Yesterday I was asked my thoughts on organizing, facilitating and overall what I would do differently on teeing up a Startup Weekend like event.  It pulled me back into the reaches of … ‘Oh yeah…” what would I do differently.  I haven’t organized or put on a Startup Weekend before but I’ve been a participant, a judge, a speaker, a mentor and an advocate of the scene for quite sometime.

No doubt the idea has crossed my mind on what I would do differently.  

This conversation occurred just hours before a similar conversation occurred with another person on putting together pitch events.  Specifically things like Wakeup Startup, which has kinda eased into a bit of stealth mode at the moment.

Pitch events to me are really just variety shows.  Startup Weekend events are much more, and thats a good and bad kinda thing.  But what is next?

I have my thoughts.

I think at the heart of both these events is of course community, and or brining people together, that is people that want to come to together to rally around a notion of starting up, starting new.  Its at the core of most of these people really, the challenge, the promise of something thats powered by the “I can’ or “We will” its about business and opportunity, and that hustle gene in you working its way to be surfaced in any aspect of who you are.

Its about inducing a state of entrepreneurial play.

To me, there’s so much you can do at events like this:

Role play, be the leader, be the dev, be the designer, play with roles you have and ones you’ve always wanted to try.  You don’t have to the developer, you don’t HAVE to be the constraint of who you think you are.  These events allow you to play.  Scratch that other side of yourself in a real world, real use, real potential startup aspect.

Experiment, breathe, while there are “rules” there are also no “rules”.  In many ways the goal of the event is to make everyone in the room a NEO.  You are the one.  Whatever path you took to get there, it matters less than the outcome of what you achieved.  We’re rarely if ever judged on the how of a journey yet the end of whether we won or not is what’s always in focus.  But until we do the how, we won’t know how.  I’d argue that people that learn to experiment, learn to play, learn the various hows, get addicted to them and they become the cornerstone of their being.

Make Something.  Prototyping to me is oxygen.  I have to constantly create things.  Its my ability to be truly who I love to be, who I really want to be, a creator, a person who can will things into existence.  I love that.  And why not?  These events we dare people, do it.  Go do it, why not.  For one weekend, be a god, have fun.  Go.

Delusional Energy.  At the heart of so much of business is the act of selling and making others believe, even better if your position on whatever it is actually connects with people and they get it as well.  This mind meld skill needs to be fostered, and practice makes future in my book.  I made a video about delusion, the pros and cons of it.  I love this idea, and we all need to embrace it more.  Get to play, PLAY more with what you think you can do but be mindful of your own intoxication of such things.


In the end what I suggested to both these people is foster environments that are less about process and more about play.  Sure we need frameworks to facilitate and remind us in some ways the constraints- the greatest constraint of all in business is will it work, can it make money, but these events are not about making money, they are about making people who can start to inch closer and closer to the notion of what they work on next is not only backed by play, backed by practice and experience but the money they gain is well earned, well rewarded.

Practice your state of play in what you make.

Photo by Lidya Nada on Unsplash

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