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.

At five million dollars, everyone tells you you’ve won. That you can rest easy. That’s not what it felt like to me.

When my company went public in 2012, I had multiple seven figures overnight, almost all of it in one stock. On paper I’d made it. In practice, I’d walked into a new game, and the rules didn’t come printed on the box.

At this level, your wealth stops being a number. It becomes a business. And for most people, nobody is running it.

I walk through the six rules that change at five million: concentration, taxes, protection, lifestyle, succession, and your kids. For each one, you get a clear test to know whether you’ve handled it. Plus the backyard habit an insurance broker flagged as our single biggest risk.

Then there’s a seventh rule. It has nothing to do with money, and it cost me the most. I’ll share what someone close to me said when I was struggling with it. It’s the reason this channel exists.

By the end, you’ll know which rule is already your problem, and which one to tackle first.

Too Wealthy for Generic Advice. Too Small for a Family Office.

Building wealth is one skill. Managing it across investments, taxes, legal structures, and generations is an entirely different discipline. Yet if your net worth sits between mass-market advice and a traditional family office, the financial industry often leaves you with scattered accounts, generic recommendations, and no real operating system.

I know that gap because I lived it. After years of studying how the world’s wealthiest families preserve and compound capital, I built a lean version for my own family: a Micro Family Office. It changed the way I thought about wealth—not as a portfolio to monitor, but as a business to architect, operate, and eventually pass on.

The surprising part isn’t that this model works for billionaires. It’s how much of it can be right-sized for first-generation wealth builders without the staff, overhead, or complexity of a traditional family office.

In this video, I break down the service desert, the shift happening now, and the framework behind a Micro Family Office. Watch if you’ve outgrown DIY wealth management and want to understand what it takes to become the CEO of your own wealth.

You're great at growing your wealth. You earned the equity, maybe rode an IPO, and watched the number climb. Now ask yourself how you manage it. If you're where I was, the answer is spreadsheets, accounts scattered everywhere, and a few investments with no real purpose behind them.

That changed for me after my first IPO, in a conversation with my friend Marco. He's the chief investment officer of a single family office worth billions, and talking with him changed how I saw my own money.

Family offices go back much further than you'd guess. The wealthiest families in history have used them to run their money as a business and carry it across generations. But the industry comes in tiers, and one group got left out. If you hold between $1M and $30M, that's you.

In this video I walk through where you fit, what the job involves, and how I scaled the family office model down into something one household can run.

It isn't for everyone. By the end, you'll know whether you're ready to be the CEO of your family's wealth.

Let's keep building.

Most people think a family office only makes sense once you have $100 million. The right structure makes it work at $1 million.

I spent 10 years studying how the ultra-wealthy manage their money, then built my own family office from scratch. Every family office, whether it manages $50 million or $5 billion, runs on the same 7 components. Same principles, scaled execution.

I break down all 7 and show how each one scales for someone with $1 million to $30 million. You'll see why most portfolios look like a junk drawer once you map them out, which component people overlook even though it might matter most, and the one piece you can never delegate, no matter how good your team is.

I'll also share what my own family office costs to run each year, and why that's the wrong number to focus on.

If you've built real wealth but still manage it like a side project, you'll leave knowing what a family office looks like at your level and how to start running your wealth like a business. Let's keep building.

What I'd Do Differently With My First $500,000

Between 2013 and 2018 I deployed $530,000 across nine investments while I was still working full time in tech. It worked. That capital paid me real income from the first year, and it became the foundation of the portfolio that now generates around $200,000 a year.

It also took far more work than it needed to.

I've put millions to work since then, and I've watched which decisions hold up across cycles and which ones only worked once. Standing at that same crossroads today, with the same $500,000 and the same goal, I'd build it a completely different way: fewer investments, fewer operators, and a lot less of my own time.

In this video I walk through the original deployment in detail, what each piece returned, and the five principles I'd follow instead if I were starting tomorrow. The shift that drives all five runs against everything my tech career taught me about what makes something valuable.

If you're sitting on capital you want to turn into income, this is the framework I wish I'd had in 2013.