5 of the Craziest Startups of All Time

5 of the Craziest Startups of All Time
DJ Miller
9/9/2014
Updated:
4/23/2016

Do you feel like your startup is too crazy of an idea to launch? Well, check out these outrageous startups that chose to dream big on their search for success, but be cautious because not every idea is a great one and will fail if you are not careful and smart.

I Wear Your Shirt 

In 2008 a man named Jason Sadler came up with the idea to launch a company called iwearyourshirt.com. The concept of Sadler’s company is simple; he gets paid to advertise for companies by wearing a t-shirt with their company’s name on it. He also spends time making videos that market your company and places them on YouTube. Little did he know it would become a marketing technique that would catch the eyes of companies worldwide.

His first year in business he earned $70,000, and four years later in 2012 it was reported that he profited $500,000. He now has four other employees that help him with his company. Sadler’s company has advertised for places like Starbucks, Lucky Brand, Pizza Hut, and Nissan. In July of 2012, the company did a relaunch and is still continuing to grow today.

Virgin Airlines 

Ideas for startups are popping up all the time, but I’m sure when Richard Branson brought up his idea to start an airline back in the 80s, people looked at him like he was crazy. Before his airline, Branson was best known for Virgin Records, a record label that signed popular artists like Janet Jackson and Rolling Stones.

In 1984 he announced that in three months a high-quality airline would begin operating. Ten years later, the Virgin Atlantic Airlines had flown over one million passengers. Its secret seems to be that they’re always introducing new things and giving customers more value for their money.

LayoffSpace

In 2007, Jake Ludwinski decided to launch his startup called Layoffspace. This was a website that was meant to serve as a social site such as Facebook, but exclusively for the unemployed. Ludwinski wanted to make it easier for these people to connect in order to find new employment and have a community of people to go through this struggle with. It was free to create a profile on this site and also free for employers to list jobs.

Layoffspace was launched in April of 2007 and failed shortly after. The site is completely dead and no longer has any users. Some think that the problem stemmed from the timing of their launch when unemployment was not very high, or perhaps it was because their target audience was a constantly shifting demographic that people are pretty ashamed to admit they belong to. Startups such as this could have used a business development company that could have taken care of their launch date. People at businesses like Asapy development could have helped with launch dates as well as their specialty which is web development making the user experience friendlier. Possibly instituting a privacy setting which would keep the shame of being unemployed down.

Dropbox

In September of 2008, what is now one of the biggest file sharing sites was launched by founder Drew Houston. Aggravation that came from not being able to access work related files from anywhere was what fueled this idea that struck Houston in 2006. When him and his team first launched, the site was flooded with thousands of users.  

Dropbox’s competitive advantage is said to be that their product functions so seamlessly that competitors have a hard time replicating it. In 2011, iCloud was released and saw no success while Dropbox was still receiving funding all the way into the millions. Their goal as they move into the future is to become the default file system for computers all over the world.

Idea Majesty 

People pay her to teach them how to win. When Carolyn Wilman became unemployed and a mom, she decided to start entering sweepstakes as a new hobby and she experienced an outstanding winning streak. She won three trips in a week. Then she got the idea to share her secret with the world and turn it into a business.

She has titled herself as a promotional marketing consultant, and she shares her expertise with customers through a blog, a newsletter, a weekly radio show, and also a book she has written. Weekly seminars are also given by Wilman, and she charges $100 dollars for every person that attends. She has recently toured the U.S. spreading her winning knowledge and is embarking on a new venture called Idea Majesty in 2014. When you have a crazy idea, getting a patent is important to protect your intellectual property. If you are not sure how to do this, this video on Vimeo will let you know. Patenting your product or idea can protect your idea for years and put an amount of time where competitors cannot infringe on you.

What other crazy startups do you know of? 

DJ Miller is a graduate student at the University of Tampa. He's an avid gadget geek and spends most of his time reading or writing. He is a huge fantasy sports fan and even runs his own advice site for Fantasy Help.
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