H-11: A Homeless Entrepreneur, a War Crimes Lawyer, and an Artist-Turned-Director of Ops Walk Into a Bar…


Guy walks into a bar

What begins as an odd twist on the classic “walks into a bar” joke…

…ends with a Paulo Coelho-ian twist.

In Coelho’s best-selling book, The Alchemist, an old king tells the main character, “when you want something, all the universe conspires in helping you to achieve it.”

On August 5th, I “came out of the closet” about going homeless and shared my plan with my Facebook network. It was a hard decision. Some friends and confidants had cautioned strongly against it.

But it was the right thing to do.

Sure, I received some strong criticism for my apparent insensitivity to those who are truly homeless with no other options. Yes, I’ve been told I’m naive, ignorant, and downright stupid. But I’ve also met some amazing people and heard uplifting words of encouragement and understanding.

Which brings me back to the title of this post…

This week I received a text from a friend:

“You want to come see my band play an open mic? Want to introduce you to my buddy who went homeless for 4 months.”

Uhhh YES. Besides the fact that my friend plays a mean cello (and always has interesting updates on his Cancer Dudes company), I’m trying to live without an apartment for exactly 4 months. #MATCH

What ensued was awesome:

  • First, I heard the story of an entrepreneur who ditched his apartment and lived in his place of work for 4 months while he saved money to launch his business*
  • While unlocking my bike outside the open mic venue… I met a Nigerian war crimes lawyer who had just moved from the Netherlands to Boston 3 days prior and made plans to explore greater Boston together
  • Shortly after… I had (non-alcoholic) drinks with an artist who was hired to run operations for an event company that has grown sales 1400% in the last year, who had discovered my website prior to our meeting… and came to the table with questions, ideas, and positive feedback
  • While out that same night… I ran into a former colleague who had read some posts on the site, was emphatically pro-HC, and joined us for a drink to catch up and reminisce

*And guess what? He’s homeless right now (again.) When we met he had his suitcase with him and was taking a red-eye to Milan to explore for a bit before heading off to Asia for business.


…it’s been a good week.

But what’s the point?

If you’re an entrepreneur, you’re probably familiar with lean methodology and the concept of “validated learning.” In a SUPER dumbed down nutshell it’s about trying things out, measuring the results, learning from them, repeat. It’s also about knowing and understanding your customers (or audience.)

When I shared my plan to go homeless on Facebook, I got immediate feedback from my peer group (or audience.)

And on top of that, because people knew my intentions and understood my wants and needs, they were better able to provide value tailored to them. #doublewin

I’m not saying that you should share everything and be 100% transparent with everyone. But you just might consider it ;)


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