the laughing cloud

hacking, inventing, and standup comedy

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I do Standup Comedy.  I don’t know how many patent-holding, unix-guru comedians there are out there, but I suspect I may be in a very small minority.

I’ve made millions of dollars.  I’ve sent millions of dollars to money heaven, with the help of the crash in 2008.  That crash was also a wake up call which resulted in “Let’s move to Key West!”… Key West is the bastion of the overqualified – a place where a Supreme Court Judge just might be driving a Pedicab, a place where some of the homeless guys have PhD’s, a place where you really don’t want to judge a book by it’s cover.

It’s also the kindest place I’ve ever been… much kinder than Canada – but it makes sense in a messed up way – the need is so much greater here – “The difference between Canadians and Americans is that Canadians expect tthe government to do everything for them, and Americans expect the government to do everything to them”.  No free healthcare means benefits for someone with cancer who can’t pay the bills.  And when there’s no safety net provided by the government, guess what?  People step up.  People donate.  People help each other.  People are aware of each other’s suffering, in real time.  People are more human.

I didn’t expect that part – I expected funky people and warmth.  Key West has the only Carribean climate in the United States, different than Miami; different than Marathon, even.

I rent a small office here.  A couple of years ago, there was a little note on the bulletin board about a Standup Comedy Workshop.  I went.  Met Tom Snyders – the Bicycling Comedian… 150,000 miles touring on a bike between gigs – (“I know what you’re thinking – they’re highway miles”)… and possibly the worst self promoter on the planet (on a per mile basis).  Only some crazy German has more miles…

I like standup.  I’ve often watched it and thought “hey – I could do that”, and here was a chance.  There were other considerations though.  The work I do, hacking, patents, and the like, I do in relative isolation… although I write a fair amount, I don’t talk alot… and the real problem with patents and startups is that they almost always need outside investment.

Gotta pitch those VC’s.

The only thing harder than asking people for money is making them laugh.  I’ll bet I could kill two birds with one stone…. so I took the course.  At the end of it was “the showcase”… a terror filled event.  Filled the house with friends.  Everyone had a great time.  I was relieved it was over.

Turns out Standup is not so different than all the rest of the stuff I do, except it happens faster.  Patents take years to find out if you have a winner or not.  Performing is closer to compiling code than anything else… good code, they laugh.  Syntax errors get you silence.  And you’re up in front of people alone, performing your funny code…

But it’s the variables that are so cool.  Presentaion can be the difference between a laugh and nothing.  The audience, the demographics, the amount of booze they’ve drunk… the comedians on before you, the rhythm of the show, your physical state, your material, and how many times you’ve been on stage. 

Standup comedy is people-hacking.   Find out how they work and make ’em laugh.

It’s also interesting to do something I’m not good at and improve over time.  I’ve bombed.  And once you’ve bombed, and survived, pitching a VC about your great startup is likely to be pretty easy.  It’s Toastmasters on Crack… you improve or you die.

I’m also pretty ignorant, really.  I was surprised in what low esteem most comedians are held.  Sort of makes sense when you think that a working comedian is doing well making $30K a year.  It’s a tough slog.  But there’s some awesome talent out there… if they can hang in there, and it’s a subculture, not unlike hackers really.  And like the hacking community, you’re measured by how well you do you’re thing, and you learn from your peers… in real time.

The only other time I’d experienced this sort of expertise-meets-contempt was with the Drag Queens here in Key West.  One of my side projects is Starshout ( – we do celebrity video messaging… Mad at someone – get a drag queen to insult them! (Pick Desiray for that gig!).  They’re so talented I didn’t understand the contempt.  Still don’t.  And talk about knowing how to be on stage.

But there are incredible benefits.  Every stupid, frustrating, ignorant thing I experience becomes material.  I now laugh at least ten times more than I used to.  I find dealing with people less painful, and dealing with painful situations easier.  And people are universally impressed with the courage it takes to stand up in front of a room full of strangers

If you’re in town this week – come see the show – it’s the Third Annual Comedy Showcase, upstairs at the Hog’s Breath Saloon at 8 pm.  It’ll cost you $5.  And if you can’t make that show, I can be seen at our monthly gigs for charity along with Wendy Carlisle and Tom Snyders as part of Standup4KeyWest…


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