10 Highlights From XSITE 2013: Akamai, Blackjack, Crashlytics, & More

Digging out from our fifth annual XSITE innovation conference at Babson College yesterday…huge thanks to all of our speakers, sponsors, attendees, and hosts for an inspiring day indeed.

I saw at least part of every session, and wanted to highlight a few things that stood out to me. Let’s start from the end of the program and work backwards (see also a recap from my panel on the state of Boston tech):

10. In our startup “Xpo” session, Wanderu (like Kayak for buses) won for best pitch, and CareSolver (coordinating elder care) won for most innovative company. Our guest judges were Vanita Shastri from TiE Boston, Neelan Choksi from Tasktop Technologies, and Bill Aulet from MIT.

Wanderu beat out a valiant effort from Crunchbutton, which had a kung pao chicken delivered to Xconomy CEO Bob Buderi in the audience.

9. The MIT Blackjack reunion panel did not disappoint. As we learned, the blackjack team was run as a business—a very tight ship—and with that came all the issues and politics of any business.

Lessons for startups: Bill Kaplan from FreshAddress pointed out that successful entrepreneurs are not big risk-takers; they bet big when they can mitigate risk and seize an advantage (e.g., by knowing the exactly correct play for any blackjack hand and situation). Jon Hirschtick from Belmont Technology (formerly at SolidWorks) added that “the long run is longer than you think.” In other words, don’t generalize from just a few hands—stick with it. And Neelan Choksi of Tasktop Technologies said, “Clear up what your employees worry about.”

I was backstage, but I think angel investor Semyon Dukach said he wouldn’t join the team again if he had a choice. He didn’t find it fulfilling, ultimately. If he could do that time over again, he would try to create more value through an Internet startup, finish his PhD, or some such activity.

8. Ben Einstein from Bolt was a little late for his panel on hardware, manufacturing, and the “new era of design.” You know why? His car broke down. There’s a lesson about the state of hardware design in there somewhere.

7. The “founders’ stories” panel with CEOs Mike Baker (DataXu), Diane Hessan (Communispace), Jeremy Hitchcock (Dyn), and Jason Jacobs (FitnessKeeper) was fun and lively, even though they had collectively gotten about 40 hours of sleep this whole week. Such is the life of a modern tech CEO.

6. Lots of great insights from Olin College President Rick Miller’s panel on serial entrepreneurship. Advice to entrepreneurs from David Berry of Flagship Ventures (he of some 11 startups): “Ask the question that will kill your company.” And from Meredith Flynn-Ripley from HeyWire: “Think like your customer, not like an entrepreneur.”

5. “The world is changing underneath us, we have to adapt.” That was David Chang, the co-founder of Actifio, talking about how 10 years ago, the enterprise tech market was mostly in the U.S.—but now companies think about being global from the start.

4. In the age-old discussion of where to build a company, Silicon Valley is saddled with a “BS factor,” “dumb money,” and weather that’s too good to get real work done, while Boston has an “inventive, lively spirit,” “a story going on,” and, of course, crappy weather for half the year. (Home court advantage at XSITE, though.)

3. Miguel de Icaza of Xamarin and Wayne Chang of Crashlytics (now part of Twitter) agreed that in their world it’s important to “delight developers” (de Icaza) and “engineer a better emotional experience” (Chang). Where they differed was on the exact delivery of that experience.

De Icaza thinks the end of an interaction is most important to enterprise customers; if a colonoscopy is painful, but the last few minutes are OK, people remember it more favorably and are more willing to do it again. Chang thinks the beginning is just as important as the end, at least for installing software (not for a colonoscopy). Let’s move on.

2. Telecom companies are moot, because they are middlemen in an increasingly open ecosystem of bits and connectivity. That’s one reasonable takeaway from Bob Frankston’s talk about the deeper state of tech innovation—and how not to just chase the Next Big Thing. As he puts it, opportunity is more important than innovation per se.

1. Akamai CEO and co-founder Tom Leighton gave a sweeping keynote about the history of Boston tech innovation, including the ups and downs and serendipities of Akamai’s life story. For example, the company’s market cap hit $30 billion at the height of the bubble, when it had little real value yet (that was Leighton being too modest, like a lot of scholars in the business world).

In summary, technologies change, markets change, people change. So, his take-home message to entrepreneurs: Be tenacious.

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