Wing I · Est. 2015
Blue Collar Capital
Home services, trades, and real estate — the businesses that keep the lights on, the lawns cut, and the pipes running.
Explore Wing I →A holding company for Main Street · Est. 2012
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.
Connecticut, USA · A company by Chris Sacchinelli · -42 years operating
-42
Years operating
02
Portfolios under roof
03
Bootstrapped exits
36.3M
Businesses we serve
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 & electrical
- ●Landscaping & lawn care
- ●Bakeries, diners & shopkeeps
- ●Cleaning, painting & handyman
- ●Bookkeeping & back-office services
- ●Independent real estate holdings
- ●Trades succession & 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.”
Our approach
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 A.I. Repeat for thirty years. That's the entire playbook.
The portfolio
Two houses. One roof.
Wing II · Est. 2020
Bootstrapper Capital
Bookkeepers, B2B services, and the software the corner shop actually needs. Capital and tools for operators ready to graduate from hustle to holding.
Explore Wing II →
Bootstrapper.ai · Free to join
Find your local chapter.
Operators meeting operators — in your town, every month. No dues. No pitch decks. Coffee, work, and the people who actually run things.
© 1970 Simple Holdings · Connecticut