Transition Talks: Business Exit & Retirement Strategies

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 tim

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 cover

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 focu

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 ma

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 futur

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 con