The Ins and Outs of Selling a Business

Hosted by Keith Dee, Osage Advisors

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Episodes

100

Latest episode

Jun 2026

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About the show

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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60 recent

June 11, 2026Episode 13322 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 kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

June 4, 2026Episode 1326 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 kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

May 28, 2026Episode 13121 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 kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

May 21, 2026Episode 1307 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 kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

May 14, 2026Episode 12925 min

Burnout Before the Deal? Here's What Goes Wrong

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 members and key employees, and practical strategies for making better decisions when the stakes are highest. If you’re preparing to sell your company, this episode highlights why mental clarity and recovery are critical to getting the right outcome. Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

May 7, 2026Episode 12815 min

How Buyers Revisit Your Sale Price After the Deal Closes

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 areas that can impact what sellers ultimately walk away with after closing. If you’re preparing to sell your business, this episode explains how proper deal structure and experienced advisors can help protect you from costly surprises. Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

April 30, 2026Episode 12721 min

How to Stay Sharp and Avoid Costly Mistakes During a Business Sale

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 struggle during due diligence. If you’re preparing to sell, this episode shows how to stay focused, avoid reactive decisions, and perform at your best when it matters most. Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

April 23, 2026Episode 1267 min

Should You Sell Your Business Now or Wait? Here's the Reality

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 years of delays, many owners are running out of time to wait. If you’ve been holding off on selling, this episode breaks down why now may be the time to test the market and make a move. Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

April 16, 2026Episode 12523 min

Why Sellers Lose Deals: The Mindset Mistake That Kills Value

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 owners shift from “playing to win” to “playing not to lose” and how that can derail a deal. If you’re preparing to sell your business or currently in the middle of a transaction, this episode will help you stay grounded, focused, and in control from start to finish. Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

April 9, 2026Episode 1248 min

Can Your Buyer Actually Close? What Every Seller Needs to Know

You have a deal on the table, but can the buyer actually close? In this episode of The Ins and Outs of Selling a Business™, Keith Dee explains why certainty of close is one of the most overlooked and critical factors in any transaction. From private equity firms to independent sponsors, not every buyer has the capital or structure to get a deal done. Learn how to spot red flags, evaluate financial strength, and avoid costly delays or failed deals. Because in the end, the best deal is the one that actually closes. Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w