I left "big corporate" after 8 years (AWS, VMware) of which last 2 as executive/VP, to join a young startup as CTO, and then founding my own company as CEO. Both experiences have been extremely challenging and/or disappointing, for multiple reasons.
The startup I joined as CTO was a total disaster, despite a big series A and two seasoned serial entrepreneurs as founders, and it failed few months after I left.
Running my own company (with two co-founders) was incredibly tough, and we had to endure "crypto-winter" because what we were building was crypto-related (but no-BS, trust me on this). Thankfully, a year after I stepped down, the company seem to be on a promising track.
All in all, I "lost" millions of dollars in opportunity costs (VP total comp in Bay area is easily between 400/500k and 1M per year gross, all included), and having that extra money right now would have been useful for "peace of mind". But at least I tried to do things that I thought were interesting.
My humble suggestion is: make sure that if you quit your personal wealth situation is so good that if the new thing is not going to turn out great, you're still going to be ok.
Also, try to analyze in depth what it is that you don't like about your corporate job. In hindsight, I know that AWS or VMware were not the right type of environment for me (not in general; just the specific teams I was part of) going forward, but I would have probably thrived in a smaller company as CTO or similar.
Right now I'm an operating partner at a VC firm, I really like it (I think the specific VC firm I deal with is outstanding, compared to the average, in my experience), and things seem to be going ok.
Hope this was helpful. Not easy to share personal stuff, especially when it's about a tough period in life. (disclaimer: all is relative; first world problems; etc).
The startup I joined as CTO was a total disaster, despite a big series A and two seasoned serial entrepreneurs as founders, and it failed few months after I left.
Running my own company (with two co-founders) was incredibly tough, and we had to endure "crypto-winter" because what we were building was crypto-related (but no-BS, trust me on this). Thankfully, a year after I stepped down, the company seem to be on a promising track.
All in all, I "lost" millions of dollars in opportunity costs (VP total comp in Bay area is easily between 400/500k and 1M per year gross, all included), and having that extra money right now would have been useful for "peace of mind". But at least I tried to do things that I thought were interesting.
My humble suggestion is: make sure that if you quit your personal wealth situation is so good that if the new thing is not going to turn out great, you're still going to be ok.
Also, try to analyze in depth what it is that you don't like about your corporate job. In hindsight, I know that AWS or VMware were not the right type of environment for me (not in general; just the specific teams I was part of) going forward, but I would have probably thrived in a smaller company as CTO or similar.
Right now I'm an operating partner at a VC firm, I really like it (I think the specific VC firm I deal with is outstanding, compared to the average, in my experience), and things seem to be going ok.
Hope this was helpful. Not easy to share personal stuff, especially when it's about a tough period in life. (disclaimer: all is relative; first world problems; etc).