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Pitched to Death in the Future Head: Startup Weekend Tampa Wrapup

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I show up at the HCC Dale Mabry 4:30pm on the third day of Tampa Startup Weekend. While the event’s ambitious would-be entrepreneurs were feverishly putting together presentations for the final pitch contest, I was enjoying a 12 p.m. "breakfast" at Café Hey. I’m a writer, after all, and the hungover Sunday brunch is one of the artist's most inviolable rituals. By the time I drifted in, later than the White Rabbit, the teams were too busy talking to walls and running through PowerPoint slides to give me much good copy, so I helped myself to some of the fajita spread.

The sponsored free food was a big distinction between this and the DIY art world I call home, and the entrepreneur’s existential drive to make things marginally more convenient and efficient isn’t going to drive anyone to start a band anytime soon. But in those final frantic minutes, you could sense the passion and creativity being poured into the projects.


Once the presentations kicked off at 5 p.m., you could again see the punk-rock ethos of bootstrapping and hard work, if you squinted your eyes just right. The teams had accomplished a heck of a lot in a couple of days and nights, including not just building rough prototypes of apps and websites, but, even more impressive to me, putting together sponsorships and agreements — the team behind the “Best Idea Ever” online pitch contest already had prizes lined up for their first weeks’ participants.
The final pitches, at four minutes each, ranged from weird to genuinely exciting. Listening to a guy talk in serious terms about the business potential of a viral joke meme generator borders on surreal, but then again, a lot of people with out-there projects could benefit from a bit more strategic thinking.

There were also several more substantial projects. In particular, I’ve been excited all weekend about the Rainmaker app (@tbrainmakerapp), which hopes to connect teens and young adults to jobs, and RFPCoach, a group hoping to help more small businesses land government contracts. There was a political and social benefit aspect to them that I think points to the compatibility between high ideals and business-mindedness.

Of course, there’s also a certain mix of optimism and blindness to these and other techy social improvement projects, like One Laptop Per Child. They’re arguably superficial attempts to solve problems with deep and intractable roots — an app isn’t going to change the reality of poverty, poor education, and a sputtering, unequal economy that makes it hard for young people to find work.


Either way, I clearly don’t have a good ear for which of these projects businesspeople are actually interested in. I thought the Rainmaker presentation in particular was great, and with HCC entrepreneurship director Andy Bolton leading the team, that’s no surprise. But both Rainmaker and the RFPCoach got edged out. The final winners, picked by a panel of experienced Florida entrepreneurs, were the pitch contest platform, a job search site for interns, and, in first place, Pitch a Tent, a booking tool for campsites (I was told the double entendre was intended).

Sitting in on Startup Weekend Tampa showed me, you might say, how the other half lives. The participants were mostly people who have actual marketable professional skills, or aim to. That’s something I’ve certainly never made much of a priority, maybe partly because I came of age in an era when the pressures weren’t quite so brutal. But at its best, Startup Weekend and startup culture more generally gives those folks a framework to aim for more transformative goals. After all, these are the folks who know and care enough about the details of the economy to try and improve them — even if just a little bit, and even if the main goal is to make a profit.

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