The other side of success

What's the purpose of Startup Social?

There’s a haunting line from Willy Wonka & the Chocolate Factory. One that’s become so profoundly disturbing to me, that I now turn off the film before ever reaching the end.

In the very last line of the movie after Wonka gives away his factory to Charlie, he turns to the boy and says “Don’t forget what happened to the man who suddenly got everything he wanted.“ Charlie, the picture of innocence, asks “What happened?” Wonka smiles “He lived happily ever after.” If that doesn’t break your fucking heart, I don’t know what will.

I think somewhere deep down we all know that nothing is further from the truth. We’ve all witnessed the catastrophe of success. The abysmal nothingness that accompanies it. So to look in the face of a child—after giving them the proverbial candy store—and tell them that all their problems will be solved and all their pain will disappear, is the cruelest of all the Wonkonian punishments.

The Death of My Childhood Hero

I recently finished watching the documentary Roadrunner, which chronicles the meteoric rise of Anthony Bourdain. It traces his success from chef, to author, to world traveler and TV personality, and ultimately culminates in his suicide.

The interesting thing about Bourdain was he was 43 before he ever found any commercial success. Before that, he was working as a cook, and by his own admission, not a very good one. When his book Kitchen Confidential hit the New York Times best sellers list, he was finally—for the first time in his life— able to get current on his rent, and pay the IRS ten years of back taxes.

Bourdain had been a hero of mine growing up, and watching this film was my way of searching for clues. I wanted to understand why, someone who had everything I ever wanted, determined that life was not worth living. The conclusion reached by dozens of his closest friends and family was that despite the travel, fame, meals, friendships, and wealth beyond his wildest dreams, he ended his life because of his inability to receive love. In the end, he felt deeply, and profoundly, alone.

What Would You Do with 10 Million Dollars

A few years ago, my aunt had more or less hit the lottery. She was living in Ecuador at the time, so the difference in exchange rate meant her lifestyle was that of a modern Cleopatra.

It’s a simple life she leads though, complete with a handful of genuine friendships. Surprisingly, her best friend and closest confidant, is her handyman. I got to spend an evening with him, his wife, and two young boys when he kindly offered to roast us an entire pig. He’s a kind man, with big dreams, big stories, and an intense love for his family.

A not-so-secret dream of his—one that he’ll poetically extoll whenever there’s a lull in the conversation—is to buy a little house on the beach and retire with his wife. You probably have a dream of your own like this, one that you can recount in vivid detail. One that you’ve visualized every nook and cranny of. You’ll share it with your mom, your friends, your spouse, and pretty much anyone willing to listen. It’s a dream that keeps you going, that makes all the hard work and difficult decisions worth it. A beach house on the coast of Ecuador was his.

My aunt, the newly minted multimillionaire, floated the idea by me of purchasing the handyman’s dream house and gifting it to him and his family. She figured, it would be a relatively small expense for her, while being life changing for him. It sounded like such a kind and warm-hearted gesture, but in that moment my heart broke. She was about to give this man everything he ever wanted. Would he and his family live happily ever after?

The Other Side of Your Wildest Dream

My greatest fear is for someone I love to achieve all their dreams, expecting that once they do, life will be different. That something, anything, will be on the other side of success.

Two years ago, when I moved to San Francisco, I had relocated to a city where everyone had a big vivid dream. A vision that pulled them along, that guided them, and gave them a reason to rise and face the challenges of the day.

For many of my closest friends, that motivation is to prove someone wrong. To confront a parent, or teacher, or ex-boyfriend who once made a passing remark that made them feel small. To return to the very spot and say, “Who’s small now?” For others, the dream is a rich life. Victorian houses, sunbathing on private villas, dining at Michelin-starred restaurants, the works. Still other dreamers—maybe most tragically of all—are motivated by the promise of more time.

I know what lies on the other side of these dreams, on the other side of success. I’ve seen it, you probably have too.

The Purpose of Startup Social

I am without a doubt, the least ambitious person you’ll ever meet.

I don’t really want things to happen, I don’t want to shape the world, or change things, I don’t want to hoard time, money, or status. Because I’ve seen—up close—the nothingness behind that. I’ve had family members achieve everything they’ve ever wanted, then call me up and tell me they feel completely alone and that they’re thinking of ending things. When that happens once, your taken aback. When that happens twice, you sit the fuck down and reevaluate this whole game.

Startup Social is a byproduct of that reevaluation.

It’s a weird business, right? Most people don’t understand how it makes money, or what my angle is. On the surface, it’s just an event business focused on people working in tech. But then, quite separately, there’s a newsletter that—instead of sharing links to tech stories, trending stocks, and AI news—extols the virtues of community, relationships, and happiness.

While there’s no grand architecture behind this business, I think the purpose has probably become quite clear by now.

Bringing people together is, I believe, one of the most important things I can do. I find no greater use of my time, than helping ease the loneliness that living in a city can induce. So I began focusing on helping people who, by their very nature, default to isolation. What if I brought them together, and gave them a space to share their experiences? A space where they could ask questions like:

Startup Social is nothing more than a curated vessel, a tone, a set of values, an unspoken agreement for kindness among strangers. It’s my best attempt to make sure that when we get everything we ever wanted, we can look up and still see a friendly face. That we’re not alone, and that we feel loved.


PS. If you’ve made it all the way down here and don’t feel that you’ve just wasted five minutes, consider hitting the LIKE button on this essay.

It helps others find it. And it makes me happy.

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