Nomad City 2019

Gathering together experienced speakers and hundreds of attendees from all over the world, Nomad City unites remote minded individuals and companies in a melting pot of ideas and knowledge about the future of work. See what we got up to last year…

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Las Palmas de Gran Canaria, 6th – 8th, November 2020

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Nomad City

The Nomad City 19 Chats- Matthew Mottola

Introducing Matthew Mottola, the Lead of Growth for Microsoft’s 365 freelance toolkit and one of the keynote speakers at Nomad City 2019.


Before joining Microsoft, Matthew was a freelancer and an entrepreneur, building a freelance platform that connected students to small businesses, and launched a signature go-to market offering at Gigster, one of the fastest growing players powering the Gig-Economy. His experience brought him to his current place, having built and continuing to lead Microsoft’s 365 freelance toolkit, which unlocks and embraces freelancing at enterprise scale. He guest lectures and helped developed the entrepreneurship curriculum at Georgia Tech, along with delivering product-first insights through advising, writing and speaking. He is the author of StartUp Not StartDown, and upcoming book Our Big Leap Forward, and you can join him at Nomad City 2019 for his keynote about Streamline Scaling with Freelance Talent.

We took a few moments with him to learn more about what makes him click professionally, what his opinion is on the future of remote work, and much more.


What’s your remote story? 

I always worked this way, and thought it was normal until I had to grow up and get a “real” job. As a student I freelanced, doing mostly market research for small businesses and startups. I also started a couple businesses, and thought virtual project based work was the way everyone wanted to work. 

But inevitably I had to get a real job, and since I majored in finance and accounting, my path was the Big 4. Yet when I got there, I was appalled by how bad it sucked compared to my life as a freelancer. While the first couple weeks had the allure of being on the 32nd floor of a highrise in Boston, it quickly turned into dread of going to the same place every day for 8 hours. And the actual work didn’t make sense. People didn’t love the work they did. Nor really care about the actual work. It was just get in, get a paycheck, get out, the opposite of my experience in freelance and startups. 

So instead of following the traditional path, I stuck with freelance, and now lead a product at Microsoft enabling our customers to embrace freelance talent in their workflow. 


What’s your favourite place to work from?

My coffee shop back home – Plum Island Roasters. It was a small little coffee shop shack right on the water. Pure paradise. 


Can you share with us a failure of yours that later turned out to be a learning moment?

Too many to count. My first startup was an epic failure. We did everything wrong – tried to raise capital with no customer validation. Built pitch decks instead of a product. But as it was in the freelance space, it taught me the mechanics of the industry, and showed me a world where you can make an impact through the work you do. As a four person team highly leveraging freelancers ourselves, it also taught me how to run fast moving, and fast pivoting teams 100% digitally through teams like Trello, Slack, and G-Suite. 


What does your workday usually look like? 

Get to the coffee shop at 6. Do deep work until about 9, then open up my computer to the world. I usually start by answering emails, or meeting with customers, or internal teams. Then around 11 I go for a walk, catch up with friends, or something that’s not work. Then from about noon until 3 I’m either back to deep work or still in meetings. Monday, Tuesday and Friday I load up my meetings and am in the office, so most likely I’m in meetings from 9-5. Then Wednesday & Thursday I try to keep my day focused on deep work. So I’m at the coffee shop, or bouncing around coffee shops all day. So from noon until three I’m back to deep work. Then I’m feeling pretty tired, so I usually go for a run or workout (get my energy up)! Then eat, and either see friends, work, whichever is highest priority. 


Do you have any particular practices that help your through periods of work difficulties?

Exercise is my go to. Whether to get energy, or give me the cognitive space to think.

I also work on being very intentional with my time. What I noticed in an office, is you get disrupted about every 13 minutes. Whether someone popping in to ask a question. Or say a joke. And by the end of the day, you realize you’ve done a whole lot of busy work, but no work that you need to move the needle. To combat this, I look to going into the office as a place to socialize, learn and meet- not a place to get work done. 

What is something you wish more people knew about being remote?

For some people, the office is tiring. If you’re introverted, the idea of being around people that you’re supposed to talk to for eight hours a day is pretty close to hell. Ironically, trending on LinkedIn as we speak is “The awkwardness of work socializing”. Instead, in a remote environment, you can be intentional with your time, and intentionally build deep relationships. For example, in the office, unless you’re a hermit in your own office, it’s most likely 8 hours of spontaneous stimulation – super draining and surface level. Instead, in a remote environment, you can be 100% flow for three hours in the morning, then 100% social during lunch – building much deeper relationships.


What do you think people should focus on the most when venturing out to become remote workers or entrepreneurs?

What are the 20% of tasks that drive 80% of your results, and build towards those 20%. It may mean you don’t answer an email within 20 minutes. That’s okay!!!!


What’s your favourite perk of remote work?

Choice. The ability to run at 11 am if the sun’s out. Or to take a call at 4 am if it’s a European client, work until around 10, then get a nice brunch.


Any last words you would like to share with the Nomad City community?

With opportunity comes responsibility. We have enormous opportunity to rewire how we work. With this opportunity, comes a responsibility to make sure it works for everyone.


Thank you Matthew for your time, and for everyone else, see you in 7-9 November in Las Palmas de Gran Canaria!