Reap the Rewards: Maximizing Your Gains from Working at an Early-Stage Startup

The rise of the tech industry has created unprecedented opportunities for early employees, who are now able to make fortunes from stock options. For example, Stripe is offering to buy back some of its shares from early employees in order to help them pay their taxes upon exercise of their stock options. This is a unique situation that could allow employees to make more money than they would have made had they taken a job at BigCo over four years ago; however, there are still risks associated with working at an early-stage startup.


First and foremost, it’s important to remember that stock option grants expire after 10 years. This means that even if you join an early-stage startup and hit the jackpot with your equity grant, you may not be able to collect on it if the 10 year mark passes before the company exits. Additionally, while Stripe’s situation is unique and can be beneficial for its early employees in terms of post-tax cash gains due to their ability to sell some shares back directly from those employees or via a secondary sale where Stripe buys some of their stock back – other companies may not offer this same benefit and as such can limit employee liquidity until IPO or prevent it altogether via transfer “veto rights” which ensure control over ownership (or cap table) and prevent undesired post-tax cash gains for those involved.

Finally, it’s important to note that while working at a startup can lead one down a lucrative path should everything work out – startups are risky venture by nature which often don’t succeed due traditional failure methods (e.g., bankruptcy). The potential upside must be weighed against potential downside (e.g., opportunity costs), especially when considering whether it makes sense financially speaking as opposed just skill set wise; thus making sure you research thoroughly any company you decide join before doing so is paramount in assuring success - both personal and financial - when joining an early stage startup

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