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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?

#191
I have zero experience, but a few thoughts nonetheless that I'd like pushback on. I believe there are at least two major categories here

1. They are more of a business/school friend. You share knowledge and passion. You compliment each other's strengths and cover each other's weaknesses. There is little risk to forming a mutual business partnership, since loosing such a friend is part of the game.

2. You were meant for each other, perhaps you are even married. This venture will make you even more entangled, increasing risk but also reward to your relationship.

Be VERY sure if you choose #2. Strongly consider whether your relationship can handle the added risk of loosing the business and consider when it's time to walk away from the business (despite the financial consequences) in order to save your "marriage". In my marriage we've made bad financial decisions (wrong house purchase) where walking away cost us 100k but I think definitely saved the marriage. Loosing that money was worth every penny.

For #1 it's more of a straightforward business decision.

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

#192
post #172

One of my favorite quotes is attributed to Saint Augustine: "If two friends ask you to judge a dispute, don't accept, because you will lose one friend; on the other hand, if two strangers come with the same request, accept, because you will gain one friend." It sort of applies, here, as well.

If two friends ask you to judge a dispute, and you don't accept... You might loose two friends since both of them think they are right and will not understand you do not support them.

That would be a mildly weird reaction to "I don't want to get involved in your dispute", in _most_ cases. (I think there are edge-cases where not wanting to get involved might in itself be taking a stand, but certainly for everyday disputes most people wouldn't take offence to "I don't want to get involved").

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

#193

Earlier quoted context omitted.

> As it was it left me scrambling with three small kids. you did not mention whether this early termination was communicated beforehand. nevertheless this person probably never was your friend. sry

> nevertheless this person probably never was your friend. sry No, it's completely common for friendships to break down over business. Very few friendships are robust enough to survive one party costing the other $20,000.

> Very few friendships are robust enough to survive one party costing the other $20,000.

That probably depends on how critical that $20k is to you. If it's your only $20k, then yeah it'd be much more impactful than if it's just one of many.

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

#194

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 dea…

your dad dispensed some great game

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

#196
Lots of people like to talk about the downside risk of losing friends when things go south. What most people don't realize is that when the business does well, you risk your friends becoming just business partners. You lose that impartial party in your life you can talk to about anything and realize you and your friends now only talk about business.

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

#197

Didn’t end up going to work for the friend, but the situation still strained the friendship. An engineer I worked with for several years (and became friends with outside of work) started his own company, a couple of years later he recruited me to join as his business was taking off. He’d also brought in a business guy who seemed to put in lots of processes including a mandatory take-home coding assignment as part of…

[deleted]

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

#199
post #104

There's an old aphorism that goes something like "don't get loans from family". I consider people worth calling friends to be similar to family. I also don't have close family connections at that level. Guess that means I put more importance on friendship. I've had the experience one time of cofounding a company with a friend. It didn't end badly, but it wasn't ideal. I realized pretty quickly I was going to be solel…

Another one - if you want to lose a friend, lend him/her some money

But as Jack Handy said, if you loan someone $100 and never see them again, it was probably worth it.

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

#200
I joined as employeee #1 as a friend of a friend (we were friendly acquaintances for a year or two before). I think the relationship helped get us to a good working rhythm right away, but as many founders do he had slightly misrepresented some facts about how far along the company was and was slightly greedy with equity, so I left about 6 months in when factoring the newfound facts into the expected value equation showed me that I'd be better off back on a regular W2. It's been 4 years and the company is still around, but as I expected it's quite a bit behind where it would need to be for my personal economics to have made sense (and that's still assuming an exit that may not come). Our relationship has cooled a bit but remains friendly, I happily served as a reference/expert on a customer call and wish the best for the company.
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