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:

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

[email protected]

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

[email protected]

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

[email protected]

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

[email protected]

860-767-3273

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

[email protected]

860-767-3273

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

[email protected]

860-767-3273

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

[email protected]

860-767-3273

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, LLC

osageadvisors.com

[email protected]

860-767-3273

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 shares powerful insights on how your team represents your business both inside and outside your company walls — and why that matters, especially when you’re thinking about growth, leadership, or a future sale.

Whether you're grooming your company for acquisition or simply want to strengthen your brand from the inside out, this conversation will change the way you think about your people and the power of their personal brands.

Contact Keith: Osage Advisors, LLC

osageadvisors.com

[email protected]

860-767-3273