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

I joined a friends startup because I was eager to jump into the startup scene and his business idea was pretty good and doing fairly well.

After about a year I started getting increasingly inappropriate texts from him, and it seemed like he was trying to cheat on his wife. Needless to say, I left, and now that friendship is over.

I went to work with a friend who was starting a new company. He had started a profitable and successful fintech startup, and was still serving a role in that company. He had the money, I had the time. I thought it was a match made in heaven.

Until I started working with him and his true colors came out. I ended up doing all the work. He would occasionally come into town, shit all over everything and leave. He was an embarrassment in almost everything I tried to involve him in. We both are sarcastic people and he couldn’t separate the personal relationship from the professional.

I got to see another side of him I never knew as friends. All of his claimed tech skills were either completely fabricated or grossly exaggerated — turns out he was only good at having others do the work for him, while extracting the best possible deal for himself.

When I exhausted all of my personal savings, as well as spent substantial amounts on the startup myself, he negotiated with me to draw a salary from his investment like he was playing a game of poker. I was asking for $60k living in the Bay Area and it was like I was asking for the world. Meanwhile he would openly flaunt his wealth, buying $30k watches and taking every opportunity to brag about becoming “an investor”. He would regularly have me demo to add credibility to himself and for his own ego to his friends and personal connections related to his other business that left me asking “why did I just meet that person?”

All of the employees I recruited eventually became disgruntled and disillusioned, and were eventually fired by him (which he seemed to take great pleasure in).

The final straw was when we were accepted into an accelerator, based off all my work and connections. He agreed to do the in-person part of the accelerator with me, and he did show up for the first week. He spent it bragging about how much money he was making in his “other company” —- he even had one of his cars shipped out so he could drive it around, flaunting everywhere he went. Meanwhile our employees were constantly late being paid, and we were at risk of eviction from our office. Since I was the “technical one” (we are both software engineers) and his other company was fintech, we both agreed he should be responsible for the money but I don’t think he ever paid a bill on time and I would constantly have to remind him.

As soon as the money from the accelerator hit the bank account, he stopped paying for everything and left town with all the money, leaving the car he had shipped out sitting in the parking lot for months. I went to our investors and was advised to resign to shield myself from legal consequences. He accepted my resignation, the company failed, and we haven’t spoken since.

So. So. Poorly. The most stressful, traumatic, job I’ve ever had, the end of what might have otherwise been a lasting friendship.

Two similar situations:

- a coworker and close friend was moving into management. Went poorly. We both left within six months. We had worked incredibly well together as peers.

- I joined a startup where, unbeknownst to me, the engineer who became CTO and an early hire were best friends since college. The early hire became an engineering director. He was awful. His reports knew it. We had to humor him and stop him from making bad decisions when we could. Eventually he stopped being involved in engineering, and stuck to strategy discussions with his buddy the CTO.

That company recently made headlines for hosting image generating models fine-tuned to generate CP. The founders knew about it for months beforehand. It was their only paying customer after $100MM venture capital, so they kept with it until the news came out.

Wow that’s some selfish behaviour!