Within a few months in 2001, Groupon CEO Eric Lefkofsky's net worth had soared from zero to $70 million and then plummeted back to zero again.
"People were knocking on my door late at night with subpoenas and lawsuits," Lefkofsky said. "I found myself in court. And I was literally meeting with lawyers, days away from going bankrupt because I couldn't possibly pay all these people that were coming after me."
His reflections on his journey through the tech boom and bust during Chicago Ideas Week's "Entrepreneurship: How I Did It" talk set the tone for one of the best events I've attended in a long time.
His advice: Never give up. In September 2001, Lefkofsky started InnerWorkings, which helps companies reduce their printing costs. It grew quickly. Lefkofsky took it public in 2006. Two more IPOs and a megamerger later, he's a billionaire.
Some other lessons I gleaned follow:
•Be Prepared. "I was at a yoga clinic and there on the mat to my right was Oprah," recalled Honest Tea co-founder Barry Nalebuff. "It was hot yoga. And I had cold samples with me. And (my co-founder) says to me, 'How did you know Oprah was going to be there at your yoga retreat?' The answer: I always carry samples with me because that's what being an entrepreneur is about."
•Hustle. IndieGoGo CEO Slava Rubin said he got his first taste of entrepreneurship reselling baseball cards. He described the experience as his "first hustle."
"I would go to these (baseball card) shows and say, 'Mister, how much for the Larry Johnson that's supposed to be $10 according to Tuff Stuff that you're now selling for $6?" Rubin said. "It's $6, kid. How many do you have? It's $6, kid. How many do you have? It's $6. How many do you have? I have 50. OK. I'll take all 50 for $150." (Or $3 apiece.)
So Rubin bought the cards at 70 percent off retail.
"All I did was walk around the show, selling three at a time at $6 or $7 a card, and they thought they were taking advantage of me," Rubin said.
"What matters is execution, hustle, perseverance," Rubin said. "So don't worry about do you have a good enough idea. It's just a whole lotta work."
•Know a great idea when you see it. Ping Fu didn't invent 3-D printing. But she saw enormous potential in the technology long before most — in 1997.
"I was like, oh, my God, this is personal fabrication," Fu said. "I (thought) personal fabrication was more intuitive to have in your home than a personal computer. Because, you know, we can make Christmas ornaments," she joked.
She started a company, called GeoMagic, which she moved from Champaign-Urbana to North Carolina's Research Triangle in 1999, to supply software to the 3-D printing industry.
The market was so undeveloped at the time that she pitched her product this way: Imagine one person has a microwave oven with a turntable in the middle. You put an object on the turnable. You push a button. The microwave scans the image. You dial a number. It sends the image somewhere else where they have the same machine. They push a button, and it prints the object. The result is a 3-D fax machine.
"I made it up," Fu said. "Then I said GeoMagic will make this idea a reality."
3-D Systems acquired GeoMagic in February for $55 million in cash.
Why Max Levchin left
Max Levchin, a co-founder of PayPal and the chairman of Yelp, was another Illinois resident and immigrant who left. Levchin's family moved to Chicago under political asylum from Ukraine in 1991. His mother was a computer scientist who taught him how to program; his father, a playwright.
After graduating from the University of Illinois in 1997 with a computer science degree, he left for Silicon Valley. At Chicago Ideas Week's Friday Tech Summit, festival founder Brad Keywell asked Levchin why he left.
Chicago at the time "lacked any kind of ecosystem to support entrepreneurs," he said. He told the story of approaching an unnamed law firm in Chicago for advice on raising capital. The advice would come with an "eye-popping" bill. He told the firm that its peers in Silicon Valley took options in companies in exchange for legal services. Levchin described the response as, "Yeah, whatever, kid."
Today he said he believed Chicago and Silicon Valley "aren't all that different." But he said the Valley remains a far more "lubricated place" for entrepreneurs. A founder's needs are "universally understood" in the Valley, enabling all discussions to occur in a shorthand.
ABC News journalist Martha Raddatz, who drew widespread praise for her moderation of the 2012 vice presidential debate, gave the Minow Lecture in Communications on Thursday evening at Northwestern University in Evanston.
"I've never studied so hard for anything in my life," Raddatz said of debate prep. "Especially the budget part of it. Because, you know, you're sort of like, 'Oh, my God. I have to go through Paul Ryan's budget?'"
Chicagoans Newton and Josephine Minow, both Northwestern grads, created the annual lecture series in 1981. In Newt Minow's introduction, he joked that he attended the school "before the Civil War." He said Jo's roommate was Cloris Leachman, who went on to win an Academy Award, while his roommate was Sander "Sandy" Vanocur, a prominent TV journalist during the 1960s.
Minow then joked: "I was thinking that if we went to Northwestern today — I say this to you (university President) Morty and Mimi Schapiro — my roommate would be Cloris Leachman."