To create sustainable competitive advantage, you’ve got to solve hard problems and get way ahead. The hallmark of what I tried to do with my companies is to fix something that’s broken.

By Megan Michelson

Peter Sisson T’94 always knew he’d become an entrepreneur. When he was a student at Tuck, he took a Myers Briggs test which told him entrepreneurship was an integral part of his personality. “I’m a very creative person. I like the idea of creating something from nothing,” Sisson says. “Tuck not only reinforced that I could do that, but it also prepared me to do that by teaching me how to write a coherent pitch deck.”

Since Tuck, Sisson, who lives in San Francisco, has launched five—and counting—companies. In 2019, Business Insider named Sisson one of the most powerful LGBTQ people in tech. His latest company is called Yaza, which he founded in 2018 and recently went live in the app store. Yaza enables its users to explore an interactive, searchable map of the world through the experiences of people they know. So, if you’re visiting say, Barcelona, you can watch videos of friends who’ve been to the area’s best cafes and art galleries and build and save an itinerary based on your findings. “For someone with a travel bug, you want to be able to experience another place is like through the eyes of people you trust—your friends, influencers, travel experts,” Sisson says. “You want to get that content from them, and get it pure, ideally in video, since that communicates so much about an experience.”

The app weaves together a visual history of specific places, whether they’re hiking trails or exploring museums. “It’s a tool to satisfy my wanderlust; to answer the question that I see inefficiently answered all the time on social media. People say, ‘I’m going to Berlin—where should I go?’ Then you see an endless stream,” Sisson says. “Other sites host reviews, but they’re from strangers. As someone who likes to get off the beaten track, I want to open it up to everyone’s explorations, not just guidebooks and travel experts.”

Sisson has been obsessed with travel since his first plane ride at age five. Since then, he’s been to 40 countries and accrued 4 million airline miles. “I believe if you can travel, it makes for a complete and rich life,” he says. His tendency is to avoid the well-traveled, pricier countries and instead go to uncharted places in more developing countries. In his twenties, he bought an open-ended, around-the-world plane ticket. He spent six weeks in Bali, visited monasteries in Tibet, and traveled to the center of Borneo, where he stayed in a village with Dayak tribesmen, camping in lean-tos and eating monkey meat they’d shot with poisoned darts. He’s been 150 feet below sea level in Palau and topped out at 18,000 feet above sea level on a peak in the Himalaya. “Everything has been an adventure,” Sisson says.

After studying computer science in undergraduate at Cornell University, Sisson earned a master’s degree in computer science and artificial intelligence from Stanford University. He got a job writing programming code for AT&T Bell Labs, before leaving to do volunteer work in Micronesia. “I realized very quickly that I wanted to have a bigger sandbox to play in,” he says. “I knew that business school would be the key to transitioning from a science and engineering background to learning more about management and business.”

He chose Tuck for its small class size and approachable professors. “The best thing about Tuck for me was the people I met. To this day, we keep in touch. They’re accessible. You can reach out to anyone,” he says. “I had come from engineering, so I was taught to be data driven—that there was one right answer and you had to be exhaustive to make sure you got every detail right. At Tuck, you unlearn that. You learn about what’s important, what’s salient, so you can make decisions without data, with incomplete information. That’s not a skill that’s taught to an engineer.”

Post Tuck, he worked in management consulting during the era when the Internet was just getting started, before transferring to banking as a research analyst at a financial security firm, covering the mobile and telecom equipment industries. But in the back of his mind, he still had the idea that he wanted to create something himself.

He had moved to California’s Bay Area, where he became interested in the area’s wine scene in Napa and Sonoma counties. When he realized it was next to impossible to order and ship wine across state lines, the idea for his first startup came to him. “I knew shipping wine would be challenging and not just from a regulatory point of view,” he says. “It was a hard problem, but I always like to solve problems. To create sustainable competitive advantage, you’ve got to solve hard problems and get way ahead. The hallmark of what I tried to do with my companies is to fix something that’s broken. It’s harder to win but if you do win, the rewards are greater.”

So, he spent six months talking to customers, wholesales, retailers, and winemakers to understand the challenges.

Then he wrote a business plan straight from the structure he learned in Tuck’s entrepreneurship class. His company, then called Wine Shopper, partnered with 200 licensed wine distributers across the country and became the first to legally ship wine to more than 11 states. After raising $46 million in funding from Kleiner Perkins and Amazon, Wine Shopper was purchased within two years by Wine.com.

Sisson launched three subsequent companies after that—a media production company called Mixonic that was acquired in 2017, a click-to-call technology company called Teleo that was acquired by Microsoft in 2005, and Line2, the first company to get a full-service phone app approved by Apple, which was acquired in 2018. After that, he came up with the idea for Yaza.

Mentorship has been a key part of Sisson’s identity through his career. He’s mentored startup founders at the European Innovation Academy and StartOut Growth Lab, where he’s helped 25 companies close on more than $30 million in funding and created more than 140 new jobs. “Having had 20 years of starting companies and making mistakes along the way, I have a lot to offer as a mentor,” he says.