The Founder's Exit Paradox (Feat: Jerome Myers)

The Founder's Exit Paradox (Feat: Jerome Myers)

Exiting a business is often seen as the ultimate milestone — but for many founders, it’s just the beginning of a more complex, emotional journey. In this episode of Advance Your Wealth, I sit down with Jerome Myers, one of the country’s leading experts on business exits and the psychology behind them. After building a $20M division of a Fortune 550 company, Jerome walked away to help high-achieving entrepreneurs confront what he calls the Founder’s Exit Paradox — the unexpected void that can follow even the most successful exits. We discuss the emotional challenges leaders face when stepping away, his N.E.X.T. framework for navigating life after business, and how to move from success to true significance. Whether you're nearing your exit or simply contemplating what comes after the grind, this episode offers a rare look at how to plan not just financially, but personally, for what's next. Chapters: 0:00 - Introduction 2:14 - The Founder's Exit Paradox 9:45 - Planning for your business, but not your life 17:00 - A portal to personal evolution 22:53 - Closing remarks

Don't Have a Vision for Retirement? It's Time to Fix That!

Planning your retirement from a financial perspective is probably one of your most important goals. After all, you want to have enough money to live a good life. But what does that good life look like? If you’re like many people, you may not have defined clearly what your retirement years are going to be all about. On the latest installment of Advance Your Wealth, we’re examining how you can craft and refine a compelling vision for your retirement.  Chapters: 0:00 - Introduction 2:01 - This doesn't get enough attention 6:20 - Actionable steps for envisioning ideal retirement 13:53 - Key takeways 17:23 - Closing remarks

Are Big Estate Tax Changes Coming?

As we step into 2025, wealthy families and their advisors are already looking ahead to major potential changes in estate and gift tax laws. With key provisions of the 2017 Tax Cuts and Jobs Act set to expire at the end of this year, many are wondering: What does this mean for estate planning? In this episode, we break down the possible changes that could take effect on January 1, 2026, and explore strategies to prepare for an uncertain tax landscape. Should you accelerate your gifting? Are certain trusts a smart move? How can stress testing your estate plan help mitigate risk? Join us as we navigate these questions and provide insights to help you protect and optimize your wealth transfer strategy—no matter what lies ahead. Chapters: 0:00 - Introduction 1:40 - Are tax changes coming? 8:06 - How trusts can be leveraged here 13:33 - Key takeaways 16:21 - Closing remarks

Preparing for Your Exit: Key Things to Review Before Going to Market

As more baby boomer business owners reach the age of selling and many entrepreneurs recover from pandemic setbacks, the urgency to execute business transactions has never been greater. However, only a small percentage of owners achieve a truly successful exit. In this episode of Advance Your Wealth, we explore the three critical factors that determine whether a sale will meet expectations: Is the Business Ready? Is the Market Ready? Is the Owner Ready? Homer delves into financial readiness, market conditions, and the often-overlooked mental and emotional preparation required to transition smoothly. If you’re a business owner contemplating an exit, this episode is packed with actionable insights to help you optimize your strategy and secure the best outcome.

Should You Do An Earn-Out When Selling Your Business?

In the latest episode of Advance Your Wealth, Homer Smith explores the complexities of using an earn-out when selling a business. He breaks down how this strategy works, the key benefits—such as maximizing sale value and easing the transition for both buyer and seller—as well as the potential risks, including delayed payments and unforeseen challenges. Whether you're a business owner preparing for an exit or simply looking to better understand this financial tool, Homer provides expert insights to help you make an informed decision. Tune in for a deep dive into the pros and cons of earn-outs and how they might fit into your business transition strategy. Chapters: 0:00 - Introduction 1:30 - What is an Earn-Out? 4:58 - Is an Earn-Out a good fit for you and your business? 11:22 - The level of complexity with Earn-Outs 14:01 - Key takeaways 17:05 - Closing remarks