The Small-Business Playbook: Strategy, Taxes, and Timing | The Informed Investor 42

Episode 42: What happens to your life—and your wealth—when the business you built becomes one of your biggest risks? We dive deep into the unique challenges facing small-business owners who are navigating growth, managing their own wealth, and planning for an eventual exit. Featuring insights from Pat Collins and Michael Goodman, two seasoned professionals at Greenspring Advisors, this conversation tackles the critical intersection between personal financial planning and business strategy. You’ll hear why so many small-business owners delay succession planning, and how that hesitation can limit future options. From the “silver tsunami” of retiring owners to the emotional complexities of letting go, they explore why exit planning isn’t just a financial decision—it’s a personal one. They also break down the most common pitfalls, including overreliance on a single asset (your business), lack of diversification, and gaps in risk management like insurance and tax planning. You’ll also learn practical strategies to increase business value, prepare for a successful transition, and build a coordinated team of advisors (from CPAs to attorneys) to help guide the process. But numbers only tell part of the story. Pat and Michael also examine the behavioral side of exit planning: identity, purpose, and what life looks like after the deal is done. Whether it’s consulting, philanthropy, or rediscovering passions, we explore how to prepare for the next chapter in life. In Episode 42 of The Informed Investor, Dimensional’s Mark Gochnour, Head of Global Client Services, sits down with Pat Collins and Michael Goodman from Greenspring Advisors. In addition to their discussion about running and selling a small business, they also touch on smart retirement strategies, including how much income you should save and the need for flexibility between traditional and Roth accounts. Whether you’re a small-business owner thinking about selling—or just starting to plan—this episode offers key insights to help you maximize not just your exit, but life beyond it. TIME STAMPS 00:00 Intro 02:08 Headlines 03:05 Small-business owners 04:05 Financial planning concerns 05:06 Concentration of wealth 07:20 Two types of owners 08:58 The E-Myth Revisited 09:58 Insurance and taxes 11:32 Emotions vs. business 13:15 Planning for an exit 15:17 Team of experts 16:35 Who to sell to? 18:45 Life after selling 22:54 Money after selling 23:57 Living your best life 26:07 Key tips for owners 26:52 Retirement planning 29:24 Roth conversions 31:43 What to ask an advisor LINKS FROM TODAY’S EPISODE:  The Informed Investor: Feedback Survey https://www.dimensional.com/us-en/inf... “The Informed Investor” on YouTube    • The Informed Investor   Dimensional Fund Advisors Shorts on YouTube    / @dimensionalfundadvisors   Mark Gochnour on LinkedIn   / mark-gochnour-9a23598a   Michael Goodman on LinkedIn   / michaelgoodman3   Pat Collins on LinkedIn   / j-patrick-collins   Learn more at https://www.dimensional.com/ #smallbusiness #greenspring #exitplanning #successionplanning #wealthconcentration #taxmanagement #estateplanning #estatetax #retirement #401kplan #401kmatch #rothira #rothconverstion #financialadvisors #dimensionalfundadvisors #dimensional #dfa