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10 extreme things entrepreneurs have done during a pitch competition


Entrepreneurs are, by nature, risk-takers. This quality can serve as an advantage during a startup pitch competition, but it can also go terribly wrong.

Curious about what kinds of risks pay off — especially when funding is at stake — I asked 10 entrepreneurs from the Young Entrepreneur Council about the craziest things they have done to get investors’ attention.

Their best answers are below.

I said we were raising just the cost of a lunch to meet with me
I got up on stage and crushed our pitch. People loved it. At the very end, I said we were raising $18.33, what a lunch would cost to meet with me.John Rampton

This was a gutsy move but we ended up getting over 30 contacts from investors taking me up on my lunch. Every one of them referenced the amount in their email or in-person conversations. It’s something different that stuck out in their minds.

Investors don’t care what you’re trying to raise when they are first getting to know you. They want to know you. Do something that’ll stick out in their minds. – John Rampton, Due

I gave away free massages
We were trying to think of a creative way to make my insurance startup, Margo, get noticed at a startup expo.Zach Robbins

We tossed around the idea of free food or drinks instead of the usual throwaway swag, but we wanted to be sure whatever concept we went with tied back to our business. Our value proposition is that we make it easier to shop for, save on, and manage your insurance. More or less, we take the pain out of insurance.

What else takes away pain? Massages. So we decided to hire two chair masseuses to give away free massages to attendees. It drew a ton of people to our table, and we were able to pitch them our concept while they waited in line for our masseuses. – Zach Robbins, Leadnomics

I closed a round on my wedding day
We were closing our VC round and I had one last investor to present to finish everything.James McDonough

I pitched on my wedding day hours before the wedding started via my Thailand destination wedding hotel room.

We closed the round and I am now happily married to both my wife and investors. – James McDonough, SEE Forge creators of FAT FINGER

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