What's Your Story with Jaime & Stan

What’s Your Story, Rob Cressy? From obituaries to AI, reinventing success on your own terms

Episode Summary

In this electrifying episode, we’re joined by Rob Cressy entrepreneur, content creator, and AI innovator who takes us through his rollercoaster journey from selling ads on an obituary website to leading a global movement. Rob shares how he walked away from a six-figure career to chase his dream of getting paid to talk about sports, built a media company from scratch, and embraced AI as his ultimate co-pilot all while staying grounded in heart, humanity, and relentless self-improvement. If you’ve ever felt stuck, uninspired, or unsure how to take that leap toward your dream life, this episode is your wake-up call.

Episode Notes

Rob shares how he walked away from a six-figure career to chase his dream of getting paid to talk about sports, built a media company from scratch, and embraced AI as his ultimate co-pilot all while staying grounded in heart, humanity, and relentless self-improvement.

If you’ve ever felt stuck, uninspired, or unsure how to take that leap toward your dream life, this episode is your wake-up call.

Key Topics Discussed:

Trading comfort for dreams:

How Rob quit a $250K/year job with zero clients, no website, and no backup plan to pursue his dream of talking sports for a living.
Why he believed selling ads on an obituary site was the hardest thing he’d ever do and why everything after felt easy.

Mindset overhaul: from survival to high performance:

How he built himself into a high performer, one micro habit at a time, starting with reading 30 minutes every morning (after realizing most CEOs read 60 books a year).
His game-changing approach to stacking tiny wins over time from waking up 3 minutes earlier each week to building a growth mindset, brick by brick.

AI, business growth, and “Soul Data”:

How Rob became a world-class AI innovator diving into ChatGPT the week it launched and instantly seeing the next decade of business unfold.
His "Human First AI" philosophy, why soul, heart, and human connection are what will separate leaders from the pack in the AI-driven world.
The concept of "Soul Data" how Rob infuses his core values, declarations, and vision into AI to preserve his voice, essence, and humanity.

Leading a Global Movement:

How a 3-day transformational coaching conference pushed Rob to redefine his identity from entrepreneur to leader of a global movement.
The one word that now defines his mission: Heart and how he’s building a "Heart First, Human First" movement for creators, entrepreneurs, and leaders.

Memorable Quotes

“It’s impossible that anything else will be harder than selling ads on an obituary website so I can do anything now.” – Rob Cressy
“The reason most people never achieve their dreams? They just don’t spend enough time with them.” – Rob Cressy
“AI doesn’t have heart. It doesn’t have soul. That’s why the future belongs to those who lead with humanity first.” – Rob Cressy

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Where to listen & watch:
YouTube: https://youtu.be/Ke6df1N4-H4
Apple Podcasts: https://tinyurl.com/mtkxjcez
Spotify: https://tinyurl.com/yhkw24v7
Amazon Music: https://tinyurl.com/2hnfynpm

Connect with Rob:
Website: www.robcressy.com
Instagram: www.instagram.com/rob_cressy
LinkedIn: www.linkedin.com/in/cressy/
Recommended Book: The Power of Consistency by Weldon Long

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