How Failing 2,032,198 Times Helps You Succeed

We’ve heard it so many times for entrepreneurs – how you have to know how to fail in order to succeed.

I wanted to dissect how exactly this is so.

How exactly does failure help you succeed?

My first instinct in answering this question is to look at my own entrepreneurial journey.

Has failure helped me?

When asked this question, my reply is almost immediate – yes, it has helped me tremendously. It’s not just because of the sheer learning that happens afterwards (though this is big as well, and is the basis for the lean startup movement)

The great thing that failure has given me is the stomach for it.

Having failed so many times before and knowing first-hand what the consequences are, I am mostly unafraid to try things out for the first time. I think this is where I get one of my strengths as an entrepreneur.

I would ace the question:

“when was the last time you’ve done something for the first time?”

Recalling just this year, I could easily name 20 things I’ve done for the first time (entrepreneurially, at least).

But thinking about it, this wasn’t always the case.

I remember a time when I was deathly afraid of failing, when I would rarely step out of my comfort zones.

So how did my paradigm shift come to be?

I remember after my college graduation, I decided to teach for a year. All my college friends went corporate. Naturally, I had the lowest salary in our group. Sure, I told myself it was the noble thing to do and I got to practice my speaking skills, but in truth, this bothered me. Knowing what I earned, I remember my friends would sometimes offer to pay for me when we went out. Inside, this killed me.

Upon transferring to corporate, I got a much larger salary. But then, tragedy struck as my family went through a big financial problem (which would drag on for a long time). Of course, I volunteered to help out and put in my share on the table.

So for a good number of years thereafter, I would work hard, get salary increases, and then see a chunk of it transferred out of my account. I had to find a way to make do with what I had.

In retrospect, these events transformed me.

I knew what swallowing pride was like. I knew what losing money was like. I knew what working very hard and not getting rewarded was like. I knew how to scrimp and live simply to make ends meet. I knew what failure was like.

So when faced with a decision where the risk involved failure? (a potential loss of money, reputation, comfort) As long as I found the reward side worth it, I would find myself taking the leap.

There was one particular instance in the founding of STORM where I think this all came to a head.

Back in 2005, Pao and I invested 30K of our money incorporating STORM. Ignorantly, we went (almost) all-in with one strategy: we spent most of the money arranging Flexible Benefits learning seminar. We thought we could pull in a few clients from the event.

The seminar was quite packed, but was a failure. It was a failure because when we met with the customers, we found they were expecting a fully working online platform.

We estimated it would take us a full year to technically develop the necessary system with our resources. The problem was, we only had a month’s worth of salary, since you know, we spent it buying food and wine for our guests in the learning seminar.

That would have been it. The decision WAS the wrong one and we dealt with failure and its consequences.

I never really considered folding right then and there, which, in retrospect, I now find interesting. (we had ONE MONTH runway left and had NOTHING)

Instead, Pao and I had that fateful meeting in that small cafe in Renaissance and did a pivot. We designed a new product in that meeting (an online survey tool, predating all the online simians), which Pao (incredibly) developed in a month. That became the basis of a very profitable business line which we rode until our Flexible Benefits services were profitable.

It wasn’t exactly smooth sailing after. We failed so many times after. I remember that time when I was praying to God and I felt so sure we would land that big account we were putting most of our eggs in. We didn’t. I remember putting up startups which failed and lost money. Or when people I trusted would lie to my face and betray me.

I know failure. I’m still afraid of it, but since I know I can take it, I don’t mind taking risks, or doing something for the first time.

My advice in all of this: don’t spend your days avoiding failure. There are tremendous advantages of knowing failure directly.

These advantages are quite evident in the stories of practically all successful entrepreneurs I know. This is why it’s very easy for entrepreneurs to share “war stories.”

In our time now, we see winners lauded like never before (and failure more scrutinized than ever before) We see comfort and pleasure being considered as THE primary objectives for a lot of people.

I think this is dangerous, because it leads to a life when the easy path is always chosen. This is NOT the path to any kind of success. We have to get used to taking leaps.

Sort of like this guy.

(Want to hear from like-minded people sharing war stories and ideas? Why don’t you check out JGL’s next Open Coffee session? You can register here!)