The Ins and Outs of Selling a Business

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.

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

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.

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

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

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
kdee@osageadvisors.com
860-767-3273

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
kdee@osageadvisors.com
860-767-3273

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
kdee@osageadvisors.com
860-767-3273

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
kdee@osageadvisors.com
860-767-3273

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
kdee@osageadvisors.com
860-767-3273