Bobby Castro built a fintech company from scratch — no investors, no outside capital — and sold it three times: $250M, $600M, then $1 billion.

And when that final wire hit? Nothing. No fireworks.

In the first-ever guest episode of I'm Rich. Now What?, Bobby gets real with Tim and Mark about what actually happens after the big exit — the disappointment, the near-bankruptcy five years before the billion, the missed moments with his kids, and why he walked away at the top to build something he calls a 100-year legacy plan.

In this episode: why the exit fell flat, the "nonrefundable minutes" framework, when to sell, raising kids around money without ruining them, and why transparency is the whole game.

Bobby Castro is a fintech exit veteran ($1.85B+), real estate investor ($800M portfolio), co-founder of R360, and author of Outsider.

In this episode, Mark and Tim dive deep into one of the most important yet overlooked conversations in entrepreneurship: who do you share your wins with?

As commercial real estate recovers and major deals come to fruition, they discuss the power of celebrating your successes—whether that's a 7-figure exit, a business breakthrough, or sharing something with your kids.

Learn how to navigate the delicate balance of sharing wins without alienating those around you, how to identify the right people to celebrate with (spoiler: it's those who energize you, not drain you), and why it's crucial to involve your family in these conversations.

They also explore how talking openly about money wins—and failures—with your spouse and kids builds financial literacy and teaches the next generation that success is a journey of wins and losses. Tune in to discover how celebrating the right way can strengthen your relationships and keep you motivated for the next big opportunity.

Tell us your wins!
@timbratz or @markevansdm on Instagram

There's a point every entrepreneur hits where more stuff stops feeling like more. More watches, more cars, more things — and yet something's still missing. In this episode, Mark and Tim talk about what actually moves the needle when you've already built the wealth: experiences. Specifically, the ones you take with the people you love before it's too late. Mark shares how he spontaneously flew his father-in-law to the Masters — and why waiting even one more year could have meant missing it forever. If you've been putting off that trip, this episode is your sign.