My guest is Sudheesh Nair, co-founder and CEO of Tinyfish. He has done this before. Early at Nutanix through IPO. Then six years running ThoughtSpot. He left both without drama. Not because of ego or boredom. Because the rooms filled with the same talks about price and discount. Because he wanted to build again, from first principles, and be accountable as the one in the chair.

Tinyfish is an AI shop by label, but the pitch is plain. Make the web act like a person with a browser, at scale, and do work that matters to a customer. Do not sell buzzwords. Sell outcomes. On their site the story is a small hotel in rural Japan, eight rooms, not wired into any fancy API. An agent signs in like a human, checks dates and room types, reads the price and availability, and updates Google Hotels so the listing shows live numbers, not “call for rate.” The hotel changes nothing. Google shows richer results. A traveler gets a real choice. That is the point. Not the model size. Not the paper count. A change you can see.

We talked about leaving public companies. He said it straight. Loyalty is not a slogan. A company is a set of contracts, with investors, customers, and employees. You should fight for the mission while you are in the seat. You should also remember who picks you up when you fall. Family. We forget that when things go well. We dump on them when things go bad. If you want to build a place worth working at, draw clean lines, hold purpose and professionalism together, and be all in, until you are not.

What drives him now is less shine, more fit. Call it Ikigai if you like. What you are good at. What pays. What the world needs. Cut the romance. Cut the cosplay. Be honest about your limits. Then pick the work where your strengths meet a real need, and grow the pie so others win with you.

We also covered the noise around AI. Every site sings the same chorus. He refuses to sell that. The team tells a clear story instead. His co-founders make sense of that stance. Keith was a Wall Street Journal and Bloomberg reporter, Pulitzer finalist on Hong Kong. Shu Hao is a deep browser thinker. One believes in lowering barriers to information. The other believes the browser can be a bridge, not a wall. Sudheesh comes from analytics and knows this truth, fresh data starts on the open web, but most stacks mangle it before it’s useful. So they send agents to do the reading, sort the signal, and return only what helps. Less plumbing. More proof.

Under it all sits a worry I share. We moved from blue links to feeds to one answer in a chat box. Power pools at the top. If we let that stand, the best coffee or the best small hotel stays invisible, not for lack of quality, but for lack of API glue and ad spend. An outcome-first web is one answer. Do the task. Show the result. Lift the tiny fish, not only the whales.

Hire for that mindset. He likes journalists for a reason. Curiosity. Hard questions. Pattern sense. In a field this young, certainty is a tell. The honest posture is study and ship.

If you want to see the idea land, go to tinyfish.ai and look at the hotel case. Eight rooms, now visible. Simple, not easy. The kind of fix that bends the web a little closer to fair.