Flexport's founder details his journey from a hands-off "manager mode" to a directive "founder mode." The rise of bottom-up AI innovation in hackathons is causing him to cycle back, recognizing the need to balance top-down strategy with empowering creative, decentralized ideas that leadership couldn't have conceived.
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Amplitude's CEO describes the painful transition from founder (running to the hardest problem) to large-company executive. The latter role requires embracing hierarchy, saying "no" to most things, and managing through leverage rather than direct contribution—a skill set many founders resist and fail to learn.
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Flexport's internal hackathons are now its primary source for AI-driven innovation. With 90% of projects using LLMs, these events generate real product features and influence the company's roadmap. This demonstrates a powerful bottom-up approach where the most valuable ideas come from engineers closest to the problems.