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September 1, 2025

Kevin O’Brien – The Red Flags Every CEO Ignores Until It’s Too Late

James Kennedy sits down with Kevin O’Brien, CPA, CFA and founder of Gray Feather CFO, to unpack how he led a $2M EBITDA swing in a single year for a $10M+ distributor – moving from  – $500K to +$1.5M. They dig into when EBITDA is useful (and when it’s “BS,” per Charlie Munger), the nuts and bolts of KPI-driven turnarounds, and why a fast, five-day month-end close is non-negotiable.
The Gross Profit Podcast
The Gross Profit Podcast
Kevin O'Brien - The Red Flags Every CEO Ignores Until It's Too Late
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  • 28.52 min
  • 2025-09-01
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Show Notes

James Kennedy sits down with Kevin O’Brien, CPA, CFA and founder of Gray Feather CFO, to unpack how he led a $2M EBITDA swing in a single year for a $10M+ distributor – moving from –$500K to +$1.5M. They dig into when EBITDA is useful (and when it’s “BS,” per Charlie Munger), the nuts and bolts of KPI-driven turnarounds, and why a fast, five-day month-end close is non-negotiable.

About Kevin O’Brien

A former auditor turned controller, treasury manager, and FP&A leader, Kevin blends full-stack finance experience with rigorous investment training as a CFA charterholder. Through Gray Feather CFO, he helps owners get timely, decision-ready numbers, build accountability with KPI scorecards, and drive cash-backed profitability.

  • Website: grayfeathercfo.com
  • Focus: SMB finance transformation, KPI dashboards, cash forecasting, bank relationships/treasury, budgeting

What You’ll Learn

  • The $2M Turnaround Playbook: How historical profitability analysis + KPI targets + owner buy-in flipped results from –$500K to +$1.5M EBITDA.
  • EBITDA, Explained (and Debated): What gets added back – and why it can mislead in capital-intensive businesses.
  • Close in Five Days: Red flags in your finance function (20-day closes, mismatched COGS, “push” vs “pull” reporting) and how to fix them.
  • KPIs That Matter in Distribution: Gross margin (and its parts), material cost %, production labor %, and freight leverage.
  • Purchasing as Profit Center: RFP discipline, switching/negotiating suppliers, and bringing in freight brokers to claw back points of margin.
  • Treasury 101 for SMBs: Managing bank relationships, lines of credit, and cash forecasts so renewals aren’t “held for ransom.”

Episode Highlights

  • “If your close takes 20 days, you’re flying blind. By the time you get the numbers, they’re already out of date.”
  • “Gross margin is the signal – then break it down. Material costs up 10 points on $10M revenue is a $1M problem to solve.”
  • “EBITDA is useful but incomplete. In capital-heavy businesses, adding back big depreciation can turn fiction into finance.”
  • “Dashboards drive accountability. Put budget targets beside actuals every month and force the conversation.”
  • “The turnaround was compounding. Pricing discipline, purchasing leadership, and freight optimization added up to +$2M.”

More About Kevin’s Role

At Gray Feather CFO, Kevin installs a finance rhythm owners can trust: five-day closes, KPI scorecards tied to the budget, weekly cash forecasts, and lender-ready packages. He partners with leaders to upgrade talent (e.g., purchasing), run competitive RFPs, and lock in margin wins that show up in cash.

This podcast is tagged under:

The Gross Profit Podcast

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