Deena Shakir is a venture capitalist

Deena Shakir. That was my way of saying hi. Oh.

I should— I just say Leila Shakir.

Yeah. Okay, so listen, let's just let the cat out of the bag before I do a regular intro. Deena is one of my best friends, guys. So yes, I will go into why she's extraordinary and why this will be a blast, but I'm super excited to have one of my best friends on the pod.

Yeah, I am so happy to be here too. And yeah, we go way, way back. I love Leila, and I'm so honored to be a guest officially.

Yes. And so Deena, how would you describe yourself?

I would describe myself right now as very tired. Same. But, um, by way of introduction, I am a lot of things like you, an intersectional person. I am a Muslim American, uh, Iraqi American. I'm a mom, a daughter, sister. I'm a VC, which is short for venture capitalist. So I invest in private companies and help them grow and scale. But I've been a lot of things in prior lives, including when you and I first met. You've seen me go through some career pivots in the last 10+ years that we've known each other. So I've been a journalist, I've been in public service at the State Department, I worked at Google, and, and then most recently venture.

So, well, that's why I love your career so much, and I'm so excited to get into it because, so, you know, I'm a startup founder and In the startup founder world, the backgrounds are often pretty unique. It kind of takes— often it's not necessarily background by way of education or experience, but there are personality traits that get somebody to take this job on. And venture is similar where there's not one path to venture. Sure, maybe iBanking might get you there faster, or selling your own company might get you there faster. But I love your career because you really show how you can really be flexible and get where you need to get and pick up the right experience along the way if you're interested in venture.

Yeah, it's interesting because like I definitely did not anticipate this is where I would be when I was, you know, graduating college years ago. And I don't think I even really understood what venture was. And frankly, the industry has evolved and changed a lot too. For me, it was always kind of orienting around this North Star of impact and thinking about kind of how I can do something in this world and sort of what would be the next step to get there, not necessarily a 10-year plan. It's funny, I actually just shared or retweeted something I read earlier today that was really funny that was, that you especially, I think, given the fact that our dads, for those listeners who don't know, went to medical school together in Baghdad, AKA Baghdad. This tweet was basically making fun of, you know, as somebody on a plane who was a VC who, where there was an emergency situation and somebody needed to, you know, to have a doctor and essentially making light of the fact that as a VC, like, what are you going to do, give an uncapped note? You know, um, I bet on that guy, he could probably figure it out. Yeah. So, you know, I grew up in a family of doctors, and I think that's such an honorable, you know, way to have a direct impact, uh, in someone's life. But, uh, it wasn't for me as soon as I realized I needed to take organic chemistry. And so I went through these various different, different, you know, you know, chapters and each one sort of led me to the next. And, and that's kind of how I ended up where I am now. And it turns out that what I've always done my whole life is be a connector. Like that's what I love to do. That's what brings me joy. And that's really a big part of what being a VC is. So yeah.

And let's get into it. So where did you grow up, Deena Shakir?

I grew up in the Bay Area. So I'm a rare Bay Area native. Yeah.

And, and then what, like tell me about your journey in Bay Area college, so on and so forth.

Yeah. So, you know, my journey starts, you know, even before I was born with my parents coming from Iraq. You know, my dad left in the '70s for his residency initially in New York and then fell in love with the Bay Area and ended up finishing at Stanford. And so that's kind of how my family settled into the Bay. And so, you know, I had a very lucky and privileged upbringing growing up in this beautiful place and having the resources of my hardworking parents. And I grew up with 3 brothers and a you know all of them. And when I was thinking about kind of what I wanted to do, as I mentioned, you know, one thing that I really felt like had a tremendous impact on my life, which I'm sure it did for, for many of our generation, was, you know, September 11th and, and being, uh, in high school when that happened. Prior to that, like, you know, my name is sort of not necessarily descript you know, couldn't, couldn't quite see by looking at me if I was Muslim or Arab or Iraqi. But after that, like, I felt like these parts of my identity that had heretofore been so fluid were ostensibly at odds with one another. And, you know, I knew that was not the case because that's the hybrid of who I am. But we all remember where we were when we, when we heard about that. And so it got me really interested in kind of understanding the history of and the contemporary Middle East in the context of, you know, international affairs. And that's what I went to study in college. And I went to Harvard. I studied social studies and Near Eastern languages and civilizations, which is quite a mouthful, and really thought I was going to go down this path of academia and kind of working on this narrative of the Middle East. So I went to grad school and, you know, straight out of undergrad, I graduated in the summer of 2008, just a few months before that fateful collapse of Lehman Brothers and the subsequent financial crisis. It was really an interesting time. When I was graduating, almost half my class at Harvard was going into Wall Street or consulting. It was kind of like the thing to do if you wanted to make money and have an ambitious career. And I definitely did not see myself going down that path. Again, I was always orienting around impact and I had this sort of false dichotomy in my mind that it was either do well or do good, which I've come to realize over the years isn't necessarily necessarily the right way of thinking about it. But that's, that's what led me to grad school and went to Georgetown. You and I had some fun visits in those, in those years when you came and stayed with me. And, um, you know, while I was in grad school, I was working, as I did in undergrad, because I paid for, for both college and grad school on my own and was lucky enough to have jobs that were also really professionally enriching and amazing learning experiences. And so one of those, uh, as you may recall, was as a journalist. And that was sort of like vocational anthropology. And so I had this idea that like, maybe that's my calling. Maybe, maybe it's not, you know, the tenured academic path, but actually like becoming the next Christiane Amanpour. And little known fact, I was actually on air very briefly as the anchor of a bilingual news show on Al Arabiya. One episode is as far as it got. I'd like to think it was because of the financial crisis and the show not getting funding, but it might've been that my Arabic just was not good enough for on air. So please don't ask me to do an interview in Farsi. That was really hard. But anyway, that was what eventually led me into public service was after that experience, I interned with the BBC and happened to be helping cover the Washington desk and the White House. And so was covering President Obama's speech in Cairo in 2009, which many of us remember or know as the Cairo speech or otherwise known as the New Beginning speech. And that was really a watershed moment in US-Middle East or US-Muslim world relations where he called for a different way of doing development and diplomacy that was grounded in education and technology and entrepreneurship, a better way of building bridges. And I really wanted to actually be a part of that story, not just writing it. So that's how I ended up working for Obama.

Yeah. And how long were you with the Obama, um, How long were you with Obama?

So, uh, not like we were BFF. I wasn't with Obama per se, but I got a presidential management fellowship and, um, I initially worked actually at USAID and then at the State Department. So it was about 3 years total and, you know, great learning experience. But a lot of things happened during that period of time, which eventually led me back to where I grew up in Silicon Valley, which is not at all the place that I thought I would be. Like when I was in elementary school, high school, especially, there really wasn't a lot to do here if you weren't an engineer, hardware or software, like, you know, chip engineer. If you had these global aspirations and ambitions, it was kind of hard to be in California, especially here. You know, certainly there were jobs like, you know, excellent jobs in healthcare and law, but not beyond that at the time. But when I was in the State Department and I was witnessing, you know, as we all did, what was happening in the early days of the Arab Spring, and I was coming out here to the Bay a lot for work because I was again, working on partnerships, public-private partnerships. I was witnessing this sort of center of gravity shifting out west, like both kind of literally and figuratively. And I was seeing technology no longer as this like separate esoteric sector, but actually a way of doing a lot of different things better and sometimes with more impact and sometimes with more equity. And, and there was just an energy, like I just wanted to be here. And if that was a tall order for somebody with a degree in social studies and Near Eastern languages and civilizations, like there really wasn't The whole DC diaspora hadn't really come out here yet. And I wanted to work in product. I didn't want to do policy or PR, which was a more sort of natural progression from where I was. I really wanted to work on product. It was tough. I got a lot of rejections, a lot of people being like, who do you think you are trying to do this? This is not for you. I still have an email from a recruiter who responded to one of my many applications basically saying like, don't bother, you don't, you don't have the archetype. You didn't go to business school, you didn't do consulting. Yeah. So, you know, it was, it was, it was a journey. And then I got really lucky. I had an opportunity to join a team at what was formerly known as google.org, which is not the same google.org of today. But back then it was a place that was pretty unique in that it was really focused on product for social impact, which is very much what I wanted to do. And in particular, I got to work on building out their civic innovation effort, which was a great again, natural kind of next step from where I was in, in the public sector. So I did that in 2012, joined and specifically worked on product partnerships. And it was quite the learning curve. Like I thought I knew, you know, what I didn't know, but I didn't know anything, let alone what I didn't know. So, you know, really quite, quite the challenge in that regard, but also just an awesome experience. So 5 years at Google started off, you know, in that role and then had the chance to join a team where I got to be among the first business people to come in whenever there was a crazy ambitious idea that, you know, one of the engineers or PMs had and, and helped try to take that to market. And those ideas turned into things like Loon and Fiber and Verily and what we now call Google X. So it's pretty, pretty awesome. This is, you know, when Google was in a much different place and smaller than it was now, pre-Alphabet. And that's what led me to venture, actually. I sort of stumbled into healthcare of all things, uh, you know, I mentioned mentioned earlier on, of course, that we, we come from a family of doctors, as, as you do. And I was not at all qualified to be the person to be like leading this effort, but kind of raised my hand as someone who knew how to work with highly regulated industries and had an interest. And, you know, and I just dove right in and learned everything I could and helped build out Google's first HIPAA-compliant product, which was way ahead of its time as a telemedicine play. And it was, uh, it was interesting. I, I brought together all these disparate parts of the company that were working on healthcare and helped lay the foundation for what eventually became, you know, Google Health, in bringing together these different entities, but also met these amazing entrepreneurs, people like you, um, who were, you know, starting their own businesses at the earliest stages in healthcare and, and were doing more and more effectively with far, far fewer resources than my team at Google. And, and that's where I realized the real innovation was going to happen. So I wanted to be a part of that and ended up introducing some of those folks. That's kind of my thing, making intros to people I knew who happened to be in venture, and realized that actually that is what I am meant to do.

You know what I love about that journey? First of all, I just realized something that I've never put two and two together that you and I have in common, though we have a lot in common, which has kind of been the backbone of our friendship. We are more or less the same person but in kind of parallel universes. But I also— so Around the time that you were like, hey, I wanna get into technology, I wanna get into product. That's exactly when I made the shift from architecture to technology for the same exact reason. I was like, I wanna be a post-conflict architect. Wait, I'm not impactful in Baghdad. In fact, I'm a waste of money, space, and time. People there can do it better. But you know, like technology is wild and so much can happen. And this is when we started seeing, um, as a result, frankly, I would say due to social media, we saw a lot of technology get a lot of focus. And in, in ways when people started realizing the power of data and and the power of users, and it started getting integrated in so many parts of our lives in a more user-friendly way, right? Whereas before that, I would say that like maybe, you know, people had like really distinct softwares in healthcare or government that weren't very user-friendly. Suddenly things started to permeate with like the accessibility of cell phones. And I think that was a realization that I had, and I'm realizing you had the realization in parallel too, where I was like, wait, hold on, this is gonna be everywhere. This is really freaking cool. The opportunities are endless. What can I do with this space?

Exactly, exactly. And that was almost the same calculus that kind of went into my, my early interest in healthcare. And now I'm at the intersection of those things with, you know, doing a lot of healthcare investing, you know, as a VC. So it's fun to always be on the learning journey and not try to be too calculated about like what the future holds.

Yeah. And, you know, Deena, like another thing that I want to point out about your story is you talked about how you got rejected because you're like human, right? Everybody gets rejected. Something I've always admired about you is you also ask for what you want. In places where you're like, okay, this is going to be a long shot, but I know that I can do this. I'm very capable and I'm very like self-assured. So let me go and tell these people at this other organization I want this, but also let me show them my value. Let me start making connections. And I think that also differentiates you but has also led to so much flexibility in your career.

Yeah, thank you. I appreciate that. And to be honest, that's something I also look for in a lot of the people that I back. You know, these sort of having that chip on your shoulder to some extent, something to prove, and actually proving it. And so it's not like this sense of entitlement. In fact, quite the opposite. It's more like showing that value, proving it, doing the work, putting your head down, but also raising your hand.

Yeah. I mean, especially as women, as minorities, definitely a skill that's required. But, OK, so you go through this incredible career. You start as an anchor for one episode. And then you work with Obama. And then you end up at Google. You become super immersed in health care technology. And what was the jump from that to being like a full-on Deena Shakir, comma, venture capitalist?

That was another one that was really tough. I have to say, like, that might have been the hardest pivot yet out of all these pivots. It was really, to me, felt like this secret world that I couldn't even get a window into, let alone a door. And, you know, it was something that had been sort of on my long-term radar, like, oh, this sounds like it could be a cool job, but, you know, not necessarily something I thought was in my short-term plans until I started meeting a lot of these entrepreneurs and realizing, seeing them grow their companies, realizing what it took to grow those companies, seeing sort of what my own network was and my instincts around product and business and a lot of hustling, honestly. Like, again, lots of rejections, like lots and lots of people just telling me they weren't hiring, but then, you know, a few weeks later, whoa, you just hired this dude and then you hired this other dude. Or, you know, and doing all of that also, by the way, while I was starting a family, you know, like you, like during that period of time of trying to get into venture, I ended up having two kids. In fact, I was interviewing for my first job in venture at GV when I was, I think I might have been 6 or 7 months pregnant when I started. And, you know, it was pretty, pretty large by the final interviews, but was so nervous that it was hard enough as a woman in venture, let alone as a mother and a pregnant woman. So that was That was really a challenge for me. And that was before that summer in 2017 when a lot of things changed. And, you know, there was no AllRaise back then, you know, which is an organization dedicated to women in venture. There wasn't as much of an infrastructure or ecosystem around supporting diversity in this particular asset class. And it was hard.

And that's something about venture, right? So at least historically, diversity has been really hard to come by, not only amongst venture capitalists. I would— you can correct me if I'm wrong, but I would assume partners in venture, probably less than 10%, maybe less than 5% are women. Is that a good guess?

It's very, very small. Yeah.

Right, right. And like 2% of venture goes to male and female founded team. Um, less than 1% goes— no, it's 4% to male and female founded teams, 2% to female founded teams, less than 1% to any Black CEO, which, you know, it doesn't matter which gender. So like the, the numbers are rough, right? Like there's a lot of work to do. And how are you overcoming that now, especially as you look at a pipeline of deals and kind of consider founders. And I've said this on a few podcasts before, but the narrative in venture is like, we invest in early stages and you're an early stage investor because we trust founders. And that's a very flawed narrative when only 1% of venture goes to Black people, right? What are you saying about trusting Black people or the pipeline that comes in of, you know, Black-founded deals? So, I'm curious to hear how you're navigating this, especially because you're working in this space at a time of such immense change.

Totally. And the numbers are damning and they're terrible and there's a lot of work to do. And it frankly got, despite the proliferation of companies and deals over the course of the pandemic in the last 18 months, actually the ratio has gone down. So it's not good. There's a lot of work to be done, but there's also some data that gives me conviction even beyond knowing what's good for the world, right? It's not about like something that's charitable, but there is data that shows that women-led and diverse founding teams are better for the bottom line, full stop. They are better in terms of ROI for investors. They are better in terms of almost every metric that you would want to look for. And that is a superpower. That is a value, you know, like that is something that I look for in the teams that I back. Again, not just because it's I'm a woman or because, you know, diversity is the cool or trendy thing to do, but because they literally make the best founders and CEOs. And so, you know, that, that's one of the reasons why I'm committed to, to that and also to being vocal about that, because that's kind of where we start. It needs to be grounded initially in that data. And as you know as well, you know, there's also— I have a strong thesis around investing in mothers. And in fact, 3 of my portfolio company founders have had babies in the last last like year to year and a half, and, and they've only proven my, my conviction to be true. Like, you know this, you are an embodiment of this. You want some— you want something done, you give it to a busy mom. Like, you know, I, I don't believe that we as moms are superheroes. I don't want to like, you know, glamorize that narrative, but being a mother does give you startup superpowers or superpowers in general. And so that's, that's, that's the difference. There's— again, it's not a superhero, but the superpower of just like being able to prioritize your time because there's this inherent trade-off, right? I think Ruth Bader Ginsburg in particular, you know, had an amazing quote where she talked about having children in law school and throughout her career and how it made her a better mother. Being, you know, having her career made her a better mother, and being a mother made her better in her career. And I think that is true, although it is very hard, especially right now.

Yeah, I mean, every minute is intentional, to your point. Everything is a trade-off, right? Every minute at work is a minute that you're not with the kids, and so on and so forth. So I don't waste time. I know you don't waste time. That's another thing we have in common. We just don't have time to waste.

Yeah.

And so I feel, I feel very similarly. And, um, I'm actually like, so you know this, my, our CEO is Black, I'm a woman, our founding team is diverse. We've been together, nobody has left. So statistically we are against the odds. One of us should be gone. We shouldn't even be functional at this point according to the odds, right? Like the company should be gone. But alhamdulillah, things are going well and we're continuing to build this thing and So like your thesis for me is, uh, or I guess the research that points to a diverse founding team, um, resonates and it's something that I've personally experienced.

Yeah.

But also being a mom and I have to say like the moment I found out I was pregnant, I was at a WeWork in New York City and I got a phone call from Mount Auburn Hospital. I begged them, I said, I have a huge customer meeting tomorrow. Please don't call me before 5:00 PM if I'm pregnant, please. Lady calls me at 1:45, 15 minutes before I leave and she goes, yeah, honey, you're pregnant. You're definitely pregnant. I will never forget that Boston accent. And I literally stared at this boardroom of men, Deena, and I started sobbing. Like there was a clear WeWorky kind of cool back then boardroom and it was all men. And I was like, you've gotta be kidding me. Like, this isn't how it's gonna be, is it? And I've proven like, no, right? Because I'm a woman in leadership. I made sure that's not how it was. And my team is aligned with me and believes in the same things I do. But I do, I would agree with you that there are taboos women, women are scared to often, you know, show that they're pregnant during interviews, or there are taboos against it, I would say, in the startup world, which tends to have, I'd say, probably like an average age of employee tends to be younger than other industries.

Absolutely. Yeah. When you compound, you know, these various different biases around, you know, minority women, uh, you know, mothers and, and all of that, it's challenging. And, and I gotta say, on the, on the VC side too, you know, I'm a part of a couple of informal groups that are, you know, VC moms. And it's, it's also a struggle that, that we face, especially, you know, my kids are now 4 and 6, masha'Allah. And, you know, they're a little bit older, but friends of mine that are having kids now and thinking about, well, what does this mean in the context of, you know, whether they're raising funds and fundraising with LPs or whether they're trying to win deals and, you know, concerned about how founders will perceive them or, you know, whether they feel like, how can I actually take maternity leave because this is a job that doesn't ever stop? You know, those are all challenges still, not to mention, you know, just raising kids in this environment. Yeah.

Yeah. No, it's, well, it's great to see. And I think that, you know, every leader in your position, every leader in my position makes a difference. And so to kind of go back to the career story, you then ended up joining a firm, an awesome firm, working with a guy I know and admire, Bilal, at Lux Capital, right?

Yes. So, um, I was at GV, the artist formerly known as Google Ventures, for a couple years and then joined Lux almost a little over 2 years ago. And so—

oh my gosh, no way!

Yeah, crazy, right? Whoa. I know. Wow.

All right, so you joined Lux about 2 years ago, and I, I want you to kind of talk about this because I've heard you talk about it in other public forums, and I think it's important. But I've heard you talk about imposter syndrome a little bit, and you not necessarily talking about Lux's thesis and your background in service, right? So I'd love to hear your comments on kind of how you dealt with that and, and what exactly I'm talking about.

Totally. I mean, I felt that, I guess what I later learned was called imposter syndrome throughout these various different pivot points in my career. And, you know, if it— whether it was being at State and trying to get into a product role, or, or, or, you know, going from that background into the venture. And then, you know, even when I think there are a couple of things that I would highlight around that. When joining, you know, and when deciding where I wanted to go, one of the things that was really important to me was being at a firm and in a partnership where the sort of intersectionality of my identity, not just my ethnic or, you know, heritage or my gender, but actually like the varied experiences I've also had in my career, were not only— were not seen as like irrelevant or just random points on, you know, on a chart, but actually very critical to the job that I do. Because I knew that was the case, but I found myself in a lot of these conversations with other firms, like, either ignoring those, you know, those, those points in my career, glossing over them, really just focusing on what I felt, you know, thought they would think is relevant. But one of the reasons I knew that Luxe was going to be a fit for me is because I didn't need to sell that. I didn't need to make that case. They saw that. I think their portfolio, our portfolio is reflective of that, whether it's the companies that we invest in, in civic tech and related to that experience, the healthcare work that I've done. And so, that's something where I really felt like I could lean into that. But I had imposter syndrome also around leaning into what has become a strong area of interest for me, which is health tech. And that's where most of my investing has been and where I finally am comfortable owning the fact that that's that's, you know, where a lot of my network and expertise is in. But, you know, our parents would probably— or our dads at least— would find it hilarious, right, that that is the case, given, like, you know, they, they are the practitioners, they are the ones who went to medical school and are saving lives. And it's absolutely true. And, you know, I'm not going to be writing prescriptions for anyone or, you know, making complex diagnoses. But when it comes to innovation in the sector, I've seen it I've been a part of building it at Google. I've been a part of, you know, companies and helping them grow at GV and now Luxe. And I just— it took a lot for me to actually lean into that and not feel like, who was I to be doing this? I didn't have an MD or PhD, but now I own it and I love it. It's fun.

And, you know, the thing about venture is, I mean, as a founder, you learn quickly that your average relationship with your VC is longer than the average marriage in the United States, right? It's like 7 to 10 years. I think the average marriage is 9. This isn't even a joke. It's reality. And so what that means as a venture capitalist is you don't really see the benefits or whether or not your pattern recognition and decision-making skills are good until a few years in really, right? You start getting data points like a little bit further in. So at some point you're like, okay, well, this is my portfolio. So clearly I'm really freaking smart and connected and know how to do this. But for those first few years, which I'm assuming you're over the hump now, or a few years, you don't have that. You have to be able to back your ability to think through things, find the right deals, and find the right people. And then you have to give those deals the time to flourish and support the founders through their journey and so on and so forth.

It's true. I mean, it's a very different kind of model and feedback loop than when you're on the operating side. And I wouldn't say I'm over that hump. Oftentimes it takes 5 to 7+ years before you can really know.

If you've got a few exits, right?

Yeah. I mean, exits and seeing companies through. Of course, it's different depending on what stage you're investing in. So I don't know if I'm any good at this yet. Like, you know, I know that, like, I have great relationships with my founders and, you know, and I'm enjoying it. And there's a lot of things that I can show in terms of deals that I've helped, you know, close on the commercial side, etc. But no, I don't, I don't have that track record yet, and I won't for a while. It's just something you have to kind of come to grips with in this industry, right?

But, you know, like, I think that you've proven yourself in other ways. And I saw a milestone for one of the companies you back becoming a unicorn, or are you backing it made it a unicorn or something along those lines, which is awesome, right? Like that is a sign of success. It is not easy to raise a lot of money.

Yeah, I'm very proud of that company. We just announced, for those that are listening, we just announced our co-lead in a company called Maven Clinic, which is the category leader in women's and family health. So, it's very much a thesis that is near and dear to my heart. And this is my third investment in the women's health space. Health space. So also one where I've been spending a lot of time. Um, so just could not be more, more proud of Kate, the founder, and, and the fact that she also, you know, is a, a mother of 3, including a, you know, a small infant that she gave birth to via emergency C-section over the course of, you know, the last few months as I was getting to know her. So it's pretty remarkable.

Yeah. And, you know, I'm really happy to hear that there is anything in the women's health space that is being valued that much in technology, because as a woman and as somebody who's had a baby like it sucks. It really sucks. Pumping sucks. Being pregnant sucks. The glucose test sucks. Like, there just isn't yet— like, you know, if you look at studies about any sort of medication that helps men for things that are, you know, even things that are developed much quicker for the other gender, but somehow for us, um, it takes a lot longer.

It's true. It's true. I mean, there was that, the recent acquisition of, uh, of Modern Fertility by, um, by Ro that a lot of people were pointing to. And I, and I am a big fan of both of those founding teams. And, you know, I think it was a great outcome for a lot early investors there. But, you know, Ro started off as a men's health company, and now they're doing a lot more than that. And the founder, Zach, has been very vocal about how he believes the women's health category is huge, and they're really doubling down there. But, you know, perhaps there's a future where it's the women's health company that's acquiring the men's health company. And, and I think, you know, Maven is going to be at the forefront of that.

Well, I look forward to it, and I look forward to a time when I don't have to talk about how much it sucks to be pregnant because the system is not working in your favor. And you, you had anecdotes too, like me, where I am like my own advocate as I'm pregnant, and I go to a go to a very good hospital, as you did, but there are so many different bodies of research around gestational diabetes, something you and I both have had to deal with. And like, we've had to educate ourselves because there isn't even necessarily a synonymous kind of body of research that every hospital would agree with. And that's just one part of being pregnant, which is one small part of some women's lives, right?

Absolutely. And, and it is much, you know, the problem is even more pronounced in, uh, especially in the Black maternal health crisis. It is just unbelievable how little progress has been made toward bridging the inequities in healthcare. In fact, there was just a New York Times article the other day, maybe yesterday actually, or the day before, that was referring to this set of studies in JAMA around the last 20 years in healthcare and how little has been done. And I think maternal health is one of those areas where Vice President Kamala Harris called our called the current situation a Black maternal health crisis. And it really is. And not just in terms of maternal outcomes, pediatric outcomes that contribute to fertility and endometriosis and more.

There's life expectancy. There's a very big life expectancy gap in like 2021, right? And then on the flip side, it's funny, this is totally unrelated, but I was reading an article— I mean, it's related, but not in the context of this discussion necessarily. But I was reading an article yesterday about how effectively like any sort of removing children from homes, um, or any sort of cases with ACS have kind of been flipped on their heads throughout the pandemic and kind of how it's been shifted based on Black people not getting reported as much because they don't go to the pediatrician and they don't go to school where they're reported all the time. But also it talks about how I think 40-something percent of Black kids get a visit from ACS at some point in their lives, like one in every two.

It's unbelievable.

But the abuse, like if you look at various communities, the abuse is not increased in Black communities. It's the same in white communities, right? Like, that just really, especially as a mom, that devastated the heck out of me. But, um, yes, I look forward to you financing many things that can advance any sort of equities amongst many communities and our Black community.

Thank you. I, I'm, you know, I'm looking for those companies out there. And so any entrepreneurs who are building in that space toward value-based care, toward health equity and health justice, there's a huge opportunity there. I'm so excited by all the innovation around digital health, and I think the The next wave of it needs to be focused on the communities that need it most. And the pandemic has highlighted that in a lot of ways in terms of its outsized impact on women, especially on Black and Latinx women and in general on communities of color. Yeah.

And that actually takes me to my next question. Great segue. How does somebody raise money from you?

Well, it's a process of getting to know me and the team. I think I've I've publicly talked about this, but, you know, I have been the one doing cold outreach in the past, and I have a lot of respect for that kind of hustle. But I also know now, being on the, on the receiving end of that, that, you know, that there is a, a more effective way to do it. And, and I like to even approach those— the situation on the other end myself. I'm often doing a lot of outreach to founders. It's not, you know, a lot of people think venture is this, is this job where you kind of sit back and put up your feet and let people come to you. It's actually not. Venture capital is, is a lot of sales. Like, you, you are, you are advocating to get into those deals, the best deals, and it's very much a relationship building and a symbiotic process. So it's not just about kind of people getting in touch with me, it's also like me finding them. And so, you know, um, that's a process that, that happens over time. But I, I appreciate those who, who do that outreach, whether it's on, you know, Twitter or or otherwise. And I look forward to learning more about some of these awesome opportunities that are, that are starting up these days.

And what would the advice be that you would give to somebody? I mean, it's been a long time and I don't know how much the industry has changed since like we were, you know, initially putting together a prototype. But if somebody literally today is like, okay, I have this great idea, you can do it a number of ways, right? You can apply to an accelerator, put something together, test it in the market, then find an investor. What do you find is the most common for early stage specifically? Like, what does a very capable and competent pitch include?

Yeah, so I think the ability to articulate your pitch in a really pithy, you know, intelligible way is just such a— it's such an important skill. It's not just about your ability to fundraise, it's a skill that will, that will enable you down the road to recruit. It will enable you to sell, you know, whether you're selling to your, your end user as a consumer or an enterprise customer. So, you know, I've seen some amazing, amazing, uh, you know, investor memos that people are sharing these days, like via Notion. You know, I love Looms. I think Looms are awesome. Like, yeah, I know you do. Being respectful of, you know, someone's time on both ends. Like, you know, I, I shouldn't feel entitled for someone to take a meeting with me just because I send them like a one-line email. And so, you know, folks who, who do that and are able to do it in like a matter of 30 seconds or a minute and, and make sure that there is a fit before having a conversation and just knowing, as you and I do, and as all moms and many parents do, that the time is everything and you want to make sure you're using your time effectively as a founder and also as a VC. And so I don't, I don't want to waste someone's time if it's not something that I'm, you know, particularly, you know, interested in investing in. Um, and, and the founder should also like seek out the VCs who, you know, are specifically, you know, looking into their, their sector and their space.

That makes sense. I mean, at first, really, if you were to take a step back, like the stage that you're describing is kind of a discovery stage, right? Where it's like, are you even a fit? Can I even help you as a VC? What I'm saying is I will buy a piece of your company, but I will also in exchange help you grow that company. Right. So then after that discovery stage becomes a stage of really building the case. And that's when it, that's when the founder has to shine and say, yeah, let me tell you why. And my understanding is that actually with the pandemic, term sheets are everywhere. There's been no, there's been no shortage of funding. So how do you work with your peers? I mean, what is the percentage of deals that you would say comes in from friends versus you doing cold outreach versus your personal network?

Yeah. So, you know, having that peer community of investors is is important. But, you know, for me, because I didn't grow up in this industry, like, there— it's a very different dynamic than, you know, friends of mine that I might have gone to school with that either went straight into venture or have been doing it for like 10+ years. I have discovered some incredible friends through, you know, who are also investors, especially women, and in many cases moms as well. And so there's, there's a trust building that happens. Venture is not a monolith, so there are folks, you know, who are angels or doing syndicates at the much earlier stages, and there are growth investors. And so being able to like collaborate and kind of know who's who, and then also getting, you know, references and referrals from your founders. Like, you hear it, you know, it's a small world and people talk. And so if there's bad behavior that's happening from a VC to a founder, like, those reputations matter. And it's not always just about like, you know, writing checks and seeing all this up into the right growth. Like, there are times in the business that are not going to be great, and that's part of your role as an investor and board member, is to be able to help navigate through that and also, you know, have those tough conversations when you have to. And so having that relationship, you know, that foundation set, is just really, really important.

Yeah, I can understand why that would be the case. And it's funny because I've gotten many emails from investors who are like, do you know companies— I've gotten many cold emails from investors that are like, hey, let me take I'll take you to lunch. So it's funny, like, hearing about things on the flip side. And you're right, like, ultimately venture— there's a big sales role in venture. And then once a deal is closed, you're about kind of making sure that the value that you and the founder have decided upon is reality. Because I think what people don't realize is when you say something is unicorn, that means we project the value to be a billion dollars after this injection of money. But, uh, this is— these are the steps that need to go into place for this to become reality, right? And often, actually, it's not uncommon for later stage funding, for the ARR to be like, I don't know, for the value to be 4 to 10 times the ARR. Like, that's not uncommon, right?

I mean, I've seen 40 times.

Yeah, I mean, hashtag WeWork, back to— let's take it to the beginning of this podcast, right?

You know, it's, it's definitely an interesting time, um, and it's not always going to be like this, and it hasn't always been like this. So, you know, that's something to be aware of. But yeah, there's a lot of capital out there. There's also a lot of amazing you know, founding teams and entrepreneurs out there. And so, you know, it's also an exciting time, but, you know, I don't know how, how long we will be in this state. And so being able to prepare companies for all situations is something that we as investors really need to do.

Yeah. And Deena, when you're writing your, you know, autobiography in however many years, how do you want this to all end up? Gosh, I'm going to end on an easy note.

I know. Well, you know, just like when I was Starting off, like, I, you know, I remember somebody asking me a year or two out of school, like, what my 10-year plan was. And, you know, I was used to being around people who had that, but I didn't have that back then. I think it's a little bit different now because that sort of discovery journey over time in retrospect is kind of what led me to where I am now. And this is very much the type of career that, you know, I see myself in for a long time and that I love. And frankly, it's because, like, you know, I get to learn, like, it's my job to learn about new industries and work with— like, there's a lot about it that I love, even though it is also the hardest I've ever worked in my entire life. You know, so I hope that I can be a part of, you know, a small part in the journey of helping grow companies that are ultimately— sounds cheesy, but making the world, you know, a better place. And whether that's through improving health outcomes and population health, whether it's through diagnostics to, you know, detect diseases earlier, therapeutics to treat them and ultimately funding more underrepresented founders as well who are creating value for themselves and for their families and the next generation of wealth. And I hope that it will ultimately help to bridge a lot of these inequities.

You know, it's funny, you say you didn't have a 10-year plan, but you started this podcast talking about your commitment to impact and you kind of made a false dichotomy, which you realized later in life about being rich or being impactful effectively. And you're ending this podcast saying your 10-year plan is impact, right? So, like, actually you're like, 10, 20, and 50-year plan seems to be pretty aligned at the high level.

You know, it's interesting because you know my brother Omar, and he and I are only a year apart. And he— and believe it or not, we went to— well, you know this, but we went to grad school together actually. We did the same master's program. He ended up going, you know, down a very different path, and now he's a human rights lawyer and I'm a VC. And on paper, it literally like looks like our our careers couldn't be no different, but both of us really shared this, you know, desire toward impact. And I think there's no one way to do it. I'm not saying that, yeah, everyone should go be a VC because that's how you can make the world a better place. Like, absolutely not necessarily true. As I started off saying, like, whether you're a doctor working on the research side to, you know, find a cure for cancer, or, you know, working in rural communities, like, literally helping people with their everyday health challenges, like, that's incredibly impactful. If you're on the nonprofit side, that's impactful. You know, there's so much that you can do. And so it's, it's sort of a combination of, like, not just like, hey, how can I make the world better? But also like, what is my unique way to do it? And I'm not going to be the one on the airplane that's saving someone's life. I wish, you know, I will take some CPR classes and hopefully I can do that. But, you know, but that's not, that's not me. I'm not going to be the one reporting on human rights abuses on the ground. And I'm so proud of my brother and the amazing work that he's doing. And I'm not going to be the one who, you know, is necessarily doing some of the many other things that one can do towards impact. But this is This is what I love to do and what I'm good at, and I hope that it can have some impact in the future.

I look forward to it. I can't wait to keep up with it. I've loved our parallel lives so far. And for those who are not as lucky to live in a parallel universe, how can people find you?

Yeah, you can find me on Twitter. I'm @DeenaShakir and follow me and DM me there. My DMs are open and any friend of Layla's is a friend of mine.

Amazing. Thank you so much, Deena.

Thank you.