• The Last Minute Landmine

    I spoke with a CEO last week. Thirty days before her renewal. Staring at a 38% increase. Her broker had the number for 60 days before she did. Sixty days. Sat on it. To be fair — they…

    Read Post

  • The Clearest Cultural Signal You Can send

    And most CEOs are sending the wrong one — without even knowing it. You can hang your values on the wall. You can run all-hands meetings about culture. You can write a beautiful mission statement and put it…

    Read Post

  • Stupid Things We Have To Invent

    This won’t shock anyone reading this blog, but nonsense is a real obstacle when you’re trying to run a common sense health plan. One of the first things I did when we went self-funded was call our PBM…

    Read Post

  • Intervene or Overpay

    Intervene or Overpay

    Real-Time Intervention: The Seconds That Save Thousands Most health plans measure success in annual renewals. Self-Funded CEOs measure it in minutes. The moment of highest leverage isn’t the annual renewal. It’s the 60 seconds before a member ends…

    Read Post

  • Coverage Stack Overflow

    Coverage Stack Overflow

    Three weeks in and here’s the uncomfortable truth: We have no idea what’s actually broken. We can see claims. We can see what processed. We can see what got paid. You know what we can’t see? Everything that failed before…

    Read Post

  • Good Idea + Bad System

    Good Idea + Bad System

    We went live with our self-funded plan on January 1st. Week one, we hit our first wall. And honestly? It’s the perfect example of why the traditional benefits system is broken. What We Asked For We want to…

    Read Post

  • My 2026 New Year’s Resolution

    Run My Health Plan Like a Product (And make it easy for you to steal our playbook) Most CEOs make personal New Year’s resolutions. I’m making an operational one. In 2026, I’m running my health plan like we…

    Read Post

  • Real-Time Visibility

    Real-Time Visibility

    Most CFOs can pull up their P&L in 30 seconds. Revenue, burn rate, runway, cash position — all real-time. But ask them about their health plan? “We’ll know in a few months when the renewal comes.” We think…

    Read Post

  • Day ZERO – “The -5 NPS”

    Most CEOs decide to change their health plan after looking at the renewal. I decided after looking at our employees (in addition to the renewal and our 24% increase). After we committed to going self-funded on January 1st,…

    Read Post

  • Rebuild vs Renew

    Rebuild vs Renew

    Most CEOs wouldn’t post this publicly, but here we go: Instead of pretending this makes sense, we’re doing something rational: ZERO is going self-funded on 1/1/26. We are going to run our health plan like the business it…

    Read Post