5 Questions with Penny Jar’s Rich Scudellari

In recent weeks, we had the chance to catch up with Rich Scudellari on all things Penny Jar Capital. During our conversation, we delved into how Penny Jar Capital’s unique approach—rooted in community and inspired by lessons from the basketball court—drives innovation and connects the Midwest with the coasts.

Q: Why are Penny Jar Capital and NVNG a good fit?

RS: Penny Jar Capital and NVNG share a keen discipline and focus on community to help drive growth and innovation. A founding principle for both firms is that one plus one can equal three when backed by the great multiplier of community. In both cases, the central objective is to deliver outsized value to portfolio companies through the connections we make, doors we open, and the rigorous approach to everything we do.

Q: Can you tell us about Penny Jar’s origin story and superpowers?

RS: Penny Jar grew out of our time building the investment portfolio of SC30 Inc., the business entity of two-time NBA MVP and four-time NBA Champion Stephen Curry. We developed a thesis around combining the rigor required to identify exceptional founders with the access, influence, and reach to help drive value once we invested. We refined this strategy over the course of building a great portfolio at SC30 and then saw the opportunity to scale our capabilities with Penny Jar in 2021.

The name of the firm represents a key principle for how we approach everything we do. Penny Jar is rooted in wisdom gained from Bryant and Stephen’s college basketball coach, who started the year by putting an empty jar in the middle of the locker room. Throughout the season, when the team performed well, each player received a penny for the jar. As the season progressed, the jar slowly filled. Right before the post-season, it was completely full, showing how success is achieved by the consistent contributions of many over a long period of time. The result for the Davidson team was a historic trip to the Elite 8 of the NCAA Tournament.

By leveraging the access, influence, and reach of the Penny Jar community, we help founders and their teams fill their respective jars.

Q: What is your take on the Midwest venture ecosystem and how Penny Jar Capital fits in?

RS: There is a vibrant, emerging venture ecosystem in the Midwest. The appetite for innovation is not just limited to founders but also the incredible corporations headquartered here. We are fortunate to have boots on the ground and leverage the opportunities being here provides us.

Our unique position of having a foot in the Bay Area and the Midwest gives us an appreciation for the similarities between the two parts of the country. It also highlights the existing disconnects, and we’re fortunate to serve as a bridge between the Midwest and the coasts. We aim to be the strong connective tissue between innovators nationwide, highlighting their appetite for pushing boundaries and sharing their successes.

Q: Can you share some trends that you are seeing in venture capital within your thesis industry and stage?

RS: AI is the topic on everyone’s mind right now, and rightfully so. It’s captured the imagination of such a large swathe of the world and gained adoption across all age groups. But the most exciting effect of AI is that it’s been the catalyst for so much creativity, particularly in business.

Innovators are rethinking how work gets done. It’s not just founders looking to start something new; employees inside large corporations are pushing the boundaries. Whole industries will be rethought from the ground up, and business models will (and already have in some cases) be flipped on their heads.

This excitement drives a tremendous amount of experimentation, akin to the advent of the Internet in the 90s. We are seeing small teams do so much more, with so much less than even a few years ago. However, there are limitations to AI, and it’s crucial for founders to know what those limitations are. Unfortunately, we’ve come across some founders (and employees inside of larger companies) who overpromise and underdeliver, creating some disillusionment regarding AI in the enterprise. Often, the founders who take a steadier, more methodical approach to incorporating AI into their products are finding more success over the longer term.

Q: In your work at Penny Jar Capital, what are you most proud of?

RS: We are most proud of the community we’ve built at Penny Jar. From our core team, including Vrinda Agarwal, who joined as an investor in 2023, to the founders we back and the investors we partner with the Penny Jar community is an incredible group of individuals driving exceptional results.