David Chong, 38, had most of his belongings stolen during his move from New York City to Toronto after quitting his Microsoft job.
David Chong made a bold career move that many would consider risky: he left his $192,000-a-year senior software engineer position at Microsoft to build an AI startup. Weeks later, during his move from New York City to his hometown of Toronto, a trailer transporting all his belongings was stolen in the middle of the night. While the trailer was eventually recovered, none of his possessions were.
Despite this devastating setback, Chong doesn't regret his decision to pursue entrepreneurship. "I've had to learn what the Zen monks preach about letting go of your earthly possessions to reach enlightenment," he shared.
The Struggle for Promotion at Microsoft
Chong joined Microsoft in 2022 after nearly seven years at a smaller tech company where he had worked his way up to a leadership role. At Microsoft, he found himself stuck in the same senior software engineer position for nearly three years.
"At my previous employer, it felt like your work spoke for itself, but at Microsoft, it felt like I would have to develop a 'getting promoted' skill," Chong explained. This involved significant internal self-promotion to ensure his work got noticed beyond his immediate team—a trend he observed across Big Tech companies.
Considering a Career Change
Multiple restructurings at Microsoft moved Chong to different teams, and he witnessed managers being laid off. While he wasn't overly concerned about job security, he grew frustrated with the slow promotion timeline and rising expectations around productivity and office attendance.
"I wasn't learning as much as I wanted to, partially because I had become the most senior person on my team," he noted.
The decision to leave was complicated by immigration considerations. Chong was on a TN visa tied specifically to Microsoft, and resigning meant likely moving back to Toronto and giving up the green card process Microsoft had started for him.
The Entrepreneurial Leap
In early 2025, a friend introduced Chong to the possibility of entrepreneurship. After extensive research, he decided this was his path forward. In September 2025, he resigned from Microsoft, relying on his risk tolerance and substantial savings to support himself without income for several years.
Rebuilding After Theft
The theft of his belongings forced Chong to delay his startup plans by several months. He arrived in Toronto with only what he carried on the flight, sleeping on the floor in a sleeping bag without winter clothes.
He spent approximately $12,000 replacing essentials like furniture, kitchen appliances, and clothing. The insurance payout was minimal since he had opted for the lowest coverage rate.
Despite these challenges, Chong has made progress with his AI sales agent business, Falco, which has launched publicly though it's still in development.
Advice for Career Transitions
Chong's approach to major decisions involves projecting himself five to ten years into the future. "I look back at the decision I'm facing and ask myself, 'Would I regret not doing this?'" he explained.
This mindset guided his move to New York, his decision to join Microsoft, and now his leap into entrepreneurship. "For me, leaving Microsoft to start a business is a decision I don't think my future self will regret, even if I fail," he said.
He plans to give himself about three years to pursue entrepreneurship before potentially returning to the job market if necessary.
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