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

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

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

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.

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

In the latest episode of Advance Your Wealth, we explore how tax-aware investment strategies can enhance your long-term wealth planning. While we've previously covered preparing for a business exit and transitioning wealth to heirs and charitable causes, today’s focus is on Private Placement Life Insurance (PPLI)—a powerful tool long utilized by billionaire families and Single Family Offices to mitigate taxes on investment portfolios.

The exciting news? Thanks to advancements in technology and expert guidance, PPLI is now more accessible than ever. Join Homer as he breaks down how this strategy works and how it could be a valuable addition to your financial plan.

Chapters:

0:00 - Introduction

1:49 - What is Private Placement Life Insurance?

6:55 - The industry issues surrounding life insurance

12:22 - The disadvantages of PPLI

19:54 - How to get in touch with Homer's team

22:18 - Closing remarks

In this episode of Advance Your Wealth, we dive deep into the challenges of scaling a business and how to navigate the common pitfalls entrepreneurs face. Joining us is Joe Shrutz, Chief Operating Officer of the PSBLTY Company, who brings a wealth of experience and actionable insights.

Joe shares his expertise on the biggest mistakes business owners make when attempting to scale, from operational inefficiencies to misaligned growth strategies. Together, we explore how to balance ambitious goals with sustainable practices, the importance of building the right team, and the critical role of clear communication during periods of rapid change.

Whether you’re preparing to scale your business or currently navigating the growth phase, this episode is packed with practical advice to help you avoid costly missteps and achieve long-term success.

Chapters:

0:00 - Introduction

1:41 - Growth vs. Scale

9:07 - Distractions

17:47 - Employees thinking like owners

22:20 - Scaling successfully

26:24 - Complimentary Growth Session

28:04 - Closing remarks

On the latest episode of Advance Your Wealth, we dive into the market’s reaction to the recent election results, exploring whether the response was in line with expectations or presented surprises. We discuss the reduced pre-election volatility, the modest post-election market increases, and what this might signal for future trends.

Our conversation delves into the anticipated economic and policy changes under a Trump administration with a Republican-controlled Congress. Key topics include:

• Extensions to Trump-era tax reforms, including the 199A Qualified Business Income Deduction and corporate tax rates.
• Potential adjustments to estate tax exemptions and their implications for wealth management.
• The future of Opportunity Zones and how they might evolve.
• The administration’s strategy for funding tax cuts, including proposed tariffs and their potential economic impacts.

We close by addressing how to navigate these complex changes. Our guest, Homer, shares strategies for cutting through the noise and helping clients make informed decisions during major transitions.

Chapters:

0:00 - Introduction

1:53 - The stock market's response

4:11 - Notable tax law changes

9:21 - Estate tax exemptions

11:50 - Trump's plan to pay for tax cuts

15:21 - Dealing with uncertainty

18:00 - How to contact Homer and his team

18:54 - Closing remarks