Understanding My Identity as a Creator, Entrepreneur, and Investor

Also available on Medium.

For my mother, the iron woman:
In your triumphant, battered hymn, I now sing the song of history.

Miami Tech House

The first business I started was with Airbnb in Miami, FL in the fall of 2015. I was a 22 year old fresh college graduate, starting my first job in a startup. At the time, I had been gainfully employed as a software engineer for all of six weeks when my employer started missing payroll. In a panic, I called my mother and conspired an emergency plan: I would rent out my bedroom in Miami (rent basis: $873/mth) and work remotely from her house in Boston. Counter to stereotypes, my mother had been a far earlier adopter of Airbnb than her millennial son: by 2015, she had already been hosting travelers for a couple years. At that time, I had joked that my mother avoided ‘empty nest syndrome’ by monetizing my sister’s and my old bedrooms. In addition, while I grew up in a secure upbringing, our family’s economic mindset was also quite modest: 不要浪费, ‘never waste’, was the driving ethos that ran through our lives. As a result, since my employer wasn’t paying me, there would be no basis to deny my request to work remotely, especially to keep working for free, right?

Six months later, the company finally laid me off. At the time, I took it very personally, not knowing that the core business model of the company was the issue and years later its angel investors would sue the founder in a very public falling out. What I did know, at the time, was this: following the footsteps of my mother in generating side income via Airbnb gave me an enormous sense of control over my finances. I now had greater context why, despite my mother’s steady career as a public school teacher, she was working on entrepreneurial endeavors on the side to make more cash. Running a boring business like Airbnb had made money—money that

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