Interview: Esque Dollar is an author, speaker, educator and poet

Esque Dollar is an author, speaker, educator, and poet, bringing forth stories that creatively reflect his upbringing, and formal education. Educated on the streets of Miami, the pavements at the University of South Florida, and the corridors at National-Louis University, Mr. Dollar has become a good example of what is possible through hard work, interminable faith, and obedience.

  1. When and why did you first feel the urge to get into the motivating and personal development field?

Esque Dollar: It was when I was in the black student union at the University of South Florida. I was the political actions chair and thinking about running for president. I thought to myself that I wouldn’t be here had it not been for the encouragement, guidance, and motivation that I have received from others. I wonder how many people are not reaching their potential due to a lack of encouragement, guidance, and motivation. Maybe as president I can help. And I’ve been doing it ever since.

  1. At what stage did you decide to make a living doing this?

Esque Dollar: I’ve sort of always have made a living doing this because my only professional career has been as an educator. However, in the past 4 years of my 10-year career I began to realize that I am actually really good at this. I am only limited by being at one school. The pursuit of doing this full time stems from the desire to reach and help more people. The bigger the platform, the more people I can help.


  1. How does one actually go about creating a professional living from motivating other people?

Esque Dollar: By speaking. It’s just like anything else in life. If you want to do it then you first have to do it. If you want people to pay you for it, then you have to create value and show people that you are worth the money. I started by practicing everyday in front of my students. Then other teachers would hear about me from other students and they would ask me to come speak to their class. At meetings I always made sure to say something to the people running the show knew who I was and knew that when I had something to say it is always worth hearing. Eventually people started asking me to come to other places outside of my school. Now it’s just a matter to doing a great job every time I am handed the microphone, the rest will take care of itself.

  1. Have you suffered any ‘resistance’ in your professional career and if so how have you handled that, and how do you handle criticism and negative people in general?

Esque Dollar: The resistance I see is from people who know me. It’s like they don’t want to support me until others do, then they are all of a sudden the biggest Esque Dollar fans. When I wrote my book I would have thought that my own school district would have been my biggest supporter, but so far it hasn’t been that way. As for the negative people, “It is the mark of an educated mind to be able to entertain a thought without accepting it.” That is an Aristotle quote that I use daily. I can listen to anything but I choose what sinks in and what gets erased immediately. I keep what may be constructive criticism and dismiss what doesn’t have any merit because while there are plenty of haters, that does not mean that the haters are always wrong, so I listen in case there is something there to be learned. If not, I smile and keep it moving.

  1. Do think that video is an appropriate motivational tool, and do you have any videos published for people to see?

Esque Dollar: 30% of the human brain is dedicated to the eyes so it behooves anyone who is seriously trying to make a point to not have some sort of visual aid. I have over 10 videos published on my Facebook and You Tube pages. Ranging from poems, to speeches, to things I call, “thought provocations.”

  1. How about an album with motivational speeches? Is this something you have done or will do in the future?

Esque Dollar: I did a poetry album which I consider to be motivational. It is called “The World According to Dollar,” and it is on iTunes. I am not sure about a motivational album. I may have to take that idea back to my team.

  1. When did the writing bug first hit you, and what is the title of your latest book?

Esque Dollar: I started writing in elementary school. My teacher told me I talked too much, but I had stuff to say, so I decided to write it down. It helped me avoid getting in trouble in school and my grades got a little better. My latest book is title 30 b4 30, and is 30 short stories from the first 30 years of my life. The purpose of the book is to be a model for the type of honest and open reflection that we all need to do in our lives. It’s also about learning who you are, and the only way to do that is to reflect on who you have been.


8. Which do you find more challenging, writing books, or appearing live before audiences?

Esque Dollar: writing a book is more challenging because what is written is written. I may never see the person that is reading my book to explain to them something that they may find unclear. However, in person I can answer all questions and read facial expressions which give me instant feedback for how to continue. With a book, once it’s done, it’s like ok, Jesus take the wheel…

  1. As far as you can remember, have you ever set any goals for yourself, and then failed to achieve them?

Esque Dollar: Yea, there is a story in my book about that. I wanted to graduate with a bachelor’s in education; however that blew up in my face. I don’t want to share the whole story because I want you to read the book, but it was very devastating. There was also this child hood dream about playing in the NFL, but yeah… My genes had other plans.

  1. For example, if you never sold one single copy of your book, would you regard that as a failure? And how would you handle that situation both psychologically and emotionally?

Esque Dollar: If I never sold one copy of my book it would still be a success because the success was in the completion of it. Whether it is purchased or not is extra. I am happy with myself to be able to say I wrote a book; an entire book. Perspective is so important in life. How one measures one’s own success should not be defined by anyone else. If I never get booked to speak again, if no one ever views another one of my poems, would not bother me because my happiness lies in the completion and the fact that I am doing them because I think they need to be done, not for the approval of others. Now, it would be nice if someone purchased 1 million copies, but, if that never happens, I won’t lose a wink of sleep. I’d probably lose more sleep if it did happen.

  1. Do you think that there are specific situations in a person’s life or professional career, where all the motivation in the world is just not enough to guarantee success?

Esque Dollar: No. I do not believe that. I believe that sometimes you can be a tick biting on an iron dog. Meaning our goals have to operate somewhere on planet earth. Sometimes we blame everyone except ourselves. Sometimes we just had an unrealistic goal. Sometimes our eyes were bigger than our stomachs. Sometimes your ambition can outweigh your current talent. And motivation doesn’t have to be in the form of, “you got this, don’t give up.” Sometimes it needs to say, “It looks like you bit off more than you can chew, time to go back to the drawing board and reevaluate this thing.” “Remember nothing is a guarantee except death and taxes and your wife getting on your nerves.” Lol. Everything else is living on a prayer.

  1. How would you describe the word ‘success’, and do you think you have achieved the ‘success’ you desired?

Esque Dollar: I define success in my speeches as a goal that is reached. I am successful based on that. I had goals in my life that I have reached, there are some that I am still working on, but I have hit more marks than I have missed. And that makes me successful.

  1. In your opinion, is success the only option or can failure be regarded as a positive experience too?

Esque Dollar: The experience is the reward, whether it be a W or an L. All knowledge is relevant, all publicity is good, and all experiences that don’t kill you will only make you a better version of yourself if used correctly. So no, success is not the only option, everyone has a right to fail. And both experiences can be beneficial.


  1. Besides the economic benefits, what more than anything else drives you to pursue this profession?

Esque Dollar: The fact that I know I am helping people to improve their life by always remembering where I came from and how I would not be here had it not been for those who helped me.

  1. Do you have a specific motto or inspirational slogan locked in your head which keeps you driven?

Esque Dollar: “Dominate Your Life” is what I live by. Be in control of you and all that you do at all times.

  1. Do you yourself have a mentor, or peer from whom you draw inspiration?

Esque Dollar: I have plenty. I draw inspiration from everywhere and everybody. Doesn’t have to be a famous person, they just need to do or say something that catches my attention. I don’t have any one person that I follow more than others. I try to catch it from as many different angles as possible.

  1. Besides speaking at events are you available for one-on-one or group counseling too?

Esque Dollar: Yes I am. I love the groups, it reminds me of being in the classroom.

  1. What may be one of the first thing you say to a struggling student to help improve his or her educational aspirations?

Esque Dollar: What do you want to do? Or, if you had 3 wishes, what would you wish for? And then I work backwards from their answers

  1. Stuck on a desert island, which is the one book and one music album you would have with you?

Esque Dollar: Jaz Z the Black Album and The old man and the sea.



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Rick Jamm

Journalist, publicist and indie music producer with a fervent passion for electric guitars and mixing desks !

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