The Ins and Outs of Selling a Business

Hosted by Keith Dee, Osage Advisors

Business

Website RSS feed

Episodes

100

Latest episode

Aug 2026

Language

About the show

This podcast taps the expertise of Keith Dee, President and CEO of Osage Advisors, with more than 30 years of experience advising business owners and families of midsize companies and helping them maximize value through M&A and capital transactions.

Listen to episodes

60 recent

September 10, 2026Episode 14519 min

What It Really Takes to Build a Successful M&A Firm Over 25 Years

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 osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

September 3, 2026Episode 1446 min

Before You Accept an Offer for Your Business, Listen to This!

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 osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

August 27, 2026Episode 14316 min

It Took 25 Years to Build This M&A Firm — Here’s What We Learned!

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 osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

August 20, 2026Episode 1428 min

How Unexpected Surprised Can Kill a Business Sale

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 osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

August 6, 2026Episode 14123 min

The Right Way to use AI in a Business Sale

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 osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

July 30, 2026Episode 1407 min

While Everyone Hesitates, You Close the Deal.

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. Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

July 23, 2026Episode 13925 min

Can AI Be Trusted With the Biggest Sale of Your Life?

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. Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

July 16, 2026Episode 13810 min

The Business Valuation Mistake No One Talks About

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. Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

July 9, 2026Episode 13726 min

The AI Advantage Sellers Can't Afford to Ignore

AI is changing the way businesses compete, and buyers are paying attention. In Part 2 of this conversation, Keith Dee sits down again with Mark Emmer, President of Optimize, Inc., to discuss how AI, strategic planning, and operational discipline can increase business value. They explore practical ways companies can adopt AI, improve processes, and build the kind of growth strategy buyers are looking for in today's M&A market. Whether you're planning to sell in the near future or simply want to build a stronger business, this episode offers valuable insights on using AI and strategic planning to position your company for long-term success. Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

July 2, 2026Episode 1368 min

One Unexpected Event Can Cost You Millions

What does it mean when everyone in an M&A deal says, "Pens down"? In this episode of The Ins and Outs of Selling a Business™, Keith Dee explains one of the most common moments of tension during a business sale: when negotiations temporarily come to a halt. He discusses why deals pause, the business issues that typically cause delays, and why the best solutions often come from conversations between buyers and sellers, not battles between attorneys. If you're preparing to sell your business, this episode offers practical insight into navigating deal roadblocks, resolving negotiations, and keeping your transaction moving toward a successful closing. Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w