The Ins and Outs of Selling a Business

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

When Your Life’s Work Is for Sale: What Selling Your Business Really Feels Like

Selling a business is not just a financial transaction. It is also a deeply personal and emotional journey for founders and their families.
In this episode of The Ins and Outs of Selling a Business™, Keith Dee sits down with life coach Ellen Palmer to discuss why emotional preparedness plays a critical role in the sale process. They explore how stress, identity, and sustained pressure can affect decision making, especially during due diligence.
If you are preparing to sell your company or currently in the middle of a deal, this conversation highlights an often overlooked factor that can make or break a successful 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

60 Days to Close… Or Lose Everything

You’ve signed the Letter of Intent, but the deal is far from done. In this episode, Keith Dee of Osage Advisors explains why the 60 to 90 days after an LOI are the most critical stage of a sale. As due diligence intensifies, buyers dig deeper into your financials, legal documents, customers, and operations.
This is where mindset becomes key. Sellers must shift from protective owner to committed closer, embracing transparency and urgency to maintain momentum and protect value. If you’re entering or navigating the post-LOI phase, this episode outlines what it really takes to reach 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

Can Your Kids Really Run the Business? What to Know Before You Hand It Over

When it comes to succession planning, the biggest challenges aren’t always financial—they’re emotional. In this episode of The Ins and Outs of Selling a Business™, Keith Dee continues his conversation with Jeff Savlov, a family business consultant and therapist who helps owners navigate the complex emotional and relational dynamics of passing a business to the next generation.
From entitlement issues and unqualified heirs to blended families and silent resentment, Jeff shares real stories and insights on how to address tough conversations early, avoid costly mistakes, and keep both the family and the business intact.
Whether you're planning a handoff to your kids or considering a sale, this episode is packed with powerful takeaways on how to handle the human side of succession.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 2026 Could Be the Best Year Yet to Exit Your Business

Is Now a Good Time to Sell Your Business? Here's What We're Seeing
"How's the market?" It’s the question we’re hearing from nearly every business owner right now.
In this episode of The Ins and Outs of Selling a Business™, Keith Dee, President of Osage Advisors, shares why 2026 could be a strong year for M&A. With plenty of capital on the sidelines and renewed interest from both private equity and strategic buyers, the environment is shifting in a seller’s favor.
If you’ve been waiting for the right time, this episode explains what to watch for and how to take advantage of current market conditions.
 
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 the Family Business: Avoiding Drama, Conflict, and Hurt Feelings

What happens when your children don’t want your business, or worse, expect to inherit it without paying?
In this episode of The Ins and Outs of Selling a Business™, Keith Dee talks with family business & wealth consultant, Jeff Savlov of Blum & Savlov, LLP, about how entitlement, silence, and poor planning can derail succession. Jeff shares his personal story and practical tips to help business owners avoid conflict and protect both their legacy and family relationships.
 
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 Emotions Can Derail Your Business Sale (And How to Stop It)

Selling a business isn’t just about numbers. For many owners, especially those nearing retirement, it can bring up unexpected emotions that impact decision making. In this episode of The Ins and Outs of Selling a Business™, Keith Dee of Osage Advisors talks about a challenge many sellers face but few discuss: emotional vulnerability. From uncertainty about life after the sale to pressure from family, these emotions can derail even the strongest deals if not addressed.
Keith shares what to expect and how to navigate it with the right support and preparation.Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w