EP. 06 | Libby Leffler on Protecting Your Future Self: A New Playbook for Marriage and Money

In this episode, Alexis Contos sits down with Libby Leffler, tech executive turned founder of First, who is dismantling the stigma around prenups and reframing them as the ultimate act of partnership design. After spending nearly two decades building generation-defining companies like Google, Facebook, and SoFi, Libby noticed a glaring gap in how we handle our most significant personal "merger", marriage. She realized that while we plan meticulously for our careers and companies, we often leave our relationships to chance. She founded First to change that, shifting the narrative from a "breaking point" to "a "joining point." From debunking the Sex and the City era myths about prenups to defining "modern money" (it’s not just cash, it’s your IP, your side hustle, and yes, even your pets), Libby is normalizing the hard conversations that actually make couples stronger. She’s helping women protect their "future selves" amidst the Great Wealth Transfer, ensuring they enter partnerships with clarity rather than crossed fingers. In this conversation, Libby opens up about the reality of leaving a high-powered corporate career to build a startup while raising young children. She discusses why "work-life balance" is a lie we need to stop believing, how she uses "focus" as her superpower to navigate different seasons of life, and why she believes your failures will always teach you more than your successes. Whether you’re walking down the aisle, negotiating a raise, or just trying to figure out how to integrate your ambition with your life, this episode offers a new operating agreement for it all. The Breadwinners Website  
First Official Website  First's Instagram Libby’s Instagram Breadwinner's Instagram Business Insider Article Use code THEBREADWINNERS at checkout for $100 off First lawyer reviewed prenup package Promo code available 1/5/2026 through 3/1/2026 11:59p PT; all coupon codes must be used a checkout at time of purchase (no retroactive discounts), terms and conditions apply Learn more about your ad choices. Visit megaphone.fm/adchoices