Team

Jim Master brings more than 32 years of experience to The Master Investment Group, beginning his career at Hilliard Lyons before forming the team with his brother nine years later. He holds his Series 7 and 63 licenses and is registered in both investments and insurance across 37 states. Jim is known for his deep industry knowledge, steady leadership, and long‑standing commitment to client service.

Before entering the financial industry, Jim played basketball for the University of Kentucky from 1980–1984, where he once held the school record for free‑throw percentage. He was inducted into the Indiana Basketball Hall of Fame in 2013 in recognition of his athletic accomplishments. In 2024, Jim and his wife Sheila pledged a $1 million donation to the University of Kentucky, supporting both the athletics department and the Gatton College of Business—an expression of gratitude for the role the university has played in his life.

Outside the office, Jim enjoys coaching his son Leo’s basketball team, skiing, fishing, and traveling with his wife, Sheila.

Randy is one half of The Master Investment Group’s namesake and brings more than 23 years of experience to the team. He began his career in the industry at Hilliard Lyons prior to its acquisition by Baird and has built a long‑standing reputation for client dedication and integrity. Randy holds the Series 7, 66, and 31 licenses and is registered in both investments and insurance across 27 states.

Randy is deeply committed to giving back to his community. As an active volunteer with Habitat for Humanity and God’s Pantry, he has contributed his time and leadership over many years, including serving two terms on God’s Pantry’s board.

Outside of work, Randy enjoys golfing, fishing, attending Bible study, and spending time with his rescue dogs, Scout and Shadow.

Roseanna “Rosie” Black is a Client Specialist with The Master Investment Group and has been part of the team since 2021. Coming from a background in office administration and teaching, she quickly adapted to the financial services industry and earned her SIE, Series 7, and Series 66 - and became fully licensed in October 2025.

Rosie is passionate about the client-facing side of her work and takes pride in building supportive, positive relationships with the individuals and families she assists. She is known for her reliability, approachable style, and genuine desire to help people feel informed and comfortable.

Outside the office, Rosie enjoys cooking, spending time with her dog Molly, attending concerts with her husband Austin, and spending summer weekends on their boat and in their RV at Herrington Lake.