The act of starting a business is often arduous and lonely. Long days and nights hunched over a computer, bouncing ideas off yourself since there’s no one else around.


But it doesn’t have to be like that. Imagine being surrounded by like-minded entrepreneurs — and experienced coaches—soaking in a pool, staring at a volcano. Or savoring some alone time, taking the time to be mindful and reflect on your goals — and what you want to be when you grow up.


Sound like a dream? It’s not — it’s reality thanks to childhood friends Brian Helfman and Josh Gershon, the cofounders of Startup Island, who are determined to empower young entrepreneurs to be the CEOs of their own lives.

Rieva Lesonsky: What is Startup Island?

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Brian Helfman: Startup Island is a personal development accelerator designed to connect entrepreneurial-minded college students and young professionals through shared travel experiences. We host an alternative spring break program in Costa Rica for college students from all over the world. We also host summer camp weekends for “older” millennials (ages 23 - 39) in upstate New York and run a New Year’s trip, Ignite, for that same demographic, which is in a new location every year.


During our trips, participants have a chance to de-stress in an inspiring environment, develop meaningful connections with entrepreneurial-minded peers, and work with a team of experienced coaches. On all our trips, we try to maintain a 4:1 ratio of participants to coaches. Each coach leads a workshop within their realm of expertise and conducts one-on-one “Island Office Hours” with participants looking to dive deeper into their own goals.


Lesonsky: What was the impetus for launching Startup Island?


Helfman: Josh and I have been friends since we were 11. During the summer of 2015, I was two years into building another business when Josh approached me with the idea to do a retreat for entrepreneurs. He wanted to call it Startup Island. The more we talked about the idea, the more passionate I became about it. I realized Startup Island could be a perfect combination of the things I enjoyed, and the things I was really good at — creating meaningful experiences, travel, spending time in nature, mentorship, and building businesses. So in October, we decided to launch and began marketing our first trip — an alternative spring break program for college entrepreneurs. During that trip, in March 2016, I decided to shift my focus to Startup Island full time, to grow a business that could make massive positive impact.


Lesonsky: What’s the feedback from alums of the program?


Helfman: The feedback from our travelers has been really special. Some of the overarching themes include business breakthroughs, positive mindset shifts, and the development of a supportive community. There are traveler testimonials on our community page.


Lesonsky: One of your goals is to build a community. Have you accomplished that?


Helfman: One of the coolest things to witness as our business continues to grow is how much value our participants realize from the community itself. We always say, our participants arrive as strangers and leave as family — corny, but true. And the trip is just the beginning. Our travelers stay in touch through online forums we’ve built and organize their own in-person meetups around the world. We’ve seen everything from business partnerships to lifelong friendships form, even between people who originally went on different trips.


Lesonsky: You believe entrepreneurial thinking is not just for people starting a business.


Helfman: We believe having an entrepreneurial mindset is useful whether you’re starting a business or not. An entrepreneurial mindset helps you take ownership over your entire life. That said, we have seen many of our participants start businesses, especially those who were in corporate jobs when they first joined us.


They’ll start ramping up a side hustle after they get home from their Startup Island trip, and eventually they make that side hustle their full-time focus. Many of our alums credit us for helping build the confidence, network, knowledge, and resources to execute and build on their big ideas.


Lesonsky: What have you learned from creating Startup Island?


Helfman: I’m so grateful to be building this business for many reasons — the most significant is being surrounded by so many smart, ambitious, impact-driven people, who are equally as kind, funny, and genuine.


I’m also driven to learn more about the world’s problems, so I can do my best to help the members of our community solve those problems. Entrepreneurship is hard. Making an impact is hard. And doing it alone is even harder. Perhaps the biggest thing I’ve learned is a mutually supportive community of impact-driven people can help maximize the chances of success for each member of that community. I’ve seen it start to happen, and I’m so excited to see how each member continues to grow and change the world for the better.


Lesonsky: Looking back, would you have done anything differently?


Helfman: Yes, thousands of things. Mostly optimizations that could’ve made our trips even better, or things that could have saved us time. But I’ve learned from all of it, and I’m very happy with where the business is today.


About Rieva Lesonsky


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Rieva Lesonsky is CEO and Co-founder of GrowBiz Media, a custom content and media company focusing on small business and entrepreneurship, and the blog A nationally known speaker and authority on entrepreneurship, Rieva has been covering America’s entrepreneurs for more than 30 years. Before co-founding GrowBiz Media, Lesonsky was the long-time Editorial Director of Entrepreneur Magazine. Lesonsky has appeared on hundreds of radio shows and numerous local and national television programs, including the Today Show, Good Morning America, CNN, The Martha Stewart Show and Oprah.


Lesonsky regularly writes about small business for numerous websites and for corporations targeting entrepreneurs. Many organizations have recognized Lesonsky for her tireless devotion to helping entrepreneurs. She served on the Small Business Administration’s National Advisory Council for six years, was honored by the SBA as a Small Business Media Advocate and a Woman in Business Advocate, and received the prestigious Lou Campanelli award from SCORE. She is a long-time member of the Business Journalists Hall of Fame.


Web: or Twitter: @Rieva

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