2018 in Retrospect, Part 1: Leaving Coursera and starting a new journey

April 15, 2019

Photo by Randy Jacob
/ Unsplash
Photo by Randy Jacob / Unsplash

I missed reflecting on my year when the clock struck 12:00 on the first day of 2019 because I was still in the middle of life’s most important lesson – but now that I’m done and have time to reflect, I wanted to write down my reflections.

Leaving Coursera

This was hard. I was at Coursera for a total of 4 years, 1 month, and 7 days. During this time, I worked on Monetization, Growth, Learning Experience, and Infrastructure and did some of my best work. Leaving was a tough choice, but after my personal growth slowed, I decided it was time to do other things.

When I left Coursera, I wanted to work on was personal. I had just finished reaching Atul Gawande’s Being Mortal and really wanted to spend more time thinking about family and loved ones. I don’t know if it was my upbringing, my privilege, or my ignorance, but before reading Being Mortal, I did not understand what it felt like to have a sense of duty towards my parents and towards my grandparents.

I suddenly felt the urge to spend more time with the significant people in my life: my parents were in Los Angeles and my significant other was in Minneapolis. I was in San Francisco and felt like I wasn’t nearly spending enough quality time with them.

It started small

After leaving from Coursera, while I was creating trip plans and trying to figure out how to better connect with friends and family, something somewhat unexpected happend. One of my good friends was telling me about her startup idea. She wanted to get some feedback, and was was hoping I could consult on technical work. Neither she nor her current business partner had as much technical experience.

Even though I wanted to spend time with family, I imagined I was going to have some down time where I could put my technical abilities to use. After all, my parents are not yet retired and my girlfriend has travel projects. I figured contributing a bit on the techncal end could satisfy my intellectual needs and help a friend at the same time.

I volunteered to chip in time to help build software as long as I could continue to pursue spending time with family and loved ones.

A dream came knocking on the door

I attribute YCombinator to igniting my interest in computer science back in 2009. When I was trying to decide what I wanted to do, I had no idea the impact software could have on the world. Reading Hacker News exposed me to the hacker culture that would create Dropbox, AirBnb, etc.

The company I had started writing code for was ShopWith. We wanted to disrupt the online shopping journey – from product discovery, all the way to the product being in the hands of the consumer. There was (and still is) a huge opportunity to build a shopping platform that the world had never yet seen. Amazon wasn’t it. Instagram wasn’t it.

When I got involved, the first thing that we did was apply for YCombinator’s Summer 2018 batch. It was a long shot, but it sounded like it was worth trying. At worst, it was a forcing function for us to figure out the finer details of our business. At best, we would get an opportunity that we couldn’t even begin to imagine.

So we applied. We didn’t expect to get in.

A couple days later, we were told to go in for an interview. We were ecstatic.

We went in for the interview. We walked out of that interview patting ourselves on the back – it was a great experience. We didn’t expect to get in.

That night, around 8PM, we got the call … and we were accepted into the Summer 2018 batch!

We were on cloud nine.

For dinner that night, we went to Okane across the street from Zynga and treated ourselves to a nice meal. All of us liked Japanese food, and we thought we deserved being fancy together this one time.

The inside of Okane, an izakaya on Townsend Street in San Francisco.
The inside of Okane, an izakaya on Townsend Street in San Frnacisco.

Each of us got a bite of o-toro (fatty tuna) and a bite of A5 wagyu. The bill for the three of us was well over $100. Life was amazing. We were amazing. In three weeks, we went from a new rag tag team, to a team that seriously thought we could take on the world.


That night I knew had to sort out my priorities. Going through YC that summer an unexpected variable that I now had to account for. The stakes on my involvement in this company suddenly jumped tenfold, if not more.

Demo Day was roughly 4 months away. I had to give all my time, energy, and effort into the next 4 months to ensure that we had a huge demo day.

I called Alice (my significant other) first. Then I called my parents. I let them know that we got into this startup incubator and that I was going to give it my all. Underlying the excitement and optimism was a slight tinge of disappointment because pursuing this was going to put a huge wrench in my original plans. This was a rare opportunity, and I was going to get as much out of it as I put into it. I told myself it was worth spending the next 120 days giving this company my all. I cancelled my flights to visit my parents. I cancelled my plans to visit Alice during the next four months.

They told me to go for it. They’d understand, I told myself.

This is part of a series of posts where I recount my last year’s startup experience.

Written by Lewis Chung. Founder @ ShopWith. Previously: Coursera, Amazon. Writes about technology, products, and life.