The Ins and Outs of Selling a Business

Hosted by Keith Dee, Osage Advisors

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Episodes

100

Latest episode

Oct 2026

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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.

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60 recent

November 5, 2026Episode 1509 min

The Power of Patience: Why Waiting Could Maximize Your Business Sale

When is the right time to sell your business, and could waiting actually increase its value? In this episode of The Ins and Outs of Selling a Business™, Keith Dee explains why selling sooner isn't always the best decision. Drawing from real conversations with business owners, he shares examples of companies that could benefit from waiting to demonstrate stronger growth, improve financial reporting, or build a more compelling story for potential buyers. If you're considering selling your business, this episode highlights why timing, preparation, and patience can make a significant difference in maximizing value and achieving a successful sale. Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

October 15, 2026Episode 14923 min

Father and Son in Business: Navigating Family Dynamics and Succession

What is it really like to work alongside your father or son in a family business? In Part 2 of this special episode of The Ins and Outs of Selling a Business™, Keith Dee and his son, Philip Dee, share a personal look at their experience working together at Osage Advisors. They discuss navigating generational differences, balancing family relationships with business decisions, and preparing the next generation to take on a greater leadership role. Whether you're working alongside family or planning for the future of your business, this episode offers valuable insights into the importance of communication, mutual respect, and building a legacy that lasts. Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

October 8, 2026Episode 1487 min

Before You Announce the Sale: What Every Business Owner Should Know

One of the biggest concerns business owners have when selling their company is confidentiality. How do you protect sensitive information while finding the right buyer? In this episode of The Ins and Outs of Selling a Business™, Keith Dee explains how confidentiality is maintained throughout the M&A process, from approaching potential buyers to deciding when to inform key employees and customers. He discusses the importance of confidentiality agreements, controlling the flow of information, and navigating these sensitive conversations at the right time. If you're considering selling your business, this episode offers practical insights into protecting your company, your relationships, and your peace of mind throughout the sale process. Contact Keith: Osage Advisors, LLC osageadvisors.com kdee@osageadvisors.com 860-767-3273 ✦︎ Subscribe to our YouTube channel! https://www.youtube.com/channel/UCtjPAHGcQhOfm7HfLAMVy8w

October 1, 2026Episode 14726 min

Selling the Family Business: When Legacy, Money & Emotions Collide in an M&A Deal

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

September 24, 2026Episode 1465 min

Selling Your Business? You May Need More Than an Accountant

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

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