I feel like an even bigger lesson has been missed here. I am not and have never been a CEO but I run a small business and work as a contractor so in a sense I have some experience with these issues. The CEO across from you was a blowhard and because of that he is a person who is easily manipulated. In the end he will likely fall.
However, there is a difference between selling somebody something or negotiating and being mindful and aware of your and your team’s capabilities. Fake it until you make it is not necessarily a problem. The problem really is that people have a tendency to believe the lies that they tell others. Such as “I can get that done in a week with my current team.” Or “I have enough coding experience to do that myself.” Or, “I have done all the due diligence necessary.” The biggest mistakes I have seen leaders make is that they will build a narrative that allows them to sell a product or service that is possibly a stretch of the truth, but after repeating the story they begin to believe it. This is how the reality gap between a technical team and management usually forms. I feel what you’re describing here is the age old problem of hubris and self delusion.
We know that most things in life are statistical in nature. You maybe one of 14 teams, all working on a similar problem, who gets funded by a VC because of someone you knew. You then take this success to mean that you are special and better than the others, which is clearly not the case. From this early success you build this blanket of “I have the grit, determination and skill that no one else has, thats how I got here.” You may have grit and determination but you also were lucky.
People who have initial success seem to build this image of themselves that they work hard to feed. When something doesn’t go their way they then tend to lie to themselves and others because they want to maintain the feeling that they are special. We are not special, we have value in certain contexts and we try play the game so that the statistics are in our favor.
What you are talking about is being humble, which is something that most people learn at a young age. It seems to me that your description of a lack of vulnerability in silicon valley points to something else entirely. It seems that you are showing the world that some silicon valley leaders are essentially children who have yet to figure out that they are not the center of the universe and people have lives and dreams outside of theirs. Most people know that we all eventually fail and thats okay. Most people know we are all just living our lives and that there are ups and downs. Most people know what really matters is that you can provide for yourself and the ones you love, that you’re happy and that you have some sort of purpose. When I hear that people sacrificing these tenets of a good life to maintain an image, because of hubris, to me, all I feel is sad.
