Weighing Risk When You're Financially Ahead

Pop quiz: If your health insurance premiums keep climbing, should you just go catastrophic and pocket the savings?

Joe Saul-Sehy, OG, and CFP Anna Allem tackle that exact question, along with a handful of other money decisions that keep Stackers up at night. From navigating healthcare coverage gaps to figuring out when (and how) to withdraw from a 529, this Monday mailbag episode is packed with the practical advice you need, served with the basement humor you've come to expect.

The health insurance conversation gets real: what catastrophic plans actually cover (spoiler: less than you think), how to plan for the gaps, and whether gambling on your health is ever a smart financial move. Then Anna breaks down the 529 withdrawal strategy that saves you headaches at tax time, and the crew tackles a listener who's spooked by market volatility and wondering if it's time to bail.

But it wouldn't be Monday without some chaos—Joe's cat decided to add drama to the morning, Doug brings trivia about counterfeit currency (because of course), and the gang updates you on the charity challenge where Stackers can support financial literacy and maybe win some prizes in the process.

Plus: OG delivers movie reviews to help you figure out what's actually worth your streaming time this week.

What You'll Walk Away With:

• The truth about catastrophic health plans—when they make sense and when they'll leave you exposed

• How to handle healthcare coverage gaps without gambling your financial future

• The smart way to withdraw from a 529 so you don't accidentally trigger taxes or penalties

• Why market volatility isn't a reason to panic—and what to do instead of bailing on your portfolio

• How diversification and rebalancing keep you sane when the headlines get scary

• A reminder that financial planning (like cat wrangling) rarely goes exactly as planned

This Episode Is For You If:

• You're staring at rising health insurance premiums and wondering if there's a better way

• You've got a 529 but aren't sure how to actually use it without screwing up

• Market dips make you nervous and you want to know if you should be doing something

• You're tired of generic financial advice and want real answers to your specific questions

• You believe learning about money should involve at least a few laughs (and maybe some cat stories)

Got a Question for the Basement?

Drop it in the comments or send it our way—you might just hear Joe Saul-Sehy, OG, and Anna tackle it in an upcoming mailbag episode. And if you want to support financial literacy while competing for prizes, check out the charity challenge details in the show.

Deeper dives with curated links, topics, and discussions are in our newsletter, The 201, available at https://www.stackingbenjamins.com/201

Enjoy!

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