A tech-enabled professional firm built for owner-led businesses.
Long-term equity management is a discipline. Bootstrapper Capital is the firm that practices it — combining fiduciary-grade advisory, a purpose-built software platform, and a credentialed affiliated-firm network.
The three layers of the firm
Most advisory firms are one of three things: a partner shop with senior people and no leverage, a software company with no judgment in the loop, or a marketplace of unvetted referrals. Bootstrapper Capital is structured to be all three at once — and to keep them honest about each other.
Principals
The in-house team that sets the doctrine, publishes the method, and stewards the affiliated network. Engagements at the principal level are limited and reserved for firm-defining work.
The Platform
Bootstrapper.ai — the system of record for ownership, equity, and the OWNABLE OS. The platform delivers the standard work so principals and affiliates spend their time on judgment, not on producing the same artifact a thousand times.
Affiliated Firms
Independent CFOs, bookkeepers, exit advisors, and operators credentialed to deliver the OWNABLE OS in their markets. The affiliated network is how owners across the country get the firm without flying it in.
What we do not do
The boundaries of a professional firm matter as much as its services. We publish ours so there is no ambiguity for the people we work with — or the people we don't.
- We do not acquire client businesses. We are not a private equity firm.
- We do not broker transactions. We do not earn commissions on M&A.
- We do not provide tax, legal, or accounting advice. We coordinate with your licensed professionals.
- We do not accept referral fees from lenders, brokers, or platforms.
- We do not sell leads, list services, or run a marketplace.
- We do not take operational control. The owner runs the company; we run the doctrine.
How the firm relates to the rest of the brand
People often conflate the firm with the parent or with the founder. Three things, three pages:
- Bootstrapper Capital — the operating firm. Doctrine, platform, advisory, capital pathways, the SMB Accelerator, the Affiliated Firms.
- Simple Holdings — the Connecticut continuous-capital parent. Holds the businesses; doesn't flip them.
- Chris Sacchinelli — founder and principal author. Three bootstrapped exits, two books, one podcast.
"The goal of an owner-led business is to stay in business — and still exit on its owner's terms. Long-term equity management is the discipline that makes both possible."— The firm's operating thesis
The institutional posture
We run the firm the way a fiduciary practice should be run, even though the work itself is not a regulated advisory product. That means published doctrine, written engagement scopes, conflict-of-interest disclosures, no contingent transaction fees, and a clear line between the firm's judgment and the client's decisions. The institutional posture is why owners and affiliated firms both trust the work.
Read the doctrine
The firm is the institution. The next four pages are the doctrine that institution runs on.
- The Approach →
The method — long-term equity management, the OWNABLE OS, and how they fit together.
- The Practice →
How engagements actually work — phases, deliverables, cadence, decision rights.
- The Outcomes →
What we measure, what we will and won't claim, and how to read the evidence.
- Who We Serve →
Founders & owners, affiliated firms, strategic partners — three audiences, one firm.
Frequently asked questions
What kind of firm is Bootstrapper Capital?+
A tech-enabled professional firm — a long-term equity management firm for owner-led businesses. We combine fiduciary-grade advisory with a software platform (Bootstrapper.ai) and an affiliated-firm network that delivers the OWNABLE OS at scale.
Is Bootstrapper Capital regulated like an RIA or a broker-dealer?+
No. We are not an investment adviser, broker-dealer, or transactional intermediary. We provide long-term equity management advisory and the technology that runs it. We do not provide tax, legal, or accounting advice; we coordinate with the client's licensed professionals.
Who owns Bootstrapper Capital?+
Bootstrapper Capital is Wing II of Simple Holdings, a Connecticut continuous-capital company founded by Chris Sacchinelli. Simple Holdings holds the businesses; Bootstrapper Capital is the firm that runs the method.
How is the firm staffed and delivered?+
Three layers: (1) the in-house principals who set doctrine, (2) the Bootstrapper.ai platform that delivers the standard work, and (3) the Affiliated Firms network — independent CFOs, bookkeepers, exit advisors, and operators credentialed to deliver the OWNABLE OS in their markets.
Does the firm take referral fees or commissions?+
No. Bootstrapper Capital does not accept referral fees, commissions, or revenue share from lenders, brokers, or transaction partners. Independence is the precondition of the work.
Want to see whether the firm fits your situation?
Start with the 12-minute Ownership Assessment. You'll see exactly which parts of the OWNABLE OS apply to your business and which don't.