Osage Advisors, LLC

Osage Advisors, LLC Osage Advisors. Boutique Investment Bank. Selling a business is much more than a financial transaction – it is a very personal matter.

Making the decision to sell the business that you worked so hard to build is a major life decision, and our team approaches every opportunity with great care and concern. Our goal is always to bring you the best value when we sell your company, and this means more than just the best price. It also means finding a buyer who will be the right fit for your employees and customers, so that the busines

s you built can continue its success. We work hard to guide you through every step of the process to ensure a great experience and the results you desire.

06/23/2026

You’ve found the right buyer, agreed on value, and are ready to move forward. Then comes one more request: they want you to stay longer than expected.

In our latest episode of The Ins and Outs of Selling a Business™, Keith Dee discusses one of the most common challenges sellers face during negotiations: extending their post-closing transition period. While it may feel like a setback at first, today’s technology and flexible work environments can make these arrangements far more manageable than many owners expect. The key is understanding how to structure a transition that works for both you and the buyer.

Watch the full episode to learn how to navigate transition requests without putting your future plans on hold.

Watch the full episode here: https://youtu.be/1hxyMSUEINU��

Listen here: https://www.podbean.com/eas/pb-c9hyf-1af1036

06/18/2026

What happens when the right buyer wants you to stay with the business longer than you planned?

In this episode of The Ins and Outs of Selling a Business™, Keith Dee discusses one of the most common challenges business owners face during negotiations: extending their post-closing transition period. He explains why buyers often require sellers to stay involved longer, how that request impacts deal structure, and why it doesn't necessarily mean giving up the lifestyle you've worked so hard to create.

If you're considering selling your business, this episode offers practical insight into balancing your personal goals with what buyers need to complete a successful transaction.

Watch the full episode here: https://youtu.be/1hxyMSUEINU��

Listen here: https://www.podbean.com/eas/pb-c9hyf-1af1036

Most business owners spend years preparing their company for sale. Few spend time preparing themselves.In our latest blo...
06/17/2026

Most business owners spend years preparing their company for sale. Few spend time preparing themselves.

In our latest blog post, we explore one of the most overlooked challenges in the sale process: the emotional side of letting go. Beyond valuation, negotiations, and due diligence lies a deeper question many owners eventually face: Who am I without this business?

Read the full article to learn how self-doubt, pressure, and identity can influence the outcome of a sale just as much as the numbers: https://osageadvisors.com/news-event/the-hardest-part-of-selling-your-business-isnt-the-deal/

06/16/2026

When selling a business, one of the most valuable assets often walks out the door every evening: your people and their knowledge.

In Part 2 of this conversation, Keith Dee sits down again with Ken Winell, Co-CEO of Nexus Digital Group, to discuss how AI can help businesses preserve institutional knowledge, support smoother transitions, and recognize the employees who helped build the company's success.

Because a successful exit isn't just about transferring ownership. It's about protecting the legacy and expertise that got you there.

Watch the full episode to learn how AI is reshaping business transitions and creating value beyond the balance sheet.

Watch the full episode here: https://youtu.be/JOFLrxqY_2A��

Listen here: https://www.podbean.com/eas/pb-8mxh4-1ae7a94

06/11/2026

Selling a business today requires more than strong financial performance. Buyers are increasingly evaluating how companies use technology, preserve institutional knowledge, and prepare for the future.

In Part 2 of this conversation, Keith Dee sits down again with Ken Winell, Co-CEO of Nexus Digital Group, to discuss how AI can help businesses capture employee expertise, improve onboarding and training, modernize legacy systems, and enhance value during the sale process. They also explore why every business should have an AI policy and how owners can take practical steps to stay ahead as technology continues to evolve.

If you're planning to sell your business in the coming years, this episode offers valuable insight into how AI can strengthen your company and support a successful transition.

Watch the full episode here: https://youtu.be/JOFLrxqY_2A��

Listen here: https://www.podbean.com/eas/pb-8mxh4-1ae7a94

06/09/2026

Earnouts have become one of the most common tools for getting deals across the finish line in today’s M&A market.

While many sellers are hesitant at first, a properly structured earnout can help bridge valuation gaps and create a path toward achieving the outcome you're looking for. The key is understanding how they're built and ensuring the right protections are in place.

Watch our latest episode to learn how earnouts work and why they may play a role in your transaction.

Watch the full episode here: https://youtu.be/vABVxWqB8G8��

Listen here: https://www.podbean.com/eas/pb-2gtua-1adef84

06/04/2026

Selling a business often comes down to one challenge: bridging the valuation gap between buyer and seller.

In this episode of The Ins and Outs of Selling a Business™, Keith Dee discusses earnouts and why they have become a common tool in today’s M&A market.

Keith explains how earnouts work, why buyers use them to reduce risk, and how sellers can structure them properly to protect their interests. If you're considering selling your business, this episode provides practical insight into one of the most important deal terms you may encounter.

Watch the full episode here: https://youtu.be/vABVxWqB8G8��

Listen here: https://www.podbean.com/eas/pb-2gtua-1adef84

06/02/2026

AI is becoming an important part of the business sale conversation.

In this episode of The Ins and Outs of Selling a Business™, Keith Dee sits down with Ken Winell, Co-CEO of Nexus Digital Group, to discuss how AI is influencing due diligence, operations, and business value. As buyers take a closer look at how companies are using AI, preparation matters more than ever.

Watch the full episode to learn why AI readiness could impact your next transaction.

Watch the full episode here: https://youtu.be/Hqh0BkP4bo0��

Listen here: https://www.podbean.com/eas/pb-gx5zq-1ad5d34

05/28/2026

Selling a business in today’s market is no longer just about financial performance. Buyers are now asking a new question: “How is your company using AI?”

In this episode of The Ins and Outs of Selling a Business™, Keith Dee sits down with Ken Winell, Co-CEO of Nexus Digital Group, to discuss how artificial intelligence is changing the way businesses are evaluated, operated, and valued.

They explore how business owners can prepare for AI-related due diligence, why having an AI policy matters, and how companies are using AI to improve efficiency, supply chain management, HR, marketing, and competitive strategy. If you’re thinking about selling your business, this episode explains why AI readiness could directly impact your valuation.

Watch the full episode here: https://youtu.be/Hqh0BkP4bo0��

Listen here: https://www.podbean.com/eas/pb-gx5zq-1ad5d34

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