My Answer to Oprah's Question - Daily Love with Mastin Kipp

My Answer to Oprah’s Question

By David Monroe

San Quentin State Prison

While reading The Dragonfly Effect and reflecting on a quote from Oprah Winfrey, I found myself lost in my own thoughts pondering the answer to her question from a Last Mile perspective, and then from a personal brand standpoint. Oprah asks, “What’s the most important message you want to leave your audience with and why should they care?”

From a Last Mile perspective, we want to leave you with the message that change is possible and that we all have redeemable qualities. The Last Mile focuses on business literacy  and developing  entrepreneurial  skills  within  the  men  it  fosters,  but  more importantly, by the end of Demo Day, they have also built confidence, restored pride, and allowed the men an opportunity to tell their stories. These things may not seem that important to society, but trust me, they should be. The facts are that almost every prisoner will be released at some point and placed back in the community that they once menaced.

The Last Mile believes that it is important to send these men (us) back reformed and with the same confidence and pride that guided us through developing our own businesses, executive summaries, and then giving a presentation in front of our peers and the likes of the Secretary of CDCR, Matthew Cate, California first lady Mrs. Anne Brown, and The Wall Street Journal.

From a personal brand standpoint, I admit that the 15-year-old David Monroe was nothing short of a menace to society. However, I am no longer 15-years-old. I am now 30 and after spending the first half of my life on the free side of these prison walls, now I have spent the last half locked away behind them. To say that I have taken advantage of an opportunity would be an understatement. Since coming to the notorious San Quentin State Prison in 2003, I have obtained my GED and college (Associate of Arts) degree, while becoming a certified tutor through the Marin County Literacy Program. I have worked with at risk youth for the last 9+ years and have made a huge impact on some of their lives through my story and guidance. I have taken numerous self-help groups such as, TRUST (Teaching Responsibility Utilizing Sociological Training), IMPACT (Incarcerated Men Putting Away Childish Things), VOEG (Victim Offender Education Group), Alliance for CHANGE (Creating Hope And New Goals Ethically), Non-Violent Communication, Change Is Possible, No More Tears, Richmond Project, Developing a Positive Attitude, Narcotics Anonymous, etc.

And now I am also a product of The Last Mile and proof that change is possible. No one should be defined by their single worse act because it is what they do after it that tells you what kind of person they are. I am proof of that as I have made huge strides in purging my old behaviors, resolving my bad attitude towards life and people, and opening up to who I really am. All of this is key in my personal growth and transformation.

Hurray for me, right? No… hurray for all of us. You should care because I will be released in the near future, and it is important that I get all of this help so that I can return with the tools necessary for a successful transition and the maturity and integrity to function as a responsible adult. The truth is that these programs work and they minimize any chance of recidivism, criminal behavior, and most importantly, causing any harm to you or the community.  I hope that all of you care about the change that goes on behind these prison walls. I care because I want to do better and be better, and the support and humanity of society helps. So my hope is not only that you will care, but also that you are willing to help.


All communications between inmates and external channels are facilitated by approved volunteers since inmates do not have access to the internet. This program is part of The Last Mile San Quentin. @TLM