Wantrepreneur to Entrepreneur | Start and Grow Your Own Business 1197: This guy RETIRED thanks to an AI stock trader he built! Here's how YOU can use it too w/ Rick Cockerham
What if you could build an AI powerful enough to beat the stock market—and retire because of it? That’s exactly what Rick Cockerham did. In this episode, Rick shares how he built ANNIE, his custom-built AI stock trader that marries genetic algorithms with neural networks to consistently outperform the market. From early experiments in the ‘90s to achieving real-world investment success, Rick’s story is a masterclass in patience, innovation, and bringing tech to everyday people.
This episode goes beyond just AI and stocks—it’s a powerful lens into product-market fit, building with integrity, and serving the underserved. If you're building a business that solves a real-world problem, this one’s for you.
💡 What You'll Take Away For YOUR Business
- 🧠 How one man’s lifelong passion for AI turned into a retirement-worthy business
- 🔄 Why building “traders” instead of “predictors” is a winning entrepreneurial mindset
- 🚀 The surprising business decision that led Rick to serve individuals over high-net-worth investors
- 💸 How to make powerful tech accessible without big price tags ($20/month!)
- 📉 Why removing your own bias from your product might be the best thing you do
- 🛠️ The difference between a generalized AI model and a purpose-built agent—and what that means for your business
📝 About the Guest
Rick Cockerham has been coding since 1980 and exploring AI since the mid-’90s—long before it was trendy. He built ANNIE, an AI trading system that consistently beat the market and allowed him to retire early. Today, he shares those same signals with everyday investors at ai-stocktrading.com. One of the few developers creating original AI architectures from scratch, Rick’s goal is to use smart code to level the playing field in investing. When not coding, he enjoys woodworking and practicing judo in Austin.
🎯 Rick’s BEST Piece of Advice for Wantrepreneurs and Entrepreneurs
“Don’t listen to people’s doubts—listen to their reasons. Then work around the reasons.”
Key Takeaways:
- 🚧 Doubt ≠ valid limitation—distinguish real obstacles from fear-based projections
- 🧠 You don’t need permission to pursue your idea—just data and courage
- 🔄 Every “no” is either a challenge to solve or an idea to refine
📢 Memorable Quotes
- “I’m obviously a much worse stock trader than she is at this point.” – Rick Cockerham
- “My biases were terrible... so I gave ANNIE full control.” – Rick Cockerham
- “I didn’t want to just help millionaires get richer—I wanted to help people like me.”
💡 Actionable Takeaways
- ✅ Start building now—even if it takes years to perfect
- ✅ Remove your personal bias from your product and let data guide decisions
- ✅ Serve the people who need your solution, not just the ones who can afford it
- ✅ Don’t overcomplicate your offer—sometimes a daily text is enough to build a great business
🔗 Links & Resources