How Can I Effectively Exit a Company After IPO?

Stripe offers 1 year grants so the risk resets every year. However, if the Stripe IPO is successful and the share price is much higher than the price you started at, you will only reap the benefits for 1 year.

If a company IPOs, your default operating mode should be to stay, not leave. This is because being one of the "pre-IPO folks" carries a lot of weight if the company goes on to be successful (this was the case at Meta). Having that tenure is extremely helpful in fostering trust and getting promoted, especially to Staff+, as I talk about in my promotion course here: https://www.jointaro.com/course/nail-your-promotion-as-a-software-engineer/you-cant-job-hop-to-success/

I worked at a company that had an IPO, and we had a 6-month lockup period where we couldn't sell our shares. I imagine there may be a similar case with Stripe, so you wouldn't be able to sell your shares immediately after Stripe IPOs.

There are two schools of thought about how to treat your shares once you can sell them:

1. You can treat your shares like cash and sell them immediately.
2. You can hold on to your shares and reap the significant financial benefits if the company continues to grow.

Option 1 is one way to derisk yourself because you can sell your financial concentration in one company and use that cash to diversify into different companies. The con is that you end up eliminating your upside if a company does well. A common question people ask themselves is: "Would you invest in the company if you had cash reserves lying around?"

Option 2 is the riskier approach, but it can come with significantly more upside if the company does well. The concentration into a single company is how people can become very wealthy.

I would try to think about companies in a long time horizon, say 5-10 years when you make your decision. It can be easy to be reactive when you see short term fluctuations with the share price. Here are some other questions that you have to ask yourself:

• Do you need the cash now? Maybe you need a down payment for a house.
• Do you see any reason why Stripe would/wouldn't succeed? How much conviction do you have?
• Does the company have a moat where competitors will have difficulty competing with them?
• How sticky is the product? How much effort is required for a company to move from Stripe to a competitor?

Are you being offered private RSUs that would convert to public RSUs (and vested private shares convert to public)? Or options? What is the valuation they are using when determining a dollar amount value of the offered shares?

You can’t guess how the market will react. Normally non-public you treat the stock as a bet, not your primary compensation.

Would you accept the offer if the stock was worth 50% of the number they presented?

It is really a risk tolerance question. I don’t get how it would be helpful to quit near the IPO?

Not really answering your question, but I am very bullish on Stripe :) I don't know the exact value of the IPO, but I am very sure there is fundamental value in the company, so the stock won't go down by a huge amount.

I think $50B+ valuation is safe, especially as the economy recovers.