From Disappointed Employee to Founder: How Missing Out on Stock Options Sparked an Entrepreneurial Journey

An entrepreneur reflects on his fifteen-year path from joining early-stage internet companies in the dot-com boom era to founding his own business, motivated partly by repeated disappointment in missing out on wealth-creation opportunities despite being in the right place at the right time. After losing out on stock options and bonuses at his first two positions, he eventually left a lucrative corporate role at Rakuten to start his own company, which he later sold. The author attributes his entrepreneurial drive to a deep-rooted unwillingness to allow corporate structures to dictate the trajectory of his life and career.

The entrepreneur's journey began during the dot-com boom when he transitioned from pursuing photography to joining early-stage internet companies. At his first position, he anticipated wealth through stock options but received none, even after the company was acquired for millions. He subsequently held a vice president role at a merged entity under Rakuten, where he accumulated several million yen in stock options before abandoning them to pursue overseas education—an unprecedented request that management rejected.

Years later, after founding his own company at age 32, similar patterns emerged: promised pre-IPO shares from a merger partner were rescinded due to shareholder opposition, and a subsequent management buyout required him to repurchase equity at a premium. The company was ultimately sold a decade later, which he describes as coinciding with the timeline suggested in business literature for building substantial wealth.