Wrote the playbook I wish existed 10 years ago.
"Running a Family Office Under $100M"
What actually makes sense at $5M, $20M, $50M. When to DIY vs. hire. The real costs nobody talks about.
Free to read:
https://t.co/BwK3ppMKSn
Every tool for hedging a concentrated stake needs one thing first: a ticker. Exchange funds, collars, prepaid forwards. A private, pre-exit stake can't use any of them. The liquid side is the only lever left before exit.
https://t.co/ZX8GQi6FrM
Not investment advice.
Ten stocks are about 44% of the S&P 500, the highest share on record. A software founder holding the index is buying more of the same bet their business already rides. The dangerous concentration is the safe money.
https://t.co/iCVZ4TtLzy
Not investment advice.
Can you run your own money with AI now?
Backwards. It's worst at the investment calls, best at making the people who make them cheap enough to hire below $100M.
https://t.co/87CnYVixhg
In 2013, Nassim Taleb gave a 53-min Stanford masterclass on why chaos makes some businesses stronger.
His ideas:
- The coffee cup that survives 4 million hits
- Why helicopter engineers ride their own machines
- The country where nobody knows the president
12 lessons on risk:
UBS just published their 2025 billionaire survey. One section covers how they plan to allocate in 2026.
The short version: they're not getting defensive.
49% plan to increase direct private equity exposure. 43% are adding to public equities and hedge funds. Emerging markets? 42% increasing, only 2% reducing.
Meanwhile, just 19% are adding to cash positions. Commodities barely register.
What I find interesting isn't the specific allocations - it's the confidence. Geopolitical mess, inflation still sticky in places, plenty of reasons to sit tight. But the people with the most to lose aren't pulling back.
Whether that's conviction or just having enough cushion to ride out whatever comes next - probably both.
Full data from UBS Billionaire Survey 2025 if you want to dig in.
Tax efficiency isn't about paying zero.
It's about not paying more than you should.
Founders often over-optimize. Convoluted structures. Aggressive positions. Audit risk.
The goal is appropriate tax efficiency, not minimum tax at any cost.
Building a library of frameworks for founders managing wealth.
Not theory. Not product pitches. Just what actually works in the $5M-$100M range.
Playbooks. Weekly signals. Case studies.
All free at https://t.co/OMsfqUz8iL
The best advice he got: treat year one as recovery, not optimization.
Don't make big decisions. Don't chase new ventures. Don't try to prove anything.
Rest. Observe. Let the dust settle.
More on navigating this transition: https://t.co/yXmvEOj303
The "what now?" question is relentless.
You thought the exit would answer it. It doesn't.
It just gives you resources to pursue whatever answer you find.
Most founders spend year one avoiding the question. Year two forced to face it.
The most underrated skill in wealth management: saying no.
No to deals. No to complexity. No to advice you didn't ask for.
Every yes has a cost. Time. Attention. Capital.
The best portfolios are defined as much by what's not in them as what is.
I've met billionaires who are miserable and decamillionaires who are free.
The difference isn't the number.
It's whether they designed the life first and let the money serve it — or let the money dictate the life.
Sequence matters.
The founders who build again usually wait 2-3 years.
Not because they're slow. Because they need to reset.
The ones who jump immediately often build the same company with the same problems.
Space creates clarity. Rushing creates repetition.
Every asset has a job in your portfolio.
Equities: growth Bonds: stability and income Real estate: inflation hedge and cash flow Cash: optionality Alternatives: uncorrelated returns
If you can't articulate the job, question why you own it.
Unpopular opinion: Founders should avoid fund-of-funds.
Layer of fees on layer of fees. Diversification you could achieve yourself. Complexity that obscures rather than illuminates.
The pitch sounds good. The math rarely works.
If you want alternatives, go direct or don't go.