I’ve built a few multi-million dollar businesses.
Not a billion-dollar one. Yet.

Lately, I’ve been obsessed with the question:
What actually gets you there?

Most teams debate:
Should we A/B test our way to the top?
Or do we need a bold, opinionated brand vision?

But I think that’s the wrong frame.

Because the best brands don’t choose between vision and iteration.
They sequence them.

The Case for Iteration

Small improvements compound. Iteration is the weapon of the disciplined.

This means running dozens of experiments — across landing pages, headlines, flows, pricing, and positioning — to discover what resonates.

When you don’t know what will work, your best bet is velocity. Try a lot of things, measure obsessively, and double down on what moves the needle.

This is the world I come from. It’s familiar. It’s powerful.

The Case for Conviction

Billion-dollar brands are built, not discovered through tests. You can’t A/B test your way into an iconic narrative.

Even Apple — the poster child for product excellence — almost never A/B tested.
The iPhone launch wasn’t optimized. It was declared.

They made a bold, opinionated bet on a future no one explicitly asked for—
but one that, once shown, felt inevitable.

It’s clear that some of the world’s biggest brands didn’t grow by running thousands of experiments. They grew by committing to a vision—and executing it with conviction.

So the question is:

If you’re building the next billion-dollar brand, how should you think about this?
Do you test your way there?
Or do you bet big and trust your taste?

Maybe the answer is both. But the order matters.

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Bold Cycles, Iterative Loops

I’ve come to believe the real path lies in the middle.
Make bold, opinionated bets. Then test the hell out of the details.

I call this framework: Bold Cycles + Iterative Loops

• Bold Cycles → Big product & brand bets (new product line, new narrative, new market)

• Iteration Loops → Rapid, constant experiments inside that bet (landing page variants, pricing models, funnel flows)

Bold cycles make the leap.
Iterative loops make it land.

If you only test, you’ll never stand out.
If you only bet big, you’ll never adapt fast enough.

Breakout brands do both—in sync.

Example: Duolingo
Their bold cycle? Turning language learning into a game.
Inside that bet: endless loops — copy, streak mechanics, push timing.
The result? A lovable owl with the retention of a slot machine.

Until next time,

Ajay