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I'm one of those "most people" right now. I make a a great wage and have savings in the bank. However I have a 6 month old baby at home and a wife who is takin

I'm one of those "most people" right now. I make a a great wage and have savings in the bank. However I have a 6 month old baby at home and a wife who is taking time off from her career to look after our baby. I also left a job I was at for almost 5 years and exercised my options on the way out. This cost me almost $30k in cash. At my new job early exercising would cost me nearly $40k. Spending $40k to early exercise this startup's equity grant feels like it might be a little irresponsible. It wouldn't surprise me at all if other people didn't have that much lying around.

tempsy 4y ago
These types of companies self select for people who are comfortable taking on more risk. If this is your thought process why would you even put yourself in a situation where you pick an offer from a company that offers options as part of your comp over RSUs or a public company? I don’t doubt that many people have the same thought process, but if I decline to early exercise from a company that offers that option the alternative is a massive tax bill down the road that I didn’t need to pay if the company does remotely well.
- dopamean 4y ago
  I selected the company I'm at because they offered me the highest salary of all the places I was interviewing. They also have a product in domain I'm very familiar with and are a size that would allow me to have a big impact on the engineering org. Basically this opportunity checked all the boxes I set out to check when I decided to leave my last job. I'll vest my options here without exercising and if they turn into something one day that'll be nice. In the meantime I'll collect the nice salary I negotiated for myself and grow my career the way I wanted. Edit: A little clarification about my last role. I took that job because they were using tech I wanted to learn and they had a team I wanted to work with. They also offered me salary that was a healthy bump from where I was at at the time. I didn't early exercise those options back then because I didn't know enough about the company to justify plunking down the cash. After being there nearly 5 years I believe in the company a lot and see the exercise as a smart investment. I don't have that clarity yet for my current role and so it just doesn't make sense to me to early exercise.

tempsy 4y ago

These types of companies self select for people who are comfortable taking on more risk. If this is your thought process why would you even put yourself in a situation where you pick an offer from a company that offers options as part of your comp over RSUs or a public company? I don’t doubt that many people have the same thought process, but if I decline to early exercise from a company that offers that option the alternative is a massive tax bill down the road that I didn’t need to pay if the company does remotely well.

dopamean 4y ago
I selected the company I'm at because they offered me the highest salary of all the places I was interviewing. They also have a product in domain I'm very familiar with and are a size that would allow me to have a big impact on the engineering org. Basically this opportunity checked all the boxes I set out to check when I decided to leave my last job. I'll vest my options here without exercising and if they turn into something one day that'll be nice. In the meantime I'll collect the nice salary I negotiated for myself and grow my career the way I wanted. Edit: A little clarification about my last role. I took that job because they were using tech I wanted to learn and they had a team I wanted to work with. They also offered me salary that was a healthy bump from where I was at at the time. I didn't early exercise those options back then because I didn't know enough about the company to justify plunking down the cash. After being there nearly 5 years I believe in the company a lot and see the exercise as a smart investment. I don't have that clarity yet for my current role and so it just doesn't make sense to me to early exercise.