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For context, he was homeless about fifteen years ago. And is still very involved in helping the homeless.
My impression is you wouldn't have been able to guess that he was homeless X years ago based solely on his middle-class life now. Real bootstrapping
I believe one of everyone's worst fears is to be homeless (whether acknowledged or not - I hate inevitably thinking about it whenever I see someone on the street).
The flip side of this is that having been homeless you have nothing to fear. I had a period of homelessness in my early 20's - it was fairly self inflicted, I was burned out from the ridiculous hours in my first job and needed to escape from everything but I was already a decent programmer so I knew I could get back on the ladder - so nothing like what this guy went through.
The good thing though was that it made me feel like I could cope with anything. Homelessness reduces your horizons to "where am I going to sleep" and "how am I going to get some food" (to the point were those two things are all you think about most of the time) and having come through that I felt like I could try anything because no matter how badly it went wrong I would be ok.
Thanks for sharing your experience and perspective. How do you push yourself as an entrepreneur if you don't fear the normal things?
Sociality seems to have negative feedback at the edges. The height of the potential barrier is easy exceeded if you're self-sustaining and near impossible if you're not.
The only part of this I've personally experienced is similar chicken and egg problems trying to move to new country. You can't get a apartment without an employment pass, the bureaucracy can't send you letters without an address. If you have money you can bootstrap off a lawyer or accountant's credentials otherwise there isn't always a way.
He mentions friends helping him several times, but not crashing on someone's sofa, and a couple of times he specifically mentions that he wouldn't go to a shelter - I'm curious as to the reasons for this? The shelter maybe because he feared getting stuck there?
Interesting piece. Thanks to colinprince for posting it.
The most useful wisdom always comes from the chlenges we personally face. This is where the best startup ideas come from.
That is startup-as-self-help wishful thinking.
Is that really true? I'm not a part of the 'startup community' but looking at a few of the startups that have achieved some success (Google, Reddit, Balsamiq, Dropbox) it doesn't really seem like they were a result of personal challenges faced by the founders. Maybe there are lots of other good examples of where startups are inspired by challenges faced by founders.
I haven't studied the stories of those companies that closely, but to be successful, you have to use the resources you have wisely. One of those resources is personal experience.
You have to experience a problem to know how to solve it; and the problem isn't always as serious as being homeless. 37signals built their own Project Management platform, for example.