Is the Golden Gate Bridge looking a little maroon lately? Perhaps. More than 2,600 Chicago Booth alumni now live and work in the San Francisco Bay Area. Though the tech scene dominates, large numbers of alumni also work in consulting, marketing, and investment banking—bringing a data-driven sensibility to the start-up hotspot. Alumni who attended Polsky Center’s West Coast Demo Day at Google headquarters (see “Something Ventured”) shared how they’re bringing The Chicago Approach to the city by the bay.

The Bay Area Experts

Ryan Gembala, ’10, Founder and general partner, Pathbreaker Ventures

Shruti Gandhi, ’12, Managing partner, Array Ventures

Sean Singleton, ’08, Director of state programs and financial operations, Clark Street Associates

Jack Stockert, AB ’05, MBA ’10, MD ’10, Managing director, head of business development and strategy, Health 2047

Rama Veeraragoo, ’12 (EXP-17), Cofounder, GoodRipple

Shruti Gandhi, ’12, managing partner at Array Ventures, said alumni are uniquely positioned to succeed in the area’s entrepreneurship and finance scenes. “Booth alumni are resilient, hardworking and analytical,” she said, adding that some founders have told her they seek out Booth graduates when hiring.

“We’re more rigorous in our thinking and diligence. We’re ready to roll up our sleeves and get into anything,” Gandhi said.

28%Fellow venture capitalist Ryan Gembala, ’10, shares that view. “I think it’s one of the reasons that Booth alumni are placing higher in venture capital firms out here,” he said. “With their data-driven approach, they’re either landing in venture firms, or they’re working in technology companies, because data is really driving all product decisions these days.”

Gembala’s career progression would not have been possible without the Booth network. A fellow alumnus hired him after graduation to work at a Bay Area VC firm. After a job at Facebook sourcing corporate deals, Gembala decided to strike out on his own, founding preseed venture firm Pathbreaker Ventures in San Francisco.

“I can look around Demo Day and see Booth alumni who are investors or advisors in my fund, and faculty who are involved,” he said. “There’s no way any of this would be possible without the Booth network.”

“I’m passionate about bringing Booth into Silicon Valley even more.”

— Sean Singleton

75%The connections extend well beyond the tech industry, said Jack Stockert, AB ’05, MBA ’10, MD ’10. Alumni
were instrumental in helping him find his next calling after he and his wife, Emily Walker Stockert, AB ’05, MBA ’10, MD ’15, moved to the area from Chicago.

“The Booth network was great in terms of being able to massively scale out and talk to a wide variety of people in different industries,” Stockert said. “It has been incredibly valuable.” Now the head of business strategy for San Francisco–based health-care innovation company Health2047, he still makes time to pay it forward. “I have lunch with or meet with a Booth student or former Booth student on a regular basis,” he said.

Sean Singleton, ’08, a US Air Force veteran, hopes interaction among all UChicago alumni in the Bay Area can lead to greater opportunities. “One of the things we’re trying to do through the University of Chicago Military Affinity Group is bring all of the schools together. I would love to see Booth lead the charge in that cross-UChicago collaboration.”

Top high Level jobs titlesSingleton, the director of state programs and financial operations for Palo
Alto–based consulting firm Clark Street Associates, described moving to the area as “an awakening.” He said, “I’m passionate about bringing Booth into Silicon Valley even more.”

He shares that goal with Rama Veeraragoo, ’12 (EXP-17), cofounder of forthcoming social-good app GoodRipple, who is working on an initiative to support UChicago and Booth alumni and student entrepreneurs in Silicon Valley.

“We hope we can build a close-knit community into an entrepreneurship ecosystem which helps these alumni and student founders start and scale their start-ups,” he said.

Booth Selects

The Point
Tucked below the south anchorage of the Golden Gate Bridge, Fort Point provides a scenic vista of the bridge and the San Francisco Bay. Photograph from Shuttestock.

The Morning Run: Rancho San Antonio County Park

Stockert recommends the combined open-space preserve and county park for a morning run. A 10-minute drive from Cupertino, the park boasts miles of paths to explore by foot, bike, or horseback. “It’s beautiful—you can get up into the mountains, and it seems like you’re completely detached from civilization even though you’re in the Bay Area.” 

The Networking Lunch: Caffe Centro

A hub of the dot-com boom of the 1990s, San Francisco’s South Park neighborhood still draws a tech-minded crowd today. Gandhi suggests heading to local gem Caffe Centro for a sandwich with a side of networking. “It’s where the local investors hang out,” she said. “If you’re coming from Chicago trying to figure out where they are, come to the café and learn the lingo.”

The Historic Vista: Fort Cronkhite

Cross the iconic Golden Gate Bridge and you’ll find Fort Cronkhite—a former World War II military post standing sentinel at the edge of the Pacific Ocean, and one of Singleton’s favorite area sites. Its barracks and mess halls are still preserved, now housing the National Park Service. Hike in the surrounding Marin Headlands for a view like no other. “It’s beautiful, pristine real estate where you can hike and have the best vantage point of San Francisco Bay looking back into the city,” he said. “It’s off the beaten path, so it’s a great place to go reflect.”

The Up-Close Vista: Fort Point National Historic Site

Greens Restaurant
Greens Restaurant is a vegetarian institution in San Francisco. Rama Veeraragoo appreciates the eatery for its cuisine, as well as its stunning waterfront view. Photograph courtesy Greens Restaurant.

Wander back to the San Francisco side of the Golden Gate Bridge to find another vestige of the area’s military history. Fort Point, built into the base of the soaring structure just before the Civil War, was originally intended to fortify the bay. “It’s right underneath the bridge. You can almost reach out and touch it,” Gembala said. “You can walk from there to the beach to enjoy the water. There’s a great spot to grab a cup of coffee called the Warming Hut.”

The Working Latte: Café de la Presse

For a coffee spot more suited to business meet-ups, Gembala heads for the pastries at Café de la Presse, a Parisian-inspired bistro near the border of San Francisco’s historic Chinatown neighborhood and the Financial District. “It’s good for casual VC and entrepreneur meetings, but a little elevated,” he said.

The Stylish Dinner: Greens Restaurant

Located in the city’s waterfront Fort Mason neighborhood, the James Beard Award semifinalist Greens Restaurant serves vegetarian fare that has earned national acclaim. It’s a favorite of Veeraragoo’s for more than just the locally sourced dishes. “I really like Greens because of the view it has over the water,” he said. Diners are treated to a picture-perfect panorama encompassing the nearby marina, the Golden Gate Bridge, and the verdant peaks of Marin County in the distance.