The Things I Wish I Knew Before Joining 5 Startups

I joined five startups.

None of them paid me cash.

I'd still do some of them again.

Just not the same way.

When I first started saying yes to startup opportunities, I was desperate for experience. I needed work. I didn't think I was particularly valuable yet. I figured this was just how people broke into tech.

You take the equity.

You prove yourself.

You work hard.

Funding comes through.

Everybody wins.

Right?

Not exactly.

I Thought Experience Was Payment

The first few times, I didn't ask enough questions.

Sometimes I didn't have a contract at all.

Sometimes I had a contract that I barely understood.

I thought the experience itself justified the risk.

And to be fair, some of that experience did matter.

I learned WCAG and Section 508 accessibility standards. I learned to work with APIs that made me question my life choices. I built portfolio pieces. I gained confidence.

But I also learned that experience doesn't pay your electric bill.

Equity Isn't Cash

There's an old saying:

A bird in the hand is better than two in the bush.

Equity is a bird in the bush.

Maybe it'll become something.

Maybe it'll fly away.

Maybe funding is right around the corner.

Maybe it isn't.

The thing is, founders almost always believe funding is coming soon.

They have to.

Hope is part of the job.

Sometimes they're passionate people trying to build something meaningful.

Sometimes they genuinely believe they're six months away from success.

Sometimes they don't know.

And sometimes they're just trying to get free labor out of you.

Your job is not to borrow their optimism and treat it like certainty.

The Only One I Don't Regret

Ironically, the startup I regret the least paid me exactly the same amount as the others:

Nothing.

The difference wasn't the equity.

The difference was the mission.

It focused on helping detect Alzheimer's disease.

I've seen what that disease does to families. If my work helped move that mission forward even a little, then I can live with that choice.

I'd probably make it again.

Not because it was financially smart.

Because it aligned with my values.

Read the Damn Contract

Read the contract.

Then read it again.

Have AI read it.

Have the smartest person you know read it.

Have a lawyer read it if you can afford one.

Keep copies somewhere safe.

Because contracts are boring until they're suddenly the most important document in your life.

"We'll figure it out later" is not a contract.

Good intentions are not a contract.

Verbal promises are not a contract.

Hope is definitely not a contract.

Watch What Happens When You Ask Questions

Ask about money.

Ask what happens if funding never comes.

Ask who makes decisions.

Ask what day-to-day operations actually look like.

Ask how often the team meets.

Ask how disagreements get resolved.

Ask what success even means.

And then pay attention to how people react.

Reasonable people answer reasonable questions.

If someone loses their mind because you asked for clarity, that's information.

Use it.

Don't Burn Yourself Down

Startups will take everything you're willing to give them.

That's true whether they're paying you or not.

Take the night with your family.

Go to your friend's birthday.

Get some sleep.

Don't work twenty hours a day for months straight chasing a hypothetical payday.

Especially if you're working for free.

I'm not saying don't honor your commitments.

I'm saying don't sacrifice your entire life for a possibility.

Family and friends are real.

The startup's future may or may not be real one day.

Gratitude Matters

I don't need constant praise.

But if someone gives you hundreds of hours of skilled labor for free, don't treat them like they're disposable.

Say thank you.

Respect their time.

Remember that they have choices, too.

Eventually I learned something important:

I have a skill you don't.

I can leave.

And if you consistently treat people badly, expect people to leave.

What I'd Tell My Younger Self

I don't regret taking chances.

I regret staying after people showed me who they were.

I regret ignoring my instincts because I wanted to believe harder.

I regret assuming good intentions were enough.

If a junior developer asked me whether they should take equity instead of pay, I wouldn't automatically say no.

I'd ask:

What does the contract say?

Can you use your work in your portfolio?

What happens if funding never comes?

Can you afford to lose the time?

Do you believe in the mission?

Do these people have their shit together?

And are they showing you the kind of character you'd trust when things get hard?

Startups run on hope.

They almost have to.

Just don't let someone else's hope become your retirement plan.