The ROI on AI is obvious in these industries
Rudina Seseri is the Founder and Managing Partner of Glasswing Ventures, recently named one of America’s Top Venture Capital Firms of 2026 by TIME and Statista. With a focus on early-stage AI-powered companies, Rudina has been investing in AI since 2016 and has always been ahead of the curve. Host Rana el Kaliouby talks to Rudina about the shifting AI investing landscape, where she sees the real value in AI, and what she looks for in a founder before she writes her first check.
About Rudina
- Founder & Managing Partner of Glasswing Ventures, leading early-stage AI investor
- 20+ years investing in enterprise, security, and frontier technologies
- Backed multiple notable exits incl. Oracle, Google, and Veritas acquisitions
- Serves on boards of M&T Bank and MSC Industrial Supply
- HBS Executive Fellow, MIT Connection Science Fellow, MA AI Task Force member
Table of Contents:
- Why founders need direct advice and trust
- How AI investing changed the rules of venture
- When to back young founders before they are ready
- Where vertical AI creates durable enterprise value
- Why governance and new models matter now
- How Boston can win in physical AI
- Lessons from missed deals and founder loyalty
- How AI is reshaping the work of VCs
- Episode Takeaways
Transcript:
The ROI on AI is obvious in these industries
Note: Transcripts are automatically generated from episode audio, and are not fully corrected for spelling, grammar, and formatting.
RUDINA SESERI: We back a lot of founders, and one of the questions we ask is: Are they open to advice? In an environment like this, where capital feels like the commodity of commodities, how do you assess that? How do you build that trust up front so they know this is not just a transaction, that there is more that comes with it?
RANA EL KALIOUBY: What is the biggest mistake you’ve made as an investor?
SESERI: I love all my companies, and anything you know about investing tells you that you need to focus on the winners. It goes counter to how I’m wired. That is a constant struggle. I’ve gotten better at it, but it is not how I’m wired.
EL KALIOUBY: What is the one that got away?
SESERI: Depending on the day you ask me, it’s Perplexity, because we saw it many times and passed on it because it was really a thin-layer wrapper, and we were looking for more of a moat.
EL KALIOUBY: And that’s why you said, “Depending on the day you ask me,” because —
SESERI: Because there are days when you’re like, “Yep, I called it. OK, great. I don’t feel so bad.” And there are days when you go, “Oh, my God.”
EL KALIOUBY: That was Rudina Seseri, founder and managing partner of Glasswing Ventures, an early-stage venture capital firm investing in AI-powered companies. From AI automating prescription fulfillment to AI reinventing cybersecurity, Rudina has always been ahead of the curve. Today, I’m talking to Rudina about the AI investing landscape, where she sees the real value in AI, and what she looks for in founders before she writes that first check. I’m Rana El Kaliouby, and this is Pioneers of AI, a podcast taking you behind the scenes of the AI revolution. Rudina, welcome to Pioneers of AI.
SESERI: Thank you for having me, Rana.
EL KALIOUBY: I am so excited for our conversation. First of all, congratulations, because you and Glasswing Ventures were named one of America’s top venture capital firms of 2026 by Time and Statista.
SESERI: Thank you.
EL KALIOUBY: That is great.
SESERI: Lots of hard work, but backing the right founders, dollars in, returns out. Along the way, it’s nice to see this.
Copy LinkWhy founders need direct advice and trust
EL KALIOUBY: That’s awesome. I want to start with a personal story.
SESERI: OK.
EL KALIOUBY: This is about six years ago now. It was the fall of 2020, during COVID. I took a walk by a river close to where I live, and I was really thinking about the fact that it had been 10 years since I was running Affectiva. You remember?
SESERI: I know where this is going.
EL KALIOUBY: I was like, “I just need some advice. Who can I call?” And I texted you on my walk and said, “Rudina, do you have a few minutes?” You were, on the spot, like, “Sure. Call me.” At the time, I was contemplating whether to raise an additional round of funding for the company or explore exits.
We hopped on a call, and I asked for your advice on what to do. Do you remember that?
SESERI: I remember. I know exactly where I was sitting as well.
EL KALIOUBY: Yeah. Where were you?
SESERI: I had turned one of the bedrooms into an office, so I was literally sitting at the desk in front of the computer.
EL KALIOUBY: Do you remember what you told me?
SESERI: I do. I said, “At some point, make a call. You can keep going and going, but,” in so many words, “make the tough decision and get it done.”
EL KALIOUBY: Yeah, that’s exactly right. I think the thing that struck me was the clarity of your answer. Sometimes when people give advice, it’s wishy-washy, and you were very Rudina-style. Because I’ve gotten to know you fairly well since then, you just said, “You’ve been doing this for 10 years. It’s time for a new chapter.”
SESERI: Yeah.
EL KALIOUBY: “Just get it done.” It really helped clarify what I wanted to do next.
SESERI: I think it was particularly evident to me at the time because you had done all the hard work. It was just a question of whether you had taken it far enough.
EL KALIOUBY: Yeah.
SESERI: And it’s your baby. I know a thing or two about starting a firm with Glasswing, and it’s very, very hard to let go. But you hit the success point. Time to call it.
EL KALIOUBY: So do you get a lot of these calls from founders?
SESERI: I do. I usually get them in the context of my own founders or founders that I’ve backed previously who are trying to figure out what to do next. It’s funny because we back a lot of founders, and one of the questions we ask is whether they’re open to advice. In an environment like right now, where capital feels like the commodity of commodities, especially with younger founders, it often becomes a one-term negotiation around valuation. How do you assess that? How do you build that trust up front? I talk about paying it forward so they know this is not just a transaction. There is more that comes with it. Invariably, you see that more pronounced in a positive way with founders who have gone through that journey before and know that who you partner with, in terms of a backer, is not just about valuation and not even just the brand of the firm. It’s actually a lot more nuanced. It’s the person you pick and what they will do when the going gets tough. Will that VC be there for you?
EL KALIOUBY: Yeah, absolutely. OK, you’ve been investing for a long time. I am now an investor. I took your advice, and now we’re both investors.
SESERI: Yes.
EL KALIOUBY: And I believe we’re actually co-investors in one company.
SESERI: Yes.
EL KALIOUBY: Yes.
SESERI: And some of us have a little bit of a stake in some of you.
Copy LinkHow AI investing changed the rules of venture
EL KALIOUBY: Yes, exactly. You are an LP in my fund. Thank you for the support. I really appreciate it. I would love your take on what it’s like to be an investor in today’s AI landscape. My sense is every company is an AI company, and every investor is an AI investor.
SESERI: It’s an incredible environment. The closest sentiment to what I’m experiencing, and what we’re all experiencing right now, was in 2000. But even then, I don’t think it was as pronounced as it is today. There is a lot of innovation going on. With AI, building is no longer the challenge. Building is not the moat. We can all build. I sat down two weeks ago and wanted to create an app, or an artifact, or whatever we want to call it these days — an agent whereby I could see all the audition opportunities that would come in Boston. I wanted an entire format. Bam, bam, done.
EL KALIOUBY: Done.
SESERI: That’s not the advantage.
EL KALIOUBY: Right.
SESERI: When you had talent that was building, you had a different type of moat. Today, I think the advantage is more around the data and the access, the totality of building systems, because I think models and building in and of themselves can be commoditized. If we’ve seen anything, it’s that you swap one model out and replace it with the next. But it’s the data-and-architecture combo, and to what purpose, and how deep you can go in that space. So tying it back to the founders, there’s a lot of demand now for the infrastructure layer, particularly around GPUs and what sits on top of that. You see tons and tons of those companies, and they’re able to raise a lot of money. You have to decide, am I in for the journey or not, with very little data. But you also don’t have the luxury of saying 18 months from now we will be able to call it one way or another, because raises are 50 and 100 million, and everything is sort of geared toward setting up a lab. I’m being a little euphemistic. I don’t think everything is a lab, but many labs are being funded, so the time for the winners and losers to emerge is going to take longer. So it’s a very different model. It’s also very different from what you and I do, liking to be the first check in. How do you become the first check in, roll your sleeves up, and help build the company when their first raise is 30 million? The economics don’t work. So we’re thinking very carefully about how we tackle that, and I don’t think anyone has a good answer right this second. But I think we have ideas on how we go very early and make it so easy and bespoke for founders to build the business faster than they otherwise would that we might be able to get into that incubation stage.
EL KALIOUBY: This is interesting because I was looking at our portfolio, and it’s almost bifurcated into two buckets. One is typical pre-seed and seed stage, so the valuations are under 15 million. We come in early. The companies are early. And then we’ve made a decision to also invest in these horizontal AI, bigger physical AI infrastructure companies. Their early rounds are like $100 million, at billion-dollar valuations, and we’re a small check, but we still decided to do these because I think there’s a lot of upside. How do you think about valuations, and how do you evaluate?
SESERI: They’re important. They’re not everything. That’s not really how I think about valuations. You want to be part of the bigger journey. So the way I think of it, almost like different products, we have this access check where we’ve gone into some of the biggest robotics companies around town and beyond, in the physical AI space. We’ve invested in Unconventional AI, in Recursive AI, and a bunch of other 100 million-, 200 million-type raises, 500 in some instances, where we want to have a seat at the table for access not just to the deal and potentially follow-on capital with our LPs, but also to the ecosystems that spin out. It’s the whole community, the whole machine. So that’s one piece. The other piece is the redefinition of seed, pre-seed, incubation, formation, whatever flavor-of-the-day label one wants to give it. I’m pretty convinced that the seed round now represents the old A. The old A was 8 to 10 million. Many, many seed rounds are in that range, maybe 6 to 8, but many others are just raising 30 and 50 right off the bat, right? So true early stage hasn’t come to where seed is, and seed has gotten later stage, and no founder wants to take capital in between. This is a very interesting dichotomy. So by design, you try to tap into both, knowing that you’d better be investing in a company that’s de-risked enough if you’re writing a bigger check, and then in the smaller ones, that you will do a lot of sweat, blood, and tears, heavy lifting alongside founders. And those are fun. It’s just that you have to do a lot more of those because the failure rates will be higher.
Copy LinkWhen to back young founders before they are ready
EL KALIOUBY: I don’t know if you saw this program, Tech Trek, that came out of —
SESERI: Yes. John Werner.
EL KALIOUBY: Yeah, exactly. I’ll just give a summary of what it is. They basically selected a number of students from MIT, Harvard, and Princeton and sent them to the West Coast to spend the summer there. They all lived in a house together and built their start-ups, and they came back, did a demo day, and some of them were really interesting. We were starting to meet with them to see if we want to invest in them. I would love your thoughts on this because most of them are undergraduates or just freshly out of school, so they have very little business experience. Part of me is excited to back this young, super-ambitious talent, but I have question marks about their commitment to the project or the start-up because some of them are still maybe taking a leave of absence from school, but they might want to go back. As a parent, I’m a little biased. I would love for them to finish school. Have you backed that kind of founder?
SESERI: Oh, yeah. On my way here, I was talking to Tune from Provenance, and I think he’s a junior. He’s dropping out, and he had a full merit scholarship. They’re basically trying to become the platform for analytical financial-model presentations, so it’s a really interesting take with their AI. It’s funny you say that because the first thing I will say is, “Oh my gosh, your poor parents.”
EL KALIOUBY: Right.
SESERI: So it’s just that notion.
EL KALIOUBY: Or not. I mean, if they do great, amazing.
SESERI: Not everybody’s motivated by money, though.
EL KALIOUBY: Yeah.
SESERI: I grew up in a culture — I’m Albanian — where education was your most precious asset.
EL KALIOUBY: Same.
SESERI: It was a gift because no one could take it from you, especially in a country like mine, where they had communism. Wealth was taken. What was private became government-owned. So some of us are wired in a way where education is close to religion.
EL KALIOUBY: That’s giving me goosebumps because I have the same wiring, clearly.
SESERI: Yeah.
EL KALIOUBY: Yeah.
SESERI: So I put that aside. I have a fundamental view that’s twofold. One, there are some people who are special, and even if they don’t have the answers, no matter the age, they will somehow find their voice and figure it out. There is also a mentality that we’ve worked very hard to overcome. Ten or 15 years ago, Boston-based VCs, I would say, backed professors, and the West Coast was backing students. If you think about mobile and a lot of the application ecosystem, the innovation, the transformation, was really driven by the students rather than the professors. I think that has something to do with naivete. So I always go back to the Uber example: the kid who’s in Paris, it’s raining, and he thinks, why in the world can I not call a car or cab on my phone? That became Uber. As basic as that was, the barriers they had to overcome were things they tackled along the way.
EL KALIOUBY: Yeah.
SESERI: So there is something about that naivete of, I don’t know too much to know that it’s done this way. That has to be balanced, of course, with driving adoption and the hustle, and we go in and out of waves as backers. The downside is, I hope they know how to quickly get adopters to embrace them because there is value in the relationship. In fact, domain expertise — especially when you’re talking about a vertical domain — depth of trust, and depth of understanding of workflows could be some of the few moats that remain in AI-started companies.
Copy LinkWhere vertical AI creates durable enterprise value
EL KALIOUBY: I know a big focus of your investment thesis is vertical AI. My definition of vertical AI is basically AI-ifying legacy industries like supply chain, manufacturing, financial services, insurance, construction — all these unsexy industries where there is an opportunity to reimagine how work is being done. Where do you see AI creating value in these industries? And maybe the best way to do this is if you can give us some examples of companies from your portfolio.
SESERI: Yeah.
SESERI: So I will give you a one-two-punch answer as I contemplate it. First, there is a low-hanging-fruit opportunity set across these verticals, and that is to drive productivity orders of magnitude higher by way of understanding workflows. I think the easiest — and I’ll do that in air quotes — path to creating value is to go in and say, “Hey, pharmacy fulfillment is being done in this manner. There are five different systems that have been stitched together, different software providers. A human touches the prescription, for example, at every step of the way. It gets digitally faxed. They have to take it and type it up in the other system, et cetera, et cetera.” So that, to me, feels like low-hanging fruit, but the key is going to be having access to the deeply vertical data that exists in order to get the performance and, perhaps even more importantly, understanding the workflows. A lot of the challenges that we have in different industries are not that it can’t be done; it’s that the workflow is in the mind of somebody or in a 600-page binder that’s collected dust, and there have been hundreds of deviations from it. But if you understand it, I think that’s low-hanging fruit to drive quick productivity, enrich an experience, deliver the technology in a different way than it has previously been delivered, and make the ROI quite obvious. So I’ve just described a company called Asef in my portfolio, where that’s literally what they do, and they also give visibility into how effectively prescriptions are being filled because, little-known fact, 30% of prescriptions do not get picked up.
EL KALIOUBY: Oh, wow.
SESERI: So you’ve gone to the doctor, they’ve given you a diagnosis, they’ve given you at a minimum a treatment, if not a cure, and you don’t go pick it up. So there’s a whole process and a lot of waste there that are important.
EL KALIOUBY: One of the concerns I generally have, and that’s kind of materialized even more strongly in the last six months in the vertical AI space, is the frontier labs are moving so fast, but they’re also adding capabilities really fast. So you can imagine a supply chain company building its own Claude agent to do a lot of this work, and then these companies become obsolete.
SESERI: So I think there are two schools of thought competing right now. One is, you go deep and specialize. The other school of thought is what a lot of the agent players and large language model players like Microsoft with Fabric, OpenAI and Anthropic are saying, which is, “You can just buy us as the layer and then build the agents on top of us, and therefore you don’t need specialized tools.” I think the reality will be hybrid, as is always the case in this world. If everybody’s coding internally and building their own agents, I have a lot of questions around the long-term sustainability of those agents, the quality, the performance and compliance.
EL KALIOUBY: That’s why there’s still opportunity in vertical AI, right?
SESERI: Not only that, but it also begs the question: How else do these companies that are vertical continue to move up and down the stack, where the advantage is not that the foundation model has seen it all? The advantage is depth, trust and governance. There are all these other facets that are very, very important.
EL KALIOUBY: The other thought I had — and I’ll use the legal industry as an example — is companies like Harvey AI have developed AI solutions for law firms.
EL KALIOUBY: They have seen success. But I’m also seeing this idea of reimagining what a law firm could be.
SESERI: Exactly.
EL KALIOUBY: Like an AI-native law firm.
SESERI: Yeah.
EL KALIOUBY: Right? Where do you see the opportunities in that? Is it an and, or is it an or?
SESERI: I can make both arguments with the same level of conviction and hold opposing views, because we really, truly don’t know. I’m increasingly believing — and this is the second part of a one-two punch — that the company of the future should really start with a clean slate.
EL KALIOUBY: Yeah.
SESERI: Coming back to the law firm of the future, it could look completely different. As you look ahead, why can’t I have my legal agent there, and the lawyer just provides the judgment? I’m really focused on this judgment piece, because think about agents. A model, whichever model you pick, has been trained on all web data, and we can use that as the best digital proxy for society’s, humanity’s, data. If a human had that kind of data, they would be a sort of super-overlord source, right? We would be way smarter. The models are not. I think it’s this notion that they’re neural nets, so they’re really dealing with the brain, not with the mind. We humans, as limited as we are relative to the speed, processing, and other capabilities that agents and models have, can actually make a lot of decisions with very imperfect and limited data.
EL KALIOUBY: Yeah.
SESERI: Models are dumb.
EL KALIOUBY: That judgment still is human.
SESERI: Yeah. I think, for the safety of our species, we need to retain the judgment.
Copy LinkWhy governance and new models matter now
EL KALIOUBY: I want to move us toward more of the horizontal AI and AI infrastructure, but I’ll start with the governance and safety part. I believe that is a very important area to invest in, but we haven’t made any investments in that space because I don’t know if that’s something the labs need to take on. Is there space for companies that sit on top of the frontier models to ensure governance and safety? I’d love to hear your point of view.
SESERI: We invest actively in cybersecurity, and I would say security plus safety plus governance — and honestly, not just digital but physical security — are kind of coming together under one umbrella. So I do think there’s high demand for governance. Every enterprise is trying to figure it out. Do they go to their established security partners because they are offering a new module or a new governance agent? What do you do? For example, for my own AI usage, I get so many emails. I actually know exactly: I get 45 to 63 emails per hour.
EL KALIOUBY: Wow.
SESERI: It’s incredible. So I need some sorting and prioritizing and, in some instances, pre-filling and pre-drafting. Then I go in, sort of change it, and press send. But that means the agent gets to look at all of my content, all of my emails. So we have a company called D2 that’s basically providing that MCP security, and we couldn’t be in compliance if we didn’t have that capability applied. So it’s regulation and safety and security. I actually think that’s one of the areas that will get a lot of funding, and the demand for purchasing it, whether it’s delivered as an AI service or as software plus service, is almost indifferent to price because you must have it. This is an existential question. So it’s actually a nice area to look into.
EL KALIOUBY: Yeah. OK, great. So you have invested in Liquid AI —
SESERI: Yes.
EL KALIOUBY: Which is a frontier lab based in Boston, which is awesome. Tell us more about that and your thesis around where the opportunity is in horizontal AI.
SESERI: Ramin Hasani and the amazing Daniela Rus founded that business out of MIT. Unlike the other frontier models, what Liquid AI and Ramin are doing is actually computing at the edge. So that, in and of itself, has different ramifications for compute efficiency on the positive side. They also do something really interesting. When you think about the pipe of any sort of agentic action that gets taken, how you use the models, the pipe is hungry all the same, whether they need that full compute or not. The layperson’s analogy that I give is it’s a concrete pipe, and it doesn’t change, and you’re flowing data and compute through it, and it’s calculating and giving you outcomes whether it needed to do the whole thing or not. That’s how it’s set up. What’s amazing about Liquid is that it’s flexible — sort of the notion of liquid. So it shrinks if it doesn’t need all that compute, and it expands as it needs it. So, by default, those two facets really stand out to me because, effectively, it makes it a lot more efficient. And, by the way, for some of our kids who are anti-AI —
EL KALIOUBY: Yeah.
SESERI: It’s environmentally friendly —
EL KALIOUBY: Yeah, totally.
SESERI: And there are all sorts of other ramifications. So I think there is a real advantage, not just in performance but in what it takes to deliver that performance. I think there is a wave of opportunity with these big models, recursive AI, again with self-learning, that are pushing into the next paradigm, because at some point I do think we will run out of the improvements we can make to the large language models, and the next big breakthrough will be a paradigm shift. I think these frontier labs represent the potential for that next paradigm shift.
EL KALIOUBY: We’ve made an investment in a company called Odyssey, which is a world models company, and then we’re also investing in several physical AI companies and AI-native interfaces —
SESERI: Yes.
EL KALIOUBY: That, too, is an area that is so interesting.
SESERI: Yes. I’m actually quite excited about our local ecosystem and what we’re doing with physical AI.
EL KALIOUBY: I was going to ask you about that, because obviously we’re both Boston-based.
SESERI: Yes.
EL KALIOUBY: We invest all around the U.S. I think it’s the same for you as well.
SESERI: We’ve always had more of a tendency to stick to the East Coast, and we do West Coast investments, but more selectively.
Copy LinkHow Boston can win in physical AI
EL KALIOUBY: What is your point of view? There’s a narrative that a lot of AI is happening in the Bay Area, but what’s your view on what’s happening on the East Coast?
SESERI: I think we need to acknowledge our strengths and own them. We need to acknowledge that the ecosystem in San Francisco in particular, and even the broader Bay Area, is extremely well developed. Having the big technology companies there creates a lot of density, and that’s just the reality. Where I think we have the capability is that we have the highest-quality students and professors. We have that kind of density, too. And with initiatives like what Ryan Durkin has done with Mass AI, we’re finally waking up and taking pride in what is being built. Look at how many robotics companies there are. Look at all that is happening across industries. Let’s not worry about what we are not. I want to speak to what we are: a lot of founders, big ideas, and incredible students and undergrads. Mercor came out of where? Cursor came out of where? Where I think we need to be intentional is in capturing and supporting these teams before they move to the West Coast to build out.
I also think you are an MIT person through and through, but MIT has not been as picked over as some of the West Coast schools. So there’s also this moment in time when not only do we have density, not only do we have the drive, not only are Anantha and Sally — the provost and president — driving this renewed energy around entrepreneurship, but we also have the talent that’s still here, the ability to do both, and the desire. So I think we should capitalize on that. Again, you want to create multiple generations of students who contribute to industry and vice versa. Also, research funding has dried up, so partnering with industry becomes a lot more important than it used to. We are all asking a lot of questions, at least from the outside in. That’s my take on the future of education.
EL KALIOUBY: What do you do if Livvy, your daughter, said —
SESERI: Please don’t do this to me.
EL KALIOUBY: If she said, “You know what, Mom? I have a multibillion-dollar idea I’d rather go build,” what would you say?
SESERI: First of all, I would support it, but it cannot be at the expense of an education. So she does it before, she does it after, or she does it alongside. Whatever form education takes six years from now, it might look very, very different. I want my child — and education may be in a higher-ed form, or maybe something else emerges that we don’t even know about. But what I do not want my daughter to be is rich and ignorant.
EL KALIOUBY: Yep.
SESERI: I’d rather she be happy, well-adjusted, worldly, and informed.
EL KALIOUBY: Your daughter is very multidisciplinary, and she has a lot of interests.
SESERI: I want her to be a full human in her fullest capacity, and I want her to embrace AI to know more, to discover more than she otherwise would be able to. For many generations, higher ed has been that path. So if it continues to be, that will be very important to me. We’ll see if she listens or not, or if it’s another form, whatever form. But otherwise, we become so narrow, so focused, and with algorithms that are reinforcing by nature in terms of what information we get fed, we confuse knowledge with information, and we lose that worldly point of view that brings us together rather than separates us.
Copy LinkLessons from missed deals and founder loyalty
EL KALIOUBY: What is the biggest mistake you’ve made as an investor?
SESERI: I love all my companies, and anything you know about investing tells you that you need to focus on the winners and get the middle performers to move up. It goes counter to how I’m wired. I want to save everyone, so that is a constant struggle. I’ve gotten better at it, but I do not naturally do what this job requires.
EL KALIOUBY: Okay.
SESERI: You’ve got to put your effort where you can generate the biggest returns, because I want to support my founders. That’s why I’m on this journey. That’s why I love it. I want to see transformation. But we’re also managing money for endowments, for pension funds. Everybody’s mind goes to, “Oh yeah, it’s the rich guys’ money that you have, and you’re just making them richer.” No. It’s also the scholarships that need to be funded for families that can’t afford them out of these endowments, and they give us a piece of that endowment for us to create multifold returns. Or it’s the teachers’ pension funds or firefighters’ pension funds. This is their livelihood. So it’s very easy to say, “I’m founder-friendly,” and lose that perspective. You’ve got to balance both. But yeah, I feel so vested.
EL KALIOUBY: What is the one that got away?
SESERI: Depending on the day you ask me, it’s Perplexity, because we saw it many times and passed on it.
EL KALIOUBY: Interesting.
SESERI: My partner, Kleida, saw it many times — Kleida Martiro — and passed on it because it was really a thin wrapper layer, and we were looking for more of a moat.
EL KALIOUBY: And that’s why you said it depends on the day you ask me, because …
SESERI: Because there are days when you’re like, “Yep, I called it. OK, great. I don’t feel so bad.” And there are days when you go, “Oh, my God.” But it also speaks, in full candor, to that execution piece of how you reach the market and get adoption. In the era of mobile apps, it wasn’t that your app was so much better than mine, or vice versa. It was that you caught that virality. However it got into the hands of consumers, it was very hard for a second or third player to replicate. So there’s more to the moat.
Copy LinkHow AI is reshaping the work of VCs
EL KALIOUBY: Yeah, absolutely. How are you using AI within Glasswing? I know you’re using it in all sorts of ways.
SESERI: We have, gosh, eight AI engineers full time.
EL KALIOUBY: Wow.
SESERI: Over the last few years, we’ve actually built out what I call the Brain due diligence platform. Not only is it multi-agent, but the agents all interact with each other. There is a supervisory agent that understands the meta task, and it’s trained on huge amounts of data — though probably very little data, all things considered. But it’s an incredible tool that maintains the depth of diligence while helping us move much faster. What we have done around the AI platform has really made a difference. Basically, I would estimate it compresses about two to two-and-a-half weeks’ worth of work into half a day.
EL KALIOUBY: Amazing.
SESERI: That does two things. In environments like this, we can ramp up quickly, especially because we invest within certain theses, so we live deeply in those theses. But it also lets us line up the human experts to augment the process, and customers — why are you buying it, et cetera. So that piece is quite interesting. We also have the sourcing mechanism, which we’ve now built by pulling from archives and all sorts of different sources.
EL KALIOUBY: To predict who’s starting …
SESERI: Who’s starting.
Last week it was about 104,000 founders. This week it was over 105,000, and they get ratings. This is an attempt to basically go discover them before they tell the world. It’s a work in progress.
EL KALIOUBY: I love that. Yeah.
SESERI: Yeah, but it’s really sort of unique. It also helps you look at the founders in the last three or four years who have made it big, and you go, “What are the characteristics?”
EL KALIOUBY: What are the characteristics?
SESERI: I know. It’s been interesting. Union Square Ventures always used to say that, when it comes down to it, it’s founders who have known each other since childhood.
EL KALIOUBY: Yeah, that is so interesting.
SESERI: That’s one data point. I think it’s probably a much more complex formula.
EL KALIOUBY: If you’re listening and you’re thinking of starting your company, who’s your bestie? Start it with your bestie.
SESERI: Start with your bestie — someone you’ve known and trust. If you’ve managed to stay friends through the years, through college, separation, and all that, there’s some bond there that, when the going gets tough, can carry you through. So that has been important. But back to your question: There’s a lot around that. There’s a lot around automation of tools. Again, my email bit has been life-changing, and I think it’s only the beginning.
EL KALIOUBY: Yeah, so exciting. What do you think the job of a VC will look like in the next few years? How will AI change it?
SESERI: Judgment.
EL KALIOUBY: In the end, yep.
SESERI: In the end, I think speed of research and due diligence and all that will happen. It’s about how we weigh the analysis. Again, I think analysis will be automated. It’s about the judgment and the patterns that may not be captured in the numbers, that are hard to quantify.
EL KALIOUBY: Yeah. What are you most excited about in the near future?
SESERI: I mean, we’re changing the world.
EL KALIOUBY: We are.
SESERI: I hope we’re doing it for good, and I hope it’s human-centric. I know we are in our own immediate worlds. But yeah, I think this is bigger than the Industrial Revolution. What will the social norms be in the future? Will we need to work in the same manner? It’s an incredible idea to contemplate, and it’s not far-fetched. What do we do in new spaces, like outer space? What new avenues do we open? What does exploration look like? It’s a whole new world.
EL KALIOUBY: A whole new world. I love it. Radina, thank you so much for joining us on the show. This was great.
SESERI: Thank you for having me. Always fun.
Episode Takeaways
- Rana El Kaliouby opens with a founder’s story of calling Rudina Seseri for blunt advice, setting up a conversation about trust, clarity, and what founders should really want from investors.
- Rudina Seseri says today’s AI boom has rewritten venture math: building is cheap, moats come from data and systems, and even “early” rounds can now arrive with eye-popping price tags.
- On young founders and vertical AI, Rudina makes the case for backing ambition before it looks polished, while betting that workflow depth, trust, and domain data still create durable value.
- The conversation widens to governance, new model architectures, and Boston’s edge in physical AI, with Rudina arguing the region should lean into its talent density and stop imitating Silicon Valley.
- Near the end, Rudina gets candid about investor mistakes, missing Perplexity, and how Glasswing uses AI for diligence, while insisting the future job of a VC still comes down to human judgment.