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4/ After many years, I figured out how to run my lifestyle business as easily as I could play a game like SimCity, I asked myself what I wanted to do with my newfound abundance of free time. And it turned out that what I really wanted to do with my free time was work more.
5/ The paradox of a 4HWW/lifestyle business is that most people who successfully start one actually love to work. Instead of optimizing for free time, I realized I should have been optimizing for what I really wanted: to work on hard problems with as many smart people as possible
6/ A VC-backed startup was the right answer for me for many reasons, but here are two: a) The smartest people generally don't want to come work for your lifestyle business. b) Funding removes the financial constraint that prevents you from hiring the smartest people you can find.
7/ All this reminds me of @cdixon's post: "Climbing the wrong hill." When you're climbing a hill, don't forget to ask yourself if you want the things you get when you reach the top. Because if you're reasonably smart and driven, you probably will. http://cdixon.org/2009/09/19/climbing-the-wrong-hill/ …
8/ Lastly...the constraining factor in the startup ecosystem is the # of founders who can execute. I think 4HWW/lifestyle business founders are the biggest untapped natural resource. They know how to bootstrap, break with norms, execute, and sell.https://twitter.com/typesfast/status/920729346670596096 …
Are lifestyle businesses really about optimising for free time, or are they about optimising for the lifestyle you want?
That’s the point. I realized that the “lifestyle” I wanted was to work a lot with smart people :) so not a good fit for a lifestyle business, because other smart people don’t want to work for your lifestyle business.
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