Built by Operators. Not Brokers.
We’ve been in your seat - building, running, and making real decisions. That perspective changes how we approach every opportunity.
Why We Built Stearns & Oak
Stearns & Oak exists because of a hard lesson. Our founder built a $50M+ business with hundreds of employees and made a costly acquisition along the way. Overpaid. Underprepared. Learned the hard way why real enterprise value matters and how quickly a bad deal can unravel.
After years of building, scaling, and learning, one thing became clear: most business owners approaching an exit are completely unprepared. Not because they're careless but because nobody had ever walked them through what it actually takes to position a business for a strong sale.
That's what Stearns & Oak was built to solve. We work with business owners before, during, and after the transaction bringing the same operational depth, financial rigor, and strategic thinking that built our own business to the deals we work on for our clients.
The Team Behind Every Deal
When you work with Stearns & Oak, you're not getting a lone broker with a license. You're getting access to an entire operational infrastructure the same team that runs a $50M+ business.
Kyle Stearns
Founder & CEO
He scaled and operated a $50M+ business and has worked closely with owners across the country, developing a real-world perspective on growth, operations, and dealmaking. Today, he helps business owners improve their companies, execute acquisitions or exits, and use their business as a vehicle to achieve bigger goals beyond it.
Holden Stearns
Founder & Managing Partner
Business owner and investor who has scaled a $50M+ company, leading the charge on sales, growth, and day-to-day execution. As an operator and real estate investor, he brings a high-performance, results-driven mindset while helping business owners fix what's not working, scale what is, and position their companies for serious growth or exit.
A Network That Moves.
Stearns & Oak doesn't just list businesses. We have direct access to buyer groups and investor networks that closed over 160 acquisitions in 2025 alone. When a seller is ready to move, we already know who the right buyers are.
Acquisitions closed by our buyer network in 2025
Off-market deal sourcing, no public listings
Let's Have a Real Conversation.
No sales pitch. No pressure. Just an honest conversation about where you are and what makes sense for you.
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