The Ins and Outs of Selling a Business
Episodes
Why You Should NEVER Talk to a Buyer Without an Advisor
26 Mar 2026
Contributed by Lukas
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...
The Hidden Risk in Selling Your Business: Family and Team Conflict
19 Mar 2026
Contributed by Lukas
In this episode, we continue our conversation with Ellen Palmer on the often overlooked human side of selling a business. As deals move forward, misal...
What Happens When Your Chosen CEO Can't Lead After You Sell
12 Mar 2026
Contributed by Lukas
As a business owner, building a strong leadership team is critical, especially when preparing to sell your company. But what happens when the person y...
When Your Life’s Work Is for Sale: What Selling Your Business Really Feels Like
05 Mar 2026
Contributed by Lukas
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 ep...
60 Days to Close… Or Lose Everything
19 Feb 2026
Contributed by Lukas
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...
Can Your Kids Really Run the Business? What to Know Before You Hand It Over
12 Feb 2026
Contributed by Lukas
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 S...
Why 2026 Could Be the Best Year Yet to Exit Your Business
05 Feb 2026
Contributed by Lukas
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 ...
Selling the Family Business: Avoiding Drama, Conflict, and Hurt Feelings
30 Jan 2026
Contributed by Lukas
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 Sell...
How Emotions Can Derail Your Business Sale (And How to Stop It)
22 Jan 2026
Contributed by Lukas
Selling a business isn’t just about numbers. For many owners, especially those nearing retirement, it can bring up unexpected emotions that impact d...
How to Prepare for Buyer Demands After the LOI
15 Jan 2026
Contributed by Lukas
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 Service...
Selling Your Business? Don't Share THIS Before the LOI
08 Jan 2026
Contributed by Lukas
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 buye...
The $40M Myths That Almost Cost This Founder Everything
02 Jan 2026
Contributed by Lukas
Thinking about selling your business? Don’t guess your company’s value. In this episode, Keith Dee from Osage Advisors sits down with Philip Fitzg...
Selling a Family Business: How to Get Everyone on Board
26 Dec 2025
Contributed by Lukas
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 boar...
Deals That Almost Died: How We Sold Businesses No One Wanted to Buy
18 Dec 2025
Contributed by Lukas
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 co...
Seller Notes Explained: The Deal Structure Buyers LOVE, and Sellers Benefit From
11 Dec 2025
Contributed by Lukas
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 note...
M&A Year in Review: The Biggest Trends You Need to Know
04 Dec 2025
Contributed by Lukas
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 t...
How M&A Firms Help you Sell Straight to the Buyer
27 Nov 2025
Contributed by Lukas
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,...
How to Handle the Unknowns When Selling your Business
20 Nov 2025
Contributed by Lukas
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 a...
Selling Your Business? Here’s How to Beat Deal Fatigue
13 Nov 2025
Contributed by Lukas
Selling a business isn’t just a financial process, it’s an emotional one. Long hours, constant pressure, and unexpected challenges can take their ...
Before, During, and After the Deal — Expect the Unexpected
06 Nov 2025
Contributed by Lukas
When a client asked us, “When should I expect the unexpected?” it was a rare question, but an important one. In this episode, we share how we guid...
Thinking About Selling your Business? Don’t Miss This Market Update
09 Oct 2025
Contributed by Lukas
In this episode, we break down what we’re seeing in today’s market, and why these uncertain times are raising real concerns for business owners th...
25 Years of Osage Advisors: What Business Success Really Takes
03 Oct 2025
Contributed by Lukas
How do you define success? Milestones, profitability, legacy, and community all play a role, but the real story is often more complex. In this episo...
Sellers: Here’s Why Buyer Financing Matters Most
25 Sep 2025
Contributed by Lukas
When a lender tries to change the deal structure to fit their needs, it can throw the whole transaction off track. But here’s the truth: it’s the ...
Why Every Detail of Your Deal Structure Matters
18 Sep 2025
Contributed by Lukas
In the M&A world, we always say “the devil is in the details” and that could not be more true when it comes to deal structure. Today’s due ...
Why Buyers Back Out Before the Deal Closes — And What You Can Do About It
24 Jul 2025
Contributed by Lukas
Selling your business is a massive undertaking — emotionally, mentally, and logistically. You’ve spent a career building something valuable, and n...
Customer Capital Explained: What It Is and Why Buyers Care
17 Jul 2025
Contributed by Lukas
We’re back with Eric Lawton, CEO of Impact Financial Wealth Management, to continue our conversation on one of the most overlooked (but most powerfu...
Turning Uncertainty Into Opportunity: Leading Through a Business Sale
10 Jul 2025
Contributed by Lukas
Selling your business? You're not the only one feeling the pressure. Stress, anxiety, fear of the unknown — these emotions are common for business o...
What Buyers Really Pay For: The Role of Intellectual Capital in Valuation
03 Jul 2025
Contributed by Lukas
What Really Drives Business Value? (Hint: It’s Not Just Revenue) When business owners start planning for a sale, the focus usually lands on the numb...
From LOI to Close: The Hardest Part of Selling a Business
22 May 2025
Contributed by Lukas
In this episode, we welcome back Rachel Fearnley, CEO of Dreamscapes Marketing + Design, for a candid conversation about life on the other side of the...
The #1 Deal Killer in M&A: Financial Performance - And What to Do About it
15 May 2025
Contributed by Lukas
In this episode, we dive into the top reason deals fall apart—declining or inconsistent financial performance. Whether you're just starting the sale...
What It’s Really Like to Sell a Business: An Unexpected Seller Shares Her Story
08 May 2025
Contributed by Lukas
In this episode, we sit down with Rachel Fearnley, CEO of dreamscapes marketing + design—and one of our longtime marketing partners—to talk about ...
Selling a Booming Business? Why an Interim CFO Might Be Your Best Move
01 May 2025
Contributed by Lukas
In this episode, we take you inside a real deal: our client’s business is booming—revenues have doubled, and they’re weeks from going to market....
Turning People Into Power: How Teams Drive Growth
24 Apr 2025
Contributed by Lukas
This week, we're welcoming back Alyssa Gelbard, Founder & CEO of Point Road Group, for a conversation that flips the script on business growth. Al...
The Market is Uncertain, But Your Strategy Shouldn’t Be
17 Apr 2025
Contributed by Lukas
We’ve been getting the same question over and over: “Should we be selling right now?” The market is uncertain, and there’s no clear direction—...
The Secret Business Value that Everyone Ignores
10 Apr 2025
Contributed by Lukas
As business owners, our brand is everything. It’s not just a logo or a tagline — it’s an extension of who we are. We pour years into building, r...
The Never-Ending Deal
03 Apr 2025
Contributed by Lukas
WHEN WILL THIS END? Ah, the question every dealmaker asks at some point. M&A deals will hit walls—unexpected delays, emotional sell...
How Your Business Legacy Impacts Its Sale
27 Mar 2025
Contributed by Lukas
Legacy plays a crucial role in the sale of a business. Beyond valuation, owners must consider their company's brand, culture, and employees when trans...
How Stay Bonuses Keep Deals on Track
20 Mar 2025
Contributed by Lukas
Navigating stay bonuses for key employees can be a critical part of the M&A process. Ensuring clear communication and early planning can help avoi...
Why Owners Struggle to Step Back from Their Business
13 Mar 2025
Contributed by Lukas
Shifting from working in your business to working on your business is key to scaling and building long-term value. Business owners often struggle with...
Why Environmental Due Diligence Matters in M&A
06 Mar 2025
Contributed by Lukas
Environmental issues can be a major hurdle in business transactions, especially for manufacturing companies. Delays in addressing concerns can extend ...
What Business Owners Don’t Know About Exit Planning
27 Feb 2025
Contributed by Lukas
Successful business sales don’t end at the closing table—what happens next is just as important. Business owners need a clear strategy to manage t...
How Real Estate Can Make or Break Your Business Sale
20 Feb 2025
Contributed by Lukas
Real estate plays a crucial role in business sales, and addressing it early can make all the difference. From lease agreements to sale options, seller...
How a Financial Quarterback Guides Business Owners
13 Feb 2025
Contributed by Lukas
Successful business exits require planning, just like a great quarterback leads a team to the Super Bowl. Business owners need a clear strategy to max...
The Risk of Selling at the Wrong Time
06 Feb 2025
Contributed by Lukas
When selling a business, it’s not just about making the sale; it’s about making the right sale. If market conditions aren't favorable, it may...
What’s Driving Optimism in 2025 Business Deals?
30 Jan 2025
Contributed by Lukas
The outlook for 2025 shows potential for growth in M&A activity, with optimism and capital available to support deals. Despite some challenges in ...
This Week's Biggest Hurdle
23 Jan 2025
Contributed by Lukas
Discover the latest insights into the business selling process with our new podcast segment, "This Week's Biggest Hurdle" part of our podcast series '...
Why Private Equity’s Demand for Acquisitions Has Grown
19 Dec 2024
Contributed by Lukas
Understanding the evolving buyer landscape is crucial for business owners in today’s market. From private equity firms to family offices, the variet...
Don't Rely on Familiar Buyers for your Sale!
05 Dec 2024
Contributed by Lukas
Relying on familiar buyers might seem easy, but it can limit your options and the value of your business. In today's episode of 'The Ins and Outs of S...
Multiple Offers... The more the better deal!
21 Nov 2024
Contributed by Lukas
In today’s episode of The Ins and Outs of Selling a Business we’re joined once again by Steven Nicokiris, a seasoned advisor and CPA with over 35 ...
Why CPAs Matter and Guide Successful Business Sales
07 Nov 2024
Contributed by Lukas
Selling a business is often unfamiliar and can cause anxiety, but having the right advisors in place can help ease the process. In our latest episode ...
Key Traits Private Equity Firms Look for in Business Acquisitions with guest Jack McGlinn
24 Oct 2024
Contributed by Lukas
Explore the key characteristics private equity firms prioritize when evaluating potential acquisitions. Grasping these critical factors can significan...
Building Strong Teams for Successful Business Acquisitions with guest Jack McGlinn
10 Oct 2024
Contributed by Lukas
Building a strong team is key to business growth, and finding the right talent infuses your organization with fresh energy and innovative ideas while ...
Motivation Matters in Successful Business Sales: Planning for the Road Ahead
15 Aug 2024
Contributed by Lukas
In today's episode of The Ins and Outs of Selling a Business, we recap the season's highlights and offer a glimpse into what's next in Season 4. Refle...
2024 Market Trends: Mid-Year Review and Predictions
01 Aug 2024
Contributed by Lukas
In the first half of 2024, market activity has been slower than anticipated, especially for larger deals, due to high interest rates and reduced multi...
From Business to Retirement: A Journey of Transformation – with guest Markham Rollins
20 Jun 2024
Contributed by Lukas
Discover the emotional highs and lows of transitioning from business owner to retiree as we continue our conversation with our guest, Mark Rollins. Le...
A Legacy in Transition: Selling a Multi-Generational Business – with guest Markham Rollins
06 Jun 2024
Contributed by Lukas
In today's episode of 'The Ins and Outs of Selling a Business,' we welcome back one of our first guests Markham Rollins to explore the emotional journ...
The Emotional Rollercoaster Of Selling Your Business: Heart Of The Deal - Part 2
23 May 2024
Contributed by Lukas
Discover the emotional journey of selling your business in our latest episode of 'The Ins and Outs of Selling a Business'. Join us as we delve into th...
Heart of the Deal: Emotional Considerations in Selling Your Business
09 May 2024
Contributed by Lukas
In today's episode of 'The Ins and Outs of Selling a Business' we delve deep into the emotional landscape of selling, navigating through doubts, uncer...
Harnessing the Power of CRM: A Blueprint for Business Growth with Jeff Clair
25 Apr 2024
Contributed by Lukas
Discover the intricacies of sales processes and the importance of analytics in our latest episode of 'The Ins and Outs of Selling a Business' with our...
Mitigating Risk in Sales: Strategies for Diversification with Jeff Clair
11 Apr 2024
Contributed by Lukas
Explore the critical aspects of sales strategy, pipeline management, and customer relationships that drive business success in today's episode of 'The...
How Family Dynamics Influence Business Transition with Denis Horrigan
28 Mar 2024
Contributed by Lukas
Discover the real-life stories and essential strategies behind successful business exits in today's episode of 'The Ins and Outs of Selling a Business...
Finding Your Business Exit Route: Insights from Wealth Management Expert Denis Horrigan
14 Mar 2024
Contributed by Lukas
In today's episode of 'The Ins and Outs of Selling a Business' with Denis Horrigan, we discuss the compelling analogy between navigating with old maps...
Leading with Purpose: Creating Organizational Culture - with guest Brent Robertson
28 Feb 2024
Contributed by Lukas
Discover the essential elements of creating a thriving business culture. From understanding the importance of addressing complaints within your organi...
The Art of Adaptation: How Businesses Pivot and Prosper with Guest Brent Robertson
15 Feb 2024
Contributed by Lukas
Understand the importance of creating a culture, gaining buy-in from the team, and executing strategic plans. In today's episode of 'The Ins and Outs ...
Building Valbridge: from Local to National Enterprise with guest Geri Fitapelli
01 Feb 2024
Contributed by Lukas
In today's episode of 'The Ins and Outs of Selling a Business,' we bring back Geri Fitapelli, a seasoned business valuation and real estate expert to ...
Mastering the Market: Achieving a Competitive Business Valuation
18 Jan 2024
Contributed by Lukas
Look closely at factors that influence your company's worth, from technological shifts to market uncertainties. Demystify the reasons why knowing a co...
Beyond the Highest Bid: Factors Influencing Business Sale Decisions
04 Jan 2024
Contributed by Lukas
From valuation surprises to navigating emotional hurdles, discover the intricate strategies that led to a doubling of the purchase price. Unlock the s...
The Team Advantage: One of your biggest Assets when Selling your Company
14 Dec 2023
Contributed by Lukas
Assembling the puzzle of a successful business sale involves more than financial reports. In today's episode of the 'Ins and Outs of Selling a Busin...
Beyond the Sale: Tax Tips for Business Owners - with Richard Austin
30 Nov 2023
Contributed by Lukas
In today's episode of the Ins and Outs of Selling a Business, we bring back Richard Austin of Integrated Partners to discuss expert advice on tax impl...
From Anxiety to Assurance: Planning Your Exit - with Richard Austin
16 Nov 2023
Contributed by Lukas
Unlock the secrets to business exits and dive into the intricacies of successful transactions, strategic planning, and pitfalls to avoid. Join us in t...
2024 Market Forecast: Navigating Business Sales and Valuations
19 Oct 2023
Contributed by Lukas
Several factors, ranging from interest rates to supply chain disruptions, significantly affect M&A deal flow and most sellers and buyers adapt to ...
How Fishing Can Effect the Sale of Your Business
05 Oct 2023
Contributed by Lukas
How does fishing relate to selling your business? It's important for sellers to be prepared and not get distracted by the shiny object. In today's epi...
Maximizing Growth Potential Through Strategic Marketing - with guest Joe Grace
07 Sep 2023
Contributed by Lukas
Realizing the maximum value of your business during a possible sale or acquisition heavily relies on unlocking the secrets to sustained business growt...
How Growth Powers A Successful Transaction - with Joe Grace
24 Aug 2023
Contributed by Lukas
Unlock the keys to a successful business transaction by harnessing the power of growth. In today's episode of The Ins and Outs of Selling a Business, ...
How a Part Time CFO Can Help a Business Owner Maximize Value When Selling, Part 2
20 Jul 2023
Contributed by Lukas
Discover the realm of business transactions, where we serve as intermediaries and advisors, skillfully managing owner concerns and bridging gaps betwe...
How a Part Time CFO Can Help a Business Owner Maximize Value When Selling, Part 1
06 Jul 2023
Contributed by Lukas
Discover the untapped potential of harnessing a Part-Time CFO's expertise to enhance the value of your business when navigating the selling process. I...
Maintaining a Management Team when Selling, Part 2
22 Jun 2023
Contributed by Lukas
Discover the potential of targeted non-qualified compensation programs, surpassing 401k limitations to retain invaluable key employees. In this episod...
Maintaining a Management Team when Selling, Part 1
08 Jun 2023
Contributed by Lukas
Sometimes, raising prices to improve margins can backfire as potential buyers associate it with lower unit sales. In this episode, learn from ou...
How to Exit Your Business on Your Terms, Part 2
25 May 2023
Contributed by Lukas
Discover the importance of sustainable competitive advantage in today's business landscape! In this episode, Keith Dee explores the key factors behind...
How to Exit Your Business on Your Terms, Part 1
11 May 2023
Contributed by Lukas
As a business owner, what are the techniques and strategies that can help you exit your business on your terms? In this episode, Keith Dee explores th...
How to Get a Deal to Letter of Intent when Selling your Business: Part 2
23 Mar 2023
Contributed by Lukas
Contact Keith: Osage Advisors, LLC osageadvisors.com [email protected] 860-767-3273
How to Get a Deal to Letter of Intent when Selling your Business: Part 1
09 Mar 2023
Contributed by Lukas
Contact Keith: Osage Advisors, LLC osageadvisors.com [email protected] 860-767-3273
Why a Cyber Security Plan Maintains Your Company’s Value: Part 2
23 Feb 2023
Contributed by Lukas
Kieth continues his talk with Darragh Fitzpatrick, from the Tabush Group, about the importance of cyber security. Any technical problem is major disru...
Why a Cyber Security Plan Maintains Your Company’s Value
09 Feb 2023
Contributed by Lukas
Tech is intrinsic to everything we do; and therefore, any disruption can be a major hinderance to your business. Cyber security is something we need t...
How Sell Side Quality of Earnings Can Maximize Value with Jeff Rossi
26 Jan 2023
Contributed by Lukas
Contact Keith: Osage Advisors, LLC osageadvisors.com [email protected] 860-767-3273 ✦︎ Subscribe to our YouTube channel!
Financial Due Diligence from a Buyer’s Perspective with Jeff Rossi
15 Dec 2022
Contributed by Lukas
Contact Keith: Osage Advisors, LLC osageadvisors.com [email protected] 860-767-3273 ✦︎ Subscribe to our YouTube channel!
Maximize Your Company’s Value with Will Wilcoxson
01 Dec 2022
Contributed by Lukas
Contact Keith: Osage Advisors, LLC osageadvisors.com [email protected] 860-767-3273 ✦︎ Subscribe to our YouTube channel!
Investing at early stage vs. working with owners to exit their company with guest Will Wilcox
17 Nov 2022
Contributed by Lukas
Contact Keith: Osage Advisors, LLC osageadvisors.com [email protected] 860-767-3273 ✦︎ Subscribe to our YouTube channel!
Proper Tax Planning for Family Businesses with guest Steve Holt
03 Nov 2022
Contributed by Lukas
Contact Keith: Osage Advisors, LLC osageadvisors.com [email protected] 860-767-3273 ✦︎ Subscribe to our YouTube channel!
The Importance of Proper Tax Planning with guest Steve Holt
20 Oct 2022
Contributed by Lukas
Contact Keith: Osage Advisors, LLC osageadvisors.com [email protected] 860-767-3273 ✦︎ Subscribe to our YouTube channel!
Why Deals Don’t Close and How to Close Them (Part 2)
06 Oct 2022
Contributed by Lukas
In today's episode of The Ins and Outs of Selling a Business, Keith is continuing to discuss why deals don't close (what the deal killers are!) and th...
Why Deals Don’t Close (Part 1)
22 Sep 2022
Contributed by Lukas
Contact Keith: Osage Advisors, LLC osageadvisors.com [email protected] 860-767-3273 ✦︎ Subscribe to our YouTube channel!
Wealth Planning During Uncertain Times with guest Megan Trask
08 Sep 2022
Contributed by Lukas
Contact Keith: Osage Advisors, LLC osageadvisors.com [email protected] 860-767-3273 ✦︎ Subscribe to our YouTube channel!
Wealth Planning with Guest Megan Trask
25 Aug 2022
Contributed by Lukas
Contact Keith: Osage Advisors, LLC osageadvisors.com [email protected] 860-767-3273 ✦︎ Subscribe to our YouTube channel!
Trends in the Market for 2022 and Beyond
11 Aug 2022
Contributed by Lukas
Contact Keith: Osage Advisors, LLC osageadvisors.com [email protected] 860-767-3273 ✦︎ Subscribe to our YouTube channel!
2022 Mid Year Market Update
28 Jul 2022
Contributed by Lukas
Contact Keith: Osage Advisors, LLC osageadvisors.com [email protected] 860-767-3273 ✦︎ Subscribe to our YouTube channel!
Top 10 Things that can Devalue a Deal, Part 2
14 Jul 2022
Contributed by Lukas
Contact Keith: Osage Advisors, LLC osageadvisors.com [email protected] 860-767-3273 ✦︎ Subscribe to our YouTube channel!
Top 10 Things that can Devalue a Deal, Part 1
30 Jun 2022
Contributed by Lukas
In today's episode, Keith Dee of Osage Advisors, talks about the top risks for buyers in a deal and how to avoid them. Contact Keith: Osage Advisor...
Transition from the buy-side of a deal to the sell-side
16 Jun 2022
Contributed by Lukas
In today's episode of the Ins and Outs of Selling a Business we bring back Jim Young, an Osage Advisor team member, who shares his experiences with wo...
Buyer’s Perspective: What to Look for When Evaluating a Deal
02 Jun 2022
Contributed by Lukas
In today's episode Keith interviews Jim Young, an Osage team member, who brings an expert perspective on the buy-side of the deal. Contact Keith: O...