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David Chong quit his $192,000-a-year job at Microsoft last year to launch an artificial intelligence startup.
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A few weeks later, most of his belongings were stolen while moving from New York City to Toronto.
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He shares how he worked to regain his energy and why he has no regrets about going all out to start a business.
The now-famous article was based on a conversation with David Chong, a 38-year-old startup founder in Toronto. He previously worked as a senior software engineer at Microsoft until he resigned last September. The following content has been edited for length and clarity.
I will resign from Microsoft in September 2025. Less than a month later, I lost almost everything I owned.
During my move from New York to my hometown of Toronto, the trailer transporting my belongings was stolen in the middle of the night. The trailer was eventually recovered, but none of my belongings were found.
While quitting Microsoft set me on this unfortunate path, I believe leaving a big tech company was the right move for me. I had to learn what Zen monks preached about giving up worldly possessions to gain enlightenment.
I worked my way up 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 an entry-level employee and working my way up to Principal Product Engineer.
When I joined Microsoft in 2022 as a Senior Software Engineer, it felt like a bit of a step backwards in terms of title. I thought it would be easy to get promoted to a higher level, but it wasn’t; I stayed in the same position for almost three years.
At my previous employer it felt like your job spoke for itself, but at Microsoft it felt like I had to develop a “promotion” skill – doing a lot of internal self-promotion to make sure my work was noticed outside of my immediate team – to actually advance.
I understand that the need to aggressively self-promote in order to advance is a broader trend at big tech companies. It doesn’t seem transferable outside of the big tech world, so I’m not very interested in developing it.
Business Insider speaks with employees who have found themselves at a crossroads at their companies—whether due to layoffs, resignations, job searches or changes in workplace expectations.
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I started thinking about quitting, even though it meant leaving the U.S.
During my last few years at Microsoft, the company went through several reorganizations, which moved me around to different teams. In the latest round, a number of our managers were let go.
The layoffs didn’t make me too worried about my job security, in part because there seemed to be a shortage of engineering talent in my department. However, I am becoming increasingly frustrated with the slow promotional schedule.
Expectations for company productivity and office work also appear to be rising. The message from leadership seems to be that we need to accelerate and adapt because times are changing.
Another thing that made me start thinking about leaving was that I wasn’t learning as much as I wanted to, partly because I had become the most senior person on the team.
In early 2025, I started seriously considering leaving Microsoft and thinking about my next career move. This is a very difficult decision. I was on a TN visa, which was specifically related to Microsoft, and quitting would have meant moving back to Toronto and committing to a future outside of the US, unless I could find another company willing to sponsor me. I came to the United States with the intention of living here long-term. Microsoft has started the green card process for me, and quitting means giving up the green card process.
Around April last year, a friend opened my eyes to the possibility of starting a business. 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 start a business.
In September, I resigned from Microsoft. I’m not too worried about giving up a $192,000 annual salary because I consider myself to be very risk-tolerant. I had saved enough of a buffer to be able to cope with no income for several years, and I didn’t have any dependents.
My belongings were stolen forcing me to postpone my plans
Losing items during the move would definitely hurt my productivity, forcing me to delay my launch plans by a few months.
Of all the stuff I owned, I only had the flight items in my backpack and carry-on bag. I landed in Toronto with no winter clothes and no bed – I had to sleep on the floor in a sleeping bag.
I focused on resolving the moving issue: trying to figure out what was going on, contacting the police, and dealing with the insurance claim. Unfortunately, my moving insurance rates were among the lowest, so the insurance payout was even less than what I paid for the moving services.
Of course, there are financial implications to replacing everything. So far, I’ve spent about $12,000 on necessities like a couch, bed, air fryer, instant pot, and clothes. Since everything was stolen, I started from scratch in more ways than one.
However, in recent months, my AI sales agency business, Falco, has made progress. It’s still under development and not yet ready for customers, but it’s publicly available.
When it comes to building a startup, I don’t think the idea is necessarily more important than the execution. My hope is that if I give it my all, move quickly, and keep testing my ideas, I should be fine. My plan was to give myself about three years to start a business. If all else fails, I’ll go back to the job market.
My advice to others considering a major career move
My advice is to try to put yourself in your shoes five to ten years from now. When I do this, I look back at the decisions I face and ask myself, “Would I regret not doing this?”
If the answer is yes, I try to do things that I will regret not doing. I often hear of older people regretting that they didn’t take more opportunities.
In hindsight, I think it was this mentality that helped me decide to move to New York and join Microsoft—both decisions had their pros and cons, but I don’t regret it. My first job in New York helped me gain experience at Microsoft, which gave me the opportunity to develop my skills and meet some very interesting people.
For me, leaving Microsoft to start a business is a decision that I think my future self will not regret, even if I fail, so I will go all out to start a business.
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