In February 2017, a travel startup called Stayzilla collapsed in Bangalore. Most of its engineers updated their LinkedIn profiles and started fielding recruiter calls. Pankaj Gupta did something different. He gathered seven of them, promised uninterrupted salaries, and told them he had no idea yet what they would build. That not-knowing lasted about three months. What came out of it - a small AI lab called Halli Labs - was acquired by Google before the year was out. It became Google's first-ever acquisition in India.
That episode is not unusual for Gupta. It is, in fact, the pattern. He moves toward the edge of a platform shift - earlier than most, with more conviction than is comfortable - builds something, hands it off, and moves again. Sahasra Networks (acquired by Cypress). Phulki, a music search startup (acquired by Saavn). Halli Labs (acquired by Google four months after founding). And most recently, Yupp, an AI model evaluation platform backed by a16z with $33 million in seed funding, which Gupta co-founded in 2024 and shut down in March 2026.
The shutdown is the most recent chapter, and the most instructive. Yupp had 1.3 million users. It was comparing outputs from over 800 AI models. It had backing from Jeff Dean, Biz Stone, Evan Sharp, and Aravind Srinivas. And Gupta walked away from it, publicly, with an honest post-mortem that did not blame the market, the investors, or bad luck. "The AI model capability landscape has changed dramatically in the last year alone and will continue to change quickly," he wrote. "The future is not just models but agentic systems."
The AI model capability landscape has changed dramatically in the last year alone and will continue to change quickly. The future is not just models but agentic systems.- Pankaj Gupta, on shutting down Yupp (March 2026)
That sentence is worth sitting with. Yupp's entire premise - that crowdsourced human feedback would be the engine powering AI model improvement - was disrupted not by a competitor but by the speed of the technology itself. Models got good enough, fast enough, that the kind of broad preference data Yupp was generating became less urgently necessary. The industry shifted toward agentic systems that self-improve with minimal human intervention. Gupta saw it clearly, said so plainly, and moved on.
That clarity is a throughline. At Twitter, where he was one of the first 30 employees, Gupta built Who-to-Follow - the recommendation system that made millions of new user connections daily and was foundational to Twitter's growth in its critical early years. He also built Tweepcred, a graph-based reputation system, and invented MagicRecs, the push notification feature that surfaced relevant content from a user's social graph in real time. He co-authored the academic paper on WTF (Who to Follow) that became a widely cited reference in social graph research.
He left Twitter in 2014. He moved to Bangalore in 2016 - a deliberate choice, not an accident - joined Stayzilla as Chief Product Officer, watched it collapse, assembled a team from the ruins, and built something Google wanted in four months. That something, Halli Labs, aimed to apply modern AI and machine learning to "old problems" for the next billion users. It was the right idea at the right time, pitched to the right person: Caesar Sengupta, who was running Google's Next Billion Users initiative and had been trying to recruit Gupta anyway.
At Google, Gupta led the engineering team that launched Google Tez (now Google Pay) across India and APAC - one of the fastest-growing payments apps in history. He then expanded to lead Google Pay Consumer engineering globally. In April 2021, Coinbase hired him to build its India operations from zero, making him the first employee and site lead for what was intended to become a full tech hub. Within the same year, Coinbase acquired Agara - the AI startup Gupta had co-founded but left when Google recruited him - reuniting him with colleagues across company lines. He recused himself from the acquisition evaluation to avoid any conflict of interest, a detail that tells you something about how he operates.
He left Coinbase in 2024 and co-founded Yupp with Gilad Mishne, drawing a team from Coinbase, Google, X, and top research labs. The pitch: gamify human feedback to improve AI models, use blockchain for transparent, immutable evaluation records, and build the definitive leaderboard for AI performance - the Yupp VIBE Score (Vibe Intelligence Benchmark). At its peak, the platform hosted over 800 models and collected millions of user preferences monthly.
The a16z bet, led by Chris Dixon, alongside 45 angel investors, said something about the credibility Gupta had accumulated. Google's Jeff Dean invested. So did Biz Stone, who had watched Gupta build the recommendation system that helped Twitter find its footing. Evan Sharp (Pinterest co-founder) and Perplexity CEO Aravind Srinivas were in too. That is not a list that assembles for a weak pitch or an unknown founder.
What comes next is an open question. Gupta's track record suggests he is already thinking about it - probably has been for a while. His instinct has consistently been to move toward the frontier before the frontier has a name. Agentic AI systems, he has said, are where the next wave is breaking. If the pattern holds, he will be building something there before most people finish reading about it.