Ask HN: Ever been the last engineer at a failing startup? | Hacker News Reader

Ask HN: Ever been the last engineer at a failing startup?

49 pointsthroway18492943 comments

Between layoffs and resignations, I am now the only remaining engineer at a tech startup. Just curious if anyone else has been in this position before and how you handled it. Bail on the company asap? Stick it out to the end and try to turn things around?

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I was the second to the last engineer at a startup that dropped from 15 to 3 people. my boss was the CTO, who I worked with on the perpetually 6 months from release “idea”. I switched to work for marketing guy, and together we shipped an update to a published product that had fallen on bad times. The update did great business, leading us to hire and grow till the company employed 100 people.

Did you enjoy any out sized compensation for this?

Directly no. Company was a partnership and I kept getting told they couldn't offer options.

Indirectly though my pay doubled in two years and then I got hired by Apple because of the resume I built.

You should see it no differently than any other stage of any other gig: look after your own interests first since no one else is going to. Do you have better options elsewhere? Then jump ship. What's in it for you to stick around? If nothing, start looking since you're likely to be out of a job soon anyway. If they're asking/expecting you to go above and beyond to try to turn things around, what's in it for you to do so? Without a sizable equity stake (i.e. being a co-founder... and even then, the equity isn't sounding very appealing given the current situation), the only question you should be asking is 'what's best for me?' when considering your options.

Of course there may be non-monetary mitigating factors that only you can evaluate: do you really enjoy the work? Are you learning skills that you and/or future employers will value? Is it easy work for the money? etc. But considering the fact that they've already gotten rid of all the other technical staff via layoffs and attrition, you should be well disabused of any illusion of loyalty on the employers part. You owe them none. And redoubling your efforts is likely to make the endgame twice as painful for you if you stick it out.

Last year, I was working for a biotech startup that was doing lots of interesting work but not making lots of interesting profits. Somehow the founders convinced a big company to buy us, and we spent about three months transitioning over to the new company. All of us knew the company had been in trouble, so it seemed like this buyout was the sensible thing for everybody, and all seemed well. The old owners got their millions, we lost all of our stock options (of course), but at least we still had our jobs. We spent the next three months being absorbed into the new corporate behemoth, until the Tuesday before Thanksgiving last year. I got an e-mail the day before that there was a mandatory 8 AM meeting for all of the new employees. I showed up, we all got on the call, and it was a recording informing us that all three of our offices were shut down effective immediately, and we would be informed of our separation details by personal e-mail. I got two weeks of severance and was unemployed with effectively no warning just before a major US holiday. If something comes up, you should probably take it.

Why would you lose your stock options when the company got sold?

I wasn't fully vested.

So you didn't lose "all" your options, right? Or do you mean you didn't even have the first tranche (usually 12 month) options vest?

Well, what actually happened was we agreed to transfer our options to the new company, but the vesting period started over again. Since the old options were worthless anyway, it sounded like a good deal (and it was the only option we were given). So then when we were all fired three months later, nothing was vested.

The old options were worthless because the acquisition price per share was below your strike?

If the company was sold for less than it raised, then common stock is usually worthless. Investors have preference on distribution to where they will at least get their money back before any non preferred shares pay out.

I have left three startups that seemed like they were going nowhere. All three still exist, in a stagnant sort of way, but the friends who still work there seem pretty depressed. It's amazing how long you can keep a lousy business on life support.

You'll be happier with something new, and it's much easier to find a new job when you don't desperately need one.

Yes I have. Are you one of the founders? No? Then get out, out, out, out.

How is the last engineer at a failing startup different from the first engineer of a 'starting' startup? You're in a startup, volatility is a given. At least a failing startup knows more than a 'starting' startup.

I'd say the main one is that investors now can see the historical growth of the company and will see red flags all over if the company has taken a nosedive, as described.

It's different because the honeymoon is probably finished. You are likely considering how to best part instead of how to best work together.

And you are thinking about what went wrong, how much did you contribute to it, what could you have done better, did I overestimate myself or the team or the product? What is my next step? After X years, what was my return on investment? (i.e. not money but skills, connections, personal growth)

Why act so blasé about it? "Oh X died, he was living, dying is a given, why the tears?"

How is a person being born different from a dying person? First has hope, dreams, enthusiasm and optimism. Latter may not.

As long as you're having fun, learning new things, and not missing out on a great opportunity it makes sense to stay. That being said, depending on your job market, it doesn't hurt to look around. You don't have a hard decision to make until you have another job offer on the table.

Good advice. I was one of the last on board at a startup that eventually sold its assets to another company. We were treated well, but I was lazy in my job search and the next job I should have thought harder about rather than taking the first offer and first interview I had. Good luck, OP!

> You don't have a hard decision to make until you have another job offer on the table.

You don't have a hard decision to make until youve been fired and you don't have a backup plan.

There is no decision there

Yes. I worked on an application to detect major events around a topic using the Twitter firehose. It created alerts for, eg, when the Ukraine changed prime minister, showing alerts for the event way before BBC and Sky news had the story online (if you're interested there's screenshots in my portfolio, https://mikemaccana.com, the app was called 'waves').

CEO kept saying we were funded and had 'infinite' runway whenever I (lead engineer / CTO) asked. I never believed him, and then one day he turned round and decided to shut down the company. We're still good friends, but I wouldn't go into business with him again.

I spent a couple of weeks cleaning up docs for if someone discovered the git repo in future as it was hinted he might get some contract help in once the CEO sorted out the finances. I don't think it's ever happened.

I have been in a similar position. In case you stopped receiving your salary, you should bail immediately. If you are being paid, start preparing to jump ship while continuing to work.

Also, make sure to not burn yourself out -- management laying off everyone else isn't justification for you working double shifts. It was their decision, so the consequences should fall on them, not you.

If you can, look for other opportunities. The best time to look for other opportunities is before you need them. It will also allow you to understand your job relative to other jobs, and this knowledge will give you a much clearer reasoning for your decision making.

I was the last engineer of a small startup (from 4 full-time employees + ~4 contractors). I stayed a year beyond everyone except the founder/CEO in an attempt to launch the nearly-ready service, despite clear red flags. I achieved the established technical goals multiple times, but it became obvious the product would never launch due to non-technical reasons. It was a big mistake from which I have not completely recovered.

I'd suggest seriously considering what you hope to achieve and what you can reasonably expect from several angles: Financial outcomes, career trajectory, and personal motivations to name a few.

A few relevant questions: Have the issues which led to the current stagnation been addressed? Does the startup have a product that has been validated and can produce sustainable revenue? If not, what is the likelihood of securing (more) funding? Are you being paid well (without considering any equity/options)? How will your decision to stay look to future employers, considering likely outcomes? Why do you want to stay? Because you enjoy it? The challenge? Responsibility/Obligation (and to whom)? Sunk costs? Ego? Hubris? Messiah complex?

If you do decide to stay, I would suggest setting concrete limits/criteria for when to move on, so you don't get stuck in a zombie company.

If you don't mind me asking, how have you not completely recovered? Were there negative repercussions you finding employment elsewhere?

There were some financial repercussions which I recovered from quickly. The lasting issues were from burnout as a result of working myself to death trying to deliver (and likely exacerbated by pre-existing depression issues).

I'm actually not sure whether it would cause employment issues because I haven't had any desire to program professionally since then (it was a couple years ago).

Not knowing anything else, there's a good chance you know your position may be gone in the next 3-8 months... One man shops can do a lot, but for a tech startup of note it's a joke.

This window is the time to get your resume together, watch online courses on company time, and start using some hot new tech in some capacity at your job. Your time should be focused on building your resume and attractiveness on the job market, and to differentiate yourself from other applicants.

And the company will close faster. You killed it.

Don't join a startup.

It's not fair or reasonable to pin the blame of failing a business on the last employee being fired.

Even if that last employee did any harm to the company, that would be like blaming that ladt straw for injuring that poor inocent camel.

The company will close faster? Oh no!

Muuuuuch better to work 80 hour weeks, get a serious case of burnout, have no resume developed, not be prepared for your job search, and keep those-people-who-are-not-you's business going... what... a single day longer? A week?

Or how about the most likely scenario? 0 seconds longer.

I'm not sure how much value a single engineer can create for a whole company between current date and company shutdown, amidst the layoffs and all... But if the marginal difference between 100% productivity and 25% productivity of a single engineer for a couple months is directly visible on the companies overall revenue, to the point its termination-date is meaningfully altered, then you have either got someone who will be working at Amaz-oogle in weeks time regardless (and no good explanation for going under!), or we're talking about a revenue stream that is comparable to selling aluminium cans found in the trash.

Things are already trending south. Self-interest is a moral imperative. The rats that staple their feet to boats drown.

Do get your resume together..but your resume should always be together. Always assume tomorrow might be your last day on your job (documentation, resume, networking, etc.), and you will be in a much better position. I have been working as an consultant in my current domain since 2001 (for various reasons, risk of going full-time on a startup hasn't been something I could do), and have never been out of work, in a very volatile area.

That said, you get what you give.

DO NOT watch videos on their dime, unless your manager tells you that you can take courses and study some as part of your professional development, which they should unless in a crunch (no professional development is a major red flag).

DO go to work every day as if you were a footballer stepping onto the field in the Final. Even if the startup fails, the people you meet will go on to other jobs. Stay in touch with them, because networking is key...for people networking well the resume is simply a formality. The people you've worked with know your skills, and in some ways more importantly know they can work well with you.

I was actively recruited out of my last company. I was the last person engineering in the company but not the last engineer. Over a dozen other people had left by the time I did. The management was somewhat dysfunctional the whole time; but somewhat functional. We were always a subsidiary of a larger start-up which is still in business. Even thought they wanted it to be a unicorn worth billions it has been valued at 100 million for over five years now. They tried several times to hire me into the first company but the management disfunction there was very similar. Most importantly the company hired a replacement and is still profitable, with its existing customers. I just needed a change and I didn't do the hard work of finding a job until I was actively recruited. Once I received a job offer I was countered at the exact same level (not better though!). It seems that I myself had gone stagnant. I like the advice from others, don't be a person at a small startup who doesn't own part of the company. Just don't.

Not the last, but near it. Also not the first, but near it. There's a huge difference between the two.

In my experience a sinking ship doesn't start floating, so don't stick around for that reason. It was also depressing to be there after all my friends had been laid off or quit. In reality I probably stayed there two years too long, and it was because of the people I worked with.

I've been maybe not the last but one of the last handful quite a few times. If you don't believe in the company or don't like working with the people there, there's no reason to stay.

If you like being there, and you think it could work, I'd say to look for three things:

First, think about if there is a "turning point" moment that you're working toward. E.g. are you close to shipping your alpha, is there a big show coming up that could realistically generate a lot of publicity, etc? There's always some deadline or artificial milestone but is there a real one that people are actively working towards and isn't just wishful thinking? Or is everything just plodding along waiting for a big break to just happen?

Secondly, do you have a few customers (or testers) that are very passionate about your product? You don't need a lot of them, but if there is one or two people that really love the product that's a good sign that it's a real thing.

Third, how has the company or CEO handled bad news in the past? Was it a surprise or did they let everyone know it was coming and try to prepare together. If they're not being honest about their trajectory and their funding it can be a pretty unpleasant situation, but if everyone is working together to right the ship it can be a positive and bonding moment.

Finally, I would say to make sure you set the ground rules with your manager or CEO about payment. e.g. "I really want to see this company succeed and I will do everything I can to make it happen, but I have my own financial obligations, so I won't be able to come in if I haven't been paid yet for the previous pay period." etc. It's extremely common for people to go weeks or months unpaid and then the company goes dark suddenly and you're left without recourse. This is not even due to shady people or fraud, it can be good, well intentioned folks that think they have a solid line on more funding that falls through, or just aren't tracking finances carefully enough.

Not exactly, but I was the only engineer at a small local publisher that was in transition of being acquired by a blue-chip company. But the transition seemed to be chaotic for the small company because they just had a blackout, causing them to lose days of work ahead, and the acquiring company didn't care and wanted to keep the goals as if nothing happened.

This lead to me putting out multiple fires related to one of the e-zines the small publisher had. I replaced the only developer who just greeted me on my first day and left. Clearly they didn't foresee how to budget for a tech department.

A lot depends on what the founders are looking to achieve. If they are still trying to grow the business then this creates some opportunities for you to make technical decisions and push for some equity.

On the other hand if they are just looking to milk whatever profits are available and you are running round maintaining a lot of legacy code it could be career death.

In either case the standard advice applies, keep some savings, stay in contact with your former colleagues and keep your technical skills up to date.

Startup, no, but I was the last engineer in an established company that had been around for over a decade and fell on hard times.

I basically spent the last two years building my own business, and learning. When my boss walked in with the expected news that the company was shutting down, I wasn't in the least bit surprised, and was fully prepared for it.

However, I discovered I had a lot to learn about marketing my own business and took another full-time job about a year later.

Not seen this yet but: negotiate hard. Ask for whatever would keep you happy: hours, money, whatever. And don't undersell yourself!

I think this is an important point. If the board is trying to sell the company (assets), the acquirer will want an engineer to at least do a handoff. Having zero engineers left will be a disadvantageous state for the board, so you could potentially negotiate a carve out from the board for sticking around.

I’ve never been in this position but I have a family to feed so I know I would at least have another job in my back pocket, even if I REALLY believed in the company or the team. But I wouldn’t leave just because I was the last.

Not the last one but I have been on a sinking ship. It's not a good experience. Definitely plan ahead and look for new options but talk to the founders.

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