In this episode, David sits down with advisor Sean Swanson to explore the SMART planning process and how a comprehensive retirement strategy goes far beyond investments alone. They discuss income planning, tax mitigation, healthcare costs, legacy planning, and the collaborative team approach that helps families navigate retirement with greater confidence and clarity.

David shares highlights from a memorable trip to Washington, D.C., including a lunch with political strategist Carl Rove and reflections on leadership, history, and meaningful connections. The conversation also explores local charitable efforts, the economic impact of the College World Series on Omaha, and why recent market volatility may have more to do with investor behavior and major IPO activity than geopolitical tensions in the Middle East.

David and Chip look into the growing trend of “inheritance bullying,” where adult children pressure parents for early access to family wealth, and why clear estate planning conversations can help prevent future family conflicts. They also unpack the challenges many retirees face after leaving the workforce, including loss of purpose, social connections, and daily structure, while sharing practical ideas for building a fulfilling and meaningful retirement.

Does David support the Trump administration’s proposal for 401(k) accounts to be able to invest in private equity and cryptocurrency? When taking on a new job, am I able to roll over my existing 401(k) or will it have a negative impact? And are there any reasonable health insurance options for someone not part of a big employer plan? David Brooks has answers to these questions in today’s Q&A episode.

Certified Financial Planner Blake Grimm joins David to explore the often-overlooked financial benefits of marriage, from tax savings and Social Security strategies to insurance discounts and retirement planning opportunities. Whether you're considering a first marriage or remarriage later in life, they discuss how understanding the financial implications can help couples make more informed decisions and avoid costly surprises down the road.

David and Chip discuss the latest developments in the ongoing Iran conflict, the continued migration of wealth and businesses away from high-tax states, and what those trends could mean for investors and the broader economy. They also examine Argentina’s surprising economic turnaround under President Javier Milei, highlighting how government spending cuts, regulatory reform, and free-market policies are challenging the predictions of many economists.

David and Chip discuss the soaring costs of the AI revolution, why major companies are struggling to justify massive AI spending, and what it could mean for investors. They also explore why Omaha and Lincoln continue to rank among the best places to raise a family, while examining economic migration trends, business-friendly policies, and the ongoing debate surrounding ESG investing.

What is David’s take on “CDs,” now that they are offering better interest rates? Are “Trump Accounts” for more than just kids? And even with the Pope weighting concerns about AI infringing on human work and dignity, is David still bullish on AI? David Brooks has answers to these questions in today’s Q&A episode.

In this episode, David and Jacob unpack a costly Social Security surprise that blindsided one retiree with a $21,000 repayment notice — and explain why claiming benefits too early can create serious tax and income headaches. They break down the little-known earnings limits, the “special monthly rule,” and why police, firefighters, railroad workers, and other early retirees need a proactive strategy before turning on Social Security.

Today, David reflects on a Memorial Day weekend filled with patriotism, honoring veterans, first responders, and community leaders through events like America’s Wall of Honor and Patriotic Production's Memorial day weekend. The conversation then shifts to the markets, where David breaks down growing concerns around Iran, overheated stock valuations, and rising margin debt — explaining why investors nearing retirement should pay close attention to portfolio risk as markets continue pushing to all-time highs.