The Ins and Outs of Selling a Business

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

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

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

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

The Psychology of Selling a Business and Why It Affects Your Decisions

Selling your business is not just a financial transaction. It is a mental and emotional one that can impact every decision you make along the way.
In this episode of The Ins and Outs of Selling a Business™, Keith Dee sits down with mental performance coach Lauren Johnson, who has worked with elite athletes, executives, and high performers under pressure. Together, they break down how mindset, preparation, and emotional control play a critical role before, during, and after a sale.
From preparing for buyer meetings to navigating due diligence and managing the pressure of uncertainty, this conversation highlights why mastering your internal world is just as important as structuring the deal.
If you are thinking about selling your company or currently in a transaction, this episode will help you stay focused, confident, and in control 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

Why You Should NEVER Talk to a Buyer Without an Advisor

Selling your business is not as simple as taking a call from a buyer. In many cases, it can lead to wasted time, lost value, and deals that fall apart.
In this episode of The Ins and Outs of Selling a Business™, Keith Dee shares real examples of what can go wrong when owners engage buyers without proper preparation. From lowball offers to failed deals and costly due diligence, these situations are more common than you think.
The message is simple. Don’t go it alone. A structured process and the right advisors are key to protecting your outcome and maximizing value.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 Hidden Risk in Selling Your Business: Family and Team Conflict

In this episode, we continue our conversation with Ellen Palmer on the often overlooked human side of selling a business.
As deals move forward, misalignment with family members, partners, or key employees can create stress and put the transaction at risk. We discuss why early communication, stakeholder alignment, and honest conversations are essential to keeping deals on track.
If you are preparing to sell or currently in a transaction, this episode highlights how managing people and emotions can make or break the 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

What Happens When Your Chosen CEO Can't Lead After You Sell

As a business owner, building a strong leadership team is critical, especially when preparing to sell your company. But what happens when the person you expected to take over isn’t ready, loses confidence, or creates complications during the sale process?
In this episode of The Ins and Outs of Selling a Business™, Keith Dee discusses a common challenge sellers face when their chosen successor becomes part of the transaction. Whether the buyer questions their leadership ability, the individual hesitates to step into the role, or contract negotiations create unexpected tension, these situations can add stress and risk to a deal.
Keith shares real-world insights on how to prepare key leaders for a transition, avoid deal disruptions, and protect the outcome of your sale.Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w