Built on Trust, Relationships, and Always Putting the Client First
Defining success as a business owner goes beyond profitability. It’s about impact, legacy, and relationships. In this special episode, Keith Dee reflects on 25 years of Osage Advisors. From launching the firm with no clients and two kids at home, to building a respected M&A advisory company with a reputation for putting clients first.
The Road to Osage
In 2001, Keith recognized a gap in the market for owner-focused M&A services. Big banks were too expensive and emotionally disconnected. Business brokers filled a role, but mainly for main street deals. He envisioned something different, an advisory firm offering institutional-level support for lower middle market, family-owned businesses.
Challenges That Shaped the Business
Osage was built through resilience.
Keith launched the firm five weeks before 9/11. Then came the Great Recession. Later, COVID. Each event brought uncertainty and disruption, but also reinforced the importance of adaptability and commitment.
- During the Great Recession, when dealmaking froze, Keith pivoted to help companies prepare for eventual exits through financial advisory and turnaround work.
- During COVID, while the world paused, he doubled down on rebranding Osage and launched this podcast to offer insights to business owners navigating a complex market.
Investing in What Matters
As Osage grew, so did its commitment to infrastructure and people.
A custom CRM system allowed the team to manage large buyer pools efficiently and keep deals moving. New team members joined to help manage increasing deal flow, including Keith’s son Philip, a proud milestone in the company’s legacy.
Putting Clients First, Always
What makes Osage different is the commitment to the client. Every decision, negotiation, and process is built around what works best for them, not just the deal. If a deal structure doesn’t align with Its Client’s values, Osage recommends they walks away and will remarket the company to find another buyer that is the right fit. That mindset has created long-term relationships and a trusted referral network.
Looking Ahead
Now entering its 25th year, Osage is stronger than ever.
Keith and the team continue to grow, serve new clients, and live out their mission: to help owners make informed decisions, preserve their legacies, and achieve a successful exit on their terms.
Conclusion
There’s no straight line in business building. But through every market shift and personal challenge, Osage Advisors has stayed focused on its core values; client-first service, relationship-driven strategy, and a deep understanding of what it takes to sell a business the right way.
Certain Members of Osage Advisors are Registered Representatives of and conduct securities transactions through StillPoint Capital, LLC, Tampa, FL. Osage and StillPoint are not affiliated.
Osage Advisors provides a lot of guidance in the M&A market here on our blog and on our YouTube channel and Podcast.
