How Startups Fail Forward

We’ve all got a few big mistakes in us

Joe Procopio


Almost any top 10 list of the biggest technology product flops of all time will include a reference to Apple’s Newton and Amazon’s Fire Phone. But they will also note that the Newton was the precursor to the iPhone, and that the Fire Phone indirectly birthed the Amazon Echo.

Failing forward is a known business concept, especially in the arenas of entrepreneurship and innovation. But turning failure into success is not just a switch you can flip. The wrong mistake can be costly, and can shutter your business almost instantaneously. So if you’re going to make business-crushing mistakes on purpose, you should have forethought going in and fortitude coming out.

I’m not spinning out the next iPhone or Alexa, but I make my share of potentially business-crushing mistakes. The learning process is the same. So here’s a much smaller mistake I just made on purpose and what I did about it.

Planned Mistakes Are Never Actually Planned To Be Mistakes

Don’t let my wordplay undercut my point. I’m aware of the oxymoronic nature of the “planned mistake.” And I loathe the phrase “fail forward.” The terms are just too on point not to use.

Failing forward isn’t something you attempt. It’s not even something you consciously do. It’s simply the collection of experience and wisdom that comes from having made a bunch of mistakes in the past, when your “educated guesses” turned out to be hilariously off base.

And I use the term “hilariously” only because I can laugh about it now.

I didn’t plan to make my last big mistake, it just sort of happened when I lost focus. It was a self-inflicted wound, so it was “planned,” but I didn’t mean to do it, so it was a “mistake.”

Basically, I was expanding my marketing reach from my target market to an adjacent market. It was working, so I was getting more and more aggressive with my marketing approach. One day, I found the line, shrugged, and crossed it, which upset a lot of folks in my existing customer base, my target market, and the adjacent market.

So essentially, one night I went to bed feeling good about the plans I had just executed…



Joe Procopio

I'm a multi-exit, multi-failure entrepreneur. NLG pioneer. Building & GROWERS. Write at and More at