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Interviews

Audio Interviews With The Prospector Team

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When evaluating an investment manager, investors tend to rely on a familiar checklist: strong, sustainable performance, a clear investment process, disciplined risk management, and exceptional client service. 
 
But what about the qualities you can’t screen for?
 
Listen to our interview series, where we dive into the perspectives, philosophies, and personal journeys of our portfolio managers to discover what inspires and informs their investment approach.

Part 1: The Prospector Story with Founder John Gillespie

Ever wondered what fuels a successful investor’s journey? Step behind the scenes with our founder, John Gillespie, as he shares the pivotal moments and key insights that shaped his approach to value investing—from early mentorship under legends like Jack Byrne and Warren Buffett to building a boutique asset management firm focused on long-term value.

In this interview, originally recorded in 2020, John sits down with Havener Capital Partners founder Stacy Havener for a conversation that goes beyond balance sheets and business models.

John Gillespie stepped back from day-to-day asset management at Prospector Partners in 01/07/2022 and currently serves as the firm’s Managing Partner. The current portfolio management team, including their bios, can be found here.

John Gillespie

Part 2: Founder John Gillespie on the Prospector Investment Approach

Many equity investors rely on their portfolio’s winners to offset the losers. John Gillespie has a different philosophy. He believes it’s important to spend as much time analyzing what can go wrong as what can go right. Avoiding large losses is woven into Prospector’s DNA, driven by a deep understanding that preserving capital is essential for compounding wealth over the long term.

In the second interview in this series, originally recorded in 2020, John talks with Havener Capital Partners founder Stacy Havener on topics you won’t find in SEC filings or fact sheets.

John Gillespie stepped back from day-to-day asset management at Prospector Partners in 01/07/2022 and currently serves as the firm’s Managing Partner. The current portfolio management team, including their bios, can be found here.

John Gillespie

Part 3: Entrepreneurship Unfiltered. Insights from John Gillespie

Few things test your mettle like building a business from the ground up. For John Gillespie, launching Prospector Partners has been a journey filled with surprises, challenges, and moments of pride. From navigating the complexities of managing compensation to creating a culture where employees thrive and stay for decades, John reflects on what it takes to foster success and find your tribe.

In this third and final interview of the series, originally recorded in 2020, John offers candid insights into the highs and lows of entrepreneurship and shares advice for those considering their own ventures.

John Gillespie stepped back from day-to-day asset management at Prospector Partners in 01/07/2022 and currently serves as the firm’s Managing Partner. The current portfolio management team, including their bios, can be found here.

Kevin O'Brien

Kevin O’Brien on Investing Against the Grain

At the core of our investment philosophy is a contrarian approach. When we uncover a business we believe in, we lean in fully—especially when the Street wants nothing to do with it. That disconnect is where opportunity thrives.

In this interview originally recorded in 2020, Partner and Portfolio Manager Kevin O’Brien discusses how he and his team put this investment philosophy into practice.

Inside the Mind of a Value Investor: A Conversation with Portfolio Manager Jay Kish

Jay Kish didn’t start his career planning to be a portfolio manager. But more than 20 years ago, when a former colleague called about a new investment firm, he took the leap—and never looked back. In this conversation, Jay shares what drew him to Prospector Partners in its earliest days, how he helped build the firm from the ground up, and why free cash flow and private market value are at the core of their investment approach.

Tune in to hear Jay’s journey, from accounting to investing—and everything in between (originally recorded in 2020).