Why you should care

Because sometimes it pays to be dull.

It’s many a little boy’s dream: Play football, row, wrestle your way through high school, letter in a Division 1 sport in college and then, somehow, actually make money by powering none other than the Final Four.

They probably did not dream of spreadsheets.

While millions of fans get ready to see if the Kentucky Wildcats can take the title as the NCAA champions in Indianapolis, just about zero of them will have any idea of who plays a crucial, behind-the-curtain role for the whole shebang. No, they’re not outlining pick-and-roll moves for players. Brent Frei and Mark Mader have co-founded a rather sizable company that does one seemingly simple thing: upgrade the classic spreadsheet. Which is not as boring as it sounds. Because by storing their system in the cloud, the company is allowing once-fumbling organizers to put together fantastically large events, track shipping schedules and manage large teams on just their smartphones or tablets — kind of like Google’s spreadsheets on an industrial scale. Yeah, it’s kind of embarrassing that you didn’t think of it first.

The mania of arranging March Madness is a classic example. Marc Klein, an associate at Populous, the firm contracted by the NCAA to plan the Final Four, recounts a vertiginous day in the life of planning one of the world’s biggest sporting events, including practice schedules, vans for transportation and timetables for when the lights go on and off, plus tracking some 272 vendors, 160 deliveries and thousands and thousands of reminders. The planning begins 18 months in advance, and Populous obviously has to hand over a clean set of information to the NCAA. All while conveying a smooth attitude of cultivated nonchalance.

Eep. And you thought handling your bracket was bad. And all of this is done on a spreadsheet.

Smartsheet’s biggest selling points are some of its simplest notions: Allow collaboration, provide good analytics, do Gantt charts well.

“Putting the right information in front of the right people sounds really easy — but it’s really hard to do,” says Prasanna Tambe, professor of information, operations and management sciences at NYU’s Stern School of Business. Which explains why Frei and Mader’s firm, the Seattle-based Smartsheet, founded a decade ago, is suddenly having its moment, slap-bang in the middle of the business world’s productivity zeitgeist. More data, more collaborators and a slow untangling of the “inertia” people have around their old, comforting tools make this a lucrative market these days.

Tim Porter, a Smartsheet investor at one of Seattle’s top venture capital firms, Madrona Venture Group, points out that some of the biggest selling points of Smartsheet are some of its simplest notions. Allow collaboration. Provide good analytics. Smartsheet does Gantt charts — a status tool — well. Indeed, Frei and Mader’s distinctly unsexy set of changes has them making distinctly sexy amounts of money. They boast 60,000 paying customers — three years ago, only one company was paying over $10,000. Frei and Mader don’t plan on going public (they co-ran a previous public company, Onyx; “It sucked,” Frei says) and they’re raking in funding — $26 million in 2012 and $35 million last year, which Frei says they “didn’t really need.”

There’s something meta about building something to help run or start a company while running or starting your own company. It gets personal, naturally: Frei recalls their days at Onyx when, after the bubble burst, they had to go from 800 to 500 employees in a matter of days. It was baffling: Who had been in charge of what? Who would take over what? How could they manage lines of communication? But Frei and Mader didn’t exactly trade on that experience correctly, at first. They built the first incarnation of Smartsheet between 2005 and 2009, and they built it, erroneously, from the perspective of executives: top-down. They picked up a few thousand users, but quickly realized they weren’t going to explode. With just a few months of funding left, they relaunched a more customizable, open platform in 2010.

Working together through two startups is a rarity in the serial world of entrepreneurship. But these dudes are football and fraternity blood brothers. Frei was a Dartmouth graduate student a year out of college, helping to coach his old team, when Mader entered as an offensive lineman as a freshman. Frei, who is 6-foot-7 and speaks in a voice with the timbre of André the Giant, takes up space in a physical and metaphysical sense alike. He leans back in a chair against a view of Seattle from their Bellevue office, while Mader leans earnestly forward. Mader looks and speaks much more like a tech executive than his partner.

Their sports backgrounds, naturally, give rise to some predictable sentiments regarding leadership. “It’s really a metaphor for business,” they each say at various points, one referring to a near-loss against Columbia, another referring to a triumph against Yale. Frei, a former defensive tackle, calls himself a “read-and-react” type, with Mader as the offensive CEO sort. They like to translate it to work culture too. Mader brags: In five years, they’ve lost only one developer. (“Unheard of!” cries investor Porter.)

But all the teamwork in the world doesn’t necessarily add up to a victory in the crowded cloud computing space. Not to mention the industry is rife with concerns over security, says Tambe. But here’s 48-year-old Frei and 44-year-old Mader’s take: They’ll probably just “acquire many companies,” including other productivity apps, Mader says, and for now they can test the waters by partnering with products like Microsoft Office 365 (an achievement, given Microsoft’s historical reluctance to go open source). So perhaps this is a unique industry where, instead of watching Salesforce and Google and Asana edge one another out, we’ll benefit from more couplings than we’d imagined.

Photography by Daniel Berman for OZY.

Correction: a prior version of this story suggested the Kentucky Wildcats are the defending champions. They are not. It is the University of Connecticut.

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