He Raised $47 Million To Develop And Operate "Enterprise Web Agents" That Replicate Human Interactions Online
Some founders plan every move years in advance. But Sudheesh Nair, the co-founder and CEO of TinyFish, thrives in the chaos of serendipity, making the right choices with the data at hand, learning quickly, and never looking back.
From growing up in a small Indian town to helping build Nutanix into a $20B public company and leading ThoughtSpot into the AI era, Sudheesh’s journey is a masterclass in courage, clarity, and conviction.
In this exciting interview, he talks about the hype surrounding AI and being calibrated by venture capitalists. He also discusses distinguishing between different pieces of advice and picking the ones that worked well for him.
Growing Up with Simple Joys and Big Lessons
Sudheesh’s story begins in a lower-middle-class family in India in the 1980s and 90s, an era before smartphones, social media, or even cable TV were common. “We didn’t have a lot of money or resources,” he recalls, “But we had family stability, love, great friends, and a good education.”
At that time, they didn’t know anything about the US, except for what they saw on Miami Vice and Baywatch, as he recalls wryly.
Sudheesh credits his upbringing for teaching him a profound truth--happiness often lies in simplicity. “Sometimes we overestimate the power of planning and analysis,” he says. “Then, we miss out on the opportunity that’s right in front of us.” His life has always been about grabbing whatever choices are available.
Sudheesh doesn’t believe in regretting choices even if they go wrong. He’d rather spend time figuring out what went wrong and correcting the error. Those early lessons grounded him, even as serendipity and a well-timed teacher’s recommendation sent his life in an entirely new direction.
The Power of Serendipity and Quick Decisions
While in college, Sudheesh wasn’t even scheduled to attend a certain campus interview. A teacher urged him to go, and he made it just in time. That single decision led him to the US, changing the trajectory of his life.
Sudheesh’s decision-making philosophy would later shape how he built companies, developed and launched products, devised go-to-market strategies, led teams, and even navigated IPOs. All grounded in acting quickly with the info available and conviction rather than waiting for perfect data.
Sudheesh has traveled extensively as part of Nutanix and ThoughtSpot’s worldwide growth. One of the best things that happened to him is the opportunity to travel to almost all the continents and several countries. He firmly believes that every country has something uniquely beautiful about it.
Finding Home in the Bay Area
Today, Sudheesh calls the Bay Area home, not because it’s perfect, but because it celebrates imperfection. “This is one of the few places in the world where failure is not just accepted but valued,” he says. “You can fail and no one holds it against you.”
After traveling to nearly 100 countries, Sudheesh believes human motivations are universal. They are looking for love, safety, and belonging. But what makes Silicon Valley special is its relentless tolerance for reinvention.
Looking back at his life, Sudheesh remarks that he has been in situations that were not the most advantageous for him. But he is grateful for being in a place where failure is just a stepping stone to trying again. “When I land at SFO and drive down Highway 280,” he says, “I feel like I’m driving home.”
Building the Nutanix Story: Competing with Giants
Sudheesh joined Nutanix early, alongside founders Dheeraj Pandey, Mohit Aron, and Ajeet Singh. Together, they built one of the most successful enterprise software companies of the decade, competing head-to-head with giants like VMware.
Sudheesh and the co-founders ultimately took the company public in 2016. It was one of the first tech IPOs of that year. In an uncertain market, deciding whether to take the company public or not was difficult.
But Sudheesh was running go-to-market, and it was clear that customers wanted to see a distinction between private and public companies to invest on a larger scale. Dheeraj and he didn’t stop to analyze things. The decision was right for the employees, investors, and for building lasting value.
For Sudheesh, Nutanix was a story of “fighting out of nothing.” It was a young, fearless team willing to swing at every opportunity. “If you fight like you have a lot to lose, you will lose,” he reflects. “We had nothing to lose, and that made all the difference.”
Two years after the IPO, Nutanix became a $10B business with a $20B+ phenomenal execution story.
Three Core Lessons Learned from Building Nutanix
In retrospect, Sudheesh distills the Nutanix journey into three core lessons:
Pick the biggest bully in the room. “If you’re not competing with a giant, you’re probably not in a meaningful market.” VMware was their giant. · Never underestimate customers. They may not understand every technical detail or stay on top of the curve, but they always know what problem they want solved. Listen to them. Sudheesh also underscores a market reach beyond the US, which undoubtedly is the largest market and home to early adopters. While opportunities are not evenly distributed, talent is. Building the infrastructure, support, and references to take on global competition is crucial. · Filter the noise, “Startups die of indigestion, not starvation. Focus is your sharpest weapon.” At the same time, don’t ignore the signals, but correct course as needed.
Reinventing at ThoughtSpot: From BI to AI
After Nutanix, Sudheesh joined ThoughtSpot. He credits two people with being instrumental in this career trajectory. Ravi Mhatre, the founder of Lightspeed, one of the largest venture capital firms worldwide, is one of them.
The second is Bipul Sinha, who was then also at Lightspeed and is currently the founder and CEO of Rubrik. Ravi was the lead investor of Nutanix and now backed ThoughSpot, a company initially built on the idea of using natural language and AI to deliver Business Intelligence (BI).
One of ThoughtSpot's co-founders, Amit Prakash, came up with the idea of using natural language to deliver data insights to business users. When the company was founded in 2012, data was on-prem, so the system was built on-prem as well.
But by 2018, the world had shifted to the cloud, and ThoughtSpot needed to evolve. Partnering with founders Amit Prakash and Ajeet Singh, Sudheesh helped reboot the company as a cloud-native platform. Around this time, Snowflake was taking off in a big way.
“We essentially restarted ThoughtSpot,” Sudheesh says. “We went from on-prem to the cloud, from BI to AI.” He intended to leverage his go-to-market expertise from Nutanix, which took it to $1B+. Thus, in 2021, Sudheesh and Ajeet partnered to launch the company on Snowflake.
Next, the company launched integrations with Databricks and Google BigQuery just as AI went mainstream. ThoughtSpot became the AI platform for business intelligence (BI), and Sudheesh’s leadership was central to that transformation.
The Emotional Reality of Leadership
When the company needed to restructure from 300 employees to under 100, Sudheesh faced one of leadership’s most complex tests. “You can’t remove emotion,” he says. “Emotions are the reason you do what you do.”
Communicate with extreme clarity. Avoid leaks and uncertainty, and share plans in concentric circles quickly. · Act decisively with defensible logic. “If you claim you overhired, then you failed as a CEO. Be honest.” The framework has to be defensible. · Be fair, not just nice. Layoffs should feel just, not performatively empathetic.
Sudheesh adds, “You don’t want to be liked; you want to be trusted. Do the right thing, and that’s enough.” He accepted that some functions would be affected because the company pivoted. But that did not mean that the people they had hired were not the right people.
The functions were just not necessary. The company was transitioning from on-prem to the cloud and didn’t need on-prem resources to maintain and support it. Sudheesh doesn’t believe in wasting time thinking about mistakes; he believes in looking for ways to rectify them.
TinyFish: Reimagining the Web with AI Agents
Today, Sudheesh is building TinyFish, a company born from the intersection of journalism, browser infrastructure, and AI. By automating research and reasoning, TinyFish dramatically reduces the cost and latency of business intelligence.
Sudheesh’s co-founders included Keith Zhai, a Pulitzer-nominated journalist who worked for the Wall Street Journal, Reuters, and Bloomberg, and Shuhao Zhang, a distributed systems expert from Meta and an expert in browser infrastructure, AI, and ML. The trio brought together worlds that rarely meet.
As Sudheesh explains, “We’re building a platform for operating the web. The browser is where the future battles of AI will be fought.”
In his opinion, the internet is where the freshest data has always originated, just as water comes from streams. But the problem is that the water is not drinkable until you filter it. Similarly, filtering data is expensive and requires processing with ETL systems, data warehouses, and BI tools.
The TinyFish Vision
Asked about the TinyFish vision, Sudheesh says--t o make the web itself operational through AI agents that act, reason, and extract information like humans. These operational agents can ensure that the data is accurate, cost-effective, and can perform complex tasks.
As Sudheesh points out, 60% of knowledge workers’ time in enterprise companies is spent at a significant scale on various tasks. For instance, competitive analysis, pricing, supply chain research, social sentiment, and website data.
People are researching and compiling that data. Some are scraping data from companies that provide it. However, “imagine a million invisible browsers,” Sudheesh explains. “Each researching, engaging, and extracting fresh data for you, like enterprise-grade digital workers.”
Essentially, digital agents can perform tasks that disrupt human workflows in enterprises, like:
Mapping competitor pricing strategies · Assessing credit risk across thousands of candidates · Gathering real-time supply chain data · Conducting fraud detection, as in insurance underwriting · Compiling DNA profiles and other information for clinical research projects
A Business Model Rooted in Enterprise Value
Unlike consumer AI apps chasing virality, TinyFish is laser-focused on enterprise ROI. Companies pay based on usage, the number of agents deployed, and the computational tokens they consume.
“Our model is simple and monetization straightforward,” Sudheesh says. “If we create measurable value, we get a share of it.”
Why AI Isn’t Just a Bubble
Despite the noise around AI hype, Sudheesh believes this moment is as foundational as the Industrial Revolution or the birth of the internet.
As he points out, “The Industrial Revolution unlocked human physical power. The internet unlocked access to knowledge by decoupling it from human domains, and AI unlocks the ability to reason with that knowledge and execute tasks.”
Sudheesh sees the emergence of agentic AI (systems that can think and act autonomously) as the next tectonic shift in human progress. It’s no longer about who has access to knowledge; it’s about who can reason with it and transform it into wisdom.
“Yes, there’s fraud and hype,” Sudheesh admits, “but that doesn’t change the magnitude of what’s happening.” It doesn’t mean that unbelievably value-creating opportunities will not be accessible to companies that are realistic.
Fundraising with Clarity and Discipline
The company has already raised $47M across different tranches, including a Series A round that closed in record time. “We had our first term sheet in less than five days,” Sudheesh recalls. “We knew what kind of investor we wanted and what valuation made sense; we didn’t overthink it.”
Sudheesh emphasized that his team approached fundraising with clarity and discipline. They knew exactly how much they wanted to raise, the investor profile that fit their long-term plan, and the valuation range that made sense without over-rotating on headline price.
For Sudheesh, the quality of an investor outweighs valuation, especially when building a company meant to endure. When ICONIQ’s Amit Agarwal, an operator who spent over a decade at Datadog and served as its president, reached out, the fit was evident.
Sudheesh had long admired ICONIQ’s low-noise, high-value approach. The engagement moved quickly; within hours, they had a rigorous yet fair term sheet. Although multiple firms wanted to lead, the team chose the partner who met their bar without needless back-and-forth.
They closed the round, designed to provide three to four years of runway. Even so, Sudheesh noted the importance of continually building and selectively raising to reset valuation at the right moments. He considers it a fantastic deal for the investors and employees.
Storytelling is everything that Sudheesh Nair was able to master. The key is capturing the essence of what you are doing in 15 to 20 slides. For a winning deck, take a look at the pitch deck template created by Peter Thiel, Silicon Valley legend (see it here) where the most critical slides are highlighted.
Remember to unlock the pitch deck template that founders worldwide are using to raise millions below.
The VC Landscape: Experience vs. Hype
On the broader venture landscape, Sudheesh observed that many founders, especially first-timers, are calibrated poorly by some VCs. Their lack of experience can be confusing, but Gen Z specifically are unbelievably talented when it comes to marketing and creating brands.
Sudheesh draws a distinction between a smaller group of enterprise-savvy institutional investors, who understand the long arc of company-building. These investors are usually in the late-stage growth company sphere but are now entering early-stage sectors.
Sudheesh cited Lightspeed and ICONIQ (now more active at earlier stages), along with firms like Sequoia and a16z, while pointing to standout individuals, such as Vinod Khosla, Ravi Mhatre, and Martin Casado, whose operating judgment he respects.
In Sudheesh’s view, investors who haven’t operated recently or weathered multiple cycles of company building can inadvertently misguide inexperienced founders. This is a newer, louder cohort whose operational depth may be thin.
For those intent on building iconic, long-horizon companies and not just quick wrappers or flips, picking the right person at the early stage matters more than the brand or the platform.
Knowing When to Listen and When Not To
When it comes to advice, Sudheesh uses a simple three-part filter before acting.
First, he examines the speaker’s motivation for advocating a particular view (for example, a booster for a city in which they may also be invested). · Second, he checks whether their experience aligns with the subject they’re pontificating about. · Third, he assumes most advice may not fully apply to his context.
Only after running these checks does Sudheesh parse the content, often finding that a small fraction, such as 7% to 10% or 15% may be valuable, while the majority is not transferable. He appreciates advisors who are explicit about this nuance: what worked for them may or may not work for others.
Sudheesh also reminds founders that they have “backstage access” only to their own company; every other company’s narrative is a stage performance that can look better (or worse) than reality.
Rethinking the Web: From Surface to Depth
Articulating his long-term vision, Sudheesh argued that the web we use today is mainly the surface layer, perhaps 7% to 10% of what exists. For instance, the searches users do on Google and ChatGPT.
The vast 90% majority lives in the deep web, which typical search and LLM interfaces can’t reach. He breaks the inaccessible web into five buckets:
APIs – such as real-time airline pricing. · Logins – social platforms and paywalled media. Most of the new data is created behind logins on platforms like the New York Times, Medium, and Substack, among others. · Workflows – task-specific forms like booking appointments. · JavaScript-driven personalization – where each user sees something different. That’s because retargeting and cookies determine what the website should look for in the user, rather than the other way around. · The Long Tail of the Internet – valuable results buried far beyond page one.
Sudheesh’s ambition is to make 100% of the web outcome-accessible through agentic AI or systems that can reason, log in, execute workflows, handle personalization, and traverse deep content at scale.
The TinyFish Vision: Outcome-Driven Discovery
Sudheesh’s vision underpins TinyFish. Rather than relying on search (being lost) or browsing (wandering), TinyFish dispatches goal-driven web agents that pursue explicit outcomes.
They can log in, execute a workflow, click at scale, and run JavaScript. These agents can search a website like a human and examine what a machine does.
Sudheesh illustrated the difference with a concrete example: instead of showing a generic first-page list of coffee brands, an agent can dig through dozens of pages to surface a small, ethical Nicaraguan family farm that perfectly matches a buyer’s intent.
Sudheesh pointed to a live case in hospitality: TinyFish has helped surface thousands of small Japanese hotels on Google Hotels—complete with price and inventory—amplifying the “tiny fish” of the internet that otherwise remain invisible.
For Sudheesh, that is the point: shift the web from intermediary-driven discovery to outcome-driven access.
The Final Lesson: Keep Your Head Down and Build
For all his success, Sudheesh remains grounded in humility and execution. “Who you hire, who you raise money from, how you set goals, those fundamentals haven’t changed,” he says. “Ignore the noise. Focus on creating real value. That’s how you build something that lasts.”
Sudheesh closes with a builder’s mindset. The company is just over a year old, and the team is moving fast, grateful to be operating at the crest of a generational wave.
The mandate, as he frames it, is to imagine what seems impossible and to inspire customers with outcomes—rather than simply trying to sell them.
From a small village in India to the epicenter of the AI revolution, Sudheesh Nair’s journey is proof that opportunity doesn’t always arrive planned; it often just shows up, waiting for someone brave enough to say yes.
Sudheesh Nair’s journey from a small Indian town to leading billion-dollar companies shows the power of clarity, conviction, and adaptability in entrepreneurship. · His decision-making philosophy—acting quickly with available data rather than waiting for perfect information—became the cornerstone of his leadership style. · At Nutanix, Sudheesh learned to “pick the biggest bully,” listen deeply to customers, and stay laser-focused amid noise, scaling it to a $20B public company. · At ThoughtSpot, he led a bold pivot from on-prem BI to cloud-native AI analytics, demonstrating how reinvention fuels longevity in tech. · With TinyFish, Sudheesh is reimagining the web through enterprise-grade AI agents that operate online like human researchers, automating reasoning and discovery. · His disciplined fundraising approach—prioritizing investor quality over valuation—reflects a builder’s mindset focused on endurance rather than hype. · Sudheesh believes AI’s rise rivals the Industrial Revolution, unlocking reasoning power at scale, and reminds founders to ignore the noise and build enduring value.
Original Version
Alejandro Cremades: Alrighty, hello everyone and welcome to the DealMaker Show. So today we have an amazing, amazing guest, you know, I guess that has seen, you know, quite a bit, you know, when it comes to ah the startup world. And, they you know, we've actually had a bunch of um people that they have been in some of the companies that he has also been involved with, but now he's at it, you know, he's saying really doing it, you know, with his own company. We're going to be talking about the building, the scaling, the financing, also, you know,
Alejandro Cremades: you know Whether there is hype or not in this AI you know world right now, we're going to be digging into that as well as how to be calibrated by VCs, also how to listen or how not to listen you know for the right advice, and many other things that I think are going to make the episode day right now super exciting. So without further ado, let's welcome our guest today, Sudish Nair. Welcome to the show.
Sudheesh Nair: Alejandro, thank you so much. love your radio voice. you were We were speaking normal voice and then the recording stopped and started and suddenly the radio voice comes out.
Alejandro Cremades: There we go. There we go. Ready for action. So, Sudish, in your case, you know, give us a walk through memory lane. How was life growing up there in India?
Sudheesh Nair: It was good. Look, I think sometimes we overestimate what it takes to be happy. I kind of feel like we are all, the water level keep racing and what it takes to make us happy keeps going up.
Sudheesh Nair: but I grew up in a very normal lower middle class family didn't have a lot of money or resources, but a very stable family, loving parents, a brother that sometimes I love sometimes we used to fight ah phenomenal friends and good education.
Sudheesh Nair: No real adversity, obviously. You know, growing up in the 80s and 90s in India, it's nothing like the India of today. um TVs and all of those things, ah the resources, luxury, social media, none of those existed. us was Honestly, US was nothing but, I think it was probably Miami-wise and soon after that, maybe Baywatch.
Alejandro Cremades: Now, in your case with this, it sounds like a serendipity has been ah a big one. ah And when you were there in India, there was one of the teachers that they that you really had a ah connection with.
Alejandro Cremades: And eventually, our recommendation to take an interview changed the course of everything. So tell us about this.
Sudheesh Nair: Yeah, Alejandro, I think sometimes, you know, we overestimate the power of planning and analysis and then miss out, like, really the opportunity that's in front of us.
Sudheesh Nair: My life has always been about taking the choice right in front of us. If there is an A-B fork, I'm really good at taking on the fork that I think is the best with the given data that I have.
Sudheesh Nair: And the the only thing that comes out part of the package is that you have to make sure that you don't regret the fork you took. And also make sure that if it is a wrong fork, you don't spend too much time thinking about why it was wrong, but spend ah just enough time to figure out what went wrong and then correct So going back to the story, when I was in college, you know there was a campus interview happening that was not for the sessions that I was taking, but there was a teacher who said, you should go talk to this company.
Sudheesh Nair: And ah she missed me by, let's say, five minutes. I would not have taken that road. And that road led me to the US. And I can tell you so many stories were the ability to sort of make quick decisions with the the most amount of analysis that you can do with given data has helped me.
Sudheesh Nair: And to date, when it comes to company building, whether it is product or engineering or go to market, I often prefer decisions made with the the data that is present in versus waiting too long for all the pieces to come together.
Sudheesh Nair: And today with AI, it has become a necessity as well.
Alejandro Cremades: A thousand percent. So tell us about coming to the U.S. because obviously the U.S. you know has been pivotal in your career.
Sudheesh Nair: Yeah. I think, I don't know, um for me, I've traveled a lot, Alejandro, as part of you know both Nutanix and ThoughtSpot growth, worldwide growth.
Sudheesh Nair: And one of the best things that happened for me is the opportunity to travel to pretty much all continents and a lot of countries. I would say still maybe 100 countries I haven't visited, but probably covered most of the others.
Sudheesh Nair: And sometimes people ask, which country is best and I honestly don't have an answer. Every country has something unique that is beautiful about them.
Sudheesh Nair: At the core of it, I found that every people are same. They're all looking for safety, love and belonging. US, particularly Bay Area, and I've spent most of my adult life in the Bay Area, so it is a bubble. I'm very aware of it.
Sudheesh Nair: Within the bubble of Bay Area, I found home and because it is one of those places where Two things that I value were cherished. First is, this is a place where people not just appreciate, but to value failures.
Sudheesh Nair: They can log in, they can execute a workflow, they can click, click, click at massive scale, execute, ah, ah, JavaScript-based execution, or they can look at a website like a human does, or it can look at what a machine does.
Sudheesh Nair: If you send it out, it will not just be in the surface, it go deep. And then it stops doing searching and browsing, because think of searching. Searching is like when you're lost.
Sudheesh Nair: Doesn't it, like, outside the context? When you search, it means you're lost. Browsing means you don't know what you want, you're just wandering. What if you have an intentful, goal-driven group of agents that is going and getting you exactly that?
Sudheesh Nair: Next time, when I say, I want this organically grown ethical coffee from Nicaragua, instead of searching and showing up the first 10 items that's all Starbucks and big chains, what if our agent can go to the 50th page, look at everything, and then find that one small, small family farm that's been growing coffee for the last four generations, and surface it to me and say, I think this is the one you should go to.
Sudheesh Nair: When you go to tinyfish.ai website, we are highlighting the story of an eight-room hotel that we have surfaced on Google Hotels. Google is our client.
Sudheesh Nair: We have thousands and thousands of small hotel hotels all over Japan. They are surfaced on Google hot Hotels with price and inventory that they just couldn't have done before. Very fulfilling.
Sudheesh Nair: We want to make the world more outcome driven as opposed to intermediated for commercial exploitation that Google and Chagipita and others are going to build for.
Alejandro Cremades: I love it. So Sudish, for the people that are listening to us now that would love to reach out and say hi and perhaps, you know, learn more about tiny fish, what is the best way for them to do so?
Sudheesh Nair: Go to www.tinyfish.ai and reach out to us and try it. You know, talk to some of our clients and, you know, give us some feedback. We're just a year-old company, little over a year-old company. There's a long ways to go, but the speed with which we are innovating, it is… it's a bright new world out there. Think big.
Sudheesh Nair: I think an opportunity like this, when the wave is cresting, we just so happen to be so grateful that we have opportunity here. This is the time to imagine impossible things and inspire customers, not sell.
Alejandro Cremades: Amazing. Well, Sudish, thank you so much for being on the Dealmaker Show today. It has been an absolute honor to have you with us.
Sudheesh Nair: Alejandro, you are so nice to talk to you. And it's… it's fantastic. I love the way you set up these interviews and carry forward amazing conversation. Thanks a lot.
