Blog #50: When Should You Start Your Startup?
Celebrating 50 blogs of AI insight, ideas, and personal growth—this special post reflects on one of the most asked questions to me: "When should I start my startup?"
Firsly, I would like to thank all my readers, friends and family for their support. This is a milestone—my 50th blog.
When I began writing in September 2024, I wasn’t sure how long I could sustain the momentum. It’s been around eight months now, and I’m proud of myself for sticking with it.
This post isn't about AI. Today, I wanted to pause and reflect on a question I get asked often:
“When should I start my startup?”
For the past 10 months, I’ve been mentoring students at 100XEngineers on their Entrepreneurship track. I’ve had the chance to interact with incredible individuals at different stages of life. Some are second-year engineering students, while others are in their 50s, well-settled with years of corporate experience. One thing they all have in common is an insatiable hunger to learn—and most of them dream of building their own startup.
I’ve shared my learnings and personal insights with them to help them make informed decisions. In this 50th post, I want to share those insights here—shaped by my journey through two unsuccessful startups, working with some of the most impactful startups in the Indian ecosystem, and conversations with founders, friends, and family. These are my personal views—take what resonates and leave what doesn’t.
No Time to Read? Here's the Scoop
Start When You’ve Got Nothing to Lose
Your early 20s are ideal—low liabilities, no dependents, and plenty of time to fail, learn, and build. Your downside should be limited and upside should be more.
Start When You’re Financially Independent
Not when you're rich, but when your family can live comfortably without your paycheck. That could be 30, 40, or 50.
Avoid Leaving at Peak Salary Without a Safety Net
“I have 2 years of runway” plan often crashes. If things don’t go your way, you lose income and savings—then take a hit on your next job. Your first idea may most likely fail.
You Don’t Need to Start a Company to Make a Mark
You can still create wealth, purpose, and impact by working in a great team. Founding isn’t the only path.
Don’t Follow the Crowd. Know Your Path.
Your liabilities, family, priorities, and risks are yours. Don’t borrow someone else’s playbook.
The Not-So-Famous Advice on Starting Up
Let’s face it—most advice on starting a company sounds romantic.
“Follow your passion.”
“Just start.”
“You only live once.”
It sounds great on a podcast. But real life is more layered.
1. Start When You’ve Got Nothing to Lose
The best time? When you're early in your career and your downside is minimal.
You don’t have dependents. You don’t need a 7-digit salary to survive.
You can take risks that would scare a 35-year-old with EMIs and school fees.
If possible, spend a few years in a fast-paced startup. Learn what it feels like to build with constraints, navigate chaos, and ship with urgency.
You’ll either fall in love with the startup world—or know exactly why you don’t want it.
Be enterprising from your college days so you have time to experiment, fail, and learn. Read a lot. Try new things. Build that muscle.
And make sure your family isn't dependent on you to maintain their standard of living.
2. Start When You’re Financially Independent
This doesn’t mean being a millionaire.
It means your family is secure even without your monthly paycheck.
That number is different for everyone.
For some, it’s a house, some savings, and no EMIs.
For others, it’s income from investments or a spouse who provides financial stability.
Your family shouldn’t have to compromise just because you chose to take a risk. I believe it’s our core responsibility to ensure our loved ones are cared for.
If you’ve reached this stage—even in your late 30s or 40s—you’re ready.
You can go all-in without the constant pressure of, “What if I don’t make money this year?”
3. Don’t Quit When You’re at Your Peak Without a Plan
One mistake I’ve seen (and did) is quitting at the peak of one’s career.
The logic is tempting:
“I’m earning well. I’ll save a 2-year runway. I’ll build. I’ll raise funds. I’ll pay myself soon.”
Except… it rarely works that way.
Markets shift.
Products take longer.
VCs change focus.
Your first idea will most likely fail.
You lose two years of income plus your savings. And if the startup doesn’t take off?
Getting back to the same salary—or even a similar role—can be tough.
You’ve changed. The job market’s changed.
The cost isn’t just financial. It can take a toll on your physical and mental health too.
4. You Don’t Have to Be a Founder
This needs to be said more:
You don’t need to start a company to create wealth or do meaningful work.
You can join a mission-driven startup.
You can be the #3 or #10 or #50 in a rocket ship.
You can lead, grow, and make real impact—without the founder’s stress.
Founding is a path, not the path.
Many respected and successful professionals never founded a company.
If you find an exciting problem and a great team, join them. It can be deeply satisfying to contribute meaningfully to something bigger than yourself.
One word of caution: you don’t have to marry a company or an idea. Fall in love with the problem, not the logo. Love your work. Love your craft. But don’t feel pressured to idolize your workplace.
5. Carve Your Own Path
Maybe you have aging parents.
Maybe you’re a single parent.
Maybe your savings don’t match your aspirations—yet.
That’s okay.
Your journey isn’t a leaderboard.
Some people start at 22.
Some start at 45.
Some never start but still build impactful, financially strong lives.
Don’t copy. Understand your context.
Make your move when your life is ready—not just when your LinkedIn feed says so.
Final Thought
This 50th blog isn’t advice. It’s perspective.
If you’re waiting for a sign, make sure it comes from you, not your peers.
There’s no perfect timing—just your timing.
