As a co-founder of Hims and Hers, Joe helped take a direct-to-consumer healthcare brand public at a $1.6 billion valuation. Now as CEO of Dutch, he is reshaping how pet owners access veterinary care through telemedicine. Joe has spent 15 years learning what it actually takes to build something that lasts, and in this episode, he holds nothing back. Charles and Joe dig into the real mechanics of building a venture-backed business, from knowing when to burn everything down and start over, to hiring the right kind of crazy, to leading a team through failure without losing them. Joe breaks down the pivot that took Hims from a product nobody wanted to a $200 million valuation in a single month, and what he would do completely differently if he had to do it all again. Together, they get into why execution beats ideas every time, why dreaming too small is just as dangerous as dreaming too big, and why the best businesses are built on a simple formula: faster, cheaper, better. This is not a highlight reel. It is a masterclass in what entrepreneurship actually looks like from the inside. KEY TAKEAWAYS: Why execution and perseverance matter more than the original idea when building a scalable business How Joe took Hims from a failing product to a $200 million valuation in just one month after a full rebrand The hiring mindset that separates startup survivors from people who need stability Why dreaming too small is one of the most underrated mistakes founders make How faster, cheaper, and better remains the most reliable formula for building something people actually want KEY POINTS: 01:12 : Building venture-backed businesses: Joe breaks down what VCs actually look for, while Charles connects it to the grind most entrepreneurs overlook. 03:49 : The power of the pivot: Joe walks through the moment Hims almost died and what it took to start over, while Charles explores why most founders wait too long to make that call. 06:21 : Leading a team through uncertainty: Joe shares what it feels like to jump off a cliff and hope for the best, while Charles digs into how you bring your people with you. 08:49 : Hiring for startups: Joe explains how to spot someone built for the chaos of early stage companies, while Charles challenges the conventional wisdom around who makes a great hire. 48:06 : Lessons from a billion dollar exit: Joe reflects on ringing the NYSE bell and what he wishes he had known sooner, while Charles pushes him on what would have made it faster. 51:58 : Dreaming bigger: Joe makes the case for setting goals that feel impossible, while Charles ties it back to building a business that is genuinely in service to others.