Episode 28

In episode 28 of Revamping Retirement, Mike Webb passes the hosting torch to Jennifer Doss and Scott Matheson, who lead the employer-sponsored retirement plan practice at CAPTRUST. The two discuss CAPTRUST’s recent fee benchmarking webinar, including the future of fees, structuring fees to make retirement plans more attractive, and what tops the list of fee-related concern for plan sponsors.

Later, Mike Webb shares what plan sponsors need to know about pooled employer plans, or PEPs, in Minute with Mike. To close out the episode, Doss and Matheson are joined by lead investment strategist Sam Kirby to recap the markets, discuss what’s on the minds of plan sponsors, and talk about the retirement tools that can hedge against inflation risk.

Nevin Adams serves as a prolific author of ARA’s publications. Adams has gained notoriety for correcting many of the common retirement misconceptions perpetuated by the media—an area of increasing concern as social media recirculation ramps up. Tune in to hear more about retirement myths and other key issues, such as coverage availability, state run auto IRAs, and automatic enrollment.

With more than 35 years of experience practicing employee benefits law, Bob Toth is an expert to the experts—particularly in the areas of 403(b) plans and annuity products. Webb and Toth discuss the key to moving the needle on annuities, including how to effectively communicate the benefits of these products, the importance of pricing opaqueness, and how the Setting Every Community Up for Retirement Enhancement (SECURE) Act provision allowing portability may help address participant concerns. Toth also shares some of the new products being developed in the marketplace and explains why beer is essential to solving the annuity puzzle.

Episode 25

With more than a decade worth of plan sponsors questions answered by industry experts, the column continues to be one of the most popular features on PLANSPONSOR’s website. Mike, David, and Rebecca share the history of the column, contributing factors to its success, and tips on how plan sponsors can have their questions featured.

Inside Episode 24—Keeping “Ask the Experts” a Must-Read After 12 Years

Host Mike Webb joins PLANSPONSOR managing editor Rebecca Moore and Groom Law Group principal David Levine for a behind-the-scenes look at one of the industry’s most enduring Q&A columns.

How It Began

In 2008 the IRS overhauled 403(b) regulations, and PLANSPONSOR’s then-editor suspected plan sponsors would be hungry for guidance.

Moore launched a niche newsletter—B-Lines Ask the Experts—with Levine and fellow attorney David Powell fielding reader questions about the new rules.

The feature quickly outgrew its 403(b) roots; today it addresses 401(k), 457, and DB questions and is surfaced site-wide on PLANSPONSOR.com.

Why It Still Resonates

Bread-and-butter practicality: Columns tackle evergreen issues (vesting errors, controlled-group testing, hardship distributions) that plague sponsors of every size.

Strict editorial filters: Questions must be broad enough to help many readers and devoid of personal or client-specific details—a guardrail that keeps content legally safe and universally useful.

A rotating expert bench: Beyond Levine and Webb, Groom attorneys Kim Boberg, David Powell, and Charles Phillips now share the weekly load, ensuring fresh perspectives and on-time answers.

Think universally. Situations that could apply to thousands of plans—rather than one quirky fact pattern—rise to the top.

Skip the sensitive data. No participant names, Social Security numbers, or proprietary plan details.

Keep it concise. A well-framed paragraph outlining the issue and why it matters helps editors gauge fit quickly.

Fun Facts

The column’s archive spans more than 600 posts and still ranks among PLANSPONSOR’s highest-clicked items each week.

Popularity spawned a 403(b) e-book—Your 403(b) Questions Answered—compiling the most timeless entries for easy reference.

“Jump-the-shark” moment? Not yet—web traffic indicates readership is still climbing.

Whether you’re troubleshooting a nondiscrimination failure or clarifying SECURE 2.0 nuances, this episode explains how to leverage the Ask the Experts pipeline—and why its mix of legal rigor and plain-English exposition keeps plan sponsors coming back.

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?