Coaching with Tyler Chesser

You’re already successful. You’ve built something you’re proud of. But deep down, you know there’s more — more impact, more growth, more freedom, more life to live.

Right now, you might feel:

• Stuck — like you’ve hit an invisible ceiling in your business or personal growth.

• Frustrated — knowing you’re capable of more but unsure how to unlock it.

• Spread thin — juggling too much without feeling like you’re making enough meaningful progress.

I know that feeling — because I’ve been there.
And I know how to get you out of it.

This isn’t generic advice or a cookie-cutter program. This is high-level, highly personal coaching designed for leaders who are ready to break through to extraordinary.

We’ll focus on three pillars:

1. Clarity – Defining exactly what you want, why it matters, and the high-leverage moves that will get you there.

2. Strategy – Building a precise plan to scale your results without scaling your stress.

3. Accountability – Relentless support and challenge so you execute at the highest level, week after week.

You’ll finally break free from the plateau holding you back.

1. You’ll think bigger — and act on it — without second-guessing yourself.

2. You’ll create a business that fuels your life instead of consuming it.

3. You’ll make more progress in 12 months than most people do in 5 years.

How It Works

1. Apply – Fill out a brief application so I can understand your goals and challenges.

2. Discovery Call – If it’s a fit, we’ll schedule a free discovery session to dive deeper.

3. The Work Begins – We’ll meet regularly (virtually or in person) to create, execute, and adjust your strategy until you achieve your initial breakthrough & beyond.

Who I Work Best With

I coach high-achieving entrepreneurs, investors, and business leaders who are:

• Already successful, but feel like they have another gear they haven’t hit yet.

• Committed to growth — willing to be challenged and take action.

• Ready to invest time, energy, and resources into their next level.

Why Me

• $200M+ portfolio operator — I’ve built and lead a thriving private equity real estate business.

• Proven transformation — I’ve gone from “successful but stuck” to living my mission at the highest level.

• Student of the best — I’ve invested hundreds of thousands into my own growth with world-class mentors and coaches.

• Track record of results — My clients consistently achieve breakthroughs in revenue, impact, and fulfillment.