Wild, Wonderful Startup Weekend

You, the stray Medium reader, may not know what Startup Weekend is. To clarify: it’s one part summer camp, one part boot camp, and one part clusterf#%k . I know because I recently participated in one here in Charleston, SC.

More specifically, it is a 54-hr event where over a hundred strangers meet up on a Friday evening, several of them pitch ideas for companies, they break themselves into teams around the best ideas, and work like crazy until Sunday evening to accomplish a feat that ordinarily would take months: Deliver a coherent presentation demonstrating that the problem you’re trying to solve is real, that people want your solution, that you can build it, and that it has major revenue potential.

I’m writing this for myself but what I want to say to anyone reading is this: Participate in a Startup Weekend. They happen in cities all over the world. Find the next one near you and do it.

What I want to write for myself here is basically to explain why.

The weekend was not my first experience of startup life. I started Bound a few years ago with a couple of really talented guys and learned the equivalent of several MBAs in the process. I stepped away from Bound but never lost my appreciation for the challenges and education to be had in entrepreneurship. I take every chance I get to listen to pitches and even spend my free time reading books like Running Lean and Four Steps to the Epiphany.

I have found that it is very easy to be critical, especially these days, of that guy claiming to have the next great app or that girl launching a platform that’s going to be the <insert successful company> of <insert anything>, all the while harboring some idea of my own that I’m not pursuing for fear of failure.

I always want to be around people who are going for it, who are making something happen, because I want to be one of those people.

There is a Theodore Roosevelt quote that captures this for me:

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, ...who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”

I participated in Startup Weekend because I wanted to get out of the stands, even if just for a couple days, and get my hands dirty in the arena. Get dirty they did fo’ sho. I’m already looking forward to the next one.

So let me get to why.

I do not think the business work is what it used to be. I have not lived forever so I do not have first hand experience of what it meant to have a career or run a company in 1890 or even 1990. From what I understand, though, the path for everyone involved was essentially linear. You start somewhere, you stay there, you move upward and then you end.

I’ll leave it to another time to reflect on why things have changed but, suffice it to say, “linear” does not describe the path of success for an individual’s career or the life of a company. Startup Weekend condenses into 54-hours the critical skills you will need to survive, much less succeed, on today’s path fraught with “pivots” and “unicorns.”

I’ll touch on just three for now.


Collaboration is typically not pretty. It is such a pleasant sounding word and is often accompanied by pleasing images of hands working together and ideas being shared. If they are realistic at all, such photographed moments come at the end of a struggle between opinionated, smart, talented to agree upon a solution to a shared problem.

One of the first results in a google image search for “business collaboration.” The image appears in this article.

That struggle is the name of the game at Startup Weekend. You have to learn to listen well and articulate your thoughts clearly and remain open to others’ ideas no matter how convinced you are of your own.

You will find yourself pulling your hair out or having an urge to bang your head against a whiteboard. That’s when you know you’re really in it. Being able to work with a team to solve problems without doing either of those is fundamental to success anywhere I’d want to work these days.


When you have 54 hours to do 54 days worth of work, you very quickly learn to jettison anything that isn’t absolutely essential. Second to collaboration, if there’s a skill I consider critical today it is just that. Anyone who can clearly define an objective and then work diligently and deliberately toward it alone is a welcome teammate of mine — especially if they can do it collaboratively. As anyone who has participated in a Startup Weekend can attest, if you don’t learn that skill by Sunday morning it will show Sunday night.


My headers do not work well together grammatically at all but I’m going to roll with it. The final thing I’ll touch on here is maybe the most valuable of all. If you remain aware and reflective, you will learn a tremendous amount about yourself at Startup Weekend. You will learn from which situations you shy away and from which you irresistibly gravitate. You will learn what you’re naturally good at and what you struggle with. It is really a wonderful opportunity to gain insights about yourself in a very short period of time that can help guide you the rest of your career.

Here’s to the doers at Startup Weekend CHS 2015. I’m the one in the tie.

Ok. That’s that. I feel that I have accomplished here what I set out to accomplish. I wanted to express my enthusiasm for Startup Weekend and articulate why I feel it. This post itself carries that spirit. I know it’s not the goodest written article on the Internet but I didn’t want the fear of the critic who “points out where the doer of deeds could have done them better” to keep it unpublished.