DeSimone on Deals: The Exit Strategy Podcast

DeSimone on Deals: The Exit Strategy Podcast
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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.

  1. 2d ago

    Most Business Owners Are Not Prepared to Exit - Are You? | DeSimone on Deals with Anthony Perez

    You've spent years building your business, but are you financially prepared to walk away? And will the proceeds from selling your company actually support the life you want after the exit?In this episode of Dismount Deals: The Exit Strategy Podcast, Greg sits down with Anthony Perez, CFP®, AWMA®, Founder of Harvest Wealth Strategies, to discuss how business owners can prepare for a successful exit, maximize company value, reduce taxes, and turn years of hard work into lasting financial freedom.With more than 25 years in financial services and executive leadership, Anthony shares why exit planning should start long before you're ready to sell—and why focusing only on the sale price can be a costly mistake.In this episode, you'll learn: Why exit planning should begin the day you start your business.How to protect your personal wealth when most of it is tied up in your company.Why a $10 million deal doesn't necessarily mean you'll walk away with $10 million.How deal structure, taxes, and payment terms affect your actual proceeds.The three key areas that can increase business value: people, systems and processes, and customer diversification.How owner dependency can put a deal—and your business valuation—at risk.Why business owners need to plan for life after the sale, not just the financial outcome.How to balance maximum sale value with employee retention, family priorities, and your business legacy.Anthony also shares real-world examples of business owners who faced difficult exit decisions because they didn't plan early enough—and how proper preparation can create more choices, stronger negotiating leverage, and a smoother transition.The biggest takeaway? A successful exit isn't just about selling your business for the highest price. It's about building a business that can thrive without you and creating a financial future that gives you freedom and options.About Anthony PerezAnthony Perez, CFP®, AWMA®, is the Founder of Harvest Wealth Strategies and an Exit Planning Advisor. Through his proprietary Freedom Roadmap™ process, he helps business owners understand what their companies are worth, close value gaps, prepare for an eventual transition, and ensure their sale proceeds support the life they envision.If you're a business owner thinking about retirement, succession, or selling your company, this conversation will help you start asking the right questions—before it's too late.

  2. Sep 29

    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 #BusinessSale #ExitStrategy #EmploymentLaw #DueDiligence #BusinessGrowth #Entrepreneurship #MergersAndAcquisitions

  3. May 29

    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 #exitstrategy #businessowner #businessgrowth #businessvalue #leadership #entrepreneurship #successionplanning #mergersandacquisitions

  4. Apr 9

    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 #companyculture #businessexit #leadershipgoals #businessowner #businesspodcast #businessgrowth #entrepreneurship

  5. Feb 25

    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.

  6. Jan 8

    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 #familybusiness #mergersandacquisitions #familybusinesstips #businessexit

  7. Jan 8

    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 #mergersandacquisitions #familybusiness #familybusinesstips #businessexit

  8. 09/20/2025

    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 #BusinessExit #MergersAndAcquisition #SellYourBusiness#SmallBusinessTips #BusinessAcquisition #DealMaking #BusinessTransition #ExitPlanning

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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.

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