Building the standard for modern ownership.
I'm Chris Sacchinelli. In the early 2010s I was fortunate enough to bootstrap and exit a handful of seven- and eight-figure businesses. Then I stepped back, slowed down, and started rebuilding — not for speed this time, but for simplicity, profitability, and endurance.
What I learned from exiting
Like many entrepreneurs, I was chasing freedom but found myself trapped inside what I built. I had wealth on paper, but not ownership in practice. Success didn't always feel successful.
So I stepped back. I slowed down. And I started rebuilding — not for speed this time, but for simplicity, profitability, and endurance. Over the past decade I've been quietly constructing Simple Holdings: a long-term, privately-held company designed to build, buy, and back ownable businesses.
The purpose behind Simple Holdings
Simple Holdings exists to prove three things: that entrepreneurship doesn't have to mean exhaustion, that wealth doesn't have to mean waste, and that ownership can be engineered — intentionally, systematically, and ethically.
Every company we build or back operates on a single standard — the Ownable Methodology — a framework to help founders transform their companies into transferable, capital-ready assets. An ownable business is:
- Profitable enough to sustain itself.
- Systemized enough to scale without the founder.
- Valuable enough that anyone would buy it — yet so fulfilling you'll never want to sell.
Through Bootstrapper.ai (the platform), LTEM (the advisory firm), Bootstrapper Capital (the capital firm), and the Exit Studio (the cohorts), we've turned this standard into a repeatable system.
Why I'm doing this now
The biggest opportunity in business today isn't found in the next startup trend — it's in stabilizing the backbone of the economy: small and midsize businesses. These are the companies that create jobs, support communities, and fuel long-term prosperity. Yet they're often left without the tools, systems, or capital structures to truly scale.
My purpose now is to change that — to bring the sophistication of private equity to the soul of small business. Quietly, patiently, and profitably.
"An ownable business is one so valuable anyone would buy it, yet so profitable you'll never want to sell."
My obsession
Building systems that make small businesses ownable, process-driven, and profit-led. A business so valuable anyone would want to buy it. So profitable you will never sell.
How I invest
I build them. Then I invest in and buy them through my family holdco, Simple Holdings. I believe you can never guarantee outcomes — but you can always control your process.
Books & writing
- Ownable — The Missing Manual for Owners. The field guide for turning a good business into a transferable, scalable, investor-grade asset.
- Exit With Ownership — Philosophy & Framework. The path of the 5 Exits of Ownership — from exiting the job you built to exiting active ownership.
- The Wedge Equity Workbook. Remove risk. Increase value. Grow the equity wedge.
- The Book on Bootstrapping. Practical, profit-led execution for operators.
- The Investopreneur Journal. Align your life, numbers, and strategy weekly.
- Simple Profits Newsletter. Weekly playbook for profit-led, equity-first operators.
What I'm working on
- Running Simple Holdings and its two wings — Bootstrapper Capital and Blue Collar Capital.
- Shipping the Bootstrapper.ai platform — the operating system version of the methodology.
- Hosting Bootstrapping to Billions across audio and YouTube.
- Writing the weekly newsletter to 50,000+ owners.
- Leading LTEM Advisory engagements and the SMB Accelerator cohorts.
Connect & learn
- YouTube · @bootstrappercap — deep dives on ownership, equity building, and bootstrapping strategies.
- LinkedIn · linkedin.com/in/chrissacchinelli
- Newsletter · Weekly playbook for profit-led, equity-first operators
- Press & speaking · press@bootstrappercapital.com
- Simple Holdings →
The holding company. Buy. Build. Back.
- Bootstrapper Capital →
The firm that runs the methodology.
- Long-Term Equity Management →
The discipline behind the work.
- Ownable & Exit With Ownership →
The source material.
Frequently asked questions
Who is Chris Sacchinelli?+
Chris Sacchinelli is a Connecticut-based operator and founder. In the early 2010s he bootstrapped and exited a handful of seven- and eight-figure businesses. In 2012 he founded Simple Holdings, a continuous capital company built to hold rather than flip, and developed the Ownable Methodology — the system he now teaches through Bootstrapper Capital, Bootstrapper.ai, LTEM Advisory, and the Exit Studio.
What is Chris Sacchinelli's obsession?+
Building systems that make small businesses ownable, process-driven, and profit-led — a business so valuable anyone would want to buy it, yet so profitable you'll never want to sell.
Why did Chris step back after exiting?+
He realized success didn't always feel successful. He had wealth on paper but not ownership in practice — trapped inside what he built. So he slowed down and rebuilt for simplicity, profitability, and endurance instead of speed.
What books has Chris Sacchinelli written?+
Ownable: The Missing Manual for Owners; Exit With Ownership (the philosophy and framework behind the 5 Exits of Ownership); The Wedge Equity Workbook; and The Book on Bootstrapping. He also publishes the Investopreneur Journal and the Simple Profits Newsletter.
Where can I follow Chris Sacchinelli?+
On the Bootstrapping to Billions podcast and YouTube channel (@bootstrappercap), on LinkedIn at linkedin.com/in/chrissacchinelli, and through the weekly Simple Profits / Bootstrapper Capital newsletters.
What does Chris mean by 'quiet, patient, profitable'?+
It's the operating posture of Simple Holdings — bring the sophistication of private equity to the soul of small business, but do it without noise, without forced exits, and without the cult of growth-at-all-costs.
Build it ownable.
The free OWNABLE Assessment shows you where your business stands on the same standard I use in Simple Holdings.