
Ask HN: Ever been the last engineer at a failing startup? - throway184929
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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valuearb
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.

~~~
JamesBarney
Did you enjoy any out sized compensation for this?

~~~
valuearb
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.

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blihp
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.

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commandlinefan
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.

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

~~~
commandlinefan
I wasn't fully vested.

~~~
phonon
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?

~~~
commandlinefan
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.

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

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jpm_sd
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.

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

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navane
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.

~~~
mratsim
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?"

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jmcminis
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.

~~~
cbluth
> 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.

~~~
MrTortoise
There is no decision there

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nailer
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](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.

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robin_philip
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.

~~~
kd5bjo
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.

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spyckie2
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.

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anonlasteng
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.

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

~~~
anonlasteng
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).

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bonesss
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.

~~~
MrTortoise
And the company will close faster. You killed it.

Don't join a startup.

~~~
bonesss
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.

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cellarweasel
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.

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gumballhead
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.

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joeld42
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.

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ccajas
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.

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tonyedgecombe
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.

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HeyLaughingBoy
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.

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

~~~
jtokoph
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.

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auslegung
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.

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amorphous
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.

