The Startup Dream (And Why It's So Seductive)

If you're job searching right now, you've probably seen them: startup job postings that promise something different. Not just a salary, but equity. Not just a role, but a mission. Not just colleagues, but a "family" building something that could change the world.

It's seductive. I understand the appeal. I've started multiple businesses myself, and there's nothing quite like the energy of building something from nothing.

But I've also seen the other side. The startups that failed. The promises that never materialized. The people who gave years of their lives to visions that evaporated.

This series is for job seekers considering startup opportunities—especially those who haven't worked in the startup world before. Not to scare you off. But to help you go in with your eyes open.

The Magic Is Real (Sort Of)

Let me start by acknowledging what makes startups genuinely appealing. This isn't just marketing hype—there are real things that draw smart people to early-stage companies.

The creativity. At a startup, you're not maintaining—you're building. Every day involves problems nobody has solved yet. There's no playbook, so you get to write one. If you're the type who gets bored doing the same thing twice, this is intoxicating.

The collaboration. Small teams mean everyone matters. You're not a cog in a machine. Your ideas get heard. Your work has visible impact. The distance between "I have a thought" and "we're doing it" can be remarkably short.

The mission. Startups often organize around a clear purpose: we're going to solve this problem, disrupt this industry, help these people. Whether or not they succeed, there's a sense of meaning that can be hard to find in large organizations optimizing for quarterly earnings.

The potential upside. And yes—the equity. The lottery ticket. The chance that this thing takes off and your 0.5% becomes life-changing money. It happens. We've all seen the stories.

I'm not dismissing any of this. These things are real, and they matter. If you've only ever worked at large companies, a startup can feel like a revelation. Finally, work that doesn't feel like work.

But here's where we need to get honest.

The Hollywood Analogy

I think about startups the same way I think about Hollywood.

Every year, thousands of young people move to Los Angeles, chasing the dream of stardom. They've seen the movies. They know the success stories. They believe—genuinely believe—that talent and hard work will get them there.

Some of them are right. Most of them aren't. The vast majority will spend years waiting tables, going to auditions, getting close but never quite making it. They'll eventually go home, or find adjacent careers, or keep chasing the dream long past the point of reason.

We don't tell these aspiring actors they're stupid. The dream is real. Some people do make it. But we also don't pretend the odds are good.

The startup world works the same way.

Every Instagram acquisition ($1 billion, 13 employees) spawns a thousand startups hoping to be next. Every Uber, every Airbnb, every startup unicorn creates a wave of believers. And with every wave, the odds get worse, because now there are more people chasing the same dream.

This isn't pessimism. It's just math.

The Numbers Nobody Talks About

Let me share some statistics that startup job postings don't mention:

I'm not saying this to crush your dreams. I'm saying it because these numbers are important context that job seekers rarely get.

When you're evaluating a startup opportunity, you need to understand that you're not evaluating a sure thing with upside potential. You're evaluating a long shot that might pay off spectacularly but probably won't pay off at all.

The Mental Contagion

Here's what fascinates me: we know these numbers. They're not secret. And yet people keep taking startup jobs as if the odds don't apply to them.

There's a kind of mental contagion in startup culture. Success stories spread. Failure stories don't. So we develop a wildly distorted sense of what's likely.

It's the lottery effect. Rational people who would never play the lottery suddenly become believers when the prize is a billion-dollar exit instead of a Powerball jackpot. The mechanism is the same—survivorship bias, availability heuristic, the seductive power of "why not me?"

And it's not just job seekers. Founders have it worse. The founders I know aren't delusional—they're usually smart, driven, capable people. But they've absorbed a culture that celebrates swing-for-the-fences bets and treats failure as a badge of honor rather than a cautionary tale.

What This Means for Job Seekers

So what do you do with this information?

First, understand that nothing I've said means you shouldn't work at a startup. Startups can be wonderful places to work if you go in with realistic expectations.

The creativity is real. The collaboration is real. The mission, the energy, the learning—all real. You can have incredible experiences at startups that would be impossible at larger companies.

But you have to know what you're actually signing up for.

You're signing up for uncertainty. The company might not exist in two years. Your job might not exist in six months. The product might pivot, the funding might fall through, the founders might have a falling out. Stability is not part of the package.

You're signing up for below-market compensation (usually). Startups rarely pay market rate salaries. The equity is supposed to make up for it. But as we discussed, the equity is probably worthless. So in expected value terms, you're probably taking a pay cut.

You're signing up to bet on other people's vision. When you join a startup, you're not pursuing your own entrepreneurial dream—you're supporting someone else's. You're trusting their judgment, their execution, their ability to navigate the thousand things that could go wrong.

None of this is bad. It's just reality. And in Part 2, we'll talk about how to read startup job postings and separate the legitimate opportunities from the ones that are designed to exploit your enthusiasm.

The Key Question

Before I close, I want to leave you with the question I think every job seeker should ask before taking a startup role:

If the answer is yes—because of the learning, the mission, the people, the experience—then it might be a great opportunity.

If the answer is no—if you're only considering it because of the equity lottery ticket—then you should probably look elsewhere.

Startups can be incredible places to work. But they're only incredible if you know what you're getting into.

More on that in Part 2.

Thinking about starting your own thing instead of joining someone else's? Our Build Something series explores when entrepreneurship makes sense—and when it doesn't.

Need help reading job postings in general? Check out How to Read a Job Ad for the fundamentals.