When a family sells a business, the hardest part isn’t always the numbers. It’s navigating the relationships, expectations, and emotions that come with it.

In this episode of The Ins and Outs of Selling a Business™, Keith Dee is joined by his son, Philip Dee, to discuss the family dynamics that can make or break a transaction. Drawing from their experience advising family owned businesses, they explore the importance of communication, choosing the right buyer, protecting a company’s legacy, and creating opportunities for the next generation.

If you own a family business and are considering a future sale or transition, this episode offers practical insights into why talking early and talking often can help set the stage for a successful transaction.

Contact Keith: Osage Advisors, LLC

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Who is handling the financial side of your business when it’s time to sell?

In this episode of The Ins and Outs of Selling a Business™, Keith Dee explains why having the right financial support can be critical during an M&A transaction, especially for closely held businesses without a CFO. He discusses the role of your CPA, when a fractional CFO or sell side quality of earnings report may help, and why timely, accurate financial reporting matters during due diligence.

If you’re preparing to sell your business, this episode highlights how building the right financial team can help keep the process moving and avoid unnecessary delays.

Contact Keith: Osage Advisors, LLC

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What does it take to build a business that lasts 25 years?

In Part 2 of this special anniversary episode of The Ins and Outs of Selling a Business™, Keith Dee reflects on the challenges, pivotal decisions, and lessons that shaped Osage Advisors. From navigating the Great Recession and the pandemic to investing in technology, growing the team, and launching this podcast, Keith shares how Osage evolved while staying focused on one thing: putting clients first.

Keith also looks ahead to the next chapter of Osage and reflects on the clients, team, referral partners, and family who helped make the past 25 years possible.

Contact Keith: Osage Advisors, LLC

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When selling your business, how do you know you’re getting the best possible deal?

In this episode of The Ins and Outs of Selling a Business™, Keith Dee shares real world examples of business owners who received dramatically different offers for the same company. He explains why negotiating with a single buyer can leave significant value on the table and how a competitive sales process can uncover what your business is truly worth.

You only get one chance to sell your business. This episode highlights why testing the market and having experienced representation can make all the difference.

Contact Keith: Osage Advisors, LLC

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Twenty five years ago, Keith Dee founded Osage Advisors with no clients, two young children at home, and a vision to provide business owners with a better way to sell their companies.

In Part 1 of this special 25th anniversary episode of The Ins and Outs of Selling a Business™, Keith reflects on the early days of Osage, the lessons that shaped the firm, and why trust, transparency, and understanding an owner's goals remain at the heart of every transaction.

Join Keith as he looks back on 25 years of helping business owners navigate one of the biggest decisions of their lives, and stay tuned for Part 2.

Contact Keith: Osage Advisors, LLC

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Even when an M&A deal is progressing smoothly, unexpected issues can surface at any time.

In this episode of The Ins and Outs of Selling a Business™, Keith Dee shares a real world example of a buyer raising concerns over customer concentration late in the due diligence process. He explains how the proposed deal terms could have negatively impacted the seller and how strategic negotiation helped both sides reach a more equitable solution.

If you're considering selling your business, this episode highlights why experienced representation can be critical when unexpected hurdles, retrades, and last minute negotiations arise.

Contact Keith: Osage Advisors, LLC

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AI is no longer just a competitive advantage. It's becoming a key factor in how businesses are valued.

In Part 2 of this conversation, Keith Dee sits down again with Brandon Powell, CEO of HatchWorks AI, to discuss how business owners can move beyond AI experimentation and build a practical strategy that drives growth. They explore AI governance, protecting company data, preparing your team for adoption, and why private equity firms are increasingly evaluating AI readiness during the acquisition process.

Whether you're planning to sell your business or simply want to stay competitive, this episode offers practical insights on implementing AI, increasing operational efficiency, and positioning your company for long term value.

Contact Keith: Osage Advisors, LLC

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Is now a good time to sell your business?

In this episode of The Ins and Outs of Selling a Business™, Keith Dee shares an inside look at today's M&A market and why buyer demand remains strong despite recent economic and geopolitical uncertainty. He explains what's driving activity from private equity firms and strategic buyers, why competition for quality businesses is increasing, and what business owners should be doing now to prepare for a successful sale.

If you're considering selling your business, this episode offers timely insights into the current market and how to position yourself to maximize value.

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AI is everywhere, but how do business owners separate real opportunities from the hype?

In this episode of The Ins and Outs of Selling a Business™, Keith Dee sits down with Brandon Powell, CEO of HatchWorks AI, to discuss how companies can build an effective AI strategy that delivers measurable results. They explore common mistakes businesses make when adopting AI, how to identify high impact use cases, why data matters, and where AI can create the greatest return on investment.

Whether you're looking to improve operations, increase productivity, or build a more valuable business, this episode offers practical insights into using AI to drive long term growth.

What should you do when a buyer contacts you directly about purchasing your business?

In this episode of The Ins and Outs of Selling a Business™, Keith Dee explains why unsolicited offers from strategic buyers and private equity firms aren't always what they seem. He shares real world examples of business owners who negotiated one on one with buyers, the risks of skipping a competitive sales process, and why testing the market is critical to maximizing value.

If you're considering selling your business or have received an unexpected offer, this episode offers practical insights to help you make the right decision before moving forward.