The Startup Podcast · 2026-06-08 · 43 min
Every founder gets a version of the same advice: don't pick a fight with an entrenched industry. The incumbents have the relationships, the regulatory cover, the deep pockets - you'll bleed out trying. But some of the most interesting companies of the last decade were built ignoring that advice, winning over markets that were nearly impenetrable. In this episode, Yaniv Bernstein is joined by Brandon Weber - co-founder and CEO of Nava Benefits, a Series C-funded AI-powered health benefits brokerage. Before Nava, Brandon co-founded Hightower, a commercial real estate startup that merged with VTS and went on to run over half of all office buildings in the United States. Brandon has now done this twice in two completely different industries, and has developed a repeatable playbook for breaking into entrenched markets and using AI as a structural advantage. Yaniv and Brandon dig into what actually makes a market 'broken', why the entry point needs to be far narrower than most founders think, and how to build the conviction to keep going when a thousand people tell you it won't work.
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