Overtime Earnings

Most entrepreneurs know how to compete but are they operating with a coordinated tax strategy, or simply reacting after the season ends?

In this episode Ken Handy and David Baker use the language of sports to make tax planning more approachable. They discuss why entrepreneurs may benefit from treating their tax advisor like a coach, watching important deadlines, coordinating across their professional team, and balancing offensive opportunities with defensive planning. PPG-8888313.1(06/26)(exp.06/30)

Five years from retirement is an unusual place to be. The finish line is close enough to feel real but there may still be time to change the game plan. In this episode we discuss why this five-year window can be so important. We also explore the questions that often surface as retirement moves from a distant idea to a real-life transition and why a retirement plan needs to account for real life, not simply an ideal scenario on paper. PPG-8885979.1(05/26)(exp.05/30)

Everyone wants to know the secret to successful investing. Is it stock picking? Timing the market? Finding the next big opportunity before everyone else? In this episode Dave and Ken reveal the one characteristic they've consistently seen in investors who build lasting wealth and it's probably not what you think. PPG-8914094.1(06/26)(exp.06/30)

In this special market update, Ken and Dave sit down with Michael Lieberman, Partner at Advisors Capital Management (ACM), to break down what has been an eventful first half of 2026.

Mike shares insights from ACM's portfolio management team, and offers his outlook for the remainder of 2026 and beyond. This episode delivers practical insights and long-term perspective for investors navigating today's markets. PPG-9016460.1 (07/26)(exp.07/30)

After years of uncertainty surrounding tax legislation and planning strategies, families may finally have something rare: clarity. Ken and Dave discuss why a more predictable tax environment creates opportunities for smarter planning, stronger family communication, and more effective multigenerational wealth strategies. Drawing on sports analogies and real-world client experiences, they explain why proactive planning often leads to better outcomes than last-minute decisions. PPG-8925096.1(05/26)(exp.05/30)

In Part 2 of this two-part series, Ken Handy and Dave Baker go deeper into the real differentiators between average advisors and elite financial planners. This episode explores how true financial planning extends far beyond portfolios and into family dynamics, legacy conversations, and the evolving role of technology like AI. PPG-8943526.1(06/26)(exp.06/30)

In this episode, Ken & Dave pull back the curtain on the financial planning industry to reveal what truly separates elite advisors from the rest. From credentials and experience to philosophy and client-first planning, this conversation is packed with insights to help you make smarter financial decisions. PPG-8942625.1(06/26)(exp.06/30)

Ken and Dave sit down with estate planning attorney Kristen Lohmeyer, founder of Ally Legal Planning. Together, they break down the essentials of estate planning. The conversation highlights a critical truth: estate planning isn’t just about what happens after you pass. It’s about protecting yourself, your family, and your assets while you’re alive. PPG-8955249.1 (06/26)(exp.06/30)

Dave and Ken discuss why financial planning for families raising children with special needs requires a different playbook. This topic is one that is very close to both of your hosts. They cover SSI and Medicaid resource limits to ABLE accounts, special needs trusts, beneficiary designations, and caregiver planning. Ken and Dave also walk through the key decisions families should understand before gifting assets, naming beneficiaries, or building long-term support plans. PPG-8886779.1(05/26)(exp.05/30)

Ken Handy and Dave Baker discuss one of the most overlooked retirement risks facing married couples: the “widow penalty.” They define the term and share details that are important in the planning process to ensure you've accounted for the surviving spouse. PPG-8852000.1(05/26)(exp.05/30)