Conversations with Rich Bennett Drewbie Wilson Tells Us How to Crush The Day
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:
Guest & Host
- Drewbie Wilson – Entrepreneur, sales expert, and author
- Rich Bennett – Host of Conversations with Rich Bennett
Businesses & Brands
- Call The Damn Leads – Drewbie Wilson’s consulting brand and website
- Harford County Living – Podcast presentation sponsor
- Tar Heel Construction Group – Sponsor mentioned in the ad
Harford County Living Stamp of Approval for Roofing, Siding and Exterior Services
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