Tips from Working a Decade in Startups
Ten years. Six startups. A few wins, a few messes, and a ton of learnings. If you're in this game, here's what I wish someone had told me early.
10 years in startups. Some wins. Some wreckage. Plenty of late nights and weird Slack threads. Still building. Still learning.
Some lessons hit late. Others I ignored until they punched me in the face. Here’s what I’d send to someone just starting out, before they dive headfirst into this chaos.
Speak up, even to a co-founder
In one of my early startups, I stayed quiet for 2 months while we built something obviously broken. I thought, "he's the founder, he must know better." He didn't. We lost a quarter. Learned to stop playing nice.
Never hire relatives
I made that mistake. She showed up late, missed deadlines, and treated the office like her weekend plan. Firing her ruined two family functions and an uncle's WhatsApp group. Never again.
Stay longer in your first jobs
There's gold in year two. That's when you see the messes people hide. That's when real compounding starts. Jumping early makes you good at Day 1, but clueless about Day 100.
Don't chase titles
You don't need to be a VP at 25. You need to be dangerous at 30.
Execution > label.
I've seen interns who ran more scope than managers with 5 years.
Learn how ESOPs actually work
I once got excited about 30,000 options. Didn't ask strike price, vesting, or if the company was ever gonna exit. They were worthless. Literally, zero. Learn the math.
HR is not your therapist
They're polite. They'll listen. But their job is to protect the company. Don't confuse HR with support. Find your people outside the org chart.
Your work is your loudest intro
I've seen engineers pulled into investor meetings just because their code changed the roadmap. You don't need to talk big when your work already shouts.
Stay humble, always
The intern who solved a scaling issue we struggled with for weeks? Yeah. That was a good ego check. If you're the smartest in the room, you've stopped learning.
Getting fired isn't failure
Had to let go of a PM once. He was excellent - just wrong timing. Two years later, he led product at a unicorn. Getting fired is not the end. Sometimes it's the start.
Avoid politics like malware
Tried playing the internal chess game once. Won the move, lost the year. Nothing beats focus. Let others climb the org ladder - you build the thing that matters.
Seriously, don't burn bridges
One guy I used to mentor now runs a fund. Another ex-colleague became a client.
It's wild how small the ecosystem is.
Stay graceful - even when exiting.
Network like anything
Most opportunities don’t come from resumes, they come from DMs, coffees, intros. Build real relationships. Follow up. Help without asking. Then ask when it matters.
Startups don’t care who you think you are. They reward clarity, consistency, and compound effort. You don’t need to be loud - you need to be useful.
If you’re in it, stay sharp. Keep learning. And leave ego at the door.
