SIDEBAR WITH BEC PODCAST
STORYTELLERS?
WE'RE STORY MAKERS
Conversations with professionals shaping narratives behind the scenes—where strategy, culture, and influence intersect.
About Sidebar Consulting
At Sidebar, we exist to empower founders, executives, and creative professionals with the guidance, clarity, and operational excellence needed to grow with confidence. We combine corporate advisory expertise with culture-forward thinking to solve the real challenges businesses face in an increasingly complex marketplace.
OUR TEAM
Rebecca Paige Caplinger
CEO // FOUNDER
Rebecca Paige Caplinger is a legally trained Gen Z professional working at the intersection of law, entertainment, and digital influence. With a B.A. in Criminal Justice & Sociology (Psychology minor), an M.A. in Homeland Security, and a J.D., she combines legal expertise with modern brand strategy to help creators, artists, and businesses protect their work, expand their reach, and grow with confidence.
She is the Founder of Sidebar Consulting, where she helps lawyers modernize their brands and business development through impactful digital strategy. Rebecca also serves as Business Development & Digital Marketing Manager at Zarif Law Group P.C., leading growth initiatives across capital markets, M&A, and securities law. Through her work and digital platform (@sidebarwithbec), she demystifies the law, builds trust online, and bridges the gap between legal excellence and modern influence.
LILLY KELLY
COO
Lilly is a seasoned operations and project management professional with a strong background in healthcare administration, clinical research, and business strategy. She currently serves as Chief Operating Officer at Sidebar Consulting & Entertainment, where she oversees operations, strategy, and execution for a growing consulting and entertainment-focused business.
In parallel, Lilly has spent nearly four years as a Clinical Project Manager at Children’s Hospital of Philadelphia, leading complex clinical research initiatives and administrative operations in one of the nation’s top healthcare institutions. Her experience also includes leadership roles in healthcare systems, special project management, and long-term administrative operations.
Lilly holds an MBA in Finance with a postgraduate certificate in Healthcare Administration, along with a bachelor’s degree in Management and Marketing (cum laude). Known for her precision, operational discipline, and ability to scale systems, she brings structure, efficiency, and strategic clarity to every organization she supports.
Tommy is a Certified Public Accountant with over eight years of experience across public accounting and private industry, combining deep technical tax expertise with hands-on experience in tax technology and AI-driven software solutions. He holds a Master of Science in Taxation (MST) and a Master of Accountancy (MAcc), with a background spanning corporate, partnership, and individual taxation, as well as financial reporting and internal controls.
Passionate about tax transformation, Tommy focuses on integrating AI, automation, and cloud-based platforms into traditional accounting workflows to improve efficiency, accuracy, and insight. He has led and supported technology implementations and brings a proactive, analytical approach to helping organizations stay ahead of regulatory and technological change.