We Didn't Turn Out OK with Jennie Monness

In this episode, I got to Zoom-hang with three women who feel like instant soul-friends: Allison Williams (Girls, M3GAN, Get Out) and her lifelong best friends Hope Kremer (early childhood educator) and Jaymie Oppenheim (therapist). It’s a four-way Zoom, so it feels exactly like being dropped into a private group chat, the kind where nothing is curated and everything is real. We talk about momming on meds, realistic expectations changing our parenting lives, confidence and bag size (yes, really), the pressure we put on moments that maybe don’t deserve it, and the ways we all carry high stakes without even realizing it. What surprised me most wasn’t just how honest the conversation was,  it was how familiar it felt. Different lives, different paths, same nervous systems. Same fears. Same gratitude. Same joy. Same constant recalibration of who we are and who we’re becoming as mothers. And that’s exactly the energy they’re bringing into the world with what they’ve created through Landlines: connection, honesty, and a sense of you’re not doing this alone. This episode doesn’t need a long explanation. Just know this: It feels like listening to a lifelong group text thread between three best friends who became moms -  and suddenly realizing it sounds exactly like your own. And that’s the magic. Join their substack.  Listen to their pod. Learn more about your ad choices. Visit podcastchoices.com/adchoices

In this episode, Jamie Kolnick peels back every layer. As a mom of three, Jamie is constantly navigating her own growth and healing, shaped by profound loss after losing both of her parents and her brother. Many know her as the founder of the beloved children’s music brand Jam with Jamie. What you may not know is how much inner work she has done - and continues to do - to make sense of grief, belonging, and identity. Rather than summarizing this conversation, I want to urge you to listen. This is one of the most raw episodes yet. Jamie opens up about losing her brother at just 13 years old, how the attention and popularity surrounding that loss shaped her understanding of belonging, and how those early experiences still echo in her life today, as a parent, a partner, and a public figure on social media. Through therapy, medication, deep reflection, and honest self-inquiry, Jamie has come into herself in ways that feel both brave and deeply relatable. She speaks candidly about couples therapy, learning her triggers, the lifelong work of feeling “enough,” and what it really means to live alongside loss rather than try to move past it. Jamie also shares about spearheading Little Jam Fest, offering classes through Jam with Jamie, and her ongoing fundraising work with the Reach for the Stars Foundation. This episode will stay with you. Learn more about your ad choices. Visit podcastchoices.com/adchoices

In this episode, I sit down with my sisters for what started as a “get to know us” conversation, and quickly turned into something much deeper. At some point, we forgot we were recording and simply began reminiscing. It felt like therapy. It felt grounding. And it felt especially meaningful during a time when we’re navigating some of the hardest things we’ve faced together. What kept coming back to us was this: getting through life together has always been our anchor. We reflect on our childhood and the sisterhood we share, one that, surprisingly, was never rooted in competition or jealousy. We don’t remember being at odds (aside from a few scratch marks from toddler toy disputes). As a mom of two young girls close in age, currently deep in the trenches of sibling rivalry, I found myself wondering how our experience was so different… and what, if anything, I can learn from it. Listening back to this episode, what moves me most are the moments you can’t fully hear: the quiet looks, the tears, the shared smiles. Those nuances are what hold this conversation together. I hope this episode gives you a glimpse into my upbringing, the shaping experience of being the middle of two sisters, and the quiet magic that sibling relationships, especially sisterhood, can hold. You’ll also meet my sisters: Katy Leinoff, my younger sister, is a collage artist living in Florida with her husband and their 3-year-old daughter. She’s currently seven months pregnant with her second child. Lindsey Lamchick, my older sister, is a real estate agent, title owner, and the founder of Project Disco Ball, a nonprofit inspired by her journey through breast cancer. She lives in Florida with her husband, their 16-year-old twins, and their 6-year-old daughter. There will be more sister episodes in the future, I’m already sort of hoping I can create a spin off podcast for the three of us to have regular sessions. Learn more about your ad choices. Visit podcastchoices.com/adchoices

This week I’m joined by the hilarious, honest NYC moms behind the podcast Mic’d & Medicated, Eva Heyman and Caroline Leventhal, in what starts as a conversation about sleepaway camp turns into something much deeper (and very funny). Sleepaway camp might sound niche, but it’s a topic I get asked about constantly ever since I started sharing about how we were looking at camp for Tess this upcoming summer (I can’t believe she’s leaving us so soon!). I get questions  from parents all over the world. Why do we send our kids away for the summer? Who is it really for? Our kids? Us? Both? We unpack the phenomenon behind camp and all the questions that come with it: – What age is “right”? – Co-ed or single gender? – How long is too long? – Is camp about independence, identity, resilience… or parents needing space to breathe? – And how much of our own childhood experiences shape the decision? We also go inward, sharing whether we went to camp ourselves, the experiences that stayed with us (good and hard), and how those memories quietly inform the choices we’re making now as parents. For me, camp was the first place I truly felt like I belonged. It shaped who I became, gave me lifelong friendships, and remains one of the most formative chapters of my life. That belief deeply influenced the schools I chose for my daughters and the camps we explored together. This episode is real, reflective, laugh-out-loud funny, and full of nuance. It’s a conversation about sleepaway camp not just as a parenting decision but as a decision about giving your child an experience where they discover who they are, who they can be without us and what it feels like to truly belong.  Learn more about your ad choices. Visit podcastchoices.com/adchoices

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