Alumni Spotlight: Josh Gershon, founder of Startup Island
My name is Tyler Citrin and once upon a time I was an entrepreneur. I was never a fan of writing, but I thrive on conversation and have been extremely fortunate to speak with many different entrepreneurs about what they’re doing. I have a feeling this will become a trend along the way.
I am excited to introduce you to an Indiana University alumnus and friend, Josh Gershon. Josh is the founder of Startup Island, a “personal development accelerator, designed to connect entrepreneurial-minded students and young professionals, through a travel experience.”
Check out below to hear his full story and if you’re interested, reach out to Josh at josh@joinstartupisland.com!
How did you come up with the idea?
I came up with the idea for Startup Island in May of 2015, when I was at a crossroads in career. I had been with a food-tech startup for the last 18 months, and while I enjoyed the experience and the growth I was witnessing, I was starting to lack fulfillment in my day-to-day. So I gave myself two options, buy a one way ticket to Costa Rica and backpack for 6 months, or switch career paths and take an immersive course in graphic design.
My heart wanted to travel because I knew deep down, that this would be a tremendous personal growth experience. My head was telling me to pursue career advancement in a more direct way. So I found myself grappling with the choice between personal development, or professional development. That was when I decided to create a program that would provide it’s participants with both. Personal growth through adventure and exploration, while surrounding yourself with mission-driven, innovative people with whom you can exchange ideas and resources to create a meaningful career path.
How’d you end up where you are today?
After I conceptualized the idea of this program I wanted to create, eventually I found myself in the process of building Startup Island. I had little experience and industry knowledge at the time, but I put together a website, Facebook group, Instagram page and just started telling people that we host travel experiences for entrepreneurs. There was a lot that was undefined at that point, until October 2015, when my co-founder (and one of my childhood best friends), Brian Helfman, came on board. He helped refine the vision into action, and we decided to focus our first few trips on college students, positioning ourselves as an alternative spring break for entrepreneurial students.
We wound up getting our first trip off the ground in three months, and have been slowly but steadily picking up steam ever since. We’ve now hosted 7 trips for 107 travelers, 17 of whom have already come back two or three times. This year will be our third year doing spring break in Costa Rica.
What’d you do while in school?
I was an arts management major through SPEA, but to be quite honest, I didn’t get much out of the classroom. It was my own fault, but I really only cared about doing well enough to keep a mid-high 3.something GPA…other than that, I just wanted to have fun with my friends and watch the hoosiers play basketball.
BUT, where I did learn a tremendous amount, and what I most attribute my passion for entrepreneurship to, was my time working for btownmenus.com, during my four years at school. Mike Rolland (founder) became a mentor and good friend of mine, and I was fascinated watching Btownmenus grow into a massive success. I was also surprised that the work I was doing, was actually driving growth and engagement to the business. I realized then, that we as students can take action and build businesses…we didn’t have to wait until we got into “the real world.”
What classes or university resources helped the most?
Knowing what I know now, and based on how much entrepreneurship has grown on college campuses, I would have leveraged all and every resource I could find on campus, if I had the chance to do it again. For me back then, I just relied on my own guess and check methods, learned things by testing them at Btownmenus, and was well-guided by Mike and the rest of the leadership team as we built the company.
What did you learn at school and on the job?
Learn by doing was my key takeaway, but again, I would have done things differently if I could go back to school. As a student, it’s a rare time in your life, where it is your JOB to learn as much as possible. I’d advise any young entrepreneurs to seek out as much knowledge as possible — in the classroom, out of the classroom, by building relationships with your professors, etc. Don’t just study to pass the tests, learn the things you WANT to learn, and care about learning, because that is the stuff you’ll use to innovate.
Who inspired you along the way?
As a Hoosier, I’ve always been a big fan of Mark Cuban. But in my own life, as I mentioned, Mike was an early role-model. My uncle who is an entrepreneur has always been a role model.
Outside of that, I always admired and was fascinated by digital nomads…people who left the corporate life (or never entered it to begin with) to pursue a life of location-independent work. It always just seemed as though they were living such more meaningful, and freedom-based lives.
Any advice to future entrepreneurs?
As I mentioned above, LEARN. If there is something you are interested in, even if it falls way outside your major, or is something that may seem completely irrelevant to your “career path,” if you’re interested in it…find a way to learn about it. Being interested makes you interesting.
Try as many different jobs, classes, majors, various experiences as possible. Don’t assume that you are going to love the first thing you tell yourself you want to be when you grow up. Learn by trying, failing, and trying again.
Surround yourselves with people who lift you up, challenge you, and inspire you.
Do things that scare you. This is the hardest one, because nobody likes to be uncomfortable, but when you get through that discomfort and land on the other side, you will find immense growth.
Thank you for taking the time to share your entrepreneurial journey with the StartupIU community, Josh!
About StartupIU
StartupIU is an initiative built and managed by the Shoemaker Scholars that seeks to grow Indiana University’s community of changemakers, innovators, and entrepreneurs. If you want to stay in touch with upcoming events, news, and opportunities in the community, become one of the over 1000 students on our email list.
