Meghan Joyce, Co-Founder and CEO of AI startup Duckbill, joins Niki in the latest installment of our Profiles in Tech Series. She shares insights from her unconventional career path from the Treasury Department to raising venture capital for an early-stage Boston tech company with stops along the way at Bain Capital, Uber, and Oscar Healthcare. Niki and Meghan share their optimism for the incredible opportunities AI offers both businesses and consumers.
“What's so exciting as an entrepreneur in this space is the playing field is still wide open. It's not clear what the winning business model is going to be, where the clearest product market fit is, and that creates enormous potential. And I wouldn't be surprised if we see some many cycles of boom and bust here and a transformation of how we all think about AI.” -Meghan Joyce
Meghan Joyce, Co-Founder and CEO of AI startup Duckbill, joins Niki in the latest installment of our Profiles in Tech Series. She shares insights from her unconventional career path from the Treasury Department to raising venture capital for an early-stage Boston tech company with stops along the way at Bain Capital, Uber, and Oscar Healthcare. Niki and Meghan share their optimism for the incredible opportunities AI offers both businesses and consumers.
“What's so exciting as an entrepreneur in this space is the playing field is still wide open. It's not clear what the winning business model is going to be, where the clearest product market fit is, and that creates enormous potential. And I wouldn't be surprised if we see some many cycles of boom and bust here and a transformation of how we all think about AI.” -Meghan Joyce
Niki: I'm Niki Christoff, and welcome to Teched Up. Today's guest is Meghan Joyce, Co-Founder and CEO of Boston-based AI startup Duckbill. We're talking today about her life as a tech founder, about MJ's evolution into AI, and we'll also chat about her career path from the Treasury Department to raising venture capital money for an early-stage startup.
I always love to hear about people's path, especially from DC to VC. Megan, welcome to Teched Up. Thank you for coming on the podcast today.
Meghan: Thank you so much for having me.
Niki: So you're calling in remotely from Boston.
And one of the things I love about what you're doing is that you have a startup based in Boston, which is kind of refreshing because we do so many Silicon Valley places.
Meghan: we have a bi-coastal team. So the truth is, we do have a team in California who has its origins in a lot of Silicon Valley companies. But what I found about building in Boston, and this was true for Uber as well, is you get incredible talent in, y’ know, what is common, what are commonly considered tier two markets.
And when you are a consumer tech company in Boston, you can get the best consumer talent out there. So we've seen it as a real advantage to be able to recruit from both talent pools and build in such a special place.
Niki: And I want to talk for a minute about Uber because we actually overlapped there. You were there longer than I was, but both of us were there during sort of a peak spicy time [chuckling] for the company.
And I want to talk about it.
[cross talk]
Niki: Yeah, it was real spicy. I want to talk about how that formed your career, but I wanna just back up really fast. So, you were the COO of Oscar Health. You were previously a policy advisor at the Treasury Department, and you're on the board of the Boston Beer Company and Garden Health, which I just think is like such a cool set of attributes to be on your resume. But I did want to start with Uber. I know it influenced how I think of everything because it was so scrappy. It was so high stakes. It had this unexpectedly - I think people have this idea of the culture being bad. I loved the culture. I thought it was such a good team atmosphere. So, anything about Uber that stands out?
Meghan: Yes, and I agree. I had an incredible time at Uber.
And, I think, what we learned during the spicy era was that too many people weren't having as incredible an experience as you and I did. And, I think, it was a highly decentralized and variable culture. But there was a lot that was really common about the culture that frankly led to it, the company now becoming $100 billion organization, and I don't think it would exist without some of those more challenging parts of the culture that, y’know, didn't scale, didn't often serve the company as it evolved and became more mature, but my goodness made it possible in those early days to do something incredibly hard.
And y’know, if you think about Uber, it's a much more difficult business than a SaaS company or pure technology, right? It's at the intersection of technology and the real world, which are the kinds of business models that I love to operate in. Oscar, Duckbill are the same way.
And what it takes to build at that intersection of technology in the real world is running through walls, creating something out of nothing, and doing something, frankly, that most people would shy away from or would think is too difficult to do and walk away from [Both: chuckling] far earlier than most of those early Uber people would.
And one of the mantras that we had at the time that is now one of my Duckbill company values is: we run through walls. And I think what we learned at Uber is that any wall can be run through, and what an unbelievably empowering thing to realize. I wish more people knew this. Now, it might be incredibly hard, it might be expensive, [Niki: chuckles]
Niki: It might cause some self-inflicted [Meghan: yeah] wounds.
Meghan:Yeah, and you might decide, like, “I run through this wall, I want to take a different route.” But when you realize that any problem can be solved, you become fearless. And it opens your mind to what is possible, and you would be amazed at what you can do when you realize: “We can solve this problem. I just have to get [chuckling] creative here.”
And I think that awareness has led me to do things like going into Oscar, which is innovating in health insurance, which is an incredibly challenging space in which to innovate or start Duckbill, which is a really challenging business model. And, y’know, we see a different way. We see a way to make it work.
And candidly, that's what it takes to get a startup off the ground. It's what takes to execute at the center section of tech in the real world. And it's something that I learned through and through at Uber, which, again, was a pretty incredible place to be for a long time.
Niki: I agree. You're right. So when, when you're in transportation, and you're using software to put humans into 4,000-pound vehicles with strangers, that is an incredibly hard, highly regulated, disruptive thing to do.
You were very eloquently just said, “Not everybody had the experience we did,” obviously, which was part of the one of the first dominoes for a difficult press cycle. It pushed my boundaries because I'd been at Google, which was at the time, y’ know, It was bigger. It was smaller than it is now but still quite corporate. So, it did give you the sense of like, “It's going to be fine. I mean, it's going to be tough, but it's going to be doable.”
DC is filled with former Uber folks who I'm still really close to [Meghan: yeah] because we all went through these really challenging places. So, okay, tell me a little bit about your time at Oscar Health and then how that has led to where you are now.
Meghan: Yeah. So it's fascinating. Duckbill, both its team and its business model have such a DNA and such origins in both Uber and Oscar. So, when I went from Uber to Oscar I knew I wanted to stay in a space that was using technology to disrupt an antiquated consumer business that was broken.
We did that at Uber in the transportation space. And Oscar was doing the same in the healthcare space. Oscar Health offers health insurance primarily within the Obamacare space, a big policy initiative that I had a personal connection to from a mission perspective, and the thesis was: we can use technology to change consumer behavior in a way that bends the healthcare cost curve and brings people along and living happier, more joyful lives.
Part of the Oscar thesis was we need to use technology to get access to great care in a way that was never possible before. And so there was an enormous amount of technology on the back end that allowed for really smart healthcare navigation or a very warm and engaging experience, which is not what you [chuckling] traditionally expect [Niki: right] from your health insurance company.
Now... It was not easy [laughs]! It was not. [Niki: right] y’know, it was the kind of thing that required an enormous amount of creativity and gumption and running through walls. And my thinking after a decade of serving as an executive and also trying to make my home life work was if we can put people in 4,000-pound vehicles and get them around town where they need to go safely. If we can take someone who is in one of the most vulnerable moments of their life and help them navigate an unbelievably complex healthcare environment in a way that is supportive and engaging, we can find a way to leverage consumer tech to help people in their personal lives and democratize access to help at home.
And that's why we went and started Duckbill.
Niki: Okay. So, let's talk Duckbill. So, my understanding is it's sort of AI-assisted or enabled? At one point, I had, had heard about you talking about busyness, sort of taking over your life. And there's TaskRabbit, which I use a lot. I don't know that people in DC do, but hiring taskers to come in and help me mount my TV, lift and shift furniture. [Meghan: Yep] Especially - I've lived alone as a woman for the last 10 years.
So I got a lot of TaskRabbits on speed dial. [Meghan: Yeah] Those are sort of software-assisted, y’know, physical world meets digital world. But then, what's this evolution into Duckbill? What's the purpose, the mission, and the vision for the company?
Meghan: Yeah. So the, the mission started when I was even back at Uber, right?
When I started at Uber, I was 28 years old. I was single. I was renting a cheap apartment. And over the course of my six years there, got married, had a kid and another kid, bought a house and eventually a car. And life got really complicated really fast. And I loved my work. That was where I drew an enormous amount of energy and whatever spare time I had, I wanted to be spending with people I loved: my kids, husband, my friends, myself [laughs]. Sleeping, what a novel idea! [Niki: yeah] My life quickly became consumed with all of the demands of adulting.
And I realized, you know, for so many families, including mine growing up, so much of that work for centuries has been done by, frankly, stay-at-home women, whether it was a stay-at-home, mother, wife, or a grandmother, intergenerational living in the home, or for people of immense privilege, folks they hired into the home to do this kind of work. And 99. 9 percent of us don't have that luxury.
Today, women are now making up 50 percent of the workforce and the majority of undergraduate and graduate degree programs. We all need help. We all deserve help and it's all too expensive and inaccessible to find in a really reliable way. And so, while at Uber, I started looking at this business model and chewing on it, but frankly, I didn't think the technology existed to deliver it at scale. I couldn't figure out what the wedge was.
There have been other companies who have tried to do this in the past. I mean, you mentioned TaskRabbit. We have so much love and respect for them. There was Jet Black back in the day, Magic, Fancy Hands, y’know, Hello Alfred. [Niki: oh yeah] Folks have tried to do this and yet, for so many years, the tech didn't exist to do it at scale- until now.
AI is the tech wedge that can start to actually crack that open and allow us to do this kind of personal assistant for everybody at scale.
Now, there's been an enormous amount of conversation about AI agents. Bill Gates has come out and said, “This is going to be the next frontier, this AI agent.” The problem is that AI agents to date have been pretty disappointing because they cannot service the last mile.
And what Uber and Oscar and these other large behemoths within the tech slash real-world space have realized is that it's all about the last mile. [Niki: Yep] And what it takes to deliver the last mile is technology plus humans. Amazon, Uber, Oscar; none of them could be who they are in the multi-billion dollar companies that they are without the combination of tech plus humans.
And the key is bringing them into a same in the same space such that you get the best of humans, what they are uniquely capable of, and the best of technology, what it is uniquely capable of.
As part of your Duckbill membership, you get unlimited access to a personal assistant that is, in reality, a combination of expert humans plus AI and you should feel like you're interacting with a real personal assistant. And the reality is it's armed on the back end and sometimes increasingly on the front end by a combination of artificial intelligence and a real human such that we can do this at scale.
We can research anything in the world, but when it comes to waiting on hold of customer support, right? We're calling a doctor's office and switching your annual mammograph appointment because you had a last-minute business trip come up. A human can get that done for you to ensure true reliability and real leverage.
Niki: We were talking just before we started recording. I just moved, and I will tell you my to-do list is staggering. It's un- it's breathtaking! [Meghan: I believe it] And a lot of it is utilities, D.C. water, the DMV, which fixed my address, but not my parking zone, [Meghan: Oh!] y’know, it's like one one phone call after another and I'm working more than full time [Meghan: yep] So, when you start to layer that on top of my existing life, and I don't even have kids so it just becomes staggering but also cost prohibitive to have just an individual do it.
My understanding of what you're talking about is the AI presumably can do the pattern recognition of, like, “it's the same process for the same people over and over and over.” You're repeating all of us are standing in the same lines with the same issues. [Meghan: Exactly] Build that tech back end, and then you have a human sort of navigating to your point.
The last mile, the final piece of like, “Okay, Niki has this unusual situation, but it's based on essentially what y’know, however many thousands of people moved in D. C. this year,” that's kind of what you're talking about as, as what you're going to deliver.
Meghan: Exactly! You know, the way we started Duckbill was actually taking a page out of Travis Kalanick's playbook [chuckles] when he was thinking of starting Uber. He hired a private driver and made that driver available to a handful of friends just to see how it went.
We did the same thing. It was the middle of COVID. We had some spare time [laughs] nights and weekends. [Niki: mm-hmm] We weren't going anywhere, and we hired an EA who had some extra time. She's still with us. Shalyn. She's amazing. And we made her available to a handful of families. And my ask was, my only request is that I get to see what kinds of things you asked for to test the thesis: Are these things repeatable and common across families, as you say, or is it really ad hoc all over the map?
And what we found was that y’know, while our to-do lists feel long, varied, ad hoc, all over the place, because they are to us, they are incredibly common and consistent across families, the kinds of things that any person needs when they move, getting your water set up and your license changed and your cable utility wound down at your prior home, whatever.
Those things happen over and over again for thousands of people across the country every day. And what we found was that the things people asked for was a list of about 70 items. Everything on our annual to-do list boils down to about 70 items, and no wonder we feel overwhelmed. [Niki: right] 70 is a lot of different things for any individual to take on.
That's a very manageable thing for a platform of technology plus humans to take on. And by the way, those things follow the 80-20 rule, right? So, the most common use cases are appointment booking, customer support, you know, calling your cable company, calling the water department, shopping, and home and car maintenance.
Then there's one-offs, right? Returns for e-commerce, dinner reservations that are ad hoc things that come up. And then there's the final bucket of urgent items. You saw a mouse in your kitchen [Niki: Oh, man!] or your car broke down-
Niki: [interrupts excitedly] The mouse is urgent!
[both laugh]
Meghan: You just need an exterminator to come take care of it today. [Niki: yep] Y’know, those buckets of getting you set up recurring items, one-offs, and urgent.
That's our bread and butter. And that's what makes up those to-do lists. And wouldn't it be nice if you had someone looking out for you and anticipating those things or being able to handle them to say, “I got it. I'll have an exterminator in your home by the time you get home from work today. No problem. We'll get we'll get that mouse out for you.” [chuckling]
Niki: And I think you're right. It is sort of these when you were talking about your personal life transition. And for me right now, I've never, I've never lived in, which is sort of unusual, but the way I grew up and then how I've lived as an adult, I've never lived in a single-family home.
So suddenly, I'm looking outside my new house, and I'm like, “These gutters are completely filled with leaves, which I think is a thing I'm supposed to do something about, [laughing] not sure what it is?” So it's also like this - I've just started adulting at 45, [Meghan: Lucky you!] but I'm like, “Oh wow, leaves are like a thing I have to think about now,” [laughing] but I don't even know what those things are.
So do you guys do, like, packages for moving? Is that something you're thinking about? Doing new baby packages? How do you think about the product offerings?
Meghan: Yeah. So, you know, one of the common things we hear is that the, the thing, none of these AI agents or our predecessors have really been able to tackle yet is the mental load of knowing there are things that need to get done, but anticipating them in time or researching, “What am I supposed to do about leaves in my gutter?:”
One of our members said to us, “I am a first-time homeowner. I am a first-time father. I am a first-time executive. Nobody is giving me the playbook for any of these three things until you guys came along.”
And so, what we provide is not only a, a receptacle for all those things that are worrying you. You can roll over at two a.m. and take your phone off your nightstand and say, “Hey, Duckbill. This thing is stressing me out. Take care of it?” [Niki: laughs] and then roll over and fall asleep at peace, knowing that by the time you wake up in the morning, you'll have a response. It also uses AI in a lot of cases to anticipate what you need.
It's still up to you how you run your life. It's still up to you how much you want to take on. But you have someone there, a true co-pilot, sitting with you saying we got you on those gutters or by the time you can see the leaves. “FYI, this often happens. If you'd like us to call someone to take care of it. Here it is. Or if you want a tool to take care of it, we can send it on over. You're not alone in this. We got you.”
Niki: And I love that you talked about democratizing this because, so there are a lot of studies that show if you can put money into saving yourself time. So, we've spent all this money on stuff, which again, having just moved, I'm like, “Burn it to the ground. [Meghan: laughs] What is this stuff? Why do I own it? I hate all of it.” But if you can spend your money to save yourself time so that you can have a life outside of just your to-do list, plus your work, plus the necessary things, that is money that there's a lot of studies that show actually increases your happiness in a way that buying things usually doesn't. It might in the moment give you a little dopamine hit, but it does not increase your overall life happiness.
So, the idea of democratizing it for people, because most people do not have the luxury of a, of one human not working, or having an EA, or whatever. So I love it. So, that's Duckbill.
I want to talk a little bit about your personal path. Raising money, what's that like? Being a founder, and, and maybe even quickly from where you started, like how you went on this career path and ended up where you are?
Meghan: I love this question because for so much of my career, I felt lost and alone, and like I didn't fit in the environments that I was working, and I spent a whole year when I was at business school, asking, interviewing people about “Tell me what you do all day?” [laughs] I wanted to find a place that I felt like I belonged and that tapped into my passions and my skill set.
So, I started in a very traditional business boot camp way. I was a consultant at Bain & Company. I then went to work for one of my clients, Bain Capital, as a large-cap private equity investor. And those experiences were invaluable. I learned the business toolkit. I am a far more effective operator because I started my career in those places.
But I remember hearing one of my colleagues In the wall through where I was sitting at Bain Capital one night, just chortling away while working on a leveraged buyout and thinking to myself, I want to find a job that I love as much as he loves this one [both laughing] because I was learning from people who are amazing, but I just, you know, that kind of large-cap investing role wasn't lighting my fire.
I found I was drawn to our management teams. I was drawn to sitting on the ground with them, helping them figure out how to chart their path, bring out the best in their people, do something that was harder than they thought possible. Y’know, run through that wall.
And it led me to think, “Gosh, Maybe operating is the way to go.” And yet, at the time, this was, y’know, over ten years ago at this point, operating was not something accessible. It wasn't something a lot of my friends were doing. It wasn't something that I saw a clear path to, and so I really did; I spent a whole year of business school interviewing people.
I even took a year and a half off from business school to spend at the Treasury, in the 2008 crisis era, on Tim Geithner's team at the Treasury and the Obama administration. And the fascinating thing about my time in government was that it taught me to be entrepreneurial. I think a lot of people would probably be surprised to hear that because the federal government is not often something that a lot of people associate with entrepreneurialism.
But every administration and, frankly, the Treasury during that crisis period was a period of entrepreneurship. We were building a crisis response apparatus that didn't exist before. And it showed me that not only did my skills that I learn serve me in that way, but that I was really motivated, inspired by getting up every day and being part of a team that was building something new to make the world a better place. [Niki: mm-hmm]
And I will never forget every morning walking into that gate between the White House and the Treasury thinking, “I can't believe I get to do this every day.” I wasn't getting paid much, and it's long hours are really hard, but I had never been happier in a job. And I knew that's the kind of role I wanted to do after business school, maybe back in the private sector. [Niki: mm-hmm]
I would encourage anybody who has the opportunity to serve in the public sector to do so. I would love to do it again someday. It's so meaningful. But y’know, to use a business model to make the world a better place in that in that same entrepreneurial way. And turns out, not many organizations were hiring untested operators into general management roles back in 2013.
And yet this little startup, Uber, was willing to take a chance on me, and I happen to love the product. I loved sitting in the backseat, talking to drivers about how the product was transforming their lives. I knew it was affecting me as a resident of D.C. at the time, and then back in Boston, making my life better.
And I dug in. I started as the General Manager of Uber Boston. Actually, before I graduated from business school, I would go to class in the morning and go downtown in the afternoon, and I never looked back.
Niki: You said two things that I want to revisit. So, one is the idea of the government being like a startup. I'm not sure most people understand this or know this, but when there's a change in administration, the White House is emptied literally of everything. There are not computers plugged into the wall.
You show up to an empty building. So the idea, I don't know if people know, it's like, sure, there's usually; hopefully I'm, y’know, fingers crossed, a peaceful transition of power, but then the staff shows up, and there's nothin’ there. And so they have to start from nothing. And then the agency: same thing.
When you have new political staff, you're building [Meghan: yep!] when you have a crisis like the 2008 crisis, which is unprecedented, right? No one had ever seen such a thing. It does lend itself to scrappy people. And one of the things that's interesting is Uber also had a lot of people from politics. So [Meghan: yes!], much of my team, which was the government relations and comms team, it was people from presidential campaigns.
It was a lot of people who'd been on these scrappy entrepreneurial gigs because it lent itself to a startup. [Meghan: yes!] So I think that's a really great observation you made that there is a parallel.
And then the second thing is the idea that there aren't that many operations roles, especially, and I'm just going to say it, if you're not “a bro who knows bros”, whose going to take a chance on you? [Meghan: Yep!] It's really hard to be told, “You can be a general manager, COO, CFO, CTO,” like, you just don't get those roles.
And Uber, because the markets were run as independent, basically interconnected but independent markets, created a bunch of mini-CEOs and CEOs. [Meghan: Yep!] So, I'm glad you called that out because sometimes those startups are where people if they want to get operational experience, that's where you really do have to take a leap and go.
Meghan: That's exactly right. I tell people, “Run into burning buildings,” [Niki: laughs] right? That was the 2008 crisis Treasury. It was Uber in those early days, y’know, and any growth stage organization, Oscar, Duckbill, like they, it's a place with an enormous amount of opportunity, a, a, an organization that either has wild growth ahead of it or is in a state of crisis, as y’know, the Treasury was back in the 2008 financial crisis, has unbelievable opportunity.
And it's not the place that's going to say, “Put that down. You can't touch that.” It's going to say, “Just grab a hose and start fighting this fire.” What enormous professional opportunity exists in those kinds of places where you can see a flame and say, “Nobody else is tackling this one right now. I'm on it. I got this,” and get unbelievable experience at a relatively young age or low tenure or, early stage in that organization.
Niki: Yeah. And it builds a lot of professional confidence. I mean, certainly for me, I just feel like not just at Uber, but I sort of, my whole career have run toward burning, [chuckling] burning buildings slash gas fires [laughing], and so it has built a lot of confidence.
So, okay. I want to end on- what's your assessment of AI? So we're in this hype cycle, in some ways the tech is still somewhat rudimentary. There's It's very hard to raise money at a startup right now, but if you're in an AI startup, it's a little bit easier.
I just love, as a final thought, your perspective on being in artificial intelligence. What's your assessment of the state of play?
Meghan: Yeah, it is an unbelievably exciting time, I think, for the technology industry, for AI, and frankly, for the world. There is incredible potential here and real risk [chuckles] and any time in history when we have had a new innovation that presents such enormous upside and also risks that go along with it.
I think there is incredible opportunity for really thoughtful contributions in both the private sector and the public sector. What's so exciting as an entrepreneur in this space is the playing field is still wide open.
It's not clear what the winning business model is going to be, where the clearest product market fit is, and that creates enormous potential. And I wouldn't be surprised if we see some many cycles of boom and bust here and a transformation of how we all think about AI. Y’know, back in the early days of the Internet, companies had Chief Digital Officers, which is now funny to think about, because everything most companies do has a digital component. And I wouldn't be surprised if that's the case with AI in the near future. But we're all figuring that out.
And there is such value to be had and to be created by organizations that can get at that intersection of technology in the real world and say, “What is the way in which AI is going to manifest itself across all these real world, different nooks and crannies of our economy and our lives?” And begin to make people's lives a little better using the tech.
Niki: I love this! And actually it sort of is a perfect way to end this episode. So I, I just commissioned a poll on AI messaging and sentiment. And one of my observations is we've been really clear about the dire potential consequences of job dislocation or a bioweapon being created, [Meghan: yeah] or, y’know, there's, there's people understand the risks, maybe not a real percentage of the likelihood that they're going to happen, but they totally get it.
It's the benefits that they don't really hear, right? [Meghan: Yes] So it's the things like your brights on your car. You no longer have to flip them on. It just knows when you need the brights on and when another car is coming. A personal assistant that's enabled by pattern recognition. The idea that you are going to be able to go into any emergency room, anywhere in the world in a rural area, and they're going to be able to translate any language.
The benefits are really specific and tangible but not well communicated. And the risks are so heavily publicized but more abstract. And so I think there's this real opportunity to look at those consumer benefits. [Meghan: Yes!!] And start to change the sentiment. It's going to start to feel more positive when people see and understand these little things making my life better are AI enabled.
Meghan: I couldn't agree more. And by the way, I think we as leaders have a responsibility to use AI for those purposes because everyday consumers, Main Street, the middle class have had a rough run in the last few innovation cycles, and it's high time that [chuckles] the population starts seeing some of the true benefit, the productivity benefit, the quality of life benefit from this technology and for all the reasons you mentioned in all those specific examples.
Every day people's lives stand to get a whole lot better. We just need to start delivering on that promise and run, not walk to that future.
Niki: I totally agree. It's wonderful.
I'm delighted, MJ, that you're in this space. It's so nice to reconnect with you and that this podcast gave us an opportunity to talk.
Thank you so much for taking the time to come on.
Meghan: It's such a pleasure to be here. I'm so inspired by what you're doing.
Thank you so much for having me.