Timing, Tax Strategies & Missed Opportunities for Business Owners

In this month's episode of Beyond the Advisor, Nina Breen, CFP®, RICP®, CPWA®, Senior Wealth Planner, and Micah Alsobrook, CPFA®, MBA, Retirement Plan Advisor, continue their fishbowl-style Q&A with a deep dive into the timing, tax strategies, and missed opportunities that quietly shape outcomes for business owners and executives. From estate planning and step-up in basis to 401(k) plan design, business exit timing, donor-advised funds, and weathering market volatility—this episode unpacks the costly decisions that get delayed and the planning moves that change the trajectory.Key Topics Include:Why estate planning is the most delayed financial decision—and the basics every adult needsA real client story on step-up in basis and concentrated employer stockWhen a will isn't enough: the case for a revocable trustSigns a 401(k) was designed to check a box vs. built strategicallyNew comparability profit-sharing as a way to max out owner contributionsDonor-advised funds as a tax play in big-income years (like the year you sell your business)How far in advance to plan a business exit (hint: 5–10 years)Vesting schedules as a key employee retention toolWhat NOT to do when markets get volatile (fear selling, loans, distributions)Fortress Gatewood: the cash + fixed income buffer strategyA real COVID retiree story on confidence in the plan, not the marketTarget date funds and the "evidence-based" investment lineup