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The Mentor: Jim McKelvey Frustrated by losing a sale because he was unable to process a credit card transaction, Jim McKelvey co-founded fintech platform Square with Twitter’s Jack Dorsey in 2008. The San Francisco-based company went public in 2015 and booked $9.5 billion in revenue last year. Today, McKelvey sits on the firm’s board of directors and reportedly owns nearly 5 percent of the $120 billion company, while also running a data-sharing startup, Invisibly. He recently shared his experience building the company in his book The Innovation Stack.
The Mentee: Ali Moloo Growing up in a family of hospitality workers in Alberta, Canada, Moloo saw firsthand how disconnected and old-school the process of running a hotel can be. In 2015, he founded my DigitalOffice, a Bethesda, Maryland-based company that places everything from inventory to payroll to conveniencestore sales onto a single software platform.