20 Questions

This Pioneering Entrepreneur Shares Why You Should Study Philosophy Rather Than Business

Matthew Sweeny is the co-founder and CEO of Flirtey, the first company to conduct an FAA-approved drone delivery on U.S. soil.
This Pioneering Entrepreneur Shares Why You Should Study Philosophy Rather Than Business
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Entrepreneur Staff
Staff Writer. Covers leadership, media, technology and culture.
10 min read

Editor's Note: Entrepreneur's "20 Questions" series features both established and up-and-coming entrepreneurs and asks them a number of questions about what makes them tick, their everyday success strategies and advice for aspiring founders.

From the beginning, Matthew Sweeny’s career has been marked with firsts. The Australian-born entrepreneur was the first in his family to go to college, and it was a chance to study abroad in Shanghai that inspired what would become his pioneering company Flirtey.

While in China, he saw model helicopters, which inspired him to start tinkering with the idea of delivery drones in his dorm room. In 2013, he co-founded his drone delivery startup. After graduating from the Y Combinator accelerator, Flirtey accomplished its first major milestone.

In the summer of 2015, in collaboration with NASA Langley Research Center, it completed the first FAA-approved drone delivery on U.S. soil, consisting of 24 packages of medical supplies in Wise, Va. Since then, Flirtey has raised $16 million in funding and has worked with partners as varied as Johns Hopkins University of Medicine, Domino’s and 7-Eleven.

Sweeny says his work so far is all a part of the plan to make delivery instantaneous for whatever your needs might be, courtesy of flying robots, whether it’s dinner or life-saving medical equipment, such as the external defibrillator drone delivery initiative the company has been working on since last year.

We caught up with Sweeny to ask him 20 Questions and find out what makes him tick.

1. How do you start your day?
The typical day for me is about 9 a.m. to 2 a.m. The first thing I do is I check the news and I try to get a diversity of different opinions. I'll check liberal news, conservative news and then I'll check Reddit it as well. I find that kind of breadth of a view of the world over the past 24 hours is the right foundation for me to start my day.

2. How do you end your day?
My most productive hours are when everyone else is asleep, usually from about 11 p.m. to 2 a.m. When I'm free from distractions at that time I focus on high concentration tasks like contracts and deals with our major customers. To wind down, I usually watch documentaries.

3. What’s a book that changed your mind and why?
The Wright Brothers by David McCullough. This Book sticks with me because while it's important to be first, it's more important to win. My journey building Flirtey has been heavily influenced by the legacy of the Wright brothers. Three years ago Flirtey completed the first ever FAA-approved drone delivery on American soil and at the time I called this our Kitty Hawk moment. At that point in time, most people didn't think that delivery by drone was possible technically or possible to be approved by regulators.

That drone that did that delivery got accepted into the Smithsonian National Air and Space Museum in Washington, D.C., and is going on display alongside the Wright brothers Wright Flyer, which is their aircraft that flew at Kitty Hawk. However, the Wright brothers didn't win. I'm very conscious of building a company which not only has these pioneering firsts but it also is built with sustainable long-term competitive advantages in mind

4. What’s a book you always recommend and why?
Not a book but a letter. The letter from Birmingham Jail written by Martin Luther King Jr. During the Civil Rights era, Martin Luther King Jr. was arrested and he wrote this letter on margins of a newspaper, which was the only paper available to him. I recommend it because it's the greatest embodiment of the key principles of the Civil Rights era but also because there's a quote in there that is powerful, which is that "injustice anywhere is a threat to justice everywhere." That's an important message that is as relevant today as it was then.

5. What’s a strategy to keep focused?
Time blocking. Flirtey is at an exciting time of growth right now. We're transitioning from founder led, where I was responsible for every decision, to a company with a strong leadership team. My main responsibility is to lead the leadership team to continue to empower our growth. Time blocking is balancing between a manager's calendar, where I take meetings, and then unscheduled time that is blocked, which I call the maker calendar, where I can take deep dives into strategy work, contract work and customer work.

6. When you were a kid what did you want to be when you grew up?
I remember in high school I had an economics class. The teacher walked in and wrote on the board one word, in all caps, "entrepreneur." I'd never heard that word before. But as soon as he explained it I knew that's what I wanted to be. What an entrepreneur means to me is someone who takes the risk of trying to build something that has never been built before in a way that the people who build with you can see the benefits of the success, including through stock options in the company so that they ultimately have a piece in the value that was created.

7. What did you learn from the worst boss you ever had?
One of my first jobs was working in the fruit and vegetable section of a grocery store in my hometown in Sydney. While my boss was hardworking, she didn't care for the employees, and the lesson that I learned from that is that smart people want to work for people who have their best interests at heart. Having an awesome idea and a compelling mission is important, but it's not enough.

8. Who has influenced you most when it comes to how you approach your work?
My dad is a landscaper. He's the hardest working person I know, and growing up, his catchphrase was "have a go." I keep that consistently in my mind.

9. What’s a trip that changed you?
When I was studying at university I got a scholarship to live and study in China. I spent half a year in Shanghai and when I was there I came across the precursors to modern drones, which were model helicopters. I brought them back to my dorm room, experimented with the technology and built some of the first delivery drones. That was the start of the Flirtey story.

10. What inspires you?
I studied philosophy, so the great philosophers inspire me. The reason I chose to study philosophy was to learn how the world is and to think about how it should be. I became an entrepreneur to build bridges between the two, to try to create a society that I wanted to live in. Philosophically, it's the act of creation that inspires me.

11. What was your first business idea and what did you do with it?
When I was at university in Australia I was involved in a program called Young Achievement Australia, which was a nationwide competition for entrepreneurs. As part of this program you created a company but you had to have the most success you could within six months and then sell the company. Whoever returned the most amount of money won. I created this company that went around and interviewed the top entrepreneurs in Australia and then sold that advice to aspiring entrepreneurs. We returned a 1,000 percent profit to our shareholders within six months [by selling] the underlying intellectual property to a publishing company. We won the nationwide competition.

12. What was an early job that taught you something important or useful?
I taught journalism and American free speech at university in Australia. This was a great experience because it taught me how cultures can balance between young graduates who didn't know what is not possible and older graduate students who were more seasoned. The lesson has carried it's way through to Flirtey. The company is made up of new engineering graduates who don't know what's not possible who are working side by side with NASA engineers who are seasoned and bring great experience. This balancing act brings out the best in our engineering culture because we're a combination of fast moving, rapid prototyping engineering, combined with all levels of safety that come from having multiple NASA engineers on our team.

13. What’s the best advice you ever took?
Above all focus on your mission. Our mission is to save lives and improve lifestyles by making delivery instant for everyone. When you're in a space as cutting edge as drone delivery, there are a lot of temptations for you to focus your attention on. The advice that I've taken, which has proven very successful to us, is when deciding what framework to use to make a decision, ask the question, "Will this further the mission?"

14. What's the worst piece of advice you ever got?
I was told to choose a degree that would be marketable. But I decided not to. I decided to study philosophy instead of commerce because I believed that it would train my mind to be an entrepreneur instead of train myself to be an employee.

15. What’s a productivity tip you swear by?
I optimize my diet to optimize my productivity. I choose meals that enable me to maintain the highest degree of concentration and focus.

16. Is there an app or tool you use in a surprising way to get thingsdone or stay on track?
Trusty old pen and paper. At the beginning of each day I write down the three major goals I intend to accomplish that day and I find that keeping regular lists in pen and paper format is helpful for driving productivity.

17. What does work-life balance mean to you?
I'm not familiar with that phrase.

18. How do you prevent burnout?
I try to set aside Saturdays to relax. I'm lucky that we are based in Reno and I've got Lake Tahoe in my backyard, whether it's hiking or just enjoying a meal on the water, that's my favourite way to relax.

19. When you’re faced with a creativity block, what’s your strategy to get innovating?
I listen to one of the two greatest artists of all time, either Mozart or Eminem, combined with tea and coffee.

20. What are you learning now? Why is that important?
I'm currently learning to delegate. We're in a phase of hypergrowth and it's important for me to empower my leadership team to make decisions so that I can focus on scaling the company.

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