Brothers in Business: Benson Chidester on Risk, Faith & Scale | EP 083

In this episode, I sit down with Benson Chidester — former CEO of Elite CEOs and now Director of Sales at Acquisition.com — to talk about what separates good entrepreneurs from great operators.

We go deep on the lessons he’s learned working alongside Alex and Leila Hormozi, what door-to-door sales taught him about grit, and how growing up in a strict household shaped his drive and discipline.

From risking it all to betting on yourself, Benson reveals why most people stay average — and how to break through the comfort ceiling to reach your next level.

If you’ve ever felt stuck, scared to take the next big leap, or unsure how to lead your team at scale — this episode is a must-watch.

Timestamps:

00:00 Intro — Discipline, risk, and growth

03:30 Lessons from strict parenting

06:45 What door-to-door sales really teaches you

10:25 Why people stop growing once they hit “good enough”

13:40 Lessons from working with Alex & Leila Hormozi

17:00 Breaking beliefs and scaling sales teams

22:10 The hidden cost of doing nothing

28:00 Faith, family, and staying grounded

33:10 The power of consistency in business and fitness

38:00 Risk, reward, and learning to think like a billionaire

44:30 What separates billion-dollar operators

51:00 Why most entrepreneurs fail to pivot

57:00 Inside the record-breaking book launch

1:02:00 Final thoughts — Doing the hard things

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