Tis the season for… open enrollment! Dennis and Stephanie dive into the thrilling, gut-wrenching world of health insurance like it’s the season finale of a reality show you didn’t know you were starring in. From why every employer seems to pick the most random renewal dates, to why your “perfect plan” doesn’t exist (sorry), they break down the madness with humor, sarcasm, and a sprinkle of “I told you so.”

You’ll laugh, you’ll cry, you’ll probably check your deductible halfway through. Whether you’re an employee wondering why your premiums rival your mortgage, or a business owner trying to keep your sanity (and your staff), this episode will make you feel slightly better about it all.

Call it therapy, call it education — just don’t call your agent without listening first.

Chapters:

00:00 - We Switched Seats (and Immediately Regretted It)

02:00 - Why Is Open Enrollment Always When You’re Broke?

03:40 - The Government Picked These Dates for Fun

05:20 - January 1st: New Year, Same Deductible

07:00 - Health Insurance: More Complicated Than Dating Apps

09:20 - The Myth of the “Perfect Plan” (Spoiler: It Doesn’t Exist)

10:05 - When Your Premium Costs More Than Your Mortgage

12:00 - Agents Who Send You 100-Page PDFs and Call It “Service”

14:00 - “My Kid Turned 26 — Now I’m Poorer, Somehow”

16:00 - The 2026 Contribution Crisis (a.k.a. Why Everything Costs More)

18:30 - Call Your Agent (Unless It’s Dennis — He’s Busy)

21:00 - Politicians, Subsidies, and Other Scary Words

22:40 - Accountants Are Terrifying (Ben Affleck Approved)

23:30 - Shameless Plug and Final Thoughts

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