Retire SMART Podcast

Jacob Orand returns to break down the complexities of Medicare’s IRMAA penalties and how the SSA-44 form can help retirees push back on unexpected costs tied to a life-changing event. From sneaky Medicare Advantage fees to the IRS’s two-year income lookback, the team unpacks what proactive retirees need to know. Bonus: a few laughs about government bureaucracy and Ghostbusters along the way.

We kick off today’s episode by celebrating Chip Maxwell’s five-year anniversary at Retire SMART, reflecting on the firm’s growth from humble beginnings to a thriving, 40+ person team. The conversation then shifts to current market dynamics and what they could mean for investors heading into the second half of the year. Tune in for a mix of reflection, strategy, and forward-looking insights.

Today, we dive into the surprising uptick in consumer confidence and what it could mean for short-term spending—and why that optimism might be short-lived. From Manpower Group’s dividend cut to rising delinquency rates and early signs of stress in the housing market, we explore the growing disconnect between consumer sentiment and economic reality.

Is it possible for David to drive a client’s tax burden down to zero in retirement? Is the best way to keep my assets safe to get out of the markets, once I retire? And does Retire SMART use the benchmark of one’s 401(k) should be 10 times larger than your annual salary? David Brooks has answers to these questions in today’s Q&A episode.

David Brooks and Sean Swanson unpack the top questions they get about Social Security, including whether the program will still be around and the best time to claim your benefits. They also discuss the upcoming “Social Security Blueprint” class, designed to help retirees and pre-retirees make confident, informed decisions about their benefits.

David shares an exciting behind-the-scenes look at his recent visit to the Chicago Board Options Exchange, where he rang the closing bell to celebrate the launch of a new ETF. The conversation then shifts to Washington, as David and Chip break down the latest developments in Trump’s spending bill, fiscal responsibility, and the political roadblocks preventing meaningful debt reform.

David dives into Ray Dalio's stark warning about U.S. treasuries and the mounting global debt crisis, with insights into what Moody’s downgrade means for taxpayers and markets. Plus, a cautionary tale out of New Jersey—how a tiny deli became the centerpiece of a $100 million fraud, and what it teaches us about risk and responsible investing.

After a recent purchase with a surprising result on the receipt, has the “tariff fee” become a common practice in the retail market? And if I feel that I’m set with my pension and full-retirement social security, do I really need to hire an advisor if they’re likely going to just tell me to stay the course? David Brooks has answers to these questions in today’s Q&A episode.

David is joined by Josh Cheatle, Retire SMART’s new Director of Wealth Management, to talk about what it takes to grow a firm the right way—from building culture and leadership to developing a deep bench of skilled advisors. We’ll share how a nationwide search led us to a surprising local connection, and how Josh is helping shape the future of our team and client experience.

David and Chip look into Omaha's surprising mayoral election outcome, where John Ewing unseated incumbent Jean Stothert, and what that could mean for the city’s future. They also explore the latest developments in tax legislation, SALT deduction debates, and why some market optimism might be premature according to JP Morgan’s Jamie Dimon.

Will schools in states with NIL exemptions, or no state income taxes, have an advantage on landing football recruits over states that don’t? Does the election of a new pope impact financial markets? And should I or should I not own my own life insurance policy? David Brooks has answers to these questions in today’s Q&A episode.

We’re joined by Bill Williams from Patriotic Productions — the team behind the powerful Honor Flights and the national Remembering Our Fallen memorial. From flying thousands of veterans to D.C. to honoring 5,500 service members lost since 9/11, Bill shares how he and his wife are keeping the legacy of our heroes alive. This is a conversation about remembrance, gratitude, and impact.

From the newly announced U.S.-UK trade deal to shifting dynamics in the U.S.-China relationship, we explore the market’s reaction to recent announcements, including Trump’s proposed executive order targeting pharmaceutical pricing. Is the administration’s tariff strategy finally paying off? And what could lower drug prices mean for American consumers? Here is David’s take.

David and Chip investigate the shifting landscape of the U.S. housing market, highlighting growing concerns from home builders and a surge in excess inventory—especially in Florida. The conversation also touches on economic cycles, historical comparisons to 2007, and the return of home builder incentives. From real estate trends to labor economics, this episode is a data-driven look at current market realities.

What is David’s take on the “Oracle of Omaha” officially announcing his retirement at the end of 2025? And with Congress back in session, what are the prospects for the Trump tax cuts of 2017 being extended or made permanent? David Brooks has answers to these questions in today’s Q&A episode.

Nebraska’s inheritance tax may finally be changing—estate planning attorney Colin Kastrick, with Kastrick Law, joins us to break down the latest proposal, what it means for beneficiaries, and why getting your documents right matters more than ever, especially in blended families."

On today’s episode, David shares exciting news: Retire SMART is now an official sponsor of Nebraska Cornhusker Athletics. We also look at April's surprising job numbers, discuss concerning jobless claims data, and revisit Warren Buffett’s historic stance on trade deficits in light of current tariff debates. Plus, China's economic struggles and what it all means for investors.