Karan M Gupta

I build companies that connect people. Three messaging startups, two acquired, two Nasdaq IPOs, and five years on PlayStation. Now CEO of Voicebox.ai. San Francisco and Seattle.

Karan M Gupta seated on a boulder in Peru, mountains and ancient stone terraces behind him
2 IPOs
2 exits
AnchorList 2021 Top Startup CTOs
Two Nasdaq listings: The RealReal team celebrating on IPO day, and the Shift ticker SFT on the Nasdaq tower in Times Square
The RealReal on Nasdaq. Shift on the Nasdaq tower.

Background is in AI and Robotics. Started my career in Reinforcement Learning research, built the fastest line-following robot, and worked on a project for NASA's Mars missions. Right around this time I was accepted into Mensa.

My first company was Heylos, a social shopping co-browsing messenger. That's what took me into Sony PlayStation.

I went on to found Mammoth, a team messaging startup (pre-Slack) with users in 80 countries, inducted into AngelPad, and acquired. There I designed the first magic-link, password-less login flow we find everywhere today.

Then two Nasdaq IPOs, first at The RealReal and next as CTO of Shift. Then briefly CTO at LeafLink.

I was ready to start building my next company. I had been tinkering with voice AI and UIs for years. I founded Alice, the world's most confidential AI recorder, used by journalists worldwide.

Now, Voicebox. Every company has a web address and an email address. Voicebox gives it a voice address. Tap and talk.


I am a TiE Charter Member and spend time with entrepreneurs and investors where I can be helpful. I regularly appear on podcasts and articles.

I play guitar on stage occasionally, and love motorcycles and travel.