Anna M. Bailey has found her niche and success as the managing partner of Chestnut Capital Management LLC in Jonesville, Virginia, bringing more than 15 years in her industry and crediting her achievements so far to time-tested hard work. As the owner of her company, she is an outsourced portfolio manager and chief investment officer for funds and alternative asset classes. Ms. Bailey works with fund managers to help build their portfolios, specifically focusing on investing in senior life settlements, which involves buying out life insurance policies from U.S. seniors who cannot afford them anymore or no longer need the coverage. In 2013, she was recognized for her prowess in the industry with a Lifetime Achievement Award from the European Life Settlement Association.
In addition to thriving at Chestnut Capital Management LLC, Ms. Bailey is a published author. In 2021, she wrote “The Three Day Heist” with Olympia Publishers, and in 2023, she passionately penned “Rene and a King.” The books follow the adventures of two mice that reside in her house. Early on the path to her professional and literary accomplishments, Ms. Bailey studied at the State University of New York at Buffalo, where she double majored in German and international relations, graduating with a Bachelor of Arts in 2002. As a follow-up, she earned a Master of Arts in German studies at the University of Maryland in 2007. Launching her career in financial services with Secondary Life Capital LLC, Ms. Bailey worked as a senior investment analyst from 2007 to 2009. She was promoted to director of operations in 2008 and departed the company to become the director of business development with MLF LexServ. In 2012, Ms. Bailey was hired by LifebondXchange as the business development director. Prior to starting Chestnut Capital Management LLC, she spent five years with the RiverRock Group as the director of life settlements from 2013 to 2015 and as the chief investment officer of RiverRock Funds from 2015 to 2018.
Parallel to her primary roles, Ms. Bailey served the European Life Settlement Association as an ambassador at large from 2012 to 2013. She additionally acted as the chairman and deputy chairman of the organization. Committed to giving back and patronizing the arts, she has been a donor to various elephant protection charities in Africa and a supporter of the Rochester City Ballet and the Rochester Philharmonic Orchestra. When Ms. Bailey is not busy managing Chestnut Capital Management LLC, she enjoys many hobbies, including playing the piano, writing, crocheting, gardening, playing sports, hiking, and farming. She lives on a beautiful farm in Virginia, which stands as a tangible testament to her hard work and a symbol of her dedication. Ms. Bailey also enjoys staying active by practicing yoga and Pilates.
Ms. Bailey fondly recalls the story of how her parents met when her father, a captain in the U.S. Army, was deployed in her mother’s native Germany. As a German and United States citizen, Ms. Bailey was motivated by the example set by her parents and maternal grandmother, Ruth Gäbelein, who recounted her experiences of hardship living through World War II and the D-Day invasion. Ms. Bailey was extremely moved by her grandmother’s stories and developed a deep gratitude for the opportunities she has been afforded in her life through today. This historical perspective also has emboldened Ms. Bailey with a sense of resilience and knowing she could overcome any obstacle life threw at her. Looking ahead, she is determined to continue expanding her business and fulfill her love for writing by finishing more books. Ms. Bailey also plans to renovate her house to create a more comfortable and modern space for herself, reflecting her personal style.
