Retro on my first founding attempt

In January 2024, I quit my job at Abnormal Security and co-founded a startup as CTO.  Having worked on it for a year, I left the company in Jan 2025.  In this post, I’m not going to mention names and specifics, given that as of writing, the company and the product still exist, being operated by one of the cofounders.  (Obviously those who are curious can easily trace to the specifics.)

Between having a question mark on my resilience when things get hard and admitting the sunk cost in favor of moving on to better opportunities, given my judgement on the trajectory of the company, I chose the latter.  This decision made a deep cut in my identity and created some emotional turmoil, which even had collateral damage on my family, but I’ll focus on the more factual and technical aspects in this retro, leaving the emotional aspects for the future with more time for reflection.

While there are numerous details that could be mentioned, I’m going to focus on the highest level.  Because, let’s say we need to go from A to B separated by long distance, the high-level choices determine whether you walk, drive a car, or fly an airplane, whereas the small details are just optimizations like whether you are driving a Toyota or Ferrari.

Background

• I met the other 2 cofounders through a VC program that tries to capture pre-idea, pre-cofounder opportunities.  One of them was PM and she took the CEO role, I took CTO, and the other one was a UI/UX designer and was responsible for design and user study.  We are all in different cities and weren’t willing to relocate for this project, so we’ve been fully remote for the whole time.
• The problem we tried to solve was web browser tab overload as well as the deeper needs behind the symptom.
• We created an AI assistant as a Chrome extension that helps users to stay organized with their tabs. 
• By Feb 2025, we’d gotten 10k downloads on Chrome Web Store, ~40% of which came from paid ads over >10 months, ~50% came from 1 month of being highlighted in the home page of Chrome Web Store, and the rest ~10% from various other channels.
• We adopted a freemium and subscription model with some naively packaged paid features.  It resulted in some okay but not great free-to-paid conversion rate.
• Cash burn was primarily spent on salaries, and secondly on Meta ads.  The tech infrastructure costs pretty little even including the LLM cost, which could be paid by the minimum revenue generated.
• We had the long-term plan to become a cross-platform and cross-app organization tool.  Think organizing browser tabs from Chrome on your laptop and Safari on your iPhone, and think a folder where you can visually organize files, calendar events, messages, and web pages related to a specific project or topic.  Even better, most of the grunt organization work is done automatically by AI.

What went well

• I’d been wanting to start something for a few years and had been intentionally preparing for it, e.g. going to conferences and joining communities that attract startup people.  I connected with the guy who introduced me to the VC program by talking to another random guy at a Web3 conference.
• Working on a consumer product is super fun.  Your user is your buyer (as opposed to the decision-maker in B2B SaaS).  The feedback loop is super fast; I can fix a bug for some user while having a call with them, and I can get feedback on a new feature as soon as it’s shipped.  No matter what you do, there will be users who sing praises and who curse at you – it’s interesting to read the feedback and to strategize whether and how to respond.
• I was able to develop and operate the entire tech stack (shown below) with some help from a junior full-stack engineer, as I wasn’t very familiar with frontend development back then.  At the end, I became pretty fluent with the frontend part as well.  I was pretty proud that there was no incident during my 3-week trip back to China, and the product seems to be running okay without me now that I’ve left the company for a month.

• Besides the frontend development, it was also rewarding to be able to have hands-on experience on some stuff that I’d only had some superficial understanding of. Some of these experiences were actually helpful in my recent job search interviews.
  • Operate a Postgres instance with RDS: scale up instance type and storage, create a multi-az failover instance for near-zero downtime upgrades, deal with metrics like IOPS/EBSIOBalance/EBSByteBalance, create read-replica, snapshot, backup, snapshot exports for analytics, etc., etc.
  • Integrate and use a full-fledged product engineering platform including feature flag, A/B tests, product analytics, session recordings, etc.  We primarily used Posthog, which has all of the features and saved me a ton of time.
  • Set up an observability stack with self-managed Prometheus and Grafana, plus CloudWatch and PagerDuty.
  • Payment and CRM integration with Stripe and HubSpot for things like product marketing emails, influencer referral program, and of course, self-service subscription management.  These work areas are not intellectually difficult but very detail-oriented.  The hard thing is to remember how things are set up and not mess them up in future changes.
  • Growth oriented product features like sharing, link unfurling, etc.

What didn’t go well

• Overall, in the hindsight, the decision to jump into this project was reckless. It was a lollapalooza effect of multiple psychological biases. For example, the preparation I’d been doing created an inconsistancy avoidance bias. There were mere-association bias related to the background of my cofounders and the origin of the project (from a CMU lab). Not to mention the social proof bias from all the startup related social media posts.
• Not having a previous relationship with the cofounders themselves is already a big risk.  That plus being fully remote is almost guaranteed to fail.  You can even argue that the fact we didn’t want to relocate for the company was a sign of a lack of commitment.  Next time around, I’d spend more time pressure testing the cofounders no matter how good they look on paper or unless I’ve personally worked with them (and invite the same rigor on myself) and insist on being co-located to start with.  When the shits hit the fan, the most important thing is that the cofounders are still willing to stick together, which is a very strong requirement if you just compare it with other types of relationships like dating vs marriage.
• If you have disruptive technology (e.g. ChatGPT), you can create a market that didn’t exist before (AI chatbot).  Very few companies are fortunate enough to own a technology like ChatGPT, and in contrast, they have to make sure the market already exists – the best signal for that is there are already many big companies working on it.  Of course, you also need a novel solution (e.g. Notion for notes/docs), a better execution (Uber among tons of other shared rides attempts), or better distribution (Teams vs. Slack).  For our product, there were only a few super small companies doing similar things, a bad sign!
• GTM, sales, distribution, growth, however you call it, is super important.  I’d argue that it’s more important than the product, unless you have a disruptive product like ChatGPT.  And within growth, for a consumer product, organic growth is more important than paid growth.  The ads platforms today are pretty expensive; you are doing great if you can get <$10 CAC, but that is still a lot for the unit economics to make sense.  So you have to do as much organic growth as possible to spread the cost of paid marketing.  If you can organically grow as many users as your paid channels do, you can halve the CAC for the marketing spend.  This is why you see all the founders (and Elon Musk) shit post on social media – it doesn’t even matter what their personal image is as long as their posts create enough traffic to their products.
• Given above, you can’t have all the cofounders working on product development.  Sure, at the very beginning, everyone works on the product, but at some point, the growth, along with other responsibilities like investor communication, becomes a full-time job.  In my previous jobs, I didn’t understand why the CEO could be so remote to product development, but now I understand.  They are doing important work that only they could do (assuming there’s a competent cofounder leading product development).
• If something is business-critical, one of the founders has to personally work on it, even if they didn’t have previous experience with it, before delegating to external help or hires.  Non-founders almost never care as much as founders and have as much context as the founders do.  On the flip side, founders can’t effectively delegate and ensure quality without doing it themselves.