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In this episode, Ryan Gilbert shares how he escaped seven years in supply chain by building Workspaces, a newsletter showcasing creative home offices that now reaches 15,000+ subscribers. After countless tech job rejections from Wisconsin, Ryan discovered that building in public could open doors that resumes couldn't.We dive deep into his journey from secretly starting a pandemic project to landing roles at Product Hunt, experiencing a hollow acquisition with Loops, buying back his creation for

Design management is evolving faster than ever. Kris Puckett, the "Ted Lasso of design managers" at Shopify, shares an unfiltered look at navigating this shift - from bombing his Figma interview to embracing AI tools he once resisted.In this candid conversation, we explore why companies now demand player-coaches over pure managers, how to survive brutal job searches (publicly), and why "vibe coding" represents the future of design leadership. Kris reveals how AI finally unlocked his 20-year dream of

Matt Varughese, CEO of 8020 and former petroleum engineering student, shares his unconventional journey from retail work at Nike to building one of the most respected Webflow agencies in the industry. This conversation explores how strategic naivety, cold emailing, and the courage to reject traditional career paths led to working with clients like Ellen DeGeneres, Dr. Andrew Huberman, and Chance the Rapper.Key TakeawaysStrategic ignorance as a superpower: Not knowing how hard agency life would be

Designer, drummer, and creative entrepreneur Kyle Barrett shares his unconventional journey from Whiteboard's first employee to building a successful freelance practice specializing in music industry design. This conversation explores the reality of multi-creative careers, the challenges of freelance creative work, and building sustainable practice that honors your full creative identity rather than forcing specialization.Key TakeawaysCreative careers rarely follow linear paths: Kyle's journey from

When startup marketing leader Peter Sum turned 34, he had a moment of reckoning that changed everything. Despite 15 years of success in tech, he couldn't shake the feeling that he wasn't fully bringing himself to his work. Today, Peter runs Kenzie Club, hosting sold-out supper clubs in Berlin and redefining what career success actually means.This conversation explores the messy reality of career transitions, from the privilege required to make big changes to the fear of burning bridges to your old

Show OverviewDesigner, dad, and creative director Chris Conley shares his unconventional journey from Apple retail to co-founding Thread, a multi-disciplinary creative studio in Lancaster, Pennsylvania. This conversation explores the reality of creative career pivots, the challenges of transitioning from maker to manager, and building sustainable creative businesses rooted in authentic relationships.Key TakeawaysCareer transitions are rarely linear: Chris's path from Apple retail to music production