Chapter 6: "Systems Over Luck"
Chapter 6: "Systems Over Luck"
So we've established that calculated risks beat playing it safe, and that scientific thinking beats wishful thinking. But here's where everything crystallizes into something revolutionary: Poker isn't gambling—it's a startup. Travel isn't luck—it's engineering. And you don't manifest extraordinary experiences—you build systems that make them inevitable over time.
Welcome to my Moonshot Poker Manifesto, which became my Moonshot Life Manifesto: Process over vibes. Edge over ego. Systems over hope.
This isn't about getting lucky or finding shortcuts. This is about thinking like a founder at the felt and on the road—building sustainable, repeatable systems for creating value, whether that value is measured in chips or in life experiences.
This chapter is about how I stopped hoping for good fortune and started engineering it.
Think about it: What do successful startups and successful poker players have in common? They both focus obsessively on process, they test hypotheses systematically, they iterate based on data, and they think in terms of expected value over long time horizons.
A startup doesn't say "I hope customers like our product." It says "We're going to test seventeen different value propositions, measure user engagement across twelve metrics, and optimize for sustainable growth based on what the data tells us."
That's exactly how I started approaching poker. Instead of "I hope I get good cards," it became "I'm going to systematically exploit opponent tendencies, manage my bankroll like a CFO, and make decisions based on mathematical edges rather than gut feelings."
Here's a specific example: I developed what I called my "Leak Detection System." Every session, I tracked not just wins and losses, but specific decision categories: bluff frequency, fold rate to 3-bets, position-based aggression, tilt indicators.
Within three months, the data revealed patterns I never would have noticed through casual observation. I was folding too much in late position, bluffing too little on dry boards, and playing too passively after winning big pots.
Each insight became a system improvement. Instead of trying to remember to "play more aggressively," I created specific triggers: "In late position with no action, raise any two cards 40% of the time." Quantified, measurable, systematic.
The same systems thinking transformed my travel experiences. People always told me I was "lucky" to have such amazing trips, to meet interesting people, to discover hidden gems. But luck had nothing to do with it.
I engineered those "lucky" experiences through systematic preparation, just like a startup engineers product-market fit through systematic customer development.
Take the Fair Isle trip. From the outside, it looked spontaneous, adventurous, maybe even reckless. But behind that apparent spontaneity was a comprehensive system for remote destination research.
I had systems for: Weather pattern analysis (best months, backup dates), logistics coordination (multi-modal transport contingencies), accommodation research (not just where to stay, but backup options), local contact development (connecting with people before arrival), gear optimization (what to bring for maximum flexibility).
The "luck" of getting perfect weather? I had monitored patterns for six months. The "luck" of meeting fascinating locals? I had researched community events and reached out in advance. The "luck" of having meaningful experiences? I had designed activities specifically to create space for reflection and discovery.
Even the decision to scale back on writing during 2023 was systematic. I created what I called a "Content Value Matrix"—tracking the time invested in documentation versus the experiential value of being fully present.
The data was clear: Below a certain threshold of documentation time, I could be more present without losing the essential insights. Above that threshold, I was trading experience for content—a negative ROI trade.
Here's where the startup mindset gets really powerful: You learn to focus on decision quality rather than short-term results. Because in both poker and entrepreneurship, you can make perfect decisions and still have bad outcomes in the short term.
A good poker player doesn't judge their play by whether they won or lost individual hands. They judge their play by whether they made +EV decisions consistently. The outcomes are just noise; the process is the signal.
The same principle applies to travel. I stopped judging trips by whether every moment was Instagram-perfect. Instead, I judged them by whether I followed my systems for preparation, presence, and integration of experiences.
Sometimes my best-systematized trips had challenging moments—flight delays, weather issues, plans that didn't work out. But because I had systems for adapting to unexpected situations, those challenges often led to the most meaningful discoveries.
It's like pocket aces losing to a two-outer on the river. Bad outcome, but absolutely correct decision to go all-in. The loss doesn't make the decision wrong—it makes the system stronger through stress-testing.
That Eastern Europe trip where I folded my original itinerary? By my old metrics, it was a failure—I "wasted" months of planning. By my new process metrics, it was a success—I had systems in place for recognizing when to pivot, and I executed them perfectly.
The trip became extraordinary not despite changing plans, but because I had built flexibility into my systems from the beginning.
The hardest part of systems thinking is subordinating your ego to the data. Your ego wants to be right, to trust instincts, to take credit for successes and blame bad luck for failures. But systems thinking demands intellectual honesty.
In startups, they call this "killing your darlings"—abandoning ideas you love because the data shows they don't work. In poker, it's folding hands that "feel" good because the math says they're -EV. In travel, it's changing plans that took months to develop because current conditions call for something different.
I remember a poker session where I'd spent weeks preparing for a particular tournament—studying opponent tendencies, planning my strategy, visualizing key scenarios. But fifteen minutes into play, I realized the dynamics were completely different than expected.
My ego wanted to stick with the plan. I'd invested so much preparation! But my systems said: "Sunk costs are irrelevant. What strategy gives you the best edge against these actual opponents in these actual conditions?"
I threw out weeks of preparation and adapted in real-time. It felt uncomfortable, almost like admitting failure. But I cashed in that tournament precisely because I prioritized edge over ego.
The same principle applies to travel systems. Sometimes your research points to one type of experience, but when you arrive, the optimal choice is something completely different.
In Gibraltar, my systems had identified several "must-see" historical sites. But my real-time assessment system—watching Skyelark's joy in that simple dirt dog park—revealed that sometimes the most meaningful experiences are the ones that don't make it into guidebooks.
Here's where the startup metaphor becomes more than metaphor—it becomes a complete philosophy for approaching life. Moonshot thinking isn't about taking crazy risks. It's about building systems so robust that what looks impossible to others becomes inevitable to you.
Google X doesn't hope for breakthrough innovations. They systematically identify problems worth solving, develop hypotheses for 10x solutions, and iterate rapidly based on evidence. That became my template for both poker and travel.
That 110-day world cruise wasn't a lucky opportunity—it was the result of systems I'd built for identifying and capitalizing on extended travel possibilities. I had financial systems (saving strategies, bankroll management), logistical systems (mail forwarding, bill automation), and experience optimization systems (research methods, documentation balance).
When the opportunity appeared, I didn't have to hope I could make it work. I knew I could, because I'd engineered the capability systematically over time.
The same with my poker evolution. I didn't hope to become a better player—I systematically identified skill gaps, developed training protocols, measured improvement, and iterated based on results.
So what's the practical takeaway from systems over luck? It's this: Stop hoping for extraordinary experiences and start engineering them. Build systems for preparation, execution, and adaptation. Measure what matters. Iterate based on evidence.
But systems aren't just about efficiency—they're about sustainability. Anyone can have one amazing trip or one great poker session. Systems create the capability for consistent excellence over time.
The systems I developed for poker made me a better traveler. The systems I developed for travel made me a better poker player. Both made me a better person—more disciplined, more analytical, more adaptable.
Because ultimately, building systems is building character. It's training yourself to think long-term, to subordinate impulses to strategy, to find edges that others miss because they're not looking systematically.
In our next section, we'll shift from strategic thinking to philosophical reflection. We'll explore how motion—physical, intellectual, and spiritual—becomes the foundation for a life well-lived. Because once you have systems for engineering extraordinary experiences, the question becomes: What do you want those experiences to teach you about yourself and the world?
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"Moonshots aren't about luck—they're about building systems so robust that extraordinary becomes ordinary."
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