I built the first Android Twitter client, sold that to Idealab* and given our huge market share (~40% IIRC ) pitched them the idea to build our own Twitter clone in order to move those users over. Twitter took notice and locked all our apps which eventually kicked off the anti-third-party tendency that we see today. Good times.
Another time I turned my private news aggregator into a public service (Popurls) which kicked off thousands of clones and was at one time the number one traffic referrer to Digg and Reddit. A year later Guy Kawasaki cloned it, and I find myself invited to a Ramen lunch with Kevin Kelly who blogged about it as being his favorite website. 15 years later, I got funding from Mark Cuban for building a successor. All from a private solo side project that started as a 20-line Perl script.
I'm not the person you're responding too but I thought I'd mention some of mine. I wrote a blog post called "How to Lose Money With 25 Years of Failed Businesses" where I discuss some of the little side hustles I've managed to kill over the years.
Besides maximising luck, the only real strategy I follow is buy low, sell high in a sense of keeping the burn low and counting on a win every 3-4 years that will create enough cash to finance the next period of failures — because what got you here won't get you there ...
