N° 03 · The Thesis
Five beliefs. No exceptions.
What Simple Holdings was built on — and what every decision we make is measured against. Each belief carries a position, a practice, and a number we can be held to.
- 01
The Asset Class
Main Street is the asset class.
36.3 million small businesses. 99.9% of every company in America. Nearly half of every private-sector paycheck. The hyperscalers and the headlines are the subset — not the other way around.
How we apply it
We allocate capital and attention to home services, real estate, and B2B services & SaaS — the businesses that pay their bills with cash, not narrative.
By the number
36.3MU.S. small businesses - 02
The Unlock
A.I. doesn't replace operators. It arms them.
For forty years the Fortune 500 hoarded the leverage — software, analytics, a bench of consultants. The age of A.I. ends that. The HVAC shop and the twelve-seat diner now run on the same rails the giants do.
How we apply it
We build and back the tools, services, and capital that put enterprise-grade leverage in the hands of the family-run operator.
By the number
2016Launched CT's first A.I. accelerator with IBM - 03
The Posture
Quiet control beats loud growth.
We compound. We hold. We operate. We don't race, we don't hype, we don't chase rounds we don't need. Deliberate, durable ownership — and the thesis has only sharpened.
How we apply it
No outside capital. No funds. No raise cycles. Holdings are kept, not flipped, and run on operator cadence — not investor cadence.
By the number
0Outside funding rounds - 04
The Order
The operator comes before the deal.
We only back businesses we'd run ourselves. Every company held under this roof has a person we'd trust with a holiday shift. Capital is easy. Operators are not.
How we apply it
People first, then market, then model, then numbers. If the operator doesn't pass the holiday-shift test, the deal doesn't happen.
By the number
1stFilter we run every deal through - 05
The Payoff
Ownership is the win.
You don't have to sell to get paid. Liquidity without losing control — chips off the table while keeping the table. It's why both books exist. It's why Simple Holdings will still be compounding long after the next cycle is forgotten.
How we apply it
We design for the 5 Exits of Ownership — preserving equity, control, and cash flow at every stage instead of trading them away at the finish line.
By the number
03Bootstrapped exits — equity intact
The thesis, in one line.
Back Main Street operators, arm them with A.I.-grade leverage, hold what works, and treat ownership — not exit — as the win.