How Do You Afford This?

Jared Freid is a stand-up comedian, host of The JTrain and U Up? Podcasts, the author of his new book Walking Red Flag and his special, 37 & Single, hit the Netflix top 10. In this episode, he breaks down how he actually affords the life of a working comedian. Jared and I get into the real economics of comedy: why he funded his own specials out of pocket and what each cost him, how a touring d...

Helaine Knapp is a serial entrepreneur, the author of Making Waves , and the host of the Step Into Next podcast. She founded CityRow, the rowing-based fitness brand that landed in studios across the country and homes around the world, and now splits her life between Austin and New York. In this episode, she breaks down how she affords it, starting with the most honest founder money story we'v...

Stefanie O'Connell is an award-winning journalist and the author of The Ambition Penalty . She has run her own business for a decade, and is now doing it while raising a toddler in NYC. But this episode is a little different, because Stefanie isn't here to say she has it all figured out. She sits down with me to break down how she is affording a season where she deliberately stepped back...

Rachel Lipson takes 12 to 15 trips a year with her family of four, her kids have visited 25 countries and they haven’t even finished elementary school, and she lives in one of the most expensive zip codes in the country. She’s the founder of The Point, a best-selling Substack and consulting business that teaches families how to travel using credit card points and the founder of Blue Balloon Songwr...

Jen Glantz has built an empire around love stories without actually liking weddings. She’s the founder of Bridesmaid for Hire, host of the 1-800-Bridesmaid podcast, and author of multiple books including her newest, Finally the Bride . In this episode, she breaks down the numbers behind her own wedding, her clients' weddings, running multiple businesses and raising a daughter in NYC.  Jen and...

Nicole Giordano spends three months a year living in Europe, owns her home, and works thirty hours a week in a career she loves. She's the founder of Midlife Creative Studio and a long-time online entrepreneur who has spent the last decade designing a life around what actually matters to her, thoughtfully and strategically. In this episode, she sits down with me to break down how she actually...

Ashley Torres spends three months per year in a new country with her family, takes five other trips a year, salsas with her friends one to three times a week, and runs multiple businesses. She's been a full-time content creator for over 15 years, writes about her family’s travels on Substack, is the co-founder of LA Girl Dinner Club, and wants us all to live life to the fullest. In this episo...

Ally Case has traveled to 58 countries and takes around 12 international trips a year. She's a content creator, part-time flight attendant, and the CEO of digital marketing agency Uppercase Media, which she runs with a team of five. In our very first episode, she sits down with me to break down how she actually affords the lifestyle.  Ally and I walk through exactly what she spent on her rece...

A first listen at How Do You Afford This?, launching this June. 👀 Ashley Feinstein Gerstley, CFP® and founder of The Fiscal Femme, sits down with real people and asks the question everyone's wondering - how do they actually afford their lives? In season one, you'll hear from a content creator with five income streams, a bridesmaid-for-hire who pulled off her own wedding for under $2,000...