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Business

The Ins and Outs of Selling a Business

by Keith Dee, Osage Advisors

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Latest episodes

  • Before You Announce the Sale: What Every Business Owner Should Know

    October 8, 2026 · 7 min

    One of the biggest concerns business owners have when selling their company is confidentiality. How do you protect sensitive information while finding the right buyer? In this episode of The Ins and Outs of Selling a Business™, Keith Dee…

  • Selling the Family Business: When Legacy, Money & Emotions Collide in an M&A Deal

    October 1, 2026 · 26 min

    When a family sells a business, the hardest part isn’t always the numbers. It’s navigating the relationships, expectations, and emotions that come with it. In this episode of The Ins and Outs of Selling a Business™, Keith Dee is joined by…

  • Selling Your Business? You May Need More Than an Accountant

    September 24, 2026 · 6 min

    Who is handling the financial side of your business when it’s time to sell? In this episode of The Ins and Outs of Selling a Business™, Keith Dee explains why having the right financial support can be critical during an M&A transaction…

  • What It Really Takes to Build a Successful M&A Firm Over 25 Years

    September 10, 2026 · 19 min

    What does it take to build a business that lasts 25 years? In Part 2 of this special anniversary episode of The Ins and Outs of Selling a Business™, Keith Dee reflects on the challenges, pivotal decisions, and lessons that shaped Osage…

  • Before You Accept an Offer for Your Business, Listen to This!

    September 3, 2026 · 7 min

    When selling your business, how do you know you’re getting the best possible deal? In this episode of The Ins and Outs of Selling a Business™, Keith Dee shares real world examples of business owners who received dramatically different…

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  • It Took 25 Years to Build This M&A Firm — Here’s What We Learned!

    August 27, 2026 · 17 min

    Twenty five years ago, Keith Dee founded Osage Advisors with no clients, two young children at home, and a vision to provide business owners with a better way to sell their companies. In Part 1 of this special 25th anniversary episode of…

  • How Unexpected Surprised Can Kill a Business Sale

    August 20, 2026 · 8 min

    Even when an M&A deal is progressing smoothly, unexpected issues can surface at any time. In this episode of The Ins and Outs of Selling a Business™, Keith Dee shares a real world example of a buyer raising concerns over customer…

  • The Right Way to use AI in a Business Sale

    August 6, 2026 · 23 min

    AI is no longer just a competitive advantage. It's becoming a key factor in how businesses are valued. In Part 2 of this conversation, Keith Dee sits down again with Brandon Powell, CEO of HatchWorks AI, to discuss how business owners can…

  • While Everyone Hesitates, You Close the Deal.

    July 30, 2026 · 7 min

    Is now a good time to sell your business? In this episode of The Ins and Outs of Selling a Business™, Keith Dee shares an inside look at today's M&A market and why buyer demand remains strong despite recent economic and geopolitical…

  • Can AI Be Trusted With the Biggest Sale of Your Life?

    July 23, 2026 · 26 min

    AI is everywhere, but how do business owners separate real opportunities from the hype? In this episode of The Ins and Outs of Selling a Business™, Keith Dee sits down with Brandon Powell, CEO of HatchWorks AI, to discuss how companies…

  • The Business Valuation Mistake No One Talks About

    July 16, 2026 · 11 min

    What should you do when a buyer contacts you directly about purchasing your business? In this episode of The Ins and Outs of Selling a Business™, Keith Dee explains why unsolicited offers from strategic buyers and private equity firms…

  • The AI Advantage Sellers Can't Afford to Ignore

    July 9, 2026 · 26 min

    AI is changing the way businesses compete, and buyers are paying attention. In Part 2 of this conversation, Keith Dee sits down again with Mark Emmer, President of Optimize, Inc., to discuss how AI, strategic planning, and operational…

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About the show

This podcast taps the expertise of Keith Dee, President and CEO of Osage Advisors, with more than 30 years of experience advising business owners and families of midsize companies and helping them maximize value through M&A and capital transactions.