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.

Most successful entrepreneurs plan to leave their kids a life-changing inheritance. The problem? By the time the money arrives, their kids are in their 50s — and the window to actually change their lives has long passed. In this episode, we dig into the psychology of wealth transfer, why giving a "living inheritance" beats waiting until death, and how to raise kids who are actually ready to handle it.

This is about more than inheritance. It's about building a real legacy.

We get into:
- Why most people receive inheritance too late in life
- How giving money too early can help (if done right)
- The balance between teaching and supporting your kids
- Why experiences might matter more than dollars
- How to raise kids who are capable, confident, and financially smart

At the end of the day, this isn't about money. It's about who your kids become.

If you're building wealth and thinking about your family's future, this is a conversation you need to hear.

If this episode helps you, share it with someone who needs it.

You worked for years to build something worth selling. But what happens after the check clears?

Mark Evans DM and Tim Bratz get into one of the most important conversations entrepreneurs aren't having — what to do with your money after a big exit. And the answer might surprise you: the mindset that made you rich could be the exact thing that loses it all.They walk through the psychology of going from wealth builder to wealth preserver, why sitting on your money for 12 months might be the smartest move you ever make, and how to build a simple framework for deploying capital without losing sleep or getting taken advantage of.This one is for anyone building toward an exit — or already planning what comes next

In this episode:
- Why the mindset that builds wealth is different from the one that keeps it
- The 12-month rule after a big exit
- The quarter/quarter/quarter/quarter diversification framework
- Buy for investment, rent for lifestyle
- Why writing fewer, bigger checks beats spreading money thin
- How to define your "opportunity buy box" post-exit
- Why purpose matters as much as capital allocation

What if you've been thinking about retirement all wrong?

Mark Evans DM and Tim Bratz aren't waiting until they're 65 to start living. In this episode they get honest about what retirement actually means for entrepreneurs — and why the people who could stop working tomorrow are usually the last ones who want to.

They're talking bucket lists, memory dividends, and why spending money on experiences with the people you love isn't a luxury, it's an investment. Mark makes a challenge that might just change how you spend your weekend. Tim breaks down how putting real deadlines on your dreams is the only way they actually happen.

This isn't about quitting work. It's about building a life good enough that you're already living it.

In this episode:
- What retirement actually means for high performers
- Why the wealthiest people Mark knows never want to stop working
- How to build a bucket list with real urgency and deadlines
- The ROI of investing in experiences and memories
- Why "someday" is the most expensive word in your vocabulary
- How to start living retired without stopping work

🔔 Share this with someone who's still waiting to start living. Tag us on social and leave us a 5-star review!

You built the business. You closed the deals. You hit the number. But if all of that disappeared tomorrow, who would you be?

Mark Evans DM and Tim Bratz get into one of the most overlooked traps successful entrepreneurs fall into: wrapping your entire identity around what you DO instead of who you ARE. Tim opens up about pivoting away from being "the multifamily guy" after 20 years, winding down his coaching program, and the cognitive dissonance that comes with reinventing yourself at a high level. Mark shares why the people calling you a flip-flopper are the ones stuck — and why evolving your identity isn't weakness, it's the whole game.

But there's a flip side too: you have to intentionally become the person you're trying to be. The mindset, the identity, the self-concept...it has to come before the bank account catches up.

This one will hit different if you're in the middle of a pivot, a sale, or just quietly wondering if the version of you that built this is the same one who should be running it.

🔔 If this hit home, share it with someone in the middle of a pivot. Tag us on social and leave a 5-star review wherever you listen to podcasts!

The podcast is barely 6 episodes old and the trolls are already showing up. In this episode, Mark and Tim address the haters head-on, not to clap back, but to break down why negativity follows success, and what high achievers actually do about it. They cover the crab mentality trap, a powerful three-bucket framework for managing the people in your life, and the one mindset shift that makes criticism roll right off you.

If you've ever let someone else's opinion slow you down, this one's for you. If this episode hit home, do us a favor and hit that like button, it helps more people like you find the show. Subscribe so you never miss an episode, and if you've got a minute, leave us a five star review. It genuinely means the world to us and helps us keep this conversation going.

Got haters in your life, or a story about how you dealt with them? Drop it in the comments — we read every single one. And if you know someone who needs to hear this today, share this episode with them. We'll see you next week on I'm Rich. Now What?