Up until a few weeks ago, there were only a few words that I associated with startup companies. One was “balls,” another was “brains,” another was “heart attack.”

There are elements that lead up to those associations, first and foremost being that I was probably in diapers when I was initially exposed to startup culture. My father, an entrepreneur to the core, would be on his gigantic cell phone spitting stress into the mouthpiece; I’d be strapped into a car seat drooling into the mangy mane of a Cabbage Patch Kid and even then, I swear I was thinking, “F*&$ this, dad, I’m going to be a writer.”

However, if things had been going then like they are now, there’s a chance that the words that I currently associate with entrepreneurialism might have formed differently &emdash; maybe even in the shape of “addictive,” “creative,” and “thrilling.” To a great extent, this can be attributed to the Internet, and to the now increased rate at which new concepts can become tangible products. However, to another smaller, but potentially as powerful extent, this can be attributed to Startup Weekends d i.e., 54 hour-long, high-intensity events dedicated to melding minds and starting companies.

We chatted with Andrew Hyde, Startup Weekend’s Boulder-based founder — and brand new community manager for Techstars.org — about the now globally occurring events, but never really found the answer to our main question: When &emdash; and how in the hell – did startups become so much fun?

Joshspear.com: Tell us about your history &emdash; how is it that you love entrepreneurialism so much?

Andrew Hyde: I remember learning how to count money from my favorite teacher, an elementary school volunteer of 40 years, Nellie Zook. At the end of the lesson she said that when we all started businesses, she would be our first customer, to check on our money counting skills. That stuck with me a bit.

I was always tinkering around in school with businesses, making conference videos to pay my ticket cost and helping open up a coffeeshop, among other things. In college I really avoided anything business related. After college, I moved to Boulder planning on being a 9-5 designer – but that didn’t work out as planned. August of 2004 was not a great time to be a designer; it seemed everyone was out of work. I couldn’t get an unpaid internship let alone a job. It sounds like a cliche, but I fell into it. Someone, somehow, sent me a $500 check to make a full site, and I started freelancing. I became skilled at Usability and Interaction Design, started freelancing around many startups, and fell in love.

JS: Startup Weekend was only founded in 2007, yet things have been progressing pretty quickly. Can you give us a brief history of event, from the beginning through now?

AH: It started in early July, when a midnight conversation at TechStars (techstars.org) kicked it off into reality. The concept was simple: Get a bunch of smart, startup types together and start a small project over the weekend. The weekend went really well, and by Monday morning the reach and success of the event caused over four hundred people to inquire about doing a Startup Weekend in their city.

The six months after that first weekend are really a blur to me. There have been 16 Startup Weekends around the globe. We just hired Ray Angel to take over the operations of the weekends.

JS: There are a lot of elements that go into the creation of new companies, yet Startup Weekend seems to prove that – given a good selection of brains and the right environment – the process can move along very quickly. How is Startup Weekend changing the face of entrepreneurialism?

AH: I think Startup Weekend is changing the game a bit by bringing together founders to meet and test each other out over a short period of time. It is speed dating for entrepreneurs in a way.

Startups are hard, extremely hard. You can’t start a successful startup one in a weekend. You can start building a community, which is what Startup Weekend is really about. I think the weekend makes entrepreneurialism more human to people just wanting to check it out, or for people looking to expand their skills.

JS: Can you give us a play-by-play on how a typical weekend runs?

AH: Before the weekend, very little planning goes on. Some weekends have been planned by finding a location, writing one blog post and one tweet. Tickets are $40 and get the founder food for the weekend, a facilitator, swag and a bunch of extra surprises. I think the AdHoc style works really well for the people that come to the weekend (they provide the passion, we provide the flexibility and challenge).

6pm Friday: Everyone gets together; figures out who else is there; what would be interesting to build. 7pm: Pitches start (if you have an idea for a product you pitch it to the group). 8pm: Teams start breaking off (generally about nine teams will form during the weekend, creating nine products or companies). 9pm: Hopefully teams have solidified their concept and created an elevator pitch (even a simple one) by now. 10pm: Break off to a bar or coffeeshop to continue the discussion and attempt to paper prototype out their application.

9am Saturday: Crowds pour in; work starts on development. Noon: Lunch.
3pm: More coding, business plan development, and a special guest (from our friends at smtvmusic.com) plays a 3 song acoustic set. 6pm: Special guest drop-ins and pitches from the teams. These guests are generally angel investors or VC’s. 9pm: Gut check on the product; basic prototype building; group get-together for drinks and to talk about the products everyone is working on.

9am Sunday: The day’s work starts again. Noon: Projects are being developed; live website with signup is set up; more special guests drop in. 6pm: Sink or swim time for those looking for a weekend launch. 9pm: Presentations from each company; what worked, what didn’t, what could go better. Flowers are given to the founders to give to their loved ones that let them spend the weekend on a new venture.

JS: What are some of the most promising startups that have emerged from the weekend so far?

AH: I would say Skribit (skribit.com) and Handshak.es (handshak.es) are the two most promising.

JS: Without the accessibility of information available today, primarily via the Internet, would these weekends be as possible, or as successful?

AH: The weekends are a classic Internet success story. I started them without really knowing anyone in tech, with no money, and with no business plan. The idea was well timed, we had some luck, and it just happened. Twitter saved the day on more than one occasion, providing last minute planning help to a place to crash. It is amazing how fast a message can spread.

JS: Tell us about VC Wear….

AH: It is my favorite joke that won’t die off. The concept came from watching a VC at a bar getting a really bad pitch (the words ‘contextual advertising startup’ were yelled a few times if I remember correctly). Matt Emmi (mattemmi.com), Paul Roales (proales.com) and I were joking about how all VC’s needed funny undershirts. “Don’t Pitch Me Bro” was the first one, quickly followed by “Fuck It, I’ll Fund That.” It went from there, and pretty soon we had 30 shirts designed. Matt and I were flying back from the Bloomington Startup Weekend and decided to launch it on “Startup Plane,” our own mockery of the Startup Weekend model. We launched the site and it took off.

JS: What I love about VC Wear is its intrinsic snark &emdash; that it serves as a great example of a new startup yet manages to poke fun at the very nature of the process by which it was created. My experience with investors and entrepreneurs can be surmised in saying that they like to take themselves very seriously &emdash; is that something that you agree with, and if so, something that you’d like to see change?

AH: I think both sides are guilty of not really getting each other in this situation. I see and hear about so many horrible pitches, and a fair amount of startup pitching horror stories. There is so much at stake, and there is a good reason why everyone is so serious in the matter. I wanted to lighten the mood, even for just a second, and poke fun at all sides of startup culture. My main problem with startup culture, on all sides, is the amount of burnout. It doesn’t feel like any thought goes into the longevity of entrepreneurs or VC’s. Entrepreneurs
think that they need to launch yesterday and get acquired within a year (last year), and VCs never want to miss out on the next big thing. There seems to be more and more thought put into this year after year (especially post bubble), but it isn’t quite there yet.

JS: Where and when will the next Startup Weekend be taking place?

AH: San Antonio (May 16-18).

JS: In the next year, what do you hope that these weekends, both internally and as a brand, will accomplish?

AH: I hope they will continue to build community. That is the first goal of every weekend. I am now starting to hear of successful partnerships that formed at Startup Weekend.

JS: You just started working with TechStars, correct? Can you tell us about what that is?

AH: I am very excited to be working with TechStars this year. TechStars is a startup mentorship program at the seed stage investment model. Ten companies are accepted each year into the program and receive up to $15K in funding and mentorship by 60+ advisors (a sort of ‘been there, done that’ type of group). In addition to that, the companies get office space in downtown Boulder. I am working as the Community Director, helping with these ten early stage companies over the summer and beyond.