>> The same general situation has happened to me twice now and I am wondering if it’s something I can break free from or if it’s just the nature of the Startup beast - or what
9 out of 10 statups will fail. So if you're joining startups uou can expect them to (mostly) follow this pattern.
If you don't like this pattern the perhaps look for jobs at more stable (ie non VC) companies. And consider companies not directly in tech.
As regards to today, yes the job market is swamped. Don't quit your current job unless you gave something else to go to. But perhaps start actively looking.
Given you're a generalist, it's likely you'd make a good fit in a company which has been around a while, and which has a reasonable "IT" department, as distinct from a pure IT company.
imho if you're at a company, and they're having layoffs... it's generally better to be laid off, get some severance, and end up at some other company that is hiring / growing, rather than a "survivor" who now has more work to do with fewer people at a company that is possibly troubled, unlikely to give any good pay increases any time soon, etc etc.
re #3 - no, "jack of all trades" tends to be a career trap / dead end. companies hire for specific skill sets.
You're not unlucky, you're just really good at absorbing pain. Companies keep you because leaving would break things. That's leverage... use it. Negotiate equity or walk.
The only reason to accept the negatives of working at a startup (stress, below market remuneration, workload) is the potential upside (rapid growth and an eventual liquidity event).
If the startup is contracting, it sounds like the only potential upside has disappeared. I’ve been in a similar situation before and made the mistake of sticking around, to the detriment of my physical, mental and financial health. Obviously businesses pivot and turn around, but that’s the exception rather than the rule. Most startups fail, and if your startup is starting to falter, I’d say it’s about to prove the rule.
I’ll give you the advice I wish I had:
Run. Start interviewing like crazy and get another job. Good luck.
Honestly only read enough of that to get the gist, but having been through many iterations of this over a couple decades of living a life in SV tech - you carry on. Each time you take away (hopefully) some improved sensitivity to the flags and signs that help guide your future decisions. That said, it’s also the nature of a fast moving industry to rapidly ideate-float-fund-fold.
>> The same general situation has happened to me twice now and I am wondering if it’s something I can break free from or if it’s just the nature of the Startup beast - or what
9 out of 10 statups will fail. So if you're joining startups uou can expect them to (mostly) follow this pattern.
If you don't like this pattern the perhaps look for jobs at more stable (ie non VC) companies. And consider companies not directly in tech.
As regards to today, yes the job market is swamped. Don't quit your current job unless you gave something else to go to. But perhaps start actively looking.
Given you're a generalist, it's likely you'd make a good fit in a company which has been around a while, and which has a reasonable "IT" department, as distinct from a pure IT company.
imho if you're at a company, and they're having layoffs... it's generally better to be laid off, get some severance, and end up at some other company that is hiring / growing, rather than a "survivor" who now has more work to do with fewer people at a company that is possibly troubled, unlikely to give any good pay increases any time soon, etc etc.
re #3 - no, "jack of all trades" tends to be a career trap / dead end. companies hire for specific skill sets.
You're not unlucky, you're just really good at absorbing pain. Companies keep you because leaving would break things. That's leverage... use it. Negotiate equity or walk.
The only reason to accept the negatives of working at a startup (stress, below market remuneration, workload) is the potential upside (rapid growth and an eventual liquidity event).
If the startup is contracting, it sounds like the only potential upside has disappeared. I’ve been in a similar situation before and made the mistake of sticking around, to the detriment of my physical, mental and financial health. Obviously businesses pivot and turn around, but that’s the exception rather than the rule. Most startups fail, and if your startup is starting to falter, I’d say it’s about to prove the rule.
I’ll give you the advice I wish I had:
Run. Start interviewing like crazy and get another job. Good luck.
sounds like you need to tell your CTO to lead more on the tech side or get enough equity to be an equivalent head of engineering level
Seconded. You’re only there because it’s a rocketship. If the rocketship is out of fuel, parachute.
Honestly only read enough of that to get the gist, but having been through many iterations of this over a couple decades of living a life in SV tech - you carry on. Each time you take away (hopefully) some improved sensitivity to the flags and signs that help guide your future decisions. That said, it’s also the nature of a fast moving industry to rapidly ideate-float-fund-fold.
Have you tried owning 40% or more?