Comment by rsp1984 | Hacker News Reader

Comment by rsp1984 | Hacker News Reader

If you are trying to start a startup with a friend, think about this, do you really know this person? are you confident that under high levels of pressure this person is going to help you or is he going to break apart?

I started a startup with my best friend whom I knew for several years. The startup succeeded (kind of, we got acqui-hired by BigTech) but the friendship turned into a deep alienation in the process.

Startup pressure can bring out the true character of a person. The problem though is that you may not know the true character of someone until startup pressure is applied -- even if that someone is your best friend.

I'd actually argue for not starting your startup with a good friend. Friendship bias works against you when your cofounder turns against you under pressure. Instead choose a co-founder that you know professionally and that you have a good gut feeling about.

The problem of the story presented is not that he didn't start the company with someone he knew better, it's that apparently no agreements existed that prevented $ANTISOCIAL_COFOUNDER_BEHAVIOR from happening. I'm certainly guilty of that as well. The resources spent on setting up those agreements are always worth it. Also not a shame at all to bring in lawyers at this stage.

It is super common to divide shares generously the first day of the startup, it's like marrying a girl the first day you know her. Isn't it creepy?

It's common to divide 50/50, but with a vesting schedule. If co-founder shows $ANTISOCIAL_COFOUNDER_BEHAVIOR despite agreements made you may kick him/her out and will only lose shares that vested.

> Startup pressure can bring out the true character of a person

Not necessarily. It can bring out the worse.

Let's say you are stressing a machine beyond its limit. The risks are specified in the manual but you still do it. The resulting mechanical damage can't be blamed on the manufacturer.

So well put. People you could have roomed with, drink with, hung out with, even been trapepd on a desert island with, all successfully, can turn into monsters under the pressure of running out of money and associated startup events. And you can find yourself echoing that behaviour.

My experience is the reverse: I started a company with my 10+ years best friend, and it has been great. We even hauled another friend on board (he bought some shares, but we still have most of them).

Most people I know complain that they don't see enough of their friends due to increasing family commitments, but I'm spending most of my working time in the office having fun with my best friends. It's absolutely great and all the shared experiences also nurture the friendship.

I guess it all boils down to being really really honest about your assessment of each other's character. I couldn't have done it with most of my other friends. We also wrote out rules up front about all kinds of possible issues and determined who would arbitrate, so that we would have clarity before everyone is entrenched in a POV that coincides with their interest.

And our #1 rule is: if anything bothers you, you have to be explicit about it or accept your grievances will be ignored.

I started a company and brought on a best friend about 2.5 years in. It was a terrible and costly mistake. The business continues to thrive, but our growth was considerably stunted for the year he was on board.

I have a few theories for why it didn't work. I think it comes down to an expectation that, as a friend, normal work rules do not apply. This friend thought they could work on whatever was interesting (rather than what their job called for), and could flake or complain as a friend.

Perhaps a more domineering personality than myself could crack-the-whip and force a person into their role, but then what's the point of the person being a friend? And is that a good use of a founder's time and energy? Arguing with and controlling a friend/employee? Nope.

I have had much better luck hiring people I don't know and becoming their friend through work.

"Startup pressure can bring out the true character of a person. The problem though is that you may not know the true character of someone until startup pressure is applied -- even if that someone is your best friend."

This is true enough, but it need not be 'startup pressure' that reveals character. Many life situations can apply the same or greater quantum of pressure. So if you are going to do stressful startups with a friend, see if you have gone through hell before and come out on the other side still friends.

Tangentially life crises are very revealing of who your true friends are. Likewise romantic partners. When you are going through hell, just look around to see who is still there, and who ran for the hills.

I had a similar experience, unfortunately. Call it pressure to establish, call it stress... the friendship was ruined. Thankfully, we did not even start, but we were about to.

I would also argue that starting with a distant family member is also not ideal.

I dunno about true character, maybe levels of maturity. Learning patience and dealing with stress comes with age. Anyone can do it.

Can someone with historical experience starting a company with both a friend and a nonfriend comment about this?

We get a lot of advice (e.g. pg) to start a company with friends, but we also get a lot of comments one way or the other, but without personal experience in both.

Can someone who have been on both sides talk about it? I certainly have not been on both sides.

Contrary to the advice which is out there I believe the focus shouldn't be on friend or none-friend, but the 'person' and the 'relationship'. Being a founder is incredibly stressful, so you need to find someone who's got your back. In my case, it's my brother because I wouldn't trust anyone else with it, besides our parents.

Gimlet Media had their "Startup Podcast" and in one episode they fretted about hiring the boss's wife. The advice he got was if she's qualified he should do it.

https://www.gimletmedia.com/startup/15-married-to-your-busin...

Sometimes the friendship is worth preserving in favor of going into business with someone else that if you lose, no big deal.

I started a small real estate business and asked my friend of 15 years to invest with me. He did sight unseen because he was a friend. I didn't know what I was doing. I made some horrible rookie mistakes. Even though we were suppose to be partners, I voluntarily took the hit on the loss and made him whole so he didn't lose any money. Our friendship was more than worth the loss. He trusted me and keeping our friendship was worth every penny.

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