We buy, build, and back the businesses that hold Main Street together.
The plumber. The landscaper. The bakery on the corner. The HVAC shop your parents called. Simple Holdings is the quiet operator behind two portfolios built for the 36.3 million small businesses too important to lose.
Who we're for
If you run it, we respect it. We don't chase unicorns. We back the unsexy, profitable shops that show up every day — and the operators behind them.
- Plumbing, HVAC, and electrical
- Landscaping and lawn care
- Bakeries, diners, and shopkeeps
- Cleaning, painting, and handyman
- Bookkeeping and back-office services
- Independent real estate holdings
- Trades succession and quiet roll-ups
- Operator-led B2B services
A note from the founder
"I started at nine with a lemonade stand. The rules haven't changed — just the scale. We buy small businesses to hold them, not to flip them. That's the whole thing."
— Chris Sacchinelli, Founder
We're in the long-term equity business — not the exit business.
Most of finance is built to sell. We're built to hold. Long-term equity means buying simple, profitable businesses and compounding them for decades — not flipping them on a five-year clock. No fund timelines. No forced exits. No outside LPs telling a fifty-year-old plumbing shop to ten-x by Tuesday. Just patient ownership, real cash flow, and operators who get to stay operators.
01 · Hold, don't flip
We measure success in decades held, not multiples returned. The best business is the one we still own in 2050.
02 · Cash flow over story
Profitable on day one. Boring is the feature. We'd rather own a great HVAC shop than a pre-revenue narrative.
03 · Operator-first equity
Founders and operators keep meaningful ownership. Liquidity without losing control — the whole point of the books we wrote.
04 · Compounding, quietly
Reinvest the cash. Add the next shop. Arm the team with AI. Repeat for thirty years. That's the entire playbook.
Blue Collar Capital — home services, trades, and real estate. The businesses that keep the lights on, the lawns cut, and the pipes running.
Two houses. One roof.
Wing I · Blue Collar Capital — Est. 2015
Home services, trades, and real estate. Plumbing, HVAC, landscaping, cleaning, and the independent real estate around them. Boring, profitable, owner-led — the asset class most of Wall Street can't be bothered to touch and most of Main Street can't afford to lose.
Wing II · Bootstrapper Capital — Est. 2020
Bookkeepers, B2B services, and the software the corner shop actually needs. Capital and tools for operators ready to graduate from hustle to holding. This is where the OWNABLE OS, the Bootstrapper.ai platform, the SMB Accelerator, and long-term equity management live.
Why "Simple"
Simplicity isn't a lack of sophistication — it's the result of it. Simple Holdings favors systems over relationships, durable structures over clever ones, and ownership that's meant to last. Simple is the hardest thing to build and the most valuable thing to own.
Why a holding company — and not a fund
A fund has a clock. A vintage year. A forced exit. A continuous capital company has none of those. It can hold a business for as long as the business produces durable cash flow. That structure is what made long-term equity management possible to invent in the first place — and what made the OWNABLE OS the operating system we now teach to other owners.
Where to go next
- Bootstrapper Capital (Wing II) →
The B2B services, software, and methodology wing.
- Chris Sacchinelli, Founder →
The operator behind both wings.
- Long-Term Equity Management →
The discipline Simple Holdings was built on.
- The OWNABLE OS →
The operating system we run in-house first.
Frequently asked questions
What is Simple Holdings?+
Simple Holdings is a Connecticut-based holding company founded in 2012 by Chris Sacchinelli. It buys, builds, and backs the small businesses that hold Main Street together — operated under two wings: Blue Collar Capital (home services, trades, real estate) and Bootstrapper Capital (B2B services, bookkeeping, SaaS).
Is Simple Holdings a private equity fund?+
No. Simple Holdings is a continuous capital company — permanent capital, no fund clock, no outside LPs. We hold to compound, not to flip on a five-year timeline.
What kind of businesses does Simple Holdings buy?+
Boring, profitable, owner-operated businesses on Main Street: plumbing, HVAC, electrical, landscaping, bakeries, cleaning, bookkeeping, back-office services, independent real estate, and operator-led B2B services. Profitable on day one — story optional.
How does Simple Holdings differ from a roll-up?+
We don't strip out the operator to pump a multiple. Founders and operators keep meaningful ownership. We measure success in decades held, not multiples returned. The best business we own is the one we still own in 2050.
Where is Simple Holdings based?+
Greenwich, Connecticut. Operating since 2012. Three bootstrapped exits behind the founder before Simple Holdings was formed to hold.
What is the relationship between Simple Holdings and Bootstrapper Capital?+
Bootstrapper Capital is one of two wings under Simple Holdings — the wing focused on B2B services, bookkeeping, software, and the OWNABLE OS methodology. Blue Collar Capital is the other wing, focused on home services and real estate.
Built to hold. Open to operators.
If you run a profitable Main Street business and you're thinking about what's next, start with the free OWNABLE Assessment.