The Ins and Outs of Selling a Business

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 looki...

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 bet...

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 sha...

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 s...

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 trai...

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 interes...

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 explor...

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. Fro...

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...

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 imp...

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...

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 ye...

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 “play...

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...

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, prep...

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...

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 prepari...

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 beco...

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 d...

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 cl...

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 iss...

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...

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 bus...

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 fami...

In this episode of The Ins and Outs of Selling a Business™, Keith Dee of Osage Advisors is joined by Philip FitzGerald of Amplify Consulting Services to talk about what many sellers don’t see coming… the intensity of due diligence after a letter of intent is signed. We cover why today’s buyers demand so much more information, how private equity firms and their consultants operate, and why sellers...