070 Changing from SMB To Enterprise

with John Hewitt

· PATH TO ENTERPRISE

What if everything you think you know about scaling a business is wrong? In this eye-opening episode, we dive deep with John Hewitt, who built not one but two tax preparation empires—Jackson Hewitt and Liberty Tax Services—scaling to over 6,000 locations before a $500 million exit.

The journey from founder to empire builder isn't just about better systems or smarter strategies. It's about transforming yourself from a hands-on entrepreneur into what Hewitt calls a "chief of chiefs"—someone who can lead leaders.

Here's what most get wrong: they focus on rules instead of principles, systems instead of people, and control instead of autonomy. As Hewitt puts it, "Losers love rules." Winners, on the other hand, understand that principles trump policies every time.

The secret to scaling? It starts with people. Hire for attitude, not just aptitude. Use situational interview questions that reveal character, not just competence. Then, be quick to fire and quick to promote. Let your team struggle sometimes—it's how they grow.

When it comes to systems, think bigger. Plan five years out, then work backward to three years, then one. Build self-sustaining feedback loops. And here's a counterintuitive truth: if you're hitting every goal, your goals are too low.

Most importantly, maintain direct communication as you grow. Hold regular fireside chats. Create channels where every level of the organization can hear directly from leadership. Because messages that pass through layers of management get diluted or distorted.

Watch the Full Episode on Building Business Empires with expert John Hewitt below:

Follow us to watch live on YouTube and LinkedIn or listen to episodes on Apple Podcasts and Spotify.