Divorce, Dating, and $25M Exits with Jaclyn Johnson
Mon Dec 08 2025
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.
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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.