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.

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)

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)

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)

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)

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)

Rachel Lipson takes 12 to 15 trips a year with her family of four, her kids have visited 25 countries and they haven’t even finished elementary school, and she lives in one of the most expensive zip codes in the country. She’s the founder of The Point, a best-selling Substack and consulting business that teaches families how to travel using credit card points and the founder of Blue Balloon Songwriting for Small People, a 17-year-old music school for kids that now runs mostly without her. In this episode, she sits down with me to break down how she actually affords the lifestyle.

Rachel and I walk through how she redeemed over $143,000 in points last year, the specifics of her recent three-week family trip across Milan, Athens, and Malta, and the home-swapping strategy that has gotten her family into beautiful homes around the world for free. Plus, she shares her top three points strategies and the simple first step for anyone who feels overwhelmed by the points game.

Rachel reveals the times even she doesn't get the points game perfectly right, the multiple income streams that fund her family's life in Brooklyn, and the surprising childhood backstory that drives her family's travel obsession.

Get Ashley’s travel budget template (https://www.thefiscalfemme.com/travel-budget) where you can estimate trip costs, compare options and plan in advance so that all you have left to do is enjoy your trip, financially stress free. 

Subscribe to Rachel’s substack (thepoint.substack.com). Get a Wallet Edit (https://thepointedit.com/wallet-edit-phone-session) for tips on how to leverage spending to earn points for travel!

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)

Ashley Torres spends three months per year in a new country with her family, takes five other trips a year, salsas with her friends one to three times a week, and runs multiple businesses. She's been a full-time content creator for over 15 years, writes about her family’s travels on Substack, is the co-founder of LA Girl Dinner Club, and wants us all to live life to the fullest. In this episode, she breaks down how she actually affords the lifestyle.

Ashley walks through exactly what her recent three-month stay in Uruguay actually cost, the surprising income streams that offset the costs, and the trade-offs she makes that make it all work. Plus, she shares her salsa-at-10pm hack that fuels her energy and the worldview that drives her whole approach.

Ashley also reveals how she and her husband Andy navigated combining finances after years of keeping them separate, what she's teaching her daughter about money and gratitude, and where her clothes-and-decor budget actually goes.

Get Ashley’s travel budget template where you can estimate trip costs, compare options and plan in advance so that all you have left to do is enjoy your trip, financially stress free. 

Connect with Ashley on Instagram at @everydaypursuits and her family travel Substack.

Check out Ashley’s Money Club to join a community of women unabashedly going after their money goals. 

Take this quiz to get a personalized Wealth Building Blueprint.

Nicole Giordano spends three months a year living in Europe, owns her home, and works thirty hours a week in a career she loves. She's the founder of Midlife Creative Studio and a long-time online entrepreneur who has spent the last decade designing a life around what actually matters to her, thoughtfully and strategically. In this episode, she sits down with me to break down how she actually affords the lifestyle.

Nicole and I walk through exactly what she spent on her recent three-month stay in Spain, how she and her partner built a life where either of them could afford it on their own, and her best travel hacks for stretching the budget. Plus, she shares the mindset shift that turned three months in Europe from a vacation fantasy into an annual ritual.

Nicole reveals her "enough" philosophy that lets her spend $12,000 on a kitchen renovation instead of $50,000, the mantra she uses to stay the course even when she’s tempted, and the one question she wants us all to ask ourselves to craft and afford our dream lives.

Get Ashley’s travel budget template where you can estimate trip costs, compare options and plan in advance so that all you have left to do is enjoy your trip, financially stress free. 

Learn more about The Studio, Nicole’s community for midlifers who want more creative practice in their lives.

Check out Ashley’s Money Club to join a community of women unabashedly going after their money goals. 

Take this quiz to get a personalized Wealth Building Blueprint.

Jen Glantz has built an empire around love stories without actually liking weddings. She’s the founder of Bridesmaid for Hire, host of the 1-800-Bridesmaid podcast, and author of multiple books including her newest, Finally the Bride. In this episode, she breaks down the numbers behind her own wedding, her clients' weddings, running multiple businesses and raising a daughter in NYC. 

Jen and I walk through the $35,000 wedding she almost had, the one she pulled off for under $2,000, how her business evolved from a single $500 service into multiple income streams, and why launching over 100 AI tools changed everything after she became a mom. Plus, she shares the brutally honest scripts she gives bridesmaids who can't afford to say yes, and what to say when a friendship gets expensive.

Jen reveals the real cost of raising a child in New York City, how she and her husband combined finances after their daughter was born, and what she's working toward affording next.

Use Ashley’s Wedding Budget to see the true cost of your wedding, compare venues and scenarios, and plan financially.

Get Jen’s new book, Finally the Bride and sign up for her Monday Pick Me Up newsletter!

Check out Ashley’s Money Club to join a community of women unabashedly going after their money goals. 

Take this quiz to get a personalized Wealth Building Blueprint.