Simple Holdings
A private holding company for profitable businesses worth owning.
We build, acquire, and back owner-led businesses — then help make them more profitable, durable, and transferable for the next operating economy.
The thesis
AI can reshape the established businesses that already have customers, cash flow, expertise, and trust.
They don't need to become technology companies. They need to become better operating companies.
Outside · preserved
What already works.
Inside · redesigned
How the work gets done.
“The next generation of great businesses may look remarkably similar from the outside — and operate completely differently on the inside.”
01
We create businesses when a recurring customer problem can be turned into a simple, repeatable, profitable company.
02
We acquire established businesses where patient ownership and operating improvement can create long-term value.
03
We invest alongside capable owners and operators when aligned capital and strategic support can help a good business become a better ownership asset.
04
We hold businesses and economic interests with a long-duration mindset and allow strong economics to compound.
Different entry points. Same objective: own better businesses for longer.
The ownership standard
P — Profitability
The business creates meaningful economic value for its owners.
Revenue alone does not make a great business.
D — Durability
The business can continue producing value through changing markets, employees, technology, ownership, and circumstances.
T — Transferability
Customers, knowledge, relationships, systems, processes, and outcomes can survive beyond any single founder or key employee.
Growth increases the size of a business.
Profitability, durability, and transferability increase the quality of ownership.
Good businesses already know how to create value.
AI and the established business
AI is dramatically changing what individuals and small teams can accomplish.
For established companies, the opportunity is not simply replacing people with AI. The more useful question is:
“What needs to happen consistently inside this business — and what is now the best combination of people, software, automation, and AI to make it happen?”
Instead of assuming today's staffing model, workflow, software stack, or owner involvement must continue forever, we examine the recurring systems that actually produce value. Then we redesign them.
Legacy operating model
Implicit work
Modern operating model
Explicit systems
The objective is not AI for the sake of AI. It is a business capable of producing better outcomes with less complexity, less fragility, and less dependence on any single person.
Ecosystem
SIMPLE HOLDINGS.
Ownership + Capital Allocation
Parent holding company
Function
Capital + Investment.
Bootstrapper Capital
Bootstrapper Capital backs.
Function
Acquisition.
Blue Collar Capital
Blue Collar Capital acquires.
Function
Operating Transformation.
Bootstrapper.ai
Bootstrapper.ai transforms.
Function
Relationships + Distribution.
Bootstrapper Media
Bootstrapper newsletter · Bootstrapping to Billions
Media and relationships expands the opportunity set.
Companies perform functions. Simple Holdings sits above them, allocating capital and holding the ownership that results.
How value is created
They need the important work to happen consistently without depending on the owner.
01
Identify what actually creates economic value.
02
Convert recurring value creation into defined operating systems.
03
Choose the correct owner: founder, employee, remote operator, specialist, software, AI, or hybrid.
04
Trigger work. Verify completion. Surface exceptions. Correct failures.
05
Connect execution to meaningful business outcomes.
06
Reinvest resulting cash flow, capability, data, relationships, and enterprise value.
The goal is not automation.
The goal is dependable economic output.
What we look for
We are most interested in established, owner-led businesses with some combination of:
Strengths already in place
Room we can help with
Areas of particular interest
B2B Services · Professional Services · Essential Services · Skilled Trades · Business Infrastructure · Software supporting established businesses · Recurring Service Businesses
“We would rather improve a fundamentally good business than manufacture a story around a fundamentally bad one.”
Founder
Chris Sacchinelli is an entrepreneur, operator, and investor and the founder of Simple Holdings.
After building and exiting bootstrapped businesses earlier in his career, his work increasingly became focused on a simple question: What makes a business genuinely good to own?
Books by Chris Sacchinelli
The Discipline of Long-Term Equity Management
Why profitable businesses still trap their owners — and how to build one that produces durable value without extraordinary dependence on its owner.
“The goal of business is not to grow. The goal of business is to remain ownable — and then to stay that way long enough to win.”
The exit playbook
A framework for creating liquidity and optionality — profit, debt, partial sale, full sale, and succession treated as tools, not stages.
“Exit is not the end of ownership — it is the proof of it.”
Simple Holdings exists to accumulate ownership in businesses we understand, improve, and believe deserve to exist for a long time.
Build carefully.
Own intelligently.
Compound patiently.
The cycle
We are less interested in maximizing the number of transactions than in improving the quality and quantity of ownership over time.
Cash flow is not the endpoint. It becomes fuel for additional ownership.
Contact
The best opportunities often begin long before there is a transaction. We want to know good business owners, operators, investors, lenders, and strategic partners before there is necessarily something to buy, sell, or finance.
Growth · Succession · Partial liquidity · Operating transformation · Partnership · Capital · Future sale
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Run a company · Become an owner · Transform a business · Participate in acquisitions
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Investors · Lenders · Family offices · Capital partners
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Accounting · Finance · Technology · AI · Recruiting · Insurance · Sales · Marketing · Capital · Compliance · Operations
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