In this episode of The Rainmaker Podcast, Gui Costin sits down with Andrew Fentress, Co-Founder of ACRES Capital, to discuss his career path, the formative experiences that shaped his leadership style, and the lessons he carries forward from multiple market cycles. The conversation blends personal background with practical insights on sales, investing, and long-term platform building. Fentress begins by tracing his early life in the Washington, D.C. area, where he grew up surrounded by competition, entrepreneurship, and professional athletics. Exposure to business builders and elite performers at a young age instilled an appreciation for discipline, preparation, and accountability, themes that recur throughout his career. That competitive mindset was reinforced at Boston College, where he spent four years on the varsity sailing team, learning how consistent effort and teamwork translate into performance under pressure. After college, Fentress entered the workforce through a direct sales role outside of financial services, gaining early, hands-on experience with prospecting, persistence, and client engagement. Recognizing the need for stronger technical and financial grounding, he later pursued an MBA at UNC’s Kenan-Flagler School of Business. Graduate school proved to be a critical inflection point, equipping him with the analytical tools and language necessary to operate effectively in institutional markets. His entry into Wall Street came through opportunistic networking rather than a traditional recruiting path. A last-minute opening in Morgan Stanley’s summer analyst program provided the gateway into institutional finance, where he went on to build foundational skills in communication, risk-taking, and navigating complex organizations. Fentress describes the trading environment as a daily test of judgment and accountability, where feedback is immediate and credibility matters. In the mid-2000s, Fentress transitioned into private credit, helping to build a platform at a time when the strategy was still relatively nascent. That experience, combined with living through the Global Financial Crisis, shaped his long-term perspective on risk. He emphasizes that credit investing is ultimately defined by losses avoided, not just returns generated, a lesson that continues to inform his approach today Those lessons became central when Fentress co-founded ACRES Capital. He explains that the firm was built with a risk-first mindset, emphasizing discipline, downside analysis, and alignment across the platform. Rather than optimizing for short-term market conditions, ACRES was designed to endure volatility and perform across cycles. Throughout the episode, Fentress also highlights the importance of staying close to clients and assets. Being on the road, meeting investors, and seeing markets firsthand is not just relationship-building, it’s a critical learning tool. For him, real insight comes from continuous exposure to people, properties, and conditions on the ground. The conversation ultimately underscores a consistent message: durable success in investing and sales comes from preparation, humility, and respect for risk. Cycles change, markets evolve, but discipline and curiosity remain enduring advantages. Tired of chasing outdated leads? Book a demo to see how Dakota Marketplace simplifies your fundraising process with accurate, up-to-date investor data.
