I am often asked, “What do you look for in an entrepreneur?”


I believe there are all types of successful entrepreneurs. There are visionaries that lay out bold initiatives and then delegate the day-to-day operations to others. There are technical, product first entrepreneurs that deeply understand the customer but do not have a clue how to organize, scale or lead teams. There are sales leaders that can tell a great story and convince early customers to take a chance on a new product, but are not detail oriented. There are operational leaders that focus on building great teams. But all of these differing backgrounds aside, to be effective, an entrepreneur must be intellectually honest with themselves about their own strengths and weaknesses and that of their team. In short, they must be self-aware.

What do I mean by self-aware? Many people talk about self-awareness as being able to look at yourself in the mirror. Being able to see your values and behaviors objectively. But this is not enough. It is not enough to see yourself through your own eyes, you must be able to accurately see yourself through other’s eyes. Tasha Eurich in her book Insight, describes a better metaphor. Rather than a mirror, think of self-awareness as a prism. The white light going into the prism might be your intention, but when that light goes through the prism it is bent and creates an array of colors. These colors are the very real and different perspectives of others. According to Tasha, self-awareness is “the ability to see ourselves clearly - to understand who we are, how others see us, and how we fit into the world”.

In this crazy world of hyper-scaling startups this is even more important as different skills are needed at each stage of growth. As one of my portfolio company CEO’s told me, “If my company is tripling each year, I need to triple each year.” The point is, if an entrepreneur is not aware of how their skills match what is needed for a given stage of growth, they will simply not grow fast enough. If they hold tightly on what has worked for them in the past, they will not be capable of leading at the next level. And, if they aren’t scaling fast, a self-aware entrepreneur will recognize that a new leader may be needed to move the company and the team forward.

Some of you reading this will say, “Yes, but there are many examples of highly successful entrepreneurs that do not resemble the definition of being self-aware by any stretch of the imagination”. You may believe that it takes a certain level of narcissism to found a company capable of changing the world. Maybe, but I believe these individuals are the exception, not the rule. I believe that the next generation of tech workers are beginning to reject these types of leaders, making it more difficult for them to recruit top talent and ultimately win. I believe teams are looking for effective leadership.

In her book, Tasha points out several ways to build greater self awareness. One way is to actively seek, receive, reflect and respond to feedback. It was this advice from the author that led me to commit to a 12-month development program kicking off with an in depth 360 feedback process. The process will gather feedback about me from my team at MATH, portfolio companies, fellow Board members, friends and family. I am deeply curious to know what they think about how I can be more effective. And, while I am sure there will be bits and pieces that make me uncomfortable and will stretch me, that is the entire point, to see things from their eyes.

So, my challenge to you is, what will you do to learn a new insight about yourself?