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

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 experience and social capital rather than chasing a paycheck — including the year he spent backpacking Europe and Latin America before business school — and why he thinks time, not money, is the one truly finite currency we have. We also dig into the tension between planning for the future and staying present, why he pushes back on the advice to obsess over savings rate in your twenties, and how intuition — backed by a disciplined information diet — has guided his biggest decisions, from career pivots to where he lives to how he dates. Toward the end, Jack shares a rule of thumb about planning your asset location for the version of you at 40, not 65, plus a half-joking pitch for a "degenerate account" every young investor secretly needs. If you're trying to figure out how money and time actually fit together at different stages of life, this conversation is for you. Jack's book, Young Money, is out now, and his newsletter of the same name lives at youngmoney.co on Substack. Find him on X, LinkedIn, and Instagram — search his name and look for the cowboy hat. 🔗 Young Money (the book): www.amazon.com/Young-Money-Wealth-Purpose-Twenties/dp/B0FZS5PL15 📩 Jack's newsletter: www.youngmoney.co