Dear Monday
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About
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 i...
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Recent episodes
- S2E10 Clarity Before Commitment: The Cost You Don’t Count
- S2E9 Clarity Before Commitment: How Do You Know When You’re Ready to Go Again?
- S2E8 Clarity Before Commitment: Do You Actually Want the Life, or Just the Decision?
- S2E7 Clarity Before Commitment: How Do You Know When You’ve Waited Too Long?
- S2E6 Clarity Before Commitment: What Are the Obligations Nobody Mentions?
- S2E5 Clarity Before Commitment: Where Do You Go When the Ground Shifts?
- S2E4 Clarity Before Commitment: What Are You Pretending Not to Know?
- S2E3 Clarity Before Commitment: What Does Your Yes Actually Commit You To?
- S2E2 Clarity Before Commitment: What Are You Waiting for Someone to Tell You?
- S2E1 Clarity Before Commitment: The Moment Before the Decision