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The Ins and Outs of Selling a Business
By Keith Dee, Osage AdvisorsBusiness
The Ins and Outs of Selling a Business episodes
- 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
860-767-3273
21 min - 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
860-767-3273
11 min - Customer Capital Explained: What It Is and Why Buyers Care
We’re back with Eric Lawton, CEO of Impact Financial Wealth Management, to continue our conversation on one of the most overlooked (but most powerful) drivers of business value: the intangibles.
In this episode, we dive deeper into the non-financial elements that can help maximize your sale price. We also explore another key driver of value: customer capital — the strength of your relationships with people outside the business, like clients, vendors, partners, and your broader community. These connections are a powerful part of what makes your company attractive to buyers.
Whether you're planning a sale soon or years down the line, understanding and showcasing your intangible assets can make all the difference.
Contact Keith: Osage Advisors, LLC
osageadvisors.com
860-767-3273
25 min - Turning Uncertainty Into Opportunity: Leading Through a Business Sale
Selling your business? You're not the only one feeling the pressure.
Stress, anxiety, fear of the unknown — these emotions are common for business owners during a sale. But one critical aspect often gets overlooked:
Your employees are feeling it too.Whether someone’s been with you for 2 years or 20, your team has built their lives around your business. To them, it’s more than a paycheck — it’s a second home. And when a sale is on the table, their future feels uncertain.
In this episode, we explore how owners can reduce fear, lead with empathy, and turn uncertainty into opportunity for their employees.
Contact Keith: Osage Advisors, LLC
osageadvisors.com
860-767-3273
10 min - What Buyers Really Pay For: The Role of Intellectual Capital in Valuation
What Really Drives Business Value? (Hint: It’s Not Just Revenue)
When business owners start planning for a sale, the focus usually lands on the numbers—revenue, margins, and profit growth. But there's another side of value that often gets overlooked… and it could make all the difference. In this episode, we’re joined by Eric Lawton, Founder & CEO of Impact Financial Wealth Management and an expert in exit planning, to explore the intangible drivers of business value. Whether you're years away from selling or already mapping out your exit, this conversation offers strategic insights that can significantly impact your outcome.
Contact Keith: Osage Advisors, LLC
osageadvisors.com
860-767-3273
23 min - From LOI to Close: The Hardest Part of Selling a Business
In this episode, we welcome back Rachel Fearnley, CEO of Dreamscapes Marketing + Design, for a candid conversation about life on the other side of the deal. After years of marketing for a winery, Rachel stepped into a whole new role—selling it.
She walks us through the unexpected twists that followed signing the Letter of Intent (LOI)—when she thought the hard part was over. Spoiler: it was just beginning.
From underestimated emotions to the complexities of due diligence, Rachel shares what surprised her most, what she wishes she knew sooner, and why clear communication (with a steady M&A advisor in the mix) was key to keeping the deal on track.
Whether you're a business owner considering a sale or just curious about what really happens behind the scenes, this episode is packed with honest insights and valuable lessons.
Contact Keith: Osage Advisors, LLC
osageadvisors.com
860-767-3273
20 min - The #1 Deal Killer in M&A: Financial Performance - And What to Do About it
In this episode, we dive into the top reason deals fall apart—declining or inconsistent financial performance.
Whether you're just starting the sale process or deep in negotiations, financial performance is always under the microscope. Buyers ask about your latest numbers right up to the closing table.
So what happens when a company starts missing its numbers mid-deal? Today we share a real example from a current engagement where the business’s performance dipped during due diligence—and how our team worked with both buyer and seller to find a solution that kept the deal alive.
Contact Keith: Osage Advisors, LLC
osageadvisors.com
860-767-3273
9 min - What It’s Really Like to Sell a Business: An Unexpected Seller Shares Her Story
In this episode, we sit down with Rachel Fearnley, CEO of dreamscapes marketing + design—and one of our longtime marketing partners—to talk about her unexpected journey from marketer to business seller.
dreamscapes had been working with Stonington Vineyards as their marketing agency when life took an unexpected turn. After the passing of one of the owners and the declining health of his wife, Rachel was asked to step in as President and Director of Operations to help stabilize the vineyard. What began as a marketing relationship quickly became something more, as Rachel found herself leading the business and ultimately responsible for guiding it through to new owners.
With the help of Osage Advisors, she navigated the emotional and strategic challenges of selling a company she’d come to care deeply about—offering a fresh, firsthand perspective on what it’s really like to go through the M&A process.
Contact Keith: Osage Advisors, LLC
osageadvisors.com
860-767-3273
21 min - Selling a Booming Business? Why an Interim CFO Might Be Your Best Move
In this episode, we take you inside a real deal: our client’s business is booming—revenues have doubled, and they’re weeks from going to market. But selling a company doesn’t pause day-to-day operations. That’s why we recommended bringing in an interim, part-time CFO to handle due diligence and keep the team focused on growth. If you're planning to sell while business is thriving, this video is for you.
Contact Keith: Osage Advisors, LLC
osageadvisors.com
860-767-3273
7 min - Turning People Into Power: How Teams Drive Growth
This week, we're welcoming back Alyssa Gelbard, Founder & CEO of Point Road Group, for a conversation that flips the script on business growth.
Alyssa shares a real-world example of a successful business with loyal clients and glowing satisfaction… yet they were struggling to generate new leads. The problem? Their team didn’t look or sound like the high-performing brand they truly were. From weak LinkedIn presence to generic messaging, the company wasn’t telling its full story—and it was costing them credibility with potential clients. Alyssa breaks down how she helped turn that around by strengthening employee profiles, improving how the team communicated their value and aligning internal voices with the company’s real impact.
If your team isn’t clearly reflecting what makes your business exceptional, this episode is a must-watch!
Contact Keith: Osage Advisors, LLC
osageadvisors.com
860-767-3273
22 min
About The Ins and Outs of Selling a Business
From the publisher's feed
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.
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