2018 in Retrospect, Part 2: Lessons learned

May 29, 2019

To not leave anything for surprise, I wanted to start this post off by announcing: I’ve left ShopWith.

Unfortunately my journey got cut very short :) I’m still reflecting on a lot of what happened. It’s been over a month since I’ve left and I feel like I can finally start to talk about this with people.

Here are some notes — mostly for myself, but I’m hoping other people who discover this list find it useful.

  • Early on, all I saw in my co-founders was how similar their thoughts on the business were to mine. When I left, all I could see were our differences.
  • For us, we were aligned on the 10 year vision 100% of the time — but we constantly struggled with the now - 1 year time frame. Maybe a combination of poor communication or oversized egos or both.
  • People show that they care differently. An incompatibility in this that is not addressed upfront can manifest in terrible ways.
  • WRT Hanlon’s Razor: “Never attribute to malice that which is adequately explained by stupidity.” We’re all stupid in some way. Anyone who says they aren’t is insecure about something. Maybe worth addressing in a safe space.
  • Survivorship Bias kills. Working once is a good sign but not enough. Especially true if it’s not worked once or more.
  • Narcissists can be great if they are given the right role and support but can also be ticking time bombs. Beware.
  • In a team of N > 2, conversations about things other than the work itself that exclude people within that team can breed distrust. Especially when the team is struggling.
  • Therapy is never a bad thing. I do believe most people in the entrepreneurship community already understand it’s importance.
  • Most team problems start out as unaddressed individual problems. Most people have individual problems that they are naturally uncomfortable to bring up, even with their closest friends and relatives.
  • Similar religious, cultural, etc. backgrounds are not reliable signs of compatibility. Stress will find a way to surface incompatibilities in mysterious ways. Working them out as soon as possible is a good practice. It will never go away unless it’s actively confronted by the parties involved.

Some people who I’ve talked to in the past week have been curious about whether or not I thought doing a startup was worth it, despite all of the negatives. 100% yes, never had a better learning experience in my life. I’d definitely do it again.


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