Boston comes on strong at Dublin’s Web Summit

Taking a Photo at Web Summit

A gaggle of technology entrepreneurs, students, and investors made their way from Boston to Dublin last week to take part in one of Europe’s largest technology conferences, the Web Summit. Among 20,000 attendees and a roster of distinguished speakers, Boston’s finest shined bright at the event, showcasing the vast breadth of expertise this city fosters. Here’s a look at the highlights.

Current and Former Bostonians Take the Stage

Investor Panel with Kevin Colleran


Headliners at Web Summit this year included Amazon CTO Werner Vogels, Founders Fund’s Peter Thiel, actress and activist Eva Longoria, musician Bono, former Apple CEO John Sculley, and The New York Times‘s David Carr, alongside a diverse representation of speakers with Boston roots and ties, including:

    • Dharmesh Shah, Hubspot co-founder and CTO; and alumnus of MIT and MIT Sloan
    • Drew Houston, Dropbox co-founder and CEO, and MIT alumnus
    • Matthew Prince, Cloudflare co-founder and CEO, and HBS alumnus
    • Oisin Hanrahan, Handybook co-founder and CEO, and HBS alumnus
    • Bill James, senior baseball operations advisor for the Boston Red Sox
    • Melody Hildebrandt, global head of cyber security Palantir Technologies, and Tufts University alumnus
    • Wayne Chang, global head of developer experience at Twitter; formerly founder and chairman of Crashlytics, prior to Twitter acquisition; University of Massachusetts, Amherst, alumnus
    • Kevin Colleran, venture partner at General Catalyst Partners, early Facebook employee, serial entrepreneur, and Babson College alumnus
    • Scott N. Miller, Dragon Innovation CEO; Bolt partner; Olin College of Engineering Adjunct Professor; former iRobot executive; and MIT alumnus
    • Don O’Neill, VP of engineering, operations, and infrastructure at TripAdvisor, and Brandeis University alumnus
    • David Aronoff, General Partner at Boston-based Flybridge Capital Partners, and HBS alumnus
    • Bill Ready, Braintree CEO, and HBS alum

While the content offerings were vast, the most entertaining panel I attended during the entire conference was titled, “The Secret to Success,” featuring an all-star lineup of investors: General Catalyst Partner’s Kevin Colleran, Founders Fund’s Geoff Lewis, KPCB’s Mood Rowghani, and Y Combinator’s Justin Kan, interviewed by Bloomberg technology journalist Mark Milian.

The discussion, billed as a “101 for entrepreneurial badassery,” had its panelists and onlookers on the edges of their seats as Milian ricocheted through a slew of tough topics such as international investing best practices, tech diversity issues, founder suicide, and competitive landscapes.

At one point, Milian pitted Lyft investor Lewis against Uber investor Rowghani, asking what the secret to success had been for the two firms so far. Lewis jumped in, “Lyft has been good at innovation, and Uber has been good at copying. Lyft did an excellent job at pioneering peer-to-peer ridesharing. Uber did an excellent job at copying.”

As an audience member, my jaw was on the floor about half of the time. The panelists, though, were quite adept at taking tough questions, Rowghani responded to Lewis with nothing but kindness: “I agree with much of that assessment, particularly that ridesharing is a market that isn’t a monopoly situation. There is room for a number of players.”

On the question of geographic investment concentration, Colleran shared that while he lives in Boston, the majority of his investing is in New York and San Francisco.

As one of the first 10 Facebook employees, Colleran pointed out that had founder Mark Zuckerberg stayed in Boston after dropping out of Harvard to found the company, the ecosystem in the Boston area could have looked much different today. He added, though, that the geographic concentration of markets is a huge positive for work-life balance, since everything you need to do – meetings, events, and so on – are all in the same vicinity.

On balancing work and family, a question rarely asked to an all-male panel (kudos to Milian yet again), Colleran says, “The issue is deciding when to actually go home.” Most people don’t work 9-5 in tech, he noted, pointing out that the real balance starts with pulling oneself away from the office.

A “Cheat Sheet” from Dropbox’s Drew Houston



Dropbox co-founder Drew Houston, too, had advice to wield for students and CEOs in a keynote interview with CNNMoney tech reporter Laurie Segall, who opened the interview, harkening back to Houston’s 2013 MIT commencement address with a question related to his famed “cheat sheet.” In that speech he said he wished he would have had a cheat sheet for post-graduation life, and on it there would be a tennis ball, a circle, and the number 30,000.

“The tennis ball is all about finding something you’re obsessed with – like a dog chasing a tennis ball relentlessly,” he explained, and said the circle referred to his years throughout college, going from one project to another until he thought of the kernel idea for Dropbox when he forgot his thumb drive one day. The number 30,000, he said, came from a bout of insomnia. “I had just moved from Boston to San Francisco, and I couldn’t go to sleep one night. So, I was up, reading in bed, when I read the sentence: ‘You’re going to live for 30,000 days.’ I went to my calculator; I was 24 years old at the time. I calculated that I was about 8,000 to 9,000 days down already, almost a third through my life.” That realization motivated him to make the most of each day.

On Creating a Web Summit Equivalent in Boston

Web Summit Audience


Web Summit was founded just four years ago by Paddy Cosgrave and has scaled to 20,000 attendees with 2,000 exhibiting startups, with limited organizational hiccups here and there (cough, cough, there was barely WiFi access the entire time, for starters).

MassChallenge’s Cory Bolotsky says that he sees similar possibilities for Boston. “We’ve said over and over that we want to build a SXSW-like event in Boston,” says Bolotsky. “Well, Paddy just went ahead and did it in Dublin, and today it is obvious that Web Summit will be a long-standing annual tradition for the global startup community.

“We have all the resources to build the same thing in Boston, but we just need to stop talking and start doing if that’s a vision that our community has for Boston,” he said. “We need to work harder if we want to maintain a reputation as one of the world’s leading innovation hubs.”