Libby Leffler, founder and CEO of First, joined host Katie Smith on episode 7 of Your Mom Does AI, a podcast that makes AI approachable for busy moms. Libby and Katie first met at Compass, before either of them had kids. In the episode they cover building an AI-native company, how Libby actually uses AI day to day, and what worries her most about it as a parent: privacy, consent, and knowing what's real.

Listen on Apple Podcasts or Spotify.

Building an AI-Native Company

Libby started working on First in 2022 and founded the company in 2023, which makes First what she calls a "post-GPT company." Before First she spent about 20 years in consumer technology at Google, Facebook, SoFi, and Compass. She says that gave her a front-row seat to earlier platform shifts: from the information web to the social web, and from desktop to mobile.

Her lesson from those shifts is to stay open and curious, and to listen to smart people you trust. At First, that meant hiring people who were eager to learn AI even if they didn't have direct experience with it yet. It also means being willing to rework the roadmap when the technology moves. "We're not throwing the baby out with the bathwater, but you can't be precious about it," Libby says. "The world's just changing too fast."

AI Should Sharpen Your Thinking, Not Replace It

Libby admits she was a slower adopter of AI tools. Early on, the output was full of made-up, unsourced claims and never sounded like her. What changed was learning to be specific about what she wants: don't pander, don't make things up, show the sources, keep it concise.

Today she uses AI for fast research, for pressure-testing ideas, and for spotting blind spots. When she was asked to go on air with about 90 minutes' notice, AI helped her get oriented quickly so she could focus on deeper research and calls to people she trusts. But she draws a firm line around writing and high-stakes thinking: "There are many things in our life that really do deserve careful, thoughtful synthesis and strategy, much of which only comes from your experience."

At home, she uses an AI assistant to put together a Sunday "lookout" of her kids' week: pickups, practices, permission slips, and school events she might otherwise forget. She also uses it to turn her daughter's weekly spelling list into word scrambles and word searches, decorated with whatever unicorns and rainbows her daughter asks for. She keeps that use deliberately contained: the assistant doesn't get unfettered access to her email, and it doesn't send emails or buy things on her behalf.

Asked what keeps her up at night, Libby didn't hesitate: "privacy, safety, security, control." She's concerned about how casually people upload photos to AI tools, whether it's a selfie for a viral trend or a picture of someone else's kids at sports practice. Children can't consent to their photos being used, which is why you won't find photos of her kids' faces on her public social media.

Libby doesn't think the answer is avoiding technology altogether. It's understanding what you're agreeing to before you click: what the privacy settings are, how long your data is kept, and whether the tool is training on photos of you and your family.

When Everything Is Polished, Authenticity Matters

Libby shared a story from First. Our free consultations are run by real people on our team, with no AI involved. Even so, one caller was convinced they were talking to a bot and asked to be transferred to a human. A second team member called them back and finished the consultation, and at the end the caller said they didn't think First should be using AI on calls about something this sensitive. Neither call had used any AI.

For Libby, the takeaway is that "in a world where now everything can be so polished, authenticity matters more than ever." Telling what's real from what's generated is a tension she expects all of us to deal with for a long time.

Two AI Terms, Translated for Moms

Katie asked Libby to explain two AI terms in mom language, and she came prepared.

  • Hallucination: when your kid comes home from school and tells you, with complete confidence, about something that absolutely did not happen. The problem isn't imagination; it's the confidence. That's why Libby asks AI tools for their sources and double-checks them, especially for research.
  • Prompt engineering: the difference between telling the sitter "make sure they're in bed on time" and leaving full instructions: dinner is on the counter, one small sweet for dessert, teeth brushed by 7:15, two books, lights out at 7:30. The first is a recipe for iPads, milkshakes, and a 10 p.m. bedtime. The more context you give, the closer the result is to what you wanted.

Where Prenups Come In

Libby describes First as an AI platform for consumer legal services that supports life's most important moments, starting with prenuptial agreements. First is available in 46 states and Washington, D.C. Couples can get anything from a fully bespoke agreement to a self-serve custom prenup that meets their state's requirements.

Some couples come to First just days before their wedding. Libby lists some of the reasons: they're eloping, there's an immigration timeline, a job change means they need to get on a spouse's health insurance, or it's late December and they want to marry before the end of the tax year.

The same habits Libby recommends for using AI apply to a prenup. Be specific about what matters to you, because more context leads to a better result. Check where the information comes from. And for the decisions with the highest stakes, rely on real expertise. If you want to read more about where AI does and doesn't belong in wedding planning, start with Avoid AI Slop in Wedding Planning: Get a Real Prenup. If equity or startup shares are part of your financial picture, see our guide to prenups and tech equity.

Listen to the Full Episode

The full conversation is about 51 minutes and also covers motherhood, staying offline, and Libby's go-to s'mores technique (she likes her marshmallows burnt). Listen to Privacy, Prenups, and Pro Level Prompting with Libby Leffler on Apple Podcasts or Spotify, and follow Your Mom Does AI for more conversations about AI for busy moms.

Ready to start your prenup? See pricing and plans or get started with First.