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…

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…

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—a…

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 exp…

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 clie…

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…

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 …

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 g…

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 p…

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 Advisor…

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 …

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 abo…

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 ca…

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…

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 act…

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-mar…

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…

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…

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…

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, recurri…

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 Bu…

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, an…

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 episod…

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…

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 remors…

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 marke…

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…

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 …

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 wh…

Discover the real-life stories and essential strategies behind successful business exits in today's episode of 'The Ins and Outs of Selling a Business'. Join us as we dive deep into the complexities of exit planning with our guest, Denis Horrigan. From balancing personal and professional life to navigating family dynamics and market changes, learn …

In today's episode of 'The Ins and Outs of Selling a Business' with Denis Horrigan, we discuss the compelling analogy between navigating with old maps and the process of selling a business. Discover the importance of thorough planning and counseling for business owners, ensuring a smoother transition and achievement of desired goals. Tune in as we …

Discover the essential elements of creating a thriving business culture. From understanding the importance of addressing complaints within your organization to the critical interplay between business systems and human systems. Join us in today's episode of the 'Ins and Outs of Selling a Business' as we explore the vital role of culture in preparing…

Understand the importance of creating a culture, gaining buy-in from the team, and executing strategic plans. In today's episode of 'The Ins and Outs of Selling a Business' with Brent Robertson, we explore the parallels between coaching a team and running a business. Learn how to elevate team performance and create conditions for success in any cir…

In today's episode of 'The Ins and Outs of Selling a Business,' we bring back Geri Fitapelli, a seasoned business valuation and real estate expert to share insights from her journey of building a national firm, Valbridge. Discover the challenges and successes along with the importance of finding the right fit in business partnerships, and how unexp…

Look closely at factors that influence your company's worth, from technological shifts to market uncertainties. Demystify the reasons why knowing a company's value is crucial, especially for small businesses. Join us in today's episode of the Ins and Outs of Selling a Business with Osage team member Geri Fitapelli as we share practical perspectives…

From valuation surprises to navigating emotional hurdles, discover the intricate strategies that led to a doubling of the purchase price. Unlock the secrets of business selling and join us in our latest episode of 'The Ins and Outs of Selling a Business' as we unravel the journey of turning a lowball offer into a jackpot deal. Gain invaluable insig…

Assembling the puzzle of a successful business sale involves more than financial reports. In today's episode of the 'Ins and Outs of Selling a Business', discover the often overlooked key piece that brings creativity, energy, and diverse expertise to your operation that drives growth and profitability. Contact Keith: Osage Advisors, LLC osageadviso…

In today's episode of the Ins and Outs of Selling a Business, we bring back Richard Austin of Integrated Partners to discuss expert advice on tax implications and estate planning. Transform your financial future and delve into the intricate world of tax planning and business succession. Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osag…

Unlock the secrets to business exits and dive into the intricacies of successful transactions, strategic planning, and pitfalls to avoid. Join us in today's episode of 'The Ins and Outs of Selling a Business' with Richard Austin of Integrated Partners for valuable insights and expert guidance on your entrepreneurial journey. Contact Keith: Osage Ad…

Several factors, ranging from interest rates to supply chain disruptions, significantly affect M&A deal flow and most sellers and buyers adapt to these changes. In today's episode of 'Ins and Outs of Selling a Business' we delve into the complexities of the market in 2023, offering insights and predictions for 2024. Contact Keith: Osage Advisors, L…

How does fishing relate to selling your business? It's important for sellers to be prepared and not get distracted by the shiny object. In today's episode of 'Ins and Outs of Selling a Business' We explore why you should be prepared if you are looking to sell your business and why you owe it to yourself and your business to test the market. Contact…

Realizing the maximum value of your business during a possible sale or acquisition heavily relies on unlocking the secrets to sustained business growth. In today's episode of 'The Ins and Outs of Selling a Business' with Joe Grace of Chief Outsiders, we explore how their CMO fractional consulting firm helps businesses implement effective strategies…

Unlock the keys to a successful business transaction by harnessing the power of growth. In today's episode of The Ins and Outs of Selling a Business, we dive into the world of strategic expansion, where every step fuels your business' value. Contact Keith: Osage Advisors, LLC osageadvisors.com [email protected] 860-767-3273…

Discover the realm of business transactions, where we serve as intermediaries and advisors, skillfully managing owner concerns and bridging gaps between buyers. In this episode, through meaningful dialogue and problem-solving, we strive to align the perfect buyer who matches the ideal fit, price, and value, leveraging our wealth of experience to en…

Discover the untapped potential of harnessing a Part-Time CFO's expertise to enhance the value of your business when navigating the selling process. In this episode, through comprehensive financial analysis and invaluable insights, these skilled CFOs empower business owners to make well-informed decisions, guaranteeing their full understanding and …

Discover the potential of targeted non-qualified compensation programs, surpassing 401k limitations to retain invaluable key employees. In this episode, we delve into how businesses can strategically leverage these targeted programs to recognize the genuine worth and profound impact of their vital talent on organizational success. Contact Keith: Os…

Sometimes, raising prices to improve margins can backfire as potential buyers associate it with lower unit sales. ⁠⁠In this episode, learn from our client's experience and the airline industry's strategy to maximize profitability. ⁠ Contact Keith: Osage Advisors, LLC osageadvisors.com [email protected] 860-767-3273…

Discover the importance of sustainable competitive advantage in today's business landscape! In this episode, Keith Dee explores the key factors behind declining margins and the significance of pricing strategies. Contact Keith: Osage Advisors, LLC osageadvisors.com [email protected] 860-767-3273…

As a business owner, what are the techniques and strategies that can help you exit your business on your terms? In this episode, Keith Dee explores the immense value and improved lifestyle outcomes that come with a well-planned exit. Contact Keith: Osage Advisors, LLC osageadvisors.com [email protected] 860-767-3273…

Contact Keith: Osage Advisors, LLC osageadvisors.com [email protected] 860-767-3273By Keith Dee, Osage Advisors