I have been a hiring manager for 5+ years now. While this isn't great, as long as you emphasize that your first two were while you were still in school and more or less all of them were at startups, this doesn't look terrible. You rolled the dice, it didn't work out. It also sounds like you were a contractor at one of these places as well, just make sure you emphasize that.
The bigger question in my mind is why you got into so many situations with failing startups- were they doomed to fail and you just didn't have the business sense to see that? In either case, it sounds like you are still only a few years out from graduating, you get a lot of slack for inexperience in my eyes.
Of course I can't speak for everyone, some guy that has been at MegaCorp for 17 years since he stepped out of school may not be as kind, but you probably don't want to work for him anyway.
Regardless though, your latest tenure is 3 years. The trend is in the right direction. If your current situation is bad, now is almost certainly the right time to make a jump- I can tell you first hand, the quality of people we are seeing right now is substandard, if you know what you are doing, you will stand out. This is a great time to be picky not only about the role you accept, but the company as well- an established business that you know will be around in 3-5 years and hopefully thriving is particularly important. Also consider that we are definitely at the top of an economic cycle, the next recession is on the horizon and the weaker companies will feel the pain.
I basically wrote a post of my career life story, but I'll spare you that. Let's just say that each of these places higher ups hid the true danger the company was in until the last second as much as possible. There was always a reasonable explanation for why we failed to achieve success with a product and always something new and exciting to look forward to, until there suddenly wasn't. Like for my current company, they're just "cutting the fat" of the massive workforce they inherited and now we're past that and look at all the exciting things we are working on that will innovate and drive change and blah blah.
Yeah, things might get better here. It does look like their 5 year plan is going more or less in the right direction. But am I willing to wait 5 years with stagnate or no growth (in addition to the three years of no growth I've already endured) with a company that's proven multiple times it's unwilling to loosen its purse strings for just about any reason? I don't think it's worth it, and many other employees didn't either.
I'm mainly only still here because I keep having things happen in my personal life that makes it inconvenient to change jobs at that point (For example I recently bought a house. Mortgage lenders tell you not to quit your job until the closing date for that). And the one benefit of losing the office is we get to work 100% remotely, so I'll do that for a bit while figuring out what I want to do next.
> The bigger question in my mind is why you got into so many situations with failing startups- were they doomed to fail and you just didn't have the business sense to see that?
I think you answered that yourself in the prior paragraph. Joining a company is like rolling the dice. As an employee, you generally have no idea which ones will succeed and which ones will fail. You pick a horse and hitch to it. I look back to my friends in undergrad. We were about as smart and hard working as each other, but comparatively where we are in our careers today seems largely based on how lucky we got in picking which companies to work for.
The bigger question in my mind is why you got into so many situations with failing startups- were they doomed to fail and you just didn't have the business sense to see that? In either case, it sounds like you are still only a few years out from graduating, you get a lot of slack for inexperience in my eyes.
Of course I can't speak for everyone, some guy that has been at MegaCorp for 17 years since he stepped out of school may not be as kind, but you probably don't want to work for him anyway.
Regardless though, your latest tenure is 3 years. The trend is in the right direction. If your current situation is bad, now is almost certainly the right time to make a jump- I can tell you first hand, the quality of people we are seeing right now is substandard, if you know what you are doing, you will stand out. This is a great time to be picky not only about the role you accept, but the company as well- an established business that you know will be around in 3-5 years and hopefully thriving is particularly important. Also consider that we are definitely at the top of an economic cycle, the next recession is on the horizon and the weaker companies will feel the pain.