Since the dawn of the new millennium, there have been at most several thousand startup tech companies across the U.S. that have achieved unicorn status—crossing the $1 billion valuation.

Eric Lefkofsky, 55, the Chicago-based serial entrepreneur best known for co-founding online daily deals site Groupon, has given rise to six of them, evolving from discount coupons for pedicures to potentially lifesaving cancer treatments using artificial intelligence.

For most Chicagoans, however, the soft-spoken Lefkofsky remains something less than a household name, a billionaire entrepreneur whose brand is not emblazoned on a skyscraper, despite helping to put the city on the tech world map.

“He’s been a huge force in Chicago,” said Howard Tullman, a Chicago venture capitalist and the former CEO of 1871, the city’s influential tech hub. “This is not a guy who spent a lot of time chasing recognition, and he’s been a little bit below the radar. And I think that’s really particularly admirable.”

While unicorns are far more plentiful now than when venture capitalist Aileen Lee coined the mythical appellation in 2013, Lefkofsky remains a rarity in Chicago tech circles and beyond, launching and nurturing a diverse portfolio of big ideas brought to life.

For much of Lefkofsky’s remarkable run, the startups have been developed at 600 W. Chicago Ave., the century-old former Montgomery Ward Catalog building, which became known colloquially as the Groupon building with the stratospheric rise of the e-commerce website.

At one point, Lefkofsky’s various ventures occupied more than three-fourths of the massive 1.65 million-square-foot building in the Goose Island neighborhood along the Chicago River.

Founded in 2008, Groupon, which once spurned a $6 billion takeover offer from Google on its way to a $25 billion valuation, has fallen in recent years to a fraction of its previous worth amid sharp revenue declines. In January 2024, a downsizing Groupon moved to smaller digs downtown, leaving a 300,000-square-foot hole in the onetime nexus of the Chicago tech scene.

Once its largest shareholder with a 40% stake, Lefkofsky stepped down from an active leadership role at Groupon in 2015 and has since pared his holdings to just under 10%.

But Lefkofsky is still hard at work inside the building where the online daily deals site was born, fully invested in developing the next big thing.

Besides Groupon, the list of billion-dollar startups founded by Lefkofsky includes InnerWorkings, Echo, Mediaocean and Pathos AI. In recent years, most of his time, money and energy have been focused on Tempus, an AI-powered health care technology company he founded in 2015 to treat cancer and other diseases.

Lefkofsky serves as CEO of Tempus, a publicly traded company with 4,000 employees, offices and labs across the country and a market cap of more than $13 billion. More than any other company in his portfolio, the mission is personal to Lefkofsky, who started Tempus after his wife was diagnosed with breast cancer.

“In the process of her treatment, I ended up deciding that I really wanted to focus on this space, and spend the rest of my career thinking about cancer, how to bring technology to cancer care,” Lefkofsky said during a recent visit to Tempus headquarters, a bustling office and laboratory space that occupies 217,000 square feet of the former Montgomery Ward/Groupon building.

More than 1,000 employees circumnavigate the bustling fifth floor Tempus office around an atrium that Lefkofsky said was a spiral parking ramp before the building—a National Historic Landmark that once housed the country’s oldest mail-order firm—was converted to tech space 25 years ago.

The Tempus workforce is a melange of techies, scientists, oncologists and pathologists, all blended together with the same goal: using AI to better treat cancer.

“What’s unique about Chicago is that we have a little bit of everything,” Lefkofsky said, navigating seamlessly between the worlds of technology and science on a tour of his sprawling office.

There are two main areas of focus for Tempus.

In the life sciences realm, the company is analyzing molecular and clinical data with the help of artificial intelligence to facilitate drug research and development. Tempus is also pioneering new technology such as biological modeling, where “mini-tumors” are regrown from lab samples to test the efficacy of drugs.

The other half of the business for Tempus is clinical genomic sequencing, where tissue from cancer patients is shipped into the lab from all over the U.S. and analyzed using artificial intelligence to personalize treatment based on molecular biomarkers.

Half of the nation’s 14,000 or so oncologists regularly order sequencing tests from Tempus, Lefkofsky said. Tempus is one of the largest genomic sequencing companies in the country, helping doctors identify mutations to inform cancer treatment decisions, he said.

“When we started Tempus 10 years ago, maybe 10% of the patients were sequenced,” he said. “Today it’s over 50% in the United States, and soon it will be 100%. It’s just standard care.”

Lefkofsky has poured $100 million into Tempus, which has yet to turn a profit. He is confident that is about to change.

Tempus reported nearly 90% year-over-year revenue growth during its second quarter earnings report Aug. 8, raising its full-year 2025 revenue guidance to $1.26 billion. The company, whose stock price has more than doubled this year, is projecting a positive adjusted EBITDA of $5 million for 2025.

Beyond seed money, growing Tempus from a startup to a $13 billion company has also required a lot of sweat equity from Lefkofsky.

“It was not a small amount of money that I ended up putting into a series of rounds,” he said. “But more than the capital, it’s been kind of all-consuming for the last 10 years of my life.”

He was pretty busy before Tempus as well.

In addition to the six unicorns, Lefkofsky co-founded venture capital firm Lightbank. His startup success has made him the 643rd richest person in the world with a net worth of $5.9 billion, according to the Forbes real-time billionaires list.

A Detroit native, Lefkofsky earned a bachelor’s and a law degree at the University of Michigan before making his mark on the Chicago tech scene.

In the wake of the dot.com bubble burst, Lefkofsky launched a string of startups, beginning with InnerWorkings, a printing technology company he founded in 2001. Two years later, Lefkofsky moved InnerWorkings into 600 W. Chicago, the hulking former warehouse that had been recently redeveloped as a tech center.

“When I came to the building, it was about 90% vacant—and most of these floors were concrete for parking,” Lefkofsky said. “There were maybe one or two built floors and they were maybe half built, and we took some space with InnerWorkings.”

With plenty of room to grow, Lefkofsky and his portfolio soon did.

In 2005, he co-founded Echo Global Logistics with longtime business partner Brad Keywell, using technology to drive freight transportation. The company went public in 2009, growing into a multibillion-dollar logistics giant.

Next up, Lefkofsky and Keywell founded MediaBank in 2006, an advertising technology startup that evolved into Mediaocean through a 2012 merger with a New York-based rival.

Then came Groupon, an e-commerce launch that has become almost mythic in its arc.

In 2007, Andrew Mason, then a recent Northwestern University music grad, started a website called The Point with $1 million in seed money from Lefkofsky. The initial concept was to bring together people with a common cause to take action, but the mission soon pivoted to a daily deals retailing site, and Groupon was born.

Groupon created its own e-commerce niche with heavily discounted daily deals on everything from manicures to meals, blasted out to subscribers via email. It exploded in popularity and employment grew from a handful to more than 10,000 worldwide as the company’s valuation blossomed into the billions.

Google tried to purchase Groupon for nearly $6 billion in 2010, but Mason and his investors said no deal. By 2011, Groupon was valued at $25 billion, and the company went public, raising $700 million in the largest tech initial public offering since Google.

From an investor standpoint, it has been mostly downhill from there.

Operating losses, management missteps—including a disastrous 2011 Super Bowl ad— and a rapid post-IPO decline in valuation led to the 2013 ouster of Mason as CEO.

In August 2013, Lefkofsky was named CEO of Groupon. But one year into his new role, Lefkofsky’s life changed when his wife, Liz, was diagnosed with breast cancer. By 2015, he stepped down as CEO at Groupon and started Tempus.

Ten years later, Lefkofsky said his wife is “doing well” and Tempus is thriving at the intersection of technology and medicine.

In this case, necessity was both the mother of invention—and their three children.

“The work we did to try to figure out how to treat her was actually personalized using data, and so it ended up producing a good outcome,” Lefkofsky said. “So in many ways, she was Patient One of Tempus.”

From the outset, Tempus employed artificial intelligence to analyze medical data—long before the term, and the technology, came into widespread use.

As the ability to use AI in health care at scale gains momentum, the opportunity for Tempus to become a standard diagnostic tool and an integral part of mainstream medicine continues to ramp up, Lefkofsky said.

“We’re helping tens of thousands of patients around the country manage their cancer care, and we’ve expanded it to other disease areas such as cardiology and neurology,” Lefkofsky said. “It’s just good to see a lot of the roots we planted take hold.”

Living up to his company’s name—tempus means time in Latin—Lefkofsky somehow manages to find enough time for a number of the city’s civic and cultural organizations.

Longtime Glencoe residents, Lefkofsky and his wife are actively engaged in philanthropic pursuits, establishing an eponymous family foundation in 2006. He has also served on a number of boards, including Steppenwolf Theater Company, Lurie Children’s Hospital and World Business Chicago.

“I think he’s been a tremendous entrepreneurial influence, and I think that he’s also been maybe even more impressive, frankly, on the philanthropic side,” Tullman said.

In November, the Art Institute named Lefkofsky as its new board chairman, putting the tech billionaire in charge of overseeing the museum, the school and an ambitious plan to usher in an era of new development at the historic South Michigan Avenue campus.

His new role came with some unexpected drama when the museum’s director, James Rondeau, returned from a voluntary leave in June following a board investigation into an incident where he removed his clothes and disrupted a United Airlines flight to Germany.

“As a board, we were thrilled to have him back and thrilled just to be moving forward,” Lefkofsky said.

Meanwhile, his day job may be entering a new phase as fledgling companies leave the nest and head off on their own—faster than new ones launch.

InnerWorkings, Echo and Mediaocean have all been acquired by private equity firms. Czech investor Dusan Senkypl, now the largest stakeholder in Groupon, took the helm of the struggling daily deals site and last year moved the company to a smaller space in the Leo Burnett Building on Wacker Drive as part of a larger cost-cutting initiative.

Pathos AI, a Chicago-based biotech startup Lefkofsky co-founded with Tempus COO Ryan Fukushima in 2020, gained unicorn status in March with a $365 million round of funding that brought its valuation to $1.6 billion. Its day-to-day management is vested in other hands.

Pathos, Echo and Tempus still call 600 W. Chicago Ave. home.

Lefkofsky continues to focus on building Tempus, which in late August announced the acquisition of Paige, an AI company specializing in digital pathology. The $81 million deal is mostly being paid with Tempus common stock.

With six unicorns under his belt, Lefkofsky is not ready to give up the CEO’s role at Tempus anytime soon.

“I think my focus over the next several years is just running Tempus and making sure that it delivers on its mission,” Lefkofsky said.

As to the prospects of starting unicorn No. 7 down the road, Lefkofsky didn’t rule it out.

“I don’t have any plans to start another company,” he said. “But every once in a while, you know, things come up and you get excited.”

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