How Do You Afford This?

Alex Schinasi’s father sketched the first Hulken on a hotel notepad in Paris because he was tired of breaking his shoulders carrying shopping bags. Six years later, Vogue named it the "it" bag of summer, and everyone wants to get their hands on one. Alex is building it toward a hundred million dollar brand with fewer than ten employees and no outside investors. 

She runs it with her husband Johnny, also hosts the Unfinish...

Paige Connell is raising four kids outside Boston and has become a refreshingly transparent voice on what childcare actually costs after posting her own bill on a whim. She's the creator behind She's A Paige Turner, host of the Just Us Girls Pod, and an advocate for affordable childcare and paid leave. 

She and her husband became parents through foster care in 2019, six months before the pandemic, and she has since gone from a ...

Brittany Valdes has been at Microsoft for thirteen years, and in that time she has also built a nonprofit, an AI-powered renovation company with her husband, and an AI academy for women. She is a fourth-generation entrepreneur raising three boys and 23 chickens in Miami.

In this episode, she breaks down how she actually affords the lifestyle, starting with a number almost nobody can name.

Brit and I walk through the household system ...

Claire Wasserman is the founder of Ladies Get Paid, an author, and a career coach with a master's certificate in financial psychology. She bootstrapped her business to seven figures, built a community of over 100,000 women, and got a $300,000 advance for her book. She is also, right now, raising twins in Los Angeles on food stamps. 

In this episode, she sits down with me for the most honest money conversation we have had on thi...

Erika Velazquez Alpern has built the same business twice under the same name. The first time, she shut it down when the math stopped working and went in-house at Morning Brew. The second time, she waited until she had a signed contract in hand, because despite what you may think, many entrepreneurs are risk averse.

She spent her career in brand and media at places like The Guardian and The Boston Globe, and today she is a fractional...

This episode kicks off the sister series. My guest is my little sister Ariel, the person who inspires more of my content than anyone else. She's a homeowner, a sales rep, a mom to my adorable nephew, and living proof that anyone's money story can turn around. Because hers started with a call to tell me the bank was broken. It was not the bank.

Ariel and I relive the full journey, from the negative balance to the $300 that made her f...

Heather Boneparth left a 14-year legal career to go all-in on the wealth management firm she owns with her husband Doug. Together they write The Joint Account, a weekly newsletter helping thousands of couples talk about money, and they're the co-authors of the new book Money Together. 

In this episode, she sits down with me to break down the real numbers behind her career change, raising two kids, and running a family business ...

Viviana Vazquez is the first-gen Latina creator behind OverGenPoverty. She grew up in New York City watching her dad support a family of five on less than $30,000 a year, became the family breadwinner on a teacher's salary, and today she and her husband Xavi have a combined net worth of $510,000. She's a former teacher turned full-time business owner and co-host of the Tech Quiero Más podcast. In this episode, she sits down with me...

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 deal really works from the minimum gu...

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've had on the show.

Helaine and I walk thro...

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 from earning to write her book and be present...

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 Songwriting for Small People,...

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 I walk through the $35,000 wed...

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 affords the lifestyle.

Nicole and I walk...

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 episode, she breaks down how she actual...

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 recent 8-day trip across Dubai, Abu Dhab...

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, an entrepreneur who designed a business that ...