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This Gen Z entrepreneur is pitching hundreds of investors through Venmo – Technology Flow

My phone rings when I get a text from a friend who is a partner at a VC firm. This is a screenshot of the Venmo notification that just arrived. “My 2 cents on why you should invest in my company,” reads the message she received along with the $0.02 transfer. I tracked down and emailed the founder who sent the transfer to figure out what they were doing.

“In the last two and a half weeks I’ve reached out to over a hundred VCs, angels, celebrities, athletes and influencers through Venmo,” said Chip Herndon, CEO and co-founder at Chatterbox in an interview with Technology Flow. He claimed that his unusual marketing campaign was very successful. “I received multiple responses, two of which were of exceptionally high quality. The first is the partner [a venture firm]Another is an angel investor.”

Herndon said those messages were the start of a string of meetings that could lead to the investment.

Chatterbox is a platform that describes itself as Nextdoor for Gen Z. It connects young people in their local communities through a medium they understand — group chats.

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Screenshot from Chatterbox website. Image credit: chatter.

“In our initial phase we targeted college campuses. We have three main features: user generated chats, emergency chats and permanent chats. For example, we will start this October at UCLA in partnership with the president of USAC,” noted Herndon. “As part of the MVP we will have permanent chats for every dorm building, library and other high-user-density locations; We also allow users to generate chats for interesting events they encounter and finally we automatically generate chats for emergency situations.

The founder says the Venmo-fueled outreach campaign stemmed from a desire to get noticed in a fiercely competitive landscape.

“I had to get scrappy. I set aside four hours with a pen and a piece of paper in front of me, not allowing myself to do anything but brainstorm until I had a strategy,” Herndon says. I decided Venmo was best.”

Using the Venmo platform’s search and profile pictures features, he sets out to find the investors he’s looking for, and he notes that it allows him to “grab their attention in a way that doesn’t feel intrusive.”

Not all investors agree on that particular point. “It feels a little creepy,” noted one investor who received one of the Venmo transfers.

But that may not be the case for everyone.

An associate at another venture fund I spoke to for this story said, “You have to do what you can to stand out,” and for a moment seemed impressed with creativity. “Would I love to receive a ton of $0.02 donations with a bunch of random pitches for startups? No, but the first one or two are enough for me to care.

Kudos for trying something new, I suppose, but remember that gimmicks often backfire.

So, is this the next big way to reach investors? Personally, it looks pretty spammy. Let’s put it this way: the first PR person who tries to pitch me a story via Venmo will be banned and blacklisted; Finding my email address is easy, and in my opinion, trying to navigate around the available channels to get yourself to the top of the list seems like a hassle. However, I’m a bit OldManYellsAtCloud.gif about these things; Your mileage may vary. Be aware of the first impression you are making; It may not be as positive as you think.

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