Sterling Hawkins | The Legacy Project | Leadership Speaker


Sterling Hawkins is out to break the status quo to create what’s actually possible for humanity in our time. He has spent his career igniting new views and inspiring people to act on them. He went on to be involved with the launch, growth or investment in over 50 companies.

Today, Sterling reviews over 1,000 new technology companies every year further refining the keys to realizing breakthrough innovation and giving back that experience as a mentor to leading entrepreneurs working through exponential growth. He is the co-founder of CART, a platform to drive adoption of emerging technologies at fortune 500 companies.

What drives Sterling Hawkins? | I’m constantly driven to realize the full potential in myself and others. There’s this funny thing about potential — we treat it like it’s real even though it’s not yet. We might even say to each other: “you have so much more potential!” or “your business has the potential to…”. I’m about not just seeing that potential, but taking the steps to make it real.


What do you think is often the difference between people who are good at what they do and people who are great at what they do? | What makes people great is a commitment to excellence over time. Most people can do an 80% job; it’s the attention to small details adding up over time that brings it to that 100%. We’re all capable of it, it just takes a tremendous willpower to continually stand for that greatness.


What has been your biggest failure / learning experience? | I have two actually. The first came when the group that acquired my first company raised over $550 million USD before going bankrupt. The company was great at spending more — first class tickets, parties at the Four Seasons, bringing in high-profile business people . I was ready to retire and buy an island with my holdings. I left before the bankruptcy, but I learned how not to operate a business and what not to do. Maybe more importantly, I learned that satisfaction, fulfillment and real innovation come from within, not the external world.


The second was about five years ago when another business I had fell apart. At the time is coincided with some family issues, a romantic relationship ending, and I had very little cash. It was like my life had become a bad country song. But my mom, quoting Robert Frost, told me, “The way out is through.” I realized the path to success and to fulfilling potential was by owning and doing the hard things in the future.


What are the principles and values that you believe are important to live by? | The highest principle I live by is integrity and honoring my word. I am always going to try my best to do what I say I’m doing to do and if I can’t, I tell people straightaway. It takes integrity to build not just businesses, but personal relationships.


On a psychological or mind-set level, how do you use your mind and how do you think in a specific way to help you achieve your goals and realize your ambitions? | Plato said, “Necessity is mother of invention.” Whenever something has me stuck, I come back to that quote. Whatever that thing is, it’s by embracing it fully that I’m able to see it clearly and see it as something to use to my own advantage. Things either can happen to you or for you. I chose to see obstacles as they’re happening for me to extract the potential from the chaos.


How do you deal with self-doubt, fear or negativity? Can you share a time in which you either doubted yourself the most or had great fears, yet faced up to them and conquered them? | I continually push the boundaries of what’s possible for myself, not only psychologically but physically. I do all sorts of adventure activities like skydiving, 100 mile bike rides, shark diving, etc. I push my feelings of nervousness to edge of discomfort and breakthrough that boundary. Physical resilience develops mental resilience since it’s the same biological response. Doing demanding physical challenges helps keep my brain and my body in the physical world so I don’t get caught up in my own head.


How do you ensure you are always feeling energised and performing at your peak? | To be truthful, I don’t always perform at my peak. But to get closer to that peak, I use two things. First, I exercise. I practice yoga almost everyday. It’s great physically and mentally because it resets my body and mind from day before.

Second, I rely on the support of the people around me. They can hold me to a higher standard than I see for myself and keep me accountable for the things they know I want to do.


What resources (people, books, environments, movies, music etc) do you use to keep yourself inspired, informed and growing? | It takes a lot of resources :). First, there’s the support of people around me in various capacities, especially my friends and family. They help pick me up when I’m down.

I listen to a couple books on tape every week to develop my knowledge and be inspired.

I put myself in ecologies of people that have similar aims to my own. For example, I like to spend time with people who have a stronger yoga practice than me so I can deepen my own practice. Or I have lunch with  business mentors who can lend new perspectives and advise around what I’m up to.

I actually try to stay away from the news because it’s pretty alarmist nowadays, but when I do read the news, I look for things I can learn from people in all situations.

Good live music or movie every now and then doesn’t hurt either.

Interview Questions

Booking details
  • Base price ({{ repeatDayCount }} {{ config.calendar.range_mode === 'nights' ? "nights" : "days" }})

    {{ priceFormat( pricing.base_price ) }}

  • Total

    {{ priceFormat( ) }}

View further interviews.

The Legacy Project

Katie Spotz is an adventurer, acclaimed motivational speaker and a passionate safe water advocate. She became the youngest person to row solo across the Atlantic Ocean and was honoured as ‘Woman of the Year” in 2011 not only for her feat but for the inspiring example she sets to others. Katie Spotz Definition Of Success […]

The Legacy Project

Braam Hanekom is the founder and chairman of People Against Suffering, Suppression, Oppression and Poverty (PASSOP), which works for refugee rights. He was named one of Mail & Guardian‘s 200 Young South Africans. Braam has also been published in the University of Pennsylvania Law School Journal and was awarded the 2008 Inyathelo award for youth […]

The Legacy Project

Our dream when we started CA Connect was to be the first private SAICA[1]-accredited CTA[2] in South Africa that offered contact education to students who were not able to study on a full-time basis. We wanted to run a programme that was founded on inclusion, support and genuine care taking a fresh look at education, […]

The Legacy Project

Nominated to the Women in Finance Awards in 2016, Inna Rosputnia is known as the female trader who turned $10k into $3,000,000 in just a few years of trading. She has run one of the fastest growing investment companies and was recently named “Wall Street Queen” by one of the bankers during the Women Economic […]

The Legacy Project

Vicky Colbert is the Founder and Director of Fundación Escuela Nueva, and co-creator of the Escuela Nueva pedagogical model, known for its effectiveness in improving the quality and relevance of basic education in underprivileged schools across Colombia and beyond. She is the 2013 WISE Prize for Education Laureate. Vicky Colbert of Success | For me […]

The Legacy Project

Dorie Clark | The Legacy Project is an Adjunct Professor of Business Administration at Duke University’s Fuqua School of Business and the author of Reinventing You (Harvard Business Review Press, 2013) and Stand Out (Portfolio/Penguin, 2015). A former presidential campaign spokeswoman, she is a frequent contributor to the Harvard Business Review, TIME, and Entrepreneur. Recognized […]

The Legacy Project

Exploring the online realm via his areas of interest namely wine and education, Sam Paddock has developed Get Smarter with his brother Rob Paddock. Aiming to improve lives through better education, the brothers lead a dynamic team showing groundbreaking results. As a key note speaker, Sam also educates via his personal blog and here, shares […]

The Legacy Project

Ryan Carson is an entrepreneur and the co-founder of Treehouse, a online interactive education platform that teaches students how to make websites or mobile applications. The company is revolutionizing the tech-education space as it continues to grow with over 70 000 active students . The Essence of Tree-house | It’s an online technology school.  So […]

The profiles and images embedded on these pages are from various interviews conducted by The Legacy Project.

These remain the property of its owner and are not affiliated with or endorsed by WeSpeak Global.

© All rights reserved 2024. Created by Hesketh Media LLC

1902 Wright Place, Carlsbad, CA, 92008