Resources

Keith has spent 30+ years in the trenches of business and financial management. These videos distill that experience into tools, frameworks, and real talk you can put to work immediately — no fluff, no theory for theory’s sake.

Browse by topic, or start at the top. Either way, you’ll walk away with something you can actually use.

  • Scale with Confidence Using Cowboy Math
    • 4/9/26

    Scale with Confidence Using Cowboy Math

    Growth without financial clarity is just controlled chaos. This video shows you how to scale on solid ground. Samantha Upkes explains how to overcome your growth barrier by boosting your team's confidence with Cowboy Math.

  • Creating Momentum Using Cowboy Math
    • 4/10/26

    Creating Momentum Using Cowboy Math

    Understand where your cash is actually going — and how to get ahead of it before it becomes a problem. Watch this video with Coach Keith if you want more predictable cash flow.

  • Cowboy Math = Team Confidence
    • 4/11/26

    Cowboy Math = Team Confidence

    When your team understands the numbers, they make better decisions. Here’s how to bring that clarity to the whole organization. Watch this video with Coach Keith to learn how to connect your short- and long-term goals to build team confidence.

  • Increase Predictability Using Cowboy Math
    • 4/12/26

    Increase Predictability Using Cowboy Math

    Stop guessing. Start forecasting with real confidence. Watch this video of Samantha Upkes to learn how to gain predictability by connecting your long-term and short-term goals.

  • Cowboy Math

    Cowboy Math

    Simple, practical, and built for leaders who think in outcomes — not spreadsheets. This is the financial clarity framework at the core of Keith’s work with scaling companies. Coach Keith explains how "Cowboy Math" can completely transform your business.

  • Cowboy Math = Cash Flow
    • 4/21/26

    Cowboy Math = Cash Flow

    Understand where your cash is actually going — and how to get ahead of it before it becomes a problem. Watch this video with Coach Keith if you want more predictable cash flow.