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 $1, and finally joining beehiiv. Along the way, we explore why he manually posts everything (6,000+ tweets and counting), the psychological complexity of selling your own creation, and how becoming a father to baby Lily has reshaped his approach to creative risk.

Big Takeaways:

• How side projects can bypass traditional hiring gatekeepers
• The power of piggybacking on others' audiences for growth
• Why consistency matters more than perfection (publishing every weekend since April 2020)
• The hidden costs of acquisition success
• How parenthood changes your relationship with creative risk
• Why manual presence beats automation for authentic connection