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Good email from @TrevMcKendrick today https://www.howitactuallyworks.com/archives/in_defense_of_thinking_bigger.html - here's my Defense of Thinking (Slightly) Smaller:
In the history of many of the founders building a world-changing startup, you often find they had a smaller more "boring" success/exit that freed them from struggles of 'average person with a paycheck' and gave them significantly more optionality. Some examples 
Before becoming billionaires with @stripe, @patrickc & @collision built, Auctimatic: auction management software for small Ebay sellers, and sold it for $5m https://www.startupgrind.com/blog/the-collison-brothers-and-story-behind-the-founding-of-stripe/
Before sending rockets into space and revolutionizing the auto-industry, @elonmusk was broke building Zip2 (online city guides for newspapers) before he netted $22m on the sale: https://www.cnbc.com/2018/06/19/how-elon-musk-founded-zip2-with-his-brother-kimbal.html
Before building and selling http://Broadcast.com for $5.7b and buying the @dallasmavs, @mcuban built a system integrator and software reseller (literally called MicroSolutions) and sold it for $6m https://en.wikipedia.org/wiki/Mark_Cuban
Steve Jobs met his co-founder Woz working on a goofy business called Blue Boxes that hacked the long distance network (no exit, but still he found Woz) https://www.entrepreneur.com/article/220602
Trevor himself built and sold a Spanish language bible app, got featured on @Gimletmedia's Startup podcast, before deciding to think bigger at @LambdaSchool. It's an awesome story: https://www.businessinsider.com/atheist-makes-100000-selling-bibles-2015-2
The list goes on and on (feel free to add your own here) but there is a strong pattern of founders of truly world-changing billion-dollar startups first netting $Xm by building and selling a smaller more "boring" business that enabled them to Think Bigger.
Mike Bloomberg https://twitter.com/tylertringas/status/1277940184798109697?s=21 https://twitter.com/tylertringas/status/1277940184798109697
