After my company went public, 90% of my net worth was sitting in one stock. Then came the lockup. I couldn’t sell a single share, so I just watched. Every day, almost everything my family had moved up and down with one ticker.

Most people in that spot start with one question: should I sell? It’s the wrong first question. It pushes you into all or nothing: sell everything, or hold everything and hope. The better question is what you actually want that money to do.

In this episode, I’ll walk you through the four steps I used to unwind my position over several years. You’ll learn the two jobs your stock can do and why it’s so hard to see which one it’s doing right now. You’ll set two goals that decide how much you sell and how much you keep on purpose. You’ll see how to keep taxes from running the plan. And you’ll get a selling rhythm you can repeat every quarter without guessing at the price.

I’ll also tell you what a private bank told me to do with that stock right after the IPO, and why I didn’t do it.

By the end, you’ll know how to think through your own concentrated position, so the stock that got you here doesn’t decide whether you stay here.

For years, I asked one question about every investment: will this grow my wealth? Friends brought me public companies. Old coworkers brought me startups. Cold emails showed up with decks attached. I spent evenings and weekends running numbers, and I ended up with a portfolio of yeses that never worked together.

Wealthy families ask something different: does this fit what we’re building? That one question lets them say no to almost every investment that crosses their desk, and they don’t feel like they’re missing out.

I’ll walk you through the three filters they run before an investment gets a single dollar. One defines what your portfolio is for. One asks whether there’s an open seat. The third turns due diligence upside down, and it’s where Marco, a family office CIO I interviewed, gives the advice I use most.

Changing the question gave me back my time and took away a lot of the anxiety. It even saved a few friendships, and I’ll tell you how.

By the end, you’ll know which question you reach for first, and which filter would have stopped your last investment.

Is a Micro Family Office Worth It at $5 Million?

When I passed $5 million in net worth, I had a house, private equity investments, a portfolio I was starting to build, and an estate plan that wasn’t finished. I was paying a lot in taxes every year. None of it was working together. I had a portfolio, but I wasn’t the CEO of it.

Most people I talk to at this level ask the same question: can I afford a family office? That’s the wrong question. And this was never about firing your financial advisor.

I’ll walk you through the three questions I use to decide whether a Micro Family Office is worth it at $5M. One is about the pieces you already have. One is about what happens when the paycheck stops. The third is the one nobody puts on a spreadsheet.

I’ll be honest with you, too. For some people the answer is yes. For some it’s “not yet.” And for some it’s a clear no, and I’ll tell you who.

By the end, you’ll know which column you’re in, and what your wealth needs from you next.