Get Fluent in the F Word.
Libby Leffler on finances, protecting your assets, the 'latte factor' scam, and the money habits she wishes she'd built sooner.
My parents never had a prenup, neither did my grandparents. Nobody in my family ever talked about it. The only reference point I had going into my marriage was Charlotte York negotiating with Bunny MacDougal in a 2005 episode of Sex and the City. “I’m worth a million dollars” - that was my association.
Cut to twenty years later, and nearly half of millennials getting married now get a prenup. About half of those conversations are initiated by women.
Libby Leffler is the founder and CEO of First, a platform making prenuptial agreements accessible to modern couples, and she sat down with me to talk about what’s actually changing.
But what I really want to talk about is the conversation we had about careers and motherhood and the pressure we put on ourselves that, as Libby points out, came from nobody but us.
Before we get there, one thing she said that shocked me: everyone has a prenup. It’s either the one you made, or the one the government made for you. The default laws of your state have already determined how your finances will be treated in a marriage. Most people just never asked whether they agreed with that.
And for the women in the Breadwinners community who skipped this conversation because they didn’t feel like they had enough to protect, Libby’s reframe is worth listening to: a prenup isn’t about the you of today. It’s about the future you. Your IP, your equity, your 401k, the apartment you bought before you met anyone, the social handles you’re building an audience on. Some of those assets don’t exist yet. That’s why its so important to think about the future you. Women are set to inherit the majority of $110 trillion in the great wealth transfer over the next decade. That money is coming. The question is whether we’ll be positioned to receive it fully.
Below are the highlights from our conversation…
Money is harder to talk about than sex.
Libby made this point and it’s incredibly accurate. We’ve had decades of cultural evolution around talking openly about sex. Money is still treated taboo. Because for most people it’s tied to identity in a way sex simply isn’t. It’s your family’s history. The stories you were told about who’s good with money and who isn’t. Your own failures and the shame attached to them.
That’s why the prenup conversation feels so charged. It’s not really about the assets. It’s about whether you believe you’re worth advocating for. Whether asking for transparency makes you strategic or suspicious. Whether you can sit across from someone you love and talk about what happens if this stops working, without treating that as a prediction.
My husband and I got married in the Greek Orthodox Church. Before the priest would marry us, we went through a counseling process. Questionnaires. Then a joint session to compare answers. Kids. Religion. Finances. We agreed on most things. We knew where we didn’t. I didn’t think of that process as a prenup at the time. Libby told me it was the inspiration for building First. Based on a structured invitation to talk about the hard stuff before the hard stuff arrives.
Get fluent in the F word.
Her biggest financial regret: not getting in the weeds on her own finances sooner. Not knowing what her portfolio looked like. Not tracking where money was going and what it was doing. She’s very hands on with it now. But she wishes she’d started earlier, when the stakes felt lower and the habits would have been easier to build.
Also, for the record: the ‘latte factor’ (small cost vs big impact) is a scam. Nobody has ever built generational wealth by skipping the matcha. Know where your money is going, know what your goals are, figure out if you can get there and then reconfigure if not. But please, for the love of God, drink the coffee.
The pressure came from you. It always did.
Libby described her twenties as defined almost entirely by impatience. No patience for herself, for her timeline, for the distance between where she was and where she thought she should already be. And she realized she projected that pressure onto other people - managers, peers, circumstances - when in reality it was all her own doing.
Nobody was telling her to move faster. She was telling herself.
This is the thing nobody prepares you for about ambition: it doesn’t come with an off switch. The same drive that gets you somewhere is the thing that makes it impossible to enjoy being there. At some point the work has to stop being the whole identity, and for most of us that shift takes longer than it should and costs more than we expected.
Libby had to remind herself: if she’s going to do this at the pace and execution she wants, it has to be fun. It has to be fulfilling. Without that, it all falls apart.
“This is the thing nobody prepares you for about ambition: it doesn’t come with an off switch. The same drive that gets you somewhere is the thing that makes it impossible to enjoy being there.”
Read the room before you make your ask.
She spent years in tech in San Francisco before building First. Chief of Staff to Sheryl Sandberg in the early days of Facebook. One of the things she carried out of that chapter: know how to manage up. Know your audience. Understand timing.
She used to walk into meetings loaded with data. The best analysis, the freshest numbers, the most airtight case. And she could feel the room go flat. Because she was leading with data instead of a story. Trying to win a debate instead of paint a picture.
She learned to lead with the story first. Use data to support it, not open with it.
This applies to asking for raises, for promotions, for anything that requires someone else to say yes. The ask itself is only part of it. The quarter just ended short. Your boss got difficult news. The company missed its number. Those are not your moments, even if your case is airtight. As they say, timing is everything.
The best thing I took from corporate life was the same thing: read the room. It’s the difference between being heard and being dismissed.
The relief barometer.
Libby has a test for whether she should have committed to something: if it gets canceled and her first feeling is relief, she shouldn’t have said yes.
She spent years saying yes to everything and eventually realized she was showing up for everyone else’s agenda at the expense of her own. It started showing up in her health before it showed up anywhere else. She pulled back. Started asking what actually pulled her attention rather than what simply demanded it. Those are not the same question.
For the women in this community running companies and households and creative practices and managing invisible labor on top of all of it, the yes problem is real. Every yes is a no to something else. The relief barometer doesn’t lie.
Seasons, not balance.
Libby plays golf, has since she was eleven. Some years she plays over a hundred rounds. This year, the clubs have barely moved.
She’s not in a golf season. She’s in another kind entirely. And she’s made peace with that.
Her version of ‘having it all’ shifts with the year, the quarter, the stage her kids are in, what the company needs. Some seasons the friendships get the time. Some seasons health is the priority. Some seasons work takes everything and the rest of life finds its own rhythm.
The goal isn’t balance. It’s knowing which season you’re in and making sure what matters most inside that season is actually getting what it needs.
Balance is bullshit (I think we should make this into a bumpersticker!). But seasons are real, and naming the one you’re in is more useful than chasing the one you think you should be in.
Feel most like yourself with people who really see you.
I asked Libby when she feels most like herself. She paused longer than she had on anything else in our conversation.
The answer: when she’s doing things she loves with people she loves. A big win at work with a team she respects. Quiet moments with family where there’s nothing to perform. Time with the women in her life who’ve known her long enough to show up without judgment when it matters most.
She talked about friends who are currently caregiving for aging parents. Friends whose careers are peaking while their personal lives feel uncertain. The range of what one generation of women holds at the same time. What she values in those friendships isn’t advice or strategy. It’s being seen.
That’s what we’re all looking for. In our partnerships, in our friendships, in this community. Someone who sees the whole picture and doesn’t flinch, who fully understands.
Listen to the full episode with Libby Leffler wherever you get your podcasts. Find First at ThisFirst.com and Libby on Instagram @ll
As always, thanks for being here…
Alexis
💸 First Promo for The Breadwinners community:
$100 off your prenup with First by using code BREAD100 at checkout.
Discount codes must be applied at checkout. No retroactive coupon codes or refunds applied.
Follow The Breadwinners on Instagram: @wearethebreadwinners
Rate and review wherever you listen - it helps more women find this show.