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Are you treating insurance as a fixed expense or a controllable outcome? In a market where premiums are rising and underwriters are becoming more selective, simply having "tech" isn't enough. On this episode of, I’m joined by Chris Loewenberg of Cottingham & Butler to dismantle the friction between carriers, brokers, and underwriters. Chris breaks down why the industry is currently trapped in a "misalignment cycle" and why your data is useless if it isn't changing your team's daily behavior. We’re moving past the paperwork and looking at the Psychology of Risk in 2026. In this episode, we dive deep into: The Three Perspectives of Frustration: Why carriers see price, brokers see a black hole, and underwriters see a guessing game—and how to align them to lower costs. The Data vs. Behavior Gap: Why dashboards and devices don’t lower premiums, but the actions they trigger do. The COI Trap: Why a Certificate of Insurance is only a "snapshot in time" and how relying on old paperwork stops freight and creates massive friction. The Highway to Automation: How modern insurance validation through platforms like Highway is replacing manual back-and-forth and keeping trucks moving. Underwriter Insights: What the "guessing game" looks like from the other side of the desk and how to give underwriters the confidence to say "Yes" to your risk. If you’re tired of insurance being a "black hole" in your P&L, this episode is your roadmap to becoming a truly insurable business.