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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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After two years at Fetch’s job, we finally decided to invest in the 403(b). In this episode, we walk you through why we waited, what changed, and how we’re making the decision now — with a little help from ChatGPT.
You’ll hear:
• How our FIRE journey shifted our perspective on tax-advantaged accounts
• Why we passed on the 403(b) at first (and what we misunderstood back then)
• What helped us rethink the “Middle Class Trap” and early access fears
• How we used ChatGPT to analyze Fidelity fund options and match them to our existing portfolio
• The real trade-offs between SEP and 403(b), especially around flexibility and paycheck deductions
We also reflect on how far we’ve come — from confusion about tax filing status to confidently talking portfolio allocations and contribution maxes.
Whether you’re navigating multiple retirement accounts, thinking about Coast FI, or just figuring out where to stash your next investment dollar, this episode gives you a grounded, real-life look at how we’re making it all work.
Check out our Resource Doc:
And our IG account @tryingforfi
18 episodes
