10+ Years of Losing on the Internet

Every entrepreneur fails

I’ve been losing on the internet for 10+ years. It feels good to finally be succeeding.

In high school, I started a YouTube channel with friends. We racked up a few thousand views, but gave it up when we didn’t go viral.

As a freshman in college, I started a music blog with friends. We interviewed some famous musicians, but we gave it up because we didn’t know how to make any money.

When I found Tim Ferriss’s work as a junior, I started a blog, but gave that up because I didn’t see traction after two months.

Thankfully, somewhere between 2020 and 2022, I learned the value of patience. Maybe it was from COVID, but I think it was from learning to code.

In July 2021, I did a data science bootcamp because I was afraid my English degree wouldn’t get me a job. I figured I’d work in coding to pay my bills while I built up my reputation as a writer — and somehow, my plan worked.

I sucked at coding. I was absolutely terrible. I’d never done it in my life before the bootcamp. But, I pushed through, drank iced coffee by the gallon, and got myself a job on the data team at American Express.

This experience made me realize that when you suck at something, you need to keep pushing through if you want to succeed.

The Valley of Disappointment | Psychology for Educators [And More]

James Clear made the graph above displaying The Valley of Disappointment, the area in between what you think should happen and what actually happens. When I saw it, I immediately realized I gave up in The Valley of Disappointment way too frequently.

The need for patience probably seems obvious to a lot of people, but I never really got it until this year. The YouTube channel, the music blog, the old newsletter — I gave up because I couldn’t see progress quick enough.

I thought if you were good, the success comes immediately. It doesn’t.

You have to invest time in losing if you want to succeed.

Chess champion Josh Waitzkin calls this concept Investment in Loss. "Investment in loss is giving yourself to the learning process,” he writes in The Art of Learning.

Waitzkin was referring to his years as a kid practicing chess, but what I’m talking about is Investment in Losing Online — investing time and energy in writing tweets, making YouTube videos, and publishing essays.

Visualize Value on Twitter: "Keep going. https://t.co/Ct5Lfk3lny" / Twitter

Losing on the internet feels miserable. As Jack Butcher’s design above shows, it feels like everything is pointless until it doesn’t.

The musician Russ lost online for 10+ years. He self-released eleven albums before he saw true success. Now, he has 12M+ monthly listeners and sells out tours.

“Plays in the millions / Guess I'm finally blowing up / Oh, what a feeling / Ten years makin' beats / Patience taste bitter / But that after taste is so sweet”

- Russ, Manifest

I’ve been a fan of Russ since 2016 — he understands that in order to succeed in the great online game, you must first repeatedly fail.

I spoke to a screenwriter last week who wrote eighteen screenplays over ten years before he sold his first. Since then, he’s made movies with Netflix, HBO, and Amazon.

As a full-time writer, I fail every single day. None of my work is written in one draft. It’s constant failure, alterations, and iterations.

When I write an essay, I feel like 15-year-old me putting on a condom for the first time. For a moment, I’m terrified by the blank page — and then I just go for it.

“The first draft of everything is shit”

- Ernest Hemingway

This quote broke down my fears of writing badly. All I needed to do was type some shitty sentences and then I could edit them until they were no longer shitty sentences.

If you read the first draft of my essays, you’d think I was writing in English for the first time — at least that’s how coherent my first drafts feels to me.

The same goes for writing threads. It took writing 15-20 threads to have one finally go viral. Then that thread got me 5,000 followers in the span of 72 hours. I had to invest in losing over and over again to finally win.

The shitty part of failing online is its visible for everyone to see: friends, classmates, family members, and romantic partners. Being an online creator is fucking challenging and terrifying.

But remember, most people aren’t playing the great online game. They’re not trying to grow audiences and make money online. They are content posting an Instagram, getting their 32 likes, and moving on with their day.

So don’t be mad when people judge you, don’t like your shit, or make fun of you behind your back. Unless they’re creators, they are just online spectators — fans at a gladiators’ match. You are the man in the digital arena.

If I could tell a younger me anything, it’d be this: build a community of creators and builders.

“Information work in any domain is like weight training: you only grow when you exercise to failure. The only source of weight to overload your mental muscles is other people.”

Venkatesh Rao, Getting Ahead, Getting Along, Getting Away

Over the last year, I’ve built relationships with writers, artists, and founders. I knew no one on Twitter, but I messaged people, had phone calls, and met up in person.

My writer friends have been incredibly helpful in giving me feedback. We’ve exchanged essay drafts, jammed on ideas, and worked together on Twitter hooks.

Now, Cyber Patterns subscribers include writers from companies like WIRED, Andreessen Horowitz, and Microsoft. But somehow, I’m less anxious publishing now than when my audience was just my close friends and parents.

It must be some mix more confidence in my writing plus 10+ years of people seeing me fail on the internet. I’m happy and feel the growth.

If you’re not failing online, you’re not trying enough cool shit.

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