In the last piece, I asked a question worth sitting with: how many real options do you actually have right now?
Not hypothetically. Right now. If an opportunity appeared tomorrow, could you move on it? If you needed to walk away from something that was draining you, could you?
For most people, the honest answer is: not as many as I’d like.
But that’s not a character flaw. It’s a structural problem. And structural problems require structural solutions.
The OLE Wealth Flywheel is mine.
OLE stands for Opportunity, Leverage, and Equity.
On the surface, it’s a wealth-building framework.
But underneath, it’s something more specific.
A system for manufacturing optionality deliberately, one cycle at a time. Each rotation through the flywheel doesn’t just generate income or assets. It expands your capacity to act. It makes the next opportunity easier to see, easier to pursue, and easier to convert into something that lasts.
Here’s how each stage works, and why it matters for the kind of freedom we’re actually building toward.
Stage 1 — Opportunity: The Asymmetric Filter
Not every opportunity deserves your attention. Most don’t.
But here’s something I’ve observed with many frameworks: they tell you to filter for good opportunities without telling you what “good” actually means. So people default to safe. Familiar. Predictable. But predictable rarely compounds.
The optionality lens gives you a sharper filter: you’re looking for asymmetric opportunities. Situations where the downside is small and defined, but the upside is large and open-ended.
Taleb illustrates this with a simple example: sending a cold email to someone you admire costs you ten minutes. The worst case is silence. The best case is a relationship that changes your trajectory.
That’s an asymmetric play. The risk is capped. The reward is not.
Your business opportunities work the same way. Before committing to anything significant, ask two questions:
What’s the worst realistic outcome if this doesn’t work? And can I absorb it?
What’s the best realistic outcome if this does work? And is it meaningfully bigger than the cost?
If the downside is survivable and the upside is transformative, you’re looking at an OLE-ready opportunity. If the downside is catastrophic and the upside is incremental, you’re looking at negative optionality, and you probably should walk away regardless of how attractive it looks on the surface.
The Opportunity stage is your first line of defence against trades that appear to be progressing but quietly erode your positioning.
Stage 2 — Leverage: Dismantling the Obligation Trap
Here’s the uncomfortable truth about most of our incomes: it comes with a hidden obligation.
Show up, get paid.
Stop showing up; it stops.
That’s not an asset. That’s a dependency.
And dependencies are the enemy of optionality, because they eliminate your right to choose. When your income requires your presence, your time is no longer yours. Every hour is spoken for before you decide how to spend it.
Leverage is how you break that ceiling.
Naval Ravikant, whose thinking on this I’ve found consistently useful, identifies four primary types of leverage: people, capital, code, and media.
Each one lets you generate more output per unit of input. Each one shifts you from obligated to positioned.
- People leverage means your results don’t stop when you do. A team, partners, or well-placed contractors extend your capacity beyond what your hours allow.
- Capital leverage means your money is working alongside you, or even instead of you. Investments, financing, and other people’s capital deployed intelligently.
- Code and systems leverage means you build something once, and it runs repeatedly. A productised service. An automated process. A tool that delivers value without you rebuilding it each time.
- Media and distribution leverage means your ideas travel farther than your presence does. A newsletter, a content library, and a community are all assets that compound in reach over time.
The goal isn’t to use all four simultaneously from day one. It’s to ask, at every stage of building something: where is my time most obligated, and what would break that obligation?
Every answer to that question is a decision about leverage. And every leverage decision moves you closer to a life where your output isn’t capped by your hours.
Stage 3 — Equity: Banking Future Options
I think this is the largest divide between being self-employed and building a business.
See, many self-employed people build income. They chase the next contract. They solve problems for clients and move on. And there’s nothing wrong with any of that until you realise that income disappears the moment you stop generating it, and you’re back to zero.
Equity is different. Equity is anything that continues to hold or create value even when you’re not actively working on it. It’s the asset that outlasts the effort. And a business built with the right teams and systems is such an asset.
But through the lens of optionality, equity isn’t just wealth. It’s stored optionality. Every piece of equity you build is a future option you don’t have to earn again from scratch.
Think about what that actually means in practice:
A business with documented systems and recurring clients doesn’t just generate income. It gives you the option to step back, bring in a manager, or sell.
A content library doesn’t just build your brand. It gives you distribution you don’t have to rebuild every time you have something to say.
An audience that trusts you doesn’t just support your current work. It gives you a launchpad for the next thing, whatever that turns out to be.
The questions worth asking at this stage aren’t just “is this profitable?”
They’re: if I stopped working on this for six months, what would still exist? Is this building my balance sheet or someone else’s? Can it be sold, licensed, or transferred?
The entrepreneurs who stay busy and the entrepreneurs who build wealth are often working just as hard. The difference is that one of them is converting effort into equity, and the other isn’t.
The Critical Loop: Harvest and Redeploy
Here’s where the flywheel becomes a flywheel.
Most people either never harvest, they keep reinvesting everything and burn out, definitely guilty of this one at times, or they harvest too much, cash out, and stop building.
The art is in the balance: knowing when to take value out of the cycle and how to allocate it deliberately.
Harvesting isn’t just profit-taking. It’s extracting every form of value the cycle produced, cash, yes, but also knowledge, relationships, systems, and proof. All of it feeds the next rotation.
Redeploying is where optionality management happens. Every time you harvest, you’re making three simultaneous decisions:
How much goes to lifestyle? This is optionality in use, enjoying the freedom you’ve built, now, not someday. This matters. A wealth-building system that never pays out isn’t freedom, it’s just a different kind of trap.
How much goes to protection? Emergency fund, insurance, stability. This is optionality preserved, ensuring that a bad month or a bad year doesn’t force your hand and collapse your options overnight.
How much goes back into the flywheel? New opportunities, better leverage infrastructure, deeper equity positions. This is optionality expanded, using what you’ve built to access better plays in the next cycle.
The exact percentages matter less than having a deliberate system for making this decision every single time. Because without a system, the default is to spend it, and the flywheel slows.
What the Compounding Actually Looks Like
Here’s something I’ve observed over time.
The second cycle is easier than the first. Or as I’ve once heard, the first million is always the hardest, but once you get there, getting to ten becomes easier.
Not because you got lucky. Because you have more capital, better judgment, stronger systems, and a clearer sense of what works. The fifth cycle is easier than the second. The tenth cycle is where the compounding becomes almost unfair.
Every rotation through the flywheel leaves behind:
- More financial capital to deploy
- More knowledge about what asymmetric opportunities actually look like
- More leverage infrastructure that runs without you
- More equity compounding quietly in the background
- More relationships that open doors you couldn’t see before
That’s not just wealth building. That’s optionality stacking. And it accelerates.
The goal was never to hit a number. It was to reach the point where your options expand faster than your obligations. To reach a point where each cycle gives you more freedom to act, more capacity to contribute, and more ability to live the life you actually designed.
That’s what the flywheel is for.