The Ins and Outs of Selling a Business

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

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 kdee@osageadvisors.com 860-767-3273

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

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

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

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

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

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

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

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