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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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About this listen

 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
  • Selling a Family Business: How to Get Everyone on Board

    Selling a Family Business: How to Get Everyone on Board
    Dec 26 2025

    Selling a Family Business? What If the Next Generation Gets Cold Feet?

    In this episode, we explore what happens when your family isn’t fully on board with your decision to sell. From hesitation to outright resistance, these moments can derail a deal if not handled carefully.

    Learn how to align your family, communicate your goals, and protect the value of your business through a smooth transition.

    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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    10 mins
  • Deals That Almost Died: How We Sold Businesses No One Wanted to Buy

    Deals That Almost Died: How We Sold Businesses No One Wanted to Buy
    Dec 18 2025

    In this episode of The Ins and Outs of Selling a Business, Keith is joined by Jim Young and Philip Dee for a candid year-in-review of 2025’s most complex deals. Together, they unpack transactions that nearly fell apart, required creative structures, and demanded constant pivots to close.

    From how special business designations impact valuation to earn-outs, seller notes, operational challenges, and deals that drew hundreds of buyers but only a few real contenders, this episode offers a behind-the-scenes look at what it really takes to get deals done.

    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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    25 mins
  • Seller Notes Explained: The Deal Structure Buyers LOVE, and Sellers Benefit From

    Seller Notes Explained: The Deal Structure Buyers LOVE, and Sellers Benefit From
    Dec 11 2025

    In this episode, we break down seller notes, one of the most common (and misunderstood) tools in M&A deal structuring.

    We explain what seller notes are, why buyers love them, and how sellers can actually benefit from offering financing as part of the deal. From increasing your sale price to helping a deal cross the finish line, seller notes can be a powerful tool when used the right way.

    If you're preparing to sell your business or just want to understand what makes deals work, this episode is packed with insights on how to structure a win-win.

    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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    9 mins
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