Christine shares the backstory of her blog, The DB-ification Trend and the movement toward increased employer control versus employee discretion of defined contribution retirement plans to better provide a sustainable source of income during retirement, along with the one provision she would change with a magic retirement wand, if she could.

Sharing the current funding concerns and potential future reforms for Social Security, Mary Beth provides tips on when to claim and when to delay Social Security benefits in order to maximize value—particularly in the current low-interest rate environment. She also highlights the specific need for women to carefully consider their Social Security claiming strategy to ensure sufficient retirement income.

Episode 22

Episode 21 Deep Dive—Injecting Surf-Shop Energy into 401(k) Land

Host Mike Webb sits down with J.D. Carlson—former pro-surfer, onetime beach-town retailer, and now CEO of TPA firm Plan Design Consultants—to unpack how the four-man Retireholi(k)s crew turned a dry subject into appointment viewing for advisors.

How a Surfboard Became a Compliance Manual

Growing up steps from the Pacific, Carlson lived the surf-bum dream until family finances nudged him into his father’s 1970s-era third-party administration business.

Once he grasped the back-office rigor—plan documents, nondiscrimination tests, Form 5500s—he applied skate-shop branding tactics: hoodies over suits, Nerf-golf in the office, and candid client talks that ditch ERISA jargon.

The Case for Specialist TPAs—Even in Mega-Plans

Many advisors still assume TPAs belong only in the micro-plan market. Carlson argues the opposite: his happiest clients often manage hundreds of millions in assets and need bespoke testing, controlled-group consulting, and rapid document updates that bundled recordkeepers struggle to deliver.

His litmus test for sponsors: don’t choose “bundled vs. unbundled”; vet who is doing the compliance work, what their checks-and-balances look like, and how quickly they adapt to legislative change.

Why Retireholi(k)s Works

Takeaways for Plan Sponsors & Advisors

Ary Rosenbaum practices ERISA and retirement plan law at The Rosenbaum Law Firm P.C. and is also known by industry insiders as That 401(k) Guy, infusing personality into his practice through his That 401(k) Site website, conference series, and podcast.

In episode 20 of Revamping Retirement, Mike Webb chats with Ary about his perspective on topics such as the DOL’s Fiduciary Rule and ESG and Private Equity in retirement plans, his wish list for compliance changes to help plan sponsors avoid plan errors, and his collection of Mets memorabilia.

Making Retirement Plans Relatable

Ary Rosenbaum isn’t your average ERISA attorney. In this episode, Mike Webb explores what sets Ary apart—from his unconventional entry point into retirement plan education to his knack for blending pop culture with plan compliance. Whether he’s writing about disaster movies or sharing Caddyshack references, Ary uses his That 401(k) Site platform to demystify complex retirement topics through humor, storytelling, and real-world connections.

The Value of Connection in Compliance

Ary shares that retirement plan law is, at its core, a relationship business. His mission? To humanize the legal landscape by writing and speaking in language plan sponsors actually understand. That includes poking fun at industry jargon and sharing personal experiences from his days as a junior associate trying to break into the space. Listeners also get a taste of Ary’s love for nostalgia and how cultural references—from network TV promos to Mets memorabilia—help him make lasting connections with clients and peers.

What’s Next in the World of ERISA?

The episode dives into the regulatory fast pace at the Department of Labor, especially around fiduciary rules, ESG investments, and private equity in retirement plans. Ary weighs in on what’s worth paying attention to, and what might be more politics than policy. He also offers his take on improving plan compliance, including why he’d revise the definition of highly compensated employees and simplify compensation rules to help reduce plan errors.

FIRE (Financial Independence, Retire Early) is a lifestyle movement that embraces the goal of achieving financial independence by decreasing spending and increasing income.

Mike and J.Money discuss why now, in the middle of a pandemic and recession, individuals may want to consider adopting some of the key FIRE tenants. Will the pandemic light a flame for future FIRE movement participants?

One option, growing in popularity among retirement plan sponsors, is to offer an emergency savings account through the retirement plan recordkeeper. But are these sidecar accounts the best approach?

In episode 18 of Revamping Retirement, Mike Webb and Jack Towarnicky of the American Retirement Association discuss differing views over utilizing sidecar accounts for emergency savings.

Episode 18

In episode 17 of Revamping Retirement, Mike Webb discusses the statistical case for adopting auto enrollment, as well as how finding the sweet spot for default deferrals and auto escalation can help improve participants’ retirement readiness.

Reassurance Amid Market Uncertainty

While episode 17 of Revamping Retirement centers on the importance of automatic enrollment and smart plan design, host Mike Webb also takes the opportunity to address a pressing issue affecting retirement savers everywhere: the impact of market volatility in the wake of the COVID-19 pandemic.

As fear and uncertainty ripple through the markets, Webb offers a grounded perspective. Drawing on historical data and behavioral finance principles, he reminds listeners that downturns—while uncomfortable—are a normal part of the investing journey. Using the early 2020 market drop as a backdrop, he compares it to the 2007–2009 financial crisis and shares strategies to keep long-term savers focused on what really matters.

Why the Stock Market Isn’t the Whole Story

Webb walks listeners through a simple scenario to highlight a powerful insight: early-career investors are often more affected by their contribution behavior than by market performance. Even in a hypothetical situation where the market drops by 50% two years in a row, participants who continue making regular contributions can still see positive asset growth. Thanks to dollar-cost averaging and the long time horizon most savers have before retirement, market downturns can actually create buying opportunities that pay off down the road.

This approach not only reframes fear, but also empowers savers with a message they don’t often hear: it’s not about timing the market—it’s about time in the market.

A Role for Plan Sponsors and Advisors

In addition to reassuring participants, Webb also urges plan sponsors to reinforce these fundamentals. Automatic enrollment, default deferral rates, and auto-escalation features can nudge participants toward better long-term outcomes—especially during uncertain times. Encouragingly, these tools work best when paired with clear, human-centered communication that helps participants stay the course.

Ultimately, Webb’s message is both strategic and empathetic: stay invested, keep contributing, and don’t let short-term volatility derail a long-term plan. For plan sponsors and fiduciaries looking to guide participants through uncertain times, this episode offers a timely reminder that education, structure, and trust can go a long way.

Mike Webb gets back to the basics to discuss the two primary types of target date funds—off the shelf and customized—and shares the key components used to evaluate these investments.

However, the nuances of three of the provisions may have some unintended consequences. In episode 15 of Revamping Retirement, Mike Webb discusses the potential issues with these CARES Act provisions.

Staying the Course During Market Volatility

In episode 14 of Revamping Retirement, host Mike Webb shares timely insights on the financial uncertainty brought on by the COVID-19 pandemic—particularly as it relates to retirement savers. With markets reeling from historic drops, Webb offers a measured, optimistic perspective that helps plan sponsors and participants alike keep things in perspective.

What Happens When the Market Drops?

Using relatable hypotheticals and past market data, Webb explains how even steep downturns—like the 26% drop from the Dow’s February 2020 peak—don’t necessarily derail long-term retirement outcomes. For early- and mid-career savers, consistent contributions and strategies like dollar-cost averaging often matter more than short-term investment performance. Even during bear markets, saving steadily can lead to positive outcomes over time.

Why Consistent Saving Still Wins

Webb drives home the idea that “biggest balance wins”—and that retirement success is driven less by timing the market and more by staying in it. He reminds listeners that downturns are temporary, and markets have historically recovered within a few years. Meanwhile, savers who remain disciplined and continue to invest during low points often benefit from compounding and growth when markets rebound.

A Realistic Yet Hopeful Message

Throughout the episode, Webb balances realism with encouragement. While acknowledging the legitimate anxiety many investors feel, he discourages panic-driven decisions. Instead, he urges listeners to stay the course, review their goals, and—if possible—save more. His message is simple: whether in a bear or bull market, consistent saving and long-term thinking remain the cornerstones of a strong retirement strategy.

This episode serves as both a market update and a motivational guide, helping listeners navigate the emotional and financial impact of crisis-driven volatility.