🎙️ Upside Chat with C.J. Watson, Former NBA player Turned Investor and Author of Children Books.

Today we have the honor of interviewing C.J. Watson, a former NBA player (Chicago Bulls, Warriors, Broolyn Nets) turned investor and author of children books.

C.J. Watson is a former professional basketball player who transitioned into a successful career as a children's book author and philanthropist. Born on April 17, 1984, in Las Vegas, Nevada, Watson played college basketball at the University of Tennessee, where he became the school's second all-time leader in assists and steals. Despite going undrafted in the 2006 NBA Draft, he embarked on a professional basketball career that spanned over a decade. Watson played for several NBA teams, including the Golden State Warriors, Chicago Bulls, Brooklyn Nets, Indiana Pacers, and Orlando Magic, and also had stints overseas in countries like Italy, Greece, and Turkey.

After retiring from basketball, Watson focused on inspiring youth through literature. He authored the "CJ's Big Dream" series, which includes titles like "CJ's Big Dream," "CJ's Big Project," "CJ's Big Moment," and "CJ and His Magic Socks." These books aim to motivate children to pursue their dreams and overcome challenges by believing in themselves and working hard.

In addition to his writing, Watson is dedicated to philanthropy. He established the Quiet Storm Foundation in his hometown of Las Vegas, focusing on providing educational opportunities and resources to underprivileged youth. Watson's journey from the basketball court to authorship and community service exemplifies his commitment to making a positive impact beyond sports.

You can check out and buy CJ’s books here on Amazon by clicking on the link below:

📝Show Notes: Through this interview, we touched on his background, his journey to become an NBA player, his transition to investor and now author of children books. We also discussed what values or traits he is usually drawn to when he looks at the companies or founders he is looking to invest in, and how his sees his role as more than just providing capital. Lastly we discussed what he wants his legacy to be, not just as an athlete, but as an investor, author, and role model for young people.

You can read the full transcript of the podcast interview with C.J. located at the top of this blog post.

Here are the best quotes from the interview with C.J.:

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1. From the Court to the Boardroom

Question: "Tell me about your background. How did your experiences in the NBA shape the way you approach investing and business today?"
Quote:

“I wasn’t a superstar—I was undrafted, played overseas, grinded through the D-League, and eventually played ten years in the NBA. I’ve been the last guy on the bench and a starter, so I’ve seen every role and every type of team. That journey taught me resilience, patience, and how to assess situations from different angles. In business, especially as an investor, those same lessons apply. You have to do your homework, know when to take risks, and keep your ego in check. Being in the NBA, you learn quickly that talent only gets you so far—it's your work ethic and your mindset that carry you. I apply that same mentality to every business opportunity I look at.”

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2. Purpose Behind the Pages

Question: "What inspired you to start writing children’s books, and what messages are you hoping to pass on to the next generation?"
Quote:

“Honestly, writing children’s books wasn’t something I planned. I was sitting on the couch after I retired, thinking, ‘How can I keep inspiring kids if I’m not on the court anymore?’ I wanted to share my story in a way that was relatable, positive, and lasting. So I called a former coach who had written books and just dove in. My first book is about making it to the NBA through hard work. The others focus on things like the importance of doing your homework, handling bullying in a positive way, and expanding your worldview by traveling. Each one comes from my real-life experiences growing up in inner-city Las Vegas and the values my parents instilled in me. It’s about showing kids that they matter, their dreams are valid, and they can overcome anything.”

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3. Transition and Identity

Question: "Many athletes struggle with life after sports. What was the hardest part of your transition, and how did you find a new sense of purpose?"
Quote:

“The toughest part was finding my identity beyond basketball. For so many years, that’s who I was—CJ Watson, the basketball player. But even during my career, I was intentional about preparing for life after. Every summer I’d do internships—at Google, EA Sports, American Express, in real estate—just to see what else I liked and to build experience. I didn’t want to be one of those guys who had no plan after retirement. When I did stop playing, I focused on being present for my daughters—going to their school plays, being there for them daily. That helped center me. Writing books, investing, and running a foundation all gave me a new purpose: to inspire and uplift others, especially young people.”

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4. Investing with Impact

Question: "When you look at the companies or founders you back, what values or traits are you drawn to, and how do you see your role as more than just capital?"
Quote:

“I’m drawn to people who are hungry—founders who are resilient, passionate, and mission-driven. I co-invest with some of the top VCs and follow a thesis I learned from my mentor, Rashan Williams. Since 2020, I’ve invested in over 30 companies, but I don’t just write checks and disappear. I try to add value—whether that’s connecting them to people in my network, helping them think through strategies, or amplifying what they’re doing. It’s about creating real change, especially in communities like the one I grew up in. I want to back companies that are not only profitable, but purposeful.”

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5. Legacy and Leadership

Question: "What do you want your legacy to be—not just as an athlete, but as an investor, author, and role model for young people?"
Quote:

“I want to be remembered as more than just a basketball player. I want people to say I was someone who gave back, who cared about the next generation, and who used his platform to do good. Whether it’s through my books, my investments, or my foundation, everything I do is about helping others believe in themselves and reach their full potential. My legacy, I hope, is one of purpose, impact, and generosity. I want kids to look at me and say, ‘He made it, but he didn’t stop there—he brought others along with him.’ That’s what really matters.”

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