The Ins and Outs of Selling a Business

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, c...

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....

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, LL...

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 ho...

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...

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 man...

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. Cont...

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...

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. C...

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 wil...

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 solu...

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 prep...

Relying on familiar buyers might seem easy, but it can limit your options and the value of your business. In today's episode of 'The Ins and Outs of Selling a Business,' together with our guest Peter Lehrman, we cover why sellers should explore the full market, what risks come with sticking to known buyers, and how to position your business for the best deal. Learn more about making informed decis...

In today’s episode of The Ins and Outs of Selling a Business we’re joined once again by Steven Nicokiris, a seasoned advisor and CPA with over 35 years of experience. We discuss key case studies, highlighting both successful and less-than-ideal outcomes to help guide business owners when making the critical decision to sell. Join us and learn about importance of choosing the right buyer and the va...

Selling a business is often unfamiliar and can cause anxiety, but having the right advisors in place can help ease the process. In our latest episode of 'The Ins and Outs of Selling a Business' with our guest Steven Nicokiris , we discuss the role of trusted advisors, especially CPAs, in preparing for a successful business sale. Join us as we share insights on the importance of building trust, und...

Explore the key characteristics private equity firms prioritize when evaluating potential acquisitions. Grasping these critical factors can significantly enhance a business's appeal to investors. In today's episode of The Ins and Outs of Selling a Business with our guest Jack McGlinn as we talk about the essential roles of management teams, recurring revenue, and customer concentration in driving...

Building a strong team is key to business growth, and finding the right talent infuses your organization with fresh energy and innovative ideas while unlocking access to new markets. Hear more about the importance of assembling a top team to expand your business reach and grow your top line in our latest episode of ‘The Ins and Outs of Selling a Business’ with our guest Jack McGlinn.  Contact Keit...

In today's episode of The Ins and Outs of Selling a Business, we recap the season's highlights and offer a glimpse into what's next in Season 4. Reflecting on the journey of three successful seasons, this episode wraps up season 3 by highlighting the value we have provided to business owners. It also covers insights gained, listener's feedbacks, and the importance of preparing not just for the bus...

In the first half of 2024, market activity has been slower than anticipated, especially for larger deals, due to high interest rates and reduced multiples. Despite significant capital available, deal volumes have dropped. Interestingly, smaller transactions remain steady and in demand, driven by private equity add-on acquisitions. In today's episode of 'The Ins and Outs of Selling a Business' we e...

Discover the emotional highs and lows of transitioning from business owner to retiree as we continue our conversation with our guest, Mark Rollins. Learn how Mark and his wife Jody reinvented their lives and founded a new business to help others navigate retirement in today's episode of 'The Ins and Outs of Selling a Business.' Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisor...

In today's episode of 'The Ins and Outs of Selling a Business,' we welcome back one of our first guests Markham Rollins to explore the emotional journey and strategic decisions behind selling a multi-generational business. We discuss the fears, uncertainties, and challenges faced during the process, offering insights into overcoming seller’s remorse, the importance of hiring an M&A advisor, an...

Discover the emotional journey of selling your business in our latest episode of 'The Ins and Outs of Selling a Business'. Join us as we delve into the critical decision-making process, uncovering the doubts, uncertainties, and fears that often accompany this significant step. From understanding the true value of your company to preparing for market entry, we explore essential strategies to naviga...

In today's episode of 'The Ins and Outs of Selling a Business' we delve deep into the emotional landscape of selling, navigating through doubts, uncertainties, and anxieties that arise during the process. From dealing with deal fatigue to understanding the importance of communication and assembling a supportive team, we explore strategies to ensure a successful outcome aligned with your goals and...

Discover the intricacies of sales processes and the importance of analytics in our latest episode of 'The Ins and Outs of Selling a Business' with our guest Jeff Clair. We talk about real-life examples and the vital role of tools like CRM systems. Gain valuable insights on setting goals, fostering accountability, and navigating the complexities of managing a sales team. Contact Keith: Osage Adviso...

Explore the critical aspects of sales strategy, pipeline management, and customer relationships that drive business success in today's episode of 'The Ins and Outs of Selling a Business' with our guest, Jeff Clair. From adjusting methodologies to market shifts, nurturing personal connections, and assessing key factors for potential buyers, learn why understanding your unique value proposition and...