We Didn't Turn Out OK with Jennie Monness

Today’s conversation with Jenny Fleiss is one that stayed with me long after we stopped recording. You may know Jenny as the co-founder behind major ventures like Rent the Runway and Jetblack, or recently from Roll Rider, the kids’ luggage company she dreamed up with her children. She’s also been recognized with awards such as Inc.’s 30 Under 30, Fortune’s 40 Under 40, and Most Powerful Women Entr...

This was the most I have learned from any guest so far. It was a 45 minute episode cut down to 12 minutes because of how moving this entire conversation was I felt compelled to keep the majority of it private. What I left in, I hope helps give you ideas for questions you can ask your own kids, letting them know you are curious about what they think and that it sparks conversations like the one I h...

This episode is all about rewiring ourselves. In this episode, I sit down with mind shifter and meditation coach Jamie Graber for the meditation conversation I’ve always wanted but never heard: a true back-to-basics, “start at square one” guide to what meditation actually is and how it rewires us as parents and people. I have always wanted someone to talk to me about meditation in the most basic,...

Many parents feel it: that the current education system doesn’t fully reflect how kids actually learn. We’re craving something more aligned, more human, and more empowering, a model where children feel engaged, capable, and genuinely excited to learn because the experience itself is meaningful. I love my girls’ school and feel privileged to have been able to choose it. But I also feel there’s ofte...

This episode is one that I have been waiting to release, because it introduces one of the the most meaningful experience I've ever had. Last spring, I experienced a guided psychedelic journey with James Gangemi and Zev Eisenberg, the couple behind Heart Openers. They are not only gifted guides individually, but their partnership, the way they hold space together, and the energy they bring as a cou...

In this episode I sit down with Brynn Putnam and Kevin Thau for a conversation about ambition, reinvention, blended family life, and what it really means to build connection at home. Brynn is the entrepreneur behind Mirror - the interactive fitness company acquired by Lululemon - and now the creator of The Board, a new tool designed to help families stay connected in a tech-saturated world. A form...

Rebecca Minkoff is a designer, founder, best-selling author of Fearless, co-founder of the Female Founder Collective, host of Superwomen with Rebecca Minkoff, and mom of four. In this episode, Rebecca opens up about what it really took to build her vision - from hand-sewing pieces in her apartment and styling clients to fund her dreams, to the moment she could finally stop checking her bank accoun...

At just 23 years old, Chloe Harrouche was diagnosed with breast cancer. Instead of spiraling or feeling defined by the diagnosis, she chose to meet her journey with purpose, trusting that meaning would reveal itself on the other side. A decade later, that belief became the foundation for The Lanby, her concierge medical company created to bridge the gap between medicine and wellness, bringing toge...

Michael Perry could be introduced as the founder of Maple, the creator of KIT (acquired by Shopify), and a Forbes 30 Under 30 entrepreneur. But he’ll tell you the only introduction that matters is: husband to an incredible wife and father to two amazing sons. Michael found himself on food stamps in his 20s, sold cars for a living, and only dreamed of the symbols of success - financial security, th...

In this episode, I’m answering a mix of questions I’ve gotten from you - things like: “Why does my kid’s behavior trigger me so much?” “How do I know if I’m reacting to them or to something in me?” “What do I do when they refuse to apologize?” I share a real moment in the car after apple picking where I slipped into that familiar place of making their emotions about my expectations. Not because I...

What happens when you build a business with your spouse before you even start dating? For Olivia Landau and Kyle Simon, co-founders of The Clear Cut, that was the foundation of their love story, their multi-million-dollar company—and now, their parenting journey. In this episode, Olivia and Kyle open up about: How Kyle believed in Olivia’s idea before she did, pushing her to grow a blog hobby into...

Imagine getting an inside glimpse into the dynamic between a mother and daughter—their reflections on who they are, where it all comes from, and how it shapes the way they show up in their own parenting. Imagine hearing not only the beauty, but also the “not so okay” parts, spoken with honesty and without hiding behind perfection. That’s exactly what you’ll hear in this episode with Lynn Shabinsky...

You guys sent in your questions, he answered! Everything from finding time for intimacy, what he feels changed the most since becoming parents and what it's like to be married to someone on social media. This one is short but sweet so I'll keep the description the same. Let us know what you think and what Matt should answer next time! Learn more about your ad choices. Visit podcastchoices.com/adch...

In this episode I sit down with Lucie Fink - lifestyle host, podcast host of The Real Stuff and, who I like to call, an epic story teller. I was first drawn to Lucie because of her incredible way of telling stories, not just the way she shared the brands she believed in but how she shared her life. It’s sometimes silly, often beautifully edited but also so authentic and real. Her shift into mother...

In this episode, I sit down with Beth Gaskill, the reading and learning specialist behind Big City Readers. We dig into the disservice many schools unintentionally create when it comes to teaching reading - and how that often leads to a “third grade slump” - when children can no longer keep up and we learn that they need a more comprehensive tool box. Beth explains why this happens, and what paren...

In my first-ever solo episode, I’m sharing something deeply personal — my journey with anxiety, medication, and what it’s been like to come off Zoloft after nearly half my life. This conversation isn’t the full story of how I got here — that’s for future episodes. There’s a deeper beginning, one rooted in a lifetime of people-pleasing, seeking acceptance, and slowly losing sight of who I really wa...

In this episode, I sit down with Alyssa Blask Campbell - founder of Seed and Sew, host of the Voices of Your Village podcast, and bestselling author of Tiny Humans, Big Emotions and the upcoming Big Kids, Bigger Feelings. A mom of two, Alyssa has spent years researching emotional intelligence in children - only to realize that many adults, including herself, never had the tools modeled for them in...

Ever wonder how you’ll ever bridge the gap between you and your spouse’s wildly different ways of handling emotions and challenges? Me too. That's why this episode is for you, me, all of us. In this deeply honest episode, I sit down with journalist Mosheh Oinounou—who you may know as Mosheh of Mo’ News—and his wife, my dear friend, marketing agent Alex Sall. We talk about how they’ve built their r...

As someone who believes in letting gross motor development unfold naturally—without rushing babies into positions they can’t get into (or out of) themselves—I’ve always had questions about how we support movement in early childhood. So in this episode, I sat down with the amazing pediatric physical therapist behind Tots on Target, Dr. Allison Mell, to dig into all of it. I’ve followed Tots on Targ...

What if the toys our kids play with could help shape them into more compassionate, balanced, and open-hearted ? In this episode, I sit down with Hart & Hero founders—and fellow moms—Chanie Brod and Musya Eckhaus to explore how toys can do so much more than just entertain. We dive into the quiet power of care, the beauty of duality, and how to bridge the gender play gap in a world that too often pu...

When I tell you that this may be one of the most moving conversations on We Didn’t Turn Out Ok so far, I’m still not doing it justice. Having Whitney Port on brought me back to growing up what felt like with her—from watching The Hills, where she seemed to live in an alternate world from my "Varsity Blues" suburbs in NJ to following her journey as she began filming for The City, where she carved h...

In this episode, I sit down with Dale and Annabel - the funny, real and deeply honest voices behind We Are More Than Moms, a community and podcast that supports moms in navigating identity, ambition, and the messy in-between moments of modern motherhood. We talk about the many layers that shift when we become moms - from how we see ourselves to how we compare (to other moms, our pre-mom selves, ev...

This episode is really special to me. I got to sit down with Emily Oster — someone whose work has been a constant companion in my parenting journey. Emily is an economist, bestselling author, and professor at Brown University who has become a trusted voice for parents looking to make informed, grounded decisions. You might know her from her books Expecting Better, Cribsheet, The Family Firm, and T...

The Conscious Mom, where do I start? Back in 2020, when I was supporting other moms through virtual groups—craving a bit of that support for myself—I stumbled upon Erin Morrison, a.k.a. The Conscious Mom, on Instagram. What started as a digital connection during COVID quickly became a real friendship, even though we had never met in person. Fast forward five years, countless DMs, and near-misses i...

In this episode, I’m joined by Katia Pryce, the powerhouse founder and CEO of DanceBody, a dance-based fitness brand built on the belief that movement is medicine—something I deeply resonate with. What struck me most in our conversation was learning how DanceBody was born from Katia’s rock bottom moment. After moving to New York in her early twenties with dreams of being on Broadway, Katia landed...