Resource Spotlight: Startup Island

Jun 4, 2017

Resource Spotlight: Startup Island

Jun 4, 2017

This week we speak to Josh Gershon, Co-founder of Startup Island, a pay-it-forward community of entrepreneurial-minded explorers who seek to learn, grow and venture out of their comfort zones. ‘When we travel together, we strive to help each other build products, elevate our ideas, find strategic partners and simply GET STUFF DONE.’

GH: What is Startup Island?

SI: Startup Island is a program designed to connect entrepreneurial-minded college students and young professionals, through a shared travel experience. We offer both weekend and week-long retreats, taking place at unique and inspiring locations throughout the U.S. and Central/South America. Each of our trips consists of group workshops, mental and physical activities, individualized coaching sessions, and meeting local entrepreneurs in the places we visit.

GH: What is your name and role?

SI: Josh Gershon, Co-Founder and Chief of Vision

GH: What was your Eureka moment: how did Startup Island get started?

SI: I had always been entrepreneurial-minded and worked for a student-founded business throughout my four years of college, which was a huge inspiration for me. Following graduation, I launched my own business (which failed), and then lived in a few different cities, working a range of odd jobs, from waiting tables to managing a surf shop. Next I got a job in NYC and worked my way up with a growing startup. After about two years, I wanted to shift from sales to something more creative. I had always been interested in graphic design, so I was thinking about taking a three-month immersive course and re-enter the job market as an entry-level graphic designer. On the other hand, I always had the travel bug and thought it might be the perfect time to buy a one-way-ticket to my favorite place (Costa Rica) and backpack around the country until my money ran out. I knew this wouldn’t be the best move “on paper,” but it would be the most valuable learning experience I could give myself. It was at this moment, having to choose between personal development or professional development, when the idea for Startup Island was born – I would create a travel program which catalyzes entrepreneurial and career growth, while offering a life changing and eye-opening travel experience.

GH: How did you build your team?

SI: Brian has been one of my best friends since middle school, and we always used to share business ideas with each other. We also always thought it would be cool if one day we started something up together. At the time when Brian was sort of winding down his first business, we would discuss Startup Island more and more. It became clear that we were meant to build this together. When I was on my own, I basically had an idea. As soon as Brian came aboard, it became a business. He essentially took the idea and said, “ok, let’s make this happen.”

Abbey, our newest team member, is one of our first ever trip-goers. She was the first person I’ve ever “sold” a Startup Island trip to, and from the very first phone call we had, I could feel her energy and passion for entrepreneurship. She’s been our unofficial hype-person since day one, and it only felt right to make that official after our last spring break trip.

GH: What is your company philosophy driving your company culture?

SI: In a word, connection. We believe that entrepreneurship is about being the CEO of your life, not just a business. Therefore it’s about finding a true sense of connection to the work you do, the people you surround yourself with, your community, the environment, and YOURSELF in general. We are so deeply connected to our mission (to cultivate more connection), it drives everything we do. Internally and for our community members.

 GH: Startup life is full of failures and ‘make it work’ moments – can you identify how you bounced back from one of yours?

SI: I think failure itself is a perceived failure. When really it’s a learning opportunity. I did a lot of things wrong the first time I started a company…too many to talk about for the sake of this interview. But every single one of those mistakes was also a gift saying, “here’s how to not do this next time.”

Not to say we haven’t made our fair share of mistakes with Startup Island as well, but simply the act of starting another business and believing that this time we will succeed, was an act of bouncing back from a previous failure.

GH: What did you learn from your first students?

SI: An insane amount, but probably the biggest takeaway was that our “product” is the connection among our travelers. Initially it was difficult whether we should position ourselves as a personal development or entrepreneurial development program. Are we a bootcamp? An accelerator? We weren’t sure what to call ourselves. Seeing the connections that our students formed, and in just a week’s time or less, showed us that we are a platform for forming indescribable connections…which has profound effects on business AND life.

Do people leave with MVP’s? Yes. Have some amazing product ideas formed and been enhanced? Absolutely. But what we can guarantee and are most proud of, time and time again, is entrepreneurial-minded people, people who are born to do amazing things…finding other people to support them along the way and enjoy the journey with them.

GH: What has the Boston ecosystem provided you?

SI: Our entire business 🙂

Without the amazing student-entrepreneurship and startup ecosystem in Boston, I have no doubt we would not be where we are today. Special thanks must go out to Ben Bungert and the Northeaster Entrepreneurship Club for being so receptive and embracing us from day one. They are the reason anybody in Boston knows who we are and were instrumental in helping us get our first trip off the ground.

GH: What is the Boston ecosystem lacking from your perspective?

SI: Lacking is a tough word, especially because I think the Boston ecosystem is so far ahead of most, especially for student entrepreneurs – perhaps just a better navigation system through ALL of the resources that exist within the Boston ecosystem. And I know several groups are actively working on this, including many Startup Island alums, and Greenhorn Connect!

GH: What’s the best/worst piece of advice you were given along the way?

SI: Best – Lead from a place of vulnerability. Worst – Give up.

GH: What was the best thing that happened to you last year?

SI: Getting to spend an entire month in Costa Rica running Startup Island trips, exploring the pacific coast, meeting new people, writing/reading a ton, doing yoga & meditation everyday, and getting inspired to build the future of this company. It was really a dream come true.

GH: What does the future hold for Startup Island?

SI: In the short-term, we have two trips coming up this summer. The Young Entrepreneurial Leaders Weekend which is closed for registration, and our second annual Startup Island Summer Camp , taking place in upstate NY August 25-27th. We also have our Startup Island Spring Break 2018 in Costa Rica to look forward to, and we’re excited to be joined by students from more universities than ever before.

Bigger-picture, we are slowly launching the “Custom Retreats” branch of our company, and have already begun planning entrepreneurship and wellness focused retreats for startups, student groups and other organizations. This is really exciting for us because it allows us take the environment we create for our travelers, and help others deepen connections within their own groups. We truly believe that more travel and more good vibes tremendously help the world become a better place, and we are just honored to play even a small part in that.

Learn More about Startup Island

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