Many businesses around the world use consumer-facing chat apps like WhatsApp, Telegram, Discord, or iMessage to talk and coordinate with staff, and exchange documents or data.

Guy Weiss is building Zenzap, a private messenger with AI that wants to help companies communicate with their staff and arm them with their organization’s context while staying in line with IT and security rules.

The company has raised $44 million in funding from investors including Bessemer, Lightspeed, and The Garage, as well as individual investors Wix president Nir Zohar and former GM of EY, Yoram Tietz.

The fundraise is interesting because Weiss is raising money for the first time in his career. In 2012, he bootstrapped e-commerce marketing platform StuccoMedia, and sold it to Market Group in 2015. After that, he became an investor for a few years. In 2022, he founded Zenzap after meeting Bessemer partner Adam Fisher and noodling on different ideas along with his current co-founders Noam Neumann and Jonatan Bien.

Weiss said he initially bootstrapped the app and worked out of Bessemer’s office.

“I didn’t want to raise capital. The only thing I had to lose was my name, and I was super afraid to do a second round as a founder and become a failure, because my first round was very successful. I didn’t need to work for money. So, when I met Adam, I actually started my idea with my own capital,” he told TechCrunch.

Weiss said Fisher convinced him that Zenzap should be a venture-backed business, as the company would need capital to scale.

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