Episode #207: Greg Wolfe - Imagine Financial

Self-Made Is A Myth - Make A Difference Together

Greg Wolfe serves as the CEO of Imagine Financial, a South Bend–based insurance and financial services agency founded and owned by his wife, Chelsey Wolfe. Together, they lead a team that helps employers strengthen their benefit programs while improving profitability and employee satisfaction. Before launching into entrepreneurship, Greg spent several years in the automotive industry, where he developed his passion for leadership, relationship-building, and helping people reach their potential. That experience inspired him to pursue a bigger vision — building a company that creates financial impact for both businesses and families. Under their leadership, Imagine Financial has grown to more than 25 licensed agents, producing over two million dollars in issued paid commissions and two million dollars in annuity rollovers last year. The agency focuses on helping employers enhance benefits, reduce payroll taxes, and increase financial wellness without changing existing coverage. Outside of business, Greg is active in the community through speaking, mentoring, and hosting The Kitchen Table Podcast, where he highlights local leaders and real stories of faith, family, and entrepreneurship. He and Chelsey are proud parents of four daughters — Karlie, Natalee, Niya, and Navy — who remain the heart behind everything they do.