I’ve always had an entrepreneurial spirit. When I was about 13 or 14, I partnered with a friend to make specialty chocolates that we sold at school. We were successful until the partnership dissolved over an argument on how to use our profits. It was better than going belly up, and I learned my first valuable lesson about communication.
I wasn’t always steering the ship though. Right out of college I worked as a technical analyst for a massive DC-based consulting firm. I began working in their New Jersey office which was beige with beige cubicles.
From 9am until 7pm, every day, I worked in a windowless office attached to a windowless server room at the end of the hall. Within a very short period of time, I was promoted twice and my salary nearly doubled, but the job offered very little meaning.
I thought, is this what it means to have a career? Spending 70-80 hours a week around people who don’t really want to be here? Am I doomed to spend my life in front of this computer in this cubicle?
All my energy was going towards something where I felt no sense of service or contribution. I learned that fulfillment from work is paramount, so I walked out the door and onto the entrepreneurial path.
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I went on to found AdClip networks (later relaunched as Endai Worldwide). It was the turn of the millenium, a great time to be developing new technology in the online marketing space. I followed that success by founding Kite Adventures, leading a more adventurous lifestyle by offering guided kiteboarding tours in Brazil. The Endai end-game was purely financial success, and kiteboarding fulfilled a deep desire for adventure. But I still wasn’t lining up with my greater purpose, my ‘why’, with a company that could fill it.
Around this time, I reflected on my first hollow work experience back in cubicle-land. I remembered all the good people who were keeping busy doing work that depleted their spirits and only provided financial reward. I wanted to help others achieve their purpose and through that desire I discovered my own. I wanted everyone in the world to have the opportunity to discover and find their ‘why,’ to start or join an organization based on that ‘why,’ and to experience a profound meaning and satisfaction in their work. I wanted to start a company that would change the world in positive, meaningful ways.
And that is when I was introduced to the concept of the 15/5 report by Brad Oberwager, CEO of Sundia. Brad showed me software that he had developed that would soon change my life. The application was based on a practice made famous by Patagonia CEO, Yvon Chouinard.
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Chouinard lived an adventurous lifestyle and implemented 15/5 reports to keep up with the most important things going on at his company. He asked all of his employees to spend 15 minutes each week writing about their successes and challenges, and reviewed the responses in about 5 minutes.
I decided to take this idea to the next level, allowing key information to be automatically rolled up to the highest levels of an organization via weekly reports. The reports were turned into conversations and my larger vision was for 15Five to become the communication backbone for thousands of companies, where employees could be supported in doing their best and most creative work. But first I had to get the word out…
In January of 2012, someone forwarded me an email from Jason Calacanis. Jason wrote about some of the key things he looks for in a company he wants to back and how for every problem there was one company that he remembers and refers.
For filesharing, it was Dropbox. For communication, it was Yammer. I said to the team, “I am going to get this guy to recommend 15Five instead of Yammer”. Although I had no idea idea how that was going to happen.
Two weeks later I received another email from an investor regarding Jason’s Launch Festival, an annual event where startups could show the world how they were going to change it. Registration had already been closed, but the investor said that he was looking for a couple more applications and encouraged me to reach out. I had a successful interview with Jason’s assistant and was invited to Sequoia Capital to pitch him in person. I arrived and introduced myself and he said, “I love your product.”
Things went well on the Launch stage, David Sacks of Yammer showed interest and eventually became an investor. Six months after I said that I was going to get Jason to recommend us, he wrote an article entitled Good To Great To Excellent: A Roadmap. In it he wrote, “You should try [15Five], the truth shall set you free”.
Around the same time, Inc. published a piece entitled Must Have: 15Five, Best Way To Keep Track of Employees. Now I had the endorsement of successful entrepreneurs and press that propelled us off to a big start. The articles and blogs kept being published and more entrepreneurs were spontaneously supporting us. Suddenly hundreds of companies wanted to create a regular feedback loop between employees, managers, and executives.
All of these companies wanted a stronger corporate culture, and better employee performance. They realized that streamlining communication and providing a lightweight feedback channel would not only help with the flow of communication but also shift the culture to be more open, transparent and authentic.
In just over 2 years we have over 50,000 people in over 140 countries responding to regular questions from leaders. While I excitedly watch the numbers climb week over week, I am still driven primarily by my ‘why.’
The mission remains to create a world where we all work in organizations that are fully actualized, that create extraordinary value for their employees and customers, and where we get to work alongside a vibrant group of colleagues who are committed to creating and living a great life.