In our quest to be more agile and more nimble and more buzzword compliant, we seem to have become convinced of the value of “failing fast.” It makes sense, right? If you’re going to fail, do it quickly so you can move on to the next thing without wasting too much time or money. It sounds pragmatic, even sophisticated. But let’s be honest with ourselves. The operative word in “failing fast” is still failing.
Like it or not, tech success is often a function of budget. And when you consider that Chase and Wells and Citi probably spend more on toilet paper for the employee restrooms than you spend on tech, doesn’t it make more sense to devote your limited resources to succeeding fast instead of failing fast?
The Myth of Productive Failure
The idea that it’s ok to fail – fast, slow or somewhere in between – can be used as cover for a lot of deficiencies. It wasn’t poor planning; we just failed fast like we’re supposed to. We didn’t lack conviction; we just wanted to fail fast and move on. Our MVP missed on the V part? We just made sure we failed fast. You’re supposed to learn from all these failures, but quite frankly, I don’t think the credit union industry can afford to provide on-the-job training in failure to anyone.
I’d like to remind all the credit union technologists and fintech wiz kids out there that in our unforgiving, even cutthroat world, there are no participation trophies. Nobody will ever say, “Well sure, they failed, but at least give them credit for failing fast.” In short, nobody cares if you almost had a good idea.
The Risk of Failing Too Fast
We all know that speed kills. But have you ever stopped to consider that speed kills good ideas? When you get into a cycle of implement-fail-rush to the next failure, you may be throwing out the baby with the bathwater.
Anybody remember Ronald Wayne? I didn’t think so. Wayne was one of the three co-founders of Apple Computer. He owned a 10% stake, but got a little skittish over a $15,000 loan that Steve Jobs had taken out. So 12 days after co-founding Apple, he sold his shares back to Jobs and Wozniak for $800. I’ll let you do the exact math if you want, but my point is, failing fast cost Wayne tens of millions of dollars.
Isn’t there a chance that one of your “failures” could have been a massive success with just a little more effort and discipline? If you’re always instinctively headed for the exit door, your chances of getting called up to the winner’s podium are slim. Real innovation requires the stamina to work through the friction, not just the speed to run away from it.
The Opportunity Cost of Failure
We can’t ignore the time factor here, either. There are only so many hours in a day. If you spend all your time failing, how much time does that leave for succeeding?
When we celebrate the alleged lesson learned from a failure without scrutinizing the time lost, we’re not considering the true cost of that failure. Your board of directors and your members don’t pay for expensive lessons; they pay for results. Every hour spent pivoting away from a fast failure is an hour you didn’t spend building something that actually works.
AI: Failing at Scale
This problem is only getting worse with the rise of generative AI. That’s right. I said worse.
Today, AI gives everyone the power to fail faster than ever before. It allows teams to churn out mediocre code, “slopaganda” content, and half-baked strategies at a volume that used to take months of human effort.
We’re mistaking the speed of iteration for the quality of innovation. Just because you can automate a thousand pivots doesn’t mean you have moved an inch closer to a win; it just means you’re getting lost at the speed of light. AI should be a tool for precision, not a factory for digital participation trophies that allows us to be reckless at scale. Use AI to succeed faster than ever before, not fail faster than ever before.
The Effort to Win
“Winning isn’t everything; it’s the only thing.” That’s the most famous quote from the great Vince Lombardi: However, many people forget he tempered that with a dose of reality in this quote: “You can’t always be first, but you have to believe that you should have been – that you were never beaten – that time just ran out on you.”
What does this have to do with credit unions and fintechs? When you go into a project with the safety net of failing fast, you lose the edge that comes from needing to win. If you are not putting in the effort to win – and win big – from the get-go, you’re just practicing how to lose.
Lessons from the GOAT
I had the privilege of being invited to Velera LIVE in March. Certainly, one of the highlights for me was a keynote by Tom Brady. Not surprisingly, Brady didn’t talk about the virtues of failing fast so he could get to the next Super Bowl. He focused on the relentless, almost obsessive preparation required to ensure he did not fail at all.
Brady noted that later in his career, he thought about how he could use his time in the most efficient way to be as prepared as possible for those moments on Sunday. He explained, “It always came down, in my mind, to the processes over the outcomes.” He told the audience that when you prepare your best, you do everything to not leave the game to chance.
The Opponent in the Mirror
There is, of course, a fundamental difference between the gridiron and the boardroom. On the field, the enemy has a face and a jersey. In credit union fintech, there is rarely a head-to-head opponent trying to tackle you. In one sense, it’s you against the world; in another, it’s you against nobody but yourself.
That makes the “will to win” even more critical. When there is no visible adversary pushing you, the temptation to succumb to inertia is overwhelming. But in a world where we are our own toughest competition, winning requires a level of internal standards that perhaps doesn’t put too much emphasis on failing fast.
The Will to Win
I’ve always said that if I’m down by 17 points going into the fourth quarter, there are only three people I want handling the ball: Michael Jordan, Kobe Bryant, or Tom Brady.
It’s not because of how they played the game. It’s because of their will to win the game. Brady reminded us of this talking about his 28-3 comeback against Atlanta, noting that while there might have been a 99.9% chance the Patriots were going to lose, that probability would only have become 100% had they given up. He told his teammates that they might run out of time or they might lose, but they were not going to embarrass themselves by quitting.
Success is ultimately measured by whether you actually succeed. We need to stop celebrating the “fast fall” and start demanding the “fast win.” Because let’s be honest – if you’re not playing to win, you might as well stay home.
PS to TB12: One F bomb in a presentation like yours might seem edgy and provocative. Three of them, coupled with 10 S bombs, seem excessive and unprofessional, even to a shit-talker like me.


