A Note on Luck, Timing, and Coincidence

While this publication is still in its early chapters, I want to use this piece to set a precedent. Consider this the "Read Me First" manual for every framework, mental model, and strategy I publish here.

After reflecting on my first batch of essays, I felt a strong need to anchor everything I write in a grounding reality.

Luck, timing, and coincidences wield a far greater influence over your trajectory than most people care to admit.

As much as I’d like to believe I’m exceptionally clever and adept at navigating the world around me, the truth is that luck, timing, and chance encounters have played a massive role in my early career. It would be disingenuous - and frankly, dangerous to your own journey - for me to downplay them.

If you haven’t read my manifesto, The Hand You Are Dealt, here is the short version:

At 18, I was kicked out of home. I started my working life in a boatyard, moved on to work as a signwriter for $14 an hour, and eventually launched an e-commerce brand that scaled to $60k per month. I leveraged that success to start a digital management firm, transitioned into software development, sold software IP, and was hired as a CTO by age 23. Today, I serve as the Chief Product & Technology Officer for that same private, board-funded business.

That sounds like a clean, linear rise. It wasn't. Here is what most people leave out of their trajectory.

Where Luck, Timing, and Coincidence Step In

These three forces have intersected with my life dozens of times, but three specific moments completely altered my trajectory:

1. The Luck (The 9th Attempt)

It took me nine separate attempts to build an e-commerce business that actually scaled. The hard work was in the relentless repetition - having the grit to launch store after store after eight consecutive failures.

The luck arrived on attempt number nine, when an organic social video I posted picked up 45,000 views overnight. That single algorithmic spike generated day-one revenue, validated the store, and essentially launched my entire trajectory into tech and business.

2. The Timing (The Pivot That Kept Me My Job)

The very first product I conceived and built after being hired as a CTO failed completely. My team and I spent 8 to 10 months developing it. We even engaged an expensive, top-tier agency for our go-to-market strategy. It flopped, and the entire project had to be shelved.

Fortunately, we had just begun early development on a second, unrelated product. The timing was so precise that we were able to pivot the entire team to this new build instantly. Because of that exact window of timing, the board didn't question the sunken capital or lost months on the first project. I kept my role and moved forward.

3. The Coincidence (The 9-Digit Casual Comment)

That second product - the one that saved the trajectory - wasn't even our idea.

During a routine meeting with a Tier-1 brand for a small side project, their Head of E-commerce made a offhand, casual complaint about a completely separate issue they were struggling with. It was pure coincidence that he voiced that specific pain point in that specific room. We caught the signal, built the solution, and that product became our core focus. Today, our board is pouring capital into it to position our business as a nine-figure acquisition target.

Why The Playbook Is Still Critical

None of the outcomes above happen without luck, timing, and coincidence.

However, you cannot build a life by sitting around waiting for random forces to make things happen. Weaved between those three pivotal moments were thousands of hours of intense labor, testing decisions, late nights, and uncomfortable moments.

That is what this blog is actually about.

My goal with The Unconventional Trajectory isn't to give you a magical formula that guarantees success. It is to provide you with the tactical frameworks, mental models, and decision-making tools needed to stay in the game long enough for luck to find you - and to ensure that when lightning strikes, you have the structure in place to capitalize on it and slingshot your trajectory forward.

Read the frameworks. Apply the models. But never forget the role of the cards you didn't draw.