Drewbie Wilson Tells Us How to Crush The Day

Author: Rich Bennett / Drewbie Wilson
Published: Mon 31 Mar 2025
Episode Link: https://www.conversationswithrichbennett.com/

Sponsored by Tar Heel Construction Group

Drewbie Wilson joins Rich Bennett to share how he turned his life around—from tipping the scales at 315 pounds to becoming a 7-figure sales leader and entrepreneur. He breaks down the mindset, discipline, and daily habits that help him (and his clients) crush the day before it crushes them. This episode is a must-listen for anyone in sales or business looking to level up with no gimmicks, just grit.

Guest: Drewbie Wilson

Drewbie Wilson is a sales expert, entrepreneur, podcast host, and author known for his straight-talk approach and relentless drive. After losing over 100 pounds and transforming his life, Drewbie applied that same discipline to business—rising from tech support to the C-suite and now leading his own consulting brand, Call The Damn Leads. He’s passionate about helping others crush their goals, one honest conversation at a time.

Main Topics:

· Drewbie Wilson’s personal weight loss journey and lifestyle transformation

· The origin and meaning behind “Crush the Day Before It Crushes You”

· Building a sales career from the ground up, including early experiences

· Transitioning from corporate life to entrepreneurship

· Sales training, discipline, and the importance of follow-up systems

· Overcoming fear and rejection in sales calls

· The difference between B2B and B2C sales strategies

· How to properly ask for referrals and the value of relationships

· Structuring daily routines for personal and professional success

· Lessons in motivation, gratitude, and leading by example

Resources mentioned: