The only way to guarantee startup success


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?

But 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?

What does it mean for you or me, that the same thing is true for 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 on this blog.

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.

37 responses to “The only way to guarantee startup success”

  1. Jason, thank you for writing this. I hope a lot of young entrepreneurs read this as its wonderful advice. I tried two startups in the last three years and completely ignored my family & friends while I was working on them. I had the lens of “making it one day and then I’ll make time for them.” I have learnt from that experience!!!

  2. This couldn’t have come at a better time. Our startup has continued to make progress in leaps and bounds (revenue, team, investment, product) but when we reach milestones that I should be ecstatic about, I feel like it’s not enough. This then feels worse because I get mad at myself for NOT feeling more ecstatic. By concentrating on the journey, the milestones will be (cliche aside) just the cherry on top. Where the real value will come from is creating something great with, and for, a great group of people.

  3. Everything about this post is dialed in: The title. The hook. The anecdote. The message. The conclusion. Amazing work, Jason.

    The message was especially relevant for me right now as my little SaaS approaches 100 customers (91 atm), and my partner and I inch towards our market salaries… I often catch myself looking off into the distance, and have to remind myself that “this is it! we’re doing it!”

    Thanks you, Jason.

    • Yes you are! Nothing beats the rush of those first few customers. How in the world did they even get here? :-) There’s joy (on top of hardship) every day.

  4. Wow, I could not agree more. Jason, as I think you are aware, I do a daily quote and blog on many topics, and this got me thinking about 4 of the quotes that can succinctly explain this. The first quote is pretty much what you said in your article:

    “Remember that happiness is a way of travel not a destination.”
    –Roy M. Goodman

    This gets to the root of what is happiness. It is how you travel, not necessarily where you are going. Taking this to the next level, Albert Schweitzer stated:

    “Success is not the key to happiness. Happiness is the key to success.”

    Which is pretty much why we do what we do. We really want to be happy, and mistakenly think success brings happiness, when in fact it it the other way around. A friend of mine, Travis McAshan once told me:

    “Happiness is doing what you love, success is getting paid to do it.”

    Which is sort of the modern version of having your cake and eating too. Do what you love, and if you can get paid for it, so much the better. And finally, I close with:

    “Success is getting what you want; happiness is wanting what you get.”
    –Ralph Waldo Emerson

    Really, the ying and yang of what and why we struggle with success and happiness to begin with. If you can make you wants align with what you get…then my friend you will be happy..but alas, so few of us are happy with what get get, for we do not know what we truly want.

  5. Jason amazing article. I sold my last start up just over a year ago and shortly after I suffered that let down/depressed feeling you described. For me thought it wasn’t because I was focused on one point of success but it was because I was no longer on the journey building something meaningful. It took me a while to figure that out that I am lucky as I value the journey more than the end. I think your perspective is the correct one.

    • Thanks for sharing that. It’s hard to figure out what’s causing it — loss of identity, the daily challenge, the prestige, staying relevant in the world, etc..

      • I think it is a combination of a few of the things you highlight. When you stop working on something you are so closely tied to and spent so much time on it fundamentally changed how I thought of myself

  6. This is profound because my startup consumes every waking moment of my life. This moment is the journey and the journey is your life. So every once in a while we should take a moment to stop and look back at how far we have climbed and just enjoy the view.

    We should be truly grateful for the present moment. If you cannot enjoy the present you will not be able to enjoy the future. Success = Status but Status doesn’t = Happiness. Unless you use your success to create happiness for others. Happiness = Helping others = Purpose

  7. This article is well-written. Great job Jason. It is all about the journey and not the results.

    My journey in my startup wasn’t easy and I’m still working on it. But I just love what I’m doing, focusing on what I learn on my journey.

    Check it out at

  8. A wise person once told me “Enjoy the ride!”, referring to the rollercoaster that is a tech startup. Your message is totally spot on and I’m very glad I found my inner piece in understanding the difference between perceived success and real success. Thanks for this post!

  9. This insightful post comes at a great time for me. In my journey, immediately following operational BE, I found myself wondering why I wasn’t happier. I’d ‘made it’, I had built a successful business, have happy employees, loyal clients, a recognizable brand that’s dear to my heart.
    I looked around for what I could/should do to ignite that drive and euphoria again. Over a few tormenting months I waded through these feelings. It was a dark time :) Comparing various paths I’ve traveled. It was like watching multiple movie trailers, each had an engaging build to triumph, defining moments the character grew, rewarding in completely different ways. I discovered for me it is futile to compare great movies. I thoroughly enjoy unique perspectives on lifestyle, climb to climax, and precise selection of cast / colleagues. Each has it’s own merits.
    That is where this post hits home for me, I drew the exact conclusion: Happiness is the journey. The challenges, reaching for the triumph and lovable characters that contribute to my overall happiness during the journey. This post gives me a sense of peace and camaraderie for understanding the way it felt. On to brighter skies, rewarding journeys, and amazing casts.

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