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Month 2 introspection


It's been 2 months since I left Airbnb! It's been a roller coaster since. Jan 4th, 2021 was my last day – it was emotional but celebratory. A new dawn was rising. Jan 5th, 2021 was the first day of YC. Every Tuesday, YC brings special YC alums to talk about their journey, their company and any advice they have to pass to fellow YC founders. The first – to kick off the batch – was none other than the... Airbnb founders! I couldn't escape, but it was nice to see familiar faces! It was special hearing their story as a fellow YC founder – I had heard their story many times as an employee and to the media, but never as a fellow founder.

Anyways, this post is not about that but about introspection. Every month, I will write an introspection post about how I've been as a cofounder, and sharing my learnings over the past 4 weeks.

Focus on large problems

I did already rewrote our API. That was smart but a mistake. We were once a Rails shop, now we are on Nodejs. My experience with JS has been primarily on the frontend, and I haven't built out a large Nodejs backend before (primarily because I didn't feel like there is an ORM that is as good as ActiveRecord. This is still true). Building v0.1 of Shepherd was done in 1.5 weeks. Rewriting was 1.5 weeks. Getting to a stage where I was being productive on the backend is still WIP. I do think this is the right long-term decision, and I do think hiring someone who's proficient in JS will pay dividends on the backend and frontend, but I definitely paid a cost early on.

This has ultimately distracted me from the large problems that needed to be solved, forcing me to spend time on tasks I had already built experience to solve with Rails. For example, I had done error logging with Sentry many times over with Rails, and hardly miss errors. With Nodejs on the backend, we have had many errors go unnoticed, and it still feels like whack-a-mole.

Appreciate your cofounder

Reality is, you spend most of your waking day with your co-workers. But at the end of the day, you say goodbye and your day is done with them. This is not the case with cofounders; we are constantly on. As they say, happy wife happy life and this couldn't be more true with cofounders. Appreciate your cofounders. It goes a really long way.

Justin and I now schedule walking time every week. It's a chance for us to get to know each other more, learn about what worries the other, what's been on their chest, what they're excited about. It's a time for us to connect, build empathy and appreciate each other. It's a running joke that we learnt from YC's parenting breakout session but it carries truth – we remind each other that we value each other.


I wanted to start writing more as a way to share my learnings, and experiences. Heck, I even decided to write quick bite-sized tech posts that solve a specific problem I literally was just searching to fix. For example, I ran into a problem with authentication with Nextjs. I wrote a post about that. It's not only good to share your knowledge but could pay dividends by being noticed, for recruiting or folks carrying interest in what you're doing.

I do admit my writing is not in the best tip-top shape but I intend to write often, and write about problems I am experiencing as I go through this journey.

People want to help nice people doing interesting things

Over the past 2-3 months, I've met folks that I've looked up to for many years since I moved to SF. Investors, entrepreneurs, leaders and more – they've given us time in their day because we are trying to carry a nice demeanor and doing something interesting. These opportunities would have never been afforded to me previously (I love Airbnb, and I am incredibly thankful for the opportunity to work there, to have it on my resume and to share my story).

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