Unlike Me

Today’s guest is Jaclyn Johnson, a serial entrepreneur, investor, and the founder of Cherub, a new platform reimagining how early-stage founders and investors connect. Before Cherub, Jaclyn built and exited Create & Cultivate, leading her to over $25M of exits and cementing her as one of the most influential builders in modern women’s business culture.In this conversation, we get into the real stuff behind the highlight reel, from navigating divorce and dating in the middle of a very public career, to the unsexy realities of selling a company, starting again, and figuring out what you really want your life to look like on the other side. We also talk about how she thinks about modern entrepreneurship, where the creator and founder worlds are colliding, and why building a brand that actually means something has never been more important.

In this episode, I sit down with Mallory Edens, founder of Little Ray Media, a production company focused on elevating stories by and about women in film and television. We discuss her passion for reshaping which stories get told in Hollywood and who gets to tell them. Mallory also opens up about a traumatic accident that changed her trajectory and strengthened her resilience and clarity of purpose. We talk about coming from an NBA family, acknowledging the privilege that comes with that, while still intentionally carving out her own lane and building something that is distinctly hers.

In this episode, I sit down with Josh Cohen, CEO of Pinpoint - one of my portfolio companies that just raised a $2.5 million seed round from top investors, as well as KSI with his Sidemen Fund. We talk about how Pinpoint is helping brands convert their social audiences into paying customers and why I think it’s one of the most underrated tools out there right now. Josh and I dive into what efficient growth looks like in today’s digital-first world and how smart brands are simplifying their funnel to drive real results. If you’re a founder of an online brand, or just a lover of great businesses and sharp founders, this one’s for you.

In this solo episode, I sit down for an unfiltered Q&A from my work at the intersection of venture capital and the creator economy. I talk about what I’ve learned from building on my own, the importance of failing quickly, and how those failures have shaped the way I think about business, ownership, and growth. If you’re a founder, creator, or just curious about what it’s really like behind the scenes, this one’s for you.

In this episode, I sit down with Megan Lightcap, partner at Slow Ventures, which recently raised its $64 million creator fund to back creator-led businesses. While both Megan and I operate at the intersection of venture capital and the creator economy, we approach it from very different angles, which made for a dynamic and thought-provoking conversation. We unpack the structure of Slow Ventures, explore what ownership looks like in the digitally native age, and discuss the evolving relationship between creators and capital.