Large Company vs Startup & Door #3
January 10th, 2021
I recently made the decision to leave my job as a software engineer at Airbnb to join Explo full-time as a founding engineer. I thought it could be helpful to share how I went about making the decision, the different considerations I made, and what I learned from the process.
Background
When I was first approached about the opening for a founding engineer at Explo, I almost rejected the opportunity immediately. This is because I was (and still am) working on building momo outside of my day job, which appeared to me as a conflict of interest. How could I possibly take on this position at an early stage company while simultaneously building another company on the side? It wasn't that I didn't want to attempt both, but I figured that naturally they'd be at odds with each other (and assumed the Explo's founders wouldn't want me working on both projects at once). After all, there's onboarding, the standard 1-year vesting cliff, and the hectic nature of working at an early stage startup - which can be a lot to focus on without building anything else on the side.
Even though I was resolved that this almost certainly could not work, I couldn't seem to immediately say no. It did seem like a great opportunity, and I was afraid to close the door. I spoke with my dad about my dilemma, and his advice changed my outlook.
Door #3
I have a habit of viewing things as black and white once I understand the premise of a decision. So, when this Explo opportunity came around, I viewed myself as having 2 "doors" to choose from:
1. Say no to Explo, stay at Airbnb, and continue to work on momo on the side
2. Say yes to Explo, leave my job at Airbnb, and quit working on momo
My dad explained that there's actually a third option, Door #3, which is to gather more information before making a decision. When I analyzed my decision-making process, much of it was based on assumptions. I assumed that Explo wouldn't want me working on momo, and even if they did, I assumed that the precarity of momo taking off would leave too much up in the air for me to provide a solid long-term commitment (even deeper, I assumed that a relatively long-term commitment to Explo was necessary for this to work). I decided to discuss my situation with the founders instead of stick with these assumptions. I'm glad I did - turns out all of my assumptions were unfounded.
Established Company vs Startup
Once I spoke with the founders and discovered that my assumptions regarding Explo/momo were untrue, I began to think about whether pursuing this opportunity was the right choice. The big question in my mind was: Which opportunity will allow me to grow the most? In my mind, growth as an engineer has two dimensions:
1. Vertical growth (i.e. going deep)
2. Horizontal growth (i.e. going broad)
I asked a few mentors for guidance prior to making a decision, and one point resounded: Larger companies are better for vertical growth, and startups are better for horizontal growth. This made sense to me. On the whole, I think this point tends to be true. But by talking through my own circumstance, something else became clear: I was focused on the idea of a large company vs startup instead of my personal circumstance. I switched from "Large company vs Startup" to "Airbnb vs Explo". I wasn't comparing the two companies, but rather comparing the opportunities I had at each company. When I began thinking this way, I was able to reach a decision fairly quickly.
Conclusion
I learned a lot from this experience and hope to utilize these learnings when making decisions in the future. Combining these principles with the Regret Minimization Framework provides a solid foundation for making good choices.
If you found this post interesting, have any questions, or just want to chat, feel free to shoot me an email at apiel51@gmail.com (I respond to all personal emails :-) )