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How Do You Afford This?

How Do You Afford This?

Written by: Ashley Feinstein Gerstley
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About this listen

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.

© 2026 How Do You Afford This?
Self-Help Success
Episodes
  • #25: She Made $42K at a Nonprofit. Now She Funds Her Own Movement
    Nov 4 2026

    Eve Rodsky grew up on food stamps in Stuyvesant Town, raised by a single mom, and now gives away as much of her money as she can to fund gender equity. She’s the New York Times bestselling author of Fair Play, the founder of the movement and the Fair Play Policy Institute, and she’s raising three kids in LA.

    In this episode, she sits down with me to break down how she actually affords the life, and the movement.

    Eve and I walk through how she went from a $42,000 nonprofit salary to the income streams behind her life now: speaking, advances for two books, the Fair Play card deck, and years as an advisor to families who look like the cast of Succession.

    Plus, she shares her three steps to wealth, including the 2% mortgage she locked in for her mom on a home that has since gained almost $500,000 in value.

    Eve reveals the math behind “my salary only covers childcare” and why she calls it the worst calculation women make, why she and her husband Seth share everything, the year of service her kids have to do if they want help with college, and what she’s working toward affording next.

    Download Ashley’s free “Get Paid What You’re Worth” negotiation guide (https://www.thefiscalfemme.com/get-paid).

    Get Eve’s book, Fair Play (https://www.fairplaylife.com/the-book).

    Find free resources from the Fair Play Policy Institute (https://fairplaypolicy.org) and follow along on Instagram @fairplaylife (https://www.instagram.com/fairplaylife) and @everodsky (https://www.instagram.com/everodsky).

    Check out Ashley’s Money Club (https://www.thefiscalfemme.com/money-club) to join a community of women unabashedly going after their money goals.

    Take this quiz to get a personalized Wealth Building Blueprint (https://bit.ly/4v94g2C)

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    55 mins
  • #24: She Paid $95 for a Trunk. She Was Offered $30K
    Oct 28 2026

    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 Chairish and hangs in the green room at Jimmy Kimmel, and she has close to a million followers between Instagram and Facebook. In this episode she sits down with me to break down how she actually affords it.

    Virginia and I walk through every single one of those income streams and what they add up to, the $95 trunk she’s since been offered $30,000 for, the $100 brass chairs from a Salvation Army that ended up with a tech CEO in San Francisco, and how a book advance actually works.

    Plus, she shares exactly where to go to find the good stuff, what to do when you’re standing in a thrift store with no idea what you’re looking at, and how to tell whether something is worth anything while you’re holding it.

    Virginia reveals the spending philosophy she knows her financial advisor would not approve of, the portfolio she built herself that got called the riskiest one he had ever seen and what she gets gifted in a year.

    Download Ashley’s free Investing Guide (https://www.thefiscalfemme.com/investing-guide) for everything you need to start investing confidently and competently, including how to decide what to keep in cash first.

    Get Virginia’s book, Big Thrift Energy (https://www.penguinrandomhouse.com/books/696602/big-thrift-energy-by-virginia-chamlee/) and follow her on Instagram (https://www.instagram.com/vchamlee/) and TikTok at Virginia Chamlee.

    Subscribe to Virginia’s Substack (https://www.bigthriftenergy.com/).

    Check out Ashley’s Money Club (https://www.thefiscalfemme.com/money-club) to join a community of women unabashedly going after their money goals.

    Take this quiz to get a personalized Wealth Building Blueprint (https://bit.ly/4v94g2C)

    Show More Show Less
    1 hr and 2 mins
  • He Googled "How to Be a Great Husband." Then She Got a Global Promotion.
    Oct 21 2026

    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 of it, the rule they never broke on housing, how they paid for three kids without taking on debt, and the one sentence he asked his wife to tell her boss that turned into a global promotion two weeks later.

    Plus, he shares why he irons his wife's clothes before he puts them away, and the three books he tells every man to read.

    Brian reveals the bleeding ulcer and the Christmases he spent too sick to leave the house, the junk car his father made him drive and the reason behind it, what the research says about couples who combine all their finances, and how he thinks about protecting himself financially now that he is not the one earning.

    Download Ashley's 'Become Your Own CFO' bundle (https://www.thefiscalfemme.com/cfo-bundle) for everything you need to manage the money you make in a strategic and financially savvy way.

    Find Brian at modernhusbands.com and subscribe to his Saturday morning newsletter.

    The three books Brian recommends to every man: The Ambition Penalty by Stefanie O'Connell Rodriguez (https://www.hachettebookgroup.com/titles/stefanie-oconnell/the-ambition-penalty/9781541705210/), Equal Partners by Dr. Kate Mangino [LINK TO ADD], and Fair Play by Eve Rodsky [LINK TO ADD].

    Listen to Stefanie O'Connell Rodriguez's episode of How Do You Afford This? [EPISODE LINK TO ADD].

    Check out Ashley's Money Club (https://www.thefiscalfemme.com/money-club) to join a community of women unabashedly going after their money goals.

    Take this quiz to get a personalized Wealth Building Blueprint (https://bit.ly/4v94g2C)

    Show More Show Less
    51 mins
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