ProcurementExpress.com Logo
Start Free Trial
ProcurementExpress.com Logo
Book a Demo
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
Loading
/
Download File
Play in new window
  • 28.52 min
  • 2025-09-01
Subscribe on

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

More Episodes

Merushka Chetty

Elliott Gaspar – UK’s Secret Weapon Against Silicon Valley

In this episode, James Kennedy sits down with Elliott Gaspar, UK-based Fractional CFO and founder of a fast-growing finance practice, to unpack how the UK’s unique tax-advantaged investment schemes (SEIS/EIS) can accelerate early-stage growth – and how easily founders can lose their eligibility without realizing it.

Drawing on a career that started in Oxford University finance, scaled through private-equity-backed energy infrastructure, and evolved into advising high-growth, asset-heavy startups, Elliott explains why CFOs must be storytellers, how to build investor-ready financial models, and why UK entrepreneurs still underestimate the power of compliance-driven incentives.

They also explore:
– Why the UK remains one of the world’s best places to raise capital
– How founders accidentally invalidate SEIS/EIS (and how to avoid it)
– When asset-heavy roll-ups can unlock better financing
– The role of the Fractional CFO community in raising standards

Listen Now »
Merushka Chetty

Chris Gwinn – CFO Adds $1M EBITDA Without Timesheets

In this episode, James Kennedy sits down with Chris Gwinn, CFA and founder of Midwest CFO, to unpack how a fractional CFO helped a $7.5M digital agency boost gross margins from 26% to 48% and add $1M in EBITDA – without forcing creatives into traditional timesheets. Chris shares why he exited a successful process-improvement consultancy to build a more recurring, finance-driven practice, how he uses podcasts as a growth engine, and the simple pricing and cost-allocation shifts any B2B services firm can use to increase valuation.

Listen Now »
Merushka Chetty

Carolina Aponte – Venezuelan Immigrant’s Rise to Top CFO Success

In this episode, James Kennedy sits down with Carolina Aponte – fractional CFO, founder, and co-host of the Breaking Even Better podcast – to trace her journey from teen tour guide in Venezuela to award-winning North Carolina business owner. Carolina shares how she arrived in the U.S. at 20 without a high school diploma, juggled three jobs to survive, and used night classes plus on-the-job learning to climb from receptionist to controller and ultimately firm owner.

They unpack what a great controller actually does, how finance leaders can influence (but not control!) CEOs, and why relationships, resilience, and “improv” are just as important as debits and credits. Carolina also talks about helping more than 10 clients break the $1M revenue barrier and how her team-based model delivers 90%+ client retention.

Listen Now »