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Going to throw cold water on all the advice here. I am serial startup CTO with a variety of outcomes. I never made a billion but I had enough successful exits and careful investments that after 20 years I am comfortable (still hoping for the lottery outcome though).

I was very naive for a long time about the realities of the world, as I currently see them. There is a wealthy and connected class that exists in the world. There is not some secret cabal that controls who’s in and who’s out, but rather relationships and reputation and references. Having a good family is a very strong signal - a parent who runs a company, a parent who’s a billionaire, a background that can give you legitimacy. As a “new man” you can become part of this class through guile and wit and success, but you are operating on hard mode.

A lot of people in the money class by birth (which are most of them) are not inherently successful. But their connections open so many doors.

The entrepreneur I have hitched my horse to, which has assembled a trusted team of executives and VPs, is part of this class in addition to already being worth tens of millions from successful exits. He is hungry beyond all belief and desires to be a billionaire, and he is quite skilled and hard working despite being born into low-tier wealthy family. His ability to get calls with the rich and successful is absurd. He wanted to speak with Mark Cuban and he got him on the phone to pitch him within days - just one example where I am name dropping someone to illustrate the type of things he can do. He has an encyclopedic knowledge of who knows who, who owns this business and who made this thing, he also knows various people in entertainment and the arts and gets them to vouch and rep his various interests. A famous pop musician tweeted one of his ventures as a favor and drove a lot of users. He networks like you won’t believe and owns property in NYC, LA, Miami, and jet sets around the US / Europe / Dubai as needed for business.

I am pretty sure my children will be similar to how he started in terms of connections based upon my help and the school I send them to. However I started very low in society and used technology skills and hard work as the mechanism to elevate myself and hustle to get to the place I am now.

As tech people on HN we value ourselves so much. Yes we have a lot of skills and are necessary and provide value. But guys like my CEO are key to succeeding in business and without him I couldn’t do my job and succeed in the way I want.

Who you know runs the world. As the technical cofounder we are not the deal makers nor the money people, who truly have the value and upper hand. I’m not trying to depress you, nor say you can’t do it without someone like this. But once you start really seeing how the 90% case works - how this company gets follow on money despite inferior product because some VC owes a favor, how this company gets acquired for more than it’s worth because of some friendly connection, why this company gets a seed easily and yours can’t get anything despite traction. It’s just how stuff works.



A lot of honesty here. I can't help but point out the spiritual hole this upbringing can leave on children. Parents who prioritize networking and building relationships with the rich and successful show a poor example to their children that need to learn important lessons like compassion, inherent human value, altruism, generosity, etc. It's like teaching them the opposite of the story of the "Good Samaritan"


Who says you can't have both?

I met someone who was as humble as apple pie, training to become a cancer surgeon. Seeing her, you couldn't have guessed that she was descended from some of the erstwhile most powerful nobility in Europe (including relations to a bunch of royalty today). But then again, while she got that far through a lot of merit on her own terms, she was amply supported in many ways by coming from a very wealthy background (eg: no need to work part time to support herself unlike most college kids, visit home very often, etc).




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