Inspired with Alexa von Tobel
00:00:33 · Alexa von Tobel, May Habib
[00:00:33] S1: Welcome to Inspired. I'm Alexa von Tobel. What if your company has thousands of employees who never slept, never forgot a policy, and could instantly access every piece of institutional knowledge you've ever created. That's not science fiction, that's agentic AI. I'm joined by May Habib, founder and CEO of Writer. May has built Writer into a $1,900,000,000 company, raised 369,000,000, and created one of the most trusted names in enterprise AI. Uber, American Eagle, Pinterest, Vanguard. These aren't just customers. They're betting their most critical workflows on Writer's AI agents. While others chase hype, Writer has become the gold standard for AI that's built to scale with absolute governance and trust. In this conversation, you'll learn all about her unique childhood in Lebanon, the journey of building Writer from the ground up, and May's prediction for how AI will transform work and society over the next decade. This is a front row seat to the future of AI. Let's dive in. If you're running a startup, we know things like managing equity and communicating with investors are always top of mind. Carta has built a connected suite of tools that over 40,000 companies use to do just that. Their platform of software and services helps you lay the groundwork so you can focus on building. To learn more or get started, visit carta.com. Welcome, May, a friend, somebody I really, really have enjoyed getting to know. May, first of all, congratulations on everything you've built. [00:01:57] S0: Wanna Thank start
00:01:57 · May Habib, Alexa von Tobel
[00:01:57] S0: Wanna Thank start [00:01:58] S1: at the beginning, the origin story. And one of the things I loved getting to know more about you was actually just the fact that you were born in Lebanon. You immigrated Canada when you were young, moving between many different languages, cultures, and value systems. I mean, really, somebody seeing a lot of the different ways the world can work from an early life. Can you talk a little bit about your childhood and what you think really stands out when you think about what shaped you the most? Let's start there. [00:02:27] S0: Yeah. I was the oldest of eight in a family that is very extended and very close. So it's funny raising two kids with my husband now who did not grow up this way. You know, chaos was kind of the norm. And I think being able to, you know, hold your own voice and your own thread really amongst, you know, a... Not just a lot of action, but a lot of conflicting advice and value systems, as you said. You know, I think I learned to, you know, stick to my guns and just have conviction and and follow the beat of my own drum, as they say, from an early age, right, because there were so many influences. There were so many people, all with a lot of ideas about how I should spend my life, and you know, what being a good girl was and meant. I really love that you were one of eight. I was one of three, and
00:02:27 · May Habib, Alexa von Tobel
[00:02:27] S0: Yeah. I was the oldest of eight in a family that is very extended and very close. So it's funny raising two kids with my husband now who did not grow up this way. You know, chaos was kind of the norm. And I think being able to, you know, hold your own voice and your own thread really amongst, you know, a... Not just a lot of action, but a lot of conflicting advice and value systems, as you said. You know, I think I learned to, you know, stick to my guns and just have conviction and and follow the beat of my own drum, as they say, from an early age, right, because there were so many influences. There were so many people, all with a lot of ideas about how I should spend my life, and you know, what being a good girl was and meant. I really love that you were one of eight. I was one of three, and [00:03:29] S1: I would often joke that chaos, I was raised in utter chaos, truly. It does prepare you in some ways, but one of eight, May. That's wild. Can you think of a story or something that happened in your childhood that if you had to think about, like, a straight line to you being comfortable with just taking so much risk as you have taken a lot of risk on as an entrepreneur, anything come to mind?
00:03:56 · May Habib
[00:03:56] S0: You know, not one thing, but really how I think about and remember the ways me and my brothers would literally spend every single day after school for years. Like, we would come home, drop off our stuff, and then leave. Like, literally from six years old. Right? And like, we were kind of the pack in that early years. Like, it was three of us born in three years. And we would literally go to the park and like run shit at the park. You know? And like organized games and Olympics. And there were like multi day events where like people were on teams and people had points and like people had to kinda do what we said. I mean, we weren't bullies at all. Like, this was fun. People were excited to, like, come and, like, hang out with us and play our games. And then, you know, we had to come home when the street lights came on. That was, like, our cue. That's what our mom wanted us to do. And, yeah, I just like spent years with really a lot of freedom and, you know, growing up in a Lebanese village. I mean, literally like from the time I could walk, would just leave the house and roam, you know? And it's it's funny now raising kids and like, you know, we both have young children. Like, you know, these kids are like air tagged to the hilt. I don't let them go to the bathroom, you know? And it's just so funny that like, we're entrepreneurs and take so much risk in our life, and, you know, I bet a lot of it has to do with just how much freedom we had.
00:05:25 · Alexa von Tobel
[00:05:25] S1: They are air tagged to the tilt. Their air tags are air tagged. You and I were were fortunate both to, you know, spend time at Harvard, and you actually worked on the Crimson. You've always been somebody so interested in in languages. You literally combined economics and near Eastern languages and civilizations as what you focused on, and then you spent time at the Crimson. Talk a little bit about your love of language. I mean, it it sort of feels obvious that you build Writer when you know so many facts about your childhood.
00:06:00 · May Habib
[00:06:00] S0: Yeah, it's, you know, it is fun to really feel like, in so many ways, I've been working on the same things my whole life. And it's hilarious to actually, like, I don't draw a straight line to it, but I spent so many nights at the Crimson, literally like four, five in the morning. And what did you do as an editor? You literally took a red pen and you had like the Crimson style guide on your desk and you like redlined, you know, like mistakes. And it is funny that, you know, now we do it in such a different way and, you know, just literally producing incredible, you know, journalism is still what the Crimson is doing. And in a lot of ways, like, the technology has changed, but what it means, you know, to ask the next great question and, like, question authority. Like, none of that has changed. And I do think, you know, questioning power is also something that comes very naturally to me. And a lot of, you know, what we do at Writer is challenging the enterprise to think differently, right, about so many facets. So, yeah, there are a lot of things that just feel like running themes in my life. And, you know, the the stint at the Crimson and and I've interned in other papers, etcetera, afterwards was was certainly part of it. And then the the threat of language. I've spoken about this before. You know, everyone in our household spoke Arabic. The Arabic is my native language. And when you grow up in the West in a family that speaks another language at home, you know, especially as the oldest child in an immigrant family, not just my family but the whole clan, I was the eldest. You know, you are a translator, not just of language but of culture. I read a paper recently that compared the brains of German native speakers and Arabic native speakers. There were And literally... Your brain is networked differently. The way that the left and right hemispheres connect is very different in a native Arabic speaker than a native German speaker. And you really do... You know, when you think about, you know, how how folks are translating not just language, but culture and value systems. You know, so much of, I think, what we are beginning to learn about the human brain has us much more similar to transformers than we thought, right? Which is very interesting. Language does shape who you become.