How to start a $40m a Year Door to Door Business with Kenny Crosby

This week, I chat with Kenny Crosby, CEO and founder of Home Nerds, who's spent 18 years mastering the art of door-to-door sales and is now building a tech product to disrupt the entire home services industry. In this episode, Kenny shares how a single $180 cable sale after three weeks of straight rejection hooked him on sales for life-leading him from knocking doors in high school to training hundreds of salespeople and generating millions in revenue. We dive deep into what separates the top 1% of salespeople from everyone else, why Kenny would take someone with 10 years of door-to-door experience over an Ivy League graduate, and how he learned to see himself as a "servant" rather than a salesperson. He opens up about losing nearly $2 million and an entire sales team, the spiritual journey that followed (including Friday nights with mushrooms and Grateful Dead albums), and why he believes every entrepreneur gets "shaken to their core" right before they're about to level up. Kenny also reveals how he's building a fully integrated marketplace for home services that could compete with Angie and HomeAdvisor, and shares his counterintuitive approach to business growth—selling first, then figuring out how to deliver. This conversation will challenge everything you think you know about sales, rejection, and what it really takes to build something that lasts. If you’re on your own journey of breaking free from the 9–5 and building something real, check out Put Out Content — my high-level coaching and content strategy program designed to help creators, founders, and entrepreneurs realize their potential through powerful storytelling and systems. 🎯 Access the tools, offers, and ways to work with me: https://stan.store/deepaksharma 📲 Enjoyed the episode? Share it and tag me on IG: @deepaksharma.co Thanks for tuning in. And just remember... It’s Not That Deep.