Startups, Coming Of Age, And Boyhood

People love coming-of-age stories. That fuzzy mix of nostalgia, longing, and “if I only knew that when I was younger.” What if your childhood and adolescence could be summarized in 2 hours? movie Boyhood took 12 years to produce, but we, the audience, have the luxury of witnessing the majority of a young boy’s life in matter of 2 hours while eating popcorn and Milk Duds. Working on a startup closely reflects this notion of compressed time. Instead of feeling the ups and downs over a period of 12 years, you feel exuberance and depression on a weekly and sometimes daily basis.

Startups and Space-Time

Albert Einstein’s Theory of Relativity suggests that we cannot agree on the time it takes for objects to travel relative to us. Imagine you are scrawny and decide to start weightlifting. If you looked at your body in the mirror over 6 months as you gain muscle, you would notice small changes to your body but not on a daily basis. Perhaps you see more defined shoulders one week, and a thinner waist the next. Over 6 months, the changes are apparent but you didn’t “feel” them every day. Now imagine you saw the changes in one day. How would you feel when you see yourself in the mirror? I would be utterly shocked and think I turned into the Incredible Hulk.

Before I started working on my startup, I read a lot of stories from entrepreneurs about failing fast and iterating until you find a product the market needs. It sounded like a roller-coaster ride but at the time, it was just that: a sound. Not until I plunged head first into startup-land did I understand the feeling of your heart dropping on the roller coaster’s first climb and drop. From day 1, I noticed how fast you learn skills like building an MVP and networking. The learning process is incredible. I could step back and see myself growing up fast to adapt with my surroundings (aka the market).

Playfulness & Optimism When Starting a Startup

At the very beginning, my team and I think about new ideas and concepts to try out. Luckily, our team has the technical know-how to actually build the ideas we concoct and dream about. As I start to talk to my friends about the idea, they become interested and we grab lunches and drinks to do more brainstorming and form partnerships. I feel completely free to do whatever I want because, well, doing a startup you can literally do whatever you want.


It doesn’t matter that the product is still rough around the edges; I am playing and enjoying the process of creating. This is one of the most prolific periods of working on my startup because I learn about new technologies, products, and business models every day. I actually enjoy being the dumbest person in the room because that’s how I learn new things. Once in a while, I might come across a bully who doesn’t like me for some reason and that’s fine, I’m ok with working on my own and not knowing where this idea is going to go. For the most part, I am just content with playing in my own sandbox with some new friends I made along the way.

The Popularity Contest

After all the great ideas and daydreaming about how awesome it would be to be a $1B company, our team starts building the actual product. Along the way, a few features get added and some are axed, but we the foundation is being laid. Slowly but surely, we put up the homepage, create a marketing strategy, and see what some of our competitors are doing. I feel like this stage is like middle school; you discover your identity and you develop a close group of friends whom will back up you on the playground.

originalI look at other companies in our space and want to be as cool as them. How did they become so popular? How did they get their first user and customer? Which reporters or investors are they friends with? I can’t help but feel pure jealousy and envy, and see my competitor’s popularity as something I want to achieve rather than something to earn. Nonetheless, when I’m with my team, I feel comfortable in my own skin and can focus on our own product. For the most part, my startup experience is still very much experimental, and I know that the product I build today may very well change tomorrow. Financially, I still have enough saved up to live and eat, so everything’s good.

Growing Up is Hard

More than a year passes by and my startup is fully functional and we even have some customers. What’s next? Where’s the exponential growth I’ve read on TechCrunch and Business Insider? Personally, my friends and family are still supportive but when they ask me innocuous questions like “What are you up to these days?” and I talk about my startup, I inevitably receive responses like “Oh. You’re still working on that?” The underlying meaning behind this question is that my friends (and most people you care about in life) expect you to have things figured out. Most business professionals with traditional careers appear to have things “figured out,” but startup guys and gals are the crazy people your friends might bring up to tell a story at a party.

I also see my friends less; finding reason to not go to happy hours, dinners, and casual hang outs. My social life is nonexistent, and I cannot block my startup from taking up headspace. When I worked in the stable corporate world, it was easy to shut off work when I left the office, but not with my startup. The startup is my new identity and when I hear negative feedback from friends, customers, and investors, it impacts me emotionally when I know this feedback should be “categorized” in the business part of my brain.

Perception is Reality

Most importantly, my fragile startup must appear to look like a fortress to the outside world. My personal life, financial situation, and the backend code itself are held together by masking tape and popsicle sticks. Somehow, some way, I make it through each test and challenge by relying on my team members and the cultish belief that we are doing something bigger than ourselves. To my peers, the positive growth and successes all look great on the surface, but only I know the banging-head-against-the-wall work required to maintain the appearance that the startup looks awesome.


At this point, is there any turning back? When you are a boy, switching your personal interests mean hanging out at one lunch table over another table. Being fully committed to one concept and belief is truly an insane way to live, but I cannot imagine living any other way. One day way in the future, I will look back and think about all the late nights, trashed mockups, and useless PowerPoint decks were necessary ingredients to help me grow as a boy into a man.

I’d rather die enormous than live dormant, that’s how we own it.

-Jay Z, Can I Live

This is a guest post by Al Chen, Co-Founder at Cooperatize.