The Ins and Outs of Selling a Business

Even 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 concentration late in the due diligence process. He explains how the proposed deal terms could have negatively impacted the seller and how strategic negotiation helped both sides reach a more equitable solution.
If you're considering selling your business, this episode highlights why experienced representation can be critical when unexpected hurdles, retrades, and last minute negotiations arise.
Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273
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AI 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 move beyond AI experimentation and build a practical strategy that drives growth. They explore AI governance, protecting company data, preparing your team for adoption, and why private equity firms are increasingly evaluating AI readiness during the acquisition process.
Whether you're planning to sell your business or simply want to stay competitive, this episode offers practical insights on implementing AI, increasing operational efficiency, and positioning your company for long term value.
Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273
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Is 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 uncertainty. He explains what's driving activity from private equity firms and strategic buyers, why competition for quality businesses is increasing, and what business owners should be doing now to prepare for a successful sale.
If you're considering selling your business, this episode offers timely insights into the current market and how to position yourself to maximize value.Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273
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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 kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

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 kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

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 kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

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

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

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

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 kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w