, and author of the new book Young Money: A Field Guide to Wealth and Purpose in Your 20s. Jack lays out how he turned $6,000 into $400,000 trading SPACs during the pandemic bubble, lost $150,000 in a single day, and quit his corporate job for a one-way ticket to Barcelona before landing at Slow Ventures on the strength of a personal brand he built from scratch. We cover growing up in Tifton, Georgi…

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  • Jack Raines: How to Avoid Wasting Your 20s l Trailblazers Podcast Episode 49

    August 28, 2026 · 📺 Trailblazers with Erica Wenger

    In this episode, we sit down with Jack Raines, investor at Slow Ventures and author of Young Money, a book about navigating the career, money, and life decisions that define your 20s. We discuss how to avoid wasting your 20s, why you should spend more money while you're young, how to balance ambition with adventure, how to know when you're on the wrong career path, and why building a personal brand without real substance can become a career liability. If you're interested in careers, money, investing, entrepreneurship, venture capital, personal branding, AI, or making better decisions in you…

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  • Gen Z Investor: The AI economy is TRAPPING young investors!

    August 26, 2026 · 📺 Phil Rosen

    Jack Raines is the author of "Young Money: A Field Guide to Wealth and Purpose in Your Twenties." He joins Phil Rosen on Full Signal to discuss why young people should spend more and invest less, the pull of sports betting and prediction markets on Gen Z, how he turned $6,000 into $400,000 trading SPACs, and why housing costs sit underneath most of this generation's anxiety. This episode is sponsored by Harbor Capital Advisors: https://www.harborcapital.com/suite/a... Like this episode? Podcast subscribers got it 3 hours before YouTube: 🍎 Apple: https://podcasts.apple.com/us/podcast... 🟢 Sp…

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  • The 75% Rule: When to Actually Bet Your Career on Passion | Jack Raines

    August 23, 2026 · 📺 Matt Ebert

    Jack Raines - writer, VC investor, and author of Young Money - shares the biggest lesson of his 20s: he's deeply anti "follow your passion" as a career. His argument is sharper than the usual warning - passion probably won't pay, and even if it does, you'll likely stop loving it once it has to put food on the table. He tells the story of taking his "dream" media job building Sherwood News at Robinhood, realizing the structured W2 grind killed the thing he loved about writing, and course-correcting fast into venture capital by leveraging the platform he'd built. Plus: why money matters more as…

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  • Episode 187: Jack Raines Trolls LinkedIn and Ends Up with a Book Deal

    August 21, 2026 · 📺 MarketectureTV

    Ari Paparo and guest co-host Paul Knegten sit down with Jack Raines, author of Young Money, to discuss how viral LinkedIn posts, humor, and attention-driven marketing helped him build a 61,000-subscriber newsletter, land a book deal, and create a personal brand. The episode also covers OpenAI, WPP, Walmart Connect, Taboola, Google’s AI advertising strategy, LiveRamp, and Higgsfield. Takeaways: Jack Raines turned provocative LinkedIn posts into a subscriber acquisition engine for his newsletter. Authentic personality and calculated controversy can generate attention, but the product still need…

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Verified interview transcripts

Notable quotes

“The best benefit of targeted advertising isn't just seeing better recommendations, but we all benefit from a lot of free or cheaper things that would have cost us much more money otherwise. Take Uber for example. Yes, Uber prices now seem a bit expensive. I've also noticed the price increases. It's likely that Uber's advertising business keeps prices lower than they would be without it. Uber makes two billion dollars”

“I think social media is massive net negative society because it's just an information overload that makes people feel bad about where they are in life. That being said, Twitter as a platform for just like connecting with interesting people has been phenomenal. I'll give you an example right now. I tweeted I've been using a lot of the AI coding assistant things and like comping them against each other. Grockbot, I don”

“Groundwork Collaborative estimates that the accumulated cost of the annoyance economy is around $165 billion a year in lost time and wasted money for American families. This is everything from being stuck on hold to spending time clicking through endless series of pages to cancel subscription to screening spam calls or trying to change a flight. Agents are really good at doing all this stuff and they don't care about”

“The reason that Anthropic, OpenAI, and these other AI labs tend to have stricter usage limits for their users is they can't afford to just give away all this compute. Something that Meta has that OpenAI and Anthropic don't have is Meta is a massive advertising business. In the last quarter alone, Meta did $59 billion in advertising revenue. The entire rest of the business did $1.5 billion. Meta is an advertising comp”

“I think young people should be very very very focused on career earnings potential but less focused on savings rate when they're young. My reason for that is making more money solves way more problems than better budgeting does if you're coming off a low income base. There's obviously you can run into lifestyle inflation and people like I know plenty of people in New York making very very good money. They're basicall”

“I view money as a just a like numerical value of things that you either can and will pay for now or you can and will pay for at some point in the future, right? So, it's easy to hyper obsess over what's my income today, what's my net worth today. But money simply put to me is it's just this medium of exchange for literally anything right now. You could also say that part of that is having money in the bank account pr”

The summary and quote tags on this profile are produced with AI assistance from verified, first-person interview transcripts, then checked by our team to confirm the speaker's identity and the accuracy of every quote. See how we verify →