My last post — Stop Supplying. Start Owning. — was one of the most engaging posts I have published in recent weeks. One part of that talk that I did not go deep enough on was the banana analogy.

I have been using this framework in talks for some time now — most recently at the Engineering Deans Canada annual meeting in Winnipeg, and before that in a keynote at York University’s Schulich School of Business on a related but different topic: “Think like an owner”. I think this analogy deserves its own post.

So for this Sunday morning, something a little lighter. Just five banana lessons that I think apply whether you are a student figuring out your first job, a founder building a company, or an investor trying to understand where value actually lives.

Yes, I went bananas — but not in a way you might think. It all starts with a monkey.

The Setup

Jack Ma once said: if you put money and a banana in front of a monkey, the monkey takes the banana. It does not know that money can buy many bananas.

I love this analogy. On the surface, it is a simple observation about short-term versus long-term thinking. But the more I have sat with it — through three companies with well over a thousand employees across three companies, two exits, and now as an investor in over 60 companies — the more I think it contains an entire philosophy of value creation.

Here are the five lessons I have drawn from it.

Lesson 1 — Cash Is Better Than a Banana

Jobs are bananas.

People grab them because a steady salary and job security feel safe. And they are not wrong to. A banana feeds you. It is real. It matters.

But a banana feeds you once. Cash — real ownership, real equity, real stakes in what you are building — feeds you many times. The problem is not that people value jobs. The problem is that too many people never stop to ask whether there is something better in front of them.

Recognizing that alternatives exist is the first step toward creation and ownership. Most people never take that step — not because they lack ambition, but because nobody ever put the alternative clearly in front of them.

Lesson 2 — Some Bananas Are Better Than Others

Not all jobs are created equal.

Some opportunities teach you, compound your skills, put you inside exceptional teams, and give you proximity to how great companies are actually built. Others keep you comfortable but stuck — including, surprisingly, many high-paying jobs at large, slow-moving organizations.

The number of jobs created is not a useful measure of prosperity. The quality of those jobs — and what they teach, and what they lead to — is what matters.

When I was early in my career, I worked at Delrina, one of the most successful Canadian tech companies of the 1990s. The company grew from 20 people to 800 in four years when Eva and I worked there. We learned more in that rocketship environment than I could have anywhere else. That was not a banana. That was a greenhouse banana — rare, valuable, and 100% worth seeking out.

The lesson: be deliberate about which banana you grab. Not all of them are the same.

Lesson 3 — A World-Class Banana Tree Is Better Than a Banana

A banana feeds you once. A tree feeds you forever.

This is where the shift from employee thinking to founder thinking begins. One banana is a salary. A tree is equity, ownership, and compounding returns on something you built.

Ownership compounds. Wages do not.

The number of jobs created is still the wrong KPI. A single world-class company — owned, scaled, and defended — creates more durable economic value than a thousand comfortable jobs at organizations that will be restructured, acquired or hollowed out over time.

Do not just own the banana. Own the tree.

Lesson 4 — A Banana Farm Is Better Than a Tree

A tree is better than a banana. But a farm is better than a tree.

Dole, a company valued at just over $1 billion and one of the most recognizable fruit brands in the world, does not just grow bananas. It operates a vertically integrated business — owning farmland, managing logistics, controlling supply. It works with over 8,000 independent farmers who supply it. Those farmers are good at what they do. But they are suppliers.

Participation as a supplier is not enough. Ownership of the platform — the farm, the infrastructure, the system — is where the compounding really begins.

Even “the number of trees” is the wrong KPI. It is the farm that matters.

Lesson 5 — A Store Is Better Than a Farm

This is the one that tends to land hardest in a room.

Even Dole — a billion-dollar company, one of the most recognized brands in its category — is a tiny supplier to the giant retailers that actually own the customer relationship. Walmart. Costco. Amazon. These are the stores. They do not grow bananas. They sell them — at scale, with leverage, owning the customer from end to end.

The store owns the customer. The store sets the rules. The store captures the value that flows through the entire chain. Needless to say, many of these stores are an order of magnitude more valuable than Dole.

This is the lesson that I applied at Wattpad. We were not just a reading platform. We owned the direct relationship with five million writers and one hundred million readers, with virtually no external dependencies. That end-to-end ownership is what made us defensible.

Amazon Kindle tried to kill us — not once, but multiple times. They launched product after product specifically designed to compete with Wattpad. Not only did we win every battle, we won the war. A clean sweep. It is rare for a company our size to take on Amazon Kindle directly and come out on top. Owning the full chain — the writers, the readers, and the relationship between them — is what made that possible. I will save the full story for another post.

True prosperity means owning the whole chain — from innovation to commercialization, from suppliers to customers. The number one KPI is ownership. Jobs follow capital, innovation, and commercialization. Not the other way around.

Why This Matters Beyond Business

I have shared this framework in many different rooms — with founders, with students, with engineering deans — and it lands every time. I think it is because the banana lessons are not really about business. They apply broadly to how we think about our lives.

Yes, the framework is useful in a business context. And yes, it is useful in an investment context. But it also applies to personal decisions, career choices, relationships, and how we spend our time. Are you grabbing the banana in front of you because it is comfortable and familiar? Or are you asking what the tree looks like? What the farm looks like? Who owns the store?

The mental model you build early about what success looks like shapes every decision that follows. Most people never stop to interrogate it.

Do not just grab the banana. Ask yourself what the tree looks like. Then ask what the farm looks like. Then ask who owns the store.

That is where the real value lives — in business, in investing, and in life.

If you missed the post this is a follow-up to, you can read Stop Supplying. Start Owning. here: [Link]