I'm a little older than probably the average HN visitor, but I bet my experience matches a lot of peoples: Mid 90's startup: Sold company, proceeds company cov

I'm a little older than probably the average HN visitor, but I bet my experience matches a lot of peoples: Mid 90's startup: Sold company, proceeds company covered debt, basically. I learned a ton on those 2.5 years, but had to have a part time job to make ends meet (and I was not living a lavish lifestyle). Late 90's - Mid- 00's: Partner in consultancy that made generational wealth for at least one client, worked to burnout multiple times, never able to use the consultancy to develop a product with ARR. Made good profit share and salary the years prior to dotcom bust. Company was sold for basically the debt on the line of credit. Mid-00's - Mid twenty-teens: Joined a "startup" that was really a consultancy. Spearheaded substantial growth, Shareholders just increased the dividend amount every time company grew year over year. Unable to negotiate an equity position that aligned incentives (me giving up my life and energy to further build the business) so I left. I was forced to surrender the equity in another startup when I quit the first one. The other start up is limping along, I think losing a (manageable) amount of money annually. I never valued this equity because the shareholder group was the same as the parent company, so this one had the same issues. So I guess in a 25 year period I had something like 2-3 exits. I worked more than full time between 1998-2015. I'm now a firm believer in that a successful exit takes knowing the right people and getting lucky.