How Rick Cockerham’s AI Outsmarts Wall Street without Predicting a Thing

Rick Cockerham didn’t set out to ride the AI hype wave—he built A.N.N.I.E. to be different. His stock-trading AI system isn’t about prediction, but performance, using neural networks and genetic algorithms to behave like a savvy trader in real-time. In this Wantrepreneur to Entrepreneur Spotlight, Rick shares how a canceled hedge fund launch during the pandemic sparked a pivotal shift—transforming a Wall Street-caliber tool into an everyday investor’s secret weapon. From programming in C++ to defying conventional wisdom, Rick’s journey proves that trusting your vision, even when it goes against the grain, is sometimes the smartest trade you’ll ever make.

Hi, Rick Cockerham! Thanks for joining us today. Tell us about your business. Who do you serve, how do you serve them, and what's the impact that your business and work makes?

At AI-StockTrading.com, I help individual investors tap into the power of real-world AI to make smarter, more confident trading decisions. I’ve spent years building a stock trading system called A.N.N.I.E. (Artificial Neural Network Investing Expert), which uses evolutionary algorithms and neural networks—not predictions or hype—to identify high-probability trades. Every weekday, subscribers get a simple, actionable stock pick based on A.N.N.I.E.’s analysis of over 1,200 stocks. This isn’t paper trading or theory—A.N.N.I.E. has been trading live with real money and consistently beating the market. My goal is to give everyday investors an edge that was previously reserved for hedge funds and institutions. The impact? Users are empowered with transparent, AI-driven insights that remove emotion and guesswork from trading. It’s about making advanced AI accessible, understandable, and actually useful for regular people who want to grow their wealth without needing a finance degree or hours of research every day.

Tell us about the moment you finally felt like you went from wantrepreneur to entrepreneur.

I think I’ve had the entrepreneurial bug since the 6th grade. A friend and I got our hands on some peppermint and cinnamon oils, dipped toothpicks in them, and started selling packs to our classmates. It was my first profitable venture—until the teachers shut us down for running an unlicensed operation. But even then, I loved the thrill of creating something and having people actually want it. Fast forward a few decades and that same drive eventually led to A.N.N.I.E.—my AI stock trading system. I built it for myself at first, constantly refining the neural networks and genetic algorithms behind it. The real turning point—the moment I stopped being a wantrepreneur and truly became an entrepreneur—was when A.N.N.I.E. was consistently beating the market in live trading. It was making me enough money to quit my job and focus on the business full-time. That’s when I knew it wasn’t just a cool project or a pipe dream—it was a real product with real value. And that’s when I stopped dabbling and committed fully.

Describe the moment or period in your life/career that motivated you to make the entrepreneurial leap.

For me, it wasn’t one lightning-bolt moment—it was a slow burn. I’ve worked for a lot of startups over the years, and while I learned a ton, I always felt like I was building someone else’s vision. I’d pour everything into a product, only to watch decisions get made by people more interested in fundraising than creating something that actually worked. That disconnect wore on me. At some point, I realized I was tired of watching companies throw money at hype while overlooking real engineering. I had this AI I’d been developing quietly on my own—refining it in the background, not for show, but because I believed in the idea. And one day, I just knew: I’d rather take a risk on something real that I believe in than keep coasting on the corporate hamster wheel. That’s when I made the leap. Not because it was safe, but because it finally felt worth it.

Describe a tool, service, or software that has been a game-changer for your business. How does it contribute to your success?

One of the biggest misconceptions about AI in trading is that it should predict the future. That’s not how A.N.N.I.E. works—and honestly, I think that’s why it succeeds where so many others fail. A.N.N.I.E. isn’t trying to guess what a stock will do tomorrow. It’s trained to be a good trader. That’s a subtle but crucial distinction. Instead of making predictions, A.N.N.I.E. evolves strategies that consistently lead to profitable outcomes. It’s a behavioral model, not a crystal ball. It looks at each day's data and makes a decision based on patterns that have actually worked in the real world—not just in backtests, but in live trading.

We know that success is very often a non-linear path. Tell us about a failure, pivot point, or lesson that changed your course or direction and helped to get you where you are today.

Back in 2018, I set out to create a hedge fund powered by my AI trading system. I spent two years proving that it worked—meticulously tracking results, refining the system, and showing investors that it wasn’t just another flashy quant model. When it finally came time to pull the trigger and launch the fund… the pandemic hit. Everything froze. The investors backed off, the momentum evaporated, and the whole plan unraveled through no fault of the tech. I won’t lie—it crushed me. I was depressed for a month. After pouring years into building something real, it felt like the rug had been yanked out from under me. But eventually, I got back up and asked a different question: Who am I really trying to help? That’s when I pivoted. Instead of building A.N.N.I.E. for institutions and already-rich investors, I turned it into a tool for regular people—guys like me who just want a fair shot at growing their money. That shift changed everything. It not only opened up a new business model, it felt right. And now I get to wake up knowing I’m helping people who actually need it—not just padding another fund’s quarterly report.

What unconventional strategy did you employ that significantly impacted your business?

Most AI trading platforms try to predict the market. I went the opposite direction. The unconventional strategy I used was to stop trying to predict anything—and instead, train my AI to simply act like a good trader. I built A.N.N.I.E. using neural networks and a genetic algorithm that rewards behavior, not accuracy. It evolves trading strategies based on what actually works in the market—not on guessing future prices. That alone sets it apart from 99% of what's out there. On top of that, I wrote the entire system in C++ instead of Python. Everyone told me that was overkill, but I wanted maximum speed and control. Now A.N.N.I.E. can evaluate over 1,200 stocks in about a minute, with real-time decision making and zero fluff. So, between ditching prediction and doubling down on raw performance, I took a path most wouldn’t—and it worked.

What’s something you wish you knew sooner that you’d give as advice for aspiring or newer entrepreneurs?

Back in 1990, I was flipping through a Parts Express catalog and realized I could build an entire computer from the components listed. I put up flyers around campus and actually made a sale. Excited, I went to a business professor for advice. She told me, “The computer industry is very mature. There’s no way you can break into it.” And just like that, my enthusiasm died. Years later, I read Michael Dell’s story—he was building computers in his dorm room at the exact same time I was. Of course, we all know how that turned out for him. Looking back, I realized that professor wasn’t giving me facts—she was giving me doubts. She wasn’t saying it was impossible; she was saying it was going to be hard. But being young, I heard “don’t even try.” So here’s the advice I’d give any aspiring entrepreneur: Listen to people’s reasons, but never listen to their doubts. Filter out the fear. Keep the logic. If you believe in something and are willing to work for it, hard is not a reason to stop.

Want to dive deeper into Rick's work? Check out the links below!

• Visit AI Stock Trading's website: ai-stocktrading.com
• Connect with Rick on LinkedIn: Rick Cockerham
• Find AI Stock Trading on Facebook
• Find AI Stock Trading on X: @ANNIE_Trades