Transition Talks: Business Exit & Retirement Strategies

Josh Ackerman
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Welcome to Transition Talks: Business Exit & Retirement Strategies with your host, Josh Ackerman. This podcast was designed exclusively for business owners contemplating the pivotal step of selling or transitioning their business. Josh, is a seasoned financial planner with a passion for guiding entrepreneurs through significant life changes. In this podcast, he will share invaluable insights, stories, and strategies to help you navigate the intricate process of passing the torch.

  1. 10/16/2025

    How to Clarify Your Goals and Redefine Success with Carl Richards (Ep. 15)

    What if your financial goals aren’t really financial at all? In this deeply reflective episode of Transition Talks, host Josh Ackerman welcomes acclaimed author and visual thinker Carl Richards to unpack the real purpose of money. Known for his iconic “napkin sketches,” Carl shares stories, metaphors, and mindset shifts that challenge how we think about wealth, identity, and success. You’ll learn why most financial plans go sideways, not because of bad math, but because we don’t spend enough time asking the right questions. Together, Josh and Carl explore three key sketches from Carl’s upcoming book and walk listeners through real-world applications of values-first planning. What to expect: Why “Tell me your goals” is often the wrong starting point How to separate personal aspirations from financial assumptions Why two people never see money the same way, and how to talk through it The surprising difference between speculating and investing And more! Resources: “Your Money: Reimagining Wealth in 101 Simple Sketches” by Carl Richards  Place a bulk order of Your Money! Use code YourMoney5 at checkout to save an additional 5% Connect with Josh Ackerman:  Context Financial josh@contextfinancial.com LinkedIn: Josh Ackerman Facebook: Context Financial, LLC Instagram: Context Financial YouTube: Context Financial Connect with Carl Richards: The Society of Advice LinkedIn: Carl Richards Twitter: @behaviorgap Instagram: @behaviorgap BehaviorGap.com About Our Guest:  Carl Richards started The Sketch Guy column in The New York Times from the hills of Utah, crafting clear, relatable insights about money with just cardstock and a Sharpie. The column ran weekly for a decade. This journey began when Carl applied for what he thought was a job as a “security guard,” only to find out the ad actually said “securities.” That slight misstep sparked a lifelong dedication to reshaping how we think about money. Since then, Carl has become a Certified Financial Planner, built and sold a successful investment firm, and spoken at financial and investment events worldwide from Australia to South Africa, the UK, and major economic centers across Europe, Canada, and the United States. His bestsellers, The Behavior Gap and The One-Page Financial Plan, have been translated into over ten languages and continue to resonate globally. Through his daily podcast, Behavior Gap Radio, which now has over 1,000 episodes and over one million downloads, Carl shares new perspectives on aligning our resources with what truly matters. His latest audio project, 50 Fires, backed by executive producers Chip and Joanna Gaines, explores the intersections of money and meaning with guests like Pete Holmes, David Whyte, Krista Tippett, and his favorite guest by far, his wife, Cori. Carl founded The Society of Advice, a community of financial planners dedicated to the craft of advice. They gather for a monthly online workshop and frequent retreats in Park City, Utah. In 2025, Carl will release a new book that, true to form, will be unlike anything seen in the personal finance section, and you better believe there will be sketches (97 of them, to be exact). When he’s not exploring ideas about money, Carl, a Wilderness First Responder, can be found navigating Utah’s high mountain ridges on foot, skis, or bike. Married to Cori since 1995, they have four kids, whom they consider their best friends.

    29 min

  2. 09/18/2025

    Life After Business: The Emotional Side of Exit Planning with Denise Logan (Ep. 14)

    What happens when the hardest part of selling your business isn’t the numbers, but the life change that follows? In this episode, Josh Ackerman welcomes Denise Logan, former attorney and now known as The Seller Whisperer, for a candid look at the emotional side of exiting a company. Denise shares powerful stories from her work with business owners who grapple with identity, purpose, relationships, and the big question: “What comes next after the business?” Gain insight as this conversation covers: Denise’s journey from therapist to lawyer to transition guide Why business exits feel like both freedom and loss The unseen needs work provides beyond money and security How identity, power, and relationships shift after a sale Practical ways to build structure, friendships, and purpose in the next chapter And more Resources: The Seller’s Journey by Denise Logan Osher Lifelong Learning Institute (OLLI) Connect with Josh Ackerman:  Context Financial josh@contextfinancial.com LinkedIn: Josh Ackerman Facebook: Context Financial, LLC Instagram: Context Financial YouTube: Context Financial Connect with Denise Logan: deniselogan.com LinkedIn: Denise Logan  About Our Guest: Denise Logan is a nationally recognized speaker, author, and trusted advisor known as The Seller Whisperer. With a background as both a therapist and an attorney, she specializes in helping business owners and their advisors navigate the emotional side of selling a company. Through her one-on-one work and her book, The Seller’s Journey, Denise has guided hundreds of entrepreneurs through the complex and deeply personal process of letting go, ensuring they land safely in their “life after business.”

    45 min

  3. 06/19/2025

    Why Your $10M Business Sale Might Only Net You $3M (Ep. 13)

    Most business owners dream about the big payout, but not enough focus on the number that matters: what ends up in your pocket.  In this practical and often eye-opening episode of Transition Talks, Josh Ackerman walks us through what every seller should know before inking a deal. From the impact of business structure to state residency and even charitable planning, Josh explains why preparation is your best strategy. You’ll learn why a flashy sale price can be misleading—and how to shift your focus to net outcomes with smart tax planning. By listening, you’ll discover: Why LLCs, S corps, and C corps lead to dramatically different tax bills How asset sales vs. stock sales affect buyers and sellers Simple ways to prepare for lower taxes years before the deal How charitable remainder trusts can benefit your legacy and wallet And more! Connect with Josh Ackerman:  Context Financial josh@contextfinancial.com LinkedIn: Josh Ackerman Facebook: Context Financial, LLC Instagram: Context Financial YouTube: Context Financial

    27 min

  4. 05/15/2025

    How to Align Your Business Sale with Personal Goals with Matt Lockaby (Ep. 12)

    What happens when you’re truly ready to sell your business?  This discussion can help you avoid the pitfalls of business transitions and help create a smooth, successful exit. Join Josh Ackerman and special guest Matt Lockaby, an experienced attorney with a knack for supporting business owners through the buy-sell process, as they break down the key elements of successful business sales and transitions.  From understanding your true goals to preparing your financials, Matt and Josh want to help make sure you’re ready for the next chapter.  Key conversations in this episode include: The make-or-break importance of knowing your end goals [00:04:42] Common pitfalls in the emotional and psychological side of selling a business [00:06:13]  Why cleaning up your books is crucial before a sale [00:16:46]  Challenges and stories from real business transitions that went well (and those that didn’t) [00:24:44]  The intriguing rise of young, educated buyers in the business market [00:30:36] And more! Resources: Axis HR Consulting Connect with Josh Ackerman:  Context Financial josh@contextfinancial.com LinkedIn: Josh Ackerman Facebook: Context Financial, LLC Instagram: Context Financial YouTube: Context Financial Connect with Matthew Lockaby: Lockaby Law LinkedIn: Matthew Lockaby Facebook: Lockaby PLLC Instagram: @lockaby_pllc mlockaby@lockabylaw.com  (859) 263-7884 About Our Guest:  As the Managing Member of Lockaby PLLC, Matthew Lockaby represents employees, employers, and management in nearly every aspect of workplace law and advises small and midsized businesses on corporate and M&A matters, and acts as outside general counsel. M&A COUNSEL — Matthew represents buyers and sellers in lower-middle-market / “Main Street” transactions, often working with the buyer and seller through due diligence and post-close obligations. In larger transactions, he provides specialized labor-and-employment guidance for buyers and sellers, including pre-deal due diligence (e.g., a review of employment contracts, restrictive covenants, policies, and practices that impact the transaction), liability analysis (i.e., liabilities related to employment claims, wage-and-hour compliance, and employee benefits), and compliance analysis (e.g., classification and pay audits and other “stress testing” under federal, state, and local regulations). PREVENTATIVE COUNSEL — Matthew provides compassionate yet business-minded guidance on a wide variety of issues that arise during the employment lifespan, from hiring to disciplinary action to leaves of absence to separation. TRANSACTIONAL COUNSEL — He drafts and negotiates workplace contracts, including operating, shareholder, and buy-sell agreements and other employment agreements, such as non-compete, non-solicit, and non-disclosure agreements, independent contractor agreements, arbitration agreements, and severance agreements. INVESTIGATIONS COUNSEL — Matthew oversees and conducts internal investigations into director, officer, and employee misconduct, including the defense of government agency investigations. LITIGATION COUNSEL — He defends discrimination, retaliation, harassment, wage-and-hour, and breach-of-contract claims in state and federal courts, administrative agencies, and arbitration, including both class-action and FLSA collective-action claims. No matter the client, Matthew’s singular focus is the same: vigorous yet transparent, cost-effective representation specifically tailored to resolve each client’s problem and achieve each client’s goals as quickly and efficiently as possible.

    38 min

  5. 04/17/2025

    Smart Strategies for Passing Down the Family Farm with Justin Schuhmacher (Ep. 11)

    What complexities surround inheriting a family farm, and how do family dynamics influence estate planning?  Josh Ackerman hosts Justin Schuhmacher, an attorney at Indiana Estate & Elder Law, for a lively conversation about passing down the farm, a topic rich with parallels to other family businesses. The two explore real-life stories, learning how involving the next generation early can propel businesses forward, why transparency with heirs is crucial, and how strategic planning can prevent future disputes. Key takeaways include: Why involving heirs early in decision-making is a smart move (15:33) The pitfalls of treating heirs equally vs. fairly in estate planning (22:32) Justin’s insights into avoiding family conflicts over inheritances (29:10) How trust planning can safeguard family assets and relationships (25:58) Connect with Josh Ackerman:  Context Financial josh@contextfinancial.com LinkedIn: Josh Ackerman Facebook: Context Financial, LLC Instagram: Context Financial YouTube: Context Financial Connect Justin Schuhmacher: Indiana Estate Elder Law Linkedin Justin Schuhmacher About Justin Schuhmacher:  Justin Schuhmacher is a dedicated estate and elder law attorney in Indiana, committed to helping families safeguard their assets and plan for the future. Understanding that unforeseen events can disrupt even the best-laid plans, Justin works closely with clients to protect their wealth from risks such as lawsuits, long-term care costs, and financial missteps.

    41 min

  6. 03/21/2025

    The Emotional Side of Selling Your Business (Ep. 10)

    How do you plan for life after selling your business? Join Josh Ackerman as he explores the emotional and psychological journey many business owners face after selling their enterprises.  This isn’t just about the numbers; it’s about understanding the push and pull factors that influence your decision to exit, from health changes and market shifts to personal aspirations like political involvement. Josh explores different exit strategies, from outright sales to retaining partial ownership and consultancy roles, and illustrates the importance of maintaining a vibrant social circle and identity outside of work. With valuable insights into aligning your financial and personal goals, this episode is a must-listen for anyone considering a business transition. Key discussion points include: The push and pull factors affecting business exits [00:03:43] Emotional readiness for life post-sale [00:08:43] The importance of social connections beyond business [00:14:00] Different types of business exit strategies [00:10:30] Encouragement to think strategically about life’s next chapter [00:16:39] And more! Connect with Josh Ackerman:  Context Financial josh@contextfinancial.com LinkedIn: Josh Ackerman Facebook: Context Financial, LLC Instagram: Context Financial YouTube: Context Financial

    33 min

  7. 12/19/2024

    Hope is Not a Strategy: The Roadmap to Selling Your Business with Geoff Eliason (Ep. 9)

    What happens when a business owner hands over the keys? What are the emotional and financial intricacies involved in selling a business?  Josh Ackerman welcomes special guest Geoff Eliason, CEO and owner of SDR Ventures, an investment bank in Denver. They explore Geoff’s journey from startup to CEO, his passion for connecting business owners with opportunities, and the critical role of financial advisors. They touch on the challenges business owners face when preparing for succession, the importance of planning for life after selling a business, and the complexities of deal structures. Josh and Geoff discuss:  Geoff’s career trajectory from launching ETFs to leading an investment bank (00:01:00) The $10 trillion opportunity in retiring baby boomer businesses (00:07:00) Navigating succession when kids prefer different paths (00:10:00) Ensuring a fulfilling life post-sale by understanding personal aspirations (00:14:00) The surprising misconceptions about business sales and transitions (00:26:27) And more Connect with Josh Ackerman:  Context Financial josh@contextfinancial.com LinkedIn: Josh Ackerman Facebook: Context Financial, LLC Instagram: Context Financial YouTube: Context Financial Connect with Geoff Eliason: SDR Venture Integrity Wealth Advisors LinkedIn: Geoff Eliason About Our Guest:  Geoff Eliason joined the SDR Ventures team in 2021. In his role as Principal, Eliason brings 16 years of industry experience to the organization and its clients. His primary responsibilities are building and sustaining operational efficiencies across the firm and maximizing the client service model. Geoff is dedicated to providing strategic solutions specific to the complexities of the M&A process. Embracing SDR Ventures firm-wide commitment to serving its clients, Eliason channels his years of experience and strategic relationships toward enhancing business valuations and providing thought leadership to the entrepreneurial community. Geoff holds his Series 79, 24, and 63 securities licenses and serves as SDR Capital Markets Chief Compliance Officer. Eliason is passionate about teamwork given his commitment to both education and athletics.

    47 min

  8. 11/21/2024

    3 Things to Make Your Business Worth More: Part Three (Ep. 8)

    Josh Ackerman delves into improving business value through the eight drivers, touching specifically on the power of customer referrals and the pivotal “Hub and Spoke” model. Learn why moving from high owner dependence to a structured company could not only ease your own workload but significantly boost your business’s market valuation.  Josh discusses:  How customer referrals impact business sales The critical question to enhance referrals: the Net Promoter Score (NPS) The nuances of the Hub and Spoke model and its influence on enterprise value  Ways to empower your team and become less central to daily operation And more Resources: 3 Things to Make Your Business Worth More 3 Things to Make Your Business Worth More: Part Two Connect with Josh Ackerman:  Context Financial josh@contextfinancial.com LinkedIn: Josh Ackerman Facebook: Context Financial, LLC Instagram: Context Financial YouTube: Context Financial

    35 min
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About

Welcome to Transition Talks: Business Exit & Retirement Strategies with your host, Josh Ackerman. This podcast was designed exclusively for business owners contemplating the pivotal step of selling or transitioning their business. Josh, is a seasoned financial planner with a passion for guiding entrepreneurs through significant life changes. In this podcast, he will share invaluable insights, stories, and strategies to help you navigate the intricate process of passing the torch.

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