"I just need a break."
How often to do you hear that statement? We seem to hear it, especially when the weekend is just around the corner or a holiday season is approaching.
We may even hear the need for a vacation right at the beginning of the new year when we have assigned ourselves too many goals, and you can already feel the burnout coming on. There’s just something about these times of year that can just push people to the limits -- or over their limit.
Now when most people hear words "break" or "vacation" they instinctively think of staying in bed and watching Netflix, or lying on the beach at an all-inclusive resort, or for the more adventurous (or financially endowed) backpacking through Europe. In other words a complete shutdown from work and in most cases mental exercise entirely.
But is that total shutdown really what you need to recover? Instead, you might just need to take breaks your day-to-day routines, focus on something more meaningful for yourself, or even just learn something completely new.
Personally, I find myself reinvigorated by an entirely new opportunity, adventure, or learning experience, in much the same way as though I've just returned from that year-long vacation I owe myself. In fact, I finally realized that I hate the idea of a total mental shutdown. I truly enjoy being productive and constantly challenging myself (one of the blessings of pursuing a path of fulfillment). I just know I need to be able to reinvent myself or shift my focus every-so-often.
Similarly, I’d imagine that many people are looking for something a pure vacation can’t always deliver. Josh Gershon the co-founder of Startup Island certainly knows a thing or two about that longing. Josh founded Startup Island in 2015 as a classic example of the entrepreneur scratching their own itch.
Josh describes his own career inflection point: "
I thought about signing up for a three-month General Assembly course.
That seemed like a decent option, but I wasn’t totally sold on learning graphic design as my “big move.” At the same time, I was seriously thinking about taking some time to just travel and see what happened. It’s always been my dream to pack a bag, book a one-way ticket, and let life take me on a journey. When thinking about these two options, it suddenly dawned on me that I could possibly combine them."
In reality that need for a break isn’t necessarily just fatigue or burnout. In reality, a break isn’t enough to remove your tiredness. It’s just temporary. It’s a solution you’ll need to repeat over and over and eventually that might not be enough.
Josh hit the nail on the head when discussing going on a journey or just traveling and seeing what happens, in other words, an adventure. But a vacation is often just an adventure that fades. The real magic is in discovering an adventure that lasts. It’s in making everyday part of a greater adventure.
Josh saw that same need and it’s part of what sparked his decision to create Startup Island:
“…Finally one night in bed, the light bulb went off. Rather than take a program that had only some of the components I was looking for, I would set out to create one that had everything I was looking for. A travel experience meets a professional development experience, which thus creates a very valuable LIFE experience. One where you get to meet new people, connect on a deeper level, perhaps gain some spiritual enlightenment – and this, this would give me the inspiration and the tangible skills necessary to figure out what I wanted to do next, and how to do it.”
In Josh’s own words Startup Island is "a community, built to connect young entrepreneurs all over the world, through shared travel experience.”
The vacations that truly revitalize you are the one’s that fundamentally change your perspective or approach. It’s the reason Tim Ferriss’s Startup Vacation was so strongly received. It wasn’t a total release of all work, but rather a reframe of his priorities and focus. Among his key priorities at the start of the year is planning his vacations, otherwise "work will take all the time."
While Ferriss will be the first to admit he needs to completely detach from his usual grind on these breaks, his vacations are also giant experiments. They are highly focused on specific projects, learning, or skills but simultaneously manage to cut away all the noise of everyday life. Usually, he comes away with a lifelong skill or new passion that creates a far richer and longer lasting experience.
Startup Island -- the perfect “productive vacation.”
Startup Island captures this same ethos on their group trips which bring together unique groups of people, to develop new relationships, build new skills, and alter their perspective. The idea is not a one-week or one-month change in behavior, but it is more like an adrenaline shot to jumpstart a much longer lasting shift in lifestyle and process. This jumpstart is just the beginning for the founders of Startup Island, but some of the early outcomes Josh discusses are a big step forward:
"For instance a CPA who was on our trip, helping a first-time founder get his numbers in order before going out to pitch investors. He recently went on to raise his desired amount, by the way.”
In my mind, no single experience is as powerful as habit-formed evolution over time. However, Startup Island is an exceptional launching pad that facilitates changing your day-to-day experience.
I had the pleasure of connecting with Josh back in his Cater2.Me days and when he shared his latest ventures, I was thrilled to have the chance to chat about his work more in-depth. Check out our full excerpt below where we chat about his journey of ups and downs with Startup Island, skills development, the lionization of entrepreneurs and much more.
SG: What inspired you to launch Startup Island?
JG: From a young age, I guess I was pretty entrepreneurially minded. I used to shovel snow and rake leaves for neighbors, set up car washes & lemonade stands on my block, burn CD’s for people in school, etc. The process of taking action to earn money was exciting. If I was told to do something, even if money was a reward, I wouldn’t follow through. If I came up with the idea to do it myself, I was always incredibly enthusiastic about it.
I went to college at Indiana University where I began working for an online food-ordering platform called Btownmenus.com. The founder of the company and a fellow student, Michael Rolland, became a good friend and early mentor. He was an example that entrepreneurship is the best way to create the lifestyle you want, rather than taking the conventional path and hoping it provides the life you want.
Post-college I wasn’t inclined to pursue a "typical career" path and headed off to launch my own business. A year and a half later I extracted myself from the situation, needless to say, "it didn’t work out quite as planned.'
I wound up in NY where I got my first sales job selling copy machines. Best sales training I could have ever asked for - classic Boiler Room, Glengarry Glen Ross-type stuff. But I certainly did not want to wear a suit every day, get in my car and drive all over Long Island, scoping out which Dr’s offices copy machines were outdated.
After bouncing around a bit for that year I ended up moving to a small beach town outside of Savannah, Georgia, where I managed a surf shop and pioneered their social media campaign. I worked 80 hours a week, from 8am-11pm most days, but absolutely loved being on my own.
Having made this decision because I wanted too, and not because I felt like I had to, brought me peace of mind. I was paying only $500 a month, living across the street from the beach, where I had a patio with a grill and a hammock, and though I was always working – in my spare time I would lay out there listening to music, reading, writing and having deep phone conversations about business and life, with people from back home that I missed.
The first startup job that I landed was in NY at Cater2Me, a food-tech company that provides meal services for offices. Started by two first-time founders out of Wharton, and with a team of awesome and excited individuals around them, I knew this was the next step in my career.
Over the next 18 months, I witnessed the growth of the company from just around 40 employees in 6 cities, to over 100 in 14 different cities. This experience was invaluable for my own growth and really highlighted the fact that startup life puts you on the fast track to professional development.
Okay, so here’s how it all ties back to Startup Island.
About a year and a half in, I was getting a little restless, and thought about potentially switching out of sales and into something creative, like graphic design. I had no formal training but always played around on Photoshop and enjoyed it. I thought about signing up for a three-month General Assembly course, which would take me from amateur to slightly better than that and may have been able to get me an entry level job with a different startup, once I completed the program.
That seemed like a decent option, but I wasn’t totally sold on learning graphic design as my “big move.” At the same time, I was seriously thinking about taking some time to just travel and see what happens. It’s always been my dream to pack a bag, book a one-way ticket, and let life take me on a journey.
When thinking about these two options, it suddenly dawned on me that I could possibly combine them. General Assembly, for example, had campuses all over the world. I could have gone and taken a graphic design course in Melbourne or Sydney, let alone same old New York City.
I looked into it some more ideas and continued to weigh out my options, when finally one night in bed, the light bulb went off. Rather than take a program that had only some of the components I was looking for, I would set out to create one that had everything I was looking for.
A travel experience meets a professional development experience.
When that happens, you have created a very valuable LIFE experience. One where you get to meet new people, connect on a deeper level, perhaps gain some spiritual enlightenment – and this, this would give me the inspiration and the tangible skills necessary to figure out what I wanted to do next, and how to do it. This was what I needed so much, and this is where my inspiration for Startup Island came from.
SG: What is your vision for SI going forward? What does the company look like in 5 years?
JG: After our first few trips, and an upcoming four weeks of alternative spring break for college entrepreneurs, I am confident in our vision moving forward – which is to build a community connecting young entrepreneurs all over the world, via shared travel experiences.
This means more consistent trips, across different cities and countries, and for a wider audience. We experimented with a trip for young professionals (Post Grads – Mid Thirties) this past summer, and it was mind-blowing, both for our attendees and for us. We have now seen how inspiring the Startup Island experience can be for all entrepreneurs, not only college students.
With that, we see more and more trips happening, the community continuing to grow, and our team continuing to grow with it. My vision for five years, or even sooner, is to get to the point – where somewhere in the world, there is always a Startup Island trip going on.
SG: Biggest challenge getting SI off the ground?
JG: There have been a few big challenges so far, which we have definitely learned from. An early challenge was figuring out our identity. Were we a travel program, an accelerator program, a personal development program?
Selling our trips was difficult at first because it was hard for us to say exactly what we were, and exactly what you would get by joining us. Simply put today - we are a community, built to connect young entrepreneurs all over the world, through shared travel experience.
Another challenge thus far has been pricing. We’ve been working primarily with college students, and though our trips are priced very competitively, if not lower, than other college programs, students can’t always afford to spend a thousand dollars or more on a one-week getaway. So we’ve created a crowdfunding campaign in order to help students go out and share the experience with friends and family, alumni, local sponsors, etc., to try and subsidize some of the costs.
SG: How do you see yourself as different from competitors? Other enrichment programs, camps, skills/development oriented retreats, etc.?
JG: I have never seen a community grow as strong as ours, in such a short amount of time. Never before in my life have I seen groups of strangers leave after just a few days together as brothers and sisters. People saying, “I love you” to each other as if they were family.
People continuing to get together and make plans to see each other, long after their trip. People willing to go so far and beyond out of they’re way to help a fellow Startup Islander with something. People who were NOT even on the same trip, but have connected through our Facebook alumni community, now talking to each other on weekly calls.
Not to sound all kumbaya, but our community really is built on love, energy, and an amazing entrepreneurial spirit from our travelers. That’s stuff that you can’t manufacture. We’re incredibly lucky to build off of that.
SG: What has been the most rewarding moment for you thus far?
JG: Oh man tough question – I’ve been moved to tears several times during each of our trips. Each group is just so incredibly inspiring, and watching these meaningful connections form, even forming them myself, has been the ultimate reward.
One of the coolest moments for me, though, was during our first trip. It was the first time we’d ever done this obviously, and we were just so happy to see our baby, this thing that was just a raw idea only a few months before, actually happening. I remember we looked at each other, and we were just like, “we did this.”
SG: What is the biggest thing we can do to facilitate entrepreneurship?
JG: I immediately think of two things.
The first: is to form Deeper Connections as a Society. Entrepreneurship is a mindset. It’s so natural and innate for each human to want a real sense of connection and meaning in their life. I believe that travel helps us learn things about ourselves and helps us develop a deeper sense of connection to the universe, and how we see ourselves in it.
Travel isn’t necessarily the only way to form a connection, but it will certainly open your mind, and that openness is essential. When you connect with people on a deeper level, whether through travel or not, it creates a type of energy that is very similar to entrepreneurial energy.
It’s a stimulant. It feels good. It makes you want to keep surrounding yourself with more positivity and creativity. It’s the kind of energy that makes you want to just keep going. We need to help young people form these connections, join these communities, and build them themselves.
The second: is to encourage out-of-the-box thinking / Stop Nay-Saying. There is no longer only one way to do things. And there is no time for, “that can’t be done.” If you believe in something enough, you should try it. No matter how weird or out there it seems, or if no one else is doing it, or if it’s not taught in your textbook, it doesn’t matter.
We need more people, especially in the education system, encouraging folks to try and create the stuff that they think would be awesome. If it doesn’t work, they’ll learn from it, which is a victory in itself. It makes me sad to hear from people who don’t pursue their ideas because other people haven’t given them the mental support and encouragement to take the next step. Good thing the guys behind UBER didn’t stop when people told them they’d never replace cabs.
SG: I’d love to get your perspective on the deification of entrepreneurs and entrepreneurship?
JG: Entrepreneurs are changing the world, and entrepreneurship is here to stay. This isn’t just some fad or bubble that’s going to burst. Entrepreneurship is the vehicle for passionate people all over the world, to take action and solve meaningful problems in their own way. That said, the idea of entrepreneurship has become very sexy and cool these days.
It’s interesting because, to me, the hardship of entrepreneurship is the part that’s exhilarating. The constant struggle of it all, the rolling a boulder up a hill FOR A LIVING, is what appeals to me because I care so much about what I’m building that I couldn’t imagine doing anything else.
I think a lot of people see entrepreneurship as huge fundraising rounds, large exits, and billion dollar valuations, which are obviously sexy but are mostly a façade. I’d like for us as entrepreneurs to start showcasing the extreme ups and downs, and the uncertainty more - because fighting through that is what it’s really all about. That’s why I’m so pumped about projects like Generation Startup.
SG: Number one piece of advice for the college entrepreneur?
JG: Use college to the fullest! Take classes that actually interest you, and really try to learn. This is the one time in your life that is literally dedicated to learning. Try to plan your learning around your interests and soak it all up, inside and outside of the classroom.
Build relationships. Introduce yourself to the people you sit next to in class. Step out of your comfort zone and immediate group of friends. There are so many interesting people around you - use every chance you get a chance to meet someone who can teach you something, make you laugh or inspire you. Look to do that for other people as well. Also, who knows, you may meet your co-founder.
I’ll add one more piece of piece of advice. Do NOT do stuff you don’t enjoy. Again, college is your time to learn (about yourself). Make an effort to do things that stimulate your personal growth and creativity. If something isn’t for you, there is no shame in saying “no.”
SG: Skill you are focused on developing, Personal or Professional
JG: A stronger meditation practice, and my life-coaching certificate.