About DeSimone on Deals: The Exit Strategy Podcast
Every business owner will exit their business someday—the real question is whether you'll do it on your own terms. Hosted by Greg DeSimone, President of Catapult Advisory Group, DeSimone on Deals helps owners build value, prepare for transition, and maximize outcomes when selling. Through conversations with top M&A professionals, attorneys, accountants, and lenders, Greg shares practical advice on valuation, succession planning, leadership, and deal-making. Whether selling next year or in a decade, learn how to build a transferable business and achieve the exit you deserve.
The Employment Law Issues That Can Derail Your Business Sale | DeSimone on Deals with Tim Kenneally
What employment-law issues can create problems when you're preparing to sell your business?In this episode, Greg DeSimone sits down with Tim G. Kenneally, who brings decades of experience in employment and labor law to the conversation. Tim shares practical insight into the legal issues business owners should be thinking about well before a transaction is on the table.The conversation explores the kinds of employment-related risks that can surface during due diligence, including wage-and-hour issues, employee classification, overtime, employment agreements, and other compliance concerns. We also discuss why certain practices that may seem harmless while you're operating the business can become much more significant when a buyer begins taking a closer look.For business owners preparing for an eventual exit, the takeaway is simple: don't wait until you're in the middle of a transaction to discover problems that could have been addressed years earlier.Whether you're planning to sell soon or simply want to build a cleaner, stronger business, this conversation with Tim G. Kenneally offers valuable perspective on preparing for the legal side of a successful exit.#BusinessOwners (https://www.youtube.com/hashtag/businessowners) #BusinessSale (https://www.youtube.com/hashtag/businesssale) #ExitStrategy (https://www.youtube.com/hashtag/exitstrategy) #EmploymentLaw (https://www.youtube.com/hashtag/employmentlaw) #DueDiligence (https://www.youtube.com/hashtag/duediligence) #BusinessGrowth (https://www.youtube.com/hashtag/businessgrowth) #Entrepreneurship (https://www.youtube.com/hashtag/entrepreneurship) #MergersAndAcquisitions (https://www.youtube.com/hashtag/mergersandacquisitions)
29 May 2026
What Buyers Really Look For Before Buying Your Business | DeSimone on Deals with Kevin Baker
What do buyers actually look for before acquiring a business?And what causes deals to fall apart — even after an offer is signed?In this episode, Greg DeSimone sits down with Kevin Baker, Director of Development at Emergency Care Partners, who evaluates acquisitions and partnerships as part of his day-to-day role. From the buyer’s side of the table, Kevin shares what really drives business value, what creates risk, and what business owners should prepare long before they ever think about selling.You’ll learn why clean financials build trust, why relying on one customer can reduce your company’s value, and why buyers don’t pay for potential alone. Kevin also explains how strong leadership, organized records, and the right advisory team can speed up transactions and help deals close with confidence. Buyers consistently prioritize reliability, preparation, and risk management when deciding whether to move forward with an acquisition.Whether you're planning to sell your business someday or simply want to build a stronger company, this conversation will help you think like a buyer — and prepare your business accordingly.#businessexit (https://www.youtube.com/hashtag/businessexit) #exitstrategy (https://www.youtube.com/hashtag/exitstrategy) #businessowner (https://www.youtube.com/hashtag/businessowner) #businessgrowth (https://www.youtube.com/hashtag/businessgrowth) #businessvalue (https://www.youtube.com/hashtag/businessvalue) #leadership (https://www.youtube.com/hashtag/leadership) #entrepreneurship (https://www.youtube.com/hashtag/entrepreneurship) #successionplanning (https://www.youtube.com/hashtag/successionplanning) #mergersandacquisitions (https://www.youtube.com/hashtag/mergersandacquisitions)
9 Apr 2026
Why 85% of Businesses Never Sell — and How to Build One That Does | DeSimone on Deals with Jon Chen
Most business owners assume they’ll sell their company someday.But the reality is shocking: about 85% of businesses that go to market never sell.In this episode of DeSimone on Deals: The Exit Strategy Podcast, Greg DeSimone sits down with Jon Chen, founder of Blue Tide Catalyst, to discuss how business owners can dramatically increase the value of their company — and actually build a business someone wants to buy.They explore why growth alone doesn’t create value, how owner dependency can destroy a deal, and why culture, leadership, and systems are often the biggest drivers of enterprise value.Jon also shares practical strategies for transforming a business from chaotic “kids soccer” operations into a structured company that can scale — and eventually exit successfully.In this episode you’ll learn:• Why 85% of businesses never sell• The biggest mistake entrepreneurs make when building value• How removing owner dependency can increase valuation multiples• Why growth can actually create more problems than it solves• The leadership and culture shifts that unlock real company value• How one company grew from $5M to a $60M exitIf you’re building a company and thinking about your long-term exit strategy, this conversation is packed with insights you won’t want to miss.#exitstrategy (https://www.youtube.com/hashtag/exitstrategy) #companyculture (https://www.youtube.com/hashtag/companyculture) #businessexit (https://www.youtube.com/hashtag/businessexit) #leadershipgoals (https://www.youtube.com/hashtag/leadershipgoals) #businessowner (https://www.youtube.com/hashtag/businessowner) #businesspodcast (https://www.youtube.com/hashtag/businesspodcast) #businessgrowth (https://www.youtube.com/hashtag/businessgrowth) #entrepreneurship (https://www.youtube.com/hashtag/entrepreneurship)
25 Feb 2026
Building a Transition-Ready Business Through Leadership | DeSimone on Deals with David Liddel
Preparing your business for a successful transition isn’t just about numbers — it’s about leadership. In this episode, David Liddell, CEO and Founder of Liddell Consulting Group, shares what he sees business owners struggle with most as they prepare for transition. From trust and decision-making to leadership team dynamics, David explains how owners can move from being the center of everything to building a team that can carry the business forward. He also breaks down why there’s no such thing as a perfect plan — only smart options that create flexibility, confidence, and long-term value.
8 Jan 2026
How to Successfully Transition Your Family Business (Without Losing Control) | with Brad Herda
Most owners don’t plan to sell their business… but they do want to get out of the day-to-day. This episode shows how to transition a family business or management team without giving up ownership.Our guest is Brad Herda — founder and Managing Director of Vision Forward Business Solutions, master coach, and co-host of the Blue Collar BS Podcast. He works with business owners to build succession plans, grow teams, and improve performance across generations. 12- DeSimone on Deals -Transcri…In this episode, Brad shares:1. Why ownership and operations must be separated2. How to set boundaries and choose the right KPIs3. Managing different generations in one company4. Using data instead of intuition5. Letting the business pay for its own transition6. What to do when the older generation wants “the lump sum”7. A success story where revenue doubled by investing in peopleIf you want your business to run without you — and prepare the next generation — this conversation is packed with practical insights.#exitstrategy (https://www.youtube.com/hashtag/exitstrategy) #familybusiness (https://www.youtube.com/hashtag/familybusiness) #mergersandacquisitions (https://www.youtube.com/hashtag/mergersandacquisitions) #familybusinesstips (https://www.youtube.com/hashtag/familybusinesstips) #businessexit (https://www.youtube.com/hashtag/businessexit)
8 Jan 2026
How Family Businesses Fail — And How to Beat the Odds | DeSimone on Deals with Jeremy Stevenson
Most family businesses don’t make it past the second generation — and it’s not because of profits. In this episode, Greg DeSimone talks Jeremy Stevenson from IBRIDGE GLOBAL PARTNERS about the hidden traps that derail succession, the emotional and family dynamics that get in the way, and the proven steps owners can take to protect both their wealth and their legacy. If you’re planning to sell, scale, or pass your company to the next generation, this is an episode you can’t afford to miss.#exitstrategy (https://www.youtube.com/hashtag/exitstrategy) #mergersandacquisitions (https://www.youtube.com/hashtag/mergersandacquisitions) #familybusiness (https://www.youtube.com/hashtag/familybusiness) #familybusinesstips (https://www.youtube.com/hashtag/familybusinesstips) #businessexit (https://www.youtube.com/hashtag/businessexit)
20 Sept 2025
Buy-Side vs. Sell-Side: What Really Makes a Deal Work | DeSimone on Deals with Dave Sterrett
In this episode of The Exit Strategy Podcast, Greg DeSimone sits down with Dave Sterrett, Principal at Legal Deal Makers, to compare the buy-side and sell-side of business acquisitions. Greg represents sellers, while Dave works with buyers—so they dive deep into where deals often stall, how to navigate quality of earnings, working capital, and deal structure, and why understanding both perspectives leads to better outcomes.Whether you’re preparing to sell your business or considering an acquisition, this episode unpacks real-world lessons on negotiations, risk, taxes, and deal strategy that every owner should hear before making a move.#ExitStrategy (https://www.youtube.com/hashtag/exitstrategy) #BusinessExit (https://www.youtube.com/hashtag/businessexit) #MergersAndAcquisition (https://www.youtube.com/hashtag/mergersandacquisition) #SellYourBusiness (https://www.youtube.com/hashtag/sellyourbusiness)#SmallBusinessTips (https://www.youtube.com/hashtag/smallbusinesstips) #BusinessAcquisition (https://www.youtube.com/hashtag/businessacquisition) #DealMaking (https://www.youtube.com/hashtag/dealmaking) #BusinessTransition (https://www.youtube.com/hashtag/businesstransition) #ExitPlanning (https://www.youtube.com/hashtag/exitplanning)
20 Sept 2025
How Lawsuits, Shareholder Fights, and Poor Planning Tank Business Deals | DeSimone on Deals with Sally McDonald
Selling your business? One lawsuit—or even a hint of legal trouble—can crush your valuation or scare off buyers completely. In this episode, Greg speaks with top business litigator Sally McDonald about the real impact of litigation on business exits. From shareholder disputes to employee claims to “friendship gone wrong” lawsuits, Sally shares cautionary tales and practical tips to avoid turning your sale into a courtroom drama.You’ll learn:1. How buyers react to pending lawsuits2. What indemnification really means in a deal3. The cost of skipping operating agreements4. Why being unemotional can save your businessWhether you’re planning your exit or just trying to stay out of legal trouble, this episode is a must-listen.#exitstrategy (https://www.youtube.com/hashtag/exitstrategy) #gregdesimone (https://www.youtube.com/hashtag/gregdesimone) #mergersandacquisitions (https://www.youtube.com/hashtag/mergersandacquisitions) #businessgrowth (https://www.youtube.com/hashtag/businessgrowth) #litigation (https://www.youtube.com/hashtag/litigation) #businessowner (https://www.youtube.com/hashtag/businessowner)
20 Sept 2025
Navigating SBA Loans for Business Acquisitions | DeSimone on Deals with Kathy Kelly
In this episode, host Greg DeSimone sits down with Kathy Kelly from Webster Bank, a leading expert in SBA lending. They dive deep into the ins and outs of financing business acquisitions, covering everything from down payments and seller notes to common deal pitfalls and creative financing solutions. Whether you're a business owner looking to sell or an aspiring buyer, this episode is packed with practical advice on how to structure deals, avoid costly mistakes, and maximize your chances of securing funding.#sbaloans (https://www.youtube.com/hashtag/sbaloans) #financing (https://www.youtube.com/hashtag/financing) #exitplanning (https://www.youtube.com/hashtag/exitplanning) #businessacquisition (https://www.youtube.com/hashtag/businessacquisition) #businessfinance (https://www.youtube.com/hashtag/businessfinance)
20 Sept 2025
Disagreements, Divorce, Death & Disability—Is Your Business Prepared? | DeSimone on Deals with Theresa Barbadoro
Thinking about selling your business someday? Then you need to plan ahead—way ahead. In this episode, we sit down with attorney Theresa Barbadoro to talk about the biggest mistakes business owners make when exiting (or failing to exit) their companies. From the "4 Ds" (Death, Disability, Divorce, and Disagreement) to buy-sell agreements and succession planning, this conversation is packed with real-world advice that could save you a fortune and a major headache. Whether you're planning to sell soon or just getting started, this is a must-listen for every business owner. Tune in now!#businessowner (https://www.youtube.com/hashtag/businessowner) #exitstrategy (https://www.youtube.com/hashtag/exitstrategy) #exitplanning (https://www.youtube.com/hashtag/exitplanning) #businesstips (https://www.youtube.com/hashtag/businesstips)
20 Sept 2025
Buy-Side vs. Sell-Side: What Really Makes a Deal Work | DeSimone on Deals with Dominic Rubino
In this episode, we dive deep into the essential strategies that make businesses more viable, profitable, and ready for the future. Guest expert Dominic Rubino shares simple systems that business owners can implement to increase efficiency, build value, and create a company that runs without chaos. Whether you're preparing to sell your business, pass it on, or just want more freedom, these actionable insights will set you on the right path. Don't miss Dominic's proven advice for creating a predictable and scalable business! #exitstrategy (https://www.youtube.com/hashtag/exitstrategy) #businesstips (https://www.youtube.com/hashtag/businesstips) #businessowner (https://www.youtube.com/hashtag/businessowner) #exitplanning (https://www.youtube.com/hashtag/exitplanning)
27 Jun 2025
Exit Strategies Simplified | DeSimone on Deals with Todd Eppert
In this episode of DeSimone on Deals, Todd Eppert, an expert business coach and Certified Exit Planning Advisor, shares his insights into preparing businesses for successful transitions. From family-owned enterprises to private equity sales, Todd delves into topics like mitigating owner dependency, addressing key employee risks, and navigating the complexities of valuation. Gain actionable strategies to ensure your business is ready for the next chapter—whether that's a family succession or a lucrative sale. Don't miss Todd's expertise on building value and de-risking your business for a smooth exit.#exitstrategy (https://www.youtube.com/hashtag/exitstrategy) #exitplanning (https://www.youtube.com/hashtag/exitplanning) #businessowner (https://www.youtube.com/hashtag/businessowner) #sellyourbusiness (https://www.youtube.com/hashtag/sellyourbusiness)
27 Jun 2025
Successful Exit: How He Built and Sold His Security Firm | DeSimone on Deals with Tim Mazzie
In this episode, we sit down with Tim Mazzie, founder of RSIG Security Inc, to discuss the steps he took to prepare his business for sale. Tim shares the strategies that helped him maximize his outcome and offers advice for other entrepreneurs eyeing their own exits.#exitstrategy (https://www.youtube.com/hashtag/exitstrategy) #businessowner (https://www.youtube.com/hashtag/businessowner) #businesstips (https://www.youtube.com/hashtag/businesstips) #businessgrowth (https://www.youtube.com/hashtag/businessgrowth) #entrepreneur (https://www.youtube.com/hashtag/entrepreneur)
27 Jun 2025
From Planning to Profit: Navigating the Business Sale Process | DeSimone on Deals with Jeff Muir
In this episode, host Greg DeSimone is joined by Jeff Muir from Sinclair Advisors to discuss the ins and outs of selling your business. With over 15 years of M&A experience and two decades in commercial banking, Jeff shares valuable insights on preparing your business for sale, avoiding common mistakes, and maximizing value. From family dynamics to strategic planning, this episode covers everything business owners need to know for a successful exit.#BusinessPodcast #MergersAndAcquisitions #SellingABusiness #BusinessExitStrategy #EntrepreneurTips
27 Jun 2025
Preparing Your Business for Sale | DeSimone on Deals with Bennett Lebowitz
In this episode, host Greg DeSimone welcomes Bennett Lebowitz from Pando Consulting. Together, they explore the critical aspects of exit strategies for business owners. Discover the common pitfalls that lead to failed sales, the importance of holistic planning, and actionable steps you can take to ensure a successful transition. Whether you're preparing to sell or simply want to learn more about maximizing your business's value, this episode is a must-watch!#exitstrategy (https://www.youtube.com/hashtag/exitstrategy) #businessstrategy (https://www.youtube.com/hashtag/businessstrategy) #businessowner (https://www.youtube.com/hashtag/businessowner) #businesstips (https://www.youtube.com/hashtag/businesstips)
27 Jun 2025
How to Avoid Exit Strategy Mistakes | DeSimone on Deals with Alan Bennett
In the first episode of "DeSimone on Deals," host Greg DeSimone interviews Alan Bennett, an entrepreneur and business coach with Focal Point Coaching International. Alan shares his journey from corporate America to running a meat market and catering business, highlighting the mistakes he made during his business exits. Learn how Alan's experiences led him to become a Certified Exit Planning Advisor (CEPA) and discover valuable insights into preparing your business for a successful sale. Don't miss this candid discussion on avoiding common pitfalls and maximizing business value.#businessstrategy (https://www.youtube.com/hashtag/businessstrategy) #businessowner (https://www.youtube.com/hashtag/businessowner) #businesstips (https://www.youtube.com/hashtag/businesstips)
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