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Entrepreneurs

Most Side Hustles Are Built Around Selfish People. That’s Why They Fail.

Side Hustle Selfishness

Photo by Dylan Sauerwein on Unsplash


Imagine you got the greatest opportunity of your life.

Now imagine splitting it with five other people. That’s what I did today. My inbox lit up with one of those “holy crap, you’re talking to me” opportunities. My first thought was how do we rise together? I sent five names to the big-name person to bring in, and spread the goodness with a few deserving side hustlers.

No, I’m not Jesus. For most of my life I’ve been a selfish asshole.

Then things changed. Dreams got obliterated. Romantic partners left. Family members told me the truth. Now I hate selfishness. It’s a problem worse than a plague — it even caused the current plague. As soon as I see it, I run fast in the opposite direction.

The truth is it’s more fun to be unselfish. Paradoxically, unselfishness is the only way to win, especially when it comes to side hustles.

Greed is the dumbest side hustle strategy

Early in my career one creator got pissed off with me. They had a LinkedIn course. A few of us thought about creating our own courses. They got mad upset with me and stopped responding to my messages.

I found out later that they thought if we each had our own course, then we’d steal students from their courses. It blew my mind. I had always intended on creating a LinkedIn course. In fact, I had an online business when they were still in diapers. SEO, courses, eBooks, paid ads are nothing new to me. Any kid with a google search app can figure it out.

So they blew up at all of us and cut all communication. I was sad. They were a good person deep down. They just had no idea how side hustles work.


Let’s compare this approach. One of my creator friends told me a story. Him and his band of misfits wrote on Twitter for several years. They’d each built up decent-sized audiences.

One of them launched a Twitter course. The other creators all promoted it for free. Then another person launched a course. They did the same. Then they started sharing the revenue of their courses with each other.

Things evolved further. When you do one of their courses there are bonus lessons at the end that feature their fellow creators. This adds enormous value to students because they pay for one course and it feels like they’re getting ten courses in a bundle from ten different teachers. Genius.

You can guess what happened next. They built an empire. They branched out into books with the same strategy. Now this group of Twitter creators is literally taking over the internet with their side hustle.

The unselfish side hustle idea is nothing new. Don’t thank me.

If you’ve ever followed east coast or west coast rap, like I did as a punk kid, you’ll be familiar with mixtapes and remixes. Young American rappers would feature on the mixtapes of more successful rappers. It was like a gangster rap internship. Then when the new kid on the block got famous they’d do the same, a form of pay it forward.

Unselfishness builds hidden empires online. You just can’t see it. It happens behind the scenes in Discord Groups and Slack message windows.

Side hustles are lonely

Oops. There I said it. I get freaking lonely. No fellow office workers. No boss to screw up my day. My apartment is empty a lot of the time. It’s just me against myself. That’s not always a good combination. Some days I tell myself “this side hustle life will be over soon, pal.” That’s me being a knob.

A side hustle fails when loneliness takes over. The discipline to keep yourself grinding away is too hard. None of us are Yolo Elon with a billion in our pocket and able to endure 99 problems.

As soon as an obstacle gets in our way, we’re right back to whatever we did before we had a side hustle. It hurts like hell. There’s a way out. Connect with people who have a similar side hustle to you. Get in a group.

But be warned: choose optimists, not pessimists.

I’ve seen this technique backfire too many times. Creators will tell me “yeah, I’m in a Facebook Group and they’re all telling me everything’s screwed.” Of course it is. You’re in the wrong group.

“Screwed” equals opportunity to optimists.

Find a group of people who can leave things better than they found them. Find people who use creativity to see a different approach. Find people who say “what if this is good for us?”

Stay away from pessimists. Side hustles are hard enough without gassing yourself to death with opinion farts that assume nothing good can ever happen.

It made sense to be pessimistic in the past. But modern society is far safer, with limited downside and unlimited upside. Adapting for modern society means overriding your natural pessimism — Naval Ravikant

The 20 asks for every give brigade

Ever join an email list? Of course you have. You’re excited to get the first email. You can’t wait to open their newsletter. All you can see are rainbows, unicorns flying through their air, and pixies setting off glitter cannons. “It’s a great day to be human” you say.

Then this happens: “Hello, buy my coaching product.”

What the f*ck?

You feel like you’ve been molested. No how are you. No cheeky smile. No what’s your greatest problem.

We’ve all met selfish people who use their side hustles to backhand us in the face. Jump on Twitter and you see their feed full of external links. Their tweets are subliminal ads for some ask.

Instead of the Gary Vee “Give, Give, Give, Ask” formula, they’ve gone for asks and maybe one give a year. They don’t get it. We don’t come on the internet to be sold to like sex slaves. We have lives. We have feelings. We have problems. Can I just breathe for a sec, mate?

They think if they shout loud enough we will pay attention to their side hustle. No we won’t. Content platforms are for stories, how-tos, and helpful advice. Not content marketing side hustle ads. That’s creepy. Yuck.

There’s a simple solution. Stop talking about yourself. Stop plugging your side hustle. Step off the soapbox. Look for ways to be helpful without being creepy.

The winning side hustle formula looks more like this (sorry, Mr Vee):

Give. Give. Give. Give. Give. Give. Give. Give. Give. Give. Give. Give. Give. Give. Give. Give. Give. Give. Give. Give. Give … … … … … … Ask.

Get rich fast and die trying mob

Now we come to money. Selfish people let their side hustles fail by asking too much because they want to get rich fast. They think that we (“the people”) are their lottery ticket out of this one-way life to a wooden box in the ground.

Money from a side hustle doesn’t happen fast. Sorry. It happens extremely slowly at first, and then faster than Elon in a Tesla on Highway 1 after a gig at Saturday Night Live and a phone call with his barcode baby son’s mother.

Money screws up too many side hustles. It’s criminal. I blame Instagram for all the Lambo porn. It makes us think we “gotta get mine” faster than is humanly possible. Money isn’t the destination, anyway. Money is a little nitrous oxide to help an idea travel faster. That’s it. There’s a great solution to the side hustle money problems: use the $0 strategy.

Make $0 for as long as you can. Let your 9–5 job or your traditional business fund your life.

I tell people I want to wait as long as possible to ask for money from people who benefit from my writing side hustle. That’s right. For years I wanted as close to an empty pantry as possible. Why?

The longer you can starve the stronger you’ll get.

Earning $0 from your side hustle builds a reserve tank of reputational and financial energy. You can draw down on this energy when you’re down to your last hamburger. Until then, a starving creator with a side hustle dream is more powerful than a selfish knob who is guaranteed to fail.

Unselfish equals wild side hustle success in the making.


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Tim Denning
I am an Aussie Blogger with 500M+ views — Writer for CNBC & Business Insider. Inspiring the world through Personal Development and Entrepreneurship. You may have seen my work on Medium, LinkedIn, Bitclout, or Twitter.

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