Chicago entrepreneurs go far (like to New Zealand) to give other startup hubs a leg up

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Published on Feb. 04, 2014

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Every week Troy Henikoff, managing director of Techstars Chicago, holds open office hours locally, advising entrepreneurs on growing strong businesses. But his trip to Wellington, New Zealand last month proved just how far (literally) Henikoff goes to support the growth of startups anywhere and everywhere.

Especially over the past five years, Chicago entrepreneurs have been laser-focused on the city’s reputation as an international startup hub, advocating that entrepreneurs who’ve made it big stick around to mentor and invest in younger companies. But it’s also fair to acknowledge that our most successful local entrepreneurs are also part of a global digital ecosystem and support it in any way possible, which is key to building the very best companies.

“It’s not a zero sum game,” Henikoff said. “It’s important to help entrepreneurs in general. If we raise effectiveness of startups, we all benefit.”

Henikoff traveled to Wellington for a week in January because entrepreneurs and startup advocates there reached out to him, having heard of 1871 and the Chicago tech scene’s rapid growth. While he was in Wellington, he gave talks at local incubator CreativeHQ on pitching and financial modeling and also spent a few hours with Wellington’s city council. Brad Feld of Foundry Group and Techstars Boulder even Skyped in during the council meeting, extending his hand to help the city foster entrepreneurship by introducing his book, “Startup Communities.”

During his chats with New Zealand entrepreneurs, Henikoff said they “were most interested in how Chicago transformed over the past four to five years” and were asking how they could build that same ecosystem that exists in Chicago.

But mentors like Henikoff are careful of expecting other cities’ startup cultures to embody Chicago’s essence, in a way similar to Chicago entrepreneurs’ weariness of modeling Silicon Valley too closely. Wellington, for example, has a much different environment to work with, as several coworking spaces and accelerators are heavily backed by government grants and initiatives.

Even as Chicagoans are dedicated to developing Chicago’s own startup identity apart from San Francisco, they still support the hotbed of San Francisco companies. Among these many entrepreneurs are Match.com CEO Sam Yagan, a mentor for San Francisco-based Founder Institute, and BrightTag CTO Eric Lunt who contributes his tech expertise to Twitter in San Francisco as a senior technology advisor. A San Francisco-based “mobile tool box” for contractors called Getable benefits from the guidance of Chuck Templeton, managing director of The Impact Engine, who is on its Board of Directions.

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Blinkfire Analytics founder Steve Olechowski is lending his expertise even farther away: he is an advisor to Glassy, a social app based out of Valencia, Spain. Through his Glassy position, he works with the team on product and mobile strategies, U.S. market dynamics and U.S. distribution plans. Brandon Cruz, President of GoHealth, sits on boards of companies around the country, including California and Florida.

“I don't necessarily go out of my way to focus on other markets; there are great companies everywhere,” Cruz said. “Different regions might operate a little differently, so the best thing you get from working with companies all over the place is the ability to see different approaches, and use that as an advantage with all the companies you work with.”

Henikoff himself had the advantage of this nationwide support network of entrepreneurs back in 2009 when he was starting Excelerate Labs. As he was starting out, he approached Techstars and the Boulder team readily shared its best practices with “no expectation of getting anything back,” Henikoff said. But three years later when having lunch with Feld, they realized the mutual benefits of morphing Excelerate Labs into Techstars Chicago. The advice that Feld gave to Henikoff in 2009 to start Excelerate Labs later helped to make one stronger company overall, Henikoff said: “When they helped us out in 2009, they had no idea where it was going to go.”

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