Everett Harper is the CEO and co-founder of Truss. As a rare combination of a Black entrepreneur with a Silicon Valley pedigree, he boasts a proven record for solving complex problems with social impact. With the foresight to build a remote-first company in 2011 and implement salary transparency in 2017, Everett anticipated the importance of hybrid work and DEI by a decade. Everett also just released his first book, Move to the Edge, Declare It Center: a powerful and pragmatic take on solving complex problems and making decisions during times of uncertainty.
Tell us about your childhood and where you grew up?
I grew up in the Hudson Valley of New York, in a small town called Wappingers Falls. My parents were born and raised in the Homewood neighborhood of Pittsburgh, Pennsylvania. I’m the first person to go to college in my family, but my parents were pioneers in their own right. My mother, Jacqueline Harper, was one of the first Black women programmers at IBM in the early 70s – a “Hidden Figure” in the technical corporate world. During my childhood, we had to overcome the challenges of being one of the few Black families in our town. Personally, I had to navigate both the overt racism of being called the N-word by neighbors as a child to being excluded from social events as a teen. However, my parents’ gift to our family was that we never heard the phrase, “If you go to college”. Instead, it was always, “When you go to college”. That important shift set a standard that supported my academic curiosity and drives for being a high achiever. It also manifested in soccer, which enabled me to play internationally in Scotland and Germany as a teenager, and set the stage for winning an NCAA Championship in soccer at Duke in 1986.
How did you get started as an entrepreneur?
I have the common formative childhood sales story, learning to sell door-to-door everything from candy to light bulbs – the best seller by far. (Lesson: make it easy for people to buy what they actually need). My first adult entrepreneurial experience was building an organizational development training company focused on diversity, equity, and inclusion in Durham, North Carolina in the mid-1990s. I built teams to work with banks, hospitals, and corporations, and notably to help merge previously segregated Durham City and county school systems. My first technology company was Macerate Ventures in 2009, where we helped build a wine app called Bottlenotes, which was a Webby Award winner.
What is one business lesson you would tell a startup founder?
Get comfortable with being uncomfortable. It speaks directly to the core experience of being an entrepreneur, and I wrote about it extensively in my new book, Move to the Edge, Declare it Center. Whether you’re solving an important problem, building a team of talented employees, or trying to make the shift to remote or hybrid offices, you will go through a moment – actually many moments – where you won’t know what to do. Most of us were trained to have the “right” answer, so the experience of not having “the” answer can be supremely uncomfortable. Knowing in advance this will happen means we can take a page from world-class athletes, performers, and Navy SEALS – we can practice making decisions when we’re uncomfortable, under stress, and facing uncertainty. The first step is admitting we don’t have all the answers, then inviting peers and colleagues to help. Second, we can use tools like post-mortems and retrospectives to test hypotheses and iterate through potential solutions. By creating a system to work through complex problems, we engage others to find alternatives, reduce our blind spots, and build the psychological safety that is a crucial element for great teams. Finally, we can practice mindfulness and meditation to make good decisions despite feeling uncomfortable. I have been meditating for 25 years and it’s still a practice that I learn from. If you practice getting comfortable with being uncomfortable in advance, when you encounter complex problems, you will have the tools to make great decisions, lead your organizations, and model the behavior you want in your colleagues.