A Dartmouth MBA Takes on Commercial Real Estate

42Floors founder Jason Freedman went searching for the "hardest, crappiest, schleppiest, yuckiest problem" he could find

42Floors founder Jason Freedman went searching for the “hardest, crappiest, schleppiest, yuckiest problem” he could find

Jason Freedman, 34, didn’t go to Dartmouth’s Tuck School of Business in 2006 to found a multimillion-dollar startup in commercial real estate. In fact, he dropped his first real estate course after a few weeks. “Most of business school wasn’t a great connection for me, classes wise,” he says. “I wasn’t any good at accounting or capital markets, and I wasn’t interested in them like almost all of my peers.”

Then, he met Gregg Fairbrothers. The veteran professor challenged Freedman to take his Introduction to Entrepreneurship course to flesh out an idea for a social networking startup. “Everything he said made sense to me,” Freedman says. “I just devoured it.” The startup tanked, but Freedman confirmed his career path–entrepreneurship.

After graduating in 2008, Freedman moved across the country to Silicon Valley, where he and a few friends founded FlightCaster, a service that predicts flight delays. The team won a coveted spot in Y Combinator, a prestigious startup accelerator that has funded such smash hits as Reddit, Airbnb, and Dropbox. Freedman and his colleagues thrived in the incubator environment–they created a successful business, attracted $1.3 million in investment, and later sold it for “millions.”


But Freedman wasn’t finished. He needed a new challenge. So he fell back to a trusty idea source–problems that piss him off. He hated searching for startup office space. There is no “Kayak” for commercial real estate, he points out. Renters must sift through multiple sites littered with building specs and photos –most taken from the outside. It was a “horrific” process, he says.

Bingo. Instead of his next office, Freedman found his next idea–42Floors. He teamed up with seven others to tackle the problem. “We were deliberately searching out the hardest, crappiest, schleppiest, yuckiest problem we could find,” he says. “We found it in commercial real estate.”

Startup savant Paul Graham advised him to bring the industry out of the Internet Stone Age, but first Freedman would have to “learn to be one of them.” Freedman hit the books to learn the market. He completed eight college-level real estate courses, passed the state exams and earned both sales agent and broker licenses. Then he set off to produce a site that pools listings into a user friendly, searchable interface. On the startup’s current website, renters can filter properties by size and price, pull up floor plans, browse photos, and schedule tours without leaving the site–it’s a seamless user experience. But not on the backend. The company manually enters each piece of information and sends out photographers to snap listing pictures. “Everything is really unsexy,” Freedman says. But investors see it differently and have poured some $17.7 million in the company.

While Freedman concedes that the MBA set him on the right path, he doesn’t pin 42Floors’ success on the experience. Rather, he believes B-schools are generally poor places to learn entrepreneurship. “A lot of times an MBA will take 100 hours and put it into researching their pitch deck and business plan,” he says. “At the end of which, they don’t have anything. They just have a pitch deck and a business plan.”

“The single best business school that anyone can attend right now is Y Combinator,” he adds. Easier said than done. The incubator’s acceptance rate hovers around 2%–Harvard Business School’s is 12%. But for those who don’t get in, Freedman points to the accelerator’s online trove of essays, podcasts, and videos, which can be accessed for free. Even after all the preparation and pitches, founders still need one more thing–a little luck. “Serendipity is like the lifeblood of a startup,” Freedman says. “You have to have it.”

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