Dear Monday

Dear Monday is a podcast about the decisions that change the shape of your life. Most people talk about opportunity in terms of upside — growth, freedom, financial potential. But far fewer conversations sit with what lives underneath those decisions: the obligations, the constraints, the commitments that are difficult to unwind once they're made. This show exists in that space. Each episode explores the realities behind ownership — business ownership, franchise investment, career exits, and other high-stakes commitments that reshape financial and personal life. I spent years inside franchise ownership and deal advisory — walking prospective owners through the discovery process and watching how the industry was designed to move people toward decisions, not through them. Dear Monday is what I built for the moment in between. The conversations are reflective, structured, and grounded in one principle: Clarity before commitment. Rather than motiva