In this playful and insightful episode, Don and Tom explore how the beloved Friends characters might fare financially if they were retiring today. Using their signature mix of humor and practical investing wisdom, they analyze each character’s fictional career, personality, and spending habits to project their retirement readiness. The second half of the show returns to real-world money matters, answering listener questions about blending withdrawal strategies and fund choices in employer retirement plans.
0:04 Why this episode starts with a Friends reference—and yes, it’s copyright-friendly
0:31 Monica and Chandler Bing as retirement savers: organized, driven, but maybe too perfectionist
3:25 Monica’s obsessive planning vs. Chandler’s possible risk aversion
4:22 Overthinking portfolios and the emotional toll of too much tweaking
5:01 Savers who struggle to spend: how Monica might hoard instead of enjoy
5:56 Chandler’s likely financial behavior and their combined million-plus portfolio
7:03 Ross: neurotic, divorced, and probably pension-supported
7:54 Why pensions are psychologically powerful for retirees
8:35 Ross would need an advisor to keep him calm and invested
9:14 Rachel: spender, low earner, fashion industry job—not retirement ready
10:30 Joey: the actor’s feast-or-famine finances and SAG-AFTRA pension potential
12:22 Real SAG-AFTRA pension expectations: modest but helpful
13:09 Joey’s likely retirement: modest income, limited comfort outside major cities
13:54 Phoebe: quirky, lovable… financially reckless?
14:28 Phoebe’s imaginary downfall: alimony, bad investing, busking in Times Square
15:20 Big picture takeaways: personality, income, and circumstance aren’t destiny—but they shape outcomes
16:48 The Bings win the retirement game… Phoebe’s husband probably doesn’t stay married
17:30 Listener Q1: Combining fixed and flexible withdrawal strategies
18:52 30-year portfolio simulation using 60/40 and AI tools
20:24 Hybrid strategy results: high survival rate, smoother ride, and growing payouts
21:21 Comparison of 4% vs. 5% withdrawal income over time
22:36 Listener Q2: Replacing expensive international funds in a union 401k plan
24:00 Replace EuroPacific and Developed with Fidelity’s low-cost international index fund
25:17 Expense ratio showdown: PigWX vs. FSPSX
26:32 Closing chaos: how to contact Tom and the long-lost newsletter phone number
27:49 Origins of 800-FUND-004 and how someone just walked into the Bellevue office
29:42 End credits and final laughs—yes, even Tom held back the dad jokes (mostly)
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