My Story
From Playground to Boardroom and Back: Rediscovering the Joy of Building
The Beginning (1980s)
It started with pure curiosity. Back in the 1980s, my high school had exactly one computer—aResearch Machines 380Z tucked away in the science teacher's room. During lunch breaks and spare moments, a few of us would crowd around that machine, writing games in BASIC and discovering the magic of making things happen with code.
When the VIC-20 came out, I convinced my parents to get me one. I was hooked. There was something intoxicating about the immediate feedback loop—type some code, run it, see what happens. Fix it, improve it, make it do something new.
"I felt so alive in those early days—the pure excitement of building and creating was everything."
Early Career: From Bins to Systems Programming
That passion led me to do whatever it took to stay close to computers. I got a job atSperry Univac in the computer room, just to be around the machines. I hung around, asked questions, and eventually wrangled my way into a trainee position as a computer operator.
From there, I climbed the ladder: systems programmer, writing operating systems, earning a computing degree. Loading tapes, booting mainframes, fixing programs, building and installing brand new systems—it was all pure joy. Every day brought new challenges, new problems to solve, new systems to understand.
The Technical Evolution: Riding the Wave of Change
In those early days, I worked alongside programmers who had coded in assembler for their entire 25-year careers. But then the changes started accelerating. We shifted from assembler to C. A few years later, C++. Then something else.
I watched as we moved from hierarchical database handlers to the emergence of relational databases. Each transition brought new paradigms, new ways of thinking, new skills to master. The pace of change was exhilarating but also intimidating.
I was keeping up fine—that wasn't the problem. I was adapting, learning, growing with each new technology. But a nagging fear was beginning to take root.
The Fear & The Pivot: A Strategic Retreat
The fear that gripped me was more insidious than any technical challenge: what would happen when I reached 50? Would my aging brain still be able to cope with this relentless pace of change? I'd seen older programmers struggle, and I convinced myself that cognitive decline would eventually make adaptation impossible.
So I made what seemed like a strategic retreat: I moved into management. People, I reasoned, don't change as fast as programming languages. Leadership principles are timeless. It felt like the smart, mature decision.
"At first, I loved management too. But over the next twenty years, something slowly died inside me."
Twenty Years of Corporate Life: Success Without Soul
Corporate life became increasingly inane, sucking the life and fun out of work. The joy I'd felt in those early days—the pure excitement of building and creating—was gone. I was successful by conventional measures: climbing the ladder, managing larger teams, handling bigger budgets.
But I felt empty. The connection between effort and outcome became abstract. The immediate feedback loop of code—write, test, see it work—was replaced by meetings about meetings, strategies about strategies, and decisions that took months to implement.
I told myself this was what growing up looked like. This was maturity, responsibility, the natural progression of a career. But deep down, I knew something vital was missing.
The AI Renaissance: Everything Changed Again
Then AI arrived, and everything changed again. The very force that seemed to threaten my management career also handed me back my first love. All those things that once filled me with dread—mastering endless new languages, tools, and integrations—AI now handles effortlessly.
The cognitive load I feared my aging brain couldn't handle? AI carries it. But what AI can't provide is vision, passion, or the distinctly human drive to create something meaningful. It can't articulate a product spec from a glimmer of an idea, and it can't orchestrate an army of AI agents to bring that vision to life.
"It turns out my old-school discipline and strategic thinking weren't obsolete—they were the missing piece."
The kid who used to sneak into the computer room during lunch breaks had grown into someone who could conduct an orchestra of artificial intelligence. And ironically, at 50+, I'm more productive and creative than I ever was in my twenties.
Building Again: The Joy Returns
In the last five months, while still working my day job, I've become a one-person studio. I've built5 apps, 4 websites, 4 agent suites, and a market-leading AI SEO framework. No employees, no investors, no offices—just vision, discipline, and an army of AI assistants I've learned to orchestrate.
Every morning I wake up excited about what I'm going to build. The immediate feedback loop is back—idea, implementation, result. But now it's amplified by AI that can execute the tedious parts while I focus on strategy, architecture, and creative problem-solving.
"For the first time in twenty years, I'm having fun again. I'm alive again. I'm doing work that matters."
The Mission: Building in Public, Inspiring Others
My story isn't just about career pivots or technological disruption. It's about how our deepest fears can become our greatest opportunities, how the longest way around can be the shortest way home, and how it's never too late to reclaim what makes you feel most alive.
I'm building in public to show that the very thing you're running from might be exactly what you need to run toward. If someone who spent 20 years afraid of being left behind by technology can now orchestrate AI to build at unprecedented scale, then what's possible for you?
Key Lessons Learned
- •The longest way around became the shortest way home - My detour through management gave me strategic thinking that AI can't replicate
- •Your biggest fear might be your greatest opportunity - The cognitive challenges I feared became AI's strength
- •Experience + AI = Unprecedented leverage - Decades of context make AI orchestration possible
- •It's never too late to reclaim your passion - What made you feel alive once can make you feel alive again
What's Next: The Future is Being Built
My goal is audacious: reach $1 billion in portfolio value by 2030. Not through a single unicorn startup, but through a diversified portfolio of 10-20 AI-powered businesses, each generating $5-50M ARR.
This isn't just about the money. It's about proving a new model of entrepreneurship is possible. We're at the dawn of the AI era, and I believe the future belongs to solo operators who can orchestrate intelligent systems to build at unprecedented scale.
Every step of this journey is documented transparently. Every win, every failure, every lesson learned—all shared publicly. Because if I can show the playbook, others can replicate and surpass what I'm doing. That's the real goal.
Join the Journey
Whether you're facing your own career transition, wrestling with technological change, or simply curious about what's possible when experience meets AI—I'd love to have you along for the ride.