『How Do You Afford This?』のカバーアート

How Do You Afford This?

How Do You Afford This?

著者: 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.

© 2026 How Do You Afford This?
個人的成功 自己啓発
エピソード
  • #14: What the Mother of AI Is Teaching Her Kids About Money
    2026/08/19

    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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    55 分
  • #13: She Built a Seven-Figure Business. Now She's Rebuilding From $150K in Debt
    2026/08/12

    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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    54 分
  • #12: She Left a Six-Figure Salary. Her First Client Paid More Than the Job Did
    2026/08/05

    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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    1 時間
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