The Ins and Outs of Selling a Business

Twenty five years ago, Keith Dee founded Osage Advisors with no clients, two young children at home, and a vision to provide business owners with a better way to sell their companies.

In Part 1 of this special 25th anniversary episode of The Ins and Outs of Selling a Business™, Keith reflects on the early days of Osage, the lessons that shaped the firm, and why trust, transparency, and understanding an o...

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 ...

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,...

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 o...

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, ...

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...

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 ...

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 bu...

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 bu...

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 structur...

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, m...

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 ...

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.

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...

Selling a business can test even the strongest leaders, especially when stress, internal conflict, and decision fatigue begin to build.

In Part 2 of this conversation, Keith Dee sits down again with Dr. Parker Hays of Lasting Impact Wellness to discuss how business owners can stay focused and resilient throughout the sales process. They explore burnout, emotional endurance, handling pressure from family ...

You sold your business… then the buyer came back with a different number.

In this episode of The Ins and Outs of Selling a Business™, Keith Dee explains the post-closing true-up process and why it can become one of the most frustrating parts of a transaction.

From working capital disputes and inventory adjustments to indemnification claims and earnouts, Keith breaks down the key area...

Selling a business is a high-pressure process and performance matters.

In this episode of The Ins and Outs of Selling a Business™, Keith Dee speaks with Dr. Parker Hays, emergency physician and performance coach, about how to stay sharp when the stakes are highest. They discuss why performance under pressure is a trainable skill, how values and mindset impact decision-making, and why many sellers struggl...

How’s the market for selling a business right now?

In this episode of The Ins and Outs of Selling a Business™, Keith Dee explains how years of uncertainty, from COVID to interest rates and global events, have impacted M&A and why timing matters more than ever. With significant capital still on the sidelines and motivated buyers in the market, there is real opportunity for sellers. But after yea...

Selling a business isn’t just a financial transaction. It’s a mental game.

In this episode of The Ins and Outs of Selling a Business™, Keith Dee sits down with performance coach Lauren Johnson to explore how mindset directly impacts outcomes during a sale.

From navigating due diligence to managing stress, uncertainty, and outside pressures, they break down why many business owne...