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.

How Do You Afford This? is a education podcast hosted by Ashley Feinstein Gerstley, with 14 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Ashley Feinstein Gerstley hosts How Do You Afford This?, a education show with 14 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #14

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

  Aug 19, 202655 minS1

  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 )

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  Episode #13

  #13: She Built a Seven-Figure Business. Now She's Rebuilding From $150K in Debt

  Aug 12, 202654 minS1

  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 )

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  Episode #12

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

  Aug 5, 20261 hourS1

  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 )

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  Episode #11

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

  Jul 29, 202645 minS1

  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 (https://www.thefiscalfemme.com/save-1000-this-month). Take this quiz to get a personalized Wealth Building Blueprint ( https://bit.ly/4v94g2C ). Check out Ashley's Money Club ( https://www.thefiscalfemme.com/money-club ) to join a community of women unabashedly going after their money goals.

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  Episode #10

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

  Jul 22, 20261h 3mS1

  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 )

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