July 29, 2014
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The only way to guarantee startup success

What is it like to reach the pinnacle of success? Is that where you attain happiness and fulfillment? Or are those found right here, right now.

Everyone said this would be the most embarrassing moment in the band’s eight-year career.

Depeche Mode had decided to play the Pasadena Rose Bowl—capacity 60,000—for the 101st show of their 1988 tour. To sell out would make it one of the largest music concerts ever played in America—highly unlikely for an English electronic band. Claiming they were popular enough to fill that stadium was an audacious act of bravado that critics were eager to see transform to humiliation as they played to a vast, near-vacant space, mocked by the each of the tens of thousands of empty seats.

KROQ DJ Richard Blade knew that secretly the band themselves were doubtful. As he sat with singer/writer Martin Gore in the empty stadium before tickets went on sale, Martin “confided in me that he was nervous and hoped they could at least sell out the floor seats—just 10,000 tickets.”

But the show sold out, with paid attendance greater than any Rose Bowl event in the eight preceding years. It was the defining moment of the band’s career—the moment when they undeniably “made it.”

And yet, simultaneously, one of the saddest moments.

Again from Blade:

“Backstage, after their amazing performance, I chatted with [lead singer] Dave Gahan as he cried from pure happiness. He told me that the tears were because he didn’t know if the group could ever pull off anything this great again and for him it was the most emotional concert of his career.”

Indeed, they never would pull off anything that great again, even though they increased record sales, wrote more hits, released more albums, played more tours, even reforming the band after the loss of one member and through multi-year battles with drugs, alcoholism and depression from the three remaining members.

It’s true though, what could top that moment? After you’ve proved everything that could be proved, to the critics, to your fans, and even to yourself?

What does it mean for you or me, that reaching the pinnacle of success is not only strikingly fleeting, but also unhappy? That tears of joy transmute immediately to tears of sadness, because reaching the peak means by definition your next steps must be downhill?

The same thing happens at startups. It’s well-documented that immediately following the “success” of an exit, founders almost inevitably fall into a sadness and even depression, as I’ve written about before.

It could mean this is all for nothing. That our fleeting moment of noon-time glory is cruelly bookended by years of gut-twisting emotional mountain-climbing in the a.m. and a meandering, permanently unfinished quest for meaning and purpose in the p.m.

It does mean this, if you let it. The way you let this happen is to believe that the goal is to achieve a single moment of success—a big sale, going public, or passing it on to your daughter.

Rather, you must understand that it is the building, not the result of that building, that matters.

Let’s break it down:

You spend 99.99% of your time on the journey of building a startup, and 0.01% basking in the temporary euphoria of “success,” such as selling it to someone else or ringing the bell on the morning of your IPO.

If that moment even comes, which it most likely will not. Often 100% of your time is spent on the journey, 0% in euphoric ecstasy.

If you look back and say “That was a wonderful time in my life. I’m glad I did it, and I’d do it again. Sure I would do some things differently—is that not true of anything?—but I’m proud of what I did and I’m stronger and wiser today than ever before. I created terrific jobs, where great people were empowered to build important things together, who were comfortable and safe, who shared in the bounty of whatever upside we could muster, and who themselves would also say they’re personally fulfilled just as I am.”

Then you win.

But if your measure of “success” is based on a specific outcome—based on metrics, or money, or growth-rate, or number of employees, or whether you had an exit, or how much money you raised, or how many humans you cajoled into sticking their nose in your app, then mathematically you’re almost guaranteed to fail, but only because of your own definition of failure. You’re guaranteed to spend years of your life in nervous agony, chasing an outcome you think will make you happy instead of making all those years be the years you are happy.

Then you lose.

Don’t get me wrong—I love making money, I’ve made plenty from previous startups and I hope to make plenty more at WP Engine, and so do our employees (all of whom are shareholders) and our investors. And honoring metrics is part of building a high performing team and building a huge, sustainable enterprise. Nothing wrong with using metrics and money to keep score in this game.

Keep score, so long as you can distinguish between the game and life. Keep score, while also basking in the thrill of generating happy customers and launching unique products and gathering the energy and brainpower of brilliant humans tackling interesting problems.

In fact, I’d argue that focusing on the nature of the journey solves one of the great riddles facing all startups. To paraphrase Peter Thiel: the first employee joins because it’s the ground floor of an exciting startup, but why will the 20th person join? Or the 200th?

To be part of the journey.

That’s why you should be there too.

If you value the journey, your “success” is guaranteed.

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