The Ins and Outs of Selling a Business

The Ins and Outs of Selling a Business

By Keith Dee, Osage AdvisorsBusiness
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The Ins and Outs of Selling a Business episodes

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

    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 can build an effective AI strategy that delivers measurable results. They explore common mistakes businesses make when adopting AI, how to identify high impact use cases, why data matters, and where AI can create the greatest return on investment.

    Whether you're looking to improve operations, increase productivity, or build a more valuable business, this episode offers practical insights into using AI to drive long term growth.


    Contact Keith: Osage Advisors, LLC
    osageadvisors.com
    860-767-3273

    ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

    26 min
  • The Business Valuation Mistake No One Talks About

    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 aren't always what they seem. He shares real world examples of business owners who negotiated one on one with buyers, the risks of skipping a competitive sales process, and why testing the market is critical to maximizing value.

    If you're considering selling your business or have received an unexpected offer, this episode offers practical insights to help you make the right decision before moving forward.


    Contact Keith: Osage Advisors, LLC
    osageadvisors.com
    860-767-3273

    ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

    11 min
  • The AI Advantage Sellers Can't Afford to Ignore

    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 discipline can increase business value. They explore practical ways companies can adopt AI, improve processes, and build the kind of growth strategy buyers are looking for in today's M&A market.

    Whether you're planning to sell in the near future or simply want to build a stronger business, this episode offers valuable insights on using AI and strategic planning to position your company for long-term success.


    Contact Keith: Osage Advisors, LLC
    osageadvisors.com
    860-767-3273

    ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

    27 min
  • One Unexpected Event Can Cost You Millions

    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
    860-767-3273

    ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

    9 min
  • The Final Months Before a Sale Can Make or Break Your Exit

    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
    860-767-3273

    21 min
  • The Buyer Had One Condition: Don’t Leave After the Sale

    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
    860-767-3273

    ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

    8 min
  • Don't Sell Your Business Without Integrating AI First

    Selling a business today requires more than strong financial performance. Buyers are increasingly evaluating how companies use technology, preserve institutional knowledge, and prepare for the future.

    In Part 2 of this conversation, Keith Dee sits down again with Ken Winell, Co-CEO of Nexus Digital Group, to discuss how AI can help businesses capture employee expertise, improve onboarding and training, modernize legacy systems, and enhance value during the sale process. They also explore why every business should have an AI policy and how owners can take practical steps to stay ahead as technology continues to evolve.

    If you're planning to sell your business in the coming years, this episode offers valuable insight into how AI can strengthen your company and support a successful transition.


    Contact Keith:
    Osage Advisors, LLC
    osageadvisors.com
    860-767-3273

    ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

    23 min
  • The Truth About Earnouts: Risks Rewards and Deal Structure

    Selling a business often comes down to one challenge: bridging the valuation gap between buyer and seller.

    In this episode of The Ins and Outs of Selling a Business™, Keith Dee discusses earnouts and why they have become a common tool in today’s M&A market.

    Keith explains how earnouts work, why buyers use them to reduce risk, and how sellers can structure them properly to protect their interests. If you're considering selling your business, this episode provides practical insight into one of the most important deal terms you may encounter.


    Contact Keith:
    Osage Advisors, LLC
    osageadvisors.com
    860-767-3273

    ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

    7 min
  • Why AI Is Becoming a Major Factor in M&A Deals

    Selling a business in today’s market is no longer just about financial performance. Buyers are now asking a new question: “How is your company using AI?”

    In this episode of The Ins and Outs of Selling a Business™, Keith Dee sits down with Ken Winell, Co-CEO of Nexus Digital Group, to discuss how artificial intelligence is changing the way businesses are evaluated, operated, and valued.

    They explore how business owners can prepare for AI-related due diligence, why having an AI policy matters, and how companies are using AI to improve efficiency, supply chain management, HR, marketing, and competitive strategy. If you’re thinking about selling your business, this episode explains why AI readiness could directly impact your valuation.


    Contact Keith:
    Osage Advisors, LLC
    osageadvisors.com
    860-767-3273

    ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

    22 min
  • Why Business Sales Are Taking Longer to Close in Today’s Market

    Why are business sales taking longer to close in today’s market?

    In this episode of The Ins and Outs of Selling a Business™, Keith Dee explains why buyers are moving more cautiously and what business owners can do to keep deals on track. Keith discusses the impact of market uncertainty, buyer hesitation, due diligence pressure, and the importance of being fully prepared before going to market. From financial reviews to management alignment, he shares why preparation is critical to building buyer confidence and maximizing value in today’s M&A environment.

    If you’re considering selling your business, this episode offers practical insights to help you prepare for a smoother and more successful transaction.


    Contact Keith:
    Osage Advisors, LLC
    osageadvisors.com
    860-767-3273

    ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

    8 min

About The Ins and Outs of Selling a Business

From the publisher's feed

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…

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