The Ins and Outs of Selling a Business
This podcast taps the expertise of Keith Dee, President and CEO 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.
Episodes
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, e...
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...
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...
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 o...
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 ca...
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 need to...
How Much Should You Share Before the LOI?
In this episode, we cover a key question in the M&A process: what information should you share with buyers before a Letter of Intent is signed?
Keith Dee of Osage Advisors explains how to balance transparency with confidentiality, what goes into a CIM, and why today’s buyers often ask for more upfront. We also share how the right info early on c...
Thinking about selling your business? Don’t guess your company’s value.
In this episode, Keith Dee from Osage Advisors sits down with Philip Fitzgerald of Amplified Consulting Group to break down M&A prep for first-time sellers and family-owned businesses. Learn the real steps to understand your business’s worth, avoid common mistakes, and get the most out of your exit.
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 trans...
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 ...
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.
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 owner...
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 ...
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.
...
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, b...
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 sign...
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 mar...
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 ...
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 negotiatio...
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 rev...
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