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 Entrepreneurs — but what we explore in this episode is the part of her story that accolades don’t capture. We dive into the inner work of adulthood and parenting: the moments when we realize we’re not validating what matters to our kids, even though we’ve spent our whole lives wishing others would validate what matters to us. We talk about how this work doesn’t necessarily get easier, but it becomes clearer… and how awareness is often the biggest shift of all. Jenny shares why she doesn’t believe in the word balance — and why blend is the more honest, compassionate way to approach working motherhood. We talk about what happens when we include our kids in the worlds we’re building, how it softens us, surprises us, and reveals the parts of ourselves still in need of slowing down, rewiring, or healing. It’s a warm, honest, deeply human conversation about ambition, presence, stress, creativity, and raising kids while still raising ourselves. Discount for listeners: Get 20% off Jenny’s kids’ luggage scooter company Roll Rider with code RollOK. This one is just SO GOOD. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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 had here. I was able to hear some of their innermost thoughts and what I am sharing here I hope puts perspective on how their minds work, they want magic, they want presence, they want us. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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, approachable way. She breaks it down and explains how the practice of meditation reshapes the nervous system, helps us see our thoughts instead of being ruled by them, and softens our reflexive thoughts and reactions (this is especially in motherhood when we find ourselves triggered or reactive to things we aren’t even aware of).  We each share our own before/after moments, including how meditation gave us perspective on the stories running in the background of our minds. If you’re curious about meditation but feel intimidated or confused - or if you’re like me, skeptical - then this is your starting point. You can also be guided by Jamie through her app Shift with Jamie. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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 often a disconnect between what any current school teaches and what kids actually need to thrive in real life: confidence, communication, social skills, executive functioning, curiosity, and a true love of learning. That curiosity is what led me to learn more about Alpha School. This week I am joined by its co-founder, MacKenzie Price, who started Alpha after watching her own daughters lose their love of learning early in elementary school, and decided to create a school that brought it back. Alpha uses Time-Back Learning, an approach where AI customizes academics to each child’s level. Core academics are completed in about two hours a day, which opens up the rest of the school day to what children truly need - time to explore interests, build real-world skills, collaborate, create, and grow at their own pace. In this episode, MacKenzie and I talk about why the legacy model is failing so many kids, what truly prepares children for life, how personalized pathways can unlock potential we’ve never tapped into, and what school could look like when we design it around how children actually learn. This conversation is not about choosing a school, it’s about reimagining an entire system. It’s about believing that kids deserve environments where they grow, stretch, collaborate, problem-solve, and discover their own agency. If you’ve ever felt like something about school just isn’t working… this episode will feel really exciting and will give a glimpse into what education could really become. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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 couple is truly remarkable. You feel safe, supported, and seen in a way I can only describe as being "held." That safety became the foundation for the most transformative experience I've ever had. I wanted this episode to talk about the neuroplasticity that occurs on a "journey" and the huge rewiring opportunity it gives us in the way we think. I also wanted it to help clarify the many misnomers around a psychedelic journey. Every "journey" is different and everyone experiences them differently. This journey was not ayahuasca. It didn't feel like I was out of control, I didn't feel sick, it felt gentle, grounding and deep. It was about sitting with myself, not escaping. Seeing what's been inside all along with the support of plant medicines and with guides who knew exactly how to hold the emotional and spiritual container for that to happen. In this episode you'll be introduced to the process, learn the purpose of it all and really get a glimpse into how special Zev and James are. It feels like the start of so much more that really touches on the truest expression of what this podcast has always been about: understanding where we "didn't turn out OK" and discovering what becomes possible when we finally turn toward those areas with understanding and love. James and Zev are extraordinary guides, an extraordinary couple and extraordinary humans. I'm so honored and excited to share this conversation - and this part of my story - with you. Learn more about your ad choices. Visit podcastchoices.com/adchoices