Robert W. Dempsey

One Of The Top Coaches and Speakers For Entrepreneurs

Robert Dempsey

Robert W. Dempsey
Coach. Speaker. Author. Entrepreneur.
Co-Founder of Awesome To The Core.

Over the course of my career, I have gone from being an entrepreneur at 22 to leadership positions in four corporations and back once again to forging my own path. It has been a wild journey that developed me into who I am today: a full-time, professional success coach and entrepreneur, helping and inspiring people like myself -- those who may be ready for what's next, and are ready to go after what they truly want in life, and be supported along the way.


As a lifelong business founder and owner, I have always been passionate about solving complex problems and creating solutions that truly help people. I have founded and built three startups in tech and marketing, and grew my second business to over half a million dollars in 18 months. After four years in the corporate world, I returned to entrepreneurship and am currently the co-founder of four companies: Awesome To The Core, JackESL, and Thai With Me.

I have developed and sold online applications, consulted to Fortune 500 and Inc. 500 companies, authored a book on Python development, written articles and manuals for Amazon and Intel, and spoken nationally and internationally on software development and agile project management. One of my biggest accomplishments was gaining Jack Canfield as a client for my marketing company. The website framework and user experience that we designed for his team is still in use to this day.


Much of my time over the past 10 years has focused on creating communities that foster individual and team transformations, both personally and professionally. I have worked with individuals and entrepreneurs in mentoring, coaching, and Mastermind group session capacities. I founded and grew the Data Wranglers DC meet-up group to over 3,000 members. I performed training for 60 people at Freddie Mac to help them improve their data science skills, manage their teams, and, on an individual basis, learn how to chart their careers.


Two experiences have drastically impacted my life, career, and who I’ve become: getting sober at the age of 20, and my involvement with Jack Canfield’s The Success Principles™. It was with the help of my support system all those years ago that I was able to turn things around and began to learn how to be open, honest and vulnerable —how to be the "real" me. Together with my trusted advisors, I took a deep look at my current reality and designed a plan to adjust my path, and create the life I truly wanted for myself.


When I heard about The Success Principles™ in 2012, I took it even further and was finally able to truly understand my life’s purpose. The tools I learned helped me propel myself to phenomenal levels of personal achievement.