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I’d have to actually believe in the product. I’ve seen a lot of these and don’t really think the product is that exciting so I would never join.
Best case, you spend 10 years there and become an executive making millions off RSUs (1% chance)
Worst case, you waste a few years there and learn a lot but don’t cash out.
A 3 year guaranteed contract at a salary and bonus above my current rate, and RSUs over options.
And even then, I probably still wouldn’t bother. They probably won’t have any IP protections because “the juice isn’t worth the squeeze” (🤢) and will be insistent that their tech stack/development team/GTM model are so unique that no one could match them… it’s all smoke and mirrors.
This^
Do not count stock options or grants as anything. I worked in startups for a number of years. 95% of them do not make it to IPO or buyout. And 4.9% of them buyout for a reasonable price that gives you a bit of spending money/nice little bonus.
0.1% will have a nice payday. But it will be years if they are Series A. So it’s less than Monopoly money and certainly shouldn’t be considered compared to RSUs or company stock shares.
Don't consider stocks as real. Assume it'll be worthless. What you're looking for is the potential to learn and grow for a future role.
If this role has that + good salary, take it.
Look at the founder’s credentials. Have they raise and exited before? Do they have a track record of success. These are serious considerations on top of being excited about the product, pmf, etc.
This is important - track record of exit. Ironically, I would discount a strong track record of raising capital, especially at Series A. With founders and certain "top tier" VC firms, there's a strong propensity that a lot of money is raised and that VC firms push back on offers to buy the company early in the process. This often results in a prolonged exit with high liquidation preference where employees get nothing after their 10 years of work.
The product. If this Gen AI startup is just a Chat GPT wrapper then def not
Oh absolutely not. Nothing to do with OpenAI. Very different route being that it’s very responsible AI focused
For me, and a lot of people I’ve worked with that have made this move, a big question is “how hard would it be to go back?”
At Amazon a lot of people have left, gone to a start up, then come back (start up didn’t make it, or they cash out, etc). Boomerangs are common here though. If you’ve got a good network and you’re old or current employer would likely take you back because you were a top performer, that minimizes the risk of things don’t pan out.
5-time early stage startup survivor here. 3 cratered fairly fast two exited with combined valuations of $375 million (in early 2000s). Other experience is with firms ranging from $100 million revenue family firm to two Fortune 500s and a $300 billion+ revenue global firm. Here is my take on the startups. They demanded the very best performance and rewarded practical achievement beyond anything I have experienced since. We, the crew that built those firms, have the most incredible bond to this day. Startups are (generally) less married to arbitrary boundaries and far less tolerant of mediocrity. None of that “well, I have been here for 18 years...” bs. Nobody cares. The first round of talent often gets surpassed by people with more clearly defined specialization as the firm heads for real capitalization. It coincides with a shift from experimentation to prove a business model to emphasis on scaling up on efficiency and effectiveness. It is also an inflection point that involves the VCs placing carefully selected personnel into key leadership roles. Early adaptable systematization gives way to more robust enterprise systems or are rolled (uncomfortably) into operations of an acquiring firm. Compensation was phenomenal: $150k - $180k for Sr. Manager/Director roles (20 -25 years ago). Stock options were worthless in both buyout exits. Second exit cost me $100k of personal out of pocket investment dollars. (VC had placed a COO who controlled financial interests in favor of the VC. Basically ran us out of cash so the next VC round was a desperation round.) Today it is sometimes difficult to reconcile mediocre corporate-animal leaders (administrators) with my expectations of real leaders.
IBM1: Yes. But I was so destroyed from 4 years of constant brutal workload that I did not work for six months after my exit. It was one hell of a great professional experience, but the physical and mental wear and tear was indescribable.