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University of Chicago Booth School of Business alumnus Tony N. Pritzker, MBA ’87, and his brother J.B. Pritzker, say they work well together at their private investment firm because their strengths are complementary. Tony runs operations. J.B. looks for promising companies with potential to grow.

Since founding their namesake investment firm in 1996, The Pritzker Group has acquired or invested in more than 100 companies. The firm’s venture capital arm, formerly called New World Ventures, is the largest technology venture investor based in the Midwest.

The Pritzker brothers sat down with Roxanne Martino, MBA ’88, managing partner of OceanM19, to talk about their approach to investing. Their conversation with Martino, who is also co-chairperson of Chicago Booth’s advisory council, took place in May at Booth’s 65th annual Management Conference in Chicago.

Here are their top three tips for entrepreneurs:

The one question the Pritzker brothers ask before they invest.

When J.B. and Tony Pritzker talk to companies who want them to invest, they have lots of questions. But only one really matters, they say: “What is the pain you are alleviating, and how deep does it go?”

Failure is a fact of life.

Don’t let your ego prevent you from asking for help. When Tony and J.B. Pritzker invest in a company, they invest in a leadership team. If the team doesn’t know how to ask for help, that can spell disaster. “If you’re in the venture capital business, you’ve got some failures. It’s a fact of life.”

Is it Amazon-proof? If not, what can we do to make it Amazon-proof?

For companies that sell products, Amazon looms large. The Pritzkers experienced first-hand the power of the online retail giant when one of their portfolio companies, a maker of TV wall-mounted brackets, began losing market share to foreign companies selling on Amazon. The foreign firms undercut their prices and took a big bite out of their sales. So, the Pritzkers decided to take on Amazon directly, selling their TV brackets under a different brand name at a lower price. It was a tough decision, but it worked. Their brackets are now Amazon best-sellers. “If you don’t keep your critical thinking cap on, you’re at risk.”