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David Chong quit his $192,000-a-year Microsoft job last year to build an AI startup.
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Weeks later, most of his possessions were stolen during his move from New York City to Toronto.
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He shared how he’s trying to bounce back — and why he doesn’t regret going all-in on entrepreneurship.
This essay, as stated, is based on a conversation with David Chong, a 38-year-old startup founder from Toronto. He previously worked as a senior software engineer at Microsoft until he resigned last September. The following has been edited for length and clarity.
I resigned from Microsoft in September 2025. Less than a month later, I lost almost everything I had.
During my move from New York City to my hometown of Toronto, the trailer carrying my belongings was stolen in the middle of the night. The trailer was eventually recovered, but none of my belongings were.
While resigning from Microsoft set me on this unfortunate path, I believe that leaving Big Tech was the right move for me. I had to learn what the Zen monks preach about giving up your worldly possessions to reach enlightenment.
I struggled to get promoted at Microsoft
In 2016, I moved from Canada to New York City on a work visa. Before joining Microsoft, I worked at a smaller technology company for nearly seven years, starting as a junior employee and working my way up to a leadership role as a Principal Product Engineer.
When I joined Microsoft as a senior software engineer in 2022, it felt like a bit of a throwback to the title. I thought it would be easy to get promoted back to a higher level, but it certainly wasn’t; I held the same position for almost three years.
At my former employer, I felt like your work spoke for itself, but at Microsoft, I felt I needed to develop a skill to “get promoted”—do a lot of internal self-promotion to make sure my work was noticed outside of my immediate team—to actually get through.
From what I’ve heard, the need to actively promote yourself to get ahead is a broader trend in Big Tech. It seemed pretty non-transferable outside of the Big Tech world, so I wasn’t really interested in developing it.
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I started thinking about giving up, even if it meant leaving the US
During my last years at Microsoft, the company went through several restructurings that moved me to different teams. In the most recent round, some of our managers were made redundant.
The layoffs didn’t make me too concerned about my job security, in part because my department seemed starved for engineering talent. However, I was becoming increasingly frustrated with the slow promotion timeline.
There also seemed to be increasing expectations at the company regarding productivity and office work. The message from management seemed to be that we needed to step up and adapt because times were changing.
The other thing that made me consider leaving was that I wasn’t learning as much as I wanted, partly because I had become the tallest person on my team.
In early 2025, I began to seriously consider leaving Microsoft and figuring out my next career move. It was a very difficult decision. I was working on a TN visa that was specifically tied to Microsoft, and resigning would likely mean returning to Toronto and committing to a future outside the US unless I could find another company willing to sponsor me. I would have come to the US thinking of living here long term. Microsoft has already started the green card process for me and opting out would mean opting out of that too.
Last April, a friend opened my eyes to the possibility of entrepreneurship. I became more interested in this path and started doing a lot of research on how to build a business. I decided that if I left Microsoft, I would pursue entrepreneurship.
In September, I resigned from Microsoft. I wasn’t too worried about giving up my $192,000 a year salary because I consider myself very risk tolerant. I have saved enough to go without income for several years and have no dependents.
The theft of the goods forced me to postpone my plans
Losing my belongings during the move definitely affected my productivity, forcing me to postpone my startup plans for several months.
Of everything I had, all I had left was what I packed for the flight in my backpack and handbag. I landed in Toronto without winter clothes or a bed — I had to sleep on the floor in a sleeping bag.
I focused on solving the problems of the move: trying to find out what happened, contacting the police, and solving the insurance claim. Unfortunately, I received the lowest insurance rate for my move, so the insurance payment was less than what I paid for the moving service.
And of course there was the financial impact of replacing it all. So far, I’ve spent about $12,000 on essentials like a couch, bed, deep fryer, Instant Pot, and clothing. Since everything was stolen, I’m starting from scratch in more ways than one.
However, over the past few months, I’ve been making progress with my AI sales agent business, Falco. It is still in development and not yet ready for customers, but it has been released publicly.
When it comes to building a startup, I don’t think the idea necessarily matters as much as the execution. I’m hoping that if I go all-in, move fast, and constantly test my ideas, I should be OK. My plan is to give myself about three years to pursue entrepreneurship. If all else fails, I will return to the workforce.
My advice to others weighing a big career move
My advice is to try to put yourself in your shoes five to 10 years from now. When I do this, I look back at the decision I’m facing and ask myself, “Would I regret not doing this?”
If the answer is yes, I try to do the thing I wish I hadn’t done. I’ve often heard that older people regret the chances they didn’t take more than the ones they did.
In retrospect, I think this mindset helped me move to New York and join Microsoft—two decisions that had their pros and cons, but which I don’t regret. My first job in New York helped me build the experience that brought me to Microsoft, and Microsoft gave me the opportunity to develop my skills and meet very interesting people.
For me, leaving Microsoft to start a business is a decision I don’t think my future self will regret, even if I don’t succeed, so I’m going all-in on entrepreneurship.
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