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