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How Do You Afford This?
How Do You Afford This? answers the question everyone is already wondering: how do people actually afford their lives?
Ashley Feinstein Gerstley, CFP®, founder of the Fiscal Femme and award-winning author is on a mission to find out and bring you along for the ride.
Each episode takes the inspirational, and makes it tangible. Whether that’s international travel, buying a dream home, raising a family, a fabulous wardrobe, or building a million dollar business, Ashley and her guests will break down the numbers - what it costs, how they make it work, and the financial strategies behind the lifestyle.
It’s part voyeuristic, part practical, and completely judgment-free. Come for the tea. Leave with a financial blueprint to start building your dream life.
Episodes
18 episodes
#17: It Took Almost 10 Years Before She Earned Six Figures
Priya Malani spent 2013 feeding two people on forty dollars a week so she could keep building a company nobody had asked for yet. Fourteen years in, Stash Wealth has worked with thousands of what she calls HENRYs, high earners not rich yet, and...
#16: She's Building a $100M Brand From Lisbon With 3 Kids
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...
#15: Her $70K a Year Childcare Bill Went Viral
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 Po...
#14: What the Mother of AI Is Teaching Her Kids About Money
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 boy...
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#13: She Built a Seven-Figure Business. Now She's Rebuilding From $150K in Debt
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 a...
#12: She Left a Six-Figure Salary. Her First Client Paid More Than the Job Did
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,...
#11: She Called Me to Say the Bank Was Broken. Now She Has Six Figures Saved
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 c...
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#10: She Resented Her Husband. Then She Left a $200K Salary to Join Their Family Firm
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 c...
#09: From Poverty to a $510K Net Worth: How This First-Gen Eldest Daughter Made It Happen
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 he...
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#08: The Finances Behind a Top 10 Netflix Comedy Special
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...
#07: This Founder Raised $20M. The Exit Was a Zero
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...
#06: The $100K She Saved To Fund Her Book and First Years of Motherhood
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 St...
#05: $143K Worth of Family Travel Using Credit Card Points (In One Year)
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 Th...
#04: Her Money Blueprint: Living Abroad With a Kindergartener
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 year...
#03: She Works 30 Hours a Week and Affords 3 Months in Europe
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 desi...
#02: The Real Cost of Weddings, From a 200-Time Bridesmaid
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. ...
#01: The Finances Behind the 12 International Trips She Takes Per Year
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...
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