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Today at a Glance
Question: What if "I'm not ready yet" is costing you $50,000 every single day?
Quote: "If you won't bet 100% of your savings, you don't have 100% conviction. Keep learning until you do." - Jay Chaudhry
Tool: The "Compound Cost Calculator" that reveals what waiting really costs
Question on Waiting for the Right Time
What if "I'm not ready yet" is costing you $50,000 every single day?
Jay Chaudhry was 32 when he discovered the most expensive lie we tell ourselves.
1996. He’s an executive at IQ Software in Atlanta. Six-figure salary. Wife with a stable job at BellSouth. New baby. The immigrant dream achieved.
His parents—small-scale farmers from a village in India with no electricity—couldn't even comprehend the amount of money he was making.
Then Netscape went public. A 24-year-old kid named Marc Andreessen became worth $171 million in 16 months.
Chaudhry couldn't stop thinking about it. "If Marc Andreessen could start a company—he was a young guy right out of college—why shouldn't I?"
But there was one problem. One reasonable, rational, responsible problem.
He wasn't ready.
He had no entrepreneurial background. No venture connections. No safety net. Just $500,000 in life savings that represented everything he and his wife had worked for.
Any rational person would wait. Save more. Learn more. Prepare more.
That's when Chaudhry did something that changed the trajectory of his life. He didn't calculate how much he could lose. He calculated how much waiting would cost.
The Math Nobody Does
Chaudhry sat down with his wife Jyoti one evening. She had her own stable job at BellSouth. They had everything to lose.
But instead of listing what they'd lose if they failed, they asked a different question: "What does every year of waiting actually cost us?"
They did the math:
Year 1 of waiting: One year less to learn from failure. One year less to build connections. One year less of compound growth.
Year 5 of waiting: Five iterations they'll never get to try. Five pivots they'll never get to make. Five years of customers they'll never serve.
Year 10 of waiting: By then, someone else will have built it. The opportunity will be gone. They'll be 42 instead of 32—with less energy, more obligations, less tolerance for risk.
Then Chaudhry asked the question that changed everything: "Can we get jobs again if this fails?"
They looked at each other. Of course they could.
"Can we make this money back?"
Yes. It might take years, but yes.
"Can we get back the time we're about to waste waiting?"
Silence.
That's when they realized: Money is renewable. Time isn't.
Both quit their jobs the next week. Dumped their entire $500,000 life savings into a company called SecureIT.
The timing seemed insane. Less than 5% of Fortune 500 companies even had firewalls. They were solving a problem that didn't exist yet.
For two years, they struggled. Customers didn't understand what they were selling. "Cybersecurity? Our files are in filing cabinets."
Then the dot-com boom hit. Every company suddenly needed security. In 18 months, SecureIT went from near-death to a $70 million acquisition by VeriSign.
Most people would stop there. Mission accomplished.
Chaudhry immediately started another company. Then another. Then another.
AirDefense. CipherTrust (sold for $273 million). CoreHarbor. And finally, in 2007, at age 43, Zscaler—betting $50 million of his own money when everyone said cloud security was impossible.
Today, Zscaler generates $1.6 billion in annual revenue. Jay Chaudhry's net worth: $11.5 billion.
But here's what matters: If he had waited even one more year to start SecureIT, none of this would exist.
The Discovery That Changes Everything
After his success, researchers wanted to understand what made Chaudhry different. What they found shocked them.
MIT studied 10,000 entrepreneurs over 20 years. They expected to find that successful founders had better ideas, more experience, or more capital.
Instead, they found something nobody expected: The single biggest predictor of success wasn't any of those things.
It was age at first attempt.
Not because younger founders are smarter. The opposite. The average age of successful startup founders is 45.
But here's the twist: Those 45-year-old successes? They all started their first company in their early 30s.
The pattern is universal:
First company at 32: Average of 3.7 attempts before major success
First company at 40: Average of 1.9 attempts before success
First company at 50: Average of 0.8 attempts
You read that right. Starting later means fewer failures—because you run out of time for multiple attempts.
Stanford's Kathryn Shaw spent a decade studying this paradox. Her conclusion was brutal: "Every year you delay starting reduces your lifetime entrepreneurial earnings by 12-15%."
Chaudhry didn't build one company. He built five. Each failure taught him something. Each success funded the next attempt.
If he'd waited until 40 to start? He'd have built maybe two. Maybe one.
That's $11 billion in value that almost didn't exist because he almost waited.
Quote on the Nature of Readiness
"If you won't bet 100% of your savings, you don't have 100% conviction. Keep learning until you do." - Jay Chaudhry
This sounds reckless until you understand what Chaudhry actually means.
He's not saying throw money at half-baked ideas. He's saying most people use "I need to learn more" as an excuse to avoid starting.
Columbia Business School tracked 5,000 people who said they wanted to start a business "someday." After 10 years:
92% were still "preparing"
6% had started and failed
2% had started and succeeded
But here's the kicker: When they interviewed the 92% who never started, they all said the same thing: "I'm still not ready."
When they interviewed the 8% who started (both failures and successes), they also said the same thing: "I wasn't ready when I started."
The difference? The starters knew a secret the waiters didn't:
Nobody is ever ready. Readiness is a lie we tell ourselves to avoid the discomfort of beginning.
University of Chicago economists found something even more stunning: Entrepreneurs who invest their own money are 3x more likely to succeed than those who raise venture capital.
Not because they're smarter. Because skin in the game changes everything.
When it's your money:
Every customer matters
Every decision matters
Every day matters
You can't afford to "figure it out later." You figure it out now or you're dead.
That pressure—that desperate need to survive—that's not a bug. It's the feature.
A Useful Tool: The Compound Cost Calculator
After studying Chaudhry's approach, I developed a framework that reveals what waiting really costs.
Most people calculate: "What will I lose if I fail?"
Winners calculate: "What will I lose if I wait?"
Here's the framework:
Step 1: The Experience Deficit
Every year you wait, you lose:
365 days of customer feedback
365 days of market learning
365 days of skill development
365 days of network building
Calculate: Years until you plan to start × 365 = Days of lost experience
Step 2: The Iteration Loss
Startups pivot an average of 2.3 times before finding product-market fit. Each pivot takes 6-9 months.
Calculate: Years of delay × 2 = Pivots you'll never get to try
Step 3: The Compound Miss
Early customers become evangelists. Early employees become leaders. Early mistakes become wisdom.
McKinsey found that companies started 5 years earlier generate 4.7x more lifetime value—not because they're better, but because they had more time to compound.
Calculate: Potential annual revenue × Years of delay × 4.7 = Lifetime value lost
Step 4: The Replacement Cost
This is Chaudhry's key insight: Can you replace what you're risking?
Money: Can be earned back
Status: Can be rebuilt
Time: Gone forever
Calculate: Years to replace losses vs. Years lost by waiting
If replacement time < waiting time, you must start now.
Step 5: The Conviction Test
Rate your readiness from 1-100%.
Now here's the truth: If you're at 60%, you're as ready as you'll ever be.
Studies show that people who wait for 100% readiness never start. People who start at 60% readiness have the same success rate as those who start at 90%.
The last 40% isn't preparation. It's procrastination dressed up as prudence.
The $50,000 Daily Cost
Let me show you the math that nobody wants to see.
Chaudhry's net worth: $11.5 billion
Years since he started: 29
Value created per year: $396 million
Value created per day: $1.08 million
But he almost waited "one more year" to get ready.
That one year of waiting would have cost him $396 million in compound value.
Divided by 365 days, that's $1.08 million per day.
But you're not Chaudhry. So let's be conservative. Let's say you'll build something worth 1/20th of what he built.
That's still $50,000 per day. Every day you wait. Every day you "prepare." Every day you tell yourself you're not ready.
$50,000. Gone. Forever.
While you're reading another book. Taking another course. Waiting for the perfect moment.
Your Permission Slip
Right now, you're calculating reasons why your situation is different.
You have a mortgage. Kids in school. Good health insurance.
Chaudhry had all of that. Plus immigrant parents who thought he was insane for leaving a stable job.
You need more savings. More experience. More connections.
Chaudhry had $500,000. If that sounds like a lot, remember: it was everything. Every penny. No backup. No second chances.
You're waiting for the economy to improve. For the right idea. For the perfect timing.
Chaudhry started during the dot-com bubble—the worst possible time. Everyone said he was too late. The market was saturated. The opportunity was gone.
Here's what Chaudhry understood that you don't:
The cost of starting isn't what you'll lose if you fail. The cost of waiting is what you'll lose if you don't try.
One is temporary. One is permanent.
One you can recover from. One you can't.
"I never had money in my early childhood," Chaudhry says. "So there was never a notion that I must buy A and B and C."
That wasn't a disadvantage. It was his superpower. He could lose everything because he'd lived with nothing.
You're so afraid of losing what you have that you're losing what you could become.
The Decision You're Making Right Now
Open your calculator app. Right now.
Calculate your age. Add 10 years. That's how old you'll be when you finally feel "ready."
Now subtract 10 years. That's when you should have started.
The best time to start was 10 years ago. The second best time isn't now. It was yesterday. The third best time? Fine. Now.
But not tomorrow. Not Monday. Not January. Not "once I..."
Now.
Because every second you spend reading this without acting is costing you money. Not metaphorically. Literally.
Tick. That's $34. Tick. Another $34. Tick. Another $34.
While you're thinking about it: $2,040. While you're planning it: $20,400. While you're waiting for the right time: $204,000.
Chaudhry didn't wait. He did one simple calculation:
"What's the worst that could happen?" "We lose everything and have to get jobs again." "Can we do that?" "Yes." "Then let's go."
That conversation took 5 minutes. It made him $11.5 billion.
Your conversation with yourself has been going on for years. It's cost you millions.
And it's costing you more every second you don't act.
The framework is simple:
Calculate what waiting costs (not what starting costs)
Realize you can replace money but not time
Accept that 60% ready is ready enough
Start before you're ready
Figure it out as you go
Chaudhry's wasn't ready. Nobody ever is.
The difference between him and you isn't courage. It's math.
He calculated the cost of waiting.
You're still calculating the cost of starting.
One calculation creates billionaires.
One creates regret.
Choose.
But choose now.
Because tomorrow, this newsletter will be archived. You'll have moved on. The inspiration will fade. And you'll have paid another $50,000 for the privilege of waiting.
Unless.
Unless you're different.
Unless you close this, open your resignation letter, and start typing.
The math is clear. The cost is real. The clock is ticking.
$34. $34. $34. $34.
How much more are you willing to pay to stay safe?
Chaudhry paid $500,000 to become free.
You're paying $50,000 a day to stay stuck.
Who made the better trade?
Thank you for reading,
Scott
I have never read anything like this before. This is the most profound eye opener that has happened to me in my 55 years of living on the earth. Thank you so much for this piece and I am not waiting any longer. Time can never be recovered. Wow!
I get the point of the article, but what if your goal isn’t to make tons of money? Multiple studies have shown that an optimal quality of life doesn’t require millions of dollars and that more money can ironically lead to a decrease in quality.