From West Philly to National Champion: Kareem Rosser Talks Work to Ride, Mental Health, and His Memoir ‘When You’re Ready’
“For me, one of the most incredible things that has happened is being able to come back to the organization, give back, and serve in this leadership role. I was fortunate enough to lead a major capital campaign and strategic planning effort, and we raised more than $15 million for the organization. Now we’re able to have polo year-round in Philly. I think that’s the story I’m most proud of, and honestly, I think many people in Philadelphia are proud of it too.”
I had the pleasure of talking with Kareem Rosser. Kareem, a Philadelphia-born polo player, financial analyst, and author, has become a notable figure at the intersection of sport, philanthropy, and urban youth advocacy. Raised in the West Philadelphia neighborhood known as “The Bottom,” a name reflecting its long-standing economic struggles and high rates of crime, Rosser’s early life was marked by adversity. One of six children in a single-parent household, he grew up reliant on public assistance, in an environment where violence and addiction were common.
Despite those challenges, Rosser’s trajectory was significantly altered when he encountered Work to Ride, a nonprofit equestrian program for underserved youth based in Fairmount Park. The program, founded by Lezlie Hiner in the 1990s, offered Rosser and his siblings access to horseback riding and polo in exchange for stable work. It was a chance discovery — his brothers initially stumbled upon the stables by mistake — that soon became central to his life.
By age eight, Rosser had begun riding horses, and within a few years, he took up polo, a sport historically associated with wealth and exclusivity. He quickly distinguished himself as a competitor, eventually captaining the first all-African American team to win the National Interscholastic Polo Championship in 2011. He continued to play at the collegiate level, leading Colorado State University to a national title and earning a degree in economics before transitioning into a career in finance.
Rosser’s connection to Work to Ride remained strong after college. He served on the board and, eventually, returned to Philadelphia to take on a leadership role. As Executive Vice President of the organization, he has overseen a major expansion effort, including a $15 million capital campaign to build a year-round indoor riding facility. The project reflects a broader goal of institutional growth: increasing access to equestrian sports for young people from backgrounds similar to his own.
In addition to his executive work, Rosser has pursued writing as a means of reflection and advocacy. His first memoir, Crossing the Line, recounts his upbringing in Philadelphia and rise in the world of polo. His second book, When You’re Ready: A Love Story, published in 2025, offers a more intimate narrative, focusing on his relationship with Lee Lee Jones, a former partner who suffered a traumatic brain injury in a horseback riding accident. The memoir explores themes of love, grief, healing, and resilience, as well as Rosser’s own mental health journey in the aftermath of personal loss.
Through both books, Rosser has established himself as a thoughtful and candid storyteller, using his platform to engage audiences in discussions around trauma, recovery, and personal growth. He has appeared at events such as the LA Times Festival of Books and participates in public speaking engagements that focus on resilience, equity, and opportunity.
Rosser is also the co-founder of the Philadelphia Polo Classic, an annual event that draws thousands of attendees and aims to elevate the visibility of polo in urban communities. The event serves both as a fundraiser and a community-building initiative, reflecting his broader mission to disrupt perceptions about who belongs in equestrian spaces.
Beyond his professional achievements, Rosser is active in philanthropic work. He is closely involved with Bryn Mawr Rehab Hospital and established the Lee Lee Jones Patient Assistance Endowment Fund to support individuals facing barriers to recovery due to financial hardship. The fund aims to provide resources such as wheelchairs, aftercare services, and therapeutic equipment, with a fundraising goal of $1 million.
Rosser frequently speaks about the challenges of leadership in nonprofit organizations, particularly the complexities of scaling while maintaining an organization’s original mission. He has described the transition from beneficiary to executive as both gratifying and demanding, noting the internal and external resistance that often accompanies institutional change. His leadership style emphasizes adaptability, collaboration, and the importance of confronting discomfort in the pursuit of growth.
Reflecting on his early missteps — such as neglecting his education during middle school — Rosser has been open about the importance of academic discipline, especially in underserved communities where access to opportunity is limited. He credits the structure and mentorship of Work to Ride, along with the steady support of his family, for helping him to realign his focus and ultimately attend college.
In interviews, Rosser has identified “showing up” as a guiding principle in his work, especially in fundraising and advocacy. He stresses the importance of persistence, resilience in the face of rejection, and the value of entering spaces where one might initially feel unwelcome or unqualified.
Looking forward, Rosser envisions his legacy in terms of impact rather than accolades. He hopes that his journey can serve as a model for other young people who are navigating systemic obstacles and searching for a path forward. His broader mission, he has said, is to increase access — to capital, housing, education, and opportunity — for those who have historically been excluded from them.
Rosser resides in Philadelphia, where he continues to manage his roles in nonprofit leadership, authorship, and public engagement. Through his multifaceted work, he has emerged as a compelling voice on the transformative power of sport, storytelling, and community-based action.
Yitzi: It’s so nice to meet you. Before we dive in deep, I’d really love to learn about your personal origin story. Can you share the story of your childhood and how you grew up?
Kareem: Absolutely. I was born and raised in West Philadelphia. I’m one of six. I come from a single-mother household. I share the middle with a twin sister named Kareema.
My mom was also born and raised in Philadelphia and pretty much spent her entire life there. We grew up in a very poor household, very dependent on government assistance. As I said, my mom was a single mother who had six kids before she was 30, and she raised all of us pretty much by herself.
We lived in a poor neighborhood that was filled with a lot of crime, violence, and addiction. There were a lot of challenges we dealt with, but they were challenges many other families in the neighborhood also faced.
Life early on wasn’t necessarily easy. It also wasn’t hard, because I had my family.
It was tough growing up in West Philadelphia, especially in the area I lived in. It was called the Bottom, and it was called that for a reason. It was a very difficult place in Philadelphia.
Yitzi: Amazing. So can you tell us the next chapter? How did you become a polo star?
Kareem: I, along with many of my siblings, discovered a stable in West Fairmount Park, Philadelphia. The stable was called Shimon, but the organization is called Work to Ride. The founder and executive director, Leslie Heiner, discovered the stables in the mid-90s or so.
She learned that the Philadelphia Mounted Police, who were formerly housed there, were no longer using the facility, and the space became available. She started leasing it from the city of Philadelphia for a dollar a year and launched the Work to Ride program. At that time, my two brothers, David and Jabar, both joined the organization, and I later followed them.
It was, as I’ve described in many other interviews, the best wrong turn ever. My brothers took a wrong turn that led them to this incredible stable and to this incredible woman, Lezlie Hiner.
I showed up eventually as an eight-year-old boy. I got on a horse, started riding, and fell in love with horses. By the time I was nine or ten, I picked up a polo mallet for the first time and started learning the game.
Eventually, I got involved in playing at the high school level. Once I started playing, I fell in love with the sport. I had the opportunity to compete around the world and play polo across the country in high school. Then, in 2011, my brother, a good friend of ours, and I became the first all-African American team to ever win a National Championship in the U.S. We did it, and it’s something we still cherish and are incredibly proud of.
Yitzi: You probably have some amazing stories from your career. Can you share with the readers one or two stories from your professional life that most stand out in your mind?
Kareem: I’d say the most recent one is me serving as the Executive Vice President of Work to Ride now.
After college, I moved back to Philadelphia. I went to school at Colorado State University, then started a career in finance right after graduating. At the same time, I stayed involved with Work to Ride and served on the board.
About a year ago, I joined as the Executive Vice President. Over the last several years, I’ve been working with the organization to raise money to build a new indoor riding facility at our site in Philadelphia and expand our programming to serve more kids here in Philly.
For me, one of the most incredible things that has happened is being able to come back to the organization, give back, and serve in this leadership role. I was fortunate enough to lead a major capital campaign and strategic planning effort, and we raised more than $15 million for the organization. Now we’re able to have polo year-round in Philly. I think that’s the story I’m most proud of, and honestly, I think many people in Philadelphia are proud of it too.
Yitzi: It’s been said that sometimes our mistakes can be our greatest teachers. Do you have a story about a humorous mistake you made when you were first starting, either in polo or as an analyst, and the lessons you learned from it?
Kareem: I think for me, one of the biggest mistakes I made early on in polo was actually around education. One of the things Leslie really emphasized in the program was how important school was.
In my earlier years — specifically around middle school and early high school — I didn’t take school very seriously. That made it really difficult for me once I got to high school. I struggled with reading, writing, and all the other things school requires.
Looking back, I really wish I hadn’t skipped school or slacked off when I was supposed to be in class. I definitely paid for that later. It’s a mistake I’ve always regretted, because things could have been a lot easier if I had just shown up and done the work when I was supposed to.
At the same time, I ended up persevering. I went on to college and became the first in my family — among my brothers and sisters — to do that. It wasn’t a huge mistake in the grand scheme of things, but it was definitely something that could’ve been avoided, and my life would’ve been a little bit easier because of it.
Yitzi: Great answer. What has been the most challenging role or project that you’ve taken on so far and why?
Kareem: I would say this role as Executive Vice President. I left school and started working in finance, and fortunately, I gained many skills in that role that prepared me to serve as Executive Vice President now.
Taking on an organization like Work to Ride, which had very scarce resources and was essentially in bootstrap mode for a couple of decades, has been a major challenge. It had a tremendous impact on a small scale, but growing it to have a larger impact came with all kinds of hurdles. Fundraising, figuring out how to institutionalize something that was once so small — how to grow it and scale it without losing the special things about the organization — those are real challenges.
Learning how to deal with change is something I’m still working on in this role. I’ve been involved in the organization since I was an 8-year-old boy. Now, as a 32-year-old adult in a leadership position, there are expectations to grow and expand it. There are inevitable challenges that come with scaling any organization, whether it’s non-profit or for-profit. I’m dealing with some of those challenges now.
I think a big part of it is the challenges that come with change. Most people, quite frankly, don’t change. They’re used to their routine and want to stay in it. Facing the uncomfortable parts of change has been tough for me, but I’m navigating through it and figuring things out as we continue to grow and move the organization forward.
Yitzi: Fundraising is extremely hard for many non-profit directors. Do you have any words of wisdom from your experience about how to be successful in fundraising?
Kareem: I would say the best advice anyone ever gave me was to show up.
What do I mean by that? I mean, sometimes you get invited somewhere and you think you’re not qualified to be there or it’s a space you’re not necessarily comfortable in. I’ve met some incredible and incredibly generous people in places where I didn’t really want to show up. So the first thing is: show up.
The other thing is to be able to accept rejection, in whatever form it comes. And understand that rejection isn’t necessarily the end. I wouldn’t even call it a challenge — it’s a sign to move forward, to pivot, or to think differently.
And be patient. So: show up, be okay with rejection, and be patient. If everybody said yes, it would be easy — and it’s not. Those are my three takeaways: be patient, be fine with hearing “no,” and show up.
Yitzi: You have so much impressive work, Kareem. Can you share with our readers the exciting projects you’re working on now?
Kareem: I mentioned building the new facility — that’s my current project. I’m also the founder of the Philadelphia Polo Classic, which is a big event we host here in Philadelphia. We have about 4,000 to 5,000 people show up every year.
We’re currently planning that event for 2026. I’m also working on the grand opening of our new riding facility in Philadelphia, which we expect to open this September.
I’m still promoting my new book, When You’re Ready, which came out in February. I’m excited to continue sharing that book and my personal story, along with Lee Lee Jones’ story. We’re hoping it inspires people and gives them hope.
That’s one of many things I’m working on. I also founded the Lee Lee Jones Patience Assistance Endowment Fund, which will support families and individuals who may end up at Bryn Mawr Hospital and don’t have the means to afford aftercare or specific needs like wheelchairs and other recovery-related items.
Right now, I’m focused on raising money for that fund. We have a million-dollar goal that we hope to reach over the next year or so.
Yitzi: Can you tell us a bit about your new book and the story of Lee Lee, for readers who may not be familiar?
Kareem: My new book is called When You’re Ready. It’s a love story. It’s about my relationship with Lee Lee Jones, who is my ex-partner. She suffered a traumatic brain injury. Lee Lee had a horse accident — a horse fell on top of her, crushed her head, and left her in a horrible condition.
I write about that journey, what it was like for us, especially the day of the accident, her recovery period, and how difficult it was for me to witness and experience that kind of loss. The brain injury left Lee Lee severely injured and, unfortunately, really altered who she was as a person, as some brain injuries can.
Learning to cope with that, to heal, to accept Lee Lee in her new form and who she is now — finding the courage and ability to heal and eventually move on and find new love — I write about all of that. I also write about what love meant to me growing up and how I experienced it as a child.
I talk about my mental health journey, the challenges I faced during the recovery period, and quite frankly, even before that. It’s a very deep and personal book. I’m really hoping it resonates with people and gives them the comfort and words they might need to find deep down in order to move on.
Yitzi: What’s the takeaway or message you want readers to have after they’ve finished your book?
Kareem: I really hope people learn to show up, no matter what kind of tragedy happens in life. Also, realize that with time, you will heal. There are different mechanisms and types of help out there to get you through certain challenges, especially around mental health, loss, and grief.
I hope people take away that tough times are temporary and that things will get better over time — but you have to be patient and believe.
Yitzi: How’s Lee Lee doing today?
Kareem: Lee Lee is doing well. She’s at home in Chester County, Pennsylvania, living on a farm with her family. She still needs support 24/7, but she’s thriving. She’s alive. She’s smiling.
She and I still have an incredible relationship. She’s still a very important person in my life and always will be, as long as we’re both here on this earth. She’s doing well and still goes to therapy every day, working to get back on her feet.
Yitzi: Amazing. This is our signature question. You’ve been blessed with a lot of success. Can you share five things you’ve learned that you wish you knew when you first started?
Kareem:
- One, success doesn’t happen overnight. That’s a really important one. It goes back to being patient.
- Two, you can find value in both good and bad situations. You have to stay patient, be creative, and remain optimistic.
- Three, being a leader doesn’t mean you’re always right. It’s about having the ability to communicate, accept criticism, lean on others, and build a strong team. Leadership isn’t just about giving orders — it’s also about listening and taking direction.
- Four, a little anxiety isn’t always a bad thing. Anxiety can actually motivate you. It can help you notice things you might have missed and discover strengths you didn’t realize you had. I’ve learned to turn my anxiety into a superpower, especially since I tend to be someone who’s often anxious.
- Five, lean on your family during difficult times. My family has played a huge role in my life, especially as I’ve taken on new business ventures and risks I might not have been comfortable with otherwise. Having them around has made it much easier to face those challenges.
Those are five things I would share. I hope they can help others, whether they’re just starting out or going through a rough patch.
Yitzi: Amazing. Looking ahead, what impact do you hope your work in horseback riding and finance will have 10 years from now?
Kareem: I hope that 10 years from now, there will be thousands — if not millions — of young boys and girls from challenging backgrounds, who maybe didn’t believe they could dream big or achieve something greater. I hope the work I’m doing now inspires them.
I’m just one of many people who come from tough circumstances and have found a way to turn that into success. I want to be one of many who inspire a generation — whether it’s through our organization, in Philadelphia, or even across the country.
Yitzi: This is our final aspirational question. Kareem, because of your great work and the platform you’ve built, you’re a person of enormous influence. If you could put out an idea or inspire a movement that would bring the most good to the most people, what would that be?
Kareem: Really, it would be giving people access to real opportunity. What do I mean by that? I mean access to capital, access to quality housing, access to the basic necessities in life — food, water, shelter — without struggling. Without wondering where your next meal is coming from, or whether you’ll be able to receive the education that I believe everyone deserves.
If I could create a perfect world, a utopia, it would be a place where people have access to the essentials that allow them to live, thrive, and survive — without constantly worrying about how to feed themselves or their families.
If I had to sum it up, the movement would be about providing the basic necessities so people can thrive and survive without fear.
Yitzi: Kareem, how can our readers continue to follow your work? How can they support what you’re doing? How can they purchase your books or support you in any way?
Kareem: Please visit my website, kareemroser.com. Also visit worktoride.net, which is where all the charity work is happening. I’m on social media — Instagram, you can find me at Kareem Roser.
Those are some of the platforms where you can follow my journey and my story. I’m hoping to inspire readers, and I hope they get behind some of the causes I’m passionate about. I know people are passionate about many different things, but I see myself as one of many individuals doing good.
I don’t want to downplay what I’m doing, but I do recognize there are lots of others out there too. I just hope that when people are looking for purpose, they find something that makes a real difference. Whether it’s through me or someone else, do something that makes the next person better.
Yitzi: Kareem, I wish you continued success, good health, and blessings. I hope we do this again next year.
Kareem: Thank you. I appreciate it so much. Thank you.
From West Philly to National Champion: Kareem Rosser Talks Work to Ride, Mental Health, and His… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.