I scribbled this quote in my notebook at the end of 2023.

I was sitting in my London flat, staring at two completely different futures.

Path one:

Stay in the UK. (Try) build a consumer fintech startup. Chase the Silicon Valley dream.

Path two:

Move back to Cape Town. Take over an established wealth management firm. Build something unconventional.

One felt sexy and entrepreneurial.

The other felt like I was settling.

Spoiler alert:

I chose wrong according to conventional startup wisdom.

But 18 months later, I've never been more certain about a decision in my life.

Because I finally understand what luck surface area actually means.

And how maximizing it changes everything.

Luck Surface Area

Shiny objects

For five years, I was the definition of a wannabe founder.

Sitting in my matchbox apartment, constantly tinkering but never shipping.

Hospitality apps that went nowhere.

Crypto projects that made no sense.

Content ideas that felt forced.

SaaS products in spaces I knew nothing about.

I was throwing spaghetti at the wall, hoping something would stick.

But nothing did.

Not because I wasn't working hard enough.

Not because the ideas weren't technically sound.

But because I had zero conviction about any of them.

I was chasing shiny objects instead of building something real.

Every weekend felt like pushing a boulder uphill.

Every project felt like swimming upstream.

Every conversation with potential users felt like I was trying to convince myself as much as them.

I spent 5 years hitting my head against the wall, wondering why nothing clicked.

The opportunity

Then came the opportunity with BRWM.

A 35-year-old wealth management firm in Cape Town.

On paper, it looked like the opposite of everything I thought I wanted.

No venture capital glamour.

No Silicon Valley status.

No TechCrunch headlines.

Just an established business managing wealth for high-net-worth clients.

But it felt different when I put my ego aside and really considered it.

For the first time in five years, I had immediate, unshakeable conviction.

I could see exactly how I'd transform the business.

I could envision the AI systems I'd build.

I could picture the full-stack automation.

I could feel that this was something I'd be naturally good at.

Everything seemed to line up.

Matthew McConaughey writes about moments when "everything we look up to comes down to our level, and everything we look down upon rises up to our level."

That's exactly what happened to me.

The tech startup world I'd been idealizing suddenly seemed less mystical, more human.

The traditional wealth management industry I'd dismissed as unsexy rose up to reveal its true potential.

I wasn't chasing someone else's definition of success anymore.

I was finally seeing my own path clearly.

Probabilities

Luck surface area isn't about finding the easiest path.

It's about finding the path where the most good things can happen to you.

It's about maximizing the probability that you'll get lucky.

The uncomfortable truth: success requires luck, no matter how hard you work.

Social media tells you that grinding harder guarantees results.

That's bullshit.

You can work 80-hour weeks on the wrong thing and get nowhere.

You can work 40-hour weeks on the right thing and build an empire.

The difference is choosing the path where luck can actually find you.

The calculus

When I mapped out both paths, the math was obvious.

Startup path:

• Need to find co-founders who share my vision

• Need to convince VCs to fund an unproven team

• Need to compete in oversaturated fintech markets

• Need to build everything from absolute zero

• Need to navigate complex regulations

• Need to hope the timing was right

BRWM path:

• Inherit 35 years of proven business model

• Get immediate access to 120 HNW clients

• Build on a solid financial foundation

• Leverage the existing regulatory framework

• Start with clear competitive advantages

The startup path had maybe a 2% chance of massive success.

(98% of startups fail…)

The BRWM path may have a 30% chance of significant success.

More importantly, the BRWM path gives me a blank canvas to experiment.

Outdated systems begging for automation.

Manual processes crying out for AI.

I could build my own startup within an established business.

I could fail fast and iterate quickly without risking everything.

Conviction

Nine months at BRWM and the contrast is staggering.

In the UK, I spent weekends staring at blank screens.

I now spend weekends building AI systems I’m desperate to ship.

In the UK, every idea felt ‘meh.’

At BRWM, every insight feels like an obvious next step.

In the UK, I was constantly second-guessing myself.

Now, I ship things without a doubt in my mind.

Everything feels natural.

The outcome feels inevitable.

That's what working on the right thing feels like.

Risk

Entrepreneurs are supposed to be risk-takers.

But the best entrepreneurs are actually masterful risk-mitigators.

They take massive risks in pursuit of massive rewards.

But they structure those risks to maximize their odds of success.

Choosing the path with the largest luck surface area is exactly that.

It's not playing it safe—you're still betting everything on yourself.

But you're giving yourself the best possible chance to win.

The framework for big decisions

When you're choosing between two paths, ask yourself:

Where am I most likely to get lucky?

What path gives me the most at-bats?

Where can I build on existing advantages instead of starting from zero?

What feels hard to others but easy to me?

Where does my natural intuition align with market opportunity?

Don't chase the shiny objects everyone else is chasing.

Find the unsexy opportunity that aligns with your unique strengths.

Build where you have conviction, not where society thinks you should.

Choose the path where luck can find you.

Takeaways

Success isn't about taking the biggest risk.

It's about taking the smartest risk.

Sometimes that looks like joining an established business instead of starting from scratch.

Sometimes it means choosing the unsexy option over the glamorous one.

Sometimes it means ignoring conventional startup wisdom.

But it always means following your conviction over external expectations.

The path with the largest luck surface area isn't always obvious.

But when you find it, you'll know.

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Thanks for reading,

— Luca

P.S. Want to work together?

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That’s it from me. See you next week, Luca 👋

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