Audio Player

Rich Bennett / Drewbie WilsonDrewbie Wilson Tells Us How to Crush The Day

Use Up/Down Arrow keys to increase or decrease volume.

00:00

0:00 / 1:05:15

1. Drewbie Wilson Tells Us How to Crush The Day Rich Bennett / Drewbie Wilson 1:05:15

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, gr

Send us a text

Emily Adolph and Ona Crow are the co-creators of Nourish & Connect, an event designed to foster meaningful connections in a supportive and empowering environment. NOURISH & CONNECT – The Soul Lift

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
Rocketbook
SquadCast

Contests & Giveaways

Subscribe by Email

Most Recent Episodes

April 1, 2025

Becky Galli & Polly Surhoff on 25 Years of Autism Impact

Sponsored by Freedom Federal Credit Union In this heartfelt episode, Becky Galli and Polly Winde Surhoff reflect on 25 powerful years of impact through Pathfinders for Autism—a nonprofit born from...

Listen · 41:33

March 27, 2025

Magical Vacations Made Easy with Julie Shaffer

Sponsored by Daniel McGhee and The Victory Team In this feel-good episode, Rich Bennett sits down with Travel advisor and mom of three, Julie Shaffer, to talk all things family travel. From Disney...

Listen · 53:29

March 25, 2025

Andrew Serra’s Powerful Tale Of 1911’s Deadliest Fire

Sponsored by Eco-Cool HVAC Step into history with author and retired firefighter Andrew Serra as he joins Rich Bennett to discuss Hell’s Hundred Acres, his gripping novel about the 1911 Triangle...

Listen · 1:06:14

Load More Episodes

Rich Bennett Podcaster

I'm a Marine Corps Veteran, Professional DJ, Entrepreneur, and Professional Podcaster.

I started the podcast “Harford County Living” in 2015, 3 years after launching the positive news website harfordcountyliving.com. A few years later I started getting requests from people outside of Maryland to come on the show as guests and the podcast became “Harford County Living with Rich Bennett”. Needless to say, more requests came in and a few people suggested to me that I needed to expand the podcast and change the name again and “Conversations with Rich Bennett” was born.