From the Suit to the Wetsuit

24 Oct 2016 | Blog, Interviews

On the surface, my career path seems chaotic. I’ve started a hip-hop record label, run a youth development nonprofit, worked in socially responsible investing and founded technology companies in green business, online education and crowdfunding. These ventures appear very different but are unified by a common thread: aligning my personal values with my professional pursuits. As a social entrepreneur (generating profit while promoting social and environmental values), I look for opportunities to make the world better while building great businesses with inspiring people. That’s how I found Outsite.

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From the Big City to the Beach

I moved to New York City one week after 9/11. The air was literally still steaming with dust from Ground Zero. People were shocked and afraid but also resolute and motivated. Demonstrating the trademark strength of New Yorkers, the city was busy rebuilding and I wanted to join this resilient community. It was also a definitive startup opportunity for all of us.

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The Pain Point

New York City gives a lot but takes a lot as well. I eventually became the stereotypical New Yorker, driven but disconnected. In the process of accumulating advanced degrees and running multiple businesses, I was also running myself into the ground. New York is one of the world’s food capitals, but I was regularly eating dinner at fast food places that stayed open late. It has a beautiful mix of mountains, lakes, and ocean, but I rarely took a day off on the weekend to experience the natural attractions. Almost 10 million people live in the city – a large, eclectic and diverse group – but I wasn’t investing enough time into personal relationships outside of work. I sensed a void, a deep need to prioritize my physical, social and emotional health so I could succeed in all dimensions of life.

The Pivot

As a tech entrepreneur, I had visited California many times, but mostly San Francisco, which felt too similar to other big cities. When I decided to try a different lifestyle and leave New York City, I could have moved anywhere in the world. I asked myself two questions to help me find the right place:

  • What is a growing innovative economy that I haven’t yet explored?
  • Where can I live on the beach and learn to surf?

San Diego was the clear answer. The city is small enough to be intimate, but big enough to have an impact.

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Combining Work and Play

I moved to San Diego with a blank slate. As Ray Bradbury said, “Jump off cliffs and build your wings on the way down.” One lesson I’ve learned throughout my career is if you surround yourself with good people and treat them well, doors will open. Soon enough, I was introduced to the founder of Outsite, Emmanuel Guisset, through a mutual entrepreneurial friend. Emmanuel’s authenticity and vision as a founder highly impressed me and compelled me to invest in Outsite.

I was also attracted by Outsite’s mission to create a like-minded community of adventurous, interesting and ambitious professionals from all over the world. In an increasingly virtual era, Outsite is building a physical social network, bringing people together to enjoy nature, share ideas and have fun.

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Investing in the Future of Remote Work

Outsite represents a sea of change in the way people work and live. Location independence is a new lifestyle as more people untether from their work office and home lease or mortgage. The values of flexibility, sustainability and community are transcending traditional ideals of privacy, consumption and individualism. As this transformation takes place, the divide between work and life is blurring. Previously viewed as an inherent contradiction, work-life harmony has now become a virtue – and reality. I am a testament to this fact. I love my work and live in a beautiful place with amazing people. Not to mention, I finally learned how to surf.

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