Real Life Shark Tank: 12 of the Strangest Things I’ve Been Pitched

Throughout my time as a seed and accelerator investor at 500 Startups and my angel investing on AngelList via my syndicate, I’ve guided money in the direction of 174 startups for a total of $23M in venture capital.

Along the way I’ve seen and heard some strange things that I can’t unsee, unhear, or cover up with my Pokemon addiction.

Here are those stories…

#1 — Butt Mask

Two Taiwanese men call me on Skype to video chat. One holds up pieces of paper from a printed Powerpoint slide deck. The other begins opening a package, removing a white, wet-looking facial mask item. He says nothing. He begins applying it to the naked butt of a male mannequin. If it wasn’t for doing pre-meeting research and knowing that this was a gay men’s beauty company, I would have thought I logged onto the wrong video chat. Instead I thought this was one of the most well-formed and entertaining pitches I’ve ever seen.

Not only did I find a Unicorn to invest in. I also will now have a perfectly formed buttocks.


#2 — Smoke Weed with Lasers

About a year ago I was offered to smoke a weed vaporizer in a pitch meeting in San Francisco. The room was filled with two suits and a hacker. The cannabis was heated and vaporized by an actual laser. Like the type of laser that you point at something and it almost instantly starts making it smoke and start on fire. Afterwards, I realized I may have accidentally knocked out Goldeneye.


#3— Pickleman

During 500 Startups accelerator interviews, I was approached by a man in a pickle outfit. I thought he was from Claussen. He was there to pitch me his business.

It was actually a solid, profitable business by Russ Perry named Design Pickle, and I really enjoyed meeting the founder. He found a way to stand out, and, as a good San Franciscan, I’ll always respect a human in costume.


#4 — “Lets Measure Dicks”

This pitch was a cold email to my entire investment firm and is about a site that aggregates “the first successful consumer internet aggregator including all social networks.” It inspired me to write a poem:

Here is the church
Here is the steeple
Open your email
And measure the people


#5— The Doodle Bra

“Express yourself and have fun” is the tagline of the Doodle Bra pitch I saw a few months ago vying to get into an accelerator program. How’d they know my life motto? The Doodle Bra is simple, but genius. It’s a bra you can draw on.

I also like the swag…


#6 — Hug Button

This company has a product that looks like a button. You wear it, and when it comes in contact with another person also wearing a button, an action happens. An example the founders gave was ordering a pizza.

I can’t wait to hug Sheel Mohnot to thank him for sharing this pitch.


#7 — Shock Your Bad Habits Away

The Pavlok shocks you when you are doing your bad habits. I tried it and found it unreasonable to shock myself every five minutes (and that I have an unreasonable amount of habits), so I kept my collection of bad habits, but if you focus on one bad habit — think smoking, sugar, biting your nails — it seems to actually work.


#8 — An App for Escaping People

TIYO (This is Your Out) is a keychain piece of hardware that has a single button. That button calls your phone and gives you line-by-line scripted advice on how to get out of your bad date, sales meeting, and just about anything.

Thanks to Neha Khera for this one. And to Chelsea Handler for this.


#9 — Sex Auctioning

Sex Auctioning — Please, read the entire product description, but here it is in short:

“The product is aimed at getting organized users sex.
This is extremely hard for any men, and most do not get laid by 25, with their desired mates. Women have an easier time, but are often coerced and drunk, or go out with the wrong guy, because of emotions and hormonal manipulation.”

Also from this founder: Smokey Rooms, which explains that ‘colleges smoke weed but not in an effective way.’ I agree to disagree.


#10 — Nipple

Nipple — wants you to “compare [sexual] performances through fancy datas (sp), diagrams & tables…” I especially like that the data is fancy, because I’ve also been studying tantric meditation.


#11 — Sticky Rice Love

Sticky Rice Love was explained to me in the following words: “We hope to develop some interactive bottom-up online courses…” I’m not going to ask what they mean by ‘bottom-up,’ or ‘sticky rice love’ for that matter.


#12 — Airbnb Meets Dating — They explain themselves as “an AIRBNB for worldwide Win-Win dating. We find you EXACTLY what you want.” Stephen Barr seems intrigued and comments ‘Interesting concept’ on their profile. Maybe it was the comparison to Airbnb that drew his attention, but why they didn’t choose Uber to compare to we’ll never know.

Bonus points that the founder describes himself as, “A Win-Win guy. Founder of PsyClue, an app that teaches to think Win-Win and DoGoodity.” I’m sure it was his Yale and Columbia education that helps him think ‘Win-Win.’


Parting Thoughts

Don’t get me wrong. In my opinion, weird ideas are what makes this world interesting. I am supportive of anyone who follows their passion and I wish the above entrepreneurs nothing but the best in their endeavors. It’s just that some ideas aren’t for everyone. Especially when it involves forking over tens of thousands (or millions) of dollars.