The Ins and Outs of Selling a Business

Selling a Family Business: How to Get Everyone on Board

Selling a Family Business? What If the Next Generation Gets Cold Feet?
In this episode, we explore what happens when your family isn’t fully on board with your decision to sell. From hesitation to outright resistance, these moments can derail a deal if not handled carefully.
Learn how to align your family, communicate your goals, and protect the value of your business through a smooth 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

Deals That Almost Died: How We Sold Businesses No One Wanted to Buy

In this episode of The Ins and Outs of Selling a Business, Keith is joined by Jim Young and Philip Dee for a candid year-in-review of 2025’s most complex deals. Together, they unpack transactions that nearly fell apart, required creative structures, and demanded constant pivots to close.
From how special business designations impact valuation to earn-outs, seller notes, operational challenges, and deals that drew hundreds of buyers but only a few real contenders, this episode offers a behind-the-scenes look at what it really takes to get deals done.
 
Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

Seller Notes Explained: The Deal Structure Buyers LOVE, and Sellers Benefit From

In this episode, we break down seller notes, one of the most common (and misunderstood) tools in M&A deal structuring.
We explain what seller notes are, why buyers love them, and how sellers can actually benefit from offering financing as part of the deal. From increasing your sale price to helping a deal cross the finish line, seller notes can be a powerful tool when used the right way.
If you're preparing to sell your business or just want to understand what makes deals work, this episode is packed with insights on how to structure a win-win.
 
Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

M&A Year in Review: The Biggest Trends You Need to Know

This year has been an interesting one in the world of M&A. In this special year-end episode, we’re bringing together members of the Osage team to reflect on the deals, trends, and lessons that defined 2025.
Our guests, Philip Dee (Senior Associate, Business Development) and Jim Young (Managing Director), join us to share what they saw in the market, how we helped clients get deals across the finish line, and what business owners should be thinking about as we head into the new year.
Whether you're preparing to sell or just watching the market, this conversation is full of insights you don't want to miss.
 
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 M&A Firms Help you Sell Straight to the Buyer

Already Have a Buyer? Here’s Why You Still Need an M&A Advisor
In this episode, we talk about what happens when a buyer approaches you directly, and why bringing in an M&A advisor is still critical. From deal structure and negotiation to protecting your interests and creating leverage, there’s a lot more to closing a deal than just finding a buyer.
If you're thinking, “I’ve already got someone interested, do I really need help?” — this episode is for you.
 
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 Handle the Unknowns When Selling your Business

In this episode, we continue the conversation sparked by one of the best questions we've ever been asked: "When should I expect the unexpected?" The answer: at every stage of the process.
We dig deeper into what surprises really look like during a business sale, from hidden issues to buyer behavior shifts to personality clashes. No matter how experienced you are, something always comes up.
Our role is to help you manage those risks before they become roadblocks. You can't eliminate uncertainty, but you can reduce it. How you handle the unexpected often determines the outcome, both financially and personally.
 
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 Your Business? Here’s How to Beat Deal Fatigue

Selling a business isn’t just a financial process, it’s an emotional one. Long hours, constant pressure, and unexpected challenges can take their toll, leaving even the most prepared owners feeling drained and uncertain.
 
This emotional strain is what we call deal fatigue. It’s that point in the process when stress, doubt, and exhaustion start to creep in, and it can affect not just you, but your entire team.
 
In this episode, we explore what causes deal fatigue, how it shows up during the sale process, and the best way to navigate it: staying open, honest, and connected with your trusted advisors.
Watch now to learn how to manage deal fatigue and stay focused through every stage of selling your business.
 
Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

Before, During, and After the Deal — Expect the Unexpected

When a client asked us, “When should I expect the unexpected?” it was a rare question, but an important one. In this episode, we share how we guide new clients through the early stages of considering a sale, including understanding their goals and walking them through our process. We also break down the four key phases where surprises often show up: before going to market, during the sale process, after a deal is signed, and post-closing.
No matter how prepared you are, the unexpected is part of the journey. This episode will help you know what to expect and what you cannot plan for.Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

Thinking About Selling your Business? Don’t Miss This Market Update

In this episode, we break down what we’re seeing in today’s market, and why these uncertain times are raising real concerns for business owners thinking about selling.
From interest rate pressure and valuation gaps to buyer hesitation and lack of visibility, we explore the trends shaping the current deal landscape and the impact they’re having on timing.
Before deciding whether to go to market now or wait for conditions to shift, it is critical to take a close look at your business and your goals. The market will come back. The question is: are you ready when it does?
 
Contact Keith: Osage Advisors, LLCosageadvisors.com kdee@osageadvisors.com860-767-3273
✦︎Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w
🎤 Listen to the Podcasthttps://osageadvisors.com/podcasts/https://theinsandoutsofsellingabusiness.podbean.com
Keith is President 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. Over the course of his career, Keith was a partner of a CPA firm and ran several privately held businesses.

25 Years of Osage Advisors: What Business Success Really Takes

How do you define success? Milestones, profitability, legacy, and community all play a role, but the real story is often more complex. In this episode of The Ins and Outs of Selling a Business, Keith Dee reflects on his 25-year journey building Osage Advisors from a one-man startup into a trusted M&A advisory firm. From launching right before 9/11 and surviving market crashes, to navigating COVID and rebranding, Keith shares the risks, pivots, and perseverance it took to keep moving forward. For Keith, success isn’t just about numbers, it’s about resilience, relationships, and legacy. And after 25 years, Osage Advisors is just getting started.
Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w