About Rob Cressy

Human first,
lead with heart.

Rob Cressy is a human-first AI coach and keynote speaker. He helps entrepreneurs and their teams put AI to work in their business and leadership, with heart at the center.

Ways to work with Rob Read my story

Rob Cressy smiling and holding out a microphone on a rooftop patio

Rob Cressy, human-first AI coach, smiling with his arms wide open

Rob Cressy laughing behind a microphone during a podcast recording

01My story

From sports media to human-first AI.

I’ve been an entrepreneur for over 20 years, and one belief has guided all of it. The best results come when you lead with who you are.

That belief carried me from building a sports marketing agency to coaching people on personal growth and high performance, from the improv stage at Second City to keynote stages, and into AI the first week ChatGPT arrived.

The work that made me good at AI was the inner work I’d done for over 15 years before December 2022. Identity. Sacred standards. The daily practice of becoming a better person one day at a time. When AI showed up, all of that walked into the prompts with me, and the AI started reflecting it back.

The better the person, the better the AI. That realization is the foundation of every system I build, every coaching engagement I run, and every keynote I give. I come to AI as an entrepreneur and a coach. My work is helping you become the leader your business needs, with AI as the multiplier. We start with you, and the technology follows.

Today I do that from Sarasota, Florida, with founders and teams across the globe. Every day I get to help people see what’s possible for them and then go build it.

Sports mediaFounded Bacon Sports, a sports marketing agency, and spent 10 years helping brands market to sports fans.
The stageTrained in improv at Second City and as a speaker at Jesse Itzler’s Built to Speak.
The inner workCoached leaders and their teams on personal development and high performance: identity, standards, and the daily practice of becoming the best version of yourself.
Week one of ChatGPT Dec 2022Went all in on AI and has used it every day since.
TodayCoaching founders and teams, speaking on human-first AI, and hosting The Undeniable Leader podcast.

Within the first minute of using ChatGPT, I felt like I used the Internet for the first time. Immediately I saw the next decade of business and was all-in.

Rob Cressy

02What I bring

Where it all comes together.

Business perspective. Human understanding. New possibilities for you.

03How I teach AI

The Unlimited Method.

The human-first way I teach AI, in three steps.

Step 1

Personalize

Teach AI who you are. Your voice, your business, and your goals, so everything it creates sounds like you.

Step 2

Think

Think bigger with a strategic partner. Pressure test decisions, map your next move, and work through problems in minutes.

Step 3

Create

Create real work at a new speed. Content, systems, offers, and presentations, built fast and in your voice.

Get the free AI Playbook

04What I stand for

The values behind everything.

Radiate Positivity

Energy is transferable. Every interaction is a chance to spread joy.

Always Learning

Better today than yesterday, with a growth mindset that keeps moving forward.

Extreme Ownership

Accountable for everything in my world and every decision I make.

YES AND

The heart of improv. Build on each other’s ideas and create together.

Live in Action

1 is always greater than 0. Take the step, publish the post, do the thing.

Be Relentless

In the pursuit of excellence and whatever sets my soul on fire.

Do What’s Right

My Dad’s words every time I left the house. Integrity in who I am and what I do.

Talk with Candor

Open, honest, and grounded in trust. I tell you what you need to hear.

Let’s create what’s next.

Coaching, workshops, and keynotes for entrepreneurs and their teams.

Ways to work with Rob

Follow along: The Undeniable Leader podcast Undeniable newsletter YouTube

Human first, lead with heart.