Leading Beyond the Grind: Lessons in Learning Before Earning, Health, Hustle, & 20-Hour Work Week I Direct Application with Matt Harrington
ABOUT OUR GUEST
Bennett Maxwell is a serial entrepreneur whose journey defies the traditional career playbook. Raised in Utah as one of nine siblings in a single-parent household, Bennett learned the art of sales and grit at a young age - knocking doors, selling products, and hustling long before he ever founded a company.
After a two-year Mormon mission in Mexico, Bennett returned home, briefly pursued pre-med, then dropped out to follow his passion for communication and sales. From pest control, AT&T, and smart-home systems to solar, he built his career across multiple industries - eventually co-founding and selling a solar company in his early twenties.
In 2021, he purchased a tiny, delivery-only cookie shop called Dirty Dough, and within three years helped scale the brand to 450+ franchises sold and 100+ locations opened. Along the way, he sparked a very public “cookie war” that drew national attention and only fueled the brand’s momentum.
Dirty Dough was later acquired by Craveworthy Brands, where Bennett now helps franchisees grow scalable models across multiple high-potential concepts. Behind the scenes, Bennett also transformed his life physically —losing 120+ pounds, restructuring his mindset, and building his own version of sustainability through what he calls the 20-hour work week grind. His approach blends Eastern philosophy, resilience practices, and radical transparency - making his leadership philosophy as unconventional as his entrepreneurial path.
IN THIS EPISODE
Matt and Bennett dive into a fast-paced, energizing conversation about:
Learning before earning: Why Bennett intentionally changed industries every year in his 20s
Radical transparency: Including sharing near-bankruptcy stories publicly
Hiring & firing: Choosing the right leaders—and recovering from choosing the wrong ones
Advisory boards & mentorship: Why leaders need people smarter than them
Resilience & mindset: How failure shaped him more than success
Health & leadership: Losing 120 pounds, quieting the mind, and why physical health fuels business success
The 20-hour work week: What it actually looks like—and why he believes most work can be automated • Reinvention: How to pivot again and again without burning out
What’s next: The future of franchising, CPG, and Craveworthy Brands
CONNECT WITH BENNETT MAXWELL
Website: https://bennettmaxwell.com/
LinkedIn: https://www.linkedin.com/in/bennett-maxwell-703717126/
Craveworthy Brands: https://craveworthybrands.com/
CONNECT WITH MATT / HARRINGTON BRANDS
Website: https://www.HarringtonBrands.com
Direct Application Podcast Page: https://www.harringtonbrands.com/directapplication
LinkedIn: https://www.linkedin.com/in/matthrrngtn/
TikTok: https://www.tiktok.com/@matthrrngtn
Direct Application is where leadership theory meets real-life practice. Host Matt Harrington brings on CEOs, founders, creatives, and change agents to unpack the strategies, failures, habits, and breakthroughs that leaders can apply directly to their own work.
