You Can't "Win" in Tech Unless You Cheat

PayPal started by paying people to sign up. Their viral growth came from essentially bribing users with $10 to join and $10 for each referral. That’s not innovation — it’s buying market share with venture capital.

Uber didn’t disrupt transportation — they ignored taxi regulations their competitors had to follow. Their “innovation” was breaking laws in so many jurisdictions simultaneously that regulators couldn’t keep up.

Airbnb built its empire by helping people violate lease agreements and local housing regulations. They created a marketplace for illegal sublets and called it revolutionary. And then gentrified and destroyed neighborhoods and tore apart communities as a side hustle. 

Facebook harvested user data aggressively, violated privacy expectations repeatedly, and apologized later — always after the profits were banked. Every scandal followed the same pattern: break trust, capture value, apologize, repeat. To the detriment of millions. 

For years, Amazon operated at a loss, using investor capital to undercut retail competitors who needed to make money. They turned predatory pricing into a business model and called it customer obsession.

Tesla announces features before they exist, takes pre-orders for products barely in development, uses customer deposits as interest-free loans and has still never delivered the Roadster. They’ve turned vaporware into a financing strategy.

See the pattern? The biggest tech successes of our era didn’t win through superior technology or innovation. They won by:

• Breaking existing regulations
• Misusing user trust
• Deploying capital as a weapon
• Converting violations into venture funding
• Moving fast and breaking things (and laws) (and societies) (and people)

Every unicorn has a graveyard of competitors who “played by the rules” and lost.

Now these empires built on deception are showing the cracks in their foundations. Their stock prices cannot grow forever. Their users' trust has evaporated. Their products are in decline. Their employees are revolting, protesting and leaking as the bankruptcy becomes impossible to ignore. The world they created through shortcuts and exploitation is unstable. Sooner or later, it will implode under its own weight.

But that’s the old game where “winning” meant IPOs, unicorn status, and TechCrunch headlines.

Let’s talk about the new game.

While Silicon Valley plays Monopoly, a parallel universe is growing in the shadows. Developers building open-source tools that generate $50k monthly. Newsletter writers earning more than startup CEOs. Product creators who never touch venture capital but build sustainable wealth.

These players rewrite victory conditions. They don't scale through rule-breaking – they scale through value creation. Their metrics aren't vanity numbers, they're profit margins. Their exit strategy isn't acquisition, it's perpetual ownership.

The new breed wins differently:

• They build in public, not behind NDAs
• They monetize directly, not through surveillance
• They grow organically, not through growth hacks
• They own their destiny, not their investors

The old tech playbook required massive capital, regulatory arbitrage, and moral flexibility. The new one demands creativity, independence, and alignment with users.

Which game will you play?

The billion-dollar lottery where the house always wins, or the infinite game where you set the rules?

Here’s what Silicon Valley won’t tell you: true innovation doesn’t come from breaking the rules in a zero-sum game — it comes from breaking free of the zero-sum game entirely.

Build something small. Embrace decentralization or own it completely without the influence and pressure of entrenched power. Scale thoughtfully.

That’s how you win without cheating.

It's how we all win.