The Ins and Outs of Selling a Business
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Latest episodes
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Before You Announce the Sale: What Every Business Owner Should Know
October 8, 2026 · 7 minOne 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…
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Selling the Family Business: When Legacy, Money & Emotions Collide in an M&A Deal
October 1, 2026 · 26 minWhen 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…
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Selling Your Business? You May Need More Than an Accountant
September 24, 2026 · 6 minWho 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…
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What It Really Takes to Build a Successful M&A Firm Over 25 Years
September 10, 2026 · 19 minWhat 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…
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Before You Accept an Offer for Your Business, Listen to This!
September 3, 2026 · 7 minWhen 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 minTwenty 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…
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How Unexpected Surprised Can Kill a Business Sale
August 20, 2026 · 8 minEven 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…
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The Right Way to use AI in a Business Sale
August 6, 2026 · 23 minAI 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…
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While Everyone Hesitates, You Close the Deal.
July 30, 2026 · 7 minIs 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…
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Can AI Be Trusted With the Biggest Sale of Your Life?
July 23, 2026 · 26 minAI 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…
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The Business Valuation Mistake No One Talks About
July 16, 2026 · 11 minWhat 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…
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The AI Advantage Sellers Can't Afford to Ignore
July 9, 2026 · 26 minAI 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…