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Ask HN: Those who've joined a friend's startup as an employee, how did that go?

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Re: Ask HN: Those who've joined a friend's startup as an employee, how did that go?

#91
It's ruined a few of my friendships and been fine for a few others.

I'd recommend doing some high-stakes conflict-generating activity with the person as a test-run beforehand, e.g. run a local event together, travel together, do the same things you'd do as an early couple to suss out where the pain points will be.

Re: Ask HN: Those who've joined a friend's startup as an employee, how did that go?

#92

It ruined the friendship. I was uninformed on how stock grants worked and trusted their advice. They said "I'll take care of you." They made millions from the venture. I was able to buy a motorcycle.

that really doesn't sound like a them problem.

they gave a fraction of a fraction of a percent, from a particular share class that likely was subordinate to other liquidity preferences.

like, even if you were personally more informed the outcome wouldn't be different? you would have rooted for an even bigger upside for the whole company.

Re: Ask HN: Those who've joined a friend's startup as an employee, how did that go?

#93

Earlier quoted context omitted.

> I was uninformed on how stock grants worked Any chance you could elaborate on this? What about stock grants were you unaware of (or misunderstood) until it was too late? What should people reading this watch out for?

I’m not the parent, but it’s really hard to pull a future-proof contract about stock grants. The most frequent shenanigan is probably to dillute the employee shares. Even if you are the CEO, investors can get you fired-in-bad-terms just to cancel out your shares.

If the founder retains a controlling interest in the business (say 51% stock ownership) are they safe from these shenanigans?

Re: Ask HN: Those who've joined a friend's startup as an employee, how did that go?

#94

Poorly. I did all the work while my friend goofed off and ran personal errands all day. The friend eventually made a fortune selling their equity and retired young. I did not get awarded the same privilege. We no longer speak and I still get angry when I think about that. On the other hand, I have made good friends through the workplace who I would start a startup with in a heartbeat.

Such situations make me furious, but not so much at individuals as at the system. Getting equity in a startup is ridiculously high friction. It's often been a deal breaker for me; not because the founder themselves had personal objections, but because of bureaucratic nonsense such as; it was too much hassle legally or other large investors wouldn't like it, etc, etc...

IMO, it should be illegal to launch a limited liability company/corporation and only allow specific people to buy shares. I object to the idea of incorporation and limiting directors' liability to begin with but since it is allowed, at the very least, it should be a requirement under the law that the shares be on the open market such that anyone who wants them can buy them and resell them at any time.

The current system is a scam. They can select exactly who gets to ride the ship to the promised land. That's completely wrong, discriminatory and evil.

Re: Ask HN: Those who've joined a friend's startup as an employee, how did that go?

#95
post #65
post #21

Earlier quoted context omitted.

That’s true to some extend. If you are still happy with it, but your friends are not, is it still a success? Not that you’d ever know of course.

I communicate with my friends. I expect them to tell me things like this.

While I'd hope a friend would call me out if they felt things were going downhill in our friendship, I wouldn't say I'd expect it. But I would definitely expect the friendship to go downhill for me too, even if from my side it just looked like an innocuous "drifting apart".

Re: Ask HN: Those who've joined a friend's startup as an employee, how did that go?

#96
As much as they'd like to otherwise, when at work, they see you as an employee. Depending on their personality, they may continue to see you as an employee when you're not at work.

So, what does a prospective employee do? You treat your employer like you'd treat any other employer. This is best for both of you. It is better that their feelings get hurt due to you, for example, negotiating a better employment agreement elsewhere than, you getting hurt because the company makes money but they take advantage of your friendship to not give you a raise or promotion. Do not let your friendship be the reason you do more work for them than you would for any other employer. This will ruin your friendship and your desire to work.

Re: Ask HN: Those who've joined a friend's startup as an employee, how did that go?

#97
I've joined a startup where I befriended everyone. It failed but we all stayed on good terms.

I also had friends join some of my projects. I didn't even offer them a salary. We were all just working for free. None of those projects succeeded financially yet (though they're all still running years later as they're low maintenance and work very well). We're still friends and chat frequently.

The key is to be fully transparent and honest about the situation and probability of success.

Re: Ask HN: Those who've joined a friend's startup as an employee, how did that go?

#98
My dad always said the only financial dealing you want with a friends is who and how is the evening bar bill going to be paid. That advice has helped me not ruin long running friendships.

I will most likely never work for a friend's startup longterm, i might be willing to jump in for a weekend(as a sort of chatgpt or rubber duck that gives advice) as a way to earn some extra pocket cash in a off the paper kind of deal. Or a really short period to bridge a time between jobs or gigs. But fulltime long term on contract no thanks.

Re: Ask HN: Those who've joined a friend's startup as an employee, how did that go?

#99

Earlier quoted context omitted.

Executive don't take risks, they make bets... It's more money, but less risk.

Good luck telling that to founders that have dumped their life savings and years of their life into their company.

[deleted]

Re: Ask HN: Those who've joined a friend's startup as an employee, how did that go?

#100
hello,

maybe slightly o.T. but at least somewhat related:

i never joined startups of "real" friends, but multiple times of more or less well known persons - lets call it "friends of friends", colleagues from the university or acquaintances, referrals by friends etc.

maybe one remark: i was never a "classical employee" always worked with the people on contracts/self-employed and at a very early stage ... (less than 5 people).

it worked out well every time, but we were never that close to begin with ... either it stayed that way or we developed some kind of a friendship over time.

just my 0.02€

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