Somewhere, Over the Rainbow

Some thoughts on Tony Hsieh, winning, secrets, and addiction

Welcome Entrepreneurs. I’m grateful you’re here.

Before we dive in, friendly reminder to check out the 2020 Annual Reflection template if you haven’t already, it’s a structured way to turn the page intentionally on 2020, and set the stage for an amazing 2021. The holiday season creates a natural space to pause and reflect, but it only comes once per year so it’s worthwhile to take full advantage. I hope this template helps you to do just that.

Now then…

Over the past couple weeks I’ve had a chance to process my feelings on Tony Hsieh’s tragic death. I’ve been up, and I’ve been down, and after all that I’m left feeling like I should speak out. Like I have something to say that might, maybe, help someone.

Fair warning, this isn’t your every day Second Mountain Startup fair. This isn’t punchy and practical (although there is a call to action at the end). This is the type of conversation we’re trained to look away from, in the same way we avoid death and the homeless. It’s easier to pretend that because they don’t immediately apply to us, they don’t need our attention.

But sometimes the most important parts of the entrepreneurial journey are the gaps in between all the hustle and striving, where we take stock of where we are, and how we might help not only ourselves, but each other. Sometimes even when we’re up, (especially when we’re up) it’s important to recognize that others are down, and, if we can, reach out a hand. And sometimes, even when it looks like we’re up, we’re actually down. And that needs to be ok.

So here goes.

Somewhere, Over the Rainbow

Tony Hsieh’s death rattled me. At first it was a tragedy, an icon of happiness taken from us too soon which, while incredibly sad, was also easy to move past. But then the real circumstances surrounding his death became public, and the depth of the situation became clear.

For many people, myself included, Tony was the pinnacle of conscious capitalism. He was the prime example of what success could look like if you put people first. If you truly cared about people as your primary mission, breathtaking economic success could in fact be the result. He did this better than anyone else, to my knowledge.

And it still wasn’t enough. His death wasn’t a suicide, but it wasn’t a freak accident, either.

There’s a promise we all believe implicitly, by virtue of our being born in America, that the darkness inside us, the loneliness, despair, rage, resentment, the sadness, there’s a promise that America makes to us that if we can only win, everything will be ok.

Winning takes many forms. Maybe it’s simply hitting your next quarterly milestone. Maybe once you do that, then it’s hitting your annual milestone. Maybe you do that a few times and then it becomes exiting your company. IPO’ing, maybe. Maybe you do that, and then winning is bringing happiness to everyone in the world. Winning, and with it the promise of peace, is always just around the corner.

And even when you deliver happiness to the world, it never comes.

I see you, Tony. I see your heart, your compassion, and your overwhelming love for people. And I see your demons. Your not-enough-ness, and your loneliness. The things that sometimes feel survivable only with chemical help. I understand what it is to look ahead and see bleakness. I understand wanting to push the shallow world away, because they don’t understand. I see all this in you because it’s in me, too. I’ve been down to the dark place. All the way down.

I barely survived it. And only because I finally, after way too much pain, was willing to open up to people. To share my story, my struggle with my own not-enough-ness, my addictions, even though every reptile instinct in me said to keep it secret.

Someone wise told me that addiction is an elevator that only goes down, and you choose when you’ve had enough pain to get off. That’s as true for winning as it is for nitrous oxide or alcohol.

Sober for nearly 14 years, I spent the last 13 years addicted to the chase. To the thought that winning was the Answer. I count myself incredibly fortunate to, finally, after so much pain, have found a way off that elevator, too (mostly). A way to let go of the chase, even if only for a moment. A way to be here, now.

It breaks my heart that you, with your joy and your caring and everything you gave and were going to give to the world, that you, Tony, didn’t find your way out of your hole in time. And it reminds me that no matter how amazing it looks from the outside, every one of us is in the battle of our lives.

This promise. The one that says that winning, hitting that next milestone, getting the bigger job or house or bank account, whatever. The promise that says that winning will finally make us feel whole. It’s time that we reevaluate that promise. As individuals, yes, and as a society.

It’s time that we talk about the part of us that we keep hidden.

The world will miss you, Tony. We learned so much from your generosity and spirit. I pray that we will also learn from your darkness, and reach out to one another. When we’re down, yes, but as importantly when we’re up.

The Promise

There’s a scene in Queen’s Gambit in which Beth Harmon barely beats Georgi, a 13 year old Russian prodigy, after a two-day match, and, seeing a younger version of herself in him, after the match she says he’s the best she’s ever played. She says that, and then asks him what he wants from his chess career.

“I will be the chess champion of the world in 3 years,” the 13 year old replies.

And you believe him. Our wiring sees this and responds to it. Yes, you believe him. He will be the champion of the world, and isn’t that inspirational.

“And then what?” Beth responds. “Once you’re the chess champion of the world in three years, you’ll be 16-years old. Then what will you do with your life?”

The look on his face is terror, confusion. A hard error to his operating system. Does not compute.

I can relate. As can most exited entrepreneurs I’ve met.

Perhaps Jim Carrey was right:

“I think everybody should get rich and famous and do everything they ever dreamed of so they can see that it's not the answer.”

The Secret

So many founders, myself included, start companies to win. We all have our darkness, our loneliness and our trauma, but we believe that if we can only get to that next milestone, if we can only become “successful,” whatever that means to us that year/month/week/day/minute/moment, if we can just become our own version of the chess champion of the world the darkness will go away.

We also know we can’t talk about this. We’re sure, certain, that everyone else doesn’t have this darkness. That they’ve got their lives all figured out, and their companies all figured out. We believe that the darkness inside us is our weakness, and we believe that we must hide it. We can’t let the world see our frailty, lest they see how unworthy we really are, and put our next coveted win in jeopardy.

But a few brave pioneers are speaking out about these issues, telling their stories of pain and loneliness. More entrepreneurs each day are taking the leap, being vulnerable in public about their struggle.

We should all be so free. In life, and in business.

This is progress. This is the beginning.

As implied by the timing of Ryan’s post, and explicitly stated by Sahil, it starts with the “successful” entrepreneurs speaking about their experience. Their real experience. And then, over time, by degrees, perhaps the rest of us might see that opening up doesn’t mean career suicide.

Here’s Sahil’s story.

Here’s mine. And mine.

The Research

Andrew Reiner, author of “Better Boys, Better Men” wrote an article in the New York Times this week exploring the unique way that men relate to loneliness and emotional isolation. The way we hold it inside as our burden, our shame. And the way that darkness, so tightly concealed within us, the way it can lead to situations like Tony’s.

He explored the latest research:

  • Excessive pressure to conform to traditional modes of masculinity increases the risk of men’s suicidal behavior

  • Boys are “trained” to follow a form of competition early on that defines their male-male friendships, discouraging honest emotional sharing “at all cost while encouraging direct competition and ‘one-upmanship’” … ultimately tending to create a profound deficit in many males.

  • 77% of men polled suffered from anxiety and depression. 40% of those said that these mental illnesses undermines their performance in jobs, parenting and relationships, but it would take thoughts of suicide or self-harm for them to consider seeking help

We are taught to value winning over all. In America, yes, but even more acutely in startups. And men are taught not to talk about the impact of this approach to life, the way it isolates us from other people, particularly other men.

The article was about men, but it’s not just about men.

Here’s Brene Brown’s story.

How you can help as a human being

I spent three decades of my life chasing the next win. During those decades I got a BFA and MS degrees, graduating early both times. I discovered my alcoholism, tested my limits with drugs, nearly died in drunken car crashes (thankfully involving only myself). I familiarized myself with our justice and detention systems. I also built a successful, high growth, industry transforming company.

All those experiences aren’t as dissimilar as they may read. Winning, I’ve found, is subjective.

Many of us founders believe that the success of our company is the ultimate win. Vindication. An exit will fix everything. We think of the money it will bring. The prestige and admiration. Once we’re successful, we tell ourselves as we put the mask on in preparation for another day, then we’ll find peace.

In the meantime, we carry our burden in silence.

If we survive long enough, which Tony Hsieh reminds us is not a guarantee, many of us learn that success doesn’t bring peace. Not lasting peace, anyway. Neither do substances, or experience chasing. Every over the rainbow is not enough.

Battling all this, it’s easy to feel like you’re the only person in the world having these thoughts. I’m sure Tony felt that way.

But you’re not alone. I hope you know that, now.

And if you do, I hope you also know that reaching out, even doing something as simple as sharing your story, might help someone else realize that they’re not alone, either.

How you can help as an entrepreneur

Regular readers know I’m nearly 14 years sober. I’m an addict, through and through, but I’m fortunate in that my sobriety has become something I don’t think about regularly any longer. Many people have it much more difficult. Many, as we saw with Tony, who you wouldn’t think. This is why it’s so important to talk about.

But some people are doing more than talking. Robin McIntosh & Lisa McLaughlin started WorkIt Health, a sort of digital rehab, after meeting at an AA meeting many years ago. They are a great example of a mission-driven startup, using the power of venture capital to change the world. This is what entrepreneurship can (and in my view should) be about, rather than creating the next decacorn app. That said, they may be a decacorn eventually (they just raised $12m, which is a huge step) given the scope of the problem they’re addressing.

Their work is important and so needed, considering that “The top 10 percent of American adults - 24 million of them - consume an average of 74 drinks per week or a little more than 10 drinks per day” (HT @schlaf). And their stated focus is ending the opioid crisis.

You don’t have to build a me-too app to strike it rich as an entrepreneur. You don’t have to choose between purpose and success. You can have both.

The world will be better off if you choose to.


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