How Do You Afford This?

Ashley Feinstein Gerstley
  • 5.0 (44)
  • Self-Improvement

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. 

  1. 3d ago ·  Video

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

    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)

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

  2. Oct 21 ·  Video

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

    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. Get Ashley’s free budgeting system (https://www.thefiscalfemme.com/budgeting-spreadsheet) to put together your spending plan for the next 24 months.  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 (https://www.katemangino.com/equal-partners)Fair Play by Eve Rodsky (https://www.fairplaylife.com/the-book)Listen to Stefanie O'Connell Rodriguez's episode of How Do You Afford This? (https://podcasts.apple.com/us/podcast/06-the-%24100k-she-saved-to-fund-her-book-and-first/id1896768344?i=1000774012924)  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)

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

  3. Oct 14 ·  Video

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

    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 life. Jess and I walk through the real economics of making physical things: what a levitating table sells for versus what it costs to build, the $1.6 million she raised for Rock Paper Robot and how quickly it was gone, the licensing deal she signed with someone she trusted, and the $200 to $400 an hour she charges for the consulting work that pays her bills now.  Plus, she shares what a Netflix host really gets paid, the wardrobe budget she was handed and how many looks it had to cover, and what she spent out of pocket just to attend the Emmys. 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. See Jess's work at rockpaperrobot.com and follow her on Instagram (https://www.instagram.com/rockpaperrobot/). Watch Hack My Home on Netflix (https://www.netflix.com/title/81319212). 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)

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

  4. Oct 7 ·  Video

    #21: How She Got Matt Damon for $800

    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 sits down with me to break down how she actually affords the lifestyle, starting with the most honest answer you could ask for. Jill and I walk through how an independent film actually gets financed, why she put some of her own money in, what it cost to cast Matt Damon and Gwyneth Paltrow, and the location that would have run $100,000 that she got for $12,000.  Plus, she shares why asking for money is the part of the job she hates most, and what two paid posts years ago taught her about what she is willing to sell. Jill reveals what she thinks Dzanielle would need to earn to pull off the lifestyle, why money is still harder to talk about than sex, the trade her family makes to afford the way they travel, and what she and her husband did to keep three kids grounded in a neighborhood with so much comparison.  Take this quiz to get a personalized Wealth Building Blueprint (https://bit.ly/4v94g2C) Watch Influenced, streaming now on Apple (https://tv.apple.com/us/movie/influenced/umc.cmc.3yoyvkwzuzfs3o1q17wx2qjcn) and Amazon (https://www.amazon.com/gp/video/detail/B0H49DY1H7). Follow Jill on Instagram (https://www.instagram.com/jillkargman/). Read The Opposite of Spoiled by Ron Lieber (https://ronlieber.com/books/the-opposite-of-spoiled/), the book on raising kids and money that Jill says every parent should read. Learn more about the American LGBT Museum (https://americanlgbtqmuseum.org/), opening in 2028 on 77th Street and Central Park West, where Jill serves on the board. Support the River Fund (https://www.river.fund/) in Queens, the food pantry and family program Jill's family has volunteered with for years. Check out Ashley's Money Club (https://www.thefiscalfemme.com/money-club) to join a community of women unabashedly going after their money goals.

    #21: How She Got Matt Damon for $800

  5. Sep 30 ·  Video

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

    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 with it, the $75,000 they spent moving walls, the $230,000 they spent furnishing every room, and what the two most expensive pieces in the apartment actually cost.  Plus, she shares the four-word negotiation phrase she uses on everything from party vendors to invoices, and exactly what it has saved her. Laura reveals how they actually paid for that apartment, what a nanny, camp, and after-school activities cost for three kids in Manhattan, the single conversation with her employer that produced the biggest income jump of her career, and why she still has no idea what she is inheriting. Plus, what she is working toward affording next. Download Ashley's free "Get Paid What You're Worth" negotiation guide (https://www.thefiscalfemme.com/get-paid). 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) Get Tanja Hester's book, Work Optional (https://tanjahester.com/work-optional/).

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

  6. Sep 23 ·  Video

    #19: She Opened a Wine Bar for $100K. Then She Bought the Building

    Hillary Zio spent twenty years working in wine for other people. Now she owns Isola, a twenty-four-seat wine bar in Kinderhook, New York with a list devoted entirely to the islands and coasts of Europe, and she owns the historic building it sits in.  She's a Certified Sommelier, a wine consultant, a wine club founder, and the author of two books including her new memoir, Still Working in Wine: Twenty Years Later. She's also raising her seven-year-old daughter in the Hudson Valley.  In this episode, she sits down with me to break down how she actually affords the lifestyle. Hillary and I walk through the $100,000 it took to open Isola, why year one was not profitable, and the half dozen income streams that fund the whole thing.  She shares what it really costs to become a Certified Sommelier, from the $5,000 in coursework to the $15,000 to $20,000 in wine she bought just to train her palate. Plus, her rules for finding a bottle you'll love for $30. Hillary reveals the unexpected way she went from renting her restaurant space to owning the entire commercial building, what her in-ground pool cost to put in and what she pays every single summer to keep it, the $20,000 a year private school she no longer pays for, and the money belief that let her stop spending to impress other people.  Get Ashley's Budgeting System (https://www.thefiscalfemme.com/budgeting-spreadsheet) to get clear on what's actually worth it to you, cut what isn't, and free up money for the things you really want. Get Hillary's new memoir, Still Working in Wine: Twenty Years Later (https://www.amazon.com/dp/B0H2SPSJYN). Visit Isola Wine & Tapas in Kinderhook, NY (https://isolawinebar.com/), and follow Hillary on Instagram at (https://www.instagram.com/hillaryzio/), where you'll find her wine club, her online wine course, and everything else she's building. Check out Ashley's Money Club (https://www.thefiscalfemme.com/money-club) to join a community of women unabashedly going after their money goals.

    #19: She Opened a Wine Bar for $100K. Then She Bought the Building

  7. Sep 16 ·  Video

    #18: Her 11-Year Relationship Ended. She Had the Money to Heal

    Meghan Lim was laid off three times before she bet on herself. She's a personal finance creator who took her net worth from a negative number to six figures in three years, all while keeping her spending between two and three thousand dollars a month. In this episode, she sits down with me to break down how she actually affords the lifestyle. Meghan reveals how she used her emergency savings to take care of herself when her eleven-year relationship ended this summer, why she and her fiancé never combined a single account in all that time, and what she wants every woman to have before she needs it.  Meghan and I walk through the $108,000 she earned in her first full year of content creation, the corporate salary she walked away from, and the nine months between jobs when pet sitting and a matcha shop paid the bills. Plus, she shares exactly what her life costs now, from the $1,350 in rent to the groceries and the gym, the four income streams that fund it, and the Zillow trick that got her an apartment ten other people applied for. She also shares the one thing about her finances people would never guess: the hundred dollars a week she puts into Bitcoin. Download Ashley's investing guide (https://www.thefiscalfemme.com/investing-guide) so the money you're setting aside is actually working for you. Follow Meghan on Instagram (https://www.instagram.com/meghanmakesmoney/) and TikTok (https://www.tiktok.com/@meghanmakesmoney). Join Meghan's Skool community (skool.com/moneymakerscircle) for weekly calls and her digital products. 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)

    #18: Her 11-Year Relationship Ended. She Had the Money to Heal

  8. Sep 9 ·  Video

    #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 she rents an apartment in the Financial District she negotiated below market. I have known her for over a decade and had no idea she was a professional ballerina first.  In this episode, she sits down with me to break down how she actually affords the lifestyle. Priya and I walk through the $33K starting salary she negotiated at Merrill Lynch, the almost ten years it took before she was technically a six figure earner in her own business, and the flat fee pricing she tried first and why it didn't work. Plus, the $3,500 rent she kept flat for three years in Manhattan without a rent stabilized lease, why she sold her car, and how she decides the company can afford a new hire. Priya reveals the magic number she uses instead of a budget, the sub savings accounts she runs for everything from travel to doorman tips, and the framework she gives clients whose income swings month to month. She gets into growing up in a high earning household that still felt like there was never enough, why she was offended when someone told her to sell the company for $10 million, and what she is working toward affording next. Download Ashley's investing guide (https://www.thefiscalfemme.com/investing-guide) so the money you're setting aside actually works for you.  Learn more about Stash Wealth (https://stashwealth.com). Follow Priya on Instagram (https://www.instagram.com/itspriyamalani/) where you get her free guide, The Only Money Move You Need to Make in Your Thirties. 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)

    #17: It Took Almost 10 Years Before She Earned Six Figures
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5
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44 Ratings

About

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. 

Information

  • Creator
    Ashley Feinstein Gerstley
  • Years Active
    2026
  • Episodes
    25
  • Rating
    Explicit
  • Copyright
    © 2026 How Do You Afford This?
  • Show Website
    How Do You Afford This?

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