An Evening of Inspiration with Stephen Curry

By Rich Scudellari


As 2023 comes to a close, we were fortunate to host many of our founders, investors, business partners, and friends at Penny Jar Capital’s holiday party in San Francisco. The gathering was a wonderful opportunity to reflect on the year and bring together the people who’ve been with us every step along the way.

The evening was punctuated by an incredible fireside chat with Penny Jar Strategic Advisor and Anchor Investor, Stephen Curry and Penny Jar Co-Founder, Bryant Barr on leadership, teamwork, and finding your “why.” As only long-time friends can, they went deep on various topics and surfaced perspectives that have crystallized for Stephen over his life as a world-class athlete, philanthropist, investor, and entrepreneur. Among the many, a few stood out as particularly meaningful and relevant to nearly everyone, no matter what they’re working towards.

Don’t complain about that responsibility. Even if I don’t have the answer, I’m going to search for it.

Leadership Is Not Convenient

Stephen will hear a common refrain when his team faces challenges: “Sorry you are having to deal with this.” He pushes back on that perspective because leadership is not a selective exercise where you can opt in and out when convenient. It’s easy to assume a role at the front when things are going well. However, the true definition of leadership is stepping up when things are hard, getting curious, having tough conversations, and looking for solutions, because that is what the team requires. When facing true, sustained adversity, real leaders reveal themselves.

Elevate Others By Speaking Their Language

Leadership is not a one-size-fits-all approach. On a basketball team with twelve different athletes who can see the floor, there are twelve different personalities, twelve different perspectives, and twelve different sources of motivation coming together to achieve a common goal. As Stephen highlighted with a few anecdotes, a leader cannot expect a singular approach to elicit the maximum potential of everyone on the team. Instead, he tries to understand each person individually, what makes them tick, and how to reach them in a way that pulls out the best they have to offer to the whole unit. This applies not only to teams in the NBA but also to teams in any setting. You need to know the players around the table and what it will take from you, as a leader, to get the best out of them.

The process of what I commit myself to is the most fun I have, and it shows up in the biggest moments.

The Process Shows Up In The Biggest Moments

A night after hitting several crucial shots to bring the Warriors back to beat the Boston Celtics in overtime, many questions revolved around Stephen’s uncanny ability to perform under pressure and deliver in big moments. He credits the process. The formula for a winning shot is not created in a moment; instead, those big moments reveal his process to get there. The relentless focus on precision, the unforgiving conditioning work, the maniacal repetition, and the unflinching commitment to his craft show up every time he hits the floor. He provided us with a stark reminder that the highlight reels result from tens of thousands of unceremonious moments of hard work when nobody is watching.

Stephen always brings plenty of tangible inspiration to our founders, investors, and team at Penny Jar.  Last night, he shared how he strives to never lose sight of the privilege of his journey, saying he “gets” to do the work, not “has” to do the work. It’s how we feel about our work together at Penny Jar, and we can’t wait to put more pennies in the jar for our founders.

Photos by Via Imagery