How Do You Afford This?

Ashley Feinstein Gerstley
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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. 4 days ago ·  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

  2. 5 Aug ·  Video

    #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, 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 CMO, the founder of Tactile, and a mom raising two kids and a pup in Brooklyn. In this episode, she sits down with me to break down how she actually affords the lifestyle. Erika and I walk through the real math of working for yourself: the six-figure salary she left, the anchor client that paid her more per month than her full-time job did, the $170,000 her business brought in its first year back, and how it feels when a good month approaches $30,000 and a slow one barely clears $5,000.  Erika reveals what raising two kids in Brooklyn actually costs, starting with $3,500 a month for a private twos program and camps that run $600 to $800 a week. She gets into the marketing money she has watched businesses light on fire, exactly what she would do with a $0 budget, a $1,000 budget, and a $10,000 budget, the dream job she turned down because the math didn’t make sense, and the thing about her finances that would surprise you most.  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 Erika's work at wearetactile.com, and come to one of her events. Follow her on Instagram at @erikaalpern. 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)

    #12: She Left a Six-Figure Salary. Her First Client Paid More Than the Job Did

  3. 29 Jul ·  Video

    #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 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 feel rich, to the night out that ended with her trying to pay with a pet store card. We get into the money experiments I've run on her over the years: the credit cards in the freezer, and the 401(k) contribution I set to 15% that she didn't fully notice until years later. Today there are six figures in that retirement account. Ariel reveals what it's actually like having a money expert as a sister (annoying, then useful), a brand-new secret she'd been keeping even from me, and she gets her very first money homework assignment on the show. This is the first of many. We've got her home purchase, her tiny wedding, and the great pet insurance debate all coming in future episodes. Download Ashley's free guide to save $1,000 in one month  Take this quiz to get a personalized Wealth Building Blueprint. Check out Ashley's Money Club to join a community of women unabashedly going after their money goals.

    #11: She Called Me to Say the Bank Was Broken. Now She Has Six Figures Saved

  4. 22 Jul ·  Video

    #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 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 with her spouse. Heather and I walk through her income journey, from her first $81,000 salary in New York City while carrying $217,000 in student loan debt, to the $200,000-plus compensation and roughly $50,000 in healthcare benefits she walked away from, to the 18-24 months of living expenses they banked before she made the leap. She shares their household income range today, what childcare cost them in the city, and why quarterly money dates are the system that holds it all together. Heather reveals the COVID power dynamic that left her resenting her husband and inspired the book, how financial support from parents is an "existential safety net" and why the rest of us get so angry about it. She also gives her top tips for couples at three different life stages and shares what she's working toward affording next. Download Ashley's free guide on how to save $1,000 this month (https://www.thefiscalfemme.com/save-1000-this-month). Order Heather and Doug’s book, Money Together (https://domoneytogether.com/).  Subscribe to their free Joint Account newsletter (https://www.readthejointaccount.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)

    #10: She Resented Her Husband. Then She Left a $200K Salary to Join Their Family Firm

  5. 15 Jul ·  Video

    #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 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 to break down how she actually affords the lifestyle. Viviana and I walk through her income climb, from a $57,000 teaching salary to earning $185,000 in tech, and the $130,000 in revenue her business has already brought in this year. She breaks down her actual payday routine with Xavi down to the dollar, shares exactly what makes up her $510K net worth, and takes us inside their World Cup trip to Mexico they spent three years saving for. Viviana reveals what it really costs to be the first, from helping her parents pay off $80,000 in debt to taping her dad's credit cards, how she and Xavi turned a college friendship into a wealth-building partnership with two weddings and a People magazine feature along the way, 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 Viviana on Instagram at @overgenpoverty (https://www.instagram.com/overgenpoverty).  Listen to Tech Quiero Más wherever you get your podcasts (https://podcasts.apple.com/us/podcast/techquiero-m%C3%A1s/id1877341355). 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)

    #09: From Poverty to a $510K Net Worth: How This First-Gen Eldest Daughter Made It Happen

  6. 8 Jul ·  Video

    #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 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 guarantee to the cut of the door, and the bronze handcuffs of running this many businesses at once. Plus the safety net he says so many have yet nobody wants to admit to, from bar mitzvah savings to the parents' phone plan he is never getting off of. As a go-to for dating advice, Jared also gets into where money and relationships collide: why "I'm not ready" is usually a money decision, and the rent conversation he is having right now as his girlfriend moves in. He reveals what people would never guess about how he thinks about money, why the craft matters more than the check, and what he is working toward affording next. Download Ashley's '7-Day Jumpstart’ (https://www.thefiscalfemme.com/7day-jumpstart) for a  step you can take each day for a week to completely transform your financial well-being.  Get Jared's book, Walking Red Flag (https://www.simonandschuster.com/books/Walking-Red-Flag/). Grab tickets to Jared's shows (https://punchup.live/jaredfreid) and follow him on Instagram @jaredfreid. 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)

    #08: The Finances Behind a Top 10 Netflix Comedy Special

  7. 1 Jul ·  Video

    #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 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 through CityRow with a financial lens: the $0 marketing budget that made it explode, the $12 million she raised in six weeks during COVID, the more than $20 million she raised in total, and the exit that came out to a zero for her investors and for her. Plus, what two years on a GLP-1 has actually cost her, from the $1,000 consults to the surprising ways she’s spending less.  Helaine reveals the scrappy strategies that fund a life in two cities, what it felt like to be on the Today Show and unable to pay rent, how she handles the awkward money conversations most of us avoid, 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. Subscribe to Helaine's weekly newsletter (https://www.helaineknapp.com/what-im-building) and her Substack (https://helainemknapp.substack.com/) Get Helaine's book, Making Waves (https://www.helaineknapp.com/making-waves).  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)

    #07: This Founder Raised $20M. The Exit Was a Zero

  8. 24 Jun ·  Video

    #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 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 for her daughter. We walk through her whole money trajectory, from $450 a week on a Broadway tour to a business pulling in around $300,000 in revenue. Then the part most people never say out loud: how she set aside more than $100,000 as a runway, watched her revenue fall almost 90% last year, and has been spending down that cushion ever since. Plus the data behind the book, including the half-million-dollar lifetime cost of the motherhood penalty. Stefanie also gets honest about the power dynamics inside households and her own marriage, what she hopes her daughter learns by watching how responsibility gets shared at home, and her reframe of money as seasons instead of a straight line. And of course, what she is working to afford next. Download Ashley’s free “Get Paid What You’re Worth” negotiation guide (https://www.thefiscalfemme.com/get-paid).  Get Stefanie's book, The Ambition Penalty (https://www.hachettebookgroup.com/titles/stefanie-oconnell/the-ambition-penalty/9781541705210/). Subscribe to Stefanie's newsletter, Too Ambitious, and follow her on Instagram @stefanieoconnell. 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)

    #06: The $100K She Saved To Fund Her Book and First Years of Motherhood
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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
    14
  • Rating
    Explicit
  • Copyright
    © 2026 How Do You Afford This?
  • Show Website
    How Do You Afford This?

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