How Do You Afford This?

Ashley Feinstein Gerstley
  • 5.0 (41)
  • 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. 6d ago ·  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

  2. 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

  3. 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

  4. 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

  5. Sep 2 ·  Video

    #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 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 Unfinished Business podcast, and is raising three kids in Lisbon.  In this episode, she sits down with me to break down how she actually affords the lifestyle. Alex and I walk through how she funded a physical product business without raising a dollar, the manufacturer relationship that let her front inventory before she had sold any of it, and how she and Johnny knew the company could finally afford to pay them. Plus, what her podcast costs to produce every month and why this fall is the first time it might pay for itself, why she takes out insurance on any purchase order above $250,000, and what her two previous exits actually did for her finances. Alex reveals the AI infrastructure that’s part of her minimum viable company framework, including her chief of staff Freddie, who is not a person, and an entirely new business she announces on the show for the first time.  She gets into the Lisbon schools that cost a quarter of what New York private schools do, the thing about moving to Europe that genuinely surprised her, what her parties actually cost, and what she's working toward affording next. 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. Follow Alex on LinkedIn (https://www.linkedin.com/in/alex-schinasi-16b6abb/) and Instagram (https://www.instagram.com/alexschinasi/). Listen to the Unfinished Business podcast (https://www.youtube.com/@UnfinishedBizPodcast). Shop Hulken (https://hulken.com). Learn more about Northstone (https://northstone-ai.com), the AI infrastructure company Alex announces on this episode. 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)

    #16: She's Building a $100M Brand From Lisbon With 3 Kids

  6. Aug 26 ·  Video

    #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 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 corporate job to a content business that replaced her salary and then doubled it. In this episode, she sits down with me to break down how she actually affords it. Paige and I walk through the $60,000 to $70,000 a year her family spends on childcare, her household’s income trajectory, the freelance sales job she worked at night and on weekends to cover daycare, and why childcare costs are so hard for anyone to find in the first place. Paige reveals the unpaid labor snowball that started after kids, the spreadsheet she and her husband used to divide the invisible work, and the time equity assessment that finally explained why she was so burnt out. She gets into the motherhood penalty and the fatherhood bonus, the one thing about her finances that people would never guess, 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). Follow Paige at @shesapaigeturner on Instagram(https://www.instagram.com/sheisapaigeturner/), TikTok (https://www.tiktok.com/@sheisapaigeturner), and YouTube (https://www.youtube.com/@sheisapaigeturner). Subscribe to her Substack (https://substack.com/@sheisapaigeturner).  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)

    #15: Her $70K a Year Childcare Bill Went Viral

  7. Aug 19 ·  Video

    #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 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 that runs it all: the $180,000 a year her family lives on, and why everything the businesses earn above that goes toward renovations, vacations, and investments. She shares how she and her husband run their budget like a P&L, the quarterly check-ins that keep it honest, and the small swaps she made to protect the number. We talk about the egg business her sons run at $8 a dozen, and what happened when they learned that feed and electricity come out of their revenue. Brit reveals exactly how AI puts money back in her pocket every month, from the QuickBooks subscription she replaced by building her own version on Claude to the hours of follow-up work she no longer does by hand. She gives her best advice for three types of people: someone intimidated by AI, someone trying to get promoted, and someone who wants AI to be their first employee.  Plus the family history that shaped all of it, what ten days in Hawaii actually took, and the early retirement she is planning in the next five years. Join The Mother of AI Academy at themotherofai.com and use the code FISCALFEMME for 10% off.  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. Learn more about The Mom Economy, Brit's 501c3 supporting female founders with benefits and parental leave, at themomeconomy.com. Follow Brit on Instagram at @themotherofai. 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)

    #14: What the Mother of AI Is Teaching Her Kids About Money

  8. Aug 12 ·  Video

    #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 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 this show. Claire and I walk through her whole earning journey, from trading salary for equity at a startup that later sold for $12.9 million, to the seven-figure years of brand sponsorships and thousand-person conferences, to the $300K book advance.  Then the part almost nobody says out loud: how the pandemic broke her business model, why a family medical crisis drained their finances, and how they ended up $150K in debt Claire reveals what it actually feels like to swipe an EBT card, the half-price apartment her grandfather wrote into a building's deed, and why the shame around food hits differently than every other benefit.  She gets into how childcare math forced her and her wife to renegotiate everything including their sleep, her lightning round of negotiation advice, and why she thinks being in the middle of healing makes her a better coach. Download Ashley's free "Get Paid What You're Worth" negotiation guide (https://www.thefiscalfemme.com/get-paid). Learn more about Claire's work and coaching at ladiesgetpaid.com, subscribe to her Substack, and follow her on Instagram at @clairegetspaid and @ladiesgetpaid. 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)

    #13: She Built a Seven-Figure Business. Now She's Rebuilding From $150K in Debt
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5
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41 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
    21
  • Rating
    Explicit
  • Copyright
    © 2026 How Do You Afford This?
  • Show Website
    How Do You Afford This?

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