From Tech Startup To Sustainable Pig Farming: How 3 People Left It All Behind

Would you leave Google to make chocolate? Why these three people took the concept of digital detox to the extreme.

From Tech Startup To Sustainable Pig Farming: How 3 People Left It All Behind
[Photo: Flickr user Cameron Nordholm]

I was sharing a cup of coffee with an friend who once worked on the forefront of new media when he pulled out his flip phone. I gasped. He gave a sheepish grin and explained that ever since he left his job in tech he really didn’t need to be responding to emails and checking social media constantly.


He isn’t the only person redefining his relationship to technology. The more our lives become defined by tech, the more the concept of a digital detox becomes appealing.

We asked three people who left their technology-saturated jobs for a more analog life what it takes to leave the screen. Aside from the pig farmer, who now holds her product meetings in the barn, no one is looking back.

From Google to Chocolate

When Greg D’Alesandre left Google after six years, he made the leap to a passion project: chocolate. He now sources chocolate and visits farms around the world (and fixes the roasters when they aren’t working). Founders Todd Masonis and Cameron Ring started Dandelion Chocolate as a hobby when they started roasting cocoa beans in their garage after selling their startup, Plaxo, to Comcast.

“It’s hard to leave, especially when all of your friends think you are crazy for leaving a job that is lucrative and fun and at the height of your career . . . It’s a tough mental place to be in and easy to second-guess your choice.”

When D’Alesandre started looking for his next career move, he had one clear deal breaker: “When I interviewed for jobs I always asked if people were happy there. Often I would hear it pays well or there are good benefits, but that’s different than happy. And when I looked at what I wanted to do next, I wanted to work with happy people.

Photo: Flickr user
Daniel Zemans

D’Alesandre was clear that identifying his priorities helped bring clarity. “You need to understand what is important to you. Is it about money and the title? I think I was lucky. Silicon Valley is influenced by the Stanford culture where success seems to mean opening your own company. I went to Brown where it felt like success meant saving the world.”


His best advice: “The Dude Abides. People are capable of adjusting to anything: more money or less money. The unknown is the scariest part. Change won’t kill you. It’s just different.”

From Film Editing to Wildness Guide

Clementine Wilson went to film school because she wanted to work in the film industry. She started working as a film editor at a news media company right away, and as a result, her day-to-day activities involved spending 12 hours alone in dark room in front of multiple screens.

“I was watching other people’s lives unfold, piecing together their stories, and being a part of their adventures through telling their story. But I was beginning to feel lonely and sad: What I was yearning for was to have my own experiences.

So when I heard my friend talk about her work as a guide at a wilderness treatment program with youth at risk, I felt a calling. I left behind a well-paying job in San Francisco and took a lot of risks to move in that direction, and things didn’t work out right away. Even when everyone around me didn’t understand my choices I kept following that pull . . . I guess you could say I answered the call to my hero’s journey.

Her best advice: “You can stay stuck in something and stay safe, but staying safe isn’t always life affirming.”

From Tech Startup to Sustainable Pig Farming

Tina Fitch’s travel startup Switchfly was generating 1.2 billion in bookings per year when she left it and Silicon Valley behind to raise pigs on Maui. “I wanted to have the best of both worlds; I didn’t want to wait until the end of my career to enjoy the different passions in my life. I was originally from Hawaii, and wanted to raise my kids in a rural environment because of the work ethic, values, and lack of materialism. After working in finance and tech startups my entire career, I wanted to do a startup in something more tangible and that I could do with my family and would benefit my community.”

Photo: Tracy Leboe

Fitch says that Michael Pollan’s book, The Omnivore’s Dilemma, and the documentary Food Inc., had a major impact when she was considering her next career move. She and her husband became interested in the state of the food industry, and the subsequent impact on people’s health, and decided they wanted to create a different model of small-scale farming.

“I wanted to fulfill a more humane life mission . . . and wanted to show that treating animals with respect, kindness, and managing land for optimal environmental sustainability is not only the right thing to do, but also produces a far superior product. I also wanted to provide a model of humane agriculture that could influence others.”

Fitch isn’t done with being an entrepreneur, and recently launched hobnob. “We had the first product design meeting in the barn, overlooking the pigs on pasture.”

Leah Lamb is a writer and storyteller based in the Bay Area. She consults and gives workshops about how to foster creativity into the workplace.