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Comment by sdrinf | Hacker News Reader

The second they go public it triggers a 6-12 months window after which all of their employees can cash out. This will, inexorably lead to an exodus of their most senior peeps, and when it happens, will probably be ground zero for the next gen of fintech startups.

Delaying going IPO this way, amongst other things, is about retention.

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I don’t think this is correct. Then your theory is that every tech company that went public in last 2 years have experienced a brain drain that Stripe has not.

Lock up periods aren’t set in stone. They probably didn’t need to raise money and could have done a direct listing and let employees cash out immediately.

There’s also no lack of buyers for stripe on secondary markets.

whether you can sell on secondary markets is restricted by the company. pretty sure Stripe has not let most employees sell on secondary markets. personally have not seen them solicited on Forge or EquityZen myself.

A fun question to ask when interviewing at a startup is to what extent they block or facilitate employee share sales/transfers. Also check with private markets to see what their experience with that company is.

Ahh I wasn't aware of that, thanks!

How do they prevent you from selling on the secondary market? Would love to see that clause on their options agreement. Most companies have first right of refusal which gives them the option to buy them first.

There are a few clauses but the gist is pretty simple: approval of any transfer of option or underlying share must be approved by the board of directors + they may also exercise their right of first refusal.

A "brain drain" doesn't just mean that people actually quit and leave. They can also dramatically ramp down the intensity because they are suddenly in a very comfortable financial position and the big risk they have been working so hard to avoid (losing their valuable equity for whatever reason) is off the table. It sucks, but that's the way it is for many people. It's hard to keep up the super high level of intensity after so long, especially when the downside case is mitigated by newfound financial independence.

Most tech companies have four-year vesting periods. Lots of people at my current employer, which IPOed in 2020, are still vesting shares from pre-IPO stock grants. As a result, those people have a very strong financial incentive to stick around.

Stripe is a rarity in that it issues one-year equity grants, which would make it more susceptible to brain drain after an IPO compared to companies with longer vesting schedules.

To a certain extend yes you're right. But they've overextended. Realistically there won't be a fertile IPO market at their size/level of valuation in years now. So unless they up their salaries, it's doubtful some people who joined in hopes of cashing out after 1-2 years would be willing to wait an additional 4 or 5.

This is a problem that people are well aware of, it’s mitigated with stock refreshers. It’s not perfect but helps retention.

To some extent, but if you have been around since the early days it’s unlikely your golden handcuffs will be worth as much as your long-vested options.

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