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I didn't understand startup stock options - it cost me $300K

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I was an early employee at a hyper-growth startup. Life was rich until I tried to quit. This is the story of why I had to pay $300K to unshackle myself.  There’s surprisingly little coverage on this topic, maybe because nobody is incentivized to reveal the unsavory truth, or because VCs and founders get a lot more airtime. Here’s everything I wish I knew before I joined a startup. I hope it can save you from burning piles of money like I did.  ‍ For all the talk around “disruption”, startups exert a surprising inertia over employees. “Golden handcuffs” is most often used to describe the inertia experienced by big tech employees who make a ton of money and have a hard time leaving. It also applies to startup employees who make a ton of paper gains and have a hard time coming up with real money to keep them.  ‍ Working at a startup usually requires taking a salary cut. The deal is sweetened with equity — an ownership stake that can mint millions. The most common equity vehicle, espec

I didn't understand startup stock options - it cost me $300K Why I paid $300K to quit a startup How startup equity really works I was an early employee at a hyper-growth startup. Life was rich until I tried to quit. This is the story of why I had to pay $300K to unshackle myself. There’s surprisingly little coverage on this topic, maybe because nobody is incentivized to reveal the unsavory truth, or because VCs and founders get a lot more airtime. Here’s everything I wish I knew before I joined a startup. I hope it can save you from burning piles of money like I did. ‍ Golden handcuffs For all

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