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The Ins and Outs of Selling a Business

The Ins and Outs of Selling a Business

By: Keith Dee Osage Advisors
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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.Copyright 2022 All rights reserved. Economics
Episodes
  • One Unexpected Event Can Cost You Millions
    Jul 2 2026

    What does it mean when everyone in an M&A deal says, "Pens down"?

    In this episode of The Ins and Outs of Selling a Business™, Keith Dee explains one of the most common moments of tension during a business sale: when negotiations temporarily come to a halt. He discusses why deals pause, the business issues that typically cause delays, and why the best solutions often come from conversations between buyers and sellers, not battles between attorneys.

    If you're preparing to sell your business, this episode offers practical insight into navigating deal roadblocks, resolving negotiations, and keeping your transaction moving toward a successful closing. Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

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    8 mins
  • The Final Months Before a Sale Can Make or Break Your Exit
    Jun 25 2026

    A strong growth strategy can make the difference between an average valuation and a premium one.

    In this episode of The Ins and Outs of Selling a Business™, Keith Dee sits down with Marc Emmer, President of Optimize, Inc., to discuss why buyers invest in future growth, not just past performance. Together, they explore how market positioning, strategic planning, leadership alignment, and AI are shaping business value in today's M&A market.

    Whether you're planning to sell in one year or five, this episode offers practical insights on building a compelling growth story, preparing your leadership team, and positioning your company for a successful exit. Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273

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    20 mins
  • The Buyer Had One Condition: Don’t Leave After the Sale
    Jun 18 2026

    What happens when the right buyer wants you to stay with the business longer than you planned?

    In this episode of The Ins and Outs of Selling a Business™, Keith Dee discusses one of the most common challenges business owners face during negotiations: extending their post-closing transition period. He explains why buyers often require sellers to stay involved longer, how that request impacts deal structure, and why it doesn't necessarily mean giving up the lifestyle you've worked so hard to create.

    If you're considering selling your business, this episode offers practical insight into balancing your personal goals with what buyers need to complete a successful transaction. Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

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    8 mins
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