Thoughts from Working in a Startup

The test of a good CEO is how one responds under immense stress. I believe that is the most important behavior to observe that determines a CEO's capabilities and limitations. When you don't have much runway left and customers hate your product, it can feel like daily failures are chipping away what's left of your self-esteem. Negative feedback on your product may be interpreted as a personal attack, as founders invest financially, personally, and emotionally into their ventures. I've read countless articles on the traits and habits of successful entrepreneurs, but I think experiencing working in a startup is truly a fantastic learning experience. It has really educated me on the realities of leading a company and how I can imagine it to feel when stakeholders are breathing down your neck, pressuring you to deliver.  

This summer, I interned at a Singapore-based startup that has been operating for three years. They have raised over SGD $4 mm in angel funds, won multiple awards, and is a proud example of local Singaporean innovation in the SME landscape. The small team of four people (excluding myself and a part-time assistant) inhabits a small office space, sharing a floor with another well-known Singaporean startup called XMI. In my internship experience, I learned:

1. Passion

There's no one better than yourself that knows how passionate you are about a subject, despite any attempt to broadcast your burning desire to the world. What's interesting is that the passion I feel personally for my own projects is different than the passion I see that other people have. When I'm passionate for my own venture, I never actually say outright that I am passionate in it. I'm not conscious of this passion, but I see it as an interest that I want to develop. My personal belief is that passion is something developed from grit and experience, so to say I am passionate about a new idea would be presumptuous. The definition of passion is compromised when I apply it to myself. However, when I observe how passionate others are in a venture, I witness how this is the basis for their motivation and the lifeline with which they hang onto. Their conviction is contagious and motivates employees to drive the vision forward. When our CEO pitched a VC virtually, it felt lackluster and dry. The investor seemed superficially interested, but did not make any action to move forward. However, our CEO pitched the same VC in a face-to-face meeting, the VC was incredibly enthusiastic about driving the deal forward. This is why VCs value conviction in founders and look for a passionate team in early-stage investments. It's not the actual recognition of a passionate CEO (though that's part of the puzzle), but it's the fact that this certain CEO's passion can spark something in yourself. Only when passion is demonstrated by others can we recognize the value of it ourselves. We understand passion better through someone else than on our own. 

2. Job titles are fluid.

This isn't a new discovery, but it may be difficult for some to understand that in a startup, you may be asked to deliver on things outside your domain. In fact, I believe the reason why I was hired was because I was able to understand both technical and business principles. Even though you aren't asked directly, it's good to keep in mind since it allows you to brainstorm more that you can do for the company. It's all a part of the learning process, and I've found that the key to offering valuable work is to make speed and quality as habits. To me, the worker that gets the job done in a few hours is more valuable than one who burns the midnight oil just for the bragging rights of how much time you've invested. I noticed that being fast and efficient allows me to learn faster - I don't have to be an expert in it, but I just need to be conscious of how much I need to know and what I need to know. Thus, these habits enable me to switch between different roles quickly. If we restrict ourselves to titles and descriptions, it's very easy to overlook the additional value we can offer and bypass new learning opportunities, which are the most exciting parts of working at a startup.  

3. Balance uncertainty.

Leading a team is incredibly difficult. Moreover, when you're not sure yourself of what the startup's next step is, how can you assure enough certainty in your employees without being deceptive or too certain? I think there is a general level of tolerance for uncertainty. If there is too little certainty, than employees will not have enough confidence in your ideas to efficiently execute and will quickly lose any motivation. They will feel like they are excluded from the discussion and feel like the organization is not transparent. If there is too much certainty and you under deliver, than you are essentially writing checks you can't cash, with each time there's a bounced check, an employee loses some trust in you. Certainty and more importantly, how you communicate the company's well-being, is in line with how motivated employees are.