Strange Startups and Eccentric Entrepreneurs

Having doubts about the audacity of your latest business proposal? Searching for inspiration for the next great startup idea? Bored? We’ve compiled a list of the zaniest startup ideas for your entertainment, affirmation, or inspiration. Hey, you never know.

Secret Genius


What: Funding specifically for artistic projects, such as an album, book, or theatre production.
Why: Kickstarter is an artist for artist funding platform. The site allows artists to advertise your art project to the Kickstarter community for peer backing and support with pledges starting at a minimum of $1.
Yay or Nay: Hells Yay. There is not enough support for struggling artists to make their mark. Kickstarter is the silent middleman that links the creative with the financially blessed. It’s the AngelList of the artist world.


What: “The car wash that comes to you!”
Why: Have your car washed at your convenience and on your time, any time.
Yay or Nay: Yay. A convenience that at first seems more luxury than necessity until you experience the lineups at the car wash – then Cherry starts to look pretty clever.

What: Rentable cardboard moving box supplier.
Why: Founder Marty Metro started selling used cardboard boxes in his neighbourhood as an experiment…and the business took off!
Yay or Nay: Yay. Have you ever been the victim of the moving box crisis? At the eleventh hour of a move when all of your belongings are gathered and sorted, cardboard boxes suddenly seem to disappear from the face of the earth. may seem superfluous at first…until you have to move.



What: Purveyors of the infamous Christmas sweater, most famously the men’s “tacky” Christmas sweater.
Why: Founder John Kaplar’s love for men’s festive sweaters continually went fulfilled. He could only ever find women’s Christmas sweaters (what is that telling you, John?), so he was forced to take matters into his own hands.
Yay or Nay: Nay. Why is anyone encouraging one of Christmas’ most dreaded gifts?

What: A dating website based on appearances (member hopefuls must be voted in).
Why: In their own words: “Dedicated to ensuring members find their perfect match.”
Yay or Nay: Nay. Not only is this site designed to promote discrimination based on appearance, but who knows how many “attractive” egos this site is boosting?

Whatever Happened To…?

What: Said to be the Yelp for professional people, the site allows individuals to anonymously critique the performance of anyone listed on the site.
Why: For (potentially brutal) honest second-hand assessments of professionals everywhere. No one is safe.
Yay or Nay: Nay. No filter could easily lead to a haven for hatred and unfair judgments. Clearly the same sentiment was felt by the founders who scrapped Honestly and have now created TalentBin, a search engine for employers to seek out professional talent – a much more productive approach.

That Worked?!

What: Staff of this website will wear a company’s t-shirt and create promotional videos for one day only.
Why: The site creates an outlet designed to promote companies in a unique way utilizing the popularity of social media.
Yay or Nay: Yay. Seems like too simple an idea at first, but the marketing scheme not only takes a new approach to company promotion, it acts as a company database for consumers.  


What: A man who either really loves kids, or really, really loves Christmas, got a legitimate address in the North Pole where hundreds of thousands of children send their Christmas wish lists to “Santa” each year and to whom founder, Byron Reese, replies. For $10 a letter.
Why: To bring joy to children everywhere…and make their parents pay for it.
Yay or Nay: Yay. It is a solid, viable business model as seasons of success have proven. Except when children eventually find out that there is no Santa Claus, at what point do parents reveal to them that the person who has been responding to their Christmas letters throughout childhood is a strange man from Texas?