Kass and I are often asked what makes a successful entrepreneur. To answer this, I'd like to share the story of Douglas Delreza, one of the most impressive people Kass and I have ever met. 

Douglas stepped off the plane in Miami, Florida from La Paz, Bolivia, on September 14, 2004, with a 6-month tourist Visa, a small suitcase with all his belongings, $500 in his pocket, and a grand vision of building a better life for himself and his family. 

A week after arriving in the US, Douglas made his way from Florida to Maryland to live with his mother Elda, a wonderfully warm woman who worked as a babysitter when Kass and I were building Golf.com. When Elda introduced us to Douglas, we immediately knew he was special. Despite only speaking broken English, his laugh was contagious, and he told us confidently how excited he was to find a job as a professional chef in the United States.

A week later, Douglas shared the good news that he had landed a job at the top catering company in the area, Ridgewells. At first, the company informed him they did not have a spot for him.  But Douglas offered to work for free to show them his skills. The following Sunday, he was manning the pasta station at FedEx Field in Redskins Owner Dan Snyder’s suite.

We’ve watched his success continue over the following 18+ years. He started his own company, became a manager at a well-known food chain, and became an executive chef at an upscale catering company.  Now, he lives in Roanoke, VA, with his wife and 6 kids, where he is a Director of Commercial Support at US Foods, a $30 billion food service company. 

None of Douglas’ success is a surprise to Kass and me. He lived with optimism and never let fear hold him back.  He knew his strengths and hustled. He bet on himself and was extremely grateful. He knew what he wanted out of life and how to get it, and it has been inspiring to watch him achieve great personal and professional success.   

In the past 25 years working together, Kass and I have employed hundreds of people directly through our various companies. We have also invested in close to 100 fellow founders who have employed tens of thousands more. Through it all, one simple truth has shined through: success like Douglas’ is driven just as much by HOW someone operates than by specific skill sets or motivations.

Nonetheless, very little time and effort is spent individually or in organizations to examine how we go about doing what we do. Kass and I believe an investment into building a framework for how you want to approach life’s chaos will pay off handsomely. This post is our first public effort to start the conversation.

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What is the how?

The how is the set of values and principles that form the foundation of how each of us orients ourselves to and interacts with the world. It is the substrate on which we build our lives, the moral code compiled over life’s interactions comprising what Kass and I now call our life operating system or LifeOS. 

The how is not tied to a specific job or task. The how is not dependent on who you are, who you are with, the situation you find yourself in, or what you are doing. The how is not about building a belief system. It is a behavioral system.

The LifeOS is as important to who we are as humans as the computer operating system is to the computer I am using to write this piece.

The current self-help complex

Our collective fears, insecurities, aspirations, and dreams have spawned an industrial self-help complex that promises to help us figure out what to do and why we do it. Very little exists to help us build a resilient operating system that runs smoothly, seldom crashes, and helps us make life easier, more enjoyable, and more successful, however you choose to define that.

Amazon’s all-time best-selling personal success books reflect this. Atop the list is Atomic Habits: An Easy & Proven Way to Build Good Habits & Break Bad Ones, followed by Breaking the Habit of Being Yourself (#8) and the perennial favorite, Stephen Covey’s The 7 Habits of Highly Effective People (#14).

“Before you talk about WHAT you do,” says Simon Sinek, author of the Start With Why TED talk, book and on-demand classes, “you need to know WHY you’re doing it.” This is the “compelling higher purpose that inspires us and acts as the source of all we do,” Simon writes.

The 60 million views on his TED Talk, 5 best-selling books and a company dedicated to helping people and organizations find their purpose has helped Simon both cement his idea that the why is where to start.

To be sure, Kass and I are big believers in the power of why. But we believe it is ineffective without the What. “The real joy in life comes from finding your true purpose and aligning it with what you do every single day,” Tony Robbins tells adorning fans on Twitter.

As we think about friends and colleagues who “made it” and others who have struggled again and again, we come back to how they operate more than what they do and why they do what they do. Working with some people feels frictionless, fun, easy and sometimes even joyful. Working with others feels tedious, frustrating, and draining. This is not just because of what they did but how they operated and how they make others feel.

As we transitioned from starting our own companies to investing in close to 100 others, the differences between the “hows” and “how nots” came into focus. We started to notice the difference between how successful entrepreneurs and employees and others operate. 

As Kass and I look back at our two-plus decades together, we only now realize that our shared purpose and vision (the why) and action plan (the what) were insufficient for us to build the life we wanted. 

The dreams we started out with came true over the past two decades not just because of our purpose or what we decided to focus on, but because of how we act. This how – how we treat people, how we work, how we play, how we prioritize, and how we approach the chaos of this so-called life – is what we are now calling our life operating system, or LifeOS. 

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The LifeOS is independent of background and circumstance. It works for us just the same way it worked for Douglas Delareza after stepping off the plane from Bolivia. 

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