I Love My Job: Philly Youth Basketball CEO Kenny Holdsman

The leader explains how the local organization creates opportunities for disenfranchised kids across the city.


Photo by Isaiah Nathaniel

Kenny Holdsman was CEO of Philly’s Arthur Ashe Youth Tennis and Education — now called Legacy — beginning in 2009, but when he saw an opportunity to start a new community organization that could leave a lasting impact, he decided to leave Arthur Ashe behind in 2015. That organization he created would later become Philly Youth Basketball (PYB).

As CEO, Holdsman devotes 75 hours a week to creating opportunities for young people — especially those from under resourced families and communities — to help them achieve their potential as students, athletes and leaders. PYB runs a series of yearlong programs that help students with academics, health and nutrition, leadership development, basketball skills building and game play. And a large part of PYB’s staff are people of color from the same communities as the students they serve. Holdsman talked to BizPhilly about his goals for PYB, working with Kobe Bryant, why he’d love to work with Joel Embiid and more.

I grew up in… Elkins Park, in Cheltenham Township.

I’m inspired by… the struggle to provide access and opportunity for lower income kids of color.

The best part of my job is… working in community with a number of twenty-something superstars from diverse backgrounds, who comprise the backbone of our staff team.

I wanted to grow up to be… I didn’t have a specific profession [in mind],  but I wanted to grow up to do something of value, to help people and make the community better. I am devoting 75 hours a week to the best of my abilities in pursuit of youth empowerment and social change more broadly.

One thing I want people to know about PYB is… that we are building an impactful program, organization and center to help thousands of young people transform their own lives in a city that is challenging for kids in low-income communities.

I started PYB because… there was an opportunity to use our city’s most iconic sport with iconic people of the sport to drive positive change on a big scale with authentic grassroots leaders at the forefront.

In five years PYB will be… one of the most innovative, impactful, youth development and community change organizations in our country.

When I started PYB I wish I knew that… startups are never linear. You can have the most well-developed operating plan, but variables emerge and evolve, which require the leadership to be agile and humble.

The best piece of career advice I’ve been given is… to align your knowledge and skills with your passions and values.

The piece of career advice I always give is… use your 20s to sponge up as much learning as possible and to find a set of mentors who are going to be deeply invested in your career and life success.

My most significant career accomplishment is… successfully pivoting from a legal career at Ballard Spahr to the non-profit sector. It’s hard to adapt and be immersed in professional environments that are far different than the one in which you’re working.

The hardest part of my job is… getting a good night’s sleep after a day that is chop filled with inspiration and challenge.

I got my first job when… I was 21, working as a legislative assistant on Capitol Hill in Washington D.C after college. I got paid $19,000. I lived in a group house with three other guys from Philly, and we cooked a lot of food and hit a lot of free and reduced priced happy hours at the great neighborhood bars and restaurants in D.C.

One person I’d like to work with but haven’t is… Joel Embiid. Jo has charisma and power that can be deployed in truly positive and impactful ways in the lives of young people in Philadelphia.

Working with Kobe Bryant was… off the charts inspiring. Not necessarily for me, but to see the way in which he and his book captivated the hearts and minds of PYB’s young people at the Hamilton School in West PhIlly. Kobe validated the importance of personal and intellectual growth and learning, well beyond one’s pursuit as a baller.


I am most passionate about… using the social capital in our community to create access and opportunity for disenfranchised kids and adults to self-determine their futures.

Basketball is… a game that fundamentally disrespects the lines of race, ethnicity, neighborhood, economic-circumstance and other lines that typically divide people. I would say that basketball is both iconic in our city and it has the lowest economic and cultural-barrier to entry of any game around.

I’ve always been bad at… discipline at the dinner table. It’s true — ask my kids. I love people, and I love eating and drinking. I can sometimes do that at excess.

My places to eat in the city are… McMenamin’s Tavern in Mt. Airy and the new Fitler Club in Center City. At McMenamin’s, I get wings and beer. At the Fitler Club, I like Marc Vetri’s flatbread pizzas.

On weekends, I… play basketball, tennis, and hang out with family, friends, our dogs and occasionally with my son’s friends if I am allowed to participate.