
Q&A: Everyone Is Arguing About Roth IRAs And We Have Thoughts
#583: Contrary to recent discussions, Jesse has concluded that a traditional IRA is the smarter way to go for most people once marginal tax rates are factored in. Is he missing something? An anonym...
18 Feb 20251h 3min

The Marriage Contract You Never Saw (But Can't Escape), with Harvard Law Alum Aaron Thomas
#582: They had it all. Six thriving children. A 40-year marriage. A household income of $200,000. Then in her 60s, she discovered a shocking truth: he had gambled away their entire retirement savings...
14 Feb 20251h 29min

When Disaster Hits Home – Literally
#581: Today's question is different. There's something special about it — and you'll understand why in a moment. An 84-year-old listener left us a voicemail about his struggle to break free from mo...
11 Feb 202553min

Treasury Tantrums, Arctic Routes, and McKinley's Ghost
#580: "If you want to understand what's happening in the economy, look at bonds," begins today's episode, where we explore how the bond market acts as a crystal ball for economic trends. The bond mar...
8 Feb 202557min

Q&A: Two Weeks Until My Tenants Move In And I Have Nowhere to Go
#579: Todd is in a real estate bind. He found out six days before closing on a new home that it wasn’t legally sellable. And renters are moving into his current home in two weeks. What should he do? ...
4 Feb 20251h

The Hidden Cost of Playing It Safe With Money, with Dr. Margie Warrell
#578: Fear blocks smart money moves. Ask Harvard Business Review advisor Dr. Margie Warrell, who guides Fortune 500 companies through strategic risk-taking. Her client roster includes NASA, Morgan Sta...
31 Jan 20251h 12min

Q&A: The Efficient Frontier Was Perfect Until HR Got Involved
#577: Kelsey is excited about investing along the efficient frontier, but it feels impossible with the lack of fund options in her employer-sponsored 401k. What’s the best way to deal with this proble...
28 Jan 202559min

The World's Richest People Are Weird by Design, with William Green
#576: The world's greatest investors have a secret: they're weird. When one young fund manager met Bill Miller for the first time, he refused to shake hands. Instead, he locked eyes and declared: "I...
24 Jan 20251h 21min




















