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Ask HN: Leaving post acquisition?

My cofounder and I recently sold our small startup after grinding it out for a couple years. Given we were a small player in our market, it amounted to an HR hire. I wound up with basic salary, benefits and some options (which are unvested.)

I'm also just sort of burnt out on the idea and ready to make a change. I was freelancing and making considerably more money prior to starting the company and I'm considering this once again.

My cofounder has no idea I'm considering this. I don't want to cause a panic by disclosing I'm thinking of leaving but I'm wondering if others have been in a similar situation and how they handled it.

Am I crazy? What's the right amount of notice? Is it best to tell my cofounder now even though I don't have anything lined up?

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When you say it amounted to an HR hire, did you cash out at all?

If not, and the options are unvested, then it is just a job - you didn't receive anything the day you came onboard that someone off the street could not have negotiated.

Unfortunately, your cofounder is no longer a cofounder, but a coworker. The reason for advance notice would be the same as in any other workplace (i.e. a personal relationship) as would be the notification expectations to your new employer.

The unvested options exist only to place a value on your leaving. If they are not worth as much to you as leaving, then there's nothing wrong with going - and if people are going to be pissed, they'll be pissed anyway. The sort of people you want to work for are those who value your longterm happiness more than your warm body filling a production schedule.

Good luck.

[edit: I'll add that if you didn't cash out somewhat, that was a really dumb strategy by the acquiring company because it did not give you any immediate benefit for having ground it out all those years]

Hi, I did not cash out at all on closing. The original salary offer was considerably below market (and well, well below what I was making before) so this started things out on the wrong foot IMO. The only relationship I care about is with my cofounder at this point.

I do not think you are crazy at all... you were freelance and started the company because you like that sort of thing, presumably, and now that it is more stolid it does not have any appeal. It happens a lot.

That said you will want to handle this professionally so that you do not burn any bridges. You have sold one company and may want to do it again so you will need a reference there.

I remember reading that when Jim Clark wanted to leave SGI (prior to founding Netscape) he spent about 6 months working it out. Obviously your situation is different but you may want to pickup his book Netscape Time and read the sections on his exit from Silicon Graphics to see if there is any advice there that you can use.

Thanks. Some freelancing opps have presented themselves sooner than I expected. I feel like if I leave right now (even with 3 weeks notice) people will still be pissed. I'm just nervous to say "hey, i'm going to start looking for a job" before I actually have one though.

Thanks for the book rec. I will check it out.

If they don't pay for you to stay, don't

I think you should focus on the relationship with your founder. Finding people you can work with is rare. It's actually very difficult.

Have a honest face to face talk with your cofounder. Have you read "crucial conversations"? It's $10 on amazon. Download it and read it. Then sit and talk with your founder. The book will help you communicate in a way that doesn't screw up your relationship. He might be feeling the same way.

The book is paramount though. It really does make difficult conversations easier on both parties even if only one as read the book!

I think a good rule of thumb is lay your intentions out there ASAP, and give the company (and your co-founder) the time it needs to adjust to your departure, within reason.

At the end of the day, this is about you. If you're leaving to do something that will make you happy, no one with sense can hold that against you.

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