From Boss to Bossed - The Humble Pivot with Pat Riley

From Boss to Bossed - The Humble Pivot with Pat Riley

From Blue-Collar BS by Brad Herda and Steve Doyle

June 12, 2026 · 35 min · Episode 209

About this episode

Pat Riley discusses his transition from entrepreneurship to working for a company, challenging generational stereotypes and sharing insights on leadership and purpose.

Let's welcome Pat Riley onto the show this week. As an entrepreneur for years, Pat made a big pivot into working for someone else. That shift gives him a unique view from both the owner's and employee's side. This conversation challenged stereotypes we all hear Gen Z isn't lazy, Boomers aren't just selfish stock watchers, and bringing decades of experience into a new role doesn't mean you're stuck in old ways. Pat spent years owning and selling multiple businesses before transitioning into a sales management role. That transition from being the boss to having a boss required humility and finding leadership with values that aligned with his. He found both at Earth Development, bringing experience in building and leading organizations to his new position. We spend too much time labeling generations instead of recognizing what each one brings to the table. Pat's team is young and motivated by something bigger than just money. They understand the company's mission of keeping people safe in the winter. They care about purpose and community. Pat also talks about how he brought his AI expertise to transform a stagnant CRM system by simply asking technology how to solve problems…

People in this episode

Hosts: Brad Herda, Steve Doyle

Guest: Pat Riley

Topics covered

  • entrepreneurship
  • generational stereotypes
  • leadership
  • sales management
  • AI in business
  • college debt crisis

Keywords

  • entrepreneurship
  • leadership
  • generational stereotypes
  • AI
  • sales management
  • college debt

Mentioned in this episode

Organizations: Earth Development

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