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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?

#11

Hello, this does not apply to me but I'd like to say my 2 cent regardless: Your boss cannot be your friend (or vice versa). It simply does not work out well, you can't be a leader while being friends with your followers, so I expect everyone who worked for their friends will most likely describe it as a miserable experience.

It’s the chicken or the egg kind of problem. I think it’s easier to become friends with a boss. Less easy for a friend to become your boss.

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

#12
I joined a friend's business as an employee and worked for him for years. I think for the most part that went ok but the fact that we're not friends any more probably tells you something. At some point I felt like I was being taken advantage of, left, and that sort of ruined the friendship. We weren't particularly close friends to start with and we were still on talking terms when our work relationship ended.

I also repeated my mistake (sort of) by investing in a friend's small business. When the business wasn't successful and we didn't see eye to eye on the path forward that totally killed our friendship.

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

#13
Spent 7 years working at a startup founded by friends. It put a strain on our relationship, but it's been almost 7 years since and we still all keep in touch... and Im trying to get a friend to bootstrap and idea with me now. Best advice I can give is to be honest and transparent with each other.

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

#14
post #6

Earlier quoted context omitted.

I’ve hired several friends as employees. It works fine if both of you are able to separate work from friendship. Admittedly not everyone can do this, but it worked out in my situation.

It probably did, you know your friends and I don’t, but you don’t know that it worked out. You really have no way of knowing if your friends still think of you the same post-employment even if you’re still acquainted.

A friendship isn't and shouldn't be a pickled-in-amber thing. If the friendship you have now is one you're happy with, that's a success, whether it's the same as the one you had before or not.

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

#15
While some people might say it's bad idea; truth is: lots of early stage employees in all companies are either good acquaintances or friends, or friends of friends. Simply because some trust is required on both sides. Otherwise it's hard to build skilled team to work for a company that dont offer any benefits except for equity while can go down at any moment.

IMO this is all about expectations. If you never lied to your friend about your actual experience and skillset and your friend offers reasonable compensation then it's win win situation. Working on a team of like-minded people is amazing.

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

#18
I've had mostly good experiences doing this across two startups. The biggest challenge I've seen is the awkwardness around people who have previously been peers now being stacked in a hierarchy. The best way I've found to get around this is to think about your career as a long road where roles can change e.g. "You're working for me now, but next time I may be working for you". I had a former manager and friend work for me, and there are definitely friends I would work for in a heartbeat in the future.

It will also probably be hard for your friend to deliver tough feedback to you, so you may have to work extra hard to solicit real feedback.

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

#19

Hello, this does not apply to me but I'd like to say my 2 cent regardless: Your boss cannot be your friend (or vice versa). It simply does not work out well, you can't be a leader while being friends with your followers, so I expect everyone who worked for their friends will most likely describe it as a miserable experience.

I want to add my 2 cents also and say this isn't a universal truth. I've definitely had bosses who have become friends, even whilst working together. Sometimes it feels that authority and being close in a friendly way are mutually exclusive, but I don't think they are. Good leaders maintain boundaries, set clear expectations, and don't violate them. You can do that whilst being friends, but it's not easy.

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

#20
post #19

Hello, this does not apply to me but I'd like to say my 2 cent regardless: Your boss cannot be your friend (or vice versa). It simply does not work out well, you can't be a leader while being friends with your followers, so I expect everyone who worked for their friends will most likely describe it as a miserable experience.

I want to add my 2 cents also and say this isn't a universal truth. I've definitely had bosses who have become friends, even whilst working together. Sometimes it feels that authority and being close in a friendly way are mutually exclusive, but I don't think they are. Good leaders maintain boundaries, set clear expectations, and don't violate them. You can do that whilst being friends, but it's not easy.

I hired a close friend as a direct report. It worked well, because we could both compartmentalize the different relationships at difficult moments, but could leverage the trust and ease of communication granted by a long relationship most of the time.

A decade passed and same guy is a direct report again. So far, it’s going well again.

I’ve been fortunate to never face a round of budget cuts while a close friend was reporting to me. That would be difficult to navigate, regardless of the outcome.

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