Startup complacency is the other side of success that nobody talks about

I started Wingify in 2010, and two years later, I went on a Euro trip where my business partner, Sparsh, and I took train rides across the continent. I recall proudly not checking my emails during that trip.

This is me not checking emails during the Euro trip I took two years after starting Wingify.

Don’t I look happy? That’s because I was happy. I was happy because Wingify, my fourth attempt at starting up after several failures, had succeeded beyond my wildest expectations. My aim with this startup was to make US$1,000 and prove to myself that I was a real entrepreneur.

I launched the company’s first product, Visual Website Optimizer (VWO), in 2010. Boy, did I get lucky. My benchmark for success was hitting a US$1,000 milestone. I hit that milestone in the first week of launch. In the first month, our revenue was US$4,000; in the second, it shot to US$9,000; in the third, it was US$15,000. By the 18th month, we had made a total of US$1 million in revenue.

Then, I took the Euro trip.

What exactly happened during the trip? Not much on the business side: Wingify’s growth was on autopilot, so I had all the time in the world to try Belgian beer, get lost in Shakespeare and Company, hike in Interlaken, and take Gondola rides. Beyond Europe, I found time to travel to many other places. After working my ass off to kickstart my company, I thought I deserved all the fun I had. But that’s not the point of this post.

The point is that, when I was starting out, my expectations of success were so low that when the startup started making money, I became complacent and didn’t realize that I was leaving a massive opportunity on the table.

But there was no way I could have known that.

A background of myself and the company

Consider who I was and what the company was in its early years (2010 to 2014):

As a first-time entrepreneur with no business training and only 1.5 years of “experience” working after college, I was caught in a whirlwind of growth that I was totally unprepared for.
Because I had discovered an untapped latent need in the market, our customer base and revenue increased every month, seemingly by itself.
Being in Delhi, the startup community was non-existent.
We were making more money than our expenses, so we never needed to raise VC funding.
As an engineer, our first 10 hires were other engineers.

Early years of VWO’s growth.

In short, the growth I was seeing—with little effort from me—made me happy, and there was literally no one who pushed me to grow faster. If I could travel back in time to 2010, I’d say to myself: