Jason White, a 46-year-old former tech executive at Google and Meta, left his high-profile roles to launch an AI-driven financial startup called Bear Financial. His journey from corporate tech to entrepreneurship offers valuable insights for others considering a similar leap. White began his tech career at Google in 2016 as a tech lead on the Gmail team, later moving to Google Search in 2020. By 2024, he felt constrained by the pace and direction of innovation at Google, particularly in AI. He sought a role that would allow him to focus more deeply on artificial intelligence, leading him to accept an offer from Meta in August 2024. At Meta, he worked as an AI machine learning engineer, enjoying access to top-tier talent, robust resources, and meaningful projects. Yet by mid-2025, he began contemplating a major shift. He was drawn to the idea of building a startup that uses AI to help everyday households manage their finances—a mission inspired by his own past struggles as a low-income graduate student raising a newborn. The decision to leave Meta was not easy. He weighed the loss of a stable income, the comfort of a strong team, and the risk of legal complications, especially around non-compete clauses and disclosure requirements. He also considered the financial impact on his family. To prepare, he adjusted his budget, reduced 401(k) contributions, and built up liquid savings to cover at least a year of living expenses without touching retirement funds. His wife’s income provided additional security, and they maintained a balanced lifestyle, including vacations and household support. After months of reflection and conversations with a potential cofounder—a friend of a friend—he made the decision to resign in September 2025. His colleagues reacted with a mix of surprise, encouragement, and envy, highlighting the widespread desire among tech workers to start their own ventures, even if few can take the leap. Today, White is focused on building Bear Financial, a bootstrapped startup that aims to launch publicly later this year. While external funding may come in the future, he’s prioritizing control and financial discipline, tracking every expense closely. His advice to others considering the same path is clear: secure your finances first, ensure your family supports the move, choose a mission you’re deeply passionate about, and be prepared to wear many hats. He also recommends mentally preparing for failure—asking whether you’d still be satisfied if the venture didn’t succeed. For White, the experience itself would be worth it. Despite challenges like regulatory uncertainty, customer acquisition, and competition from well-funded firms, he remains committed to taking the risk. “I want to take the swing,” he says.