The Ins and Outs of Selling a Business

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...

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 ...

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...

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...

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...

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 ...

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...

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...

Contact Keith: Osage Advisors...

The outlook for 2025 shows potential for growth in M&A activity, with optimism and capital available to support deals. Despite some challenges in 2024, such as interest rates and geopolitical factors, the market is anticipated to pick up this year. In today's episode of The Ins and Outs of Selling a Business as we break down the factors that shaped 2024 and discuss why experts believe 2025 will be a stronger year for business t...

Discover the latest insights into the business selling process with our new podcast segment, "This Week's Biggest Hurdle" part of our podcast series 'The Ins and Outs of Selling a Business'. In this episode, we discuss the complexities of due diligence and the importance of effective communication between buyers and sellers. As we navigate five active deals, we share real-world challenges and solutions that can impact your business...

Understanding the evolving buyer landscape is crucial for business owners in today’s market. From private equity firms to family offices, the variety of potential buyers has expanded significantly, offering both opportunities and challenges. In today's episode of 'The Ins and Outs of Selling a Business,' we discuss how this impacts lower middle-market companies and the importance of strategic preparation.

Contact Keith: Osage Adv...