There’s a strange, powerful truth that often goes unsaid: most of our success, failure, identity, even relevance — is bound to the era in which we’re born.
I was born at a time that happened to align with the rise of the personal computer, the evolution of networking, and the early waves of the Internet. I grew up alongside it. My teenage years were filled with bulletin boards and local area networks, and by the time I entered the workforce, the digital transformation had begun. The timeline fit. The wind was at my back.
Entrepreneurship found me early too. I hit my stride during the explosion of multi-level marketing and the rise of the self-help scene. Those environments — flawed and messy as they were — gave me tools: confidence in public speaking, an understanding of social persuasion, and most of all, a belief that being different could be powerful. Even pro wrestling played its part. It taught me about persona — the value of a character who stands out and leans in.
These experiences weren’t universal. They were specific to my time. My life is a living experiment with a sample size of one — n=1.
Timeless Wisdom vs. Timely Application
I’ve always had mentors. A supportive family. A spouse who stands by me. And I’ve drawn heavily from Stoicism and spiritual teachings that have endured for centuries. But I don’t mistake timeless wisdom for universal utility.
What worked for Marcus Aurelius or even my own mentors doesn’t always work here, now, for me. That’s why nearly every major move I’ve made — in business, in life — has been driven by experimentation. Scientific method. Trial and error. Observing, adjusting, iterating. Always adjusting for context.
I hunt for asymmetry: small bets with big upsides. And I often use a barbell strategy — thank you, Ray Dalio — allocating the bulk of my resources into stable, known returns while reserving the rest for moonshots. Life, like any investment portfolio, is about managing risk exposure.
And I do it all as asynchronously as possible. Not just in how I work, but in how I think. Time is a tool. I refuse to be trapped by the tyranny of the immediate.
Lessons That Don’t Translate
If I had been born twenty years earlier, I might have missed the digital wave entirely. Or maybe I would have found a different current — maybe mainframes or military networks. If I were born twenty years later, I might have missed the golden age of early web entrepreneurship, but perhaps mobile and app ecosystems would have taken its place.
That’s the point. What worked for me worked because of my timeline. But it might not work for anyone else — even if it looks appealing from the outside.
That’s why I’m cautious about what I try to pass on. I don’t offer a playbook. I offer tools. Mental models. Systems thinking. Frameworks that others can adapt and test for themselves. And I encourage every single person to apply n=1 experimentation to those tools. Because the context in which you live matters just as much — or more — than the tool you use.
Legacy Without Monuments
When my time is up, I don’t need monuments. I’m not chasing statues or street names.
What I do hope for is simpler, quieter. I hope that others see my life as one lived with compassion, generosity, and love. I hope they learn from what I’ve tried, and test those learnings against their own lives. I hope they make better decisions, kinder impacts, smarter plays.
I hope they live their own n=1 experiment, tuned to their time, their truth.
Because the only real legacy is what echoes forward in the lives of others — not through imitation, but through adaptation.
* AI tools were used as a research assistant for this content, but human moderation and writing are also included. The included images are AI-generated.
Not Quite Random 