The Ins and Outs of Selling a Business

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...

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...

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 peop...

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 — ...

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...

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 beginnin...

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...

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 Presiden...

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 Keit...

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 Lin...

We’ve been getting the same question over and over: “Should we be selling right now?”

The market is uncertain, and there’s no clear direction—but that doesn’t mean you should hit pause. In this video, we share why we’re advising most clients to stay the course, continue marketing, and monitor buyer activity.

There’s still capital on the sidelines—and real opportunities for well-positioned businesses.

Contact Keith: Osage Advisors...

As business owners, our brand is everything. It’s not just a logo or a tagline — it’s an extension of who we are. We pour years into building, refining, and protecting it. But there’s one critical piece that often gets overlooked: employee branding.

In this episode, we’re joined by Alyssa Gelbard, founder and CEO of Point Road Group — a leading expert in employee and executive branding. A...