Jose – agree with your comment. The private security markets for founders are a good option to get some liquidity and take some chips of the table. However, the liquidity might be limited vs. the public markets for larger stakes and valuations could be lower. Regarding the VCs I agree that the pressure to IPO will definitely be coming mainly from their side.
John – interesting post. I liked the way you approached the topic and I agree that by having the following 3 attitudes you will most likely run into problems. One question that kept coming back to me is your third point about structure and more specifically about your advice regarding not changing the structure that often. For some rapidly growing and constantly changing startups I believe that a continually changing structure might be needed in order to keep pace with the life cycle of the company and the current / near term needs. It might be the case that not changing the structure rapidly enough might end up destroying significant value and lost market opportunities.
Interesting post and I agree with most of the points you raised.
However, I think another key factor that all these successful companies have in common is that they were created by Paypal mafia Founders as their 2nd, 3rd of 4th startup. In a sense, they had already been very successful in a previous venture and had the knowledge and experience to better know which skills and type of people they needed in their team. In doing so, they had the benefit of better identifying and building a team of ‘like minded people’
This situation would be different for a first-time entrepreneur