The Ins and Outs of Selling a Business

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 can spee...

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.    Contact Keith: Osage...

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 transition....

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...

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. If yo...

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 f...

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 som...

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 rol...

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...

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,...

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...

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 CO...

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 se...

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 adviso...

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-w...

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 wi...

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...

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 ex...

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 b...

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 exampl...

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, Rach...

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 fo...

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 w...

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 business...

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. Alyssa s...