Capital That Works as Hard as You Did
Cherry Oak Capital acquires and invests in businesses built on predictable, durable revenue. We bring capital, strategy, and structure that protects what you built.
Our Investment Thesis
We Invest in Certainty
Most capital chases growth. We pursue durability.
Cherry Oak Capital targets businesses with revenue that does not depend on unpredictable markets, fluctuating demand, or a single client relationship. The businesses we acquire and invest in generate income that is consistent, contractual, or structurally recurring in nature.
We believe the most valuable businesses are not always the fastest-growing ones. They are the ones that perform in any economic environment. That is where we place our capital and our focus.
What We Look For
Businesses Built on a Reliable Foundation
We seek owner-operated businesses with income that renews, repeats, or is anchored to long-term demand. This includes, but is not limited to:• Residential and commercial communities with consistent occupancy
• Businesses with long-term tenants or contractual occupants
• Service businesses with locked-in client relationships or subscription structures
• Asset-based businesses where demand is driven by structural need, not discretionary spendingIf your business generates income that holders and tenants depend on, we want to hear from you.Revenue Range We Work With: $200,000 to $10,000,000 in annual revenue
Our Edge as a Buyer
More Than a Transaction
We structure every acquisition and investment around the specific needs of the founder. That means flexibility in how a deal is structured, and a genuine interest in what happens after the close.What that looks like in practice:• Tax-Advantaged Structuring
We work with advisors to structure transactions in a way that minimizes your tax exposure at close. You spent years building this business. You should keep more of what it is worth.• Rollover Equity
Founders who believe in the future value of their business can retain an equity stake. When Cherry Oak sells or recapitalizes in the future, you participate in that upside a second time.• Preservation of Legacy
We do not acquire businesses to dismantle them. We acquire businesses that we intend to grow. Your team, your culture, and your reputation matter to us beyond the close date.• Growth Strategy
We bring operational and capital resources to every business we acquire. Founders who exit to Cherry Oak are not handing their business to a passive hold. They are handing it to a team committed to expanding what they built.• Founder-Friendly Terms
We move fast, communicate clearly, and structure deals that work for both sides. We do not use complexity as leverage.
Work With Us
Ready to Explore a Partnership?
Whether you are a founder considering a sale, or an investor or intermediary with an opportunity to discuss, we want to hear from you. Submit an inquiry below and a member of our team will follow up within two business days.
Michael Livingston is the founder of Cherry Oak Capital, a private investment firm focused on acquiring and operating established lower middle market businesses.
He works directly with business owners to structure thoughtful transitions centered around continuity, long-term stewardship, and operational stability. Cherry Oak Capital takes a disciplined, relationship-driven approach to acquisitions and seeks to preserve the legacy and foundation owners have built over time.
Cherry Oak Capital
Sitka, Alaska
Cherry Oak Capital is a private acquisition and investment firm. All inquiries are subject to our Privacy Policy and Terms of Use. Nothing on this page constitutes a securities offering or solicitation.