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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?

#261

The saying (I paraphrase), "a good business relationship can be a the foundation for a later friendship, but a friendship is a terrible foundation for a good business relationship" is true in my experience.

Why is this? I find it counterintuitive. I would've thought that friendship gets you trust, that's useful in business.

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

#262
post #205

Earlier quoted context omitted.

> 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. I don't under…

You can't simultaneously have an open market for shares and highly regulated financial duties that protect investors. It would be better if there were options for employees to cash out part of equity in intermediate rounds and there are upsides to having more tradeable companies but the downside are most of these companies are near-scam like in terms of success rate and you want substantial bars to protect people whe…

Possibly worse, by removing the freedom to do business with partners of one’s choice, you would obliterate the justification for the “charging order” which would result in the loss of your business’ assets the moment part of its ownership passed to a debtor. Now in addition to the pension funds going under, all the businesses go too.

Is GP sure they are imagineering solutions, and not much larger problems?

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

#263

I joined a friend's startup, it was five academics and me (I have an industry background). There were a few disagreements about the approach, I found the academics didn't have much experience about how to market a product, it led to creating a few products with insufficient feedback, and they failed when released (we couldn't find anyone to buy them, the prospective customers we had talked to and had said "yeah sure…

Just so I don't just mention the negative, I tried to start a company with another friend two more times, it didn't go well each time because of various understandable reasons on both sides. I've now joined another startup this friend has founded, which is doing very well (we're at 200 people now) and it's one of the best jobs I've had. It's definitely not all negative, but it's like any relationship. If you don't ch…

Doing a small project together before you commit is a good idea for all cofounders, in my opinion.

If it doesn't work when almost nothing is at stake, it won't work when there's more at stake.

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

#264
I just left a gig like this after two and half years (a leadership role at a 1-10 stage startup), and I have to say it was a overall a net positive experience for me.

NGL it took time to get used to it. Being an ex-founder, it was doubly difficult as not only did I have less agency than I was used to (and frankly expected), I was also no longer on an equal footing to my friend. This led to some friction and disagreements of how things should be done, but at the end of the day, it came down to perspective differences as a founder and as an employee, and I learned to make with peace with the fact it was his company, and not mine.

In retrospect, I think the fact that we were friends first, and had spoken a lot as fellow founders beforehand, made it harder to align expectations in this dynamic. Thankfully, we parted on good terms, and I'm still helping them out as a consultant, which feels like a nice middle ground for me.

That said, I'm not looking to jump back into something like this anytime soon.

If I do however, I would definitely go into any future engagement with more tempered expectations of what I'm there to for, and what I want out of it.

As obvious as it sounds, a lot of things can be taken for granted due to the prior relationship (on both sides), and its important to lay out as much of your thoughts and expectations upfront, so that there is as little ambiguity and misunderstandings down the line. No detail is too trivial, especially around compensation, and its important to recognize and remember that you're there to do a job, not just helping out a friend, which is how the conversation usually starts.

This whole thing has taught me a lot about handling that balance, and a lot more about myself as well.

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

#265

Earlier quoted context omitted.

> 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.

Certainly, if the loss means you encounter financial hardship, you'd be understandably resentful. But even when the loss causes little financial hardship, it could put a strain on a relationship. Imagine you invest $20k in my business and I buy a $5k industrial juicing machine for the office so my staff can have freshly squeezed orange juice. I tell you that employees expect free luxury food these days and it'll make…

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

#266
post #102

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.

"travel together" You do that as equals. Working for someone means, you are no longer equals and money is involved in that hierachy. Very different situation and in most cases I would strongly advise against it.

Arguably working as equals is harder, consensus is harder than dictatorship.

I think travel requires enough conflict resolution that it will expose at least some of the dynamics that might show up in a work environment.

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

#267

Earlier quoted context omitted.

> In mu experience, people don't want equity as much as they want a living wage. They want a proper salary, every month, not some mythical payday in the future. People also don't want to be screwed over by their friends. A little equity costs the startup's founders very little, while making sure their friends see some benefit from a successful exit is worth a lot to those friends.

The concept of 'screwed over' usually boils down to a misunderstanding. If I hire a friend, then the transaction is simple - do the work, get a salary. Whether the business does well, or badly, is irrelevant. How much I do, or don't, take home is irrelevant. There's no "fairness" in play here, it's a simple business transaction. If you can't live with that then don't take the job. Join as a founder, or go start your…

If they are actually your friend, why are you not looking out for their best interests?

Whenever this topic comes up I always feel like I'm in some weird Silicon Valley Twilight Zone where "friendship" is some sort of code for "people I have access to exploit when necessary"...

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

#268

Earlier quoted context omitted.

They mean it was established by the CEO's experience with him as an engineer. To the company it was never, and as high a recommendation as the CEO would be; most people would agree they did the right thing. Unless you're hired before a hiring manager or whomever is doing the hiring you should follow the process. If you treat it like a joke because you feel entitled by your connections then be willing to accept the ou…

You are describing the HR person's ego trip. That person should be fired, for being unprofessional and for inability to adapt to a trivial non-standard situation ("normally we test the applicant's technical competency with a take-home test; now it already has been established; so I need to stop wasting everybody's time and spend my time doing something actually useful".) Obviously, HR could still be useful in establi…

I think the fundamental difference is just that you think that the technical competency has been established, and the hiring manager did not. Given the candidate did the exercise, but did it badly, I think the hiring manager was right.

None of the other stuff you're saying is relevant. No point doing armchair psychoanalysis.

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

#269
post #204

Earlier quoted context omitted.

Wow. $20k seems like a paltry sum to end a friendship over.

This forum is so out of touch with reality sometimes I'm just left blinking and shaking my head. 20,000 dollars is an enormous amount of money to a supermajority of people in the developed world. Almost half an annual wage for most industrial workers in the EU and US.

thou, the question is, wheather you can buy a friendship with the money. the answer is probably, no, hence it's not worth it.

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

#270

Earlier quoted context omitted.

The concept of 'screwed over' usually boils down to a misunderstanding. If I hire a friend, then the transaction is simple - do the work, get a salary. Whether the business does well, or badly, is irrelevant. How much I do, or don't, take home is irrelevant. There's no "fairness" in play here, it's a simple business transaction. If you can't live with that then don't take the job. Join as a founder, or go start your…

If they are actually your friend, why are you not looking out for their best interests? Whenever this topic comes up I always feel like I'm in some weird Silicon Valley Twilight Zone where "friendship" is some sort of code for "people I have access to exploit when necessary"...

In 99% of cases it's safe to say it's not in their best interest to join your startup :)

Of course, friend or not, all you have to be, to not be exploitive is to agree on a salary, and pay it.

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