Entrepreneurship is about more than owning a business.

It's about owning all aspects of your life.

Our Story:

In October of 2015, we launched the first Startup Island trip as an Alternative Spring Break for College Entrepreneurs. Through our own startup experience prior to that, we knew that pursuing an entrepreneurial lifestyle could be lonely and isolating -- like it's you against the world. But we also felt and witnessed the sighs of relief that came from connecting with others who were trudging a similar path. We created Startup Island as a way to catalyze more meaningful connections between young entrepreneurs, in the most effective way we knew how -- during an immersive, shared travel experience.


This business, like anything else, has evolved over time. We've welcomed hundreds of young entrepreneurs onto our trips, and into our community, and we've also welcomed many people who aren't entrepreneurs. At least not in the traditional sense of the word. We've realized that this thirst for purpose and connection is prevalent across all walks of life, and we had created a program that provided just that.


Through our programs, we help you develop the self-awareness, confidence, global perspective, empathy, risk-tolerance, and support system to design your ideal life. We get you out of your daily routine and into a safe space to share, reflect, and develop bonds with people who get you amped up about life and the opportunities ahead. After your first trip is over, these people will be there to support you whenever you need them.

Meet the team:

Josh Gershon | Co-Founder | Chief Storyteller

Startup Island is a product of my own self discovery.


While at a crossroads in my career, I asked myself a very big, but very common question amongst young twenty-somethings..."what am I going to do with my life??"


My soul was telling me to travel so I could experience the world, it's beauty and learn my place in all of it; but my brain (and family, friends, society) was telling me to buckle down, network and explore sustainable career options.

Feeling forced to choose between my personal and professional growth, the idea for Startup Island was born.

Brian Helfman | Co-Founder | Chief Experience Officer

Growing up, my passions were constantly evolving, and it was hard to choose one path to pursue. In my short career, I've held down lucrative corporate jobs, been a ski bum in Colorado, launched my own business, gotten involved with non-profits solving global problems, and traveled extensively.


Along the way, I started to learn what inspires me most -- being surrounded by good people, adding value to those in need, and creating memorable experiences for myself and others.


So when Josh, one of my best friends since childhood, came to me with the idea for Startup Island, it felt like everything was coming together. We're all on a constant journey of self-discovery, and I'm so grateful for the opportunity to help others on their unique path.

Shivank Taksali | Head of Community

I was in the frenzy of my college career -- trying to grow myself professionally and personally, and in desperate need to escape Boston’s brutal winter. Spring break was right around the corner and I had to decide how to spend it.


I could choose to stay at a hotel with my friends in Miami or Cancun, and party by the beach for the whole week. Or I could try something different that would contribute to my growth and self-improvement.


Three years and five trips later, here we are, and I am thrilled I made the choice I did. 


I believe deeply in the mission of Startup Island, as I've experienced its power so many times myself. Now I can help thousands more like me, experience it for themselves.

Sam Stokes | Marketing Manager

Sophomore year of college I received an email that would unknowingly change my life: the one that put Startup Island on my radar. 


I went into my first Startup Island trip knowing no one and left with a family that I connected with on a level I’ve never experienced. I didn’t know  exactly what to expect, but it far exceeded all expectations I had. So much so, that I’ve been back for 4 more trips!

SI has served as catalyst for much of my growth and fulfillment, both personally and professionally. It’s helped me awaken the power I have within me and gave me the courage to carve my own path in life.


Now, I’m grateful I can help get SI on the radar of others so that they can experience the magic and transformation that comes from it!

Alex Grant | Programming Coordinator

I have long lived by the phrase, “you must get lost in order to find yourself” – a mantra that forces me out of my comfort zone and into the unknown.


In July 2016, I was introduced to Josh who over the phone convinced me to take a chance on Startup Island. I traveled to Costa Rica on the second ever Startup Island trip which set me on a path of what I have grown to call “professional development, by personal means.”Since my first trip, I have been hooked.


Every interaction with the Startup Island community reminds me that we’re all traveling on our unique paths, but with a little help from a community that cares, we can lower the barriers to starting up, and help each other take meaningful steps forward in our lives and careers.

Our amazing 2019-2020 fellows.

Kelly Landis

Operations Team

Declan McCarthy

Custom Experience Team

Conner Krollman

Student Experience Team

Brian Ardavin

Student Experience Team

Amanda Monachelli

Community Team

Tori Popescu

Marketing Team

Nico Repollè

Content Team

Anthony D'Apolito

Content Team

And our wonderful advisors.

Ben Bechar

Social Engineer

Founder & CEO, Maslow

Cathlin Carlson

Former VP of Programs

Venture for America

John Lynn

Founder, The Studio Project

Mentor at Founder Institute

Sally Nilsson

IPEC Certified Life Coach

Equine Program Facilitator