How Do You Afford This?

25 Episodes

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#24: She Paid $95 for a Trunk. She Was Offered $30K

2026-10-2801:02:06

Virginia Chamlee was raised from six weeks old by a grandmother who bid on lost shipping containers at the Jacksonville port and sold the furniture off their front lawn. She’s now an artist and a writer, which are two of the least predictable ways to make a living, and she has somewhere around nine income streams she mostly never planned for. She’s the author of Big Thrift Energy, now in its fourth printing, she still writes for People magazine, her art is sold at Anthropologie and Chai...

#23: He Googled "How to Be a Great Husband." Then She Got a Global Promotion.

2026-10-2151:03

Brian Page spent fifteen years working eighty hour weeks while his wife ran most everything at home. Then they traded places. She went all in on her career, he took over the entire household, and they moved the family twice for her job. He is the founder of Modern Husbands, a Certified Financial Therapist and an Accredited Financial Counselor, and in this episode he sits down with me to break down how they actually afford it. Brian and I walk through the household income that funded all...

#22: Her Netflix Show Won an Emmy. She Still Paid for Her Own Ticket.

2026-10-1455:23

Jess Banks makes tables that float in midair and sell for up to $60,000. She has two engineering degrees from MIT, she is a physicist and roboticist turned inventor, she founded the kinetic furniture company Rock Paper Robot, and she co-hosts the Emmy Award-winning Netflix show Hack My Home. She has also closed the company, licensed the table to someone who has not sold one in years, and does not own one herself. In this episode she sits down with me to break down how she actually affords her...

#21: How She Got Matt Damon for $800

2026-10-0757:35

Jill Kargman has written twelve books, created and starred in the Bravo series Odd Mom Out, co-produced a Tony-nominated revival of Cabaret, and just made her first feature film. Influenced is a satire of Upper East Side momfluencers that she wrote and stars in as Dzanielle, with appearances from Drew Barrymore, Gwyneth Paltrow, and Matt Damon. It is streaming now. She raised three kids on the Upper East Side, inside the exact world she has spent her career poking fun at. In this episode she ...

#20: Her $305K Overhaul of a $2 Million Apartment in NYC

2026-09-3001:00:21

Laura is a corporate executive who has spent seventeen years at the same company. Her husband is a prosecutor at the Manhattan DA's office, and they are raising three daughters in Tribeca. She is also one of my best friends, and has never talked about her money publicly before. In this episode, she sits down with me to break down how she actually affords the lifestyle. Laura and I walk through the $2.05 million apartment they bought two years ago and the $9,000 a month in charges that come wi...

#box-pro-ellipsis-179356966031870{-webkit-line-clamp:2;}How Do You Afford This?