My Journey from GSEA Global Finalist to Digital Nomad

At Entrepreneurs’ Organization (EO), our vision is to build the world’s most influential community of entrepreneurs. One way we encourage young entrepreneurs is through the EO Global Student Entrepreneur Awards (GSEA), EO’s premier competition for students who own and operate a business while attending college or university. The intense, international competition culminates with the Global Finals, where “studentpreneurs” from 50+ countries compete and make connections with both seasoned entrepreneurs and their fellow competitors.

Many GSEA participants go on to grow their businesses through EO Accelerator and eventually graduate from the program and become EO members. Tyler Olson is one such GSEA alumni. A global finalist in the 2007 GSEA competition, he is now an EO Minnesota member who owns five businesses.

We asked Tyler about his experiences. Here’s what he shared.

Tell us about your entrepreneurial journey.

It all started when I was 12 years old. The family next door mentioned they needed a teenager to fix their computer. I said: “Well, I’m not a teenager yet, but I’m sure I can fix your computer!” My computer repair business, named HelpMeTy―because that’s what people would often call me and say―was born. Through middle school and high school, I started several other businesses and kept growing the computer repair business.

In 2007, I competed in GSEA, starting with a local competition in Minnesota; from there I made it all the way to the Global Semifinals. At that time, I was a junior at the University of St. Thomas, had just turned 21 years old, and had about US$300K in revenue, with several technicians fixing computers both on-site in Minnesota and remotely around the world. My strategy was to hire technicians with well-rounded personalities, which helped differentiate us from typical computer geeks who couldn’t speak in layman’s terms to people who wanted to understand what was being done to fix their computers.

Where are you now?

My motivation for becoming an entrepreneur was the ability to do anything, anytime, anywhere, with anyone. Attaining that complete freedom has always been the reason I’ve worked so hard.

I took a huge risk this year: I fired myself as CEO of my primary company and sold my condo. I’m at a point with my businesses where I can work remotely and a time in life when I can travel frequently, so I’m living and working out of a backpack.

I’m loving every minute of my new digital nomadic lifestyle. Technically, I am unemployed and homeless, working on my next business from a coworking space in Bali.

I own five companies, all in various technology industries including social media, the sharing economy and cybersecurity:

1. Modern Foundation is a social and search marketing consultancy with about 15 people.
2. Away Agents is a short-term rental management company helping homeowners and real-estate investors earn higher incomes.
3. My car rental company utilizes Turo as a platform―it’s similar to Airbnb, but for cars.
4. I’m an internationally recognized speaker on topics such as social media, cybersecurity and motivating young people to become entrepreneurs.
5. SHYLD’s mission is to increase the collective safety of all by eliminating the cybersecurity talent gap.

Tell us about your GSEA journey.

GSEA is a life-changing experience. From my perspective, it’s the world’s most well-known, respected and influential competition for student entrepreneurs.

Being surrounded by other student entrepreneurs from around the world who have a similar level of passion, trust, respect, a thirst for learning, the desire to Boldly Go and Make a Mark, and who are genuinely cool people―is simply awesome. It’s hard to find those people on your own, yet, they’re everywhere around the world within GSEA. Most GSEA alumni will say they “finally found their tribe” through GSEA.

The actual competition stirred up all sorts of emotions―excitement, adrenaline, anticipation, the desire to win, awe for my fellow competitors, humbleness, pride, connectedness, but most of all, happiness.

What’s your favorite GSEA memory?

A group of us were sitting in a hot tub at a GSEA alumni event at Lake Tahoe when the GSEA winner from Sweden asked: “Why do Americans use credit cards?”

I responded with the big three: Cash flow, simplicity and rewards.

“What rewards?”

Well, some credit cards give you one to two percent cash back when you spend money with them.

“Wait, are you telling me that if I spend US$30 million a year on Google AdWords for clients, that I could get US$300,000 in cash back!?”

Probably. It’s worth exploring!

Three weeks later I got an e-mail: “Thanks Tyler, it worked! I think that idea will increase my net income by hundreds of thousands of dollars this year!”

Great things happen when like-minded entrepreneurs get together! Competing in GSEA was one of the top five most valuable experiences of my life, for many reasons. I continue to donate my time as my EO chapter’s GSEA Chair to help ensure future generations have a similar or even more valuable experience than the one I had.

What is the coolest thing you’ve experienced as a result of being an entrepreneur?

I’ve had so many amazing opportunities; it’s hard to choose between dogfighting in a fighter plane, training with the SWAT team, speaking on a panel in Germany alongside the undersecretary of cybersecurity for the US Department of Homeland Security, or finally achieving my dream lifestyle of traveling the world. All of these experiences are directly tied to the opportunity of competing in GSEA, joining EO Accelerator, and ultimately becoming a member of the Entrepreneurs’ Organization.

Being an EO member is the best investment of time and money I’ve ever made―nothing else even comes close to second place. I’ve found many friends, mentors, travel buddies, sales opportunities, investors, and life-changing experiences during my years in EO. 

Describe your journey from GSEA to joining EO.

It’s been a remarkable journey. In 2007, I competed in the GSEA Global Finals and afterward was encouraged to join EO Accelerator. I came back to Minnesota, immediately joined Accelerator, and connected with one of my GSEA judges, Shane Erickson, as my Accelerator mentor. Shane has been one of the most influential people in my life. I learned a lot and applied that knowledge to my company and then, in 2014―six years and one business later―I met the financial threshold and finally joined EO. Since that time, I’ve made many extremely valuable relationships with EO members around the world.

Being an EO member is the best investment of time and money I’ve ever made―nothing else even comes close to second place. I’ve found many friends, mentors, travel buddies, sales opportunities, investors, and life-changing experiences during my years in EO.

Have your goals been influenced by your participation in GSEA?

Yes, absolutely! Not only have they been influenced; in many ways, my participation in GSEA set the course for my entire entrepreneurial journey.

I was fortunate that Michael Sarafolean, a long-time EO member, was my professor for the very first course in entrepreneurship that I took at the University of St. Thomas. Michael shared a potential path with me that involved creating my first business plan and applying to the GSEA competition. He even mentioned the possibility of going from GSEA to EO Accelerator and then ultimately joining EO. Michael knew I was a doer, and thought I might find the elements along that path rewarding, valuable and fun.

He helped me craft that business plan and I entered GSEA, and it opened up a new world of possibilities. GSEA definitely helped me realize that I needed a broader and more global mindset.

Around that time, I created my first personal vision presentation. I’m a strong believer in the power a detailed visual vision, so you—and others–can see what you want to accomplish in coming years and then work backward from your goals to place milestones to get you there. That personal vision presentation became my list of goals that I’ve pursued in the 11 years since creating it.

I’m a couple of years behind my goals as established at age 21, but having that vision presentation motivates me to continue working hard. I’ve accomplished far more from working toward those goals than I would have if I’d never created them.

I ask everyone who works for me to create a personal vision presentation and share it with the team. It’s a lot of work, and some people hate doing it, but after they’ve finished it and present their vision to the group, most people thank me because they, too, find it very motivating.

My entrepreneurial journey has been a fantastic ride and keeps getting better. As I share my story in speaking engagements, I emphasize what a major role GSEA and EO Accelerator have played in providing me with the tools and strategies I needed to achieve my goals.

And I’m not done yet!