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)