Tad built Long Angle, a private community of over 8,000 people worth $5 million to $100 million and up. Most of them are first-generation wealth. He sees how this whole class actually handles money, and he shared the real numbers with us.
Here are the parts worth your time.
The bootstrap math nobody talks about
Tad bootstrapped a SaaS company to 100 employees and sold it. No big venture round. His point was simple. Most companies are not VC companies. If your market caps out at a few hundred million, a giant raise just buries you under liquidation preferences. You exit for $60 or $70 million and walk with $3 or $4 million after the pref eats the rest.
A $10 million personal exit puts you in the top 1% of this country. And it is far more reachable than a $150 million exit that nets you the same $10 million after everyone else gets paid. His rule is that the longer you can wait to take money, the better the terms when you finally do.
What people worth $5M to $50M actually buy
The savings rate surprised me. On average his members save about 50% of their post-tax income. Somebody earning $2 million in California keeps a million after tax and still banks half of that.
They do not spend it on cars or houses. Housing runs 10 to 20% of net worth for most of them. The big discretionary bucket is travel.
The stuff people agree on buying is time. A CPA, a nanny, a personal trainer, anyone who hands hours back. The stuff that gets no love is the flex. Ferraris, Rolexes, branded clubs. Most of this group finds it gross. They want the convenience and the service. The logo does nothing for them.
The US wealth gap is wild
To sit in the top 1% in America you need about $12 to $13 million. In France or the UK, $3 million gets you there. The only European country that matches the US is Monaco, which is basically a tax shelter the size of half a borough.
How his community picks managers
This section is gold if you invest as an LP. Here are a few of the filters he uses:
Invest alongside institutions. If the Stanford and Duke endowments are in the fund, someone with real leverage already beat the manager up on fees and diligence. If a fund is chasing doctors and dentists instead, ask why the pros passed.
Skip fund 1 and fund 2. Too much variance, not enough track record. He wants to see cycles.
Watch the GP's own check. When the operator has a quarter of a billion of his own money in an oil and gas fund, he drills carefully.
Hold the line on fees. He passed on a deal where the “80/20 split” turned out to be 80% to the GP. Real number. Real pitch.
Back specialists. The energy guys who grew up in Houston, studied petroleum engineering, and live in the Permian post 40 to 70% IRRs. The generalist dabbling in energy on the side does not.
Where the money is moving now
Here are three areas Tad likes right now:
Co-invests. Getting into names like Anthropic and SpaceX through a fund's overflow allocation, at low fees and low carry, with a higher hit rate than early venture.
Secondaries. Buying out LPs who need liquidity, sometimes at 50 to 70 cents on the dollar in real estate. You skip the J-curve and often get your capital back faster.
Upstream oil and gas. Fracking took most of the guesswork out of the geology. Good operators are seeing sub-year breakevens, closer to six or seven months right now.
The part that hit close to home
We got into boring businesses. The “guys in trucks” world. Med spas, HVAC, plumbing, paving. Tad's honest read is that the roll-up trade has gotten more crowded, and returns that used to look like 6x might compress to 2 or 3x.
He still likes the model. And when I told him paving is our world, he made the point that matters most. Paving is defensible. Hard to compete away with AI. The edge comes down to discipline. You buy well and operate, or you overpay just to collect a management fee.
Give the full episode a listen. Tad is one of the sharpest and most straightforward operators I have had on.
Join us next Tuesday
I am moderating a live panel on investing in debt to build cash flow. The four panelists have raised over $500 million across asset classes in the last five years, a good chunk of it in debt and credit. Chris Larsen, Mathew Owens, Chris Wirthlin, and Patrick Grimes.
July 7th at 7pm EST. All are welcome. Register below and bring your questions.
— Sam Silverman
Silverman Capital
P.S. Planning more of these. If there is a topic you want covered, or you think you belong in one of these seats, reply and tell me. I want to pull future panelists from this community.
