Confidence + Humility: Lessons from a failed startup

Confidence + Humility: Lessons from a failed startupPart 1: Confidence
A few years ago, I was a pretty excited guy. A venture capitalist loved my idea. He liked it so much he even wrote a blog post about it. I’m sure you can imagine the thrill – I literally jumped up and down, called my mom, and my face hurt because I was smiling so much.

This idea was gnawing at me, running cycle after cycle in my brain. Being a somewhat cautious person and a diligent student of startups I knew that I couldn’t get too carried away. The idea had to be [get ready for a startup buzz word] – VALIDATED – before I started sinking blood, sweat, and tears into it. Despite this whiff of caution, the initial positive feedback I got was exhilarating and there was a definite swell of confidence.

Part 2: Even More Confidence
To validate the idea I knew it was important to talk with customers: the people who would hopefully be paying (in droves) to use my concept. So I started networking – going out for coffee with potential customers, and asking people if I could “pick their brains”.

Somewhere in the back of my mind I remembered someone saying, “You should talk with ten potential customers before you start a new business…” I talked with way more than ten people and they all LOVED my idea. They would respond with “Wow! Let me know as soon as it is ready to go.”

Part 2.5: Spend Lots of Money
Once I thoroughly validated my idea by “picking the brains” of lots of people, I was convinced that I was holding the conceptual equivalent of a winning lottery ticket. Next, it was time to actually build the thing.

I hired a programmer, built an impressive brand, hired another programmer, and had a really awesome website built. The site was featured on cool web design galleries, and a prominent blogger writing about my idea drove my daily site visitors from 75 to a whopping 5,000-plus. Things seemed to be moving along swimmingly.

People were opting in to my pre-launch email list at a steady clip. If you were to ask me how things were going I would have told you, “great!”

While all this was happening I continued to focus for about four months on building the product. Then it turned into $ix months…then $even months.

Finally after about seven months, I thought we were ready to demo the product to all those customers.

Part Three: Failure
I sent login credentials to a slew of beta-testers-in-waiting. This was it! The moment of truth.

It was just a few hours later when my inbox started filling up with messages. Some of them were positive, but a lot of them had questions – “I really need it to do ‘this,’” or “I’m uploading a photo but it’s not the right size….”. A slightly panicky feeling started creeping into my consciousness.

There were a lot of good points that users were bringing up that we simply never thought of. How could this be? We did so much research! I even regularly visited potential customers as we were building the application to show them mockups and demo where things were at. The feedback at these meetings was always so positive! What in the world went wrong?

Death by a thousand cuts
The issues people had with the application were all small – the fundamental idea was still good. But there were usability problems. People were trying to use the application in ways that we never anticipated.

We had burned through so much capital trying to get to this point, it was really challenging to implement solutions for the feedback we were getting from customers. Our ship was heading towards the rocks. That little panicky feeling was turning into a big panicky feeling.

We tried plodding along for awhile, but things just didn’t work out as I had hoped. It was a failure – at least in terms of how I was defining success at the time.  My mind and body were reeling from disappointment.

Obviously there was more than one problem with this project. No one specific tactical adjustment could have saved us – it was a host of compounding issues that crippled our success.

What Happened?
If I had instilled one particular set of attitudes into our team and culture, it  would have made an enormous difference.

What are these attitudes? Confidence plus Humility. These are two “paired values” that at first glance seem to be at the opposite ends of the spectrum. However, if they can be harnessed together, the results are incredible. In this project I had plenty of confidence (you have to have a lot of that if you are going to launch a startup), and I even thought I had humility because I spent so much time and effort submitting my idea to other people’s criticism.

In reality though, all of my validating was just false humility. Instead of of legitimately looking at what customers needed, I was mostly just selling to them.

The Solution
Here are three specific tactics that could have helped me adopt a more humble attitude in understanding customers’ needs.

  • Don’t explain your idea; ask questions instead – When you are testing an idea your focus should be on customers’ needs, not on your idea. Customers will almost always agree with you if you pitch them a neat sounding concept. Instead, ask them questions about them, about what they need, and about their problems and challenges.
  • Let customers sit in the drivers seat – As we were going through the product development phase I would regularly demonstrate features to users. The problem was that I was in the driver’s seat. I knew our software inside and out. The customers didn’t. They would watch over my shoulder at a slick demo with pre-loaded info and say that it looked great. If I would have let them actually use the mouse it would have opened up a world of new understanding about our customers.
  • Iterate – Assuming that you can create a plan for the perfect product, work on it for seven months (without collecting any uninfluenced feedback from customers) and come out on the other side with something that works is extremely overconfident. It’s much more useful to take small bites, release quickly, and then collect real user feedback. Wash, rinse, and repeat.

What’s Next?
It takes incredible discipline and lots of practice (read: failure) to pair the confidence and the humility necessary to set a big idea in motion. The important thing is to focus on this relentlessly – it’s so easy to fall into the trap of selling instead of listening. Don’t do it!