XSITE 2011, TechStars Demo Day, the Bruins, and Coolio: 25 Things to Remember From Boston’s Hell Week

Ladies and gentlemen, after last week I hereby declare the end of high season for tech events in Boston. We’ve had our celebrations, drunk our grain, and talked our heads off. Now, before we start getting some things done around here, let’s reflect just a little more.

The following took place during a 24-hour period last week:

—Coolio performed at the DartBoston/TechStars Demo Day party.

—The Boston Bruins beat the favored Vancouver Canucks in Game 7 of the Stanley Cup Finals for their first title since 1972.

—Fashion guru Alexandra Wilkis Wilson, co-founder of Gilt Groupe, shared the stage with me at our XSITE 2011 conference at Babson College (photo gallery here).

I’m not sure which of these pairings was least likely—fashion and I have rarely shared the same sentence—but the fact that all three happened in the span of a day suggests Armageddon is upon us. And, given the collective lack of sleep in this region (or at least this office) during that time, I will refer to it as Hell Week—after the Navy SEAL training where candidates are pushed to their limit, sleep less than four hours over 5.5 days, and emerge on the other side stronger than they thought they could be. I mean it in a good way, really.

All of this calls for a retrospective of highlights I’m able to remember through the haze of last week. Let’s get right to it:

1. I remember TechStars Demo Day kicking off with “I’m Shipping Up to Boston” by the Dropkick Murphys blasting from the speakers of the Royale nightclub—and all the startup teams joining managing director Katie Rae on stage, clapping, wearing a mix of company T-shirts, camouflage tuxedo suits, and other hipster items.

2. I remember a lot of raucous whooping and cheering for the startups (before, after, and sometimes during their pitches), and intro music for each speaker. A bit over the top, but I understand the need to build excitement. One investor called the format distracting, but he was in the minority.

3. I remember a mix of presentation styles, which was nice—from “here’s my life story” to “let’s get right to the business,” from laid-back to in-your-face. Also I remember Walt Doyle from Where (now PayPal) looking like a veteran stand-up comic as he introduced the first TechStars startup, EverTrue.

4. I remember angel investor Bill Warner introducing Ginger.io’s Anmol Madan by saying he was “fearless.” Case in point: some of Madan’s research work at the MIT Media Lab was on “trying to understand women with a computer.”

5. I remember lots more financing being announced by lots more companies than usual over the past couple of years (see this updated list of TechStars Boston financings for the current class). Perhaps Y Combinator’s $150K guaranteed investment for graduates of the program is not so big an advantage anymore.

6. I remember Hardi Meybaum of GrabCAD saying he likes Boston because it’s “the only place in the world where we don’t need to explain that CAD means ‘computer aided design.'” (He’s from Estonia.)

7. I remember Nabeel Hyatt from Zynga Boston (formerly of Conduit Labs) announcing his first angel investment, in Memrise. And Harmonix’s Eran Egozy, a relatively recent angel investor himself, backing The Tap Lab. Things are definitely starting to happen here.

8. I remember that Memrise had something to do with memory. Ha ha. Actually, it has to do with learning foreign-language vocabulary words online (for now). Founder and U.K. memory champ Ed Cooke said, “We’re reinventing learning.”

9. I remember Cooke and The Tap Lab’s Dave Bisceglia talking about “social gaming methodologies to get people to come back” and “addictive gameplay mechanics,” respectively. Like those are good things. Which they might be, depending on where you sit.

10. I remember Sravish Sridhar of Kinvey saying he’s putting the “BaaS” (backend as a service) in “Badass.” The idea: provide an easy cloud-based backend for mobile apps and their developers.

11. I remember strong themes around education and e-mail (which is not going away anytime soon, sadly) from several of the TechStars companies. Senexx is building knowledge management systems for big companies using an e-mail interface; Help Scout is providing an e-mail-based customized help desk for businesses. On the education front, EverTrue is developing a donor information system for universities and nonprofits; Spill runs an online peer counseling service, targeting college students; and Memrise is about online learning.

(I remember not sleeping the night of the Bruins’ Game 7—on the eve of XSITE 2011, our biggest conference of the year. Let’s take a breath, or a quick snooze, and then dive into XSITE…)

12. I remember XSITE keynoter Desh Deshpande saying, “You can’t mandate innovation. People need freedom to do what they want to do.”

13. I remember Desh also saying, “Tenure and entrepreneurship do not go together.” And, “Universities have to not get in the way of company formation.” On the topic of healthy ecosystems, he added that “we need companies at all stages of the life cycle.” He pointed out that because of the dearth of strong IPOs in the past decade, there is a gap between very established companies and newer upstarts.

14. I remember Phil Sharp of MIT saying that a number of technical wrinkles need to be ironed out before biologists can get real bang out of an open-source biology movement like the one championed by former Merck SVP Stephen Friend.

15. I remember Edward Jung of Intellectual Ventures saying the U.S. is “one of the worst places to do mega-projects”—very large-scale innovative efforts in areas such as climate change, healthcare, and energy and water infrastructure.

16. I remember Alexandra Wilkis Wilson of Gilt Groupe saying she isn’t seeing a new Internet bubble, Gilt isn’t planning to go public or get acquired in the next year, and that five years from now, both Gilt and Groupon will still be around. (Maybe after a merger, called Gilt Groupon?)

17. I remember TripAdvisor’s Stephen Kaufer talking about “desperation times” when the company was close to running out of money, before it switched to a consumer focus. TripAdvisor has since grown to become perhaps the biggest Web startup in the Northeast.

18. I remember similar tales of ups and downs from NextView Ventures’ Lee Hower (PayPal, LinkedIn). It seems like all companies go through at least one near-death experience. The good (and lucky) ones survive.

19. I remember Jamie Goldstein from North Bridge Venture Partners saying, “We’re in a social media bubble,” and that VCs should invest in other areas. Todd Dagres of Spark Capital perked up at that comment—and said that people should indeed invest in other sectors since the time to bet on social media was a few years ago.

20. I remember Paul Sellew of Harvest Power saying that unfortunately it will take a major situation for the U.S. to get serious about alternative energy. “There’s going to be a crisis and then we’ll mobilize,” he said.

21. I remember Sellew saying Harvest completely changed its business model after its Series A round (in response to a question about companies’ biggest mistakes). To which Frank van Mierlo of 1366 Technologies said that sounded “like a plan,” not a mistake.

22. I remember van Mierlo saying his “most painful” mistakes have been in recruiting. (They wouldn’t have to do with his poker face, that’s for sure. When asked about 1366’s relationship with the U.S. government and Department of Energy, he revealed nothing about his company’s $150 million DOE loan that was announced the next morning.)

23. I remember Pattie Maes of the MIT Media Lab saying there are “lots of opportunities to innovate in interfaces.” She showed quick video snippets of gestural interfaces, projected images you could interact with, a “mouseless mouse,” and an intriguing method for cutting and pasting pictures and other data from your phone to your laptop using just a finger.

24. I remember an unintentional comedy routine by Katie Rae and Xconomy’s Wade Roush as they juggled 12 early-stage startups, founders, and the audience applause-o-meter (Wade’s iPad) during the “Xpo” session of XSITE. (It was in contrast to the slick production value of TechStars Demo Day, but both formats worked well.) Of course, I also remember the rant session before lunch, but we (and others) have covered that already.

25. I remember having a hell of a good time talking with speakers and attendees at all the events that week. A special thanks to our XSITE hosts, Babson and Olin College, as well as to all our event partners and sponsors, for making it all possible.

So let’s do it again next year—and see how far we’ve all come by then.

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