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How Do You Afford This?

Ashley Feinstein Gerstley

Booking Overview

This is an interview-led personal finance and lifestyle show featuring external guests who openly break down the real costs of their households, careers, businesses, and financial decisions. PR agencies could credibly pitch founders, authors, career and financial experts, and creators with compelling, transparent money stories; booking difficulty is medium because guests typically need both professional credibility and a distinctive personal financial journey.

Metrics

Episodes: 22

Frequency: Weekly

Rating: 5.0/5.0

Estimated listeners: 100 - 1,000

Gender skew: Female

Listener location: USA

Contact Information

Publicly listed emails

ashley@thefiscalfemme.com

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Host

Ashley Feinstein Gerstley - Certified financial planner, founder of The Fiscal Femme, and award-winning author focused on helping people build wealth and make strategic decisions with their money.

Booking Intelligence

Booking Requirements

medium
Typical Credentials:  
Founders, entrepreneurs, authors, career or financial experts, senior professionals, and creators with an established business, audience, or professional track record and a substantive personal money story.
Required Achievements:  
Built or rebuilt a business, Authored a book or developed recognized expertise, Built an audience, community, or content platform, Achieved notable career or business growth

Recent Guest Discussions

Paige Connell - Her Family’s $60,000–$70,000 Annual Childcare Costs, Household Income, Unpaid Labor, The Motherhood Penalty, And Building A Business That Replaced And Exceeded Her Corporate Salary.

Brittany Valdes - Managing A $180,000 Household Lifestyle, Entrepreneurship, Using Artificial Intelligence To Reduce Business Costs And Administrative Work, Teaching Children About Money, And Planning For Early Retirement.

Claire Wasserman - Business Growth And Decline, Startup Equity, Book Income, Family Financial Hardship, Debt, Food Assistance, Childcare, And Renegotiating Finances Within A Family.

Erika Velazquez Alpern - Leaving A Six-figure Salary, Rebuilding A Business, Client Revenue, Freelance Financial Volatility, Childcare Costs, And Marketing Strategies At Different Budget Levels.

Recent Topics

Personal Finance, Wealth Building, Entrepreneurship, Careers, Parenting

Episodes

Here's the recent few episodes on
How Do You Afford This?
:

#21: How She Got Matt Damon for $800

October 07, 2026

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 s...

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

September 30, 2026

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 com...

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

September 23, 2026

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...

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Publicly listed emails

ashley@thefiscalfemme.com

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