Shashij Gupta

You absolutely need to hear about Shashij Gupta – the dude’s the real deal in AI and startups right now. So, he’s a YC F24 guy, but his process is pretty wild. Started out with a solid background in computer science at IIT Bombay – that’s like the top tier in India – and from there, he jumped into some serious research and industry gigs.

Before jumping into founding Cekura, he was doing NLP research at Google, which is no joke. His paper on testing transformers has been cited over 50 times – that’s legit recognition in AI circles. Plus, he’s got experience in quantitative research at a trading firm, so he’s no stranger to crunching numbers and making sense of complex data. Basically, this guy’s been deep in the trenches of AI and finance, understanding how systems fail and how to make them better.

Then, he co-founded Cekura (which was originally called Vocera until March 2025). The company is backed by YC, raised $2.4 million in seed funding – which is a big win – and is all about making conversational AI super reliable, especially in industries where mistakes can cost lives or serious cash, like healthcare, banking, logistics, and retail.

The tech is sick – they simulate thousands of fake calls and chats to stress-test AI assistants, so companies can find and fix those annoying edge-case failures before they go live. It’s basically like giving AI agents a tough exam so they don’t screw up when real users are talking. That’s super critical when you’re dealing with sensitive stuff or massive scale.

What’s crazy is how his past shows what kind of guy he is. He’s all about making AI safer and more reliable, not just for the hype but because he truly understands the impact of bad AI in real life. His background in research, finance, and now startup world screams that he’s motivated by solving real problems, not just chasing shiny tech. He’s the kind of founder who’s been deep in the trenches, understands the messiness of AI, and jumped into this startup to fix it.

So yeah, Shashij’s the kind of guy who’s crushed it in research, jumped into startups, and now is building something that could change how AI is used in critical industries. Definitely a name to watch.