Simple Holdings is the company I’ve spent fourteen years building — quietly, deliberately, always for the same people. The plumber. The landscaper. The shopkeep. The builder. The 36.3 million operators running businesses too small for Wall Street to see.
And too important for America to lose.
36.3 million small businesses. Ninety-nine-point-nine percent of every company in America. Nearly half of every private-sector paycheck. Everyone else — the hyperscalers, the giants, the headlines — is a subset. We invest accordingly.
For forty years the Fortune 500 hoarded the leverage — the software, the analytics, the bench of consultants. The age of A.I. ends that. We build and back the tools, services, and capital that put the same leverage in the hands of the family-run HVAC shop and the twelve-seat diner.
We compound. We hold. We operate. We don’t race, we don’t hype, we don’t chase rounds we don’t need. Fourteen years of boring, deliberate, durable ownership — and the thesis has only sharpened. We intend to keep going quietly for fourteen more.
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. We bet on the people first — then the market, then the model, then the numbers. In that order. Always.
You don’t have to sell to get paid. We believe in liquidity without losing control — the discipline of taking chips off the table while keeping the table. It’s the reason both of my books exist. It’s the reason the operators in this house teach it to their own teams. And it’s the reason Simple Holdings will still be compounding long after the next cycle is forgotten.
The operating system, capital, and credentialing network for the small businesses ready to graduate from hustle to holding.
The portfolio for the trades — acquiring, operating, and compounding the home service and real estate businesses that keep America running.
small businesses. One goal — help them not just survive the age of A.I., but thrive in it.
We believe the next American economy will be written by the same people who wrote the last one — the plumber, the landscaper, the bookkeeper, the shopkeep, the operator of the twelve-seat diner on Route 6.
But this time, they’ll have tools the Fortune 500 used to hoard. Our job is to put those tools in their hands — through capital, software, services, and the quiet discipline of long-term ownership.
We invest to create jobs. We operate to prove the model. And we show up — again and again — for the 36.3 million businesses that keep this country on its feet.
Three companies built and sold in four years. No outside capital. No rounds. Then, with the third exit closed, Simple Holdings was founded — to hold, rather than repeat, the cycle.
Third bootstrapped exit closes. Simple Holdings is formed in Connecticut — built to hold, rather than repeat, the cycle.
Exit III · Chapter OneThree years spent in the dirt — building, testing, and launching early-stage companies from the ground up.
Accelerator IThe home services & real estate portfolio is formalized — an early bet on the unsexy businesses that quietly power daily life.
Portfolio ISecond accelerator launched in partnership with IBM — the first of its kind in the state, years ahead of the curve.
IBM · Accelerator IIThe B2B services & SaaS portfolio is founded — infrastructure and capital for the operators of Main Street.
Portfolio IIOperator first. Investor second. Always a builder.
“I started at nine with a lemonade stand. The rules never changed — just the scale.”
Chris Sacchinelli started his first business at nine years old, running a lemonade stand on a street corner in Connecticut. The lesson has never changed: keep it simple, show up, and own what you build.
Between 2008 and 2012, he bootstrapped and exited three companies in four years — the first at six figures, the second at seven, the third at eight. None took outside capital. None ran a round. With the third exit closed, he set up Simple Holdings — to hold, rather than repeat, the cycle.
In the fourteen years since, he has launched two accelerators — including Connecticut’s first A.I. accelerator, in partnership with IBM — and built two operating portfolios held under the Simple Holdings roof: Blue Collar Capital for home services & real estate, and Bootstrapper Capital for B2B services & SaaS.
Today he writes OWNABLE and Exit with Ownership. He hosts the Bootstrapping to Billions podcast. He publishes a weekly newsletter read by fifty thousand operators. And he spends most of his time doing what he’s always done — operating the companies he holds.
He works from Connecticut, plays the long game, and runs Simple Holdings on a single rule: quiet control. Compound ownership. Don’t race. Don’t hype. Build. Hold. Operate. Repeat.
Liquidity Without Losing Control.
A business anyone would buy, is likely one you’ll never want to sell.
Get the book →
Put more profit in your pocket.
You don’t have to sell the business to get paid by it.
Get the book →A weekly letter on building, holding, and compounding ownership. Read by fifty thousand operators.
simple.beehiiv.com →Long-form thinking, teardowns, and operator interviews. Subscribed to by seventy thousand people and counting.
youtube.com/@bootstrappercap →A million listens and counting on the show where we talk to the operators behind the businesses you actually rely on.
Listen to the Podcast →Join a local Bootstrapper.ai chapter. Build the ProfitFlows that turn a grinder’s business into a delegated, transferable, capital-ready asset — one that runs without you. Delegate to humans. Delegate to A.I. Keep the ownership. Compound for decades.
We deploy capital into durable, transferable, long-term equity — Main Street operators built for decades of cash flow, not quarters of growth. If you’re a family office, operator-LP, or fellow long-term investor, there’s a seat at the table.
Whichever door you take — we’ll see you inside.