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This business research case introduces Cogent Labs, a Japanese high-tech start-up that provides AI-driven technologies, is making the critical transition from an entrepreneur-driven to a mature management-run organization, the company’s business context and technology development. That requires to harmonize the entrepreneurial and managerial capacity, by a collaborative approach integrating cross-functional product teams. The high-tech start-up has demonstrated ability to overcome the transitional stage of the first entrepreneurship to stability and sustainability through the management, while at the same time keeping innovation by adding Natural Language Processing and Times-Series developments, and creativity; rapidly developing new products. The business case demonstrates that in the start-up to managerial transition of a high-tech start-up the key success factor lies in the motivation and coordination of the different professional cultures –scientific and engineering- that should collaborate in the AI research and fast development of viable products. The method is based on interviews conducted with key executives and a strategic analysis of the firm and its rapidly evolving context in terms of artificial intelligence (AI) and deep learning. The start-up company develops AI-based applications like Tegaki AI, supporting their initial clients from the financial sector in the incremental automation of business processes, based on AI- and Internet of Things (IoT)-driven business processes. Tegaki AI triggers non-strategic business decisions through optical character recognition (OCR) and optical handwriting recognition (OHR) algorithms that show 99.2% accuracy. This business case describes the context of entrepreneurship ecosystems in Japan and the economic emergence of business smartization solutions through the new AI paradigm and OHR.