Saturday Morning Quarterback: There’s a Lesson In Every Failure, Even When There’s Not

Despite conventional wisdom, most startup failures happen not with a big, fiery explosion, but with the kind of splash a golf ball makes when it lands in a water hazard.


And you’re done.

This story is part of a topic series called Saturday Morning Quarterback, where I dive into startup topics along more life-oriented angles, like sports and parenting, to name just a couple. Visit my author page for more serious startup stuff.

Last Saturday, a friend and I headed out into a drizzly early morning for a 9:20 tee time. I started out playing really well, for me, but by the time we reached the 7th tee, drizzle became an all-out downpour. When we got to the clubhouse at the end of nine holes, we were both soaked, and all the other golfers had cleared out for the day, but I was in with my best score on that front nine.

So the question comes up as to whether or not we should play the back nine. I was adamant about finishing the round, looking to repeat my success and maybe play my best round of the year. My friend is a machine, and the rain wasn’t going to bother him. Maybe he’d rust a bit. Who knows.

“I got this,” I thought to myself as we finished our break and walked to the 10th tee.

And then everything went awful.

I sprayed my next dozen shots all over the course. Lots of triple bogeys, lots of swearing. I could have turned around and headed back to the clubhouse at any point, there was no one on the course to see me slink away.

It kept raining and it got colder and windier, my bag turned out to be not quite as waterproof as I needed, resulting in a soaked wallet and phone. I gave up scoring my round and started just trying different shots and practicing, but it was such a wet, muddy mess that there was no way to gauge exactly how poorly I was hitting. Except maximum. Maximum poorly.

I finished the back nine without a single redeeming shot, no feelgood moment, five lost balls, and I was cold, wet, hungry, and tired. My only accomplishment turned out to be my worst round of the year.

How does that relate to startup? If you’re an entrepreneur I don’t have to tell you. It just does. You get a moment like this every couple weeks.

Life, and especially startup, rarely follows the redemptive scripts of movies about sports or heroes or justice. And even when those movies go contrarian, they still lean on teaching moments over actual failure. Startup isn’t “Well, Rocky lost but he went the distance and that matters.” It’s not “Hey, at least they got the Death Star plans to the Rebel Alliance.”

It’s usually “Oh, we failed and no one really cares.”

But, to be completely honest, I know there’s a lesson there and I know it’s going to make itself obvious at some point. That theory was reinforced with another recent fail moment.

Last night, my boy’s Little League team got booted from the playoffs earlier than expected over a bad call. What’s more is the bad call was on my kid, called out when he way clearly safe while advancing the tying run to to third.

This is just the latest in what’s been a never-ending series of bad baseball breaks for a kid who is very good and tries even harder. But whether it’s a bad call, an untimely injury, whatever, he’s faced so much “what-could-have-been” that I can barely stand it.

And yeah, I’m also his coach, so believe me, if I could put it on him, I would. It’d be easier.

Since I was on the spot to come up with some kind of advice for him, I went with what I knew. It’s not the lesson, but it will hold you over until you get there, whether it’s a Little League game, a horrific round of golf, or the kind of startup failure where you go out with a whimper and everyone saw it coming except for you.

Next time.

The next round of golf I play is going to better right off the bat because at the very least I’ll have dry shorts and a solid grip on the club. And there are more metaphors in that sentence than I’m willing to admit.

The next time the kid is mired in a close game, his legs will be longer and stronger and he’ll hustle just a little bit more to make sure his season isn’t decided on a judgment call.

My first failed startup was successful for years. It made money and won awards and took me across the country to celebrate something I truly believed in. But then, in year 10, it stopped making money. Flatlined. Nothing I tried worked, and I finally gave up in year 12.

But then, a year later and after several minor tweaks, the ashes of that startup became my 10th startup, and I sold that in under three years for almost 100x return on my investment. It’s not something I planned when everything had gone up in a puff of smoke, but had it not, there’s no way I could have done the new startup, and I definitely would not have had the sense to grow it into something more viable.

My most recent failed startup still sits out there today, staring me in the face every once in a while, waiting for me to figure out the lesson so I can go make something awesome out of it.

So failure: It’s not about falling nine times and getting up 10 — or whatever the math is on that. It’s not about just about learning from your mistakes, it’s waiting until the right moment to discover the mistakes and apply the lessons. Until that moment happens, just keep telling yourself that there’s a lesson in there somewhere and at some point you’ll be glad it happened.