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AlignedLife with Justin Castelli

AlignedLife with Justin Castelli

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

Sep 11, 2026 · 49m

Coming soon to iPhone. Already have it? “Listen in Starcast” takes you straight there.

About this episode

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…