The Ins and Outs of Selling a Business
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.
Episodes
You have a deal on the table, but can the buyer actually close?
In this episode of The Ins and Outs of Selling a Business™, Keith Dee explains why certainty of close is one of the most overlooked and critical factors in any transaction. From private equity firms to independent sponsors, not every buyer has the capital or structure to get a deal done.
Learn how to spot red flags, evaluate fi...
Selling your business is not just a financial transaction. It is a mental and emotional one that can impact every decision you make along the way.
In this episode of The Ins and Outs of Selling a Business™, Keith Dee sits down with mental performance coach Lauren Johnson, who has worked with elite athletes, executives, and high performers under pressure. Together, they break down how mindset, preparation...
Selling your business is not as simple as taking a call from a buyer. In many cases, it can lead to wasted time, lost value, and deals that fall apart.
In this episode of The Ins and Outs of Selling a Business™, Keith Dee shares real examples of what can go wrong when owners engage buyers without proper preparation. From lowball offers to failed deals and costly due diligence, these situations are more c...
In this episode, we continue our conversation with Ellen Palmer on the often overlooked human side of selling a business.
As deals move forward, misalignment with family members, partners, or key employees can create stress and put the transaction at risk. We discuss why early communication, stakeholder alignment, and honest conversations are essential to keeping deals on track.
As a business owner, building a strong leadership team is critical, especially when preparing to sell your company. But what happens when the person you expected to take over isn’t ready, loses confidence, or creates complications during the sale process?
In this episode of The Ins and Outs of Selling a Business™, Keith Dee discusses a common challenge sellers face when their chosen successor becomes par...
Selling a business is not just a financial transaction. It is also a deeply personal and emotional journey for founders and their families.
In this episode of The Ins and Outs of Selling a Business™, Keith Dee sits down with life coach Ellen Palmer to discuss why emotional preparedness plays a critical role in the sale process. They explore how stress, identity, and sustained pressure can affect decision...
You’ve signed the Letter of Intent, but the deal is far from done. In this episode, Keith Dee of Osage Advisors explains why the 60 to 90 days after an LOI are the most critical stage of a sale. As due diligence intensifies, buyers dig deeper into your financials, legal documents, customers, and operations.
This is where mindset becomes key. Sellers must shift from protective owner to committed closer, e...
When it comes to succession planning, the biggest challenges aren’t always financial—they’re emotional. In this episode of The Ins and Outs of Selling a Business™, Keith Dee continues his conversation with Jeff Savlov, a family business consultant and therapist who helps owners navigate the complex emotional and relational dynamics of passing a business to the next generation.
From entitlement issues and...
Is Now a Good Time to Sell Your Business? Here's What We're Seeing
"How's the market?" It’s the question we’re hearing from nearly every business owner right now.
In this episode of The Ins and Outs of Selling a Business™, Keith Dee, President of Osage Advisors, shares why 2026 could be a strong year for M&A. With plenty of capital on the sidelines and renewed interest from both private...
What happens when your children don’t want your business, or worse, expect to inherit it without paying?
In this episode of The Ins and Outs of Selling a Business™, Keith Dee talks with family business & wealth consultant, Jeff Savlov of Blum & Savlov, LLP, about how entitlement, silence, and poor planning can derail succession. Jeff shares his personal story and practical tips to help business o...
Selling a business isn’t just about numbers. For many owners, especially those nearing retirement, it can bring up unexpected emotions that impact decision making. In this episode of The Ins and Outs of Selling a Business™, Keith Dee of Osage Advisors talks about a challenge many sellers face but few discuss: emotional vulnerability. From uncertainty about life after the sale to pressure from family, these emotions ca...
In this episode of The Ins and Outs of Selling a Business™, Keith Dee of Osage Advisors is joined by Philip FitzGerald of Amplify Consulting Services to talk about what many sellers don’t see coming… the intensity of due diligence after a letter of intent is signed.
We cover why today’s buyers demand so much more information, how private equity firms and their consultants operate, and why sellers need to...
How Much Should You Share Before the LOI?
In this episode, we cover a key question in the M&A process: what information should you share with buyers before a Letter of Intent is signed?
Keith Dee of Osage Advisors explains how to balance transparency with confidentiality, what goes into a CIM, and why today’s buyers often ask for more upfront. We also share how the right info early on c...
Thinking about selling your business? Don’t guess your company’s value.
In this episode, Keith Dee from Osage Advisors sits down with Philip Fitzgerald of Amplified Consulting Group to break down M&A prep for first-time sellers and family-owned businesses. Learn the real steps to understand your business’s worth, avoid common mistakes, and get the most out of your exit.
Selling a Family Business? What If the Next Generation Gets Cold Feet?
In this episode, we explore what happens when your family isn’t fully on board with your decision to sell. From hesitation to outright resistance, these moments can derail a deal if not handled carefully.
Learn how to align your family, communicate your goals, and protect the value of your business through a smooth trans...
In this episode of The Ins and Outs of Selling a Business, Keith is joined by Jim Young and Philip Dee for a candid year-in-review of 2025’s most complex deals. Together, they unpack transactions that nearly fell apart, required creative structures, and demanded constant pivots to close.
From how special business designations impact valuation to earn-outs, seller notes, operational challenges, and deals ...
In this episode, we break down seller notes, one of the most common (and misunderstood) tools in M&A deal structuring.
We explain what seller notes are, why buyers love them, and how sellers can actually benefit from offering financing as part of the deal. From increasing your sale price to helping a deal cross the finish line, seller notes can be a powerful tool when used the right way.
This year has been an interesting one in the world of M&A. In this special year-end episode, we’re bringing together members of the Osage team to reflect on the deals, trends, and lessons that defined 2025.
Our guests, Philip Dee (Senior Associate, Business Development) and Jim Young (Managing Director), join us to share what they saw in the market, how we helped clients get deals across the finish line, and what business owner...
Already Have a Buyer? Here’s Why You Still Need an M&A Advisor
In this episode, we talk about what happens when a buyer approaches you directly, and why bringing in an M&A advisor is still critical. From deal structure and negotiation to protecting your interests and creating leverage, there’s a lot more to closing a deal than just finding a buyer.
If you're thinking, “I’ve already ...
In this episode, we continue the conversation sparked by one of the best questions we've ever been asked: "When should I expect the unexpected?" The answer: at every stage of the process.
We dig deeper into what surprises really look like during a business sale, from hidden issues to buyer behavior shifts to personality clashes. No matter how experienced you are, something always comes up.
...
Popular Podcasts
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com
When a group of women from all over the country realise they all dated the same prolific romance scammer they vow to bring him to justice. In this brand new season of global number 1 hit podcast, The Girlfriends, Anna Sinfield meets a group of funny, feisty, determined women who all had the misfortune of dating a mysterious man named Derek Alldred. Trust Me Babe is a story about the protective forces of gossip, gut instinct, and trusting your besties and the group of women who took matters into their own hands to take down a fraudster when no one else would listen. If you’re affected by any of the themes in this show, our charity partners NO MORE have available resources at https://www.nomore.org. To learn more about romance scams, and to access specialised support, visit https://fightcybercrime.org/ The Girlfriends: Trust Me Babe is produced by Novel for iHeartPodcasts. For more from Novel, visit https://novel.audio/. You can listen to new episodes of The Girlfriends: Trust Me Babe completely ad-free and 1 week early with an iHeart True Crime+ subscription, available exclusively on Apple Podcasts. Open your Apple Podcasts app, search for “iHeart True Crime+, and subscribe today!
The official podcast of comedian Joe Rogan.
The World's Most Dangerous Morning Show, The Breakfast Club, With DJ Envy, Jess Hilarious, And Charlamagne Tha God!