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 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.

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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.

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.

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?”

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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.”

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.

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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. 

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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.

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.

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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.

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.

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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.

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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. 

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. 

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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 your business does best to stand out in the market, and hear real-world examples, like Panasonic’s creation of the Toughbook, illustrating monopoly control.

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Tune in for actionable tips to navigate your next business transition effectively.

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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,” you’ll learn how you can fetch a higher sale price. Tune in to get actionable tips on improving your business’s market worth.

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