With a career spanning over 20 years at top companies like Square, Microsoft, Amazon, and Etsy, Dave Brown has mastered the art of leading creative teams and building impactful brands. After a successful run as the founder of his own agency and record label, he made the choice to step into a 9-to-5 role, embracing the stability and fresh challenges it brought. In this episode, Dave reflects on the pros and cons of this shift, his dedication to connecting deeply with customers, and Square’s recent billboard purchase above Mr. Beef (the restaurant where they film The Bear). Dave also shares insights on the spaces and routines that spark his creativity and his passion for mentoring others in their careers. Filled with humor, practical advice, and unique perspectives, Dave’s conversation with Ryan offers listeners a compelling look at the trade-offs between corporate life and hustle life along with the rewards of staying curious.