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

Send us a text

Tar Heel Construction Group
Harford County Living Stamp of Approval for Roofing, Siding and Exterior Services

Disclaimer: This post contains affiliate links. If you make a purchase, I may receive a commission at no extra cost to you.

Support the show

Rate & Review on Apple Podcasts

Follow the Conversations with Rich Bennett podcast on Social Media:
Facebook – Conversations with Rich Bennett
Facebook Group (Join the conversation) – Conversations with Rich Bennett podcast group | Facebook
Twitter – Conversations with Rich Bennett
Instagram – @conversationswithrichbennett
TikTok – CWRB (@conversationsrichbennett) | TikTok

Sponsors, Affiliates, and ways we pay the bills:
Hosted on Buzzsprout
SquadCast

Subscribe by Email