FROM CLEVELAND TO THE VALLEY 
The Silicon Valley Humble-brag: "I don't need to do this"
If the first post seemed overly glowing about the Valley and the wonderful bliss of the widespread tech immersion, this post should balance that out nicely. Once again, the disclaimer is this is my experience spending a lot of time in the SF Bay Area and now I am fully immersed and living here. This is meant to be observational for those impacted by or interested in the start-up world from the perspective of a Cleveland guy. As always, there are exceptions to the people I am writing about about in this post and I am always refreshed when I get the opportunity to interact with them.
Look at this article...it's highlighting a systemic and unfortunate reality out here that I've seen enough to call more than an outlier. The first sentence in the article..."David Sachs doesn't need to do this". Then it goes on to explain he's joining another startup for whatever non-monetary reasons because let's be very clear, he doesn't need the money or the success, he's got plenty of both under his belt. I've heard that so often in my conversations here and it's so widespread that I don't even think people realize how shallow they sound when they are cramming their wealth picture into the conversation. They must not know how insecure and self-absorbed they are when they drum on that point.
Let's say that's true, and you are joining a company or venture for reasons other than compensation requirement. What's the upside of saying that beyond what it does for your ego? Because the downside is immediate if you're trying to work or partner with the person you're proclaiming this to.
For one, you're stating that at any point in our partnership you can call or email and say ..."I don't need to do this". I'm not saying money is the motivator for everyone but it's clearly important enough for you to have to proclaim this upfront so why wouldn't it factor into your decision to bail if things get hard/tenuous?
But more damaging is the fact that when I hear this, I think it's nothing but a hedge against a future undesirable outcome. It's easier to brush off if something doesn't work by saying you don't really need this from the jump, so you didn't put your all into it and fail. You put some into it and failed and thus the failure doesn't hit as hard.
I don't actually think these are the signals most people intend to send when they are stating this, in most cases I think it's just superficial bragging. But it does send these signals on top of the fact that you are bragging, so it's a double-whammy.
Some might think it's no big deal but imagine how absurd it would be if people did this in other facets of life. Picture an extremely fit person walking up to a machine at the gym and before every set saying 'you know, I really don't need to do these pulldowns but I just like the burn'.
If I Could Respond The Way I Want To
I would tell that person that the truism remains that if you're really good (or wealthy, or smart, or capable), you don't have to tell anyone. They'll simply know. And, believe it or not, if you don't make it a point to cram it in the intro of your first meeting, more than likely you'll be asked at some point and share all about your past success. Moreover, the most profound effect you can have on someone is for them to find out later that you have infinite resources but that person never found out from you. Your humility will be noted and remembered.
It's actually a great accomplishment to be financially solvent and content enough with past accomplishments that you can work for reasons like passion, competitiveness, purpose, or even altruism. I just wish people here would leave that out of the first 5 minutes of the conversation when you first meet them.