I didn't had shares in the new one. The deal was to come and help as a contractor first, and then make a holding for the companies (other were involved).

But cash wasn't flowing and I soon worked for "free" as I wanted it to rise (my other company still paying me), and the cash promise at the end was very interesting. And at the end they kicked me out.

I know I made mistakes continuing doing this, but we were friends for decades so I didn't see it coming.

Note that it was not in the startup world, but I told this story because of the friendship side.

And about the shares of our first company, he basically give them to me, as he wanted to get rid of them very fast. In fact all the paperwork was done (and dated a month before).

The reason I signed them is that I too wanted to buy them back, but was a bit scared of the amount he would ask for it.

So in the end there is a positive thing.