Caldwell Leadership Group

I started as a part‑time associate.
I became a president.

Let me show you how to close that gap.

You set the target. I'll help you hit it.

My Story

I didn't build a mansion.
I built something better.

I'm not going to show you a sports car or promise you a seven-figure income. What I will show you is how to build real value — in your career, in your relationships, and in yourself.

I started on the floor of a retail store, part-time, with no roadmap and no mentor. Over 20 years I worked my way from associate to store manager, to District Manager overseeing hundreds of locations, and eventually to President of two software companies.

Nobody handed it to me. I figured it out through hard work, the right mindset, and learning what great leadership actually looks like. That's what I want to give you.

20+

Years of leadership experience

350+

Retail locations led as District Manager

Software company president

Inc. 5000 Fastest Growing Companies — led truDigital to this honor two consecutive years

0→1

Started part-time. Built a career worth being proud of.

Is This For You?

This isn't about getting rich.
It's about getting clear.

Clear on who you are. Clear on where you're going. Clear on the kind of leader and person you want to become.

🎯

You're hungry but directionless

You know you're capable of more, but no one has ever shown you how to get there.

📈

You want to move up

You're in sales, leadership, or running your own business and you're ready to level up.

🧭

You want purpose, not just a paycheck

You want to build a career worth having and a life worth living — not just chase a number.

How It Works

Simple. Personal. Real.

No courses. No worksheets. Just honest conversations and a clear path forward.

You Set the Target

We start with a free 30-minute call. You tell me where you are and where you want to go. No pitch. No pressure.

We Build the Plan

Together we map out what's standing in your way and what needs to change — in your mindset, your habits, and your approach.

I Help You Hit It

We work together one-on-one, meeting regularly, until you get where you're going. Your goals. Your timeline. Your life.

Ready to take the first step?

A free 30-minute conversation. No obligation. Just a talk that could change everything.

Book My Free Call

Or email directly: [email protected]

I started as a part‑time associate.I became a president.

I didn't build a mansion.I built something better.

This isn't about getting rich.It's about getting clear.