Category: The Accidental CFO

“Stories and lessons from an unexpected journey in finance.” I once sat in a steering committee where we approved a massive, seven-figure software migration. The slide deck was flawless. The ROI projections were green. Everyone around the table nodded in agreement. But the lead implementation engineer at the end of the table was staring at…

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“Stories and lessons from an unexpected journey in finance.” In my “Cupcake Shop” post last year, we established a weak gross margin is like frosting air. If every sale makes you hungrier instead of richer, it’s not growth—it’s a sugar high. Let’s go a layer deeper. If your unit economics are secretly upside down, hitting…

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“Stories and lessons from an unexpected journey in finance.” If you listen closely, you can hear it. It’s not the wind; it’s the collective sigh of thousands of finance professionals opening a PBC (Provided by Client) list that looks longer than a CVS receipt. Audit season is officially here. For many CFOs” the annual audit…

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“Stories and lessons from an unexpected journey in finance.” Being a CFO right now feels less like managing corporate strategy and more like playing dodgeball with software vendors. According to the 2026 “Gartner Finance Technology Bullseye Report”, 79% of us are feeling the pressure to transform traditional workflows. Let’s cut through the buzzwords and look at the…

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“Stories and lessons from an unexpected journey in finance.” I’ve negotiated deals worth hundreds of millions of dollars—M&A, financing rounds, complex vendor contracts. I’ve sat across from seasoned executives, investment bankers, and private equity partners. But some of the toughest negotiators I’ve ever faced? My kids. No playbook. No term sheet. No artificial deadlines. Just…

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