15 Years, No IPO: Startup Red Flag or Quiet Power Move?

Why some startups stay private forever—and what it means for your equity, your upside, and your job offer

A $400K offer that might be worth $0

You get a job offer from a 200-person startup.
Founded 15 years ago.
$100K salary, $400K in equity.

But there’s a catch: your shares only vest at IPO or acquisition.
And… there's no IPO in sight.

You pause.
Is this a dream job—or a decade-old lottery ticket?

That’s exactly what one engineer asked on Reddit—and thousands replied.

Some said it’s normal. Others called it predatory.
But behind the debate is a deeper question most founders and candidates never ask:

What happens when a startup never exits?

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Let’s unpack why some companies stay private forever—and how to protect yourself if you’re offered “equity” that may never turn into cash.

Because in a world where exits can take 15–20 years, what really matters isn’t just the size of your offer—it’s how (and when) that equity becomes real.

And if you're not careful, you could be working for free.

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🚧 First, Let’s Debunk the Word “Startup”

After 15 years and 200 employees, a company is no longer a startup in the classic sense.

Startups, by definition, are temporary organizations searching for repeatable and scalable business models. At some point, if they succeed, they stop being startups and become… businesses.

So if you see a company still branding itself as a “startup” 10+ years in, it’s usually for one of three reasons:

1. They still have venture capital on the cap table and aren’t profitable

2. They want to preserve startup “culture” for talent recruitment

3. They use the label as cover for offering below-market salaries in exchange for “future upside”

Let’s be clear: calling a 15-year-old company a startup doesn’t automatically mean it’s a scam. But it does mean you should look harder at how and why they're still positioning that way.

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🧾 Not All Exits Are IPOs

One of the most common misconceptions in tech is that IPO = success.

In reality, the majority of startups never IPO. Most end in one of three ways:

• They get acquired

• They become profitable and stay private

• They go bust

The IPO route is rare—and often overrated. Going public is expensive, exhausting, and turns your CEO into a full-time compliance manager. Some founders actively avoid it.

And in today’s market, it’s not even a good bet. The median time to IPO is now 11–13 years, but that number is trending longer, not shorter. Many successful companies (Stripe, Epic Games, SpaceX, Cargill) have stayed private for over a decade—some forever.

So if a company hasn’t IPO’d after 15 years, it might just mean they’re stable, profitable, and not interested in Wall Street. That’s not a red flag. That’s a choice.

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💸 But Watch the Equity Terms—Closely

Here’s where things get sketchy.

The Reddit post mentions a compensation package with equity that vests only upon a “liquidity event” (IPO or acquisition). That’s not the same as standard time-based vesting (e.g. 4 years with a 1-year cliff).

This kind of equity structure is a red flag for a few reasons:

1. No time-based vesting means you could stay 5 years and still walk away with nothing if there’s no exit.

2. No secondary market access means you can’t sell your shares to anyone else.

3. Vesting on event only gives founders and leadership total control—and incentives to delay exits until they’ve squeezed more value from the team.

As one Redditor put it:

“This lets them act like they compensate people with equity but then never actually pay... They’ll fire you right before an exit and reclaim your unvested shares.”

In short: this structure shifts all the risk onto the employee and none onto the company.

If you're offered equity in a company this old, demand:

• A clear vesting schedule

• Transparency on how your shares are priced

• Access to a cap table or estimate of dilution

• Information on past exits or employee liquidity

Otherwise, you're signing up for a lottery ticket that may never be drawn.

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🤔 So Is 15 Years Without an Exit a Red Flag?

Not inherently. But context matters.

Ask these 5 questions:

1. Is the company profitable?
   If yes, staying private may be a strength—not a weakness.

2. Have investors been waiting a decade for liquidity?
   That pressure can boil over into layoffs, pivots, or forced exits.

3. Is this equity structure common for other employees?
   If nobody else has cashed out in 10 years, be skeptical.

4. Are you being underpaid in cash?
   A $100K salary in tech, with no bonus and illiquid equity, might not cut it—especially at a mid-level role.

5. Do they plan to IPO or sell?
   If there’s no exit in sight and no secondary market access, your equity is just paper.

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🧠 The Bigger Picture: Liquidity ≠ Legitimacy

Founders who resist IPOs aren’t necessarily hiding anything. They may want control. They may hate the quarterly grind. Or they may simply be building a long-term, cash-flowing company that doesn't need public markets.

But when they pair that with below-market salaries and ambiguous equity terms—that’s when your red flag should wave.

As an employee, you’re trading time and skill for future value. Make sure that value is real, fair, and achievable—not just a story on a slide deck.

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🔍 TL;DR for Candidates

• A 15-year-old “startup” is probably a private business. That’s fine.

• Lack of IPO ≠ failure. But unclear exit plan + no liquidity + low pay = risk.

• Vesting only on liquidity event? Push back or walk away.

• Good businesses don’t need to IPO. But good employers don’t hide the terms.

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Final Thought
In 2025, liquidity is the exception, not the rule. If you’re taking equity in lieu of salary, make sure you’re not betting blind.

Because in a world where exits take 15–20 years, what matters isn’t when a company goes public—it’s whether you’ll still be around when (or if) it does.

And whether you’ll have anything left to show for it.

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❓FAQs: Startups Without IPOs, Equity Vesting, and Long-Term Private Companies

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Is it a red flag if a startup hasn’t IPO’d after 15 years?
Not necessarily. Many companies take 10–15+ years to go public—some never do. Lack of an IPO isn’t a red flag on its own. However, it can be a concern if paired with unclear business performance, low salaries, or poor equity structures. The bigger question is: is the company growing, profitable, and transparent about future plans?

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How long does it usually take for a startup to IPO?
The median time to IPO is 11–13 years. In sectors like SaaS and deep tech, it can take even longer. Companies like Stripe, SpaceX, and Epic Games have remained private well beyond that—some for 15+ years.

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What happens if I join a startup and it never goes public?
If your equity only vests on a liquidity event (IPO or acquisition), and no such event happens, you may never receive the value of that equity. That’s why it’s critical to clarify the vesting terms, exit plans, and whether there’s any access to secondary markets or cash-based bonuses.

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Is equity that vests only at IPO a red flag?
Yes. Equity that only vests upon an IPO or acquisition can be a major red flag. This structure puts all the risk on you and gives the company power to delay or cancel your upside. Standard vesting is time-based (e.g. 4 years with a 1-year cliff). Anything else deserves scrutiny.

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What’s the difference between a startup and a private company?
A startup is typically an early-stage company still searching for product-market fit or scalable growth. Once a company has hundreds of employees, steady revenue, and a mature product, it’s usually considered a private company—even if it still calls itself a “startup.”

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Can I sell my startup equity before an IPO?
Only if the company allows it. Some private companies offer secondary markets or allow employees to sell shares to approved investors. But in many cases, private company equity is illiquid—meaning you can’t sell it or access its value until a formal liquidity event.

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What questions should I ask before accepting startup equity?

• What is the vesting schedule?

• Is there time-based vesting or only event-based?

• How is equity valued today?

• What is the likelihood or timeline of an IPO or acquisition?

• Are secondary transactions allowed?

• How has equity been treated for past employees?

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Are IPOs the only way startup employees can make money?
No. Some companies allow secondary share sales or employee liquidity rounds. Others offer annual cash bonuses or profit-sharing. IPOs and acquisitions are the most publicized routes, but they’re not the only path to earning real value from equity.

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Why do some companies avoid going public?
Companies may avoid IPOs to retain control, minimize regulatory burden, and avoid quarterly earnings pressure. Staying private allows founders to focus on long-term goals—but it can also limit liquidity for employees and investors.

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Should I join a 15-year-old startup offering equity?
It depends on the structure. If the company is stable, transparent, and offers clear equity terms (with time-based vesting), it could be a great opportunity. But if the compensation is below market and equity depends solely on an undefined future event—proceed with caution.

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