The Journey Shapes You — An Interview with Josh Gershon, Co-Founder of Startup Island

Josh Gershon is the Co-Founder and Chief of Vision at Startup Island — a personal and professional development program that connects and inspires young entrepreneurial minds through travel experiences. He lives between New York, Boston, and Costa Rica and currently calls Boston home, as he spends most of the fall working with local university entrepreneurship programs and mentoring aspiring student founders. When he isn’t working… he’s working, but you can sometimes find him hiking, reading in a hammock, or at Miller’s Ale House on football Sundays watching the Giants. He still has hope that, despite their terrible start, they can turn this season around…

Be sure to follow Startup Island on Facebook, Twitter, and Instagram and go here to get more information and here to apply for their upcoming 2018 spring break trips to Costa Rica.

One more thing — check out their brand new promo video. It’s fire.

“Entrepreneurship is a state of mind.” Everything Josh Gerson has done with his life proves that those are not just words he told us. He believes them down to his core.

“I’ve always been an entrepreneur. I can say that now, but I didn’t always know what that meant. If you had asked me in high school, I wouldn’t have ever said I was an entrepreneur, even though I always loved the lemonade stands and selling baseball cards and all that stuff. I did all of it.”

Something else Josh believes down to his core? We are here to seek meaning in our work.

“One thing I learned about myself at an early age is that I don’t like doing work if there is no meaning behind it. If there is no meaning behind it, I can’t put in all of myself.

I was kind of a B+ person, going through life — good enough at school, good enough at sports, good enough in the social scene — I was always good enough. I always felt like I had this undercover potential, but unless there was something I was really enthused by, I never really surpassed that B+ level.”

The journey to find that best version of himself took Josh through 9 jobs and projects, 6 states, and 3 countries.

Seeing where he is now, the journey has been more than just a means to an end. It’s been everything.

Indiana

Josh started college at Indiana University in Bloomington in 2007. There he met the founder of BtownMenus, a food delivery service for Bloomington, and worked there at its very early stages. Starting as an intern, he became an essential piece of the company over his four years of college. The experience was invaluable.

“We were all guerrilla marketing. Everything was grassroots on the ground. We weren’t paying for ads like all the big players could. It was running around handing out T-shirts and cups and swag. Non-stop.

I realized in that moment that you don’t have to graduate to run a business that’s successful and to make an impact in your community. You can do that right now as a student.”

Coming to that conclusion proved to be essential in Josh’s eventual formation of Startup Island. “Looking back on that experience, part of why I think Startup Island found me as much as I found it, was that I saw how students can make a difference as entrepreneurs in school.”

Minnesota

Taking his knowledge from Bloomington, he and a friend moved to Minneapolis to launch a franchise of BtownMenus’ parent company at the University of Minnesota. Both were 21 years old. Despite their understanding of the company and their knowledge of the target market, they never experienced the growth they anticipated.

It turned out it was a lot harder starting the business without having the connections they did on their own campus, and near impossible without raising a large investment round. They stayed there are about 18 months before calling it quits.

“We chalked that one up as a learning experience.”

New York

Josh moved back to New York and quickly landed a job selling copy machines, working for the former President of a Xerox corporation.

“He was basically on a mission to take Xerox over, David vs. Goliath style. His idea was to build a salesforce of recent graduates to be the young gunners that go crazy and sell copy machines all over New York. It was classic, cut-throat sales environment; super boiler room; ‘coffee’s for closers.’”

After 5 months, he decided he couldn’t sell copy machines anymore and took another job, this time a managerial position for a company that waterproofed basements. That lasted 30 days.

“I made history. I was the shortest lived manager in the history of the company,” Josh said, laughing.

These two experiences shaped Josh’s thinking for his next career moves.

“This was what I now associated with the corporate world. I said, ‘The corporate world isn’t for me. I can’t do the rat race. I’m not a rat.’ I had an existential crisis.”

Georgia

Looking for a change of pace, Josh called his uncle who owned a series of retail shops in Tybee Island, Georgia, and put Josh to work managing one of his surf shops. He worked 80 hours a week but it was the time outside of work that proved most impactful.

“I was working like a dog, but I would come home and lay in my hammock. I would cook on my barbeque, listen to the ocean, and look at the stars. I would write and read and seek wisdom.

That was a very valuable experience for me. I had felt like I was lost. I was like looking for answers because, at the time, I was panicking. It was a great time to work very hard and reflect very hard.”

Colorado

The work in Georgia was very much seasonal, so Josh once again found himself looking for something new. He had stayed in touch with Mike Rolland, who ran BtownMenus. Mike invited Josh out to Denver where he had launched Mile High Menus, the company’s first time taking on a metropolitan city as opposed to a college campus.

Josh would work 20–30 hours per week, making good enough pay to get by and get a free place to live for his trouble. He was all-in and started the drive out to Colorado.

But while Josh was driving through Kansas, he learned that his original offer was only half as real as it seemed, and he couldn’t count on the hours or the pay he had planned on. If he wanted to stay in Denver permanently, he was going to have to find another “real job.”

“I couldn’t find a job I was excited about, and I found myself feeling totally alone and kind of defeated for the first time. It took me into this deep wave of, let’s call it depression. It was one of the darker times I’ve gone through. I never turned the lights on in my apartment. I would wake up, call in sick to work, sit in my apartment, not go to the gym, barely eat. I did that for 3 weeks. Finally, I said to myself, ‘Alright, what are we doing here?’”

Faced with a choice, Josh packed up his life again and moved back to New York. While the solo road trip out to Colorado felt triumphant, the solo ride home was anything but.

New York, Take 2

Josh went through the interview process with a few companies and was considering taking a commission-only sales job for another food tech company even though he had two salaried offers on the table.

This prompted “the closest I had ever been to getting in a fist-fight,” with his own father, who thought Josh was insane for wanting to take the hands-down least stable offer.

This led Josh to seek some calmness and escape to his best friend, Brian’s, childhood home; the place Josh refers to as “our safe haven as kids.”

Brian was living in Colorado himself at the time, but Josh had dinner with Brian’s dad’s girlfriend and her friend. They gave him some instrumental advice.

“I told them what happened and they asked, ‘Have you ever been to Israel?’ I told them I hadn’t and they said, ‘Go to Israel. Your perspective will change if you go to Israel.’”

Israel

Josh signed up for Birthright Israel and was lucky enough to get a spot a couple of weeks later. The experience did nothing short of change his life.

“I wanted to do something exciting and unfamiliar. I always had the sense that traveling and shaking things up, getting outside of your environment, is always going to be good for you. I was by myself, the first time I really traveled like that on my own. It was amazing for every reason, an amazing experience.

It totally grounded me, put things in perspective, and helped me figure out what I want in life. They have a very different perspective because they live in an environment that is always at war. The little things don’t matter to them. They know how to appreciate life.”

Back to NY

After the trip, Josh took a sales job with a digital printing company in NYC. It was his first job with a real base salary and even though he was making a good living, his mind was elsewhere.

He heard of a peer from college that had moved to Costa Rica and was blogging about it on his site, We Travel Tight. Josh became fascinated by travel blogging and digital nomadism.

“I’m sitting there at my desk like what the f*ck. And this guy is surfing with monkeys…

At that point, I told myself that I was going to save $10k and move to Costa Rica. I don’t know why; I don’t know what I’m going to do. But I’m smart. I’ll figure it out.”

Shortly after, in early 2013, Josh found himself in a serious relationship and his plans to move out of the country were placed on the back burner. He stayed at his job for a year before finding an opportunity to get back into the startup world with a new food tech company, Cater2.me.

Cater2.me

Josh started at Cater2.me during the early days and he still works for them today. The business provides large companies an outsourced catering solution so that someone at the company doesn’t need to spend countless hours ordering meals for hundreds of employees.

The company now employs over 200 people and operates in 11 cities, but Josh remembers the early days when he joined with just 12 people in their New York office.

“Back then, if I got an order for 10 people who wanted chicken nuggets, the whole office would celebrate. It was awesome. We were so young back then.”

Josh was once again bitten by the startup bug.

“Being at a startup from when it actually matters, when every little thing matters… seeing that was very cool, very valuable. It was great to be there for that. And I’m glad I got to see and contribute to that growth.”

“That’s when it happened.”

Josh was working at Cater2.me for 18 months and in that time had traveled to Costa Rica for two weeks with his girlfriend. The thought of moving there full-time stayed with him.

“The Costa Rica plan still never left my mind. I wanted to buy that one-way ticket and backpack across Costa Rica. I just knew there was something special about this place, something special would happen for me if I went there.”

At the same time, Josh was thinking of a career switch to graphic design and was exploring doing a 3-month immersive course with General Assembly. He thought that if he was going to spend his money anyway, he might as well get out of New York and take the course somewhere crazy, like Australia.

That was when his idea struck.

“I thought, ‘If I’m looking at General Assembly as my opportunity to grow professionally, and Costa Rica as my opportunity to grow as an individual, why can’t I create something that gives you personal growth through travel, and professional growth through an experience that surrounds you with coaches, mentors, and entrepreneurs — people doing really amazing things, that are going to serve as a resources, inspiration and lifelong connections?’

That was the idea. That’s when it happened.”

Startup Island

Josh had a false start with an initial co-founder of Startup Island before reigniting the idea with that same childhood best friend, Brian Helfman.

“The plan was to take people that are seeking meaning in their careers and lives, or have these entrepreneurial dreams and want to do something more, and to bring them on a retreat — have them travel together.

We started doing real market research, having conversations, hosting focus groups, talking to college students. One of the students we spoke to said, ‘I don’t know if I can just do this at any random point during the year, but if you make it during my spring break, I would consider it.’

We thought, ‘Why don’t we start off as an alternative spring break in Costa Rica?’ You have to imagine that not every kid wants to go party on the beach. Why don’t we take them to the beach and do something completely different? That was in October 2015. We started cold-emailing every student organization that we could find contacts for.”

“A milestone in my life.”

“We were reaching out to everyone. The President of the Northeastern Entrepreneurs Club emailed me back. I’ll never forget this because it was a milestone in my life: October 19, 2015, he emailed me back and said, something to the effect of, ‘Hey, Josh. Love what you’re doing. Sounds cool and would love to talk on the phone.’”

They talked on the phone the next day.

“A few weeks later, the first sign-up from Northeastern came in. A couple days later, three more. A couple days later, eight more. Next thing we know, we had 16 students.”

The seriousness of what they were now facing was not lost on Josh.

“We’re taking 16 students to Costa Rica. A) What the f*ck do we do?! And B) How can we make this the best week of their lives?!”

Building a curriculum, a trip, and a company

The two of them built a curriculum in the spirit of an entrepreneurial boot camp. They reached out to their contacts and found coaches to lead workshops, both in person and virtually. They led workshops themselves and even encouraged some of the successful student entrepreneurs to do the same. They quickly pulled an incredible experience together.

“We learned a ton from that first program and it went over very, very well… I remember on the flight home we said, ‘We’ve got something here. Let’s do it. Sixteen students was cool; let’s do 100. Let’s get 100 students on a trip this summer!’”

That grand plan turned out to be less than grand.

“That didn’t work. Instead of 100 students, we had eight.”

Instead of treating that next trip as a failure, they doubled down on using the trip to perfect the curriculum they had in place and they decided to make a change. They, in turn, realized that keeping the groups small in size allowed them to create bigger change for each participant.

“We went from being entrepreneurship first, personal development second, to realizing we are just as much community builders, connectors, and personal developers as we are entrepreneurial coaches.

It was a blessing that we wound up with such a small group, because we realized that the more curated the group and the more we could really get to know our travelers, the much larger impact we could make in their lives. Now we look to scale impact, not our number of travelers… and that’s so much more of what we’ve always been about.”

They followed that trip up with a young professionals weekend trip to upstate New York in August 2016. That trip did even more to shape the Startup Island approach.

“I was very nervous going into that trip. We had founders that were running companies for years and had raised money. Here I am providing an experience that is supposed to give them value when I could learn just as much from them. After that trip, we learned that Startup Island was a level playing field.

There was no hierarchy, whether you were a coach, a mentor, a founder of the company, or unemployed. Literally, it didn’t matter. We realized that what we did is create a safe space where people can really put it out there and honestly say, ‘I have no idea what I’m doing. How can you guys help me?’ It’s a place where you can be selfish in the best way possible. We want you to be selfish.”

Perfecting the model

Startup Island followed up that trip with two spring break trips to Costa Rica in 2017 and two more weekend retreats this past summer, both in upstate New York. Each new trip allows them to further perfect their curriculum and model.

“Now we are more personal development focused than just business development focused. Your business is an extension of you. The curriculum we now run at every Startup Island is called ‘The Business of Being Happy and Healthy.’ It was inspired by a TED Talk from Logan LaPlante.

We are all entrepreneurs because we are all the CEO of our own life. Whether you run a business or not, how do you run your life? Are you creating a plan for yourself that makes you happy and healthy?”

By honing their curriculum, Josh and Brian have found how to create the most impact for their travelers and now they plan to grow that experience. They plan to do four consecutive weeks of trips for spring break this year, accepting only 20–25 students each week.

Create your own path

Josh followed a long, winding path to make it to where he is today — one that was not carved out for him; one that he created himself.

“One thing we want to teach people is that if you think you’re at a fork in the road and you can only go two ways, you can carve your own path. There is not one, or two, or even 10 pre-determined ways to go. You can create a new path for yourself.

It’s messy, but it’s awesome. A lot of my story and where we now come out of always knowing what I wanted to do but not knowing how to do it… from being lost for several chapters.”

Looking back at the low points, Josh is humbled by them and glad for them to have occurred.

“They totally shape you — the hardest times. 100%. Thank God, they happened. Now, I am sitting here with a smile on my face, still with a long way to go, but grateful.”

We are incredibly thankful to Josh for sharing his story with us. Do us a favor and pass it on to your people. Everyone needs to know about Startup Island.