Successful Entrepreneur Andrew Duplessie on Making a Positive Impact in the World in Light of Life’s Challenges

Lessons from an an actor, writer, and founder, who has appeared in Broken and American Horror Story.

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Mandatory Credit: Photo by Chris Pizzello/Invision/AP/Shutterstock (9483085ag)
Andrew Duplessie
Premiere of "Chappaquiddick", Beverly Hills, USA - 28 Mar 2018
Mandatory Credit: Photo by Chris Pizzello/Invision/AP/Shutterstock (9483085ag) Andrew Duplessie Premiere of "Chappaquiddick", Beverly Hills, USA - 28 Mar 2018

1) What’s your backstory?

I was born and grew up in New York City. I went to school in Greenwich, CT. I ended up getting kicked out in 9th grade because I was young and wasn’t exactly one for attending class consistently. I then went to Trinity Pawling which was an amazing experience and an incredible school. If it wasn’t for some of the things I learned there, I wouldn’t be where I am today. 

I ended up going to Tulane University in New Orleans studying Finance and Math. I was the president of the business school. Despite loving the university, the city, and the culture, I dropped out during my senior year (maybe school isn’t for me). 

Instead of going to school, I had a passion for business. So, after dropping out of school, I immediately raised $750k to launch the iOS app AskTipster.

AskTipster went through Stanford University Startx incubator, and the rest is history. 

I picked up writing when I was in my teens. When I wasn’t attending school, I wrote short stories. I finished my debut novel, a 450-page Sci-fi story that is scheduled to be published in early 2020. Today, I often share my short stories on

2) What was your spark, where did it come from?

My parents split up when I was young, which threw a wrench into my life. It was a challenging life experience but it also gave me space and independence to flourish. It was a time where I had to mature and presented me with an opportunity to try and do things on my own, my way. 

One of the first things I learned was how to make money. I also learned how to make someone else’s life easier, and charge them for it. 

My motivation comes from others who doubt me. I was always tagged as a troublemaker (sometimes I was), and that doubt fueled my fire. In fact, when someone says “you can’t” to me, it simply provides me with more toughness and spark. 

3) Many perceive the entrepreneurship as a solo journey. Who or what has helped you most along your journey?

The truth of the matter is that my mother is probably the most inspirational person in my life. She’s the hardest worker I know. My mom taught me to be versatile, be well rounded and, in turn, those characteristics and good habits will help guide both my perspective and approach to life and business. 

What’s more, my mom is also the reason I love writing stories. She has always encouraged me to explore my creative side while expressing myself. 

My childhood friend and business partner, also the Co-Founder of AskTipster, Daniel Taylor has made a huge impact on my life. He and his family always welcomed me into their home. When I needed somewhere to go, there were never any questions asked. Daniel has been a true life blessing and continues to be my best friend for more than 20 years now. Deep down, I feel more like he is my brother than a friend. 

4) How do you deal with challenges?

I become fixated on challenges and enjoy every moment of the process. My mind goes crazy on how to surpass the challenge, and I obsess over how to overcome it. 

I will devour the internet to find a person, place, or idea to accomplish what I need to do. Through and through, I am definitely a perfectionist. This can be both positive and negative depending on how hard I push myself. 

5) What are your plans for the near-future?

At this time, I am 100% focusing on DTX and our plans towards the future. I found myself fascinated with a number of new things and I have a number of exciting projects in progress and being launched. 

Soon, I am releasing my 450-page novel in early 2020. I also have a 250-page Horror Story Novella being released around Halloween of 2019. 

6) Anything else you would like to add?

Owning and launching a startup is not only a grind but the endeavor is tough. One day is your best and the next day is your worst. When I look for motivation, I re-read this story about a young man at the age of 24 diagnosed with cancer. I read it over and over because it is both inspiring and gives me the courage to keep moving forward on a daily basis. 

“The cancer diagnosis came too late to give me at least a tenuous hope for a long life, but I realized that the most important thing about death is to ensure that you leave this world a little better than it was before you existed with your contributions . The way I’ve lived my life so far, my existence or more precisely the loss of it, will not matter because I have lived without doing anything impactful.

Before, there were so many things that occupied my mind. When I learned how much time I had left, however, it became clear which things are really important.” 

Life is so short and I want to leave this world having made a positive impact.

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