ChatGPT doesn’t want you to email your ex

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1:45Hi, everyone. It's Rana. So today we're bringing you something a little different. Earlier this month, MIT Sloan professor, entrepreneur, and VC, Sinan Eral, interviewed me at MIT's Big AI Conference, which stands for Business Implications of Generative AI. I had an awesome time. I got to talk about my take on the AI startup landscape and how AI is changing the future of work. I also got a bit TMI and shared how I use ChatGPT as my dating coach. It was so much fun. And for today's show, I'm really excited to share this conversation with you. I'm Rana El-Khalyubi, and this is Pioneers of AI, a podcast taking you behind the scenes of the AI revolution.

2:39All right. Yes. Well, welcome. Welcome back. I know you live in Boston. Yeah, I do. But welcome back to campus. I just want to start with this transition that I think is very cool. And I want to check myself on a sort of metaphor that I like to use. Okay. So I'm also a startup founder turned venture capitalist. And the way I like to describe that experience is that when you're building a startup, it's like growing a single tree. Right. You're worried about like, where is it going to get its nutrients? So I got to get these pests away from the tree. I got to make sure it can see the canopy so it can get sunlight and so on.

3:18And then when you transition to being an investor, you're sort of more worried about the forest. So you see lots of different trees and you're like, in this part of the forest, like which of those trees is going to succeed? And how can these trees like complement each other in a way that like shares nutrients or something? Does this metaphor hold like you went from Affectiva, you're now doing Tulip. And so I want to know, I don't really care about the metaphor, but I am interested in whether it relates to your experience. What I want to know is like, how do you see these two different experiences of like founding and investing?

3:57And like, what does each teach the other? Yeah. First of all, I think it's very helpful to be an investor who has walked the shoes of being a founder, being an entrepreneur, being an exited founder. And I find that a lot of founders really appreciate that experience, that I can kind of talk about the challenges in fundraising. I could talk about the challenges of having a team and hiring and firing and all of that. So there's definitely a lot to be said for kind of being an operator turned investor. For me, I sold the company in June of 2021. I could see that this was going to be a tipping point in AI.

4:34You know, I started my PhD back in 2000. So I've been in this space for many, many years, as I know you have been. I started my PhD in 2000 as well. So it's like spot on. Yeah. So I felt like, okay, I've done all this work for this moment in time. And I thought a lot about whether I wanted to go back into building another startup. But I just feel like this is an opportunity to kind of have impact at scale by parallelizing kind of what I do and what I care about and using capital to invest where I think there's potential value and where it aligns with my thesis around AI. Do you think you could go back and start a company or you think that, what do you think?

5:18Do you have the itch every once in a while? So I think I was in love with Affectiva. I have two kids, 22 and 17 now. And I started Affectiva when my daughter was six and my son was a newborn. Like we incorporated the company when my son was born, like within a week of each other. And so I always joke that Affectiva was my third baby. Yeah, sometimes they did compete for my resources. I'm in like one, my kids probably have PTSD or something. Anyway, anyway. And I feel like I have to fall in love with an idea so much again to start a company. And I haven't found that idea yet. So never say never.

6:00But for now, I love investing. I love supporting founders on their journey. There's something magical about this early stage. Yeah. It's energizing, right? To talk to founders and to see the passion that each of them has for their specific project and to support that is kind of a very rewarding experience. Yeah, and be able to kind of shape that journey, whether it's by introductions or by kind of sharing a lived experience. Yeah, so for now, I'm loving being an investor. So Tulip is focused on AI. Blue Tulip. Blue Tulip. Blue Tulip. So it's focused on AI, but it's also focused on trying to specifically invest in more humanizing AI.

6:46Is that appropriate to say? Yeah. Our investment thesis is what we call human-centric AI. So that's AI that unlocks human potential, not necessarily replaces human abilities and augments humans, basically. We can debate that because there are instances where, you know, jobs are going to be automated because of some. We're going to talk about that for sure. And then we also have this thesis that there are big problems in the world and AI presents an opportunity to solve these big problems. And that's kind of what. So we think about it like AI that's good for people, good for the planet and is ethical and responsible.

7:27Yeah, I think that's a reasonable North Star. One thing that I heard you say recently, which was, I think, spot on and something that we've been thinking about and is, I think, a big concern. It's not the only dimension of opportunity that is a concern, but it is a big one, which is that you warned that AI risk becoming a boys club and widening the wealth gap for women. Can you explain why you think that's a risk and where exactly the widening is likely to be seen first? Is it founding? Is it funding? Is it product design, hiring, ownership? Is it just interacting with AI? What do you think? All of the above.

8:13And I recognize that this is not a very popular topic to bring up these days. So I get a daily digest of AI funding news. And one of these is TechCrunch. So TechCrunch does a very interesting thing for how it announces these new funding rounds. There's usually kind of the headline raises like, I don't know, like$100 million at a$5 billion valuation. And then a picture of the founders. And I started noticing a pattern. I was like, it's usually two or three men that are in the headlines. And day after day, I was like, okay, this is interesting. And the reason this concerns me is, if you think about it, AI is creating massive economic opportunity.

8:59And it's not just economic opportunity for the team that is founding these companies. It's actually who's investing. Because ideally, you know, when these companies are successful, the investors are successful too. And actually, the way I think about it too is, who's on my cap table as an investor? It's great to have wealthy, older men on my cap table. Thank you for supporting me. But I also want to ensure that women are on these cap tables too, so that we don't, you know, fast forward five years from now or a decade from now, and we've just exacerbated this economic gap between, you know, the gender kind of wealth gap.

9:36So that's something I care deeply about. And I'm kind of, I don't just invest in women. I actually, I feel very strongly that I have to invest in the winning companies, right? Sure. But I also kind of worry about what type of AIs are we building if we are not, if it's not inclusive in terms of who, you know, AI democratizes access, but we actually need to democratize the building piece of it too. How do you think that could manifest? Let's say that the majority of designers, programmers, leadership at AI companies are men, not women. What do you think that does to the product that comes out of the other side and how it interacts and relates to humanity?

10:23I think there are a lot of examples of that, but I think the one that is most visual maybe, there's a lot of investment going into humanoid robots. Yes. And there is a lot of potential opportunity, again, economic opportunity, but also kind of use cases in this space. I've spent a lot of time, like my entire career has been about how to marry emotional and social intelligence with cognitive intelligence. I think the teams that are building these humanoid robots are obsessed about the IQ and the functionality of the robot. And they're not really thinking about how are these robots going to coexist with us?

10:57So, for example, you know, I won't name the company, but it's like one of their leading humanoid robots. And it is able to fold your laundry and organize your living room. But if you look at it, like, I don't want that robot in my house. It is scary, right? And it's not the only way to build that. I interviewed this young woman, Grace Brown. Her robot is called Abby, is the robot. The company is called Andromeda. And it has social capabilities. She has a kind of an emotional intelligence brain behind the robot. It's very warm. It's accessible. It's relatable. I think we need to balance both. And that's one example where I, you know, I wonder if the teams that are building these kind of leading humanoid robots are diverse, not just women, but diverse perspectives, right?

11:52Yeah. Do you have any thoughts on that? Well, I mean, you mentioned warmth as one of the factors. We did a global AI negotiations competition here at MIT where people submitted prompts for agents that would negotiate over nine different scenarios. So they had to be flexible and negotiating in different scenarios. And it was AI-AI negotiation. So no humans involved. You just set your bot and then they negotiate. And we didn't expect that human emotional dimensions would be as important as they were in succeeding in completely automated negotiations. Warmth was one of the biggest determinants of success in negotiations.

12:41And it was good for claiming value and creating value. And the reason it claimed more value was not because it was aggressively taking value, was because it reached deals more often. And when you only looked at the bots that reached deals, it actually claimed less value. But overall, it claimed more value because it was successful in negotiating and getting to a negotiation conclusion. And so I think that we're missing big swaths of social elements that need to be part of what we put into AI. Yeah, totally. I mean, if you think about it, if you think about human intelligence, right, your IQ matters, but your emotional intelligence matters even more.

13:25In business, I mean, the best managers and leaders have high EQ, the best partners, the best friends, right? And so it makes a lot of sense to me that this would be the case for AI as well, especially AI that is going to collaborate and work alongside us. I mean, if you think about AI co-workers, right, and organizations where I think a lot of our organizations today are already hybrid AI and, you know, AI agents working alongside humans, you need these emotional intelligence skills to build trust. Yeah. Is this what you mean by relationship intelligent AI? Is that sort of the thing? It's a broad bucket.

14:08I think there's a concern that AI is kind of replacing human connections and human relationships. There's obviously some examples of that. But my thesis is you can use AI to augment and amplify human relationships by kind of injecting AI to help kind of help give you kind of, you know, I track my steps. I track my sleep. But there's no current way to really track your relationships and the quality and the health of these relationships, but also have something proactive that can help you organize and cultivate your network and your relationship. The best example I like to give, how many people have watched The Devil Wears Prada?

14:51By the way, movie number two is coming out soon. There's a scene where Meryl Streep is at this gala. I know the scene, yeah. You know what I'm talking about? Yeah. And like this guy and his wife are walking towards her and she's like, oh, my God, I blanked on the guy's name. And then Anne Hathaway is behind her and she kind of, you know, leans in and she's like, he's the ambassador of blah, blah, blah. And I'm like, that's the chief of stuff. That's the AI I want. You need that in the ear, right? Exactly. It can just like kind of just source. You know, it's got computer vision. It's got perception.

15:25It has all your LinkedIn connections. It understands the context of the conversation and can help you be a smarter, more connected, more empathetic human being. Story for another day, but that is the second startup that we founded called Human, H-U-M-I-N. We built this to try to do this for relationships pre-AI, and we sold the business to Tinder in 2016. But they were interested in the relationship aspect. And we were kind of at a point where we were either going to sort of squander a little bit or exit successfully. And so we took a strategic decision. It wasn't exactly sort of what we had envisioned when we started the company.

16:16But, you know, as you know, as a founder and an entrepreneur, there's all sorts of things that can break your stride in different ways. And so that was sort of the goal, but also maybe not the exact end point that we got. Well, I think timing is also really key. And I do believe now with generative AI, you can take all this. Relationships are messy. Like think about where your data, your relationship data sits. For me, it's my emails, my calendars, my WhatsApp, my DMs. It's a mess. LinkedIn, right? Instagram. Live conversations, right? My AI note taker, my own notes. And it's all unstructured data and it's disparate data sources.

16:57So now AI can actually take all of that in and allow you to interrogate it just conversationally. So I'm really excited. We're investors in two companies that are building different pieces in different pieces of this market. One is called GoodWord, and they're doing it for consumers. And the other is Via AI, which is a Boston-based company founded by David Chang, who's a serial entrepreneur in the Boston ecosystem. And he's very focused on the sales application of it. Because if you wanted a warm introduction to somebody at IDE, right? And it can say, oh, well, Rana knows Sinan. And you can ask for a word.

17:34So this is very similar to a very old company called Visible Path. They did this, I don't know, it was like 15 years ago, back when email was the only thing. One thing that we found hard was people to auth all of those, LinkedIn and everything else. So we would get people and then we would really have to work hard to get them to authorize connection to, okay, now connect your LinkedIn, now connect your email. And people were like, I don't know about all that. Yeah, trust is a big thing, right? It's important. Yeah. Share all of your relationship data.

18:16We're going to take a break. More of this conversation in a minute.

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20:48So you mentioned your kids, and we were talking earlier about the fact that you're experiencing this amazing bifurcation. Both your kids are super smart, super successful. I'd love for you to talk about them for a minute. But one of them has wholeheartedly embraced AI and the other one is like completely will not touch AI. Is that true? Yes. They're sort of the opposite ends of the spectrum, which I think is a microcosm of kind of the AI debate that we have in our world today. So, yes, my daughter, Jana, is 22. She just graduated from across the river. Yeah. She's a food anthropologist, which I did not know was a thing, but it is.

21:30I think AI is not going to automate her job. And she is all about human connection. She's building a third space in Cambridge where they host kind of real conversations. It's a cultural salon meets cafe. And she will just not use AI. And her argument is like, well, I have a smart brain. I've lived experiences. AI doesn't. And she just not even chat GPT to draft an email. Does she fear eroding her knowledge or does she just think it's not worth the time? She thinks she just doesn't trust it. And she doesn't trust that it will come up with something that's better than what she will do. So I find that fascinating.

22:14My son. She's probably right, by the way. You think? I think so, yeah. Part of me is like, because I believe strongly that AI is not going to go anywhere, obviously. And to be the head of the curve, she needs to embrace the technology and kind of play with it and experiment with it. But I love that she's doubling down on humans. That's what she's betting on. And I love that. My son, on the other hand, yeah, he's 17. He's a junior in high school. And he's literally my AI teacher. I mean, I spend most of my waking hours immersed in the AI ecosystem. And he still is my teacher. He uses Manus AI to do everything, like everything for him.

22:56He uploads his textbooks at school to Notebook LM and it spits back a podcast and that's how he studies. He's been using it to like scan these like Egyptology archives from the 1920s that are in Arabic and he translates them. And he's, it's just like fascinating. He's always trying new things. So he's all in. And it's just so interesting to see both. It's disruptive in your life to adopt AI because you have been doing these things in a certain way. And there's a retooling. Like we tell organizations this, that there's going to need to be a retooling, that you're going to have disruption. You're going to have to redesign processes.

23:40You're going to have to retrain people, reskilling, so on and so forth. It happens at the individual level as well because we had a way of doing something. And now when we're going to say, okay, I'm going to try AI to sort of like augment this or do this differently, we have to kind of adapt ourselves. In terms of organizations, you've also talked about this idea of onboarding AI into the org chart. So can you tell us what that means to you? Which business functions are sort of most ready to do that? And where do you think managers are underestimating the disruption? that that presents. Yeah. One of our investment theses is that, you know, AI is kind of shifting how value is being created.

24:27And one way it's doing that is through this idea of an AI coworker. And the coworker could be a software agentic AI, or it could be a physical AI, could be an actual robot, right? And so if you think about it, and we actually have companies that are, for example, I'm an investor in a company called Synthpop, another Boston-based company, and they are building an AI healthcare administrator. And the way they started is this AI automated a very simple task. It started with one task, patient intake. And then over time, because they're embedded in the workflow, they expanded more and more workflows.

25:02And their goal is to essentially eventually kind of automate the series of tasks that a healthcare administrator does, which means that you maybe perhaps as a health organization won't need as many healthcare administrators as you kind of currently have. I believe you will still need human oversight, but it'll look different. So the task of a human healthcare administrator maybe will become supervising these team of AI agents. But the point is a lot of organizations are now becoming a hybrid of humans and AI working alongside each other. and I keep imagining like, what does this future org chart look like?

25:45Because sometimes you might have a human manager overseeing teams of humans and AI or maybe an AI manager overseeing a team of humans and AI. So I think that's exciting. I also think we are totally underestimated, back to like the human element of it, we're totally underestimating what this looks like in practice. How do you build trust? How do you build accountability? How do you build clarity? Actually, even the question of who do you delegate jobs to? How do you think about what's the framework basically to delegate jobs to AI versus humans? Who gets what? Who gets to do what? And I think we're grappling with that.

26:24And then ultimately, how do you create culture? Like for Affectiva, for example, I'm sure it was the same for your startups. Company culture is so key. Yes, 100%. How do you do that when you've got a bunch of AIs and a bunch of humans? Yeah. And is it that AIs are part of the culture? Is it that AIs are in some way influencing the culture? I never thought about this concept of having an AI manager. That is one that's throwing me for a loop. I'm still sort of like trying to imagine like in my own mind thinking to myself, okay, I'm going to really have to have a conversation with my boss who is an AI about my pay or something.

27:04I wonder if our cultural norms were... So I've been on a few meetings where people... It's not like one-on-one meetings, but maybe where it's a webinar or a larger conversation. And people have been sending their note takers. They're not coming to the meetings anymore. But is it like a physical manifestation or is it... No, no, they just send... Okay. So they're just there to get the TLDR. That's it. Oh, yeah. And I wonder if it'll become normal. That's a little insulting, right? Because you're like spending your actual time. I'm there. But I do. But it made me think like if we will get to a point where this will become culturally acceptable.