The Ins and Outs of Selling a Business

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

July 24, 2025 10 mins

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...

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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...

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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 — ...

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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...

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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...

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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...

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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...

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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...

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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...

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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...

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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...

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April 3, 2025 7 mins
WHEN WILL THIS END? Ah, the question every dealmaker asks at some point. M&A deals will hit walls—unexpected delays, emotional sellers, nervous buyers, financing hiccups, diligence curveballs. It’s part of the process. But here’s the key: don’t panic. Don’t rush. Don’t lose sight of the goal. The best advisors don’t just close deals—they guide clients through the rough patches with strategy, calm, and a relentless...
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Legacy plays a crucial role in the sale of a business. Beyond valuation, owners must consider their company's brand, culture, and employees when transitioning to new ownership. In today's episode of 'The Ins and Outs of Selling a Business,' with Andrea Brown of Frequency 110 we discuss the importance of planning for leadership succession, retaining key employees, and ensuring a smooth transition. Join us as we explore how business ...

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March 20, 2025 8 mins

Navigating stay bonuses for key employees can be a critical part of the M&A process. Ensuring clear communication and early planning can help avoid internal conflicts that might impact the deal. In today's episode of 'The Ins and Outs of Selling a Business,' we discuss strategies for structuring stay bonuses and how they can influence a successful transaction.

Contact Keith: Osage Advisors, LLC

osageadvisors.com

kdee@osageadv...

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Shifting from working in your business to working on your business is key to scaling and building long-term value. Business owners often struggle with letting go, but developing a strategic mindset and empowering a strong leadership team can make all the difference. In today's episode of the Ins and Outs of Selling a Business, we're joined by our guest, Andrea Brown of Frequency 110, to explore how business owners can create a sust...

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Environmental issues can be a major hurdle in business transactions, especially for manufacturing companies. Delays in addressing concerns can extend closing dates, drive up costs, and complicate negotiations. In today's episode of 'The Ins and Outs of Selling a Business,' we discuss how environmental due diligence impacts deals and why proactive planning is key.

Contact Keith: Osage Advisors, LLC

osageadvisors.com

kdee@osageadvi...

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Successful business sales don’t end at the closing table—what happens next is just as important. Business owners need a clear strategy to manage their wealth, avoid seller’s remorse, and plan for long-term financial security. In today's episode of The Ins and Outs of Selling a Business with our guest Richard Dvorak of Discovery Point Wealth Advisors, we talk about post-sale transitions, wealth management, and the critical steps to ...

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Real estate plays a crucial role in business sales, and addressing it early can make all the difference. From lease agreements to sale options, sellers need to evaluate how real estate impacts their deal structure and financials. In today's episode of  The Ins and Outs of Selling a Business, we explore key strategies for handling real estate in M&A transactions to ensure a smooth closing.

Contact Keith: Osage Advisors, LLC

os...

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Successful business exits require planning, just like a great quarterback leads a team to the Super Bowl. Business owners need a clear strategy to maximize value, minimize taxes, and ensure a smooth transition. In today's episode of The Ins and Outs of Selling a Business with our guest Richard Devorak of Discovery Point Wealth Advisors, we talk about financial planning, tax considerations, and the key steps business owners should t...

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February 6, 2025 9 mins
When selling a business, it’s not just about making the sale; it’s about making the right sale. If market conditions aren't favorable, it may be wise to hold off and wait for better opportunities. In today's episode of 'The Ins and Outs of Selling a Business,' we explain why timing matters in M&A transactions and how waiting for the right moment can lead to better outcomes for your business.

Contact Keith: Osage Advisors...

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