Left a big corporate gig to work for a startup, but sold a bill of goods on what the job would actually be. Boss is an ego maniac who blames everyone else for his own bad decisions and routinely yells and cusses at all of his staff and talks about everyone behind their backs. Already ran off some of our top talent.

The owner has no clear vision for the company, changes his mind daily about what needs to take priority, and will not take advice from anybody on his team. He also makes an ass of himself in front of customers by speaking in platitudes about how our technology is the best and everyone else's sucks for one reason or another.

Never been in the situation where I need to cut bait for the next career move so soon (5 months in), so unsure how to handle the inevitable "why are you looking for a new job so soon?" question from new perspective employers. Or do most folks understand toxic work environment situations and I'm overthinking this?

Your mental health is more important than that job and explaining that after you started you saw how the environment is and that multiple very talented people left due to the boss' personality would be well understood. And any potential employer that doesn't understand that should be crossed off your list of places to work.

which industry?


i work in construction and have been very successful navigating toxic workplaces. in construction it is great b/c you can hide on the road if you need to. Those working in 9-5 office gigs...pfft - stop going in and see how long it takes for them to stop paying you.

evestor1 said:

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which industry?


i work in construction and have been very successful navigating toxic workplaces. in construction it is great b/c you can hide on the road if you need to. Those working in 9-5 office gigs...pfft - stop going in and see how long it takes for them to stop paying you.

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Instrumentation Development. I left big chemical to try a new angle with my career. Specifically I'm in applications development now, and am using 20 years of industry knowledge to demonstrate where the technology we are developing can be used, engaging with customers, and finding good matches.

As you can imagine, the sales cycle for the first sales take a while until we get traction and references. We have customers that literally want to make a deal with us on our first sales but are working on their capital plan. Our boss is pissed we didn't close the deal already and just ran off our lead marketer. Now that he's gone, it's suddenly a technical problem and he's after me.

I work with a lot of startups. I'm sure you know most of them fail, but let me go a little deeper. Basically zero startups are ever more than a few months away from fundraising, and if yours isn't growing quickly and hitting milestones, your next round of investors will require a big piece of your hide to invest, if they are willing to invest at all. They'll demand preferences and dividends that are paid out of the liquidation proceeds before common stock holders (ie you) see a dime, and they'll give you a valuation that means they get more of the company (and therefore a bigger chunk of the exit proceeds remaining after their preferences and dividends). In aggregate, this means that your currently flailing startup will have to turn things around and hit a home run exit for all those options you've were awarded to amount to anything material.

Even paper successes can be failures for the people at the bottom of the pile. I'm talking to a company right now that for all the world looks like a roaring success: $350 million of revenue, adding new customers, cutting its burn rate and moving to positive cash flow in the next year, valued at over a billion dollars (coveted unicorn status). Well, they hit a rough patch years ago and exactly what I described occurred (big preferences). Worse, since there were now big preferences on the capital stack, the next investors demanded them too since they knew that the people behind them in the liquidation order would be taking an outsized chunk of money. The whole thing snowbalked and now the company is in a position where it has to exit at >$1.45 billion for the common holders to get a dime. Granted, this is the worst I've seen, but I want to highlight how many ways staetups can go wrong.

One dark horse possibility that could change the above: how strong/experienced are your investors/backers and how much of the company do they own? If you're backed by a few decent venture capital firms that in aggregate own >50%, they could force out the leadership team and replace it with a better one. I've seen that happen too.

Your last question ie what do I say in an interview? I'd just go with "I took a chance and joined a startup and it didn't work out. The company didn't hit some milestones and now it's going nowhere." Everybody knows how risky these are and won't judge that response.

Deputy Travis Junior said:

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I work with a lot of startups. I'm sure you know most of them fail, but let me go a little deeper. Basically zero startups are ever more than a few months away from fundraising, and if yours isn't growing quickly and hitting milestones, your next round of investors will require a big piece of your hide to invest, if they are willing to invest at all. They'll demand preferences and dividends that are paid out of the liquidation proceeds before common stock holders (ie you) see a dime, and they'll give you a valuation that means they get more of the company (and therefore a bigger chunk of the exit proceeds remaining after their preferences and dividends). In aggregate, this means that your currently flailing startup will have to turn things around and hit a home run exit for all those options you've were awarded to amount to anything material.

Even paper successes can be failures for the people at the bottom of the pile. I'm talking to a company right now that for all the world looks like a roaring success: $350 million of revenue, adding new customers, cutting its burn rate and moving to positive cash flow in the next year, valued at over a billion dollars (coveted unicorn status). Well, they hit a rough patch years ago and exactly what I described occurred (big preferences). Worse, since there were now big preferences on the capital stack, the next investors demanded them too since they knew that the people behind them in the liquidation order would be taking an outsized chunk of money. The whole thing snowbalked and now the company is in a position where it has to exit at >$1.45 billion for the common holders to get a dime. Granted, this is the worst I've seen, but I want to highlight how many ways staetups can go wrong.

One dark horse possibility that could change the above: how strong/experienced are your investors/backers and how much of the company do they own? If you're backed by a few decent venture capital firms that in aggregate own >50%, they could force out the leadership team and replace it with a better one. I've seen that happen too.

Your last question ie what do I say in an interview? I'd just go with "I took a chance and joined a startup and it didn't work out. The company didn't hit some milestones and now it's going nowhere." Everybody knows how risky these are and won't judge that response.

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This. Just say things are not very stable/secure at the start up and youre looking for something more stable. Everyone will understand.

Any chance to return to the outfit you left? Tell them your mistake and get back on?

Funky Winkerbean said:

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Any chance to return to the outfit you left? Tell them your mistake and get back on?

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Not unless I want to take my old house off the market, and sell the new one and move all my crap back. Plus hope I can get an offer back (doubtful because they are petty and mad I left even though I did all the transitions the right way) and also mess my wife's job situation up too.

For me it was 3.5 months.

I worked from home and rarely saw my family who was literally home all day with me (stay at home mom + 3 kids). Got called into the office and told I wasn't working hard enough and progress I made in 3.5 months had to be doubled in 2 weeks or I might be let go.

Drove home and resigned. Don't regret it for a second, even being still on the hunt 7 months later.

Cromagnum said:

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Never been in the situation where I need to cut bait for the next career move so soon (5 months in), so unsure how to handle the inevitable "why are you looking for a new job so soon?" question from new perspective employers. Or do most folks understand toxic work environment situations and I'm overthinking this?

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Just be up front in the interviews. You took a risk on a startup that had showed good potential but some of the company goals shifted that no longer align with your goals.

Then, be prepared to give 2-3 high level examples without sounding unprofessional.

I wouldn't worry about leaving the current job, particularly if your previous work history was pretty stable. But even if not, it would be pretty easy to say that you left a startup that was turning into a bad situation- I think most can appreciate that those have a high chance of not working out for one reason or another.

Also better to start looking ASAP if you need the income or medical insurance and can't risk having a break without a job for several months. Finding the new job could take longer than you think, and you may regret not starting to look sooner.

Went through a similar situation in a different industry a few years ago. Left what was basically the largest company in my field for a small shop. Wasn't a startup, but the founder's son had just bought out his dad. Was sold these grand plans about what the direction of the company and what the role would be. Ultimately, we didn't see eye to eye and he turned out to be a total control-freak who had to micromanage every aspect of the company. Ended up lasting around seven months before I went back to the previous company because they left the door open for me. It sucked, because I really enjoyed working with the other people there but just couldn't work for the owner

Old boss gave me the advice that once you start hitting that 15 year mark in your career, it's better to leave a job after six months without mentioning on the resume than it is to have several 1-2 year stints.

I'm in year 3 of working in an incredibly toxic workplace. I stick it out for the money. It has been very difficult to find another role but I keep persisting. Life is too short to be somewhere you are not appreciated or valued. Move on.

ElephantRider said:

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Went through a similar situation in a different industry a few years ago. Left what was basically the largest company in my field for a small shop. Wasn't a startup, but the founder's son had just bought out his dad. Was sold these grand plans about what the direction of the company and what the role would be. Ultimately, we didn't see eye to eye and he turned out to be a total control-freak who had to micromanage every aspect of the company. Ended up lasting around seven months before I went back to the previous company because they left the door open for me. It sucked, because I really enjoyed working with the other people there but just couldn't work for the owner

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Forgot to add, now the old company is toxic due to private equity meddling, so I'm still screwed.

Best day to leave would have been yesterday.

Second best day is today.

Only caveat is that you should be financially able to leave.


Had a friend leave a well known crap engineering firm by just walking in, packing up, and walking out. Never even told anyone. I always thought that was pretty incredible. There were zero ramifications. He said someone called a week or two later and asked if he still worked there and he said no and hung up.

That would be awesome to get a few extra days added to your check because no one notified HR or Payroll

You don't stay because it's not worth it. I walked out of a job when I was much younger because the owner was psychotic. I tried to find another job first but it was the housing crash of 2008 and I was in construction. I lasted 3 months. I just recently went to a startup and am realizing that while it's not toxic, it's not going to work and they offered a lot of incentives that aren't happening, so I'm on the search again.