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.
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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