I quit a startup after 1 and the half years working.

Many people have asked why I left my last startup, especially since it seemed to be thriving from the outside—we had secured funding, expanded our team, and perhaps even cultivated a respectable brand. Leaving my role as a co-founder may seem peculiar, as one might wonder how someone who "passionately" founded a company could decide to leave it so abruptly.

Despite the apparently favorable circumstances of the startup (at least to those outside my close circle), my departure after a relatively short stint raised some eyebrows and questions:

• Was there something fundamentally wrong with my last startup?
• Why did I choose to leave?
• Should others consider leaving their ventures too?

Since too many people have asked me about that, I decided to write this blog so that:

• (1) I could just sent this blog to the person without having to explain it once again
• (2) I thought it would be useful for those who're thinking about leaving their ventures by giving some principles for their decision making
  • I have already shared this to some of my friends and eventually "helped" they leave their startup. I'm not saying it is was a right decision, because what is right is delusional - I just think it is a useful framework or thought processing to take necessary actions.

In short:

• Was it a bad thing? I wouldn't say so. Generally speaking, for me it is something that is inevitable - that it is destined to happen for me to learn a lesson about life.
• Was it an easy decision? No, the decision wasn't something easy to make, physically and mentally. It was neither a surprised decision, it was something that escalate to the point it became clear that leaving is an obvious choice.
• Would I change my mind if I were to make this decision again? I don't think so.

To avoid having direct impact on the company's brand, I will obfuscate its name - for now, let's just call it an A company. My only motivation is to just share the lessons, that's it.

Just to add more context: my title at the A company is CTO, but my role is more of an intersection between Engineer and Product, meaning that I do everything to make things work, even in the dirtiest way possible (disclaimer: "dirty" here does not mean "illegal", it means "resourceful" 😂).

It started with this weird feeling

It all started with an unsettling feeling, prompting the question: "What the hell is going on?" At this point, I hadn't made up my mind, but I noticed that something didn't feel right. As someone who philosophically questions life's meanings, I found myself in a spiral of questioning:

• Why am I here?
• Why doesn't it feel right working here?
• Why am I not getting along with my co-founder?
• Why am I constantly frustrated by decisions made by the team?
• Why can't I see myself at this startup for another 5-10 years?
• Why have I lost my morning energy and enthusiasm for the industry? Have I changed?

Asking these questions would escalate the situation pretty quickly to the point that you became mentally exhausted. I remembered I became so sick (both physically and mentally), I didn't want to go to the office, I couldn't look my co-founder in the eyes, I felt miserable and disbelieved every decisions made in every meeting, and such.

Set a deadline

After 2-3 months later, I realized these kind of thinking wouldn't help me alleviate the problem or make myself feel better, and oftentimes turned into an overthinking rabbit holes relatively quick.

The better question to ask is: "Is it now the right time to leave?". The "Now" is important, because "now" is relative (..to current time, obviously). Either yes or no will bring you closer and closer to the ultimate answer:

• If yes: then you know what to do.
• If no: then... when?

"Now" assumed there's a deadline, and deadline is important for this kind of decision.

Reflect all the variables

Asking this question help me reflect all the related factors that would help me make decision easier, whether I should leave right now or later.

I defined it as two groups: (1) External factors and (2) Internal factors. External factors are those that outside of my scope of control and internal factors are those I can control it.

Internally:

• I don't see myself working in this field 5-10 years time. I don't feel like this is the field that I'm gonna work in the next 10 years because I felt it hard to let alone engaged with it: (1) I'm neither the user, nor (2) having the problem enough to sympathize with the users, nor (3) exposing myself enough to the industry.
• I felt that this kind of passion was not "optimal". I then reflected there were industries that I really love (like SaaS or Media Industry).. It's just not this industry that I was currently working in at the time. It has shown in the fact that I can communicate, craft a positioning for SaaS product, eloquently and energetically, just not with the startup I'm working on.
• I wanted to prioritise learning.
  • This sounds ridiculous: where else can one learn more than learning at a startup !? It was, I learned a lot during my tenure in my last startup. But because it was (too) fast-paced, I realized those learnings were rather short-termed and low leverage.
  • My learning does not add up over time, sometimes they're just chunks of information that are hardly connected. Every decision was made so quick and their reasons were not articulated, so nothing was learned (at least from my side). It was detrimental for a person of curiosity like me.

Externally:

• I couldn't play well with my co-founders outside of work. This does not mean my co-founders are bad, it just there's something that doesn't click between us. There is something not aligned at ... "soul" level? Or maybe just not the right time.
• I don't categorize this startup as a long term game with long term people.
  • I do prefer and appreciate that I have business partners with high energy - which my two co-founders are. It's just that.. sometimes, I don't feel like I respect them enough, and ironically trust matters a lot in this kind of relationship.
• Work philosophy is not aligned. I think my work philosophy clashed so hard with the other two co-founders to a point that I gave up on opposing, and started taking orders to reduce mental stress just to debate with the team. Although we agree with each other on majority of matters, those that we didn't - strike us hard. Tension was built and it escalated to the point it is no longer bearable. I like to think that I'm from the Ravenclaw's house and the other two co-founders are from the Gryffindor's.
• The company wasn't born to please me (not at this stage). Once I declared that I will quit soon, my co-founders spent a lot of time to keep me, this is obviously not efficient thing to do for a startup in a surviving mode. A startup at this stage should prioritize nothing except for its growth, and the fact that I stayed only add friction (if not damage) to the team.
• Aligned mindset is important. When we realized that we're not playing the same game anymore, let's call it quit.

Have I tried to fix it? I did. Prior to my resignation, I has helped established (not initiated) new business model and were in charge of going on-field to serve one of first customers of the model. But the more I do it, I felt I'm neither fit to this industry nor the team dynamics.

I can fake anything to fit in the motion, unfortunately I cannot fake my motivation. I felt exhausted to the point that I cannot continue working like nothing happens and fake that I'm happy..

Theory of "relative suitability": It is worth mentioning that not because I'm not great fit to other two co-founders doesn't mean others weren't - other team members are like a close-knit family to each other, maybe I'm just an exception. 😂

The Decision

The decision was made quickly after that, I bid goodbye to the team in the middle of February 2024. Just like any other resignation, I did a handover to the technical leaders to make sure the departure happened without causing friction or damage to the team. I planned and handed over for the cloud billing, services, all the processes, etc. It was brief.

Two week later, we hosted a meeting to announce my resignation; some of the members had predicted this would happen, while for others, the news came as a surprise. The meeting was hosted in a transparent way, like a conference panel and I was there to answer questions that the team might have related to my departure.

Some felt surprised, some felt regretful. But overall, it's a reflection point for the whole team to work on later. Overall, I think it was a good thing that I left.

So...what's next?

I must admit that I change my mind quite often as I collect more data, but there are principles that could never go wrong:

• (1) People. It all boils down to people-to-people interaction - Founding team dynamics matter a lot. Even early stage funding was a founder's bet, every startup video emphasizes that, but only when I confront this that I realized it was a thing.
• (2) Knowledge. Knowledge is important. I believe the way to sustainable wealth creation is accumulating a set of mental models or principles that works. From this day forward, I will spend more of time on learning and collecting high-leverage mental model that proven works.

Currently I've switched to a Product role at Holistics.io, working on building dbdiagram.io and dbdocs with the team I like, admire, while at the same time prioritize learning, sharpening my judgement, and get ready for my next ventures - Not sure when, but I will make sure I'm ready when it comes. 😃

If you're interested in this topic or need a mental guide for your entrepreneurial journey, please DM me via linkedin. I'm more than happy to share more :)