Managing Tech Millions

How Much Time Does It Actually Take to Run a Family Office? Around 2017 and 2018, my Family Office got complicated, and I was buried in it. I was sorting transactions, chasing statements and reconciling accounts late at night. It felt like a second job, and I assumed that was just the price of running my own. It wasn’t. Most people picture a Family Office taking a huge chunk of their year. The bet...

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 ho...

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 q...

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...

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 busin...

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 operatin...

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...

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 sh...

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 th...

If you're sitting on $1 to $30 million, the wealth management industry has left you stranded. You've outgrown basic personal finance advice. You're not rich enough for the family offices built for the ultra-wealthy. So you end up managing millions the way most people manage thousands. I lived in that gap. Former tech CIO, concentrated equity, no playbook. Today I run a $7 million portf...

Most advisors hand you the same plan. Accumulate for 30 years, then withdraw 4% a year and hope the math holds. I ran that plan through real numbers in this video: the taxes, the sequence risk, the principal you liquidate every year to pay yourself. It's a water tank you drain while praying it rains again. Ultra-wealthy families operate differently. I've sat on both sides of the table, as...

In 2012 I had millions in the bank and no income strategy. Every advisor told me the same thing: 60/40 portfolio, 4% rule, you're set for life. Then I went and read the research behind that rule. It comes from a 1994 study, and what it leaves out is the thing that can end a retirement in the first three years. So I spent the next decade studying how ultra-wealthy families actually pay for thei...

In 2012 my company IPO'd and I watched my net worth go up $3 million in a matter of minutes. A few days later I sat down with a Morgan Stanley advisor expecting a playbook. I got 30 minutes of the same recommendation he gives someone with $100K in a 401(k): 90% stocks and bonds, 10% cash. He wasn't a bad advisor. He was giving me the only thing the industry is built to give someone at my l...

You Don't Need $100M to Run a Family Office If your net worth sits between one and thirty million, you already have investments. What you're missing is the system that grows them, protects them, and passes them down. That gap separates owning a portfolio from running a family office. The wealthiest families in the world run their money like a business. Every family office operates on the s...

Most first-generation wealth doesn't survive the handoff. The investments were usually fine. The problem is that everything holding it together lives in your head. The strategy, the reasoning, the relationships, the plan for what happens next. In tech we call that a single point of failure. Right now, that's you. The Rockefellers solved this in 1882, and their family office still runs 140...

The moment your wealth becomes worth protecting is the exact moment the financial industry stops serving you. Too complex for retail advice. Too small for the family office built for hundred-million-dollar fortunes. Welcome to the service desert—where defending everything you've built falls to one person. You. And here's what nobody warns you about: your wealth isn't facing one threat....

Most retirement advice tells you to survive market swings with more diversification, more bonds, more cash on the sidelines. I'm going to show you why that entire premise is backwards. Here's the uncomfortable truth: a 20% drop doesn't hurt you. Being forced to sell into that drop does. And the traditional retirement model all but guarantees that moment arrives. There's even a name...

If you have between one and thirty million dollars, you've probably done what almost everyone does: handed it to an advisor, paid the fee, and hoped the money outlasts you. That's the 99%. And it's not your fault—no one ever handed you the playbook. The ultra-wealthy don't hope. For over a century they've used a specific structure to run their wealth like a business built to ou...

Most first-generation wealth builders make the same move: they cross the million-dollar threshold and immediately ask "where should I invest?" That question is the trap. And it's costing you more than you realize. In this conversation, I sit down with Marco Quevedo—my friend from our UCSD days, a Wharton MBA, and now the Chief Investment Officer of a nine-figure family office. Marco ha...

I Ranked Every Income Investment, Best to Worst — One Popular Pick Got an F Most income advice gets one thing backwards: it ranks investments as if there's a single right answer for everyone. There isn't. So I did something different. I took every income vehicle worth knowing — annuities, covered call ETFs, private credit, REITs, syndications, BDCs, muni bonds, the ones your advisor pitche...

The Truth About Covered Call ETFs Nobody Tells You Covered call ETFs might be the most blindly bought income product on the market right now. And almost everyone picks the same way: they chase the biggest yield number on the website. Here's what that number won't tell you. The yield is what you receive . It says nothing about what you actually keep . I learned this the hard way when I star...

You're Too Big for the App—and Too Small for the Family Office If your net worth sits somewhere between one and thirty million dollars, you're stuck in a place nobody built for you. Too big for the retail app on your phone. Too small for the single family office running things for the ultra-wealthy. So you default to the only option anyone ever handed you: give it all to an advisor, pay th...

You Don't Need a Better Advisor. You Need a Better Structure. As your wealth grows — one million to two, two to five — you outgrow your financial advisor. So you go hunting for a unicorn: the one advisor who'll finally get it. I did the same thing after my first IPO watched my net worth jump to $3.3 million. Every firm came back with the same cookie-cutter pitch and the same 1% fee. Here&#...

Most people think they're in charge of their money. They're not. If you have a financial advisor telling you what to buy, when to worry, and what your goals should be — and you're nodding along — you're not running your wealth. You're an employee in a business you own. I'm not saying fire your advisor. I'm saying something different. There's a specific seat you shou...

SpaceX is about to mint 160 new millionaires — and most of them will get this wrong You think the big decisions come after the money hits. You're wrong — and that misunderstanding is what costs first-generation wealth builders the most. A tweet stopped me cold this week. Roughly 160 people in Austin are about to clear $100 million from the upcoming SpaceX IPO. Twelve will clear a billion. I cl...