What if you built two companies worth nearly $1 billion—only to realize there were things you would still change?

In this episode of At the End of the Day, host Chris Raimo sits down with John Hewitt, one of the most successful, and brutally honest, entrepreneurs in the franchising world. With 56 years in the tax and finance industry, John opens up about the wins, the losses, and the lessons behind building two powerhouse franchise brands: Jackson Hewitt and Liberty Tax.

Episode Overview

From taking an H&R Block course in college to eventually founding and selling two multi-million-dollar companies, John’s story is a masterclass in scaling, systems, and the mindset behind empire-building. But what makes this conversation especially valuable is John's willingness to share not just his wins, but what he’d do differently.

You’ll hear firsthand how he grew Jackson Hewitt and Liberty Tax to thousands of locations, took both public, and sold them for a combined $1 billion+. You’ll also hear cautionary tales about franchising pitfalls, team-building, and how even seasoned founders can hit walls.

In This Episode, You’ll Learn:

• How John went from tax student to industry titan
• The keys to building scalable franchise systems
• Common mistakes franchisors make, and how to avoid them
• What drives franchise success beyond just a business model
• John’s entrepreneurial mindset and how it evolved over 56 years
• The one thing he’d change if he could go back
• Why team culture and execution matter more than you think

Timestamps & Highlights

01:00 | The H&R Block beginnings and managing 250 locations
03:38 | Building Jackson Hewitt and Liberty Tax into national powerhouses
06:14 | The truth about entrepreneurship: challenges and rewards
09:48 | Insights into franchising: who it’s for and who should avoid it
13:07 | Final thoughts: John’s advice for entrepreneurs & what he’d do differently
Quote of the Episode

“Most people think success is about money. But success is about people—surrounding yourself with the right ones, and learning from the wrong ones.” – John Hewitt

Loyalty Brand links:
Facebooks: https://www.facebook.com/loyaltybrandsfranchises/
Instagram: https://www.instagram.com/loyalty_brands/
Twitter: https://twitter.com/@Loyalty_Brands
YouTube: https://www.youtube.com/@loyaltybrands
LinkedIn: https://www.linkedin.com/company/loyaltybrandsinc
John Hewitt links:
Facebooks: https://www.facebook.com/loyaltybrandsCEO/
LinkedIn: https://www.linkedin.com/in/john-t-hewitt-9917b7149/
Call to Action Book: https://loyaltybrands.com/free-icompete-book/
Connect with us – The Fire in Me Community
Website: https://thefireinme.com/
Email: [email protected]

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