> (looking back) would have done better financially and felt better about it had I pursued my own path (entrepreneurship) Perhaps just normal regret from perfe

> (looking back) would have done better financially and felt better about it had I pursued my own path (entrepreneurship) Perhaps just normal regret from perfect hindsight? I believe doing a startup was easier in the past than now because there were more opportunities and less competition. Now a software startup is more likely to be in a crowded market - or if you do find a unique niche others will quickly copy? Still plenty of opportunities but maybe start in a niche? > > I missed opportunities to become truly expert by taking on new roles. Great technical skills in narrow areas are not that useful in a founder. Jumping in the deep end and soft-skills and solving problems without help are more useful: and your career sounds like you got more of that. I suspect your career path has left you with a far better ability to found a startup than you think. The only block is that we get conditioned to working in a large company and changing gears is hard. If you had the personality to succeed in a startup, you can still do so. Maybe unwanted advice and I've only really had experience in my own startup so perhaps not helpful! I would also suggest avoiding VC - VCs select for certain types of failure that you don't want. Also you will always lose (extremely assymetrical game with long term players - the field and rules are also biased).