Your legacy, continued.
We acquire and steward enduring small businesses,
combining disciplined finance with hands‑on operations
to protect your legacy and unlock the next stage of growth.
About Us
At The Roamingwood Group we believe that small, family‑run businesses are the heart of the country — they keep communities strong, create good jobs, and carry forward the values of hard work and service. Our mission is to be a thoughtful successor who protects that legacy while helping the business thrive in its next chapter.
Our Minnesota and Brooklyn based team is focused on buying and running a single great business for the long term. With more than 20 years of experience in operations, finance, e-commerce, and sales, we know how to strengthen companies through process improvement and technology enablement. We aim to become the next committed owner of a healthy, people‑first business that matters to its employees, customers, and community.
What we’re known for:
Operational excellence and measurable process improvement
Thoughtful modernization (systems, data, and workflow) without disrupting what works
Genuine respect for people, customers, and suppliers
Clean, transparent, and confidential dealmaking
A belief that great small businesses are the backbone of our economy
Meet the Team
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Sara Hillstrom
Founder & Managing Partner
Operator, finance leader, and process builder with 20+ years of experience spanning global enterprises and small businesses alike. She has led in companies generating billions in revenue as well as entrepreneurial ventures, bringing the same focus on impact at every scale. Known for building high-performing teams, streamlining complex workflows, and modernizing systems in ways that improve efficiency without disrupting the front line. Educated in finance and shaped by hands-on P&L leadership, she thrives at the intersection of strategy and execution. Based in Brooklyn, she brings breadth, depth, and a proven track record of driving lasting results.
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Michael
Advisor & Investor
Technology executive, investor, and product leader with 25 years of experience driving growth and innovation across startups and multi-billion-dollar enterprises. He has built and scaled companies across product, go-to-market, and operations, with a track record of creating high-performing teams and delivering market-defining products. He also leads the e-commerce strategy for his family’s 50-year-old butcher shop—giving him a personal connection to the challenges and opportunities of small business. Based in New York City.
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Sam
Principle
Builder and operator with more than a decade of experience in construction and complex project execution. He has led teams building everything from custom boats to Google’s high-voltage Transformers. Brings practical expertise, problem-solving skills, and the ability to “get hands dirty” alongside employees and owners alike. Based in Minnesota.
We’d love to chat
Thinking about succession? We’ll meet you where you are - whether you’re ready now or just exploring options. We’d love to hear from you.
Brokers: Have a lead? We’d love to hear from you. We move fast, handle NDAs right away, and give straightforward feedback every time.
Send us an email at contact@theroamingwoodgroup.com
or use the form here.