Spotlight : : Derron Payne- The Art of the Pivot

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by Derron P.

Born in Brooklyn, NY, Derron Payne attended Rockland Community College as an honor student, where he received his associate’s degree before transferring to the McDonough School of Business at Georgetown University for a bachelor’s degree in Management and Marketing.

As a former basketball standout, he spent thousands of hours playing as well as competing for national championships. About a year into his collegiate career, he pivoted away from his first love, basketball, to his current love, entrepreneurship. Since then, he has transformed into a serial entrepreneur, co-founding the award-winning start-up, SmallTalk. Derron is also the CEO of Woodn Case.

Derron is currently in the process of publishing his new book, the Art of the Pivot, where he discusses the challenges of pivoting from one dream to the next. Many early entrepreneurs struggle to initially have the courage to take a leap of faith and follow their dreams and passions. We took the time to ask Derron a few questions about his book and the key lessons readers will take away from the Art of the Pivot.


1. Tell us a little about yourself and the inspiration behind the “Art of the Pivot?”

I’m a student in the McDonough School of Business at Georgetown University majoring in marketing and management, minoring in entrepreneurship. I am a first generation American citizen as well as a first generation college student who is originally from Brooklyn, NY. My parents and most of my family are from Trinidad and Tobago. The inspiration behind “The Art of the Pivot” came from my personal pivot away from basketball and toward entrepreneurship and business. I believe that the story of my pivot and the story of many other pivots included in the book could potential help so many people.

2. What were the biggest challenges you faced when deciding to make your pivot?

My biggest challenge was internal, it was a struggle getting myself to do something thing that I wasn’t accustomed to. Basketball was my first love, my entire life. Going to workouts, practice, and games, were the only things I knew for a long time so it was tough trying to program my brain to do something else. I talk about all of the challenges that I faced in the book but the toughest of them all was turning down the opportunity to play basketball at a 4 year school in order to attend Georgetown University.

3. In your book, do you draw on any examples from individuals who made successful pivots in their career?

I definitely draw on examples from multiple people with different types of career pivots, this was because I wanted to be able to reach and help as many people as possible. My favorite career pivot story is about a rapper turned actor who is pretty popular to many of us. I won’t say exactly who it is but you can find that story in Chapter 3 when the book releases in July.

4. What are a couple of lessons you want people to take away when they read the book?

There are so many lessons that I want people to take away from this novel, but the two most important lessons are that mentors are essential no matter what you are doing, and you raise your chance of success when you have a solid plan in place.

5. A lot of people are interested in writing a book and telling a story. What are some tips you have for those who want to write a book, but don’t know how to get started and stay committed?

You literally just need to start, most people who tell me they want to write a book have never written anything. If you feel that you want to write a book or tell a story, just start writing; you can always edit after. When I first started writing I was nervous about what people would think, but just write and edit later. To stay committed, I would say find people to hold you accountable. It helped that I knew people who were writing books as well so we kept each other accountable which was super helpful, especially with all of our other commitments.

6. What advice would you give to someone who feels they are too young, too old, or simply feel like they missed their opportunity to follow their dreams and make their desired pivot?

Most pivots are possible with the right game plan. Once you identify that you want to make your change, try to find some people in the field or position that you want to be in and figure out how they got there. Whether it’s through talking to them or researching them, figure out what their game plan was. Then with all of the knowledge that you have gained, tailor a game plan specific to you. Also, be sure to remember that there are multiple paths to every destination.

7. We ask all our guests this question last: what does being a mogul mean to you? How do you embody the spirit of a mogul?

A mogul is someone who inspires others, someone who is influential, someone who doesn’t necessarily follow the status quo, someone who creates something (business, book, podcast, music, etc), someone who can get people to follow them. Being a mogul is also about the mindset you have. Moguls are determined, stubborn, ambitious, and they have the unique ability to connect and relate to people. I believe I embody the spirit of a mogul by not following a traditional path to success, but by creating my own roadmap and trying to inspire as many people as possible along the way.

You can follow Derron on instagram @dpayne_14 and visit to learn about his book Art of the Pivot releasing in July!