I have failed a lot in my career. Even admitting this is antithetical to what is considered normative in our society. Americans are drilled from an early age with the mantra: “Never give up.” We venerate persistence and glorify winning in every aspect of life. Walk into any school in the country and you might find these plastered on a motivational poster:

“Winners never quit, and quitters never win.” (Vince Lombardi)

“It always seems impossible until it’s done.” (Nelson Mandela)

“Most of the important things in the world have been accomplished by people who have kept on trying when there seemed to be no hope at all.” (Dale Carnegie)

And that wall follows us from kindergarten and into the workplace.

This mantra may work well for athletes (at least the ones who end up “making it,”) but I find it really problematic for entrepreneurs.

Failure is Not a Dirty Word

It hasn’t been all failure for me. I was lucky enough to start my career with a success: Google. In fact, success is probably a massive understatement. I was not an early employee, but I was able to see what a successful product and successful company looked like.

After leaving Google, I partnered with two guys to work on an idea we had in the personal finance space. We were going to build an innovative product with the business model in the image of Mint.com, but once we did our research and realized that the model didn’t work even for Mint.com, it was time to change things up – this after only a couple of months of work. I told the two other co-founders that I liked working with them and would love to keep working with them, but it would have to be on another idea. Any other idea. They wanted to keep trucking on the personal finance idea, so we parted ways. I only ended up investing two or three months of my own time, and shortly after, they dropped the idea altogether.

After that, I started a company with three other guys in the e-commerce analytics space. We got some good initial traction, but never saw the big growth that we needed. We stagnated. With stagnation comes the startup death spiral: no new funding, which leads to an inability to make major product or marketing pivots, which leads to a downfall. We had enough revenue that we could have tried to eek things out for years to come, but we saw the signs and moved on. Total time invested: about two years.

Next, I joined a seed stage company in the social media tech space, taking the place of an outgoing founder. Within a couple months of this endeavor I realized two things:

The product/market fit was poor at best
We were the wrong people for the job. My co-founder was running sales and had little to no experience doing so. I was running the tech stack in a technology I was unfamiliar with, and similarly had very little to offer. We were the wrong people working on a product that wasn’t taking off.

I invested another two or three months in this venture and moved on.

Changing Mantras

I share this supposed string of failures to illustrate that “fail fast” is a much better lesson to live by for entrepreneurs. I have witnessed so many young energetic entrepreneurs toil around on a startup idea for years because they got a bit of traction on their concept in the early days, and indoctrinated to never give up, they pushed harder and longer than they probably should have. These men and women have so much promise, and it frustrates me to no end to see them still trying to make that dying company grow legs.

There are, of course, stories out there of some company that flatlined for a decade until it hit the sweet spot and then made it big, but this is by far the exception to the rule. In general, entrepreneurs would have much more success if they took the lessons they learned from their first failed idea and moved on to their second (or third or fourth).

Iteration is the Mother of Success

After a few false starts, I ended up at Pendo as the first hire. Within a year I could tell it had legs. We found a sweet spot with customers and are now growing rapidly. Now, as the VP of Product, I try to instill “fail fast” as our mantra internally. It makes us better at what we do; we are not enamored with anything we build until it’s absolutely great. We take risks, and sometimes we abandon them.

Life is short. Make the most of it. Just because you’re taking a risk doesn’t mean you should commit blindly. If something isn’t working, take another risk. Embracing failure will make you more resilient and better prepared for your next venture.

That’s my story of giving up – with great outcomes. What’s yours?

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