What’s Your Side Hustle?

Taste, Passion, and Inspiration at the GUILD

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On the table

7 min readMay 5, 2017

Layne Gray, host of the GUILD’s Taste and Passion event at the illy flagship caffè this week in San Francisco, is a serial entrepreneur with as many passions as talents. There is the business Layne: she was a tech executive and continues to be an active angel investor. There is the entrepreneurial Layne: the published author, event producer, and oenophile. And there’s the socially generous Layne: the philanthropist, volunteer for the Junior League and the SF Ballet, and a dedicated mentor to young career women. All three Laynes made her the perfect guide for an evening of sharing wine, chocolate, and inspired conversation about our passion projects, or side hustles.

side hustle (n): a way to make some extra cash that allows you flexibility to pursue what you’re most interested in. It can also be your true passion — a chance to delve into fashion, travel, or whatever it is you care about the most, while deciding whether to quit your day job.

Early in her career as an executive at Oracle, Layne discovered she could marry her marketing and project management savvy with a knack for event planning. She was soon running her own business hosting corporate conferences, product launches, and seminars for technology industry clients worldwide.

“I never wanted the job that I did for six days a week, 12-plus hours a day to define who I was,” Layne says. “I wanted more out of life.”

She went on to start many other businesses, and founded Cellar & Cork a few years ago to combine two other passions: learning about wine and enjoying time with friends.

The San Francisco Hustle

Turning a side interest into a job is becoming an increasingly popular career trajectory here in the Bay Area. San Francisco enjoys many unique characteristics that make it the perfect proving ground for realizing your passion project.

“For one thing, there’s a healthy culture of meritocracy. Here, it’s not so much about where you were educated or who your family is, but rather, it’s about your aspiration, and your openness to the diverse perspectives around us,” says Layne, who added that the incredible number of events in the city makes it easy to “meet and network with people, see what they are doing and gain inspiration from them.”

Getting started has never been more accessible, she says. “As tech has become more prevalent and entrepreneurship more engrained in our culture, looking for new opportunities seems like the norm.” Tech has removed the need to open a store or to raise large funds to launch a business. A side hustle can begin as an app or easily produced product that can turn a profit without eating up too much time.

Wine + Entrepreneurs = Inspiration

Layne kicked off the lively Taste & Passion mixer by greeting arrivals at the door with a generous pour of Pie di Colle, an Umbrian Verdicchio di Matelica. The light, crisp, young wine was the perfect refresher for a balmy evening, and the airy, modern café, decorated with signature art pieces from the illy collection, was open, encouraging easy conversation. Networking flowed as we segued to a fuller-bodied, chardonnay-style Casale el Giglio Bellone, with light floral and spicy notes.

Anne Cocquyt, founder of the GUILD, a serial entrepreneur who is no stranger to side hustles, took the floor to offer some motivating insights based on her own experience:

“Use your side hustle to find balance in your work life. Experiment with your creativity, learn where your gaps are and how it feels to be your own boss. The GUILD used to be a side hustle born out of the desire to create a networking environment that’s more fun and elevated. I knew a year ago that my passion for the GUILD outweighed the security of my corporate day job and so I went for it. A side hustle can become your full-time startup if there is a big enough market to support you and your passion. It’s also OK to enjoy it for what it is and experiment and enjoy entrepreneurial freedom while your day job pays the bills!”

Anne led the room in a round of introductions, where guests shared a bit about their careers, their passions and aspirations, and reflected on their achievements, as well as how they might take their side projects to the next level.

Side Hustle Tales

“My passion project started from a sheer need: fashionable slippers for entertaining at home. I was working at Facebook, and I had become obsessed with trying to find them, and realized it was an opportunity. When I launched my product, I wasn’t sure if it would be acceptable for me to have a side hustle, so I emailed Sheryl Sandberg and asked her if it was OK to post about my new product on my Facebook page. And she was excited! She said, ‘This is fantastic, I’m so proud of you.’ Thanks to her support and encouragement, I left Facebook just over three weeks ago to dedicate all my time and attention to Birdies.” — Bianca Gates

“My main business is wedding photography. My weekly battle is not carving out the time to promote my side projects in art photography. I’m hoping to find more of a balance in my time and energy.” — Eileen Roche

“My day job is working for an HR tech and services company. I help CEOs to focus on their core business. But on the side, I organize events for the local chapter of the German Wine Society, featuring German wines that are becoming more popular in the US.” — Claudia Marcaccio

“My passion project is now my full-time project. I wanted to go the consulting route, and my passion was experiential event marketing. I wanted to work with companies and people that excited me, causes I was passionate about, people I admired, brands I felt connected to. So I gave myself a year at the last company I was working for to get things up and running, and I turned my hustle into my full-time thing. My kids are my side project now.” — Brenna Lewis

“I’m the queen of the side hustle! I’ve spent my whole life doing it. Why do one thing when you can be working on three? I’ve had a lot of projects, from selling tote bags at farmers’ markets to running a fashion camp for kids. My motivations have been to improve my financial situation, realize my creativity, and figure out what I really love to do. I’m half entrepreneur and half artist. The entrepreneur part has been a learning curve. A constant struggle to not go too far in the art direction, and not see a financial return. I’ve had an exciting transformation in the past few years and feel like I’m ready to shift. I’m proud of my successes, in making beautiful things that people get inspired by. I like creating magic.” — Western Bonime

Everyone’s story was unique, from those who were new to the concept to others who had fully realized their passions as profitable businesses. As we moved from the group back to individual conversations, there was palpable excitement in the room.

Chocolate Afternotes

Layne capped off the evening’s wine selections with a ripe, bright and tangy Bovio Il Ciotto Barbera. Its cherry character paired perfectly with the two chocolate tastings, the semisweet 75% cocoa Domori Puertomar, and the pure 100% Criollo. The end of the evening was marked by reflection and positive inspiration. Layne shared a few insights about funding a side project: “I find things that I’m especially passionate about and I move forward with them.” The difference now is that she brings “greater evaluation and trepidation” than she did five years ago, and does “a lot more research and analysis.” She also doesn’t overly self-fund.

“If a side hustle can achieve proof of concept, then other people will invest. And if they don’t invest, it’s probably not worth moving forward.”

While Layne appears the very picture of success, experience has shown she’s not afraid of failure: “Both success and failure make us substantially stronger.”