When Matthew Mottola MSEL’17 was looking to move, his primary concern was simply time. Having lived on the other side of the world in Singapore, working on his startup, he was eager to relocate somewhere in the Eastern time zone.
So, with an aunt living in South Florida, he decided to check out Miami. He was immediately smitten. He first fell for the city’s immigrant restaurants and coffee shops. “The weather is nice,” he says, “but I really fell in love with the culture.”
More than that, though, Miami offered him a peek at the future, most specifically about how we work. With its energy and innovative spirit, Miami is full of entrepreneurs, freelancers, and remote workers. Mottola has met many people who work for themselves and who are drawn to the city’s entrepreneurial atmosphere. “I’ve had meetings with people who have moved from San Francisco and New York and are looking to stay,” he says. “The whole city is saying, ‘If you are in tech or are a remote worker, we want you here.’ ”
The city is an ideal place for Mottola, whose career has focused on supporting and empowering freelance and remote workers. At Microsoft a couple of years back, he led efforts to create the Microsoft 365 Freelance Toolkit, a suite of tools for companies to manage their contractors. In March 2020, he launched Venture L, a platform he co-founded that assists freelancers in running and scaling their businesses.
And, this past January saw the release of a book he co-wrote: The Human Cloud: How Today’s Changemakers Use Artificial Intelligence and the Freelance Economy to Transform Work. Published by HarperCollins, the book explores how technology is rapidly altering how we make a living, with more and more people drifting away from traditional desk jobs.
Such drastic change can be unsettling, but as he lives and works in the sunshine of Miami, Mottola sees the promise and potential of technology that enables freelancers to work independently from wherever they want. “Like everything with technology, it’s not good or bad,” he says. “It’s how we decide to use it.”
Mottola wasn’t always such a champion of the freelance life. He once was an accountant for Ernst & Young, and his future, a seemingly safe and predictable career path, was laid out before him. He didn’t like what he saw. “I was on the path I was supposed to be on, but I knew it wouldn’t work for me,” he says.
What bothered him was a lack of autonomy, the same lack of autonomy he had watched his parents struggle with when he was growing up. Mottola didn’t relish not being in control. “If they wanted to fire me, they would. If they wanted to lay me off, they would. I couldn’t stomach that,” he says. “I wanted to understand how work can be positive. So many people seemed miserable in what they did. You have to make money, but how do you do it in a way that fits your life instead of taking over your life?”
In freelancing, he found control over his career, and he saw a life where people are judged, not by any superficial office politics, but solely on the work they do. “Control is the number one thing,” he says. “It is control to pick my clients and pick the projects I want to work on. I have control over the path I want to create.”
Through his career, he has not only created that path for himself, but also helped other freelancers to do the same, particularly as technology has made that path a more intriguing one to navigate.
If Miami offers a glimpse of the future of work, so does the pandemic. Seemingly overnight, millions of people began working from home, a turn of events that shattered preconceived notions that many companies long had held about remote work. “They thought you had to be within the walls to get the work done,” he says.
Of course, many people already were working from home before we ever heard of COVID-19, but the pandemic dramatically accelerated the trend. “What is happening today is something I hadn’t expected to see in five years,” Mottola says.
“I wanted to understand how work can be positive. So many people seemed miserable in what they did. You have to make money, but how do you do it in a way that fits your life instead of taking over your life?”
Matthew Mottola MSEL'17
Not that everyone is as enthused by the future of work as Mottola is. Tell someone they may one day need to work as a freelancer, and they may lament the lost peace of mind that comes with a steady 9-to-5 job. Mottola understands. “You wake up and are hustling for gigs, and that’s horrible,” he says.
When he envisions the future, however, Mottola doesn’t imagine harried and isolated contractors constantly pounding the pavement for assignments. He imagines freelancers who build valued relationships with each other and with clients, and these relationships are what lead to successful careers.
Helping to build those relationships is Venture L, which allows freelancers to join together as a group, providing them with community and the opportunity to compete against large creative agencies for more lucrative projects.
“We can go toward a gig economy, or a relationship economy,” Mottola says. “Relationships are the glue. A project ends, but the relationship never does. It all comes down to the relationship at the end of the day.”