Recently those five winners joined us for a one-day Seller Summit at our San Francisco headquarters, where they were mentored by business luminaries and got to meet with experts who addressed some of their most pressing issues.
Sarah Friar, Square’s CFO, kicked off the day by welcoming our winners:
Boba Guys — A bubble tea shop where the drinks are made with organic milk and loose-leaf teas. Starting in 2011 as a pop-up shop, Boba Guys now has five stores in San Francisco and two in New York.
Iconoclast Dad Bags — A line of stylish, masculine, functional, hands-free diaper bags for dads. Founded by a retired LAPD officer, the company donates a portion of sales to nonprofits that facilitate after-school programs in Los Angeles.
PREP Cosmetics — The first and only dermatologist-founded skin-care line for girls, created by a dermatologist mom to educate girls about the importance of skin care. Based in Texas, the company also leads weekly girls’ empowerment workshops.
Smack Dab — A Chicago bakery that sells amazing pastries and locally roasted coffee in unexpected spaces and underutilized locations. Smack Dab cultivates the professional success of its highly diverse staff, focusing on providing women, people of color, and transgender folks opportunities to learn and thrive in a safe environment.
The Other Side Movers — Staffed and operated by ex-offenders and former addicts who have committed to changing their lives, this moving company is based in Salt Lake City. It provides outstanding customer service and offers its employees valuable real-life vocational training.
Following introductions, our business owners got to sit down and pick the brains of business luminaries: David Viniar, the former CFO of Goldman Sachs and member of the Square Board of Directors; Roy Choi, chef and restaurateur; Reshma Saujani, founder and CEO of Girls Who Code; and our own founder and CEO, Jack Dorsey.
During sessions throughout the day, our business owners got to ask these pioneers questions about everything from management to creativity. A common theme across all sessions was growth: when should you expand and how do you know it’s the right time?
David Viniar advised the winners that growth is important, but you should strive for growth at a measured pace because the new things you take on are always more difficult than you expect. Talking about business diversification and expansion, he also referenced a friend who told him that “more companies die of indigestion than starvation.”
Jack Dorsey echoed Viniar’s advice to be patient. He noted that small teams can do really big things, so rushing into growth isn’t always the right move. He recommended moving toward what feels right, but taking the time to prove that it would work.
Roy Choi referenced a personal experience: He wanted to keep the staff of his food truck, Kogi, small and do everything himself. But when his coworkers forced him to take a look at the thousands of people waiting for his food, he knew it was time to let go and get more people on staff. At the same time he also cautioned the business owners to take a slow and methodical approach, warning that quality can suffer if you grow too fast.
Choi also spoke to another theme in the sessions — management and delegation. When asked when he would advise passing on the day-to-day management of a business to employees, he recommended that our winners train people they trust but stay involved every day.
“You can’t ask people to work for your business and try new things if you aren’t doing it beside them,” he said.
Viniar also talked about the importance of finding direct reports whom you really trust and then delegating managerial oversight. Again, he recommended our winners be patient about hiring, to take time and do the work yourself until you find the right person for the job.
Reshma Saujani spoke with the business owners about the importance of storytelling in building brand and awareness for their businesses. Her own nonprofit, Girls Who Code, uses the stories of girls who build incredible things to communicate the organization’s value.
“We tell these stories up front,” she said, while encouraging the winners to think about how to show how their own businesses are changing lives and solving problems.
In addition to these mentorship sessions, we paired our winners with experts that could help them work through big projects or challenges they were facing in their businesses.
Job-listings site Indeed joined us to talk about best practices for hiring when you are trying to grow quickly. Digital marketing agency 3Q shared its insight on digital advertising for brand growth. Google stopped by to give some pointers on how to get the most out of search. And our own experts from across Square met with the winners on a variety of topics.
We ended the day with a dinner where the winners got to share what they’ve learned from their own businesses.