Twenty-five years ago, on August 1, 2001, I started Osage Advisors with a simple belief: that founder-owned businesses in the lower middle market deserved the same level of service and the same far-reaching auction process that big banks reserved for much larger companies. In 2001, there weren’t many options for lower middle market business owners. I wanted to change that.
A quarter-century later, the market looks very different, but our mission remains the same.
Today, we continue to learn, continue to grow, and continue to help owners find the best outcomes every day. Below are three deals that made an impact on me in the past decade — and reinforced the lessons I’ve seen time and time again.
Tier One | Closed March 2021
When Tier One’s first trip to market produced offers below expectations, we made the call to pull the deal. We helped them identify they were losing money on 20% of their SKUs, renegotiated pricing with a key customer, and watched their margins improve dramatically. Two years later, we sold the business for 2x the valuation we would have achieved the first time around.
If it’s not the right deal, don’t do it.
Brimar | Closed December 2021
Brimar’s owner had been approached by a PE fund and called me to test the market. We met, and he signed within 24 hours. The process generated 29 IOIs and 19 LOIs – the most activity we’ve ever seen on a deal — with the highest bid coming in 400% above the low. In the end, the seller chose the second-highest offer because culture and tit mattered more than the last dollar.
Running a full auction process helps to maximize value.
Integ | Closed February 2026
Integ came to us two years before they were ready to sell, and we helped them prepare. By the time they went to market, they’d grown sixfold — which drew enormous interest but also complicated the financing. Many buyers couldn’t get bank approval for a transaction with such rapid growth. We found a buyer with a strong balance sheet and a strategic reason to enter their market, and the entire team stayed intact.
High growth doesn’t always mean an easy sale; but it does mean you need to focus on finding the right buyer.
Twenty-five years. Hundreds of business owners. Countless moments that reminded me why this work matters.
My sincere gratitude to everyone who has been part of the Osage Advisors journey — our clients, our referral partners, and the many relationships that have made this firm what it is. None of this happens without the trust you’ve placed in us, and I don’t take that lightly.
I look forward to everything still ahead — the next owner with a business they’ve spent a lifetime building, the next referral partner who trusts us with someone they care about, or the next deal that reminds me why I started Osage.
Keith Dee
President, Osage Advisors
