I just got off the ride (at a small startup) after ~9 years. Not much to show for it economically, but I did gain a lot of confidence and experience around how to actually run a business. I've picked up a lot of lessons, most in what not to do. I'd say it was absolutely worth it compared to alternative paths that I was previously on.
My biggest takeaway is to focus on compelling problems, rather than delusions of financial grandeur. I've learned that solving a hard thing and hearing the feedback from the customer brings me a lot more joy than hypothetical promises of extra cash in the bank. The money is a mind killer for me, especially when it's not real yet. Stock options are no longer something that interest me. I'll negotiate additional salary instead. The only company with stock options I am interested in would be a company that I personally found and retain control over.
One other lesson is to pull the rip cord the microsecond you think something doesn't feel right with management/leadership. I started thinking things like "does anyone care about the sales funnel?", "Why are we only talking to one prospect at a time!?", etc... The chances you will be able to "fix" some other person in this setting are pretty much zero, unless they actively want to be helped. I feel like I could have jumped off this ride at the ~7 year mark and walked away with 99% of the wisdom I have right now.
My biggest takeaway is to focus on compelling problems, rather than delusions of financial grandeur. I've learned that solving a hard thing and hearing the feedback from the customer brings me a lot more joy than hypothetical promises of extra cash in the bank. The money is a mind killer for me, especially when it's not real yet. Stock options are no longer something that interest me. I'll negotiate additional salary instead. The only company with stock options I am interested in would be a company that I personally found and retain control over.
One other lesson is to pull the rip cord the microsecond you think something doesn't feel right with management/leadership. I started thinking things like "does anyone care about the sales funnel?", "Why are we only talking to one prospect at a time!?", etc... The chances you will be able to "fix" some other person in this setting are pretty much zero, unless they actively want to be helped. I feel like I could have jumped off this ride at the ~7 year mark and walked away with 99% of the wisdom I have right now.