The Pool's Empty and Betty Sue's Giving The Ick

The Pool's Empty and Betty Sue's Giving The Ick

From Drinks After Work with Shannon and Deb by Shannon Tipton

April 3, 2026 · 36 min · Episode 22

About this episode

Shannon and Deborah discuss the realities of leaving corporate America to start a business, including power dynamics, challenges, and resources for entrepreneurs.

Pop the tab on something cold and settle in — it's time for another round of Drinks After Work! This time, we're talking all about: Power dynamics at work — from Betty Sue in finance to team leads on power trips When to leave corporate America and go out on your own The ick of entrepreneurship: trading one set of problems for another The harsh realities no one tells you (spoiler: healthcare costs will make you cry) Why the system wasn't built to support entrepreneurs — and how to survive anyway How to know if you're built for the solo life (and what to do if you're not) In this episode, Shannon and Deborah dive into the messy reality of leaving corporate America to start your own business. It sounds amazing when you're sitting in your corporate chair collecting a corporate paycheck, but then you realize you're just trading one set of problems. They break down the things nobody warns you about — healthcare costs that want it all upfront, business insurance requirements, wearing every single hat, and the scam artists promising you can make $5 million in a year if you just buy their course. But it's not all doom and gloom — they also share real resources and remind you that failing…

People in this episode

Hosts: Shannon Tipton, Deborah

Topics covered

  • power dynamics at work
  • entrepreneurship
  • leaving corporate America
  • healthcare costs
  • business challenges
  • resources for entrepreneurs

Keywords

  • entrepreneurship
  • corporate America
  • power dynamics
  • healthcare costs
  • business insurance
  • small business resources

Mentioned in this episode

Organizations: Small Business Association

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