Chicago can teach Seattle a lot in terms of snow removal, but yesterday in a standing-room only crowd, Chicago entrepreneurs turned to a Seattle business icon, Microsoft CEO Steve Ballmer, for a lesson in building not only great companies but also a thriving tech community.

Mayor Rahm Emanuel, J.B. Pritzker and our very own Kevin Willer all said a few words before the never dull Ballmer took the stage. The first half of his talk was an impressive litany of highlights Microsoft has achieved since the launch of Windows 8 last October as well as a cool show-and-tell of new technologies.

Then, Ballmer sat down for a Q&A with Rob Rutenbar, Bliss Professor and head of the computer science department at University of Illinois, and regaled the audience with early stories of Microsoft and sage advice for all startups.

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(Photo courtesy of Vincent Cabansag, Starter League)

Startup Advice #1: Big Vision Helps

Ballmer shared an old college story where Paul Allen ran into the dorm room Ballmer and Bill Gates were in, and exclaimed to Gates “we have to build every piece of software for this machine.” The machine was the first microprocessor driven computer and was featured on the cover of Popular Electronics.

Never mind the fact that the machine on the magazine cover was the only piece of hardware of its kind. Gates and Allen built an environment to simulate and tool-ate. Ballmer pointed out this kind of simulation is much cheaper today thanks to tooling already in place, which brought him to his second point of advice.

Startup Advice #2: You Can Stand on the Shoulders of Others

By the time Gates convinced Ballmer to quit school and join Microsoft it was a 30-person company. Ballmer quickly figured out that those 30 people were doing the work of 45. When he approached Gates to hire 15 employees Gates replied, “ I didn’t ask you to drop out of school to bankrupt our company.”

Gates had yellow notes all over their apartment to constantly remind him how much money was coming in and going out. He never wanted to lose sight of the finances. This anecdote dovetailed in Ballmer’s obvious but important third point.

Startup Advice #3: Don’t Bankrupt Your Company

He reminded startups in the audience that, sure, they are there to make a popular product, but they are also there to keep in mind what happens with the money.

“We all know statistically what happens to most startups. Please avoid that.”

He went on to provide the recipe for success he believes all cities with great startups share:

1. They have great universities.
2. They are great places to live.
3. They have 1, or 2, or more big companies that have made it in the tech field, which helps fuel the VC funding.

When Microsoft was starting out, that anchor tech tenant in Seattle was Boeing. Perhaps Chicago’s future anchor tenant was in the audience for this very speech.

He closed by wishing everyone well and reminding entrepreneurs that even though there’s a risk in failing, there’s no real risk in trying because whether they fail or succeed they will be smarter, better, and have more opportunities moving forward.

Thanks to Heidi Lading, part-time marketing team member for writing this column. 

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