This week I received the heartbreaking news that my friend and once client, Reggie Osse transitioned from this life.
Reggie bravely announced that he had been diagnosed with colon cancer this past October. Although I knew this was a serious and challenging form of cancer, I just knew he would beat it, because things like that aren’t supposed to happen to good people who have a love for life. Plus he was a fighter and this was supposed to be a part of his already full life story.
Or so that’s what I told myself.
Prior to Reggie’s passing a childhood friend of mine, same age as me (33), died from heart failure over the weekend, and the father of my sisters Goddaughter was killed the day before in Baltimore.
But Reggie’s death inflicted a different type of pain. It rocked me to my core and if I am being honest, I have cried about it every day this week.
I met Reggie in July of 2016 when my friend Chevon Drew pitched me to be on his podcast. It was following the bank black movement and I noticed he was speaking about finance on Twitter so I decided to shoot my shot, asking her to connect me to him.
Off the strength of Chevon’s word, he confirmed me as a guest and I spent the days leading up to the interview re-listening to episodes preparing for what would be one of the biggest and most memorable podcast interviews of my career.
I arrived at their studio in the financial district and exchanged nervous chatter as I waited for him to arrive. As a woman who has been around men in hip-hop before, I’ve been in uncomfortable situations and I was praying that this wouldn’t be that. Before starting our interview I gave Reggie a bottle of Hennessy (a gift suggested by Chevon) and one of my Affirmations of Abundance cards as a token of my appreciation.
Reggie practiced Buddhism and we shared similar beliefs about the power of our thoughts. He happily accepted the affirmation card which read “ My Actions Create Constant Prosperity” and we proceeded to conduct the interview.
I felt like I was speaking to a friend. Throughout the interview, he politely coerced me off my “financial high horse” and helped me deliver information in a way that was digestible and effective. I’m more conscious of how I speak about money today because of my interview with him.
A few weeks later Reggie reached out to me about a few personal matters he was dealing with and asked to work with me. I rarely accept financial coaching clients but decided to take him on.
Our schedules limited us to four sessions but during those sessions, I learned so much about him including how much love he had for his children and how much he loved the work he did. Financial sessions often become therapy and during our sessions, we discussed his fears, his hopes, his dreams, his regrets. I got to know him better than most people had the pleasure to in a condensed time period.
As my circle expands to include individuals that many hold in high regard I’ve learned to eliminate expectations about who these people really are to avoid being let down.
Reggie didn’t let me down.
He inspired me and reminded me that there were good people in this industry. Men who treated women with respect and operated with integrity.
He was refreshingly intelligent, genuine, relevant, insightful, compassionate, and giving. Our last in-person meeting was during my trip back to NY in May of 2017. At this point, I had been working with him for a few months so we scheduled lunch. I’ll never forget him walking into the restaurant, smiling, yet exhausted.
It was the morning after the release party for Mogul and he was still vibrating high from the celebration. He was so thrilled about the reception of the project and felt that he had done Chris Lighty the justice he deserved. Talk about irony. Reggie spent a good portion of the last year of his life uncovering Lighty’s legacy and today we are on the eve of uncovering his.
Just three weeks ago I text him after someone from Loud Speakers Network reached out to me about hosting a podcast, thinking he had made the connection despite his battle with cancer because that is the type of person he was. He shot me back a text saying “Nah, but that’s a good look!”.
That was our last conversation.
I’m still coping with the death in the age of social media. One moment people are here, documenting their lives and then… they aren’t and their timelines stop updating.
As my husband and I prepare to have children I often ask people who have children, why they had children. A common response is to “create a legacy”. But I don’t believe that children are here to extend our legacy. They should be free to live their lives in their manner. Our legacies are what we leave behind, not who. But hey, this is coming from a woman who listens to Beyonce’s “I Was Here” before speaking engagements so I’m slightly obsessed with leaving artifacts.
Reggie Osse not only left a legacy, he left a huge dent in this world and a gaping hole in the hearts of those who knew him and loved him.
He touched the lives of many. Just search “Combat Jack” and you’ll see the stories, comments and threads of the lives he touched as a son, husband, father, friend, lawyer, storyteller, co-founder, supporter, and historian.
As I read messages we exchanged over from this past year I think what pains me about his death, is that he was just getting started on this newest vision of his life and he was so excited about it.
Sorrow aside, I’m thankful we will always have his voice. His stories. The collection of his thoughts that went on to become the best hip hop podcast the world has seen.
His mission was to demystify and humanize our culture and he accomplished that beautifully.
Sending love to his children, Akim, King, and everyone who loved him. Know that he loved you too.
In the wake of Reggie’s passing, I encourage you and myself to think about what it means to create a legacy and commit to doing something daily that builds on our legacy. That’s what he would encourage us to do.
Dream those dreams and live those dreams, because a life without dreams is black and white and the universe flows in technicolor and surround sound.
Travel in peace my friend.
Here is the podcast episode I recorded with him