You Are Not Going to Believe These Dumb Things that Entrepreneurs Say to Investors



Entrepreneurs work hard for the money and truth be told, many startups don’t raise a dime, with the possible exception of a friends and family round, and would granny every say no to you, no matter that your startup is probably not the next unicorn – or even a my little pony, as Dave McClure calls promising companies that might not grab the big headlines, but are good businesses, nonetheless?

No matter that you believe that you’re changing the world and creating something that no one on planet Earth has ever dreamed possible, trust us, investors have heard it all. In fact, just out of curiosity, we reached out to a few of them and asked them to share with us the dumbest things they’d ever heard out of the mouths of entrepreneurs. Hope you enjoy, and don’t try this at home, much less in front of an investor.

The Dumbest Thing an Entrepreneur Ever Said to Me Was…

‘”We have no competition.”

“What do I have to do to get you to invest?”

“My biggest challenge in my business is working out how to spend all the money these VCs keep throwing at me.”

“Our business model is so unique you have to sign an NDA before we can share any materials.”

“Google can’t do this.”

“An entrepreneurial team that had burned through $100 million of cash tried to convince we why my investing an additional $5m in the company would be a great investment.”

There’s *a lot* of competition for that prize. The one that drove me most nuts was a team that applied to our accelerator, got to the final round, and then told us that there was no way they would ever issue us the equity that we require for them to participate… And then he pitched us on his current round! “Gee, buddy. We don’t ever invest outside of our accelerator but since you wasted all my time, that makes it all good.” before you apply, rtfm.

That he was using his personal money to invest in other startups (instead of his own) to get the attention of an investor running a syndicate.

That she doesn’t get why anyone would build a business focusing on the 40+ demo. (Um, gee, maybe because they actually have money to spend!)

“We plan to go public in two years.”

The Dumbest Pitch I Ever Heard Was…

Stiff competition here. Netflix for neckties is up there. A subscription service for something fewer and fewer people want to wear. Feels like Zipcar for horse carriages.

“I don’t have an MVP, anything built, any commercial partnerships, any staff, a pitch deck or a go to market plan. But I’m raising $1.5m on a pre-money valuation of $5m.”

I plead the 5th … because many great businesses seemed really dumb at inception!

I’ll take the fifth on this one to save the entrepreneur from embarrassment.

‘We’re like Facebook for industrial.’

The dumbest pitch I heard recently was for a video messaging service that enabled users to send very short videos to each other. This was in 2014, when everyone can send video messages with their mobile phones. It was like I had gone back in time.

A balloon bubble that blows up when you fall over and protects your head.

Beauty products that you mix yourself at home (you are sent a handful of ingredients that you can make moisturizer, foundation, and other products out of). Most women barely have time to put on mascara in the morning…

It was a company where you found someone who looked just like you and could almost pass for your twin, and shopped from his or her closet.

A line attached to a boat at the dock that when detached by someone trying to steal your boat sounds an alarm.


Image credit: CC by Alex Proimos

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