The Ins and Outs of Selling a Business

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
kdee@osageadvisors.com
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
kdee@osageadvisors.com
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
kdee@osageadvisors.com
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
kdee@osageadvisors.com
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
kdee@osageadvisors.com
860-767-3273
 

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 focus on the end game.So when your deal hits a wall (and it will), remember: setbacks are temporary. The right team keeps things moving.

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 owners can leave a lasting impact while maximizing their company's value.
Contact Keith: Osage Advisors, LLC
osageadvisors.com
kdee@osageadvisors.com
860-767-3273

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@osageadvisors.com
860-767-3273

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 sustainable company that thrives beyond their direct involvement.
Contact Keith: Osage Advisors, LLC
osageadvisors.com
kdee@osageadvisors.com
860-767-3273

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@osageadvisors.com
860-767-3273