My First Startup Failure

My First Startup Failure

Paying The Price For Some Of Life's Most Valuable Business Lessons


I felt like jumping off our 12th floor balcony. Maybe if I was lucky, I could land in the pool below to tell the story how I sank $20,000 into a tech product and watch that be the one to actually fall flat on it’s face in the startup world. It turns out, this lost investment turned out to be one of the biggest life lessons in my career.

Since I had just helped a friend on the 14th floor make $7mm in less than 30 days (I’ll save that nonsense for another post) I was on top of the world and thought I could do anything. Instead of thinking I would be fresh on my way to jumping into financial freedom, I was now looking at a 120 foot drop after my first startup failure.

Back in 2006 I was trying to sell a product that was so obscure to the general public, only tech geeks in the nerdery would even know half of what it really does. I hacked Google’s IP datacenter just to make it work, praying they didn’t find out my product was actually relying on Google to allow customers to use a product that they didn’t even own. I even got on the phone with a PhD from D.A.R.P.A. who was building some of the craziest RFID technology who was like “Huh?”. If this guy didn’t understand the product, I was in for a serious wake up call.

About 10,000 downloads and a year and a half of giving away the product for free, the education level to explain the concept to customers was so cumbersome, it was time to move on. But not without learning a few things along the way…

Just Do. I was wrong to think I would be successful without trying. Putting any energy into something whether you think you are right or wrong will only be known until after you try. People don’t become successful by waiting.

Forget yesterday. I was wrong to think taking action on an idea would leave me worse off than when I started. If you’re going to focus on the past, be objective vs. subjective so you can see events for what they really are, not for what they aren’t.

Fire first, aim later. When you go out to test your idea , do it by talking to actual customers who might be interested in your product first before you invest any money into building something. You’d be surprised how much you can learn from actual people who would be interested in buying something when they give you feedback right away. Save these names for later, they will become your go-to crowd for testing your idea when it’s ready to build something.

Learn how to say No. Whether it’s a business partner, customer, or friend – always listen without judgement regardless of how baked into your idea you might be. But it’s easy to get carried away with new ideas to add, so remember why you started your idea in the first place. Too many ideas can be a hazard to executing that get in the way of real feedback that will help you.

Ask for help. Your family and true friends will always be there to support you. But there’s also a saying I have been giving to those who ask for advice these last few years when times get tough, when you have to dig in and  account for just how tough you really are: “Man is not measured by how many times he falls down, but whether or not he chooses to pick himself back up again.” I will never forget the day I made that promise to myself.

So in the end, I was wrong…

I was wrong to think this would probably be one of the worst failures I ever made. Instead, money was lost, so much time was poured into a failed product, but the learning lessons were worth every penny.

I can’t wait to do it again.