Episode 21: Making Retirement Cool – J.D. Carlson & Retireholi(k)s
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
- Weekly YouTube shows mix technical segments (SECURE 2.0, fee litigation) with beer reviews and game-show trivia—proving retirement talk can be both accurate and genuinely entertaining.
- Industry luminaries such as ERISA attorney Fred Reish appear in hoodies, reminding viewers that even legends are real people.
Takeaways for Plan Sponsors & Advisors
- Authenticity attracts attention. Employees tune out boilerplate but engage when content feels human.
- Evaluate compliance depth, not just platform convenience. A nimble TPA can add value well beyond small-plan administration.
- Education before entertainment still wins. Humor lands because the technical foundation is solid.
- Stream the full conversation to hear Carlson’s marketing tips, surfer-to-CEO journey, and why he thinks every committee meeting could use a little craft-beer energy.