Category: Podcast Episode Transcript

Full transcripts of the Startup Project podcasts.

  • Revolutionizing Workflows with AI Agents: Jacob Bank, CEO of Relay

    In this conversation, Nataraj sits down with Jacob Bank, the founder and CEO of Relay, a startup building AI agents to revolutionize how we work. With a rich background in AI and productivity from his time at Google and as the founder of Timeful (acquired by Google), Jacob offers a unique perspective on the intersection of automation and artificial intelligence. He shares the winding journey of Relay, from its initial concept as a cross-product collaboration tool to its current form as a powerful AI agent platform. Jacob dives deep into the challenges of building in a rapidly evolving market, the importance of robust integrations, and the product-led growth strategies—particularly his success on LinkedIn—that have propelled Relay to early product-market fit. This discussion is a masterclass in modern company-building, navigating the AI landscape, and understanding the future of automated workflows.

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    Nataraj: What is Relay and how did it get started?

    Jacob Bank: Relay.app is a platform to build AI agents. The journey has been a bit winding to get here. I started the company in 2021. My background is in academic research in AI and then building productivity tools. When I started the company in 2021, we had two founding premises. The first was that we all use a lot of tools to get our work done. The builders of those individual tools spend a lot of time figuring out how to make experiences within those tools better, but probably not enough time figuring out how those tools interact with the others in your ecosystem. For example, I used to be the product lead for Gmail and we would agonize about every single pixel when you were archiving, replying to, or starting an email. But if you said, ‘Hey, I really need to get data out of Gmail into Notion and then also Salesforce and then send a Slack message,’ we’d say, ‘Sorry, good luck. Use the API.’ When we looked at what knowledge workers are actually doing, a lot of what we do is take stuff from one tool, do some stuff with it, and then stick it in another tool. We thought there was an opportunity where people were underestimating the importance of cross-tool coordination. And second, it sounds so silly to say this now, but it was not obvious in the summer of 2021 that AI was going to be important in doing this. The original name of the company was Collab AI, and we didn’t know exactly what product we wanted to build, just that it was going to help with cross-product workflows and that it was going to use AI somehow to do that.

    For the first year and a half of the company, we wandered in the desert, as they say. We built eight or nine different product prototypes that all fit that theme, but none were quite right. We built an automated to-do list, a contextual knowledge base, a stand-up tool, and an employee onboarding tool. Eventually, we landed on a workflow tool. A workflow tool that captured repeated tasks that had an element that can be automated and an element that required human judgment. That’s why we named the company Relay, because we were thinking so many things we do should be a relay race where the computer does some stuff and the user does some stuff. We announced our beta at the end of 2022 and ran it in 2023. By the end of the beta, we realized that maybe there was a category to be created there, but it wasn’t us who was going to create it. It just wasn’t right. When you’re an entrepreneur and you’re just muscling something through that’s fundamentally not right, there’s too much friction.

    So in the summer of 2023, we decided we were going to build an automation tool. We would focus on the market that Zapier is the leader in: cross-product horizontal workflow automation for a non-technical audience. But we were going to try to build the modern version of it. What makes it modern is that it’s way easier to use for non-technical people, it has AI better integrated into the workflows, and it has human-in-the-loop capabilities so you can correct your AI when it gets stuff wrong. In 2024, we were an AI-powered automation product, positioning ourselves as the modern alternative to Zapier. We got to initial traction and then early product-market fit. But we realized that by positioning ourselves as an automation product, there were two major limitations. One, you limit the audience of people that think you’re the tool for them. We want to tackle the much bigger opportunity of helping every business get more work done with AI. And second, we didn’t want to be perceived as a duct tape product that only exists to temporarily glue two products together. We want to be a transformative tool. So the evolution we’re making now is transitioning from an AI automation platform for no-code workflow builders into an AI agent building platform for everyone.

    Nataraj: When I see a product similar to yours, the problem is we are using so many tools and so much data is spread across different things. How are you prioritizing which tools to bring into the platform?

    Jacob Bank: Right now we have about 120 native integrations. The way we think about it is that there are about 12 categories of tools that pretty much every business needs. Every business has an email client, a calendar client, a messaging tool, a CRM, an email marketing tool, an e-signature tool. There are these 12 to 15 categories that are quite ubiquitous. In each category, there are three to 20 players that have material market share. We’ve basically just tried to work our way down that list for our target audience, which skews towards small and medium-sized businesses. If you’re a regular SMB using modern tools, you’ll probably find everything you need with Relay. Zapier has 7,000 integrations; I don’t think you need 7,000. I think that’s a vanity metric. The number we need to get to is probably somewhere between 300 and 500 for the product to really feel complete. I believe integrations are skilled labor. I don’t think this is something you can just outsource. Building a really good Salesforce integration is really hard software engineering. Second, I believe agents will only be as useful as the robustness of their ability to interact with the tools you use. There are two big schools of thought: do everything in the browser or build on top of APIs. I think every serious player will need to do both, but if an API is available, that’s almost certainly a more efficient and robust way for the AI to interact with the product. We have focused entirely on robust API-based integrations.

    Nataraj: What has the traction been like? Give us a little bit of insight in terms of the scale of the company right now.

    Jacob Bank: We’re now at 440 paying customers. We have about 1,200 weekly active teams. That’s up from essentially zero when we launched at the very end of 2023. I’d call it early product-market fit. My personal definition of product-market fit for a product-led self-serve business is: could I go on vacation for a week and come back with more users, more customers, and more revenue? That is now true of our business. With 440 paying customers, there’s enough there to say that you’re not just a bespoke consulting shop for one or two companies.

    Nataraj: What are you doing to drive this adoption further? I think you’ve done very well in terms of product-led content growth, especially on LinkedIn.

    Jacob Bank: That’s super recent; we only figured that out in the past month. We’ve been building from the back of the funnel to the front of the funnel. Meaning we started with retention and depth of engagement, then moved to activation, and now have moved to working on top of funnel. In my first company, Timeful, we got 300,000 downloads the first weekend and retained none of them. I was scarred by that experience. So for this company, I would rather have 10 rock-solid, retained customers and then figure out how to bring more in. The strategy that makes sense for our kind of product has to be facilitated word of mouth, facilitated by content, community, and partnerships. I spend a lot of my time on content creation. One type is LinkedIn posts, which are teasers that illuminate a use case for an AI agent. I’ll post something like, ‘I just built a cool AI agent to synthesize insights from my customer calls.’ I’ll make a six-second GIF about it and pair that with long-form YouTube tutorials that show you how to actually build it. On LinkedIn, I now have 15,000 followers, and I’m getting about 150,000 impressions a month. Our YouTube channel will cross 10,000 views for the first time this month. It’s an order of magnitude fewer views, but super high intent. About 25% of our paying customers come from YouTube. Now that we have a robust community, many of them are writing LinkedIn posts or building templates, which helps solve the problem of people figuring out what to use a horizontal product for.

    Nataraj: How come there’s no LinkedIn integration when you post so much on LinkedIn?

    Jacob Bank: We’re actually in the review process from LinkedIn right now. We’re waiting for them to flip the bit to accept us, but it’s coming very soon.

    Nataraj: What integrations are coming in the next couple of months?

    Jacob Bank: We have a public roadmap. LinkedIn is at the top. WhatsApp is coming—that’s a really highly requested one. Xero, the accounting provider, is another. We have a few more social media integrations to build, like deepening our YouTube integration and building an Instagram integration. We need to deepen our integrations with website builders like WordPress, Squarespace, or Wix. We just have Webflow at the moment. The drumbeat of integrations will go on forever, but we really want to cluster around the use cases where we’re seeing the most traction: content creation and marketing, research use cases in sales, and general back-office operations.

    Nataraj: There’s a lot of overlap with Make.com and Zapier. Do you see them as competition, and how are you differentiating?

    Jacob Bank: When people are deciding between Relay and other products, they typically consider two categories. One is the traditional automation players: Zapier, Make.com, N8n. The other is the new AI agent builders: Lindy, Gumloop, Relevance. With respect to Zapier, our main differentiations are a way easier product experience for non-technical users, AI is integrated much more natively, and we have human-in-the-loop support. For the AI agent builders, they typically have good AI primitives because they’re AI-first, but they don’t typically have the depth and robustness of integrations or perfect usability. We all have our strengths and flaws, but we’re all kind of circling around the same opportunity.

    Nataraj: This is your second company, and you sold the first one to Google. What didn’t work in that company, and what are you trying to avoid doing in this company?

    Jacob Bank: Two big lessons from that company. The first is that we let ourselves be a little seduced by top-of-funnel numbers when we should have focused on having 10 super high-value retained users. The second was we just didn’t understand business. It was like, oh, we’ll just build a mobile app like Instagram and eventually get bought for a billion dollars or monetize it with ads. It turned out there was this other business model of subscription B2B SaaS, which totally existed in 2014, but it wasn’t in our DNA. So for this company, I wanted to make sure it provided rock-solid value, high engagement, and high retention to a small set of customers before we expanded. And second, that from the very beginning, the business model made sense.

    Nataraj: You are at the edge where you might be called automation, but if you push, you’ll be called agents. How do you think these will look in two years?

    Jacob Bank: I think there are three principles that are going to be really important in agent building. One, agents will need a robust and reliable mechanism to interact with all your tools, likely through APIs in the next two years. Two, agents will need to give you some sort of intermediate representation of what they plan to do before they do it and give you the ability to give feedback. And third, you need a great human-in-the-loop mechanism to correct things and help the agent learn. I think we will primarily use natural language to instruct an agent, then iterate on its plan, and then work with it to get the final output. This pre-compiled version of the flow chart is more understandable to users and will run more reliably and faster in practice.

    Nataraj: What’s next in terms of scaling? Are you planning to fundraise?

    Jacob Bank: We don’t feel any need to fundraise at the moment. We have plenty of runway, and our revenue is growing quite quickly. It looks like we’d be able to make it to profitability if we had to. That said, we will likely want to raise additional capital because it’s such a big opportunity. But my philosophy on company building has changed. It used to be you raise a round and triple the company size. For the kind of business we’re building—we have nine people right now—I can see us needing 12 or 15, maybe 20, but I don’t see a near-term future where we need 200. Modern company building is going to look very different.

    Nataraj: This was an amazing chat. Thanks for coming on the show and sharing all your insights.

    Jacob Bank: Thanks so much, it was a blast.

    This conversation with Jacob Bank highlights the incredible potential of AI agents to transform business operations. His journey with Relay provides a clear roadmap for building a modern, lean, and highly effective company in the age of AI, focusing on real customer value over vanity metrics.

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  • Building a Billion-Dollar Portfolio: A Conversation with David Blumberg

    With a career spanning over three decades, David Blumberg of Blumberg Capital is a veteran of the venture capital world. His journey began in the early days of tech, long before the dot-com bubble, shaping his perspective on what truly drives innovation and success. David was one of the first American VCs to recognize the potential of Israel’s tech ecosystem, contributing to its rise as a global ‘Startup Nation.’ In this conversation, David shares his wealth of experience, from his first investments at T. Rowe Price to founding his own firm. He delves into the key principles that have guided his investments through multiple economic cycles, the unchanging truths of human nature in a tech-driven world, and the importance of backing serial entrepreneurs. He also provides a look into his current investment thesis, focusing on data-intensive companies and the transformative power of AI.

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    Nataraj: How did you get into investing in early-stage tech companies? At what point did you decide that you should start investing in tech companies?

    David Blumberg: I’ll go all the way back to my high school days because I’m from that generation that came of age after the Watergate scandals of the 1970s. That was an era when a lot of people were depressed about the future of America, about the future of government, and about the ability to solve big problems. I was idealistic. I wanted to solve problems, so I thought I should go into government. I was lucky enough to go to Harvard College, where I started to study international relations in the government department and economics. I loved the courses and was soaking it up like a sponge. I worked in Washington for three summers and after those three summers, I realized that Washington was a place that causes a lot of the problems, it doesn’t solve them. They try, but they have this problem called unintended consequences, which often happens in a non-linear fashion, and a lot of their projections are made in linear models.

    At the same time, I had three big influences that moved me toward business. One, I was a middle-class kid, so I needed to work. I started a business at Harvard called Harvard Distribution Services. That company still is going today. It’s part of Harvard Student Agencies. I employed 100 kids doing distribution and courier service. It wasn’t a tech business by any means, but it was so much fun to serve customers, hire my friends, get paid for it, get feedback, and build new ideas for what we could offer them in the future.

    Then I had this negative experience in Washington where it was very sexy. I was close to power, at the foot of a senator learning about all these policies, but there was just this level of bureaucratic slowness and lethargy. Nobody cared that the taxpayer was always on the hook, and there was no accountability. I didn’t like that.

    Then there was the other interesting thing. I did a thesis on African-Israeli relations between 1973 and 1981. A relatively obscure topic. In 1973, there was an oil embargo after the Yom Kippur War. The Arab countries mostly forced the African countries to break diplomatic ties. But in those same years, trade went up 800% between those same countries that had just broken off diplomatic ties. I thought this was unusual. What I found out by doing a lot of research is that it was the business people, the military people, and the ministers and priests who would bring their flocks to the Holy Land that kept going despite the political rhetoric. They had real interests—economic, military, and religious—and those persevered over the political noise at the UN.

    Here’s my conclusion. I decided that I want to help impact the world while I’m alive. I’ve benefited from the history of all the progress of Western civilization, and I want to increase goodness for the world and help everybody thrive. My watchword is human flourishing. To me, the most high-impact way to achieve human flourishing is a combination of capitalism and science. The vehicles, the prophets that drive that forward are entrepreneurs. So I am all about entrepreneurs. I love entrepreneurs. I am an entrepreneur, but mainly I back them now as a venture capitalist. That’s my role in the world, and I feel blessed and grateful that I get to do this every day.

    Nataraj: When did you first start investing in a tech company, and if you can remember, what was the first tech company you invested in?

    David Blumberg: It was as a public investor. After Harvard, I went to T. Rowe Price, as you mentioned. At T. Rowe Price, I was on the technology team as an assistant securities analyst. My job there was to meet companies that were often about to go public, so they were private and about to do an IPO. I would form an opinion on their financial progress, their future, and their marketing relative to their peers. We would come up with a thesis about which of the IPOs in a new industry we would want to invest in. I started investing that way by making recommendations to the portfolio managers. One of the ones I remember investing in was a company called Scitex. You mentioned that I also invested in Israeli companies for a long time.

    That was interesting because T. Rowe Price had never invested in a public Israeli company at that point. Their theory at the time was, ‘Israel’s a very socialist country. It has a very high inflation rate, and there are these periodic wars and terrorism. It’s probably a dangerous place. We shouldn’t invest there.’ My counterargument was that’s already priced into the stocks. Their price-to-earnings ratio was lower than a comparable company in the US or London. They bought my argument, and we started to look at Israeli companies and start to buy them. Scitex was one of the first that helped get into the T. Rowe Price portfolio.

    Nataraj: So this is an Israeli company that was going public, or already public, and Israel was considered a socialist country at that point in time.

    David Blumberg: At the time in the 1970s and 80s, yes.

    Nataraj: I remember India was mostly considered socialist until 1990 when the economy opened up. That makes sense.

    David Blumberg: India and Israel share a lot in common. They both had the experience of British colonialism. The British did some good things, and some bad things. One of the bad things was that there was a very powerful group of economists from the London School of Economics that believed in import substitution as an economic model. Israel was told to do that, and India was told to do that. It was completely the wrong idea and really messed a lot of things up. For example, when I first went to Israel, they had a very strong tariff on personal computers. I said to some of the government folks, ‘If you’re trying to build a software industry, it doesn’t make sense to have high tariffs on the tools you need to write software.’

    Over a period of time, not because of me, they started to reduce tariffs and regularize taxation of venture capital funds. But in the early 80s, there really wasn’t any venture capital in Israel. There was onerous taxation and not the kind of stock option permissibilities that we take for granted in the US. Silicon Valley was novel. Some lawyers tell me that I was the first person that brought a standard Silicon Valley term sheet from Wilson Sonsini over to use on a deal in Israel in the early 80s.

    Nataraj: There’s this amazing book called Startup Nation about Israel. Silicon Valley is obviously the gold standard for tech innovation, and Israel probably comes second or third internationally.

    David Blumberg: Certainly in density per capita, it might even be higher in terms of entrepreneurs per capita. But Silicon Valley is the center, no doubt.

    Nataraj: There’s an interesting comparison of countries which got independence around the same time as Israel. For example, South Korea and Israel. But Israel was able to develop a tech sector that is as innovative as Silicon Valley. One of the projects that helped them was Yozma, where the government allocated funds and made it lucrative for venture funds to come into Israel. Were you exposed to or part of Yozma at that time?

    David Blumberg: Yes, I was very involved. I even helped contribute to some of their ideas, in a very small role. But most of the credit goes to other people. Here’s what I want to push back on: the notion that government leads on these things. I don’t really believe that. I was invited by TIE, The Indus Entrepreneurs, to come to India on a delegation in 1999 to talk to the leaders of India. We met with the finance minister, the military folks, all kinds of leaders of the economy. They said, ‘We want you to tell the story of Israel because Israel had the same British colonial history. They were also a people full of mathematicians and scientists like India, and yet both of those countries lagged until they had a takeoff.’

    These Indian folks said, ‘We were village boys in India. We came to a good university, then we went to America and became super successful entrepreneurs because of the American system of the government getting out of the way.’ Whereas in India, Israel, and most developing countries, there’s so much bureaucracy and red tape, which allows bureaucrats to get rich through corruption. It really impairs and depresses entrepreneurial energy. The most important thing for governments to do is just get out of the way and let the entrepreneurs do their thing. We have too much permitting, too much regulation, too much red tape. It’s very hard to do things now in the United States and in most Western democracies. We get sclerotic. What India needed to do was get out of the way of its own people. Israel had to do the same thing. Israel had, since 1948, the most advanced technological workforce in the world per capita, but they were not that successful in tech until the government got out of the way. They had economic reforms and allowed stock options and equity structures. I’ll remind you that in the late 80s, the Israeli economy crashed entirely. The banks failed, the government nationalized all the major banks. It was a complete disaster. It was only with the help of Chicago-style and MIT economists who basically said you have to allow the free market to work its magic. The same thing is what we told India in the 90s, and you’ve seen the power and growth that India has enjoyed too. It’s not that government leads so much as it just needs to get out of the way.

    Nataraj: I think I agree with you. The way I understood Yozma was they sort of aligned the incentives and got out of the way.

    David Blumberg: Let’s go specifically to Yozma. Most governments are driven by political goals. In Yozma, certain constituents wanted private sector institutional funding. That became the Yozma program. There was another fund to get the retail investor interested. Yozma did a program where if I raised a fund of $100 million, Yozma would put in another $100 million. At the end of the fund’s life, if the fund was a success, we, the investors, could buy out the government at cost—a great deal. The other program, which did not work very well, was an insurance policy attached to publicly traded venture capital funds. It did not work. Again, it’s government trying to be too smart and do too much. The main thing government had to do was get out of the way. I will applaud Yozma because they insisted on one good thing, which was cross-collaboration between experienced international venture capitalists from the US and Europe and Israeli local investors who were doing this for the first time. That was positive because there was a flow of information and a transfer of knowledge.

    Nataraj: Another interesting fact about the Israel ecosystem is Warren Buffett’s first investment outside the US was an Israeli company. Intel’s first office outside the US was in Israel.

    David Blumberg: Yes, Iscar.

    Nataraj: The founders they come up with are usually very exceptional and one of the highest quality of founders that I’ve ever seen in any other ecosystem.

    David Blumberg: That did not exist before. Israel did not have MBA programs or a culture of appreciating entrepreneurs. In the old days, under the socialist regimes, the smart kids went into the government or the military. Then a few people became successful entrepreneurs, and they became paragons and role models for the next generation. I will credit this: the Talpiot and the 8200 programs, these special units in the military that recruit the brightest people, give them great training, put them in a small group, give them a budget and a deadline, and say, ‘Here’s your project. You must design this new kind of technology.’ They’re bonded through fire. They put people together who know electronics, physics, radar, and tell them, ‘Build this, and your grandmother’s life depends on it.’ These people are forged together, tempered like fine steel. When they come out of the military, they have been bonded and tested. When you’re finding a co-founder, if you’ve been through that experience of the military together and you’ve had each other’s back, it’s a very powerful way of determining if this person is going to be a good co-founder.

    Nataraj: Before starting your own firm, you also worked at Claridge. Talk to me a little bit about that experience and how that shaped your investing later on.

    David Blumberg: I’m going to go backwards a little bit because my first mentor was Fred Adler. I met him when I was at T. Rowe Price, and he was the only big, successful American investor who was also willing to invest in Israel. I was interested in that combination. I want to give him great credit because although he was a very difficult man, he was brilliant and he exposed me to venture capital. Then I was fortunate to work with Alan Patricof, another great venture capitalist. And then I worked for Charles Bronfman at Claridge, which is the family office of the Bronfmans in Montreal. I was investing in the US, Canada, and Israel. Family offices have different criteria than a traditional venture capital fund. They had certain personal issues they wanted to steer clear from and other areas they wanted to emphasize. Their background was real estate, which was a little incompatible with my background in venture capital. I had to push and pull and try to explain why we should structure deals in a certain way. For example, they were used to structuring deals with debt. I pretty clearly explained that debt in a venture capital structure in the early stages is not really worth the paper it’s written on, and we need to be equity owners and get rewarded for that equity risk.

    Nataraj: So then you went on to start your own firm.

    David Blumberg: That’s right. The best deal I did at the Bronfmans, which I’m kind of proud of, was a little pharmaceutical company in Israel. I looked at it as an acquisition. The Bronfmans were not willing to do it on our own. So we bought a company called ABIC and back-to-back flipped it right away into Teva Pharmaceuticals in return for a large stake. Teva at the time was only worth about a billion dollars and later rose to between 40 and 60 billion. It was a rocket ship, selling to 50-plus countries. It’s now the largest generics manufacturer in the world. It was a real testament to that Israeli innovation mindset.

    Then, moving on to Blumberg Capital, I started that in the early 90s. At first, I didn’t have a fund, so our team was very small. We called it a virtual venture catalyst. We would work with investors, mostly family offices, to find deals for them. In compensation, we received a retainer, cash on the completion of a deal, and equity as a kicker. We had nine investments, and it was a 9x return on that portfolio. Four IPOs, four M&A exits, and one death. In 2001, Blumberg Capital raised its first venture capital fund. Since then, we’ve raised six funds and now have about 65 companies in the portfolio. Our offices are in Miami, New York, San Francisco, and Tel Aviv. We’re about 27 people on the team. We have two strategies: one is early stage, focusing on pre-seed, seed, and A rounds. Then we have a growth fund that starts late A, early B.

    Nataraj: When you started your first fund, to now, it’s more than 20 years. Valuations have changed, things have changed drastically. What didn’t change in this business?

    David Blumberg: What did not change? I love that question. I’ve got a great answer. Technology changes, human nature doesn’t. The lesson we learned from that is the context is constantly changing. Valuations are up and down. We know that there are cycles. Nothing lasts forever. The average length of duration on the Fortune 500 list used to be about a century; now I think it’s down to about 15 years. Most of the large companies of today didn’t exist 50 years ago. So the pace of change is accelerating. The lesson of life is keep running. The lesson of Silicon Valley is keep up with the change.

    Human nature is going to stay the same. There are jerks, and there are great people. There are incentives that motivate people and bureaucratic constraints that slow people down. My lesson from venture capital is it’s about the network. It’s about the people. If you treat people right, as you know from the karmic principle, it will generally come around to benefit you. If you screw people up, they’re going to remember. If they screw you up, hopefully, you will be smarter the next time and not want to work with them again. So I think that technology changes and you’ve got to keep up with it, but human nature is quite stable. We have been so blessed to work with serial entrepreneurs. We’ve backed them one time and they were successful, twice and they were successful, and sometimes we’re on our third round with these entrepreneurs.

    Nataraj: Who are some of those entrepreneurs that you repeatedly work with?

    David Blumberg: One fellow is Oren Netzer, the founder of DoubleVerify. We invested $8 million in the seed, A, and B rounds. Ultimately, we were able to take out $578 million in profits when the company went public. He’s started a new company called DataHeroes, and we’ve invested in that. Another example is a man named Dan Sanker. Dan has been the CEO of two of our companies. One, CaseStack, in the logistics area, was sold for $255 million. The acquirer did not want a small skunkworks Dan had set up, so I said to Dan, ‘Let’s just take it and build another company.’ We built another company, and seven years later we sold that company, SupplyPike, for another $216 million. Now Dan is going to do the next company with us, so that will be the third time. Another is Benny Nachman, the founder of Credorax, an Israeli/Maltese merchant acquiring bank. That company ultimately sold for $1.1 billion to Shift4. Now he’s started a new company called Jazzypay, which we’re also invested in. These ties that bind are absolutely wonderful because I know how he thinks, he knows how I think, and we trust each other. We’ve been through hell and back together.

    Nataraj: In pre-seed, there is no data. It’s all qualitative. Talk to me a little bit about your decision-making in pre-seed, especially for a new founder.

    David Blumberg: At the pre-seed stage, the premium is on the team. The team is much more important because they’re going to pivot no matter what they say. Something’s going to change. A successful investor once told me, ‘No good company pivots less than twice.’ I don’t know if that’s statistically true, but the point is very few people can really predict the future. It’s opaque, it’s unknowable, it’s probably non-linear. So you’ve got to be able to react quickly and effectively. A great team is more likely to do that than a not-so-great team. We look mostly for the teams. I also look for large market potential because it’s better to hit a big target. We also favor industries where there’s not a lot of competition. My friend Peter Thiel talks about this a lot, like little monopolies. Some of the best companies, like DoubleVerify and Nutanix, really didn’t have much competition at all when they started. Or what they were doing was very distinct. We could differentiate and say, ‘They do it this way, we do it differently, here are our advantages.’ So, team first, large market, and minimal competition are three of the key factors for us.

    Nataraj: I’ve come to think of two criteria in pre-seed. One is I want an absolutely insanely talented founder, and my definition is they must be writing code way better and faster than any senior team inside Microsoft or Facebook. Do you have your own definition of what talent is for you?

    David Blumberg: You remind me of my mother who used to say, ‘Before we had children, I had three theories about raising them. Then I had three children, and I no longer have any theories.’ My analogy would be Nutanix. We were the first investor. We made hundreds of millions of dollars on the exit. They came to us and described exactly what you said. Mohit Aron was one of the most technical of the three. He was considered one of the 50 best programmers in the world. He came from Google, he helped develop the Google File System. He and the other two founders said, ‘We’re going to do what Oracle does for storage. Everybody buys these old, big systems that are hardware and software. Instead, we’re going to emphasize the software and buy commodity hardware.’ We have this wonderful CIO Council. We took the Nutanix trio to them and said, ‘If they build this virtual storage idea, would anybody buy it?’ Three hands went up. Those became their initial customers. But the funny story is, you’re right, they were all really talented. Mohit was probably the most talented coder, but Dheeraj was an executive and Ajeet was the other fellow. They were all brilliant. Each of them started unicorn companies. Ajeet started ThoughtSpot, and Mohit started Cohesity. So they split up, but they were each successful in their own domain. So I think quality is recognizable. You tend to want it to be coding quality, but there are other qualities. I heard somebody recently say that every CEO needs to be the best salesperson for their company. I think that’s true. They may not be the best coder, but often the lead in the company is going to be the more business-oriented person.

    Nataraj: You talked about the CIO council you have. Talk to me about that council and how it’s helping you pick winners and losers.

    David Blumberg: Our innovation council consists of chief information officers, chief security officers, and chief technology officers. We get them together about four times a year. They really enjoy conversations among themselves on a topic of mutual interest, like AI in production applications given privacy constraints. We’ll have them talk about that topic, and then we present a couple of our companies, either before or just after we’ve invested, and we get feedback for the entrepreneurs from this council about how well the messaging is coming through, product-market fit, pricing, and the go-to-market plan. A lot of feedback comes, and often what comes next are design partners. It really helps because there’s credibility that we’ve built up over decades of bringing them companies like Nutanix, DoubleVerify, and Braze. When these CIOs see something from us, they know that we’ve vetted thousands of companies down to a few that we invest in every year.

    Nataraj: I always like to ask investors where they’re investing their own personal capital. Can you talk a little bit about your own strategy?

    David Blumberg: Sure. First of all, I’ve been very fortunate to become wealthy through the venture capital business. We’ve had a lot of successes, and the carried interest really rebounds to the benefit of the investor founders. A lot of that capital comes in the form of stock in public companies. I’ve often held those stocks. Sometimes I do what’s called an exchange fund, where I’ll take a chunk of a concentrated stock and trade it over a period of eight years tax-free into the S&P 500. So I diversify without any transaction costs.

    I’ve also personally invested in real estate and particularly one non-obvious area. I really enjoy investing, and I’ve made a lot of money in oil and gas and fossil fuels. That’s very uncool, but I am what’s called an energy humanitarian. It’s fine for wealthy people to feel good about themselves by thinking about green energy, but you come from India, so you understand there are hundreds of millions of people that have zero electricity. There are 700 million people on earth with zero electricity today. Four billion people have less than four hours a day of access to electricity. The world needs a lot more power. The only possible way we can get the poorest people on earth to have enough energy is if we utilize more of the God-given resources of natural gas and coal. I’m all in favor of innovation—solar, wind, nuclear, hydro—where applicable. But the vast bulk, 80-plus percent of the world’s energy, is still coming from fossil fuels. So while everybody’s voting against it, I vote for it, and I make lots of money because when people are voting with their emotions instead of the data, they lose and I win.

    Nataraj: Who are the investors you admire the most and like to learn from?

    David Blumberg: Peter Thiel is a friend, and I admire him greatly for his intellect, his ambition, and his rule-breaking mindset. Joe Lonsdale is in a similar vein, and we’ve invested a lot together. I also think that Marc Andreessen and Ben Horowitz are amazing; they’ve built an incredible franchise relatively quickly. Of course, the classics, the people at Sequoia like Moritz and Leone, are tremendous. And I’m old enough to have worked with some of the great guys from the old generation. Venture capital has changed. When I was starting out, it was very much a hardware business, centered around semiconductors and test equipment. That’s why we call it Silicon Valley. Today, obviously, it’s coders that are at the top of the rank. Now we’re automating the information world, the world of knowledge workers, the world of data. That’s why we at Blumberg Capital look for data-intensive companies that can sell into one vertical or more, using intelligent algorithms to shape, refine, distill, and interpret that data. Every industry on earth can become more productive. My way of describing venture capital is we are the outsourced R&D function for large corporations.

    Nataraj: What are you consuming right now—podcasts, books—that is influencing your thinking?

    David Blumberg: This always shocks people. I’m a huge reader of the Bible. I think that the Bible is the greatest guide to human nature, to wisdom, and to what really matters in life. I have a specific version I like by Dennis Prager called ‘The Rational Bible.’ It doesn’t require suspension of belief or disbelief in science; it’s totally copacetic with science. But it teaches you why and should, rather than just what and how.

    In other domains, I love listening to economics podcasts and edgy technology discussions about what’s going to be next in four, five, or 10 years. Also on demographics and regulatory changes. I like to read the editorial page of the Wall Street Journal. A politician who doesn’t understand economics is not going to be helpful, and an economist who doesn’t understand politics is not going to be successful. One needs to know both. I would say the most important thing is continuous learning. I’m told that an engineer today is outdated in seven years after they graduate from college because things are changing so fast. So nobody’s a genius constantly. You need to continue learning, and the best way is learning from other people.

    Nataraj: Who are your mentors who helped you in your career?

    David Blumberg: Fred Adler was one of my great mentors. A lady named Abby Joseph Cohen hired me at T. Rowe Price; she went on to become the ‘Queen of Wall Street’ at Goldman Sachs. Alan Patricof has always been a gentleman. Charles Bronfman is a prince of a human being, a great philanthropist. And the people I learned most from are the entrepreneurs we’ve worked with because they’re always confronting really difficult challenges. I love watching the way their minds think about how to overcome a challenge. That’s the beauty of being an entrepreneur and the privilege of being a venture capitalist.

    Nataraj: One last question, what do you know about investing now that you wished you knew when starting your first fund?

    David Blumberg: This is very easy. The most important thing for young people is to always get your contracts pinned down. Make sure you have a contract and it’s clear, especially if you’re doing consulting. Make sure that everything is written down and bound into a contract because after one starts a project, people’s memories change, incentives start to diverge, and you can get into a big fight. The most important thing is to get everything squared away up front. You can always adjust it later, but if you don’t get it signed, you’re at grave risk of losing what you’ve worked so hard for.

    David Blumberg’s insights offer a timeless perspective on venture capital, emphasizing that while technology constantly evolves, the fundamentals of backing great people and solving real problems remain the same. His story is a masterclass in long-term vision, resilience, and the power of building lasting relationships.

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  • DocuSign Founder Court Lorenzini on Building a $16B Company

    In this episode, we sit down with Court Lorenzini, the visionary co-founder behind the $16 billion e-signature giant, DocuSign. Lorenzini takes us back to the early days, revealing that the path to success was a ‘slow grind’ rather than an overnight explosion. He shares the fascinating inside story of how a presentation at Microsoft’s executive briefing center led to landing them as a pivotal first customer, providing the seal of approval that catalyzed their growth. The conversation also explores the strategic partnership with the National Association of Realtors, which embedded DocuSign into the daily workflow of millions. Beyond DocuSign, Lorenzini opens up about his subsequent entrepreneurial journey, including a spectacular failure and the invaluable lessons learned. He now channels this wealth of experience into his latest venture, Founder Nexus, a community designed to help fellow founders navigate the treacherous startup landscape and increase their odds of success.

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    Nataraj: You’ve started several companies; I’ve lost count on your LinkedIn profile. Everyone knows DocuSign, which has a market cap of $16 billion today, but you’ve founded a couple of companies before and some after. Could you share a bit about your career up to now?

    Court Lorenzini: Certainly. I started my career as an engineer. My undergraduate degree was in engineering, and I did three postgraduate master’s programs in different forms of engineering. But I always knew I wanted to be an entrepreneur, so for me, that was just a pathway to getting to where I am now. Early in my career, I worked for a semiconductor equipment company, ran a division for them in Europe, and then went to work for Cisco in the early days when it was on a rocket ship. During the years when Cisco was considered the fastest growing company ever, it was a fantastic place to learn leadership.

    Nataraj: I’ve had several guests who were at Cisco during that rocket ship phase. It fostered a lot of successful people.

    Court Lorenzini: It was a great place to learn. I moved to the Northwest in 1996 and started my first company at the dawn of the internet era, before e-commerce. I built one of the very first e-commerce engines and ended up selling that company. I tried my hand as a venture capitalist for a bit but realized I enjoyed building companies more than investing in them at that time. DocuSign was my second company, which I co-founded with a friend who had worked for me in my first company. I ran that as the founding CEO until 2008 and then left because my passion is the first phase of a company. I love what I call the ‘napkin to product-market fit’ phase, where every decision is life or death. That’s my favorite part of growing a business. In my career, I’ve structured it so that by the time I get to about year five and there’s a product-market fit signal, I tactically exit and go start another one from scratch.

    Nataraj: When you were starting DocuSign, what was the original thought? Did it evolve?

    Court Lorenzini: My co-founder, Tom Gonser, had the idea. He came to me after leaving my first company. His own company was in the process of selling assets from a prior venture it had acquired called DocuTouch. He called me and said we should build a company around the IP his company was trying to get rid of. In that IP package were two things of value: the trademarked name DocuSign and an issued patent for signing documents via the internet. I thought that was interesting. We extracted that, bought the IP from his company, and that’s the basis around which we founded DocuSign. He left his company, and we built it together. It was amazing.

    Nataraj: Was it obvious from day one that this was going to be big, or was it a slow grind to product-market fit?

    Court Lorenzini: It was a really slow grind. I remember telling the very first venture investor that it was going to be a winner-take-most proposition. They kind of scratched their head, and I said that someday, one market leader would have about 70% of the worldwide market share. There would probably be a second player with about 20% and a bunch of copycats in the last 10%. If you roll the camera forward to today, DocuSign owns about 76% of the worldwide market, Adobe has about 12%, and everybody else is in that last 10-12%. It came true exactly as I predicted over 20 years ago. It was not obvious; it was a grind. It took a lot of creativity to figure out how to get product-market fit, and it took years. We founded it in ’03 and didn’t go public until 2018, so it was 15 years to a public offering.

    Nataraj: Who were the first or most impactful customers?

    Court Lorenzini: The most impactful relationships were the ones that took it from ‘kind of cool’ to ‘going to be amazing.’ The first one was Microsoft. This was an interesting story. We were a very early adopter of .NET technology. It turned out that at Microsoft’s executive briefing center, the .NET team was presenting to executives. Without telling us, they used DocuSign as an example of a company using .NET in a cutting-edge, valuable way. In the audience was the chief legal counsel for Microsoft. From that meeting, I got an inbound phone call from him saying, ‘I was just at the EBC. I heard this thing is really cool. We should be using that.’ That’s how we landed Microsoft. It wasn’t me calling them; it was them calling me. Because it came from the legal team, it was blessed inside the organization from day one. At that moment, Microsoft was the biggest company in the world, so that helped a lot of other companies get comfortable. It was the seal of approval I needed. The next one by far was the National Association of Realtors (NAR). The NAR had software used by three million realtors nationwide to create home purchase and sale agreements. They liked what we had and agreed to embed our signing tool inside their software as a white-label deal. This meant every realtor in the country immediately had an opportunity to send documents to home buyers via DocuSign. That was a huge deal because it gave us volume and exposure to an incredible group of end-users who had day jobs where signing things electronically would be fascinating. We got a tremendous amount of lift from that deal.

    Nataraj: It seems like a sign you’re solving a real problem when customers come to you inbound. You predicted one player would dominate 70% of the market. It’s a seemingly simple software, so why does DocuSign still hold that position against competitors in the broader document management space like Adobe, Google Docs, and Box?

    Court Lorenzini: There are two core reasons. First, humans prefer consistency. If we were constantly forced to use a whole array of different signing methods, it would get confusing, and it would be hard to find your stored documents. Human characteristics were going to drive standardization on one player. It’s also a trust factor. The other main reason it remains dominant is that early on, we recognized that a key element to resolve wasn’t the signature itself but the flow of data between the universe of document creation tools upstream and the universe of document execution tools downstream. Upstream, you have Word, Adobe Acrobat, and special-purpose platforms creating documents with relevant data. Downstream, you have big software companies like Dynamics, SAP, and Salesforce that need that same data to produce, ship, support, and bill for a product. We invested very early in a set of robust APIs that could take data from upstream systems and seamlessly move it to any downstream system. We built years of expertise in data translation via APIs, creating a large constellation of tools that really cannot be replaced by a third party. Most enterprises won’t take the risk of replacing us because a competitor would have to have all the same tools working perfectly on day one. That moat has been a huge differentiated advantage for us.

    Nataraj: When you left DocuSign, did you sell your equity or keep it?

    Court Lorenzini: I kept it all and moved on to start several more companies. By the time the company went public years later, I still had all my equity.

    Nataraj: I spoke with Martin from Insights VC, an early investor in DocuSign, who said he never sold his shares and mentioned a ridiculous multiple. What did your multiple look like?

    Court Lorenzini: The shares were founder shares, so they were basically fractions of a penny, and they got to over $300 a share. It was a very healthy return, let’s just say.

    Nataraj: After five years, DocuSign was successful, yet you went on to found other companies. Are you an ambitious person?

    Court Lorenzini: I think people would describe me that way. I’m certainly an optimist, and I love the thrill of getting something off the ground. When you’re successful and you do it repeatedly, it means you’re in it because you love the game.

    Nataraj: What was your career like after DocuSign?

    Court Lorenzini: The third one was a renewable energy company. I was trying a business model that didn’t require much venture capital, just a few hundred thousand dollars in angel money. It was intended to be a cash flow business, which it turned out to be, returning cash to my investors. I wouldn’t say it was a giant hit, but it returned capital. Then I started my fourth company, a consumer data acquisition company called Metabright. That one was my most spectacular failure. It was a rocket ship with 50% month-over-month growth on a multi-million dollar run rate. Between that and absolute catastrophic failure took less than three months.

    Nataraj: Wow, why did it fail so drastically?

    Court Lorenzini: The technology we were building was data extraction from checkout register receipts. We built an OCR-based system that could read and translate that cryptic writing into real product data. We were licensing it to other application providers. Our biggest customer was delivering 90% of our revenue and growing like gangbusters. One day, the founder of their company was at an event and sat next to a young man who had just finished his master’s program in Croatia. He and his buddies had written a program to read receipts using a cell phone and was willing to give his code to my customer for free. Within weeks, my customer tested it and called me up to say, ‘You’re out. He’s in. Bye.’ When your 90% revenue customer walks away with no warning, you don’t survive that. I went to Croatia to try and buy the technology, but couldn’t get a deal done. I called my investors and employees and said we had to shut it down. It was very gut-wrenching.

    Nataraj: How do you evaluate opportunities now and decide if they’re worth your time?

    Court Lorenzini: I have a methodology I promote to early-stage founders. First, validate your product by testing if someone will pay for it before you even build a prototype. Get them to put down a down payment or something to test the concept. Second, and this is the one most people miss, actively try to kill it. I go back and find founders of companies that preceded me in the same solution space. I ask them what happened to their company and why it failed. Through that exchange, I learn all the fatal, foundational flaws I need to be aware of. It’s an incredibly eye-opening process. If you can diligently uncover and resolve all those fatal flaws with your approach, you’re probably on the right path. I tend to be pretty rigorous about both of those things before I jump into something new.

    Nataraj: Let’s talk about Founder Nexus. You’re not raising outside money for this. What is it, and why are you doing it?

    Court Lorenzini: Founder Nexus is my thank you note to the venture capital industry. I’m not trying to get myself or anyone else rich, but I’m using it as a vehicle to help founders on what is an otherwise difficult, lonely journey that’s statistically destined to fail. The odds of failure for a venture-scale founder are over 90%. I see these founders as a valuable global resource that isn’t being optimized. So I’ve set out to figure out how to raise the odds of success for them. Founder Nexus is a way for founders with experience to get together regularly and be motivated to help each other by sharing experiences, not advice. I gather these venture-scale founders, put them in subgroups, and create opportunities for them to actively share their experiences to level up their game. Success in building a venture is a series of variables multiplied together. If a single variable is zero, the whole equation fails. If you can get every decision to be made at 50% or above its potential value just by gathering information, that will inevitably raise the odds of success for all participants.

    Nataraj: Community is all about curation. How do you ensure the right people are in the room?

    Court Lorenzini: Curation is key. I filter out anyone who has never built a company before. They have to be well on their way, having already raised their first venture round or outside capital. I’m looking for valuable lived experiences. I also filter out investors, advisors, and service providers. This way, everyone knows the room is pure; everyone is another venture-scale founder who’s been there and done that. This creates an immediate sense of trust and vulnerability. We also build forums, but unlike others where you extract all the business wisdom in 18-24 months, our forums only last for 40 minutes each. Then, software reassigns everyone to new groups with new topics. You get three of these per event, so you hear from 12 to 20 new voices of lived experience each time. You’re also grossly expanding your network of highly qualified people for recruiting co-founders or C-suite talent.

    Nataraj: How’s the traction? Is it limited to Seattle?

    Court Lorenzini: We’ve held three events and have about 150 people signed up. We just opened it up to full membership. Our next event will be our first simulcast, with both a live and online component to allow non-Seattle participants. My long-term objective is to have chapters all over the world, stitched together so founders in one community can help founders in another. This way, venture-backed companies can live and excel anywhere.

    Nataraj: You’re an LP in a lot of funds. How do you decide which ones to invest in?

    Court Lorenzini: I’m very active in the Seattle ecosystem to give back to the community that helped me, but I’m not restricted to it. My wife and I have probably invested in almost 20 venture funds around the world. It’s always hard to decide who will be a good picker. I tend to like very early-stage funds; that’s where my passion is. Sometimes it’s a gut feeling, or seeing if a fund’s thesis gives them a leg up. A number of funds we’ve invested in are run by non-traditional VCs, like women or people of color in different regions. We think those investors know their market better and will probably get outsized returns.

    Nataraj: Has any area surprised you in terms of performance?

    Court Lorenzini: Geographically, no. But I will tell you that several of the women-run funds are grossly outperforming their peers. Female VCs are historically few and far between, but the ones we’ve invested in are dramatically outperforming the rest of the crew. It’s amazing.

    Nataraj: What’s your view on the current valuation landscape, especially with the AI craze?

    Court Lorenzini: I invest in early-stage funds, so by definition, these are not high-valuation entry points. If they’re betting on AI, they’re not writing big checks at high valuations; they’re coming in at the concept stage with bigger upside potential. My investing strategy is like a dumbbell. I have a ton of diversified dollars in the low end, and a few very concentrated private equity positions on the high end, right on the cusp of pre-IPO.

    Nataraj: Why did you pursue three master’s degrees?

    Court Lorenzini: Each of those master’s was opening a door to a new opportunity. I was working for a semiconductor equipment company that had a program to pay for advanced education. For me, each master’s program was a way to get a new promotion. I got three very significant promotions in a short time. Within three years of my undergraduate degree, I was going to Europe to start a new venture for that company. There’s no way I would have gotten that opportunity at 25 if I hadn’t done all that work. I did computer science at Berkeley, manufacturing systems engineering at Stanford, and optical engineering at the University of Wisconsin-Madison. Each one was a gateway to a new career step.

    Nataraj: What are you consuming right now that’s influencing your thinking?

    Court Lorenzini: I love to read. I recently consumed ‘The Three-Body Problem’ series, which was mind-opening. Also, ‘The Fourth Turning Is Here,’ which contextualizes where we are in history. I’m really fond of a book by John Levy called ‘You’re Invited,’ which was helpful for Founder Nexus. And another called ‘The Power of Pull.’ On a podcast basis, I’m a huge fan of Acquired and ACQ2.

    Nataraj: Who are the mentors that helped in your career?

    Court Lorenzini: Shout out to my dad first and foremost. My father was one of the eight people that founded Silicon Valley; he invented the process for growing silicon commercially and was on the team that discovered solar power. He started seminal companies. Also, the founder of KLA, Ken Levy; the original CEO of Cisco, John Morgridge; and his successor, John Chambers. They were huge influences.

    Nataraj: What do you know now about being a founder that you wish you knew when you were starting out?

    Court Lorenzini: I wish I had sought more experiential advice. I got a lot of guidance from people who gave me advice but not experience, and that usually set me in the wrong direction. When I talked to people who had lived the experience I was struggling with, I got better counsel. I also had to learn how to delegate effectively and, crucially, how to follow up to ensure things got done. And finally, learning how to proactively hold people accountable as a leader took a while to understand.

    Court Lorenzini’s journey offers a masterclass in resilience, strategic thinking, and the importance of community. His experiences, from the heights of DocuSign’s success to the lessons of failure, provide invaluable wisdom for any entrepreneur.

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  • Silicon Valley Secrets: 3x Exit Founder Ameesh Divatia on Data Security

    With three successful exits and a career spanning the core of Silicon Valley’s technological evolution, Ameesh Divatia offers a rare and valuable perspective on building transformative companies. From his early days in networking silicon and navigating the dot-com boom at Cisco to founding Baffle, a pioneering data protection company, Ameesh has consistently focused on creating new market categories. In this conversation, he shares the critical lessons learned from his entrepreneurial journey, including the importance of a customer-centric view, building strategic relationships with potential acquirers, and adapting to industry-wide shifts. Ameesh provides deep insights into the evolving landscape of data security, the challenges and opportunities presented by GenAI, and the timeless principles of finding the right idea and the right team to bring it to life. This discussion is a masterclass for any founder or tech leader looking to understand the mechanics of long-term success in a fast-changing world.

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    Nataraj: We like to feature founders solving interesting problems, and you’re tackling data protection. Before getting into what Baffle does, can you give a little introduction to yourself and your journey so far?

    Ameesh Divatia: Absolutely. I have a traditional engineering background. I grew up in India, got my bachelor’s degree there, and came here for graduate school. After grad school, I got into the computer networking industry, which was a very hot space at the time. I was fascinated with how computers could be connected and evolve into a larger IT paradigm. My first job was as an application engineer supporting networking silicon, but I quickly moved into an architectural role because I was always interested in the big picture and understanding how the customer was using the product. That has stayed with me forever. I moved into a system architect role and eventually went to work for 3Com, one of the big three along with Cisco. After about three years there, I decided I wanted to do something on my own. I quit my job, came up with an interesting angle on using data networking concepts for optical networking, and that was my first startup in the late 90s. My second startup was in storage networking, the third was a turnaround in silicon photonics, and now Baffle is in data protection. My journey has taken me through very different spaces because I like to learn new things and go after complex technical challenges. I’ve also been extraordinarily lucky; all three of my previous startups were acquired. In every case, we built a completely new market for the acquirer or the space in general.

    Nataraj: Looking at your career, you were at Cisco during one of its most interesting times, the dot-com bubble. At one point, wasn’t Cisco the highest-valued company?

    Ameesh Divatia: It absolutely was. It was sort of like the NVIDIA of the dot-com bubble. This whole NVIDIA story is something we have lived through. I don’t want to say it doesn’t end well, but it doesn’t stay like this forever. But it was euphoria. You would get into the office and see the stock up six bucks, and we literally thought we could take over the world. We were newly acquired into Cisco, and two things about Cisco were amazing. First, they always reinvented themselves. John Chambers had an edict that companies have to reinvent themselves every four years. We were acquired and built a completely new business on the optical networking side. Second, when you get acquired at Cisco, you are treated very well. I remember we had a record of 33 EBCs in a quarter. It was insane; every day, the who’s who of the networking and telecom world—AT&T, Verizon, Deutsche Telekom, France Telecom—would be there, and we would be presenting to them. It was a magical time.

    Nataraj: Any advice for whoever is inside NVIDIA that you did or didn’t do when you were at Cisco?

    Ameesh Divatia: Be humble, that’s it. NVIDIA is a different story; it’s an overnight success that took 30 years. They completely deserve what they have, but it will be disrupted. Every company has to fight to be the incumbent and drive the industry. Some are more successful than others, but nothing lasts forever.

    Nataraj: Your company before Baffle was also acquired by Cisco.

    Ameesh Divatia: That’s right. One thing I’ve done a lot is get involved with prospective acquirers very early. I always tell entrepreneurs not to rely on someone else to find you the exit. You have to build relationships over time. You have to be open about sharing your value proposition, but not your crown jewels. With Lightwire, it was a very capital-intensive project in silicon photonics. You need a big brother. We went out and shortlisted companies, saying, “Look, we have this amazing technology, but we need somebody to productize it.” We got a few interested, and eventually, Cisco not only got interested but invested $20 million in a $40 million round and started working with us. They needed to pack a terabit of throughput in a router blade, which wasn’t possible with existing technologies. They gave us a spec, and our team did it in less than two years. At that point, Cisco couldn’t let that technology be out there because it was critical for their success, so they decided to buy it. It was the first time they had ever bought a component company.

    Nataraj: Is this technology actively used today?

    Ameesh Divatia: Absolutely, it’s a billion-dollar business line right now for just this product, and they’ve expanded beyond that.

    Nataraj: And you served as a partner at an investment fund, Carta. What was that experience like?

    Ameesh Divatia: After that exit, I was done with operating roles and wanted a break. I thought I could take my expertise to help others at a very early stage. My CFO, one of my mentors, and I started Carta as a seed-stage fund to invest in companies. We invested in eight different companies, and six of them have been acquired by now. It was an interesting experience to be on the other side, but I quickly got bored. It’s not like running the place; you’re watching the entrepreneur run it. Then a great idea came along, which is how Baffle really started, and I jumped back in.

    Nataraj: You mentioned you’ve always created new categories. How was Baffle a new category at that point?

    Ameesh Divatia: We had the vision to create a new category. If you look at security, it started with protecting the pipe—the network—which led to the device wave with firewalls. Today, we are in the identity boom because we don’t own the infrastructure anymore; the data center is in the cloud. We think this is setting it up nicely for the next big thing, which is actually protecting the data itself. Identity can only go so far. If you protect the data at the record level with encryption, there’s no way to look at the data unless you have access to the keys. You’re making the hacker’s job much harder. Security has always been a race. We feel data is the next big frontier. If you protect data at the record level, you don’t care if a hack happens, because whatever is stolen is ciphertext. That’s the category we are creating: data-centric protection. The industry is starting to gravitate towards that, especially with the GenAI explosion, because you have to share your data to get good outcomes. The fundamental problem we solve is that once data moves to the cloud, you don’t want the cloud vendor to see it.

    Nataraj: At what abstraction level does Baffle come into the picture, and who’s your typical customer?

    Ameesh Divatia: We operate at the application tier. It’s a pure application layer solution with no dependence on any processor, operating system, or programming language. We intercept the packet that goes between the application and the database as a network-level proxy. A typical customer is the one responsible for infrastructure in the cloud. But it starts with compliance regulations. We started in 2015, and GDPR came into effect in 2018. Security sets the rules. Data analysts or prompt engineers want to move data to the cloud, but security says no unless it’s compliant. That’s when the infrastructure provider, responsible for the database, has to adopt Baffle.

    Nataraj: There’s criticism that regulations like GDPR benefit big companies and make it harder for startups. What are your thoughts?

    Ameesh Divatia: If you ask me, regulation is not going far enough. If regulation was great and everyone was compliant, we wouldn’t have hacks. But regulation should be easy to adopt. With data-centric protection, you’re taking a proactive measure to protect your data and ensure your customers’ data won’t be stolen. That enhances your reputation and builds trust. I don’t think it’s worth fighting regulation; it’s important to embrace it. GDPR has now been taken to a new level with things like CCPA and CPRA, so it’s proliferating.

    Nataraj: When GDPR first came out, did things improve, and did the tooling evolve so a small company could also comply?

    Ameesh Divatia: Absolutely. One of the big things about GDPR is the right to be forgotten and the bring-your-own-key model. That’s something we have enabled for any SaaS vendor. It used to be very complicated; you had to buy an HSM, know crypto, encrypt your data, and manage keys. We’ve completely abstracted that away from the developer. You just tell us who the tenant is, associate a key with them, and our tool handles the rest. If a tenant wants to trash their data, they just take the key away, and the data becomes invisible.

    Nataraj: Talk to me about your initial go-to-market strategy. How did you pitch your early customers?

    Ameesh Divatia: An entrepreneurial suggestion is you don’t want a channel on day one. You want to go direct to know what the end customer is doing. The key is to find an early adopter with a pain point that only you can solve. We found a gap in the industry with Postgres databases, which are fast-growing but have no native encryption capabilities. Our first customer tried a DIY strategy and failed miserably. They found us. Digital marketing, SEO, and SEM are absolutely critical for any business these days. People don’t like to be cold-called; when they need something, they search. You have to advertise and write lots of content. We started with a direct strategy, and to scale, we’ve gravitated towards using the cloud vendors themselves as our channel. It’s counterintuitive, but they have a shared responsibility model. We help them implement it, allowing their customers to take control of their data. This helps the cloud vendor migrate more customers and make 100x what they would pay for us.

    Nataraj: Security is a cat-and-mouse game. What are the current trends in the security industry?

    Ameesh Divatia: The most important trend is the evolution away from just monitoring. Things like SIM logs are being reimagined with GenAI for automated monitoring and alerting. But monitoring is great for identifying problems; what about remediation? Discovery is a big space, but just classifying data doesn’t make the problem go away. Remediation is the big trend. How do you remediate data so it becomes invisible? Encryption, masking, tokenization are techniques that can be used. We allow field-based control to transform data so it’s safe in environments you don’t control.

    Nataraj: You brought up GenAI. How are you thinking about it as an entrepreneur who has seen multiple technology cycles?

    Ameesh Divatia: This is going to be a multi-year cycle and a massive productivity improvement. We’re seeing it in multiple places. Our engineers use co-pilots all the time, which helps remediate things like CVEs. We use it in our customer success environments as well. A new engineer can troubleshoot a problem without needing to know who the actual customer is. We tokenize the customer name, put the data in a repository, and run GenAI models on it. From a product perspective, it will completely transform data discovery, which has never been a fully solved problem. We expect to integrate it across all our functions—sales, marketing, product blogs, all of it.

    Nataraj: If you were starting a new company right now, where would you look for opportunities?

    Ameesh Divatia: I have lots of ideas, but implementation and commercial fit are key. I strongly feel we are in a phase where ease of use and adoption are critical. One of the biggest problems with GenAI is that it lies with authority. Figuring out ways to detect that is a massive opportunity. In general, anything in the data realm—getting the right dataset into the hands of the right people—is always going to be a lucrative area.

    Nataraj: Are your customers doing data deals with other companies to build GenAI solutions?

    Ameesh Divatia: Yes. Data sharing was always selective, but GenAI is changing that. You have to share your data, but it’s hard to do without compromising customer trust. That’s where data-centric security and privacy-enhancing computation will be critical. There’s still a tremendous problem in making it easy to use, and I see a lot of innovation coming where you can share data securely.

    Nataraj: This is your fourth company. Do you have a checklist or mental model you follow when evaluating a new idea?

    Ameesh Divatia: I wish. All four happened for very different reasons. The most important thing is you have to get excited about an idea. Second, and sometimes more important, is finding the right team to work with. It’s like a movie: you need the right plot and the right team of actors. You want people who are subject matter experts in their areas. After that, there’s a whole slew of commercial things: find the right market and make sure it’s a critical solution, not just a nice-to-have. But those first two are the most important to start.

    Nataraj: What do you consume for information? Any books or podcasts?

    Ameesh Divatia: LinkedIn is a big source of my information. I also like reading business books, though I often get the gist through something like Blinkist. I like to read about entrepreneurs and innovators, so I’m a big fan of Walter Isaacson. He writes really well when it comes to capturing a person’s history.

    Nataraj: Who are the entrepreneurs you most admire?

    Ameesh Divatia: I’ll start with the founding fathers of this country. I think they were the ultimate entrepreneurs. They completely wrote the model from scratch, which gives me the most confidence in America’s future. Nearer term, of course, Steve Jobs was an amazing entrepreneur, as is Elon Musk.

    Nataraj: Who are your mentors?

    Ameesh Divatia: I’ve had a lot of them. It starts with my family—a supportive spouse who gives the right feedback. My father was a big influence. And I’ve had many other mentors in Silicon Valley who helped me along the way and continue to help me today.

    Nataraj: What do you know about being a founder now that you wish you knew when you were starting your first company?

    Ameesh Divatia: This is a tough one. As an engineer-founder, you tend to fall back on the idea that the technology will sell itself. That is seldom the case. You have to constantly adapt the story based on what the customer perceives. The technology is a cornerstone, but you have to constantly make sure the commercial value is there. If I knew that, I would have looked at the business side of it way earlier in a lot of cases.

    Nataraj: Ameesh, thanks for coming on the show. This has been a very fun and insightful conversation.

    Ameesh Divatia’s journey offers a masterclass in navigating Silicon Valley’s dynamic landscape. His insights on creating new markets, adapting to technological shifts like GenAI, and the foundational importance of data-centric security provide a valuable roadmap for entrepreneurs and innovators.

    → If you enjoyed this conversation with Ameesh Divatia, listen to the full episode here on Spotify or Apple.

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  • Prakash Chandran on Building Xano, a Scalable No-Code Backend

    In the evolving landscape of software development, the demand for powerful, scalable applications often outpaces the supply of engineers. This gap has fueled the rise of no-code and low-code platforms, but many come with limitations in scalability and security. Enter Xano, a platform dedicated to providing a robust, enterprise-grade no-code backend. We sat down with Prakash Chandran, co-founder of Xano, to explore his journey from leading design at Google to tackling one of the biggest challenges in modern development. Prakash shares how his experiences, including a self-described “failed startup,” shaped his vision for Xano. He discusses the platform’s unique approach of focusing solely on the backend, empowering citizen developers to build complex, scalable applications without writing a single line of code, and moving beyond the prototyping phase to full-scale production. This conversation offers deep insights into the future of software creation and the power of abstracting complexity.

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    Nataraj: On the Startup Project, I like to feature interesting products solving interesting problems. As I explored Xano, I found it’s at the intersection of a couple of very interesting trends in how we develop and scale applications. I thought it would be useful for our audience to discuss what you’re building at Xano. Before we get into that, can you give a little introduction about yourself and your career before starting Xano?

    Prakash Chandran: Absolutely. After I graduated from Cal Poly Pomona, I joined a small startup called Picasa. Google ended up buying Picasa, and it became Google Photos. My coworkers called me very lucky because I had no idea; I just joined, and then that happened. I spent the next eight and a half years at Google. I had the privilege of leading the design on Google Calendar for a bit and led the design and research team for Google Enterprise, which became G Suite and Google Workspace. I had an amazing career there, learning a lot and working with brilliant people. After Google, I left for the startup world. After a short break, I did a startup, which I call three and a half years of getting the crap kicked out of myself. Then I went into consulting, as one does after a failed startup, for a couple of years before starting Xano. That’s been the trajectory. At Google, I evolved from a UX person to a product person, and after doing a startup, you become more horizontal across the business.

    Nataraj: I have this thesis about software products: cracking the right software product is about finding the right abstraction layer at which people want to work. Exploring Xano, your background makes sense. Someone like you starting Xano makes sense; you need an eye for what level the product should be designed at.

    Prakash Chandran: That’s a keen observation. One of the main pains I felt during my startup was my lack of control as a design and product person over the engineering process. You have to pay for an expensive engineer. They’re kind of like a car mechanic. If they tell you something is going to take a month to make and tens of thousands of dollars, you just have to believe them and hope that it works out.

    Nataraj: With that, explain what Xano is.

    Prakash Chandran: I always knew that was a painful process. Then I learned that 80% of the time and resources in software development are spent on the backend. So, Xano is a scalable no-code backend. For those who don’t know the no-code space, it’s about helping people create software without knowing how to code. No-code has been around for a long time; a tool like Squarespace is considered no-code for website building. It’s gone through a couple of different iterations. We’re part of a new wave of no-code where you can build anything and scale without limits. We 100% focus on the backend—the server, the database, the API layer—and we connect to any front end you want.

    Nataraj: What kind of applications does Xano enable people to build?

    Prakash Chandran: Xano is really meant to be a visual programming language. It’s Turing complete. Anything you can articulate in a software programming language, you can do in Xano without code. In terms of the types of applications we see built, we see everything from a dog-walking application all the way up to a customer advocacy platform at a big company like Qualtrics. It’s kind of like asking what you can build with JavaScript; the use cases are endless. In the same way, we see our customers building many types of things on Xano.

    Nataraj: One of the assumptions people often have when they hear a product is categorized as no-code is that it might be good for experimentation, but not for running production applications. Can you really go from a demo or a hobby project to actually running something that makes money or building a company on top of it? How do you see Xano fitting in?

    Prakash Chandran: I always say that no-code and low-code have some baggage associated with them. This is because the no-code vendors and tools of the past have had limitations, generally around scalability, security, reliability, and compliance. The hesitation is that no-code is something you should just prototype and tinker with, not take seriously at scale. But as I mentioned, these next-generation tools are architected fundamentally differently. For example, as a no-code backend, we are architected differently than some of our predecessors that might look like a spreadsheet on steroids, where scalability and compliance are layered in as an afterthought. We were architected from the very beginning to be enterprise-grade, portable, allowing you to move it to your own infrastructure and control the resources yourself. The flexibility in what you can build was also addressed very early on. The concern is definitely valid, but one of the things we hope to do is break that stereotype and show that you can start with no-code tools like Xano and scale without limits.

    Nataraj: While exploring Xano, it almost felt like… because I was a backend and frontend engineer, I’ve played around with different backend stacks. One of the problems I see is that building a small application is getting really complicated, even for seasoned developers, because things are so rapidly changing. It’s becoming more complex even to get started. What is your thought process on this? Am I just a bad developer, or is this really happening?

    Prakash Chandran: No, not at all. You call out something that’s pretty important. As we’ve introduced new technologies to handle different use cases, especially on the DevOps or site reliability side, it gives the consumer more choices, which leads to confusion. The most important thing when building software as a business is validating it in the market. You want to get it out the door. We believe vendors should be responsible for making good long-term decisions regarding infrastructure and DevOps, so you can focus on the business logic and your relationship with customers. The more quickly you can do that, the better. You’re either going to fail and learn and then iterate, or you’re going to get it right and scale your business on something you can trust. A general rule of thumb we tell everyone is you’re always going to rebuild. No matter what stack you build on, you’re going to rebuild it at some point. So the stack you can use to iterate the quickest is probably the best one. We wanted that to be true to our spirit, but on a trusted infrastructure, so if they did find product-market fit, they could rely on it to scale with them.

    Nataraj: Whenever I talk to early-stage founders, what they start with and where they end up is slightly different. Talk to me about the process of finding product-market fit for Xano.

    Prakash Chandran: We generally knew that this no-code, low-code space was growing. More people were turning to it despite its limitations because there’s more demand than there are engineers. We saw this limitation on the backend regarding security and scalability. So we made two decisions. One, we decided to 100% focus just on the backend and not do the full stack. This was the non-obvious thing everyone said was probably not a good idea. The second piece is we decided not to abstract away the core principles of a software development language. For example, we chose to call it an API instead of a workflow or a Zap. We chose to call it a webhook. We believe you should teach the next generation of software developers by abstracting away the code but making those concepts more accessible. Those two decisions were non-obvious. Getting product-market fit started with a landing page as we were building, saying, “Hey, this is a no-code backend. If you’re interested, sign up for early access.” Then once you have people using the product, you see how quickly they start relying on it. The next step is, will they pay for it? And over time, you see that word of mouth grow and how sticky it becomes. We got lucky in that we had this non-obvious approach and we thought it was a need in the market.

    Nataraj: Because the backend has so many components, was there a specific customer use case that gave you the confidence that you had really found something?

    Prakash Chandran: It wasn’t a specific customer or use case, but Xano was actually born out of a development agency. It started as a command-line tool to make backend creation easier without having to grow the team. When you see hundreds of different use cases, you realize most software is the same. They have the same kind of infrastructure setup, the same database. There are the same motions you’re doing over and over. For us, it was less about the specific use case and more about the procedure and those steps you had to go through just to start validating your idea. You could do this on other tools, but you couldn’t rely on it once you started to get usage and scale, or if security was a prerequisite. So that was the approach we took, and we found that being pretty horizontal has worked for us so far.

    Nataraj: You mentioned it came out of a studio. Is it from your consulting, or were your co-founders running a studio that gave you that insight?

    Prakash Chandran: My co-founders were running the development agency. I had done some consulting work as an individual for that agency. It was in doing some of that joint client work where I had seen the evolution of Xano from the very beginning as a command-line tool to a decade later, having served hundreds of use cases. I told my two co-founders, “If we took this and we productized this, I think we could serve a pretty big need in the market and we might have something special.” That’s how it came about.

    Nataraj: We’ve evolved products based on the cloud, right? We had infrastructure as a service, platform as a service, and now probably with AI, intelligence as a service. We are moving higher in that abstraction level. I was thinking at some point someone has to abstract away why everyone has to build a scalable website. You’re sort of an evolution of abstracting away that complexity from a backend perspective.

    Prakash Chandran: 100%. We could serve that use case pretty well. A lot of companies in the no-code space are very good at building building blocks, these connectors that connect one service to another. We took the other approach and built the engine and the foundation, this visual development layer on top of an engine that abstracts away the DevOps component—the infrastructure, Kubernetes, Docker, Postgres. You don’t have to worry about those things. So if someone wants to build, which you can do in Xano today, an Amazon.com template with the right database schema, and you want to be in multiple geographic regions, you can start with that business logic layer and the database. And then from the infrastructure side, we’re able to deploy in whatever region you want. It’s really just building the foundation where people agree this is the right layer of abstraction for business logic in the backend, and then they’re able to move it as they grow.

    Nataraj: Who is the ideal user today for Xano?

    Prakash Chandran: We service primarily the citizen developer. If you haven’t heard of that persona before, it’s a Gartner-defined persona. You can think of them as a product owner type. They’re a systems thinker, they don’t know how to code, but they need to build software leveraging low-code tools. There are also developers on Xano as well, but primarily we serve the citizen developer. Now, there’s a wide spectrum of experience. People more on the citizen side will use tools like Airtable or Google Sheets because it’s very easy to pick up. That serves simple use cases very well. We serve an advanced citizen developer who needs to graduate out of tools like Airtable when their needs require scalability, security, and reliability. That’s who we serve. And we’re constantly working to make ourselves more accessible to the broader citizen developer.

    Nataraj: Let’s talk about how you’re doing as a company. I think you raised your Series A. What is your revenue split between enterprise and SMB or citizen developers?

    Prakash Chandran: We launched in January of 2021. Since then, we’ve seen some pretty exponential growth, largely due to word of mouth. We’re just a backend, so we’re front-end agnostic. All the different front-end forums, whether it’s a JavaScript forum or a no-code front-end forum, mention us. We have over 70,000 backends that we’ve deployed. In terms of the enterprise versus self-serve split, it’s about 20% enterprise revenue, and the other 80% is self-serve. We’re obviously working right now to develop our muscle in the enterprise go-to-market motion, but for right now, we are mostly known in the small to medium-sized business space. In the enterprise, no-code is still very early in adoption, and we’re trying to prove ourselves there.

    Nataraj: How is the competition in the space, specifically at the abstraction layer you are operating at, focused on the backend?

    Prakash Chandran: There’s a spectrum between citizen and developer, and then a spectrum from developer to engineer. We service the upper end of the citizen developer into the midway point of becoming an engineer. In that space, there are a number of different tools. When you think about the backend specifically, if I’m going to pick the number one competitor, I think we serve different markets, but we definitely see them, is Supabase. Supabase is basically Postgres in the cloud. They’ve done an amazing job. Great founders, they execute very well. But I think there are tools that believe making a developer’s life easier is the future, and then there are tools like us that believe the next generation of software creators are going to look more like citizen developers. We serve these two markets, but because we serve the upper end, we tend to see each other there.

    Nataraj: You mentioned you almost thought of Xano as a design language. That gave me a thought that AI could use this design language to make things happen on Xano. How are you thinking about AI intersecting with Xano?

    Prakash Chandran: I mentioned visual development because we use all core foundational software engineering principles—variables, loops, conditionals—things that every programmer knows, and we visualize that. When it comes to AI, AI understands these concepts. AI has been such a beautiful thing because it has opened up so much more opportunity and built awareness around creating software and making it more accessible. People can ask AI to generate simple applications for them. I love AI for that reason. That being said, something else is needed to pick up where AI leaves off. If I say I want to build an Uber-type application and you give the same prompt, we’re probably going to receive two different code sets. Even if we don’t, what I mean in my mind with an Uber application is very different than what you mean. In that case, we’re going to keep re-prompting until it spits out obfuscated code. What’s better is you need to pick up from that scaffolding and take a visual canvas where you can infuse your intention. We believe Xano will be the visual canvas that can pick up where AI leaves off. I think a lot of people make the mistake of saying AI is going to replace coders or replace no-code. I don’t think that’s going to be the case. They’re going to work very well together.

    Nataraj: I’m curious, what are some of the techniques you guys use to acquire new customers?

    Prakash Chandran: One thing that we’ve done very well is create lots of valuable YouTube content. If you go to our YouTube channel, you will see videos starting from, “How is software made? What is a backend?” all the way to, “How do you merge two JSON arrays?” It is very important to continually put out content because this is how people consume it these days. It’s probably our largest source of high-quality traffic. The beautiful thing about content is it just keeps giving; some of it is just evergreen. We also started running office hours, which was pretty unique at the time. Every user, even a non-paid user, has the opportunity every week to come and meet with the team and get their questions answered. If they ask something unique that can help other people, we clip that and put it on YouTube. The final thing is having a community tool that can be indexed on the questions that are answered and searched for. The chances are the problems your customers are having today is a problem a customer is going to have three months from now. It’s a mistake to have a community on Discord or Slack because all of that knowledge evaporates.

    Nataraj: I’ve seen this in other tools which became ecosystems, where you have marketplaces of people who can develop things. Are you seeing a marketplace evolving in Xano?

    Prakash Chandran: Absolutely. We already have a marketplace of developers, agencies, and coaches. We’re currently working on a marketplace where people will be able to release and soon be able to sell capability, all using the Xano platform. The ecosystem and this partner marketplace are extraordinarily important. We’re even working on a certification process because our agency partners need to separate themselves from everyone else that says they build on Xano. So we have certification programs that we’re actively working on as well.

    Nataraj: It looks like you should almost rebrand yourself to calling as a ‘backend cloud’ instead of a no-code backend. We’re almost at the end of our conversation. What are you consuming right now that’s influencing your thinking?

    Prakash Chandran: I listen to a lot of podcasts. I subscribe to podcasts like the All-In podcast, Revenue Builders, The Logan Bartlett Show, and Invest Like the Best with Patrick O’Shaughnessy. I learn something every single week. Some people will work out to music; I’m working out to podcasts. I’m listening on my commute. I’m one of those types that listen at 2x and skip around because I’m at the point where I kind of know the nuggets of wisdom I’m looking for. I’m just so grateful for the community of podcasters that have amazing guests I can learn from about management style, growing a business, or customer acquisition.

    Nataraj: Who are your mentors that have helped your career?

    Prakash Chandran: There are moments of wisdom you pull from all of these podcasts and individuals that influence you. Two people I’ve never met but who have really influenced my way of thinking are Chamath Palihapitiya, who has a wonderful framework of intellectual honesty and seeking the truth, and Dev Ittycheria from MongoDB, for his philosophy around management. In terms of in-person people, I used to work with Adrian Graham and Carl Showalter. They were at Google with me, sold their company to Facebook, and then created Seesaw. Working with them directly, they’re just brilliant individuals. They work really hard and always have this healthy dose of skeptical optimism that has taught me to build in a very measured way, where you have your head in the clouds but your feet on the ground.

    Nataraj: One final question, what do you know about being a founder that you wish you knew before starting Xano?

    Prakash Chandran: I’m very happy with all of the mistakes that I’ve made. Obviously, it’s shaped where we are today. But if there was one thing, it’s that the things that matter take time. I think when we’re younger, we’re always in a hurry. We think there might be a silver bullet shortcut and we’re always looking for it. But when you’re trying to do something impactful that will have a long-lasting impact, there’s no shortcut. It just takes day-in, day-out work, trying, and learning. It’s important to align yourself with your zone of excellence and what gets you excited because it’s going to be a very long journey. In this case, Xano is it for me. I really feel like I’m doing what I’m meant to do. But when I was younger, especially before my first startup, I didn’t really have that mindset.

    Nataraj: That’s a good note to stop the conversation. Again, thanks for coming on the show, Prakash. Really looking forward to what Xano will do in the future.

    Prakash Chandran: I really appreciate it. Thank you so much for having me.


    Conclusion

    Prakash’s journey with Xano highlights a critical shift in software development towards more accessible, yet powerful, tools. By focusing on an enterprise-grade, scalable backend, Xano empowers a new generation of builders to bring their ideas to life without being limited by traditional coding barriers.

    → If you enjoyed this conversation with Prakash Chandran, listen to the full episode here on Spotify or Apple.

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  • Shankar Somasundaram on Securing Healthcare & IoT Devices with Asimily

    The world is more connected than ever, but with increased connectivity comes increased risk. From life-saving medical equipment in hospitals to the traffic signals managing our city streets, the Internet of Things (IoT) has become the backbone of modern infrastructure. Yet, these devices are often the most vulnerable entry points for cyberattacks. In this episode, we sit down with Shankar Somasundaram, the founder of Asimily, to discuss how his company is tackling this monumental challenge. Shankar draws from his extensive experience at Symantec and his deep engineering background to explain the unique security threats facing healthcare, smart cities, and manufacturing. He breaks down the complexity of securing these heterogeneous environments, the evolution of customer needs from simple visibility to sophisticated vulnerability management, and his journey as a founder in a highly regulated and mission-critical industry. This conversation offers a crucial look into the future of IoT security.

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    Nataraj: On the podcast, we feature interesting companies solving big problems in different sectors. You’re in two intersecting sectors: security and the Internet of Things. It would be a useful session for our audience to talk about the problems you’re solving. To level-set for the audience, can you give an introduction to yourself and your career until now?

    Shankar Somasundaram: Thanks, Nataraj, for having me. I’m Shankar. I started Asimily a few years ago. Asimily is focused on helping provide visibility and security for medical, IoT, and OT devices. We work across verticals like healthcare, smart cities, universities, and manufacturing. Healthcare is our prime vertical where we started the company and have since expanded. Prior to Asimily, I ran the IoT business at Symantec for a few years, which is where I got exposed to IoT. Before I even started the business, I did a full strategy project for Symantec on how they should expand into the IoT vertical. My journey in IoT has been going on for 13 or 14 years now. It started as a strategy project, which led to a few other things, and then Symantec started a business and asked me to run that group. Eventually, I reached a point where I wanted to start Asimily. Before that, I had a product and engineering background. I built the iPhone 3G modem many years ago and some of the early chipsets and algorithms at Qualcomm. I’ve mostly been on the product and engineering side. I like the space I am in because there’s a lot of innovation possible, which aligns well with everything I have done so far.

    Nataraj: Going back a little, what was the idea when you were first thinking about starting Asimily? What was the forcing factor and the big problem you were trying to solve?

    Shankar Somasundaram: When I was at Symantec, I saw the opportunity in healthcare. The initial idea was focused there, and we did a lot of work for many years. The big problem then was that healthcare is a very complex, heterogeneous environment. I call it a system of systems because it’s not just what’s happening inside the organization; it’s the suppliers and vendors. It is the one environment that singularly contains all kinds of devices: medical, IoT, and OT. I don’t think any other environment has everything. In that kind of environment, how do you provide visibility, vulnerability management, detection, and all kinds of operational metrics? And you have to do it in an environment that is very constrained, fairly regulated, and where there are severe patient impacts if you get it wrong. It is the most challenging environment I know among all verticals. I saw a couple of players in the space taking a very IT-centric approach, but there had to be a completely different, bottoms-up approach to solve for these unique devices. I said, we’ll go solve this problem in healthcare, and we can do it better than anybody else. That’s how the company began. Symantec wasn’t as interested then in going after this problem, and I decided if they weren’t going to do it, I would.

    Nataraj: How does Asimily help its customers today? It’s a primarily security-based product, but healthcare is such an interesting space in terms of software. How do you connect the hardware monitoring to the existing software used in healthcare?

    Shankar Somasundaram: Our system’s principle is the same whether it’s healthcare, smart cities, universities, or manufacturing. In healthcare, we’ve done a ton of work. We put a hardware appliance inside the environment that connects to the network and collects and extracts device-related data. Because of HIPAA, GDPR, and other regulations, you cannot transmit patient information outside. So, we transmit only device-related information to our cloud, or we have an on-premise version. There, the data gets processed for more than just cybersecurity; we provide visibility, operational metrics, and we are adding new capabilities that go beyond cybersecurity. The data we collect then integrates with other systems. We have APIs with configuration management systems, CMDBs, asset management systems, vulnerability scanners, SIEMs, NACs, firewalls—you name it. Our system does a ton of work by itself, but we interoperate with other systems, creating an integrated view for the health system, city, or manufacturing plant. We provide a high level of data granularity, deep visibility, and robust capability around vulnerability management and incident response, which improves their overall posture and enriches other systems that lack the context of these devices.

    Nataraj: You mentioned Asimily has a hardware product that collects data from other devices. How are you interacting with those devices? Is it through the firmware on the other hardware?

    Shankar Somasundaram: To be clear, we are a software company. The hardware we use is just a commodity; we can also put our collector as a virtual machine in their environment. We are collecting purely network data. We have other non-network mechanisms, like collecting manufacturer documents, but the primary method is passive, where data is fed from the network into our box. We don’t have to interact with the hardware directly because we’re not interrogating these devices. For medical devices, it’s very risky to interrogate them. For certain kinds of IoT and OT devices, you can, but mostly you are getting data from these devices on the network. Based on that data, you act on them without directly interacting with the hardware’s firmware.

    Nataraj: Healthcare is notorious for security attacks and being prone to hacking. We often hear about healthcare organizations being hacked and held for ransom. Do you see that as a common pattern you’re helping to solve? What types of issues are you solving for customers?

    Shankar Somasundaram: Cybersecurity is a multifaceted problem with no single silver bullet. Our focus is on the IOMT, IoT, and OT devices in the environment. Ransomware attacks have become more common because health data is so much more valuable than credit card data—I think 100 or 1000 times more. So, this is here to stay. Securing all these other devices is one big step toward protecting against ransomware attacks. We are a big piece of the puzzle. A hospital might have a firewall for IT systems, DLP, and an email gateway, but what about the medical and IoT devices? There are two problems: what if they’re connecting externally, and how do I protect them against internal threats? You have to assume some threats will bypass your perimeter. When they get inside, you need to know what your devices are and where attacks can come from. We do a ton of work around attack analysis, identifying how vulnerabilities on these devices could be exploited and what lateral movement could happen. We also help collect data for forensic analysis. This in turn helps protect against ransomware because medical IoT devices are the core bread and butter of a hospital’s operation. Protecting the core of the system is what we are doing.

    Nataraj: You brought up smart cities. We’ve heard this phrase and passed the hype cycle. From your observation, what does it mean to be a smart city today, and where does Asimily fit in?

    Shankar Somasundaram: I’ll rephrase ‘smart cities’ because that term has been used so many times. I think the concept is simpler: more devices are getting connected. For example, wastewater plants, which come under the city’s purview, are fairly connected. What if your wastewater plant gets attacked or goes down? Imagine your sewage isn’t flowing anymore. That would be a nightmare. All the traffic signals in a city are connected to a central controller. What if some of them fail or get attacked? The concept of a smart city I’m talking about isn’t the futuristic one touted for 20 years. It’s simpler: all these devices, whether traffic lights, sensors, or wastewater plants, are connected. How do you understand what’s in that environment and protect it? The problems are similar: protection, visibility, and operational metrics. I think the difference between then and now is there’s a lot more focus on critical infrastructure, partly because connectivity has risen. When you reach a certain threshold, like 30-40% connectivity, it becomes important. The present reality is that devices are connected, and with that comes the need for visibility and cybersecurity management. That’s what we have solved.

    Nataraj: You mentioned catering to clients in healthcare and smart cities, both of which are highly regulated. You mentioned HIPAA, which I know from a past job can be complicated. What was the experience like dealing with two highly regulated sectors?

    Shankar Somasundaram: The good news is that we touch device data, not patient data. Regulations focus on patient data, PII in smart cities, or confidential information in manufacturing. We aren’t touching that, so it’s simpler. The architecture we built, where we only send certain kinds of device data to the cloud, helps. For very critical environments where customers won’t allow anything to be transmitted to the cloud, we also have an on-premise version. Because of these architectural capabilities and our focus, regulations don’t directly impact us. However, because these are more regulated environments, there is far more scrutiny on the technology and the product. You have to have an enterprise-grade product, which is something we have built. There are certain levels of quality and assurance you have to provide in these verticals, which we have been able to do.

    Nataraj: You mentioned you got started with Asimily because you were writing the strategy paper. When you decided to start this yourself, what were those initial days like? How did you bring together the founding team?

    Shankar Somasundaram: It was pretty challenging. When you leave a large company where you’re running a business and then suddenly you’re all by yourself, it’s tough. Initially, I was lucky to have built some core advisors and relationships. One of the ex-CEOs of Symantec, Mike Brown, is an advisor and investor. I call him our first co-founder. He was one of the first people I spoke to about it, said it was a good idea, and even gave me a check. One of our investors, Ashmeet from Engineering Capital, wrote our first check. He took a bet on me when I had nothing but some slides. I would almost call Mike Brown and Ashmeet our co-founders. I got the backing of people who believed in me through previous relationships. Then I was able to reach out into my network. I brought in Hitesh, whom I had studied with at Rutgers, and he’s still with us. Then we brought in some other people and expanded the network from there. We’ve since built a very strong leadership team, mostly from Symantec and other areas. It’s a struggle initially, but I was fortunate.

    Nataraj: How did you get your first customer? When you work in big companies, there’s a whole sales system working for you. As a product builder, your job ends at supplying information to marketing and sales.

    Shankar Somasundaram: Because I had been in the industry and doing IoT, I knew a few people. I was able to reach out to some partners and people in the industry to get feedback. When I got feedback, some people said it was a good idea and to come back when I had a product. It took us a little time to get there, but once we had something, I could go back and show them. It wasn’t easy at the beginning because healthcare has a very high bar; they don’t buy half-baked products. They want a more sophisticated product even in the first round. It took us a couple of iterations, but the product had and still has some very core differentiators. That allowed us to get some initial customers. Then we were able to improve the quality to an enterprise-grade level. Through the contacts I had built, the quality we had built, and the differentiators we created, we were able to land our initial customers.

    Nataraj: How does the sales process look today compared to then? What is your process for reaching customers?

    Shankar Somasundaram: The very first sale was just me. But now, we have a full-fledged sales team, a channel team, a marketing team, and solution engineers. We also have partners. It’s a very different motion now. Our partners refer us, and being the number one rated Gartner vendor helps, so people sometimes reach out. We are constantly getting customer feedback, and we have some very strong, loyal customers who refer us. Our sales process is now largely channel-first. A lot of our business comes through our channel, and we want to encourage that. At least in healthcare, a lot of people know us. In non-healthcare, we have a channel ecosystem in place. So, between our sales channel, our existing relationships, and the credibility we’ve built, that’s what’s driving many of the leads. It’s a more formal, defined sales momentum, whereas the very first sale was completely ad hoc.

    Nataraj: When you’re talking to prospective clients, who are the decision-makers, either in healthcare or smart cities? For example, with cloud products, it could be a top-down decision from a CIO or a bottom-up decision from developers.

    Shankar Somasundaram: It does depend, but I would say 80% of the time it’s the CISO, the Chief Information Security Officer, or someone in that area like the CIO who takes care of IT and cybersecurity. Beyond that, there is some dependency on the vertical. In healthcare, it could be the Chief Clinical Officer or Biomed. In smart cities, it could be someone who manages operations. In manufacturing, it could also be someone who manages operations. There is some nuance to every vertical, but the common thread across all of them is the CISO.

    Nataraj: I think of Asimily as a security company, but security is such a broad term. Can you give an idea of the layers in this industry, who’s capturing what value, and where you position Asimily?

    Shankar Somasundaram: We are focused on device-related security—IOMT, IoT, OT. Security has different layers like data security, network security, and email security. We are focused on the non-IT side. In the non-IT world, there is a different kind of value chain. There are part suppliers, full device suppliers (like someone who provides a traffic light or an ultrasound), and system integrators who put the entire network together. There are also people who manage and maintain these devices, which can run for 10 to 15 years. Then there’s an IT infrastructure, networking, and cybersecurity overlay. We come in after these systems have been connected. We fall into that IT, networking, cybersecurity, and even maintenance layer, because we provide some metrics that help with maintenance. A lot of what is done in these industries is manual. Our value proposition is to automate much of that and bring them to a similar state of capability as the IT side. That’s where Asimily fits in the value picture.

    Nataraj: You mentioned being number one in Gartner. How do you think about competition and differentiate Asimily from other companies doing similar things?

    Shankar Somasundaram: There are players in this space, but I feel there’s a lot more innovation to be done. We are launching two completely new modules now that are the first of their kind in the industry. I feel the industry is at 50-60% of where it needs to be. What eventually needs to happen is a much broader, wider set of capabilities. When I started Asimily, all people wanted was visibility. That’s still a big problem, but now people are asking for more. They’re asking for more and more with every passing year. They want to manage all their devices with similar parity to IT devices. So one level of differentiation is innovation. I think in a space like this, similar to AI, the winners will be decided over a 10-12 year timeframe as innovations play out and customers pick more capable, mature, and holistic platforms. The other place we differentiate is depth. Whether it’s inventory, vulnerability management, or incident response, we have some core differentiators. For example, everything is vulnerable, but which vulnerabilities can be taken advantage of by an attacker for that device in that specific environment? How do you mitigate it if there’s no patch? We have unique approaches to mitigation and remediation. So, depth of capabilities and continuous innovation are what will determine the winner.

    Nataraj: Security and the IoT space are huge. If you were to look at some white spaces for a new founder interested in security, is there any area you would suggest they look into?

    Shankar Somasundaram: It’s hard for me to say because I’m so focused on this. If there was a white space, I’d go to RSA and there would already be 10 companies attacking it. You could have said GenAI is a white space, but what if GenAI starts to misbehave? Now I see five companies doing GenAI security and compliance. This question is probably better suited for a VC who is looking at all spaces. But I do think a lot of things are happening in AI that open up a ton of opportunity in security. GenAI security is just one aspect. There’s an entire suite around data loss prevention and sandboxing around it. I think that will open up a ton of opportunities, and the companies I’ve seen are still scratching the surface. Then there will be something new that comes next year and that will open up another Pandora’s box.

    Nataraj: Speaking of GenAI, are you using it in any way to improve your own startup’s productivity, not just as a business offering?

    Shankar Somasundaram: Yes, we are using GenAI. We have some partnerships with some of the larger companies releasing GenAI tools. We are using it for our own internal productivity. We actually adopted a form of AI long ago for some of our research, building our own NLP algorithm to improve our research abilities. We have used GenAI more recently to improve our productivity, DevOps processes, and internal research. Beyond that, we have always been using AI in the product, even though we haven’t created a buzz around it. As GenAI comes in, it’s just an evolution for us. We’re introducing it into our engineering productivity and also have some uses in our product.

    Nataraj: Are there any specific products or companies you’re using that you can mention?

    Shankar Somasundaram: Right now, we are partnering with the big companies. We have a deep partnership with Google and we’re doing some work with Microsoft. We’re using those kinds of tools internally for our own productivity purposes. We never feed them any customer data; that’s a strict no. We use it for our own productivity, and as GenAI has evolved, we are continuing to evolve our own algorithms because there’s more scope to do so. But partnership-wise, we are leveraging some of the bigger, more established AI models to improve our productivity and go faster.

    Nataraj: And is the productivity gain meaningful? I’m asking because there’s so much hype in the news.

    Shankar Somasundaram: That’s a good question. If you ask me this in three to six months, I’ll have a more concrete answer. You’re right, there’s a lot of hype. We’ve asked ourselves internally if paying for these tools is really improving our productivity. Is it a 5% gain for all the work we are doing, or is it truly making us significantly better? We decided to try it out. We’ve been running this and we’ll see over the next two or three quarters and get an answer on how much better and faster we can move. I don’t have a real quantifiable answer right now, but it looks promising. We have to see whether it works for us or not.

    Nataraj: We’re almost at the end. I have a couple of quick questions I ask all my guests. First, what are you consuming these days? What are you reading or listening to?

    Shankar Somasundaram: I listen to some general podcasts like Masters of Scale and sometimes read Andreessen Horowitz’s content. As the company is growing, I’m trying to understand how to scale by talking to people in the industry who have grown bigger companies. My focus is on how the company scales—what happens when it grows bigger and larger. We’re operating internationally and growing every year. So I’m looking at that, and there are some podcasts and go-to-market books on that topic. But a lot of my thinking also comes from talking to mentors and people. That’s how I learn fastest—not necessarily reading or listening, but talking to people in the industry. I’m also part of some CEO forums, and our investors introduce us to other people.

    Nataraj: Who are your mentors that have shaped your career?

    Shankar Somasundaram: There are too many to name over my entire career. But specifically for Asimily, like I said, the company doesn’t exist without Mike Brown and Ashmeet Siddharth. Thanks to them. But over my career, many other people have gotten me here. I wouldn’t be a quarter of where we are without these mentors, and also the people you work with—your team members.

    Nataraj: One last question: what do you know now about starting a company that you wish you knew when you started Asimily?

    Shankar Somasundaram: That it’s going to be harder and take longer than you anticipated. You truly realize what that means when you run a company.

    Nataraj: That’s pretty much what every founder says. This was a really fun chat, Shankar. Thanks for coming on the show and sharing your story.

    Shankar Somasundaram: Thank you, Nataraj, for having me. Thank you so much.

    This conversation with Shankar reveals that securing our connected world isn’t just about technology but about a deep, contextual understanding of each unique environment. As industries from healthcare to smart cities continue to evolve, holistic security platforms like Asimily will be essential in protecting the critical infrastructure we all rely on.

    → If you enjoyed this conversation with Shankar Somasundaram, listen to the full episode here on Spotify or Apple.

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  • The Product-First VC: SC Moatti of Mighty Capital on Picking Winners

    What does it truly mean to be a ‘product-first’ venture capital firm? In a world saturated with startups, identifying companies with genuine, sustainable product-market fit is both an art and a science. We had the pleasure of sitting down with SC Moatti, the founder of Mighty Capital, a VC firm built on this very principle. With a rich and diverse background spanning academia, entrepreneurship, and now investing, SC brings a unique perspective to the table. In this episode, she delves into her decision-making framework, what distinguishes a great product from a great product manager, and the essential skills needed to succeed in today’s tech landscape. She also shares insights from her experience teaching at Stanford and serving on boards, offering invaluable advice for founders and aspiring investors alike.

    → Enjoy this conversation with SC Moatti, on Spotify or Apple.

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    Nataraj: You have a really interesting, diverse set of experiences. You have an overlap from academia, you did your own startup, and you’re also doing investing. Very few people have these interesting vantage points. I thought it would be great to have you talk about product development, venture capital, and your experiences. To get started, can you give a little background on what you have done in your career for our audience?

    Nataraj: Are all the companies that you mentioned investments from Mighty Capital, the fund that you’re running, or are they angel investments?

    Nataraj: Talk to me a little bit about how you are making decisions. Everyone has their own frame of decision-making, especially in the early stage. When you say “product-first” and identifying product-first companies, what does that mean in practice?

    Nataraj: How many investments does a fund make? Is it like a traditional venture fund where each fund is making 30 or 35 investments per fund?

    Nataraj: Does Mighty Capital operate like a traditional fund where you’re making 30 or 35 investments per fund, or are you operating in a different model?

    Nataraj: You’re also teaching at Stanford about startups. Can you talk a little bit about what you teach and what that experience has been like?

    Nataraj: What are some of the mistakes?

    Nataraj: What does it take to be an effective board member when you’re investing at a Series A stage?

    Nataraj: One of the things we keep hearing in terms of governance and startups is because of this dual-class shareholder system, there isn’t a lot of control on the board’s side. Is that how your experience has been? Is that a real trend or is that just people who don’t understand things talking about it?

    Nataraj: A common commentary around startups and boards has been that the boards don’t have full control because of dual-class shareholders and they can’t really have a real implication on what the founder is doing. Do you believe in that, do you see that changing, or is that just not the right way on how things actually happen?

    Nataraj: You also mentioned your students come with a lot of exposure to public investing. What is your take on how much focus there is on looking at data when you’re doing early-stage investments, given there isn’t much data available?

    Nataraj: To follow up on that, are there any specific things that you as an investor focus on more? For example, in my case, when I do pre-seed investing in SaaS, one important factor I focus on is whether one of the founders can really write great code or execute faster. That is one point I definitely want to have. After years of figuring out what a great pre-seed startup looks like, I’ve found that the only thing that really matters for me is this. Do you have certain criteria or things that you, through intuition or experience, focus on?

    Nataraj: It’s amazing. I’ve faced this when we are trying to get into a pre-seed round and some large investor comes and takes the round; that’s a very common scenario. I think 80% is pretty high, especially when you’re co-investing with such large brands. I want to get back to the notion of what makes a great product. I know you’ve written a book on it. I want to split this into two parts: what makes a great product, and what makes a great product manager?

    Nataraj: I definitely agree that one of the best ways to start a startup is to come with a big idea rather than a small one. Take a big idea, but create a smaller approach to that big idea. A lot of entrepreneurs misunderstand that and they pick a niche category thinking that it will blow up into a big category, but eventually, they realize that fundraising will become hard because there’s no bigger story to tell. If someone is starting out to become a product manager, what are the meta-skills that they should focus on to become a better product manager or product builder?

    Nataraj: We are almost at the end of our conversation. I wanted to ask a couple of questions that I ask all my guests. The first one is, who are the mentors that shaped your career or helped you progress?

    Nataraj: You can give names or books or partners you worked with that helped in your career.

    Nataraj: Do you have any favorite books that you go back to or are actively reading right now?

    Nataraj: If someone recently graduated and wants to get into product management or investing, what would be your advice for them?

    SC Moatti: There is going to be more to learn and more to do. But getting started on why you’re here on earth, what you are here to accomplish—you’re ready for that faster than you think.

    Nataraj: What is the best way for the audience to reach out to you?

    SC Moatti: I’m very easy to find on LinkedIn and on social. And if you want to drop me an email, it’s sc, just my initials, at mighty.capital, no dot com.


    This conversation with SC Moatti provides a clear and actionable framework for understanding what it takes to build a successful product and company. Her insights into the mindset of a product-first investor are essential for any founder seeking to navigate the venture capital landscape.

    → If you enjoyed this conversation with SC Moatti, listen to the full episode here on Spotify or Apple.

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