102: Jason Bay | Don’t Follow Your Passion, Follow Your Effort

On today’s episode of The Edge of Excellence, Matt talks to Jason Bay, founder and CEO of Outbound Squad, a sales coach and trainer for B2B reps and sales teams.


Jason had an extremely structured childhood, thanks to his father being a former Marine and his mother, an immigrant from Hong Kong. This contributed to his early success as valedictorian at his high school, as well as his later work with world-class sales teams at companies like Gong, Medallia, Zoom, CBRE, Monday.com, GoGuardian, and many others.

He’ll explain why starting his own company was like a form of rebellion against his parents. He’ll also discuss his definition of excellence, referencing the documentary Jiro Dreams of Sushi. As a student in college, he went through an identity crisis, but College Works came to the rescue. You’ll discover how and why he joined College Works, as well as how he quickly mastered the intricacies of running a painting business. After that, the sales experience became an obsession for him. He’ll talk about how he honed his sales skills and progressed in his sales profession.

After working as a corporate marketing director and sales trainer at College Works, Jason decided to start his own painting business. While he shares great advice on starting a successful business, he also delves into the lessons he learned from his initial mistakes. He’ll transition into how he started a consulting firm and how it evolved into sales training, first for small businesses and eventually for Fortune 500 companies.

Join Matt and Jason for a fascinating discussion about honing your sales skills, the process of starting a business, taking risks, and being extremely resourceful in your twenties.


What You Will Learn In This Show:

  • Jason’s definition of excellence.
  • How to put your skills to the test early in your career.
  • Strategies for finding a new job right away.
  • The most important lessons Jason learned at College Works and how they’ve impacted his career.
  • The importance of choosing the right partner.
  • And so much more…

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