5 founders talk Chicago tech's biggest strengths — and weaknesses

by Andreas Rekdal
April 22, 2016

This week, Chicago played host to its second Venture Summit — an opportunity for the nation’s leading VCs to meet with fast-growing tech companies from Chicago and its surrounding regions.

The summit’s presenters ran the gamut of leaders in Chicago tech, from Mayor Rahm Emanuel and J.B. Pritzker to some of the city's most promising young upstarts, including

, and — which announced a new $2.2 million seed round from the presentation stage.

This year, the conference is highlighting 90 companies, who have been meeting with attending VCs from 147 firms from across the nation over the course of the past two days.

“We wanted to showcase the variety and the capabilities of these companies here in Chicago,” said conference chair Mark Tebbe, adding that companies were chosen by asking the community.

The founders of five of the city’s most successful tech companies participated in a panel on the unique advantages of — and challenges facing — Chicago as a tech ecosystem.

Here are five large takeaways from that conversation:

1. Chicagoans are extraordinarily loyal

Founders and employees tend to stick with their companies, even when the going gets tough. Looking back at photos of the

staff from 2008, founder Chris Gladwin said more than half of the employees still work there eight years later — a remarkable feat, considering how most of them were hired straight out of college.

2. Chicago’s tech founders want to see each other succeed

After taking a meeting with a recent Washington transplant, Shradha Agarwal, who founded 

, was perplexed at being asked what she wanted in return. In Chicago, companies help each other because they want to see the ecosystem thrive — not because it might pay dividends down the road.

3. But we still have work to do in building up a lasting, multigenerational tech ecosystem

Silicon Valley success stories don’t come out of nowhere. Part of the Valley’s success is derived from the fact that founders of decades-old tech companies stick around and reinvest in younger companies.

's founder, George Bousis, said that his hope is to one day be able to invest in companies founded by former employees from his own company.

4. Chicagoans should dream bigger, and embrace failure

“In the Valley, you know that if your company fails you can walk across the street and get another job,” said Al Goldstein, founder and CEO of

Located on Chicago's scenic Riverwalk. It’s home to nearby trendy restaurants, a thriving startup community, and public transportation.
. If you want to go big, you need to be able to take risks — but it’s hard convince people to take risks unless the community gets more comfortable with failing on occasion.

5. The ecosystem benefits from a diverse economy

Many of Chicago tech’s biggest success stories are in the B2B space — and that’s no coincidence. Unlike many cities, Chicago doesn’t have one dominant industry but many, meaning that there’s plenty of opportunities for young companies to get in touch with major actors in every conceivable business vertical.

Andrew Sieja founded

as a lifestyle consultant company, and pivoted to being a leader in the legal tech space after delivering on an order for legal software. Countless other Chicago startups have benefited from rubbing shoulders with leaders in other industries, rather than being siloed with other tech companies.

Image via Built In Chicago.

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