Transition Talks: Business Exit & Retirement Strategies

Transition Talks: Business Exit & Retirement Strategies

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.

Episodes

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

October 16, 2025 • 29 mins
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 …

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

September 18, 2025 • 45 mins
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 …

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

June 19, 2025 • 26 mins
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 …

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

May 15, 2025 • 38 mins
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 …

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

April 17, 2025 • 41 mins
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 …

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

March 21, 2025 • 33 mins
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 …

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

December 19, 2024 • 46 mins
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 …

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

November 21, 2024 • 35 mins
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 …

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3 Things to Make Your Business Worth More: Part Two (Ep. 7)

October 17, 2024 • 28 mins
What does it take to truly boost the value of your business for sale? In this episode, Josh Ackerman dives into more strategic ways to maximize your business’s worth. He discusses essential topics every business owner should consider before selling, such as cash flow management and the power of recurring revenue. Learn about leveraging what …

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3 Things to Make Your Business Worth More (Ep. 6)

September 12, 2024 • 28 mins
Want to your business but you’re not sure how to maximize its value? In this episode, Josh Ackerman dives deep into three of the eight key drivers of business value to help you prepare for a successful business sale. From maintaining consistent financial performance to planning for growth potential and ensuring a neutral “Switzerland structure,” …

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Preparing for the Biggest Financial Transition of Your Life with David Hulett (Ep. 5)

August 1, 2024 • 34 mins
Are you ready to learn how to maximize the value of your business before selling? In this episode, Josh Ackerman invites David Hulett, a partner at Corporate Finance Associates of Kentucky and an investment banker who specializes in business sales. They discuss critical steps and considerations for business owners contemplating a sale, from initial preparations …

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The True Wealth Process: More Than Just Numbers (Ep. 4)

July 4, 2024 • 28 mins
Unlock Your Financial Future Beyond the Numbers. Discover how the True Wealth process goes beyond traditional financial planning by prioritizing your life’s goals and aspirations. Today’s episode unpacks Money Quotient’s innovative True Wealth process, aiming to transform financial planning beyond traditional number-crunching by focusing on your values, goals, and true happiness. Josh Ackerman breaks down …

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Questions Business Owners Should Ask Before Selling (Ep. 3)

June 6, 2024 • 28 mins
Imagine realizing the lifestyle you worked so hard for won’t be sustainable after selling your business. Today, we review some key questions business owners often overlook before making irrevocable financial decisions. In this episode of Transition Talks, Josh Ackerman dives into the often-overlooked questions many business owners should ask themselves, or their financial advisor before …

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Inside Context Financial: Guiding Family Businesses Through Change (Ep. 2)

June 6, 2024 • 25 mins
What makes Context Financial uniquely equipped to handle family business transitions? In this episode of Transition Talks, Josh Ackerman talks about what makes Context Financial uniquely equipped to guide family businesses through significant transitions. He shares the company’s history, founded by his father in 2000, and emphasizes the importance of understanding client context. Josh explains …

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Getting to Know Josh Ackerman: Why Financial Advising? (Ep. 1)

June 6, 2024 • 27 mins
Are you ready to navigate the complexities of business exits and retirement strategies? It’s a significant life change that many aren’t fully prepared for. That’s why it’s so important to find and work with an advisor who’s the right fit for you. Welcome to the inaugural episode of Transition Talks with Josh Ackerman, where he …

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