When you first walk into the startup space, you generally see two kinds of success.

  • Successful founder who built a company and took it to IPO.

  • Successful investor who was an early investor in Uber, Door Dash, etc.

But being in this space for about a year, I've realized that success is not binary, going beyond successful founders and investors.

Can you tell me the name of the person who was employee #5 at NVIDIA?

Can you tell me the name of the person who was employee #11 at Stripe and stayed with the company until they had 5000+ employees?

Probably not, but these people are probably wealthy and successful in some capacity.

If the goal is financial success and freedom, the founder/investor route is not the only way to do it. It could arguably be disadvantageous to financial success depending on where one starts.

But if the goal is the pursuing “entrepreneurship“, “working for yourself“, “being in charge“, etc, being a founder is the only way to go.

I can see how people’s perception of success can change over time in this space.

The truth is that, it’s extremely difficult to make it startups. People have heard that many times, but it genuinely is extremely difficult. And, the people that recognize that and want to stay in the space, generally end up working for a startup or going an adjacent route. But that doesn’t mean they won’t be a founder/investor. And that doesn’t mean they won’t be successful.

An interesting observation, working in startup/VC land for a year, is seeing how many variations of success there are:

  • Exited founder building another company

  • Exited founder working at a startup

  • Late stage employee becoming an early employee

  • Career employees building their first company in 40-50s

  • Startup employee turned VC

  • VC turned founder

  • Career VCs that make it big

And more.

And these profiles mix in having kids, taking care of parents, etc which make it even more impressive.

Walking into VC/startups, I thought there were two ways to win.

A year in, I've lost count of how many there actually are.

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