The Ins and Outs of Selling a Business

Keith Dee, Osage Advisors
  • 5.0 (4)
  • BUSINESS
  • UPDATED WEEKLY

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.

  1. Can Your Kids Really Run the Business? What to Know Before You Hand It Over

    4D AGO

    Can Your Kids Really Run the Business? What to Know Before You Hand It Over

    When it comes to succession planning, the biggest challenges aren’t always financial—they’re emotional. In this episode of The Ins and Outs of Selling a Business™, Keith Dee continues his conversation with Jeff Savlov, a family business consultant and therapist who helps owners navigate the complex emotional and relational dynamics of passing a business to the next generation. From entitlement issues and unqualified heirs to blended families and silent resentment, Jeff shares real stories and insights on how to address tough conversations early, avoid costly mistakes, and keep both the family and the business intact. Whether you're planning a handoff to your kids or considering a sale, this episode is packed with powerful takeaways on how to handle the human side of succession. Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

    20 min
  2. Why 2026 Could Be the Best Year Yet to Exit Your Business

    FEB 5

    Why 2026 Could Be the Best Year Yet to Exit Your Business

    Is Now a Good Time to Sell Your Business? Here's What We're Seeing "How's the market?" It’s the question we’re hearing from nearly every business owner right now. In this episode of The Ins and Outs of Selling a Business™, Keith Dee, President of Osage Advisors, shares why 2026 could be a strong year for M&A. With plenty of capital on the sidelines and renewed interest from both private equity and strategic buyers, the environment is shifting in a seller’s favor. If you’ve been waiting for the right time, this episode explains what to watch for and how to take advantage of current market conditions.   Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

    5 min
  3. Selling the Family Business: Avoiding Drama, Conflict, and Hurt Feelings

    JAN 30

    Selling the Family Business: Avoiding Drama, Conflict, and Hurt Feelings

    What happens when your children don’t want your business, or worse, expect to inherit it without paying? In this episode of The Ins and Outs of Selling a Business™, Keith Dee talks with family business & wealth consultant, Jeff Savlov of Blum & Savlov, LLP, about how entitlement, silence, and poor planning can derail succession. Jeff shares his personal story and practical tips to help business owners avoid conflict and protect both their legacy and family relationships.   Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

    21 min
  4. How Emotions Can Derail Your Business Sale (And How to Stop It)

    JAN 22

    How Emotions Can Derail Your Business Sale (And How to Stop It)

    Selling a business isn’t just about numbers. For many owners, especially those nearing retirement, it can bring up unexpected emotions that impact decision making. In this episode of The Ins and Outs of Selling a Business™, Keith Dee of Osage Advisors talks about a challenge many sellers face but few discuss: emotional vulnerability. From uncertainty about life after the sale to pressure from family, these emotions can derail even the strongest deals if not addressed. Keith shares what to expect and how to navigate it with the right support and preparation. Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

    9 min
  5. How to Prepare for Buyer Demands After the LOI

    JAN 15

    How to Prepare for Buyer Demands After the LOI

    In this episode of The Ins and Outs of Selling a Business™, Keith Dee of Osage Advisors is joined by Philip FitzGerald of Amplify Consulting Services to talk about what many sellers don’t see coming… the intensity of due diligence after a letter of intent is signed. We cover why today’s buyers demand so much more information, how private equity firms and their consultants operate, and why sellers need to be fully prepared before they go to market. From document requests to unexpected delays, how you plan ahead can determine whether your deal moves forward or falls apart. If you’re thinking about selling, this episode gives you a clear view of what to expect, and how to stay ahead of it. Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

    20 min
  6. Selling Your Business? Don't Share THIS Before the LOI

    JAN 8

    Selling Your Business? Don't Share THIS Before the LOI

    How Much Should You Share Before the LOI? In this episode, we cover a key question in the M&A process: what information should you share with buyers before a Letter of Intent is signed? Keith Dee of Osage Advisors explains how to balance transparency with confidentiality, what goes into a CIM, and why today’s buyers often ask for more upfront. We also share how the right info early on can speed up due diligence later. If you're preparing to sell, this episode will help you share the right details at the right time. Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

    12 min
  7. The $40M Myths That Almost Cost This Founder Everything

    JAN 2

    The $40M Myths That Almost Cost This Founder Everything

    Thinking about selling your business? Don’t guess your company’s value. In this episode, Keith Dee from Osage Advisors sits down with Philip Fitzgerald of Amplified Consulting Group to break down M&A prep for first-time sellers and family-owned businesses. Learn the real steps to understand your business’s worth, avoid common mistakes, and get the most out of your exit.    Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

    23 min
  8. Selling a Family Business: How to Get Everyone on Board

    12/26/2025

    Selling a Family Business: How to Get Everyone on Board

    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

    10 min
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Ratings & Reviews

5
out of 5
4 Ratings

About

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.

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