The Ins and Outs of Selling a Business

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

Sellers: Here’s Why Buyer Financing Matters Most

When a lender tries to change the deal structure to fit their needs, it can throw the whole transaction off track. But here’s the truth: it’s the buyer’s responsibility to solve lender problems - not the seller’s. In this video, Keith Dee of Osage Advisors explains: Why buyers must take ownership of lender approval How sellers should monitor buyer financing week by week The risks of involving a seller note in lender negotiations Why a buyer’s track record with lenders matters in getting deals closed As the seller’s representative, Osage keeps a close eye on how buyers are financing their deals because funding issues can kill a transaction fast. If you’re a business owner thinking about selling, or a buyer preparing to acquire, this advice could make or break your deal. Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w 🎤 Listen to the Podcast https://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.

Why Every Detail of Your Deal Structure Matters

In the M&A world, we always say “the devil is in the details” and that could not be more true when it comes to deal structure. Today’s due diligence process is more detailed than ever. It can feel overwhelming, but the fine points are where deals succeed or fall apart. In this episode, we explore how the structure of your transaction plays directly into the details that buyers and their advisors are carefully reviewing. If you are planning to sell your business or support someone who is, this conversation will help you better understand what it takes to get the deal across the finish line.
Contact Keith: Osage Advisors, LLC
osageadvisors.com
kdee@osageadvisors.com
860-767-3273

Why Buyers Back Out Before the Deal Closes — And What You Can Do About It

Selling your business is a massive undertaking — emotionally, mentally, and logistically. You’ve spent a career building something valuable, and now you’re shifting gears, pitching that value to potential buyers and navigating complex conversations about your company’s future.
But what happens when serious buyers walk away… even before a Letter of Intent is signed?
In this episode, we share real-world insights from our own experience with buyers backing out — what triggered it, how we handled it, and why it happens more often than you think. From shifting priorities to internal deal dynamics, these situations are frustrating but common.
Contact Keith: Osage Advisors, LLC
osageadvisors.com
kdee@osageadvisors.com
860-767-3273