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

So if I was looking for someone who would build a company with me, someone who would take on an entrepreneurial role, provide expertise, labour or personal connections, I wouldn't be allowed to do that. I wouldn't be allowed to give shares to employees in exchange for labour either. Nor would there be any family businesses.

>Nobody's Labour ever makes a difference. The success of any project is all about capital, political leverage and media exposure. Let's be honest here.

Capital is a factor that leverages and buys labour. Without labour the result of this equation is always zero. Without a product or service you have no customers, regardless of how much free media coverage you may be getting (for whatever reason).

>My strategy would be to only invest in small or medium-sized companies whose founders I can trust and who can manage their risk.

Good luck with that. Personal trust is not a replacement for limited liability though, especially not if shares are publicly traded.

How would a creditor decide how much to lend to a company if the personal assets of all shareholders are used as collateral?

If I owned shares in Microsoft, would I have to provide a payslip and a bank statement to Microsoft's bank? Would they do a credit check? And if I sold my shares, would Microsoft have to pay back part of a bank loan if the buyer's net worth was less than mine?

I don't think you have thought this through.

Lots of people don't want to admit that their business model or ideas are bad, they lack the skills to be a good leader, they have too much on their plate otherwise, or that they are just generally too immature to handle serious responsibility.

That said, I had a decent experience at a startup while I was wrapping up my bachelor's degree. It wasn't always perfect, but no harm was done when some other people and I eventually left. The business was sold off years later. We helped build each other's careers and are all doing great now and still keep in touch.

Things are what you make them. We didn't exactly strike it rich, but didn't expect to either. Having the right expectations is key. I would do it again with the same or similar people and if the details made sense.

We still separate work and personal life and it works out for me.

Lots of people who don’t want to mix money and friendship in this thread — while I understand where you are coming from it never was a problem for me. With loans I just loan as much money as I would also be willing to give as a gift. I guess everyone handles friendship differently though.

Joining my "friend's" startup, I hoped to use my experience and connections to guide and support the team. My friend, twenty years my junior and someone I'd previously mentored, was leading the venture. He and his business partner left University, and had the dream of forming a silicon valley company. They spent several years grinding away at this dream, and fair play to them, managed to raise millions on the back of a very weak idea. They were now ready to build a team and start developing the product. They had never been an employee as such (unless you count working in McDonalds), and had no idea how to run a company. I was excited to help them, and to see if I could help them avoid the mistakes I'd made in my career. These lads were much maligned and laughed at - they were seen as a joke by many, and I didn't like that. I wanted them to win.

Despite witnessing some concerning behavior early on.... - He gatecrashed a christmas party I attended and made a scene by dry humping me from behind, and loudly proclaiming to everyone that I was 'his bitch' - I chose to join out of loyalty and optimism.

The job quickly turned sour. As CTO, his performance was far from what I expected. He was not only ill-equipped for the technical demands of the role but also struggled with the emotional and ethical aspects of leadership. His approach to technology was chaotic and misguided, often leading us down problematic paths. There was a particularly serious incident which I won't go into, but he refused to acknowledge how serious it was.

The work environment became increasingly difficult. His emotional outbursts, lack of accountability, and poor decision-making created a toxic atmosphere. When my colleagues and I attempted to intervene or suggest strategic changes, we were met with resistance and eventually dismissed for not being a good 'fit'.

Even though the company eventually pivotted towards our advice, the damage was done. The leadership remained a disaster. Their dev turnover is high. If people aren't fired they quit.

This whole mess taught me one thing: while I’d still consider working with a friend, it has to be someone I deeply respect and trust. Someone competent, with integrity, not a power-drunk disaster like this. Never again will I make the mistake of mixing business with misplaced loyalty.