How I fucked up my startup — life lessons from failing and imploding

Is it really better to burn out than to fade away?

Shival Gupta
Jul 3, 2017 · 9 min read

About a month ago, my whole belief system was turned on over its head. I realized that I had never been the wrongest in my entire life and it was a rare incident of reflection that promised to stay with me forever.

Make the car run before racing it on a race track. Vijay Anand of The Startup Centre gave me this brilliant piece of advice when I had just started Zeading in August of 2016. Alas, because of my tragic influence on myself, I chose to unconsciously ignore it or even worse, gravely misunderstand it. I had already failed spectacularly working on my previous startup 3 years back while I was still in college. I thought I had the awareness and was an expert on the mistakes entrepreneurs generally make.

And that is where I was wrong.

Never ever think that you’ve nailed it

Zeading was meant to be a blogging platform that made traditional reading obsolete. With our flagship feature — the Zen Mode, I had invented a clever way of using Javascript to convert articles into animated video-like interface on the client. With HTML5’s SpeechSynthesis API we had added support for voiceover as well — so it literally read out the whole thing for you. It was a really immersive way of reading stories. Our demos were jaw-dropping and we were flooded with positive comments about it in our beta run.

Our singular ambition with Zeading was to become the Youtube of textual content. It was an ambitious goal that stemmed from my own real life problem. I suffer from amblyopia, a rare condition in which one eye has dimmer vision than the other eye. It gives me a headache trying to read anything on a screen whether I use my glasses or not. My eyes are very sensitive to strain. To ameliorate this, I imagined our text-to-video interface, which provides an immersive, strain free way of absorbing textual content on a screen. Once it was done, and initial reviews were encouraging, it was time to capitalise on it — or so I thought.

Zen Mode in Zeading — played stories like video.

We had a fairytale startup launch. On the day of the launch itself, we had our first 100 registered users. In the next 30 days, this number had crossed 3000. On the 31st day of our operations, it was already at 4000. My team and I could not have been more amused. People were publishing on Zeading left and right and we had a lot of encouragement from our initial group of early adopters. In some ways, our first version had all the green ticks of a successful MVP. During the first 30 days, we already had our first influencer that we needed to transcend the boundaries of our own social networks. A bunch of very experienced people were also advising us from time to time.

Fairytale MVP launch

It was more or less like the celebratory champagne scene from The Social Network in my apartment — which was doubling up as the world headquarters of our tiny little venture as well. We astutely believed that at this point absolutely nothing can ever go wrong.

And then we jinxed it.

Product/Market Fit does not grow on a farm

What that means is that there is no way you can harvest a product/market fit after you’ve sown the seeds. Sorry to burst your bubble on this one, but it is just the way the world works. You have to design the product from customers, not bring customers to a product.

We learned all of this the hard way:

  1. If you’ve not done any customer research or don’t have any qualitative data about the existence of the problem that you’re solving, you will not get any users.
  2. If the size of your market is too small or you have little idea about the dominance of existing competition, your product/market fit doesn’t have any value.
  3. If your retention rate is too low and you don’t have a repeatable model for expanding into unchartered markets, you will forever be clueless.
  4. If your team members are all doing a full time job and are not instead working full time on your startup, you will have a very hard time moving even an inch forward.
  5. If your Plan A of revenue is advertising, you are royally fucked.

Product/Market Fit is, in effect, a reciprocal relationship that your product develops with your users. Your product adds value to their lives, users keep returning for more of the good stuff.

Looking back now, even the most viral story on our platform garnered just about 60k pageviews. Needless to say, we never made a dime.

Not having a north star metric is a recipe for doom

We studied all kinds of metrics except the one that really mattered. In our inane stupidity as inexperienced entrepreneurs, we analyzed everything Google Analytics had to offer and whatever we could make out from our database pullouts — daily pageviews, bounce rate, daily active users, signups, posts, number of likes, number of comments, Facebook page reach, yada yada, blah and blah.

If we’d just focused on pageview traffic, we could have worked towards our business model and optimized for revenue. If we’d just focused on engagement, we could have advertised ourselves as a community. If we’d just focused on our most used flagship feature, we could’ve focused on growing out of the blogging platform facade into a more efficient container for our value addition.

Choosing what metric you are going to chase is the most important business decision you’ll ever take. It will shape your product, business, and culture.

In the dark of a moonless night, we were left veering around the woods with nothing to hide our dignity with. Our once enviable growth crashed and hit x-axis like the drop of a Skrillex song. When the sun finally rose, we had nothing but each other’s faces to look at.

We didn’t look pretty.

Seriously, fuck your gut feeling.

Intuition without experience is the mother of all jackshit. Steve Jobs had great intuition because he was an industry expert. You are not yet. Your knowledge is sparse to say the least and your market study is fragmented and filled with biases and secondary data. You are not even allowed to have a gut feeling until you can explain the whole industry and it’s opportunities to someone in less than literally sixty seconds.

This may sound a bit controversial, but startups are instruments that run on intuition a lot by design. The only proven ways to build a successful product or a business have been either to follow what someone has already done or perform trial and error until you discover something unique. But how are you going to decide which trials to run? Your intuition is what will guide the way.

What if your gut feeling itself is wrong? You’ll waste all your resources running all the inconsequent tests. Worse than that, some tests will have false positives — like when we put Zen Mode on our article view before the article, our bounce rate dropped from 80% to 4%. It was a fuckall metric we never really bothered about because mostly viral content does have a rather high bounce rate, but because of this dramatic reduction we started putting in resources into embedding Zen Mode on other sites. This also did not pay off for us but rather sent us along a stupid tangent that we should’ve known better to avoid.

The only way to trust your own gut feeling is to train it to be right most of the time.

Experience and expertise make your thought processes aligned so that your intuition is mostly correct.

My friend and expert product and growth veteran Misbah Ashraf advised me to get 100 super-fans for my product before doing anything else. With our north star metric unknown and confirmation biases taking their own hormonal form inside our bodies, we began choosing our superfans based on our gut feeling. There was nothing quantifiable in our approach of selection of our most active users.

I feel embarrassed even as I write this, but it’s true. That is the extent to which we fucked up.

Salt and water does not make the sea

Unbeknownst to us, there might been have a better way to build and market what we were trying to achieve. In an alternate universe, in a parallel reality, I like to believe, there is some place where didn’t fall for these now seemingly obvious booby traps laid out by our own prejudices. Sometimes we fail by having too much doubt; sometimes we also fail by having too much confidence.

There’s an ancient Indian proverb that says naach na jaane, aangan tedha — which literally translates to don’t blame the floor if you don’t know how to dance. Seems an odd way to end this story, but however deep I introspect, I feel that that ignorance of our market and uninformed decision making has been the number reason why we fucked up our startup.

We had worked for about an year on Zeading and it was part of an emotional stasis in my usually uneventful life. Needless to say, all this shutdown was done with an extremely heavy heart. It took me a whole week to make the announcement on Facebook to our users. It was just so hard to tell everyone you know that you’ve failed.

Managing a fully bootstrapped startup while also working full time professionally made me more appreciative of any free time that I get. I began reading more to fill up the voids in my mental capacities and became more accepting and corrective of my own flaws as a leader, engineer, and an entrepreneur. Mostly, I believe the setback is temporary and the things that I’ve learned will help me bounce back and get back to doing what I really enjoy — making amazing shit.

Thanks for reading! :) If you enjoyed this, please make sure to hit that heart button. It encourages me a lot and would also help other people see this story.

Hacker Noon is how hackers start their afternoons. We’re a part of the @AMI family. We are now accepting submissions and happy to discuss advertising & sponsorship opportunities.

If you enjoyed this story, we recommend reading our latest tech stories and trending tech stories. Until next time, don’t take the realities of the world for granted!


Elijah McClain, George Floyd, Eric Garner, Breonna Taylor, Ahmaud Arbery, Michael Brown, Oscar Grant, Atatiana Jefferson, Tamir Rice, Bettie Jones, Botham Jean

Shival Gupta

Written by

Building @neo-bank. Full Stack Product Engineer (Product + Engineering + Artificial Intelligence)

Elijah McClain, George Floyd, Eric Garner, Breonna Taylor, Ahmaud Arbery, Michael Brown, Oscar Grant, Atatiana Jefferson, Tamir Rice, Bettie Jones, Botham Jean