In 1974, after the “Rumble in the Jungle,” Muhammad Ali stood on the summit of boxing history.
He’d dethroned George Foreman, a younger, more powerful fighter - and reclaimed the heavyweight crown.
Picture Mount Everest – he'd reached the peak.
But unlike the wise climbers who turn back when conditions deteriorate, Ali kept climbing into thin air.
The result?
A decade of diminishing returns.
Slurred speech. Trembling hands.
A legend who stayed too long at the party.
In business, we glorify grit.
“Never quit,” they say.
But Annie Duke's brilliant book “Quit” argues the opposite: knowing when to walk away is a superpower.
Think of poker pros.
They fold more than half of their hands.
Amateurs cling on, praying for miracles—and lose their shirts.
Pros quit early, conserve chips, and wait for the right hand.
Founders often do the opposite.
They keep climbing the Everest of failing ventures, ignoring the changing weather, sunk costs, or legal quicksand beneath their feet.
The math stopped working six months ago, but they keep raising rounds, hiring staff, and telling themselves the next quarter will turn things around.
This is the sunk cost fallacy with a legal twist – every day you persist, you're not just losing money.
You're accruing potential liabilities, contractual obligations, and exposure that multiplies like compound interest in reverse.
The law rewards the decisive.
Drag your feet, and your sunk costs may turn into liabilities.
Take Stewart Butterfield.
His startup “Glitch” was well-funded and growing. Most founders would have doubled down.
He quit.
Rebuilt.
Created Slack, the workplace messaging app.
Sold it for $27.7 billion.
He didn’t fail.
He folded early and played a better hand.
Knowing when to quit isn’t a weakness. It’s a strategy.
The difference between Ali’s twilight years and Slack’s meteoric rise is one decision: the courage to walk away while ahead.
Ask 3 Questions Before You Persist
1. Expected Value Test: If you could start fresh today with your current knowledge, would you choose this path? Not "should I continue" – would you begin this journey?
2. Kill Criteria Check: When you started, what were your metrics for success? Have you moved the goalposts to avoid confronting failure?
3. The Philips Principle: Is your identity welded to a dying market? Philips was a lightbulb company. It quit that identity and became a €20 billion healthcare leader. Sears was a retail. It died defending that identity.
🔥 Bottom line:
• Quitting protects capital—financial, emotional, and legal.
• Quitting frees you to chase better opportunities.
• Quitting, done well, is leadership.
Ali should have quit after Zaire.
He didn't, and the cost was measured in neurons and dignity.
As founders, the bravest decision may not be to fight on.
It may be to fold—before the heaviest punches land.
Ever quit something early—and thank yourself later?
Hit “reply” and share your experience - I’d love to hear it.
To your continued success,
Kamal
