11 Crazy Business Ideas That Made Crazy Money

Fuck product-market fit and fuck solving a problem.

The mavericks that built these ridiculous businesses didn’t have time for that shit.

No sir. They only had time for crazy business ideas!

These guys threw caution to the wind. They had an idea. They built it. They launched it. They kicked arse.

These are some of the most ridiculous business ideas that made money but shouldn’t have.

The pure audacity needed to pull off what these guys did is something to be admired, studied and copied. If you dare.

Here we go with 11 of the best crazy business ideas.

I Wear Your Shirt

11 Crazy Business Ideas That Made Crazy Money

Jason Zook loved t-shirts. So much so that he had an idea. Why don’t I charge people to wear their t-shirts? In 2008 I Wear Your Shirt was born. Each day Jason would get a company to send him their t-shirt, each day he would wear their shirt and let the internet know about it. I Wear Your Shirt started off small but ended hugely. Over the space of just 4 years, Jason made over $1,000,000 wearing people’s t-shirts every day. What a fucking legend. One of the best business ideas out there.

Ship Your Enemies Glitter

11 Crazy Business Ideas That Made Crazy Money

Australian entrepreneur Mathew Carpenter launched a website that charged you $9.99 to post an envelope stuffed with glitter to anyone on the planet. He called it Ship Your Enemies Glitter. The internet went mental. In a matter of hours, the site got global media coverage and sold more than 2000 envelopes generating over $20,000. Much more than this young bloke could handle. To top off this extraordinary tale of greatness, Matt ended up selling the site at its peak for an astounding $85,000. What a fucking ride.

The Pet Rock

11 Crazy Business Ideas That Made Crazy Money

In 1975 an advertising guy named Gary Dahl created the Pet Rock. According to Wikipedia, this dude packaged up smooth stones from a beach in Mexico. He put them in cardboard boxes complete with ‘breathing’ holes, straw and an instruction booklet. In one incredible run of 6 months, Gary Dahl sold 1 million pet rocks at $4 each! That’s 4 million dollars selling rocks found on a beach. That’s one hell of a crazy business idea that made crazy money. And all done before you could sell stuff on the internet. A rock-solid business idea indeed.


11 Crazy Business Ideas That Made Crazy Money

Entrepreneur Marc Köhlbrugge launched an experiment. In his own words he called it ‘a public leaderboard you enter by paying. Whichever amount you decide to pay, that’s your score. The more you pay, the higher your ranking’. He called in Highscore.Money. Insane right? People will never pay to see their name at the top of an internet leaderboard! Wrong. This ballsy move netted Marc a whopping $2251 in just 24 hours. Not bad for a day’s work.

Million Dollar Homepage

crazy business ideas Million Dollar Homepage

Alex Tew had a plan. Launch a website and sell space on if for $1 per pixel. He called it Million Dollar Home Page. One million pixels, one million dollars. A beautifully simple but straight up insane business model. The internet loved it. He sold all of his pixels and made a gross income of a whopping $1,037,100. Boom. A brilliant idea executed that brought in a shit tonne of money. Hat tilt.

Potato Parcel

A 24-year-old guy from Texas named Alex Craig started Potato Parcel, a business founded on the idea that people would want to send potatoes with messages scrawled on them. After the launch of the site, Alex was averaging $10,000 per month in sales. He sold more than 3,000 spuds in just four months. Six months after he founded Potato Parcel, Alex sold the booming business for $42,000 and put the money towards buying a house. Boom! That’s how it’s done, my friends.


11 Crazy Business Ideas That Made Crazy Money

Marc Köhlbrugge does not know when to quit. This time he came back with something even more audacious. He set up a website that charged people a penny for every letter they wrote on it. He named it ‘Expensive.Chat’ this brilliant piece of business savvy meets social experiment has made Marc over $430 so far. Who the fuck would have thought people would pay money to chat. Brilliant.

I Want To Draw A Cat For You

Steve Gadlin really liked to draw cats. So much so he set up a website that would allow you to purchase one of his cat drawings for $9.95 a piece. He called it I Want To Draw A Cat For You. Turns out people really wanted Steve to draw them a cat. Over the space of 5 years, Steve sold more than 18,794. That’s $187,000. Steve also appeared on Shark Tank, earning an investment of $25,000 from billionaire investor Mark Cuban. You read that right, Mark Cuban invested $25,000 in Steve’s cat drawing business.

Reserve A Spot In Heaven

11 Crazy Business Ideas That Made Crazy Money

Ever wanted to reserve your spot in heaven? Well, a couple of mates by the names of Edgar Kim and Nate Davis thought they could take care of just that. In 2007 they got together and launched ReserveASpotInHeaven.com. Reserve A Spot In Heaven sold “travel kits”— complete with boarding passes, certificates and “Heaven 101” booklets. Prices started at $12.79. Turns out a lot of people really wanted to reserve their spot in heaven. Upon launch, the guys saw a few thousand visitors each day. They then get covered by Fox news and made $4,000 overnight. In the following 2 months, they racked up another $11,000. Good Heavens that’s a lot of cash.

Santa Mail

11 Crazy Business Ideas That Made Crazy Money

American Byron Reese came up with an idea for a company. A company that would send personalized letters from Santa Claus to kids all around the USA for $9.95. In 2001 Santa Mail was born. In his first year of business, he sold over 10,000 letters. Fast forward to 2005, Santa Mail sales reached over 1 million dollars. The business is still in operation today and has sent over 500,000 letters. What a fantastic idea.

Ship Snow, Yo

11 Crazy Business Ideas That Made Crazy Money

As American Kyle Waring and his wife Jess were shovelling 4 feet of snow out of their driveway they asked themselves the question. Would anyone buy snow? A couple of days later they launched Ship Snow, Yo. Ship Snow, Yo offered to deliver a package of 2.7kg ( 6 pounds ) of snow to your door for $89. After getting some coverage on local news, it turns out that people wanted to buy snow. They received 100’s of orders within the first few days. Ship Snow, Yo is still in business today. It is reported to be a 5 figure seasonal business. That’s how it’s done, folks.


In a world full of A/B testing, data research and over analyzing the shit out of everything, it’s refreshing to witness what these guys did. These people’s crazy business ideas put the fun back into the internet. They broke the mould and redefined what a business model can be. Granted, some of the ideas shot up into the sky like a firework and crashed back down to earth. But that’s not the point. The point is they made their idea a reality and put it out there. Some of them with spectacular results. I hope these examples inspire you to throw caution to the wind and take the leap on that crazy idea today.

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