Episode 36: Business and Life Partners Olivia Landau and Kyle Simon on Delegating at Home and Work

Listen to this episode from We Didn't Turn Out OK with Jennie Monness on Spotify. 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 a thriving business. How even her parents doubted her early on - and how that early lack of belief shaped her journey as a founder.  Why they wish they had given themselves more time to adjust to parenthood instead of jumping back into work too quickly. The surprising freedom they’ve found in releasing control—delegating at home and in business—and why it doesn’t make them any less of entrepreneurs. The ways their “not okay-ness” shows up—Olivia as a recovering perfectionist, Kyle as someone working on being more present—and how they’re navigating those patterns as new parents. It’s an honest, funny, and relatable look at the intersection of marriage, entrepreneurship, and parenthood—proving that success isn’t about doing it all yourself, but about learning when to lean on each other and your village. Learn more about your ad choices. Visit podcastchoices.com/adchoices