The myth of the IPO
The startup mythology says: work at a startup, get equity, wait for IPO, retire rich. This narrative is powerful and motivating. It's also almost entirely false.
The statistics are clear: of the millions of startups created each year, fewer than 1% will ever go public. Most startups don't IPO. They get acquired, they stay private indefinitely, they shrink, or they shut down.
Yet most startup employees plan as if an IPO is inevitable. This is a mistake. You need to understand the other scenarios - and whether your equity has value in them.
Reality check
Less than 1% of startups IPO. Most exits are acquisitions, recapitalizations, or no exit at all. Plan accordingly.
Scenario 1: The company gets acquired
The most common "exit" for venture-backed startups is acquisition. Another company buys the whole business.
In an acquisition, your shares usually get bought out for cash (or stock in the acquiring company, though cash is more common). The total purchase price is divided among shareholders according to the waterfall we discussed before.
If the acquisition price is high enough to pay all the liquidation preferences, common shareholders get a real payout. If not, you might get nothing. And there's always the question of whether the deal includes earnouts or retention bonuses - sometimes the "acquisition price" is lower than it seems because some money is tied up in bonuses for staying through integration.
The timeline matters too. An acquisition can close in 3 months or take 2 years. During that time, your shares are locked up and you can't sell them.
Scenario 2: Down round or restructuring
Sometimes a company raises money at a lower valuation than the previous round. This is called a down round, and it's bad news for common shareholders.
In a down round, your ownership percentage stays the same, but the value of each share goes down because the company is now worth less. And if the down round is severe enough, it can mean that preferred shareholders have more in liquidation preferences than the company is worth.
This creates a situation where common shareholders are "underwater" - the preferred shares' claims exceed the company's value. In that case, common shareholders have close to zero value until the company gets much bigger again.
Some companies also do recapitalizations, where they essentially rewrite the cap table. This is usually bad for common shareholders too.
Scenario 3: The company stays private
Many successful companies never go public. Stripe, SpaceX, Discord, Canva - these companies are worth tens of billions and are still private.
If your company stays private but profitable and growing, your equity might have value, but you can't easily access it. You're locked into illiquid shares in a non-liquid company.
Some mature private companies do secondary transactions, where employees can sell shares to outside investors. But many don't. If your company stays private, you might own equity that's worth something, but you can't convert it to cash without the company's permission.
Scenario 4: Wind-down
Some startups simply run out of money or the business doesn't work. In a wind-down, the company sells off assets and pays back creditors. Whatever remains (if anything) gets distributed to shareholders in order of the preference stack.
In most wind-downs, common shareholders get nothing. The company owes money to banks, employees, landlords, and investors - and the liquidation preferences mean preferred shareholders get paid before any of that.
Scenario 5: The company IPOs
This is the scenario everyone dreams about, but it's the least likely. When a company IPOs, all shares become liquid - you can sell them anytime. But IPOs are also unpredictable (prices can go up or down), and you usually can't sell immediately (lockup periods).
And here's the thing: if your company goes public, that doesn't mean your shares are worth a fortune. Google employees made out great. But early employees at companies that IPO at inflated valuations and then decline can lose a ton of money.
What you should actually do
Stop assuming an IPO is coming. Plan for acquisition or indefinite private status. That's the most likely outcome.
Understand your cap stack. Get the waterfall analysis we discussed earlier. Know at what valuation you'd actually get paid in different scenarios.
Don't overweight equity in your financial planning. If your equity is supposed to be 50% of your net worth, you're making a bet that might not pay off. Take a salary you can live on, and treat equity as upside.
Explore secondary options early. If your company is still private after 5-7 years, see if there's a market for secondary shares. You don't have to wait for an exit to see what your shares are worth. Many successful private companies have secondary markets, and you can sell a portion of your stake to get liquidity without waiting for an IPO.
Understand the 90-day window on options. If you leave your company, you have 90 days to exercise. If you don't, your options disappear. Plan ahead.
Think about diversification. Even if you believe in your company long-term, being concentrated in one private company is risky. Use liquidity events (secondary sales, bonuses, salary) to diversify.
The secondary market as a bridge
This is where the secondary market comes in. If you work at a successful private company that's not going public (or not going public anytime soon), you don't have to wait passively for an exit. You can sell some of your shares to investors who are interested in the company.
A secondary transaction lets you get some liquidity, diversify your net worth, and lock in value - without waiting for an IPO. And you can do it while still working at the company.
That's the real value of understanding what your equity is worth. It's not just about the headline number. It's about making informed decisions about when to hold, when to sell, and when to move on to something else.
Next step
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