S10E6: Democratizing Life Management for Every Consumer with Meghan Joyce, CEO and Founder of Duckbill

If you are fearless, you can figure out a creative solution to anything. That simple fact is so empowering. When you know you can figure out a solution to any problem, it sends you into any challenging startup environment to say, look, I might not wanna solve this problem. It might be too expensive or costly or inefficient, but I can.

Welcome back to season 10 of The Room podcast. Claudia, can you believe it's been 10 seasons?

Madison McIlwain truly cannot believe it will be 4 years of The Room with you this year. I'm thrilled to be back behind the mic with you for season 10. For all of our listeners since season 1, you truly have been with us for some formative years.

If you're new here, Claudia and I started The Room podcast with the mission of opening the door to the room where it happens, in turn sharing the stories from some of the world's most iconic founders and funders. All in an effort to inspire and educate the next generation of entrepreneurs. And thanks to you all, we were recently listed on the Forbes 30 Under 30 Media List for 2024.

So why us? We're two best friends who met as product managers in 2018, then realized as we were making career transitions into myself, founder, and Madison, funder, wanted to talk to the entrepreneurs that had built great companies. Since starting the podcast, I founded Pryve, a commerce payment startup. Raised venture capital, and have faced a ton of challenges. Madison became a partner at Defy VC, was the first investor in my startup, and is now at Harvard Business School and is a pair VC scout coming to the table with the fresh funder perspective.

Over the course of 9 seasons, we've had over 88 guests amassing over $50 billion in enterprise value, ranging from conversations with the former founder and CEO of Zillow, Spencer Raskoff, to Michelle Zatlin, the founder of Cloudflare, Grammy Award-winning artist Sierra, and the creator of Next.js and CEO of Vercel, Guillermo Rauch.

Looking forward, as we continue to expand both online and offline, we are excited to announce the Room Podcast Summit in summer of 2024. The best way to stay in the loop is to subscribe to both the podcast and our newsletter, which you can find at theroompodcast.com.

Before we dive into today's story, we have a few short messages from our sponsors.

Silicon Valley Bank, now a division of First Citizens, remains fully committed to serving founders, executives, and investors across the innovation ecosystem. As the largest banking team focused on technology, life sciences and healthcare, private equity, and venture capital, SVB is uniquely positioned to deliver specialized lending and financial solutions clients need to reach their ambitious goals. Find out more at svb.com.

Perkins Coie is a leading full-service international law firm known for providing high-value strategic solutions for startups and investors. Lawyers in Perkins Coie's emerging companies and venture capital practice support the most innovative entrepreneurs and investors in fast-moving and high-growth sectors across the country. While addressing the myriad of legal needs that arise when fundraising and scaling their business. The firm's tailored legal services are informed by an understanding of each client's discrete needs. To learn more about Perkins Coie, visit PerkinsCoie.com. Welcome back to The Room podcast. In today's episode, we dive into the transformative world of personal productivity and family management. With Megan Joyce, the CEO and co-founder of Duckbill. Duckbill is reshaping how individual consumers and families manage their daily lives by providing accessible, affordable personal assistant services, combining both AI and human expertise. Megan's journey from a childhood in the suburbs of Boston to an impactful career spanning high-profile startups such as Uber and Oscar has uniquely positioned her at the intersection of technology and social good. After attending Harvard undergrad and business school, Megan's career trajectory took a turn towards entrepreneurship out of a desire to address fundamental challenges in how families manage their responsibilities. With Duckbill, she is focused on democratizing personal assistance, traditionally a service only available to the affluent, reflecting her deep-rooted values in social justice and equality instilled by her parents' influence. The product experience of Duckbill exemplifies how our leap forward in generative AI and intelligent applications can change even the mundane tasks of booking an appointment or ordering groceries. In this episode, we explore insights and themes such as the balance of B2C versus B2B go-to-market, building cutting-edge AI platforms alongside human-driven services, and the societal shift towards inclusive support systems for working families. Let's open the door. I'm kicking us off today, but first of all, Megan, thank you so much for joining us today in The Room.

Thank you so much for having me.

We're delighted to share a bit more about your founding journey and tell more about who you are as a founder. But we like to start at the beginning with all of our guests, and so we're curious, where did you grow up and how has that shaped your view of the world?

I love this question. My upbringing had an enormous impact on who I am and what I do. So I was born in Boston and grew up in the suburbs of Boston and had a very standard white middle-class upbringing, very white bread. I've been excited and honored that my life has blossomed beyond that to open my eyes to big horizons. And that's been part of it, to want to see so much more of the world. But I'll tell you, my parents and their stories had an enormous influence on me. My dad grew up in the projects in Boston actually, and managed to find his way out, but it really planted this social justice seed in me and this lifelong mission to do whatever I was doing to advance social justice. And on my mom's side, my mom is this brilliant music therapist who took years off her career to be at home with my siblings and I. Because it was more expensive for her to work and pay for childcare than for her to stay home with us. And I know that this was a choice that she made given the circumstances she had, and she'd do it 100 times over if she could, but it really implanted in me this notion that the choice shouldn't be so difficult or so expensive. And that then had a big impact on my founding Duckbill to make it more affordable and accessible for families to have a choice. To do whatever is right for them and to get democratized, affordable access to help when they need it.

Thank you so much for sharing a little bit about your upbringing and how that now can be tied into what you're doing with Duckbill. And we're absolutely gonna dive into that founding story. But it's funny in hindsight to look back and say, okay, these were just things I took for granted or were true to my story, and then realize how they weave together to be what now is a shared mission that you have after building your career. And so we're kind of curious in that vein of early identity, did being a founder always feel on the roadmap for you?

No, actually not at all. If you had told me when I was in college or even frankly in business school that I would go on to found something, I think I would be quite surprised. For me, it's been a journey and frankly being a founder was secondary to this more overarching goal of maximizing the impact that you'd have on the world. And I know it sounds so cheesy, but really that's what has motivated me. Motivated me when I was at HBS to go take a year off and work at the Treasury in the aftermath of the 2008 financial crisis. It motivated me to go to Uber right after HBS and then to move on to Oscar after that. And as I've been chewing on this idea that people need and deserve more accessible, more affordable health. It occurred to me that one of the maximum ways I could have a shot at impacting the world and making people's lives better was to found this company that I felt so passionately about and knew the problem space so intimately. Well, it was a very personal problem. And so being a founder became that next step, but That leap was a scary one. And I think what I've realized is I love it. I love it even more than I had ever dreamed I would. And it draws on the same grit and perseverance and running through walls that I've used in these other roles. But I will say to anybody out there who has not been on this founder or bust path, it might be something worth considering if you think that might just be the way to maximize your potential and maximize your imprint on the world.

What I'm hearing you say around impact is there's ways to have micro and there's ways to have macro impact. And how do you wanna show up in your career such that you're going after both, but more often than not, one or the other? And becoming a founder ended up being that macro perspective for you. And you teased at this, but you ended up going to Harvard for undergrad and for business school. Go Crimson!

We have a Crimson room here today.

How did those experiences of those Hallmark educational moments shape your appetite for risk in your career, both as a founder, but of course, as you mentioned, your other moves along the way?

There's this phrase that is talked a lot about at HBS, and Madison, you might've heard this about, what will I do with my one precious life? And it's said so often and gets this cheesy eye roll from a lot of HBS students and grads at this point. But it's a really profound question when you think about how short life is, and it is such a privilege to be able to think on those terms and say, what am I going to do with this life of mine? And how do I want to spend these very short days that I have on earth? And so for me, in kind of marinating on that question in different ways, both undergrad and graduate, The question became, what am I optimizing for? And candidly, if it were income, there are lower risk ways to maximize income than going and being a founder. But for me, it really was about impact. And frankly, it was also a little bit about living a life that I am proud of and that I enjoy. We all work too hard not to enjoy what we do day in and day out. And so, For me, I was looking at that intersection of what do I love getting out of bed and doing every day, and how might I use that to have the biggest impact that I can in making other people's lives better? And for me, that intersection said, go to a high-growth company, go start this company. And frankly, it's not a risky one. Because if I'm optimizing for enjoying my life, this is the most fun thing I could imagine doing right now. And if I'm optimizing for impact, this is for me the way that I have a shot at my biggest possible impact. And will it work? I don't know, but you know what? I'm gonna work my tail off every day to maximize the impact so that it helps even a few people. And the positive feedback that we get from our customers every day are what keep me going, seeing that impact in real time.

Being able to hear the passion you have for the problems that you're solving and the people that you're building for is just so palpable. So, I'm excited to dig a little bit deeper into Duckbill, but of course, some of your other experiences were so integral along your career path to get there. So, I'd love to hone in on what you did after HBS. In 2013, you joined Uber, and that was really your first experience in the high-growth startup world. And you were a regional GM for US and Canada and really saw the growth of Uber over 6 pretty wild years. When I was at Uber, it was known that being a GM and more broadly being part of ops and city ops was really akin to running your own startup within a startup, doing what it took to launch new markets. That was really the bread and butter of what made Uber what it is today. Could you tell us a little bit more about why you joined Uber and some of your more Wild West experiences?

We could probably spend an hour on those alone, and it would be so much fun. Honestly, I was a passionate Uber rider. I loved hearing the stories of the drivers when I was sitting in the backseat, talking to them about their lives and what Uber was unlocking for them and their potential and their families. And I was one of those people who picked up the phone and called my city councilor when Uber said in those early days, this is at risk of being shut down. And I was struck by a company that incited that level of passion in riders like me to take time outta my busy day to find out who my city council rep was and then call them. Nevermind even just pay attention to that messaging. But part of the story is a very practical one, which is when I was coming out of HBS, I knew I wanted to try my hand at a general management role. Overseeing a P&L and a team. And the only companies that were willing to take a bet on an untested GM like me were startups. And so I had prior to HBS spent my time in large cap, Bain and Company consulting, Bain cap, large cap buyouts, big huge organizations, the US Treasury. And I thought that's the kind of organization I would end up in. I am so glad that none of those companies would've hired me because in falling backwards into this high growth space, I found my passion. I found my calling. And what I realized was that in a startup, in a high growth organization, there's nobody to tell you, put that down. That's not your job. It's like grab a hose and start putting out the biggest fire you see. And that to me is so empowering and so exciting. And if you're the kind of person who loves putting out big fires, startups, high-growth organizations might be a really fun place for you. And goodness knows there were so many fires to put out in those early days. There was the time we got a call from the Massachusetts Public Health Commission saying that there had been a rider who took a ride in a car with a driver who had later tested positive for measles. There was a measles outbreak. In Massachusetts in 2013, and they were asking for our help in identifying the drivers and riders who had been exposed. And what we decided to do was I would personally call all 21 people who had been in the car in the hours following that person being in the car and personally alert them. And I was dreading these conversations, telling people that they might have been exposed to measles. This was pre-COVID. It was before we'd all dealt with big outbreaks of this kind. And I was amazed by the response. To a one, every single person said, thank you so much. If this were taxi or public transportation, I never would've known. You never would've been able to tell me to make sure I'm up to date on my vaccines. And it really illuminated the power of what technology could do for this segment. There was also this time when suddenly Boston Public School families found out the night before a school day that they wouldn't have access to the school buses the next day. And an intern in our office said we should offer free rides to all public school families to get their kids to school back and forth. And we stayed up late and drew geofences around all of the many Boston public schools and offered free rides to all Boston public school families so they could get their kids to and from school. And an article was later published, got huge press, global press, and the best one said, this is an example of Uber's fearlessness. They didn't hesitate, they didn't pause. They said, we're just gonna do what's right. And it happened to be really good for business. It got us a lot of PR and a lot of rides, but it was fearless. And at the end of the day, I think that's what Uber taught me. That if you are fearless, you can do anything. You can figure out a creative solution to anything. And that simple fact is so empowering. When you know you can figure out a solution to any problem, it sends you into any dark room, any challenging startup environment to say, look, I might not wanna solve this problem. It might be too expensive or costly or inefficient, but I can.

Thank you so much for sharing some of those really foundational stories that paint such a great picture of the type of impact and the type of work that you do at an early-stage startup. I remember when I first came to Boston in 2014, I wanted to go to all these different places and Uber was the only way I could do a lot of the things that I did. And so for that precise reason, that's why I wanted to join Uber after I graduated.

I love that.

Plus one to the Massachusetts Boston Uber, Uber fam.

You just made my day. I love to hear that.

You know, transportation and providing better access is such a huge area of impact, but that's not the only sector that you really innovated in. How did you go from Uber to Oscar Health?

It was not my expected next step. I'll tell you that. For a long time, I struggled to imagine something other than Uber for my place of work, just because I felt so connected to with the mission and the great aspects of the culture, which there were many for a very long time. And I got a call about the Oscar role, going to be COO of Oscar Health, overseeing all operations and then eventually all clinical marketing and technology and product as well. And when I first got it, I brushed it off and said, I'm not a healthcare person. This isn't for me. But the more I thought about it and the more I learned about it, the more I realized that the similarities between Oscar and Uber were more than I was originally giving it credit for. They were both companies full of pretty outstanding people working to disrupt industries using consumer tech to democratize access to something that was previously only really available to the privileged that everybody needed. In the case of Uber, it was reliable transportation. In the case of Oscar, it was health insurance, health coverage, white glove healthcare navigation. Oscar Health offers health tech and health insurance primarily within the Obamacare space. So these are largely government-subsidized, lower-income people, many of whom are not native English speakers, who need and deserve healthcare like everybody else and were now all of a sudden covered after the passing of the ACA. And in realizing those similarities, I thought, this is actually the opportunity I've been waiting for because it has all those aspects of what motivate me at work and in a role that was the next step up, going from a regional general manager of the US and Canada to really the COO, the right-hand person to the founder and CEO, to really be a part of taking the company public, fundraising, interacting with the board in a way that I can learn a lot. It was an extraordinary experience. While I wouldn't have expected to land there, I loved every minute of it.

As you mentioned, as COO, you led a team of over 2,000 employees. You were there through insane top-line growth all the way to IPO, which is really an incredible part of company building that you were able to lead through. What key lessons did you learn from this time that helped you see what it was like to build a company at scale.

Thank you. First of all, that means so much, and goodness knows it was not always easy or pretty. People talk a lot about the similarities within an industry or within a category and how companies within healthcare or within tech face similar challenges and how industry specialization can be really helpful. What I've found is that companies within the same stage of their evolution also face really similar challenges. What Oscar was facing a year or two out from IPO was very similar to a lot of the challenges that Uber had faced one or two years out from its IPO. Shifting the organization's mindset from consumer engagement and growth into profitability and sustainability, bringing the workforce along, and especially knowing that a lot of people at the organization, both Uber and Oscar, had come for the mission. And were now asked to optimize for something slightly different or adjacent to what they had long been optimizing for— profitability, the path to profit. Cultivating an exec team who think of their primary role as working with each other as that kind of Patrick Lencioni first team concept, rather than growing and developing their own function within a silo. I often tell people it's important to feel connected to the product and the industry that you're working in. But also think about the stage because the job within a zero-to-one startup is different than the job of a high-growth company is different than pre-IPO is different than post-IPO. And some people love that arc. I love spanning the different phases and helping companies and teams navigate through them, but other people really feel passionately about a certain stage and there's no judgment in that. And I think you can learn a lot about yourself and help find yourself your dream job if you figure out which of those stages you love.

I think that's such a helpful framework for a lot of our listeners who might be considering joining a startup or what does it look like to work at a startup? It is so varying depending on the stage of company, maybe even less so than sector. So thank you for that tidbit. Let's dive a little bit deeper into what you're building now. You founded Duckville in 2022. Tell us, what was the initial aha moment for Duckville?

I mentioned I had been chewing on this idea for years, and I really had. The initial idea, frankly, came when I was at Uber. Over the course of my 6 years there, got married, bought a house, had a kid, and then another kid, eventually got a car of my own, all of which kind of exploded the list of personal responsibilities and obligations. And it had already been challenging to serve in a busy job when I was just looking out for myself. And then as my list of adulting items and responsibilities grew, and by the way, I had a partner who was working full-time, we kept asking the question, how do people do this? How do people have families and jobs and keep it all together? And surely there must be a solution or a trick we're not appreciating. And what I realized was that for centuries, including in my own home growing up, the full-time work of taking care of a family and a home often fell frankly to stay-at-home women, whether that was wives and mothers or grandmothers or aunts through intergenerational living, or frankly low-paid domestic help in many cultures. And yet the economy is changing. The workforce is changing. Families are changing. It is rare the families who today have access to full-time help or full-time person who is dedicated to caring for the home and the family. Half of the workforce is women. More than half of undergraduate and graduate degree programs are women. And yet it's not like society has changed to shift the balance of all that unpaid labor more evenly. It's not like our capitalist society has developed solutions that are affordable and accessible. And my theory for that case is, number one, it's really hard. It's a hard business case to crack. And number two, there are only so many women who have been founding companies and solving problems for people like them. And so I thought, this is a problem that needs to be solved. I stared at it for a long time and frankly didn't think the technology was there to democratize access to it. I didn't think there was a way to scale it. There had been a number of other smart people who had tried. It wasn't there until the 2020, 2021 timeframe when I started realizing what generative AI was capable of scaling some of the most difficult parts of this model to scale, the correspondence, the research, things like that. And I thought now might be the moment. And I struggle to think of a business model that I know so intimately or care so much about than really using this new technology to give society what I truly believe we all deserve, which is access to real, accessible, affordable health.

This lets me ask a question that I was thinking as we were talking. I'd love to dive more into the product behind Duckbill, but As you're talking about all these different operational moments and experiences you had across Uber and Oscar and now with Duckbill, was there a case at HBS that has stuck with you that you think about more frequently than you maybe would have?

So many things. This might sound like a cliché answer for anybody who's been through HBS, but the BSSE course, Building and Sustaining Successful Enterprises, I think it's called, which was started by Clay Christensen a million years ago and is now taught by, I think, multiple professors in his stead. I think about every day and specifically the challenges of being a large organization in innovating and continuing to stay a step ahead and the opportunities that an upstart no-name startup can have in really breaking through. You know, I don't think I'm naive about just how challenging it is to get a startup off the ground and to crack this category in particular. It's an incredible challenge. Incredibly challenging one. But I take hope from things like knowing that any problem can be solved— thank you, Uber— knowing that upstarts who have nothing to lose have the track record of disrupting industries. And that's what BSSE taught me. And after having worked now for like 10 years in a series of high-growth organizations, I've even seen the aspects of BSSE in real life of even how hard it is for a company the age of Uber or Oscar to continue to disrupt itself and just how early stage companies are set up for success by virtue of the fact that they live and die on it.

That's interesting, and I hope that's a class that I get to take. Also, I took us on a tangent there, Claudia. So back over to you for some more product-focused questions.

Amazing. Duckbill really focuses on what is called a copilot. Certainly a very hot word, especially in today's context and climate with AI. Tell us a little bit more tactically about the role of the copilot at Duckbill, how the copilot interfaces with customers, and how AI underpins your product.

Duckbill is a personal assistant for everybody that combines real expert humans and AI to give you real affordable leverage, just like a personal assistant would. What's different about Duckbill from all those other AI agents out there, even ChatGPT and the like, is that we are focused on the problem that we're trying to solve, and we're agnostic about which tool is best positioned to solve each step of that problem along the way. A lot of those other agents bring AI front and center and say, what problems could we possibly solve for you using this incredibly powerful tooling? Which in my experience is not the way to really good or solve real world consumer problems. The problem we're going after is alleviating you and your time and your energy of the things that you dread, giving you true leverage of a personal assistant at a, a price point you can afford. We bring together both AI and humans to do that. AI alone is not capable of true end-to-end leverage for everything on your to-do list today. And a human alone is not capable of doing everything on your to-do list end-to-end in an affordable, accessible way. But something really special happens when you bring the two together into the same space and each is allowed to do what they do best. For example, A large language model might be able to tell you the best process for updating your passport faster than a human could do that research. But a human is the one who actually takes it across the finish line by filing those forms and getting you the appointment. And I think of it similar to the question of if Uber had waited until autonomous cars were ubiquitous in order to start ridesharing, it wouldn't exist today because Technology within cars and mapping and navigating is wildly powerful, but there are lots of edge cases and last mile use cases, and that's where you need a human with their hands on the wheel. And so when you combine a human with their hands on the wheel of your to-do list, who is making sure everything gets across the finish line like you need it to, with the same level of quality and attention that you would, combined with the power of large language models to allow that model to scale. That's when the magic happens. And that's what is so unique about Duckbill's model and its incredible team of copilots and engineers who work side by side.

When dealing with the really tricky intersection of physical and digital, it might often be a question mark as to, is this product ready to launch? Do we develop the model a little bit more? I was recently talking to a founder that is just about to launch in the consumer space, and she's been so stressed by whether her product is ready for market or not. Megan, your team and your product spent about a year in beta before officially launching to the public. What factored into your decision to run such an extensive beta, and what advice would you give fellow founders like my friend on the right time to go alpha?

Such a good question. The reality is I took a page out of Travis Kalanick's playbook when starting Duckbill. Before he started Uber, he hired a private driver and made that driver available to a bunch of friends just to see how it would work and what problems came up and would people use it. And that's what I did. It was in the middle of COVID I was working a full-time job at Oscar, and I was intrigued by this question, whether large language models can make a dent here. And so we hired this incredible woman, Shaolin, who's still with us. Leading part of our operations team. She was an experienced EA and I made her available to 15 families that I knew and just said, this is a cost. I didn't want a false flag of whether people used the service. It was free. I said, Sean's $25 an hour. Use her for whatever you want or don't. But all I ask is that I get to see the high-level data of do you use her? If so, for what types of things? And are those things repeatable and scalable, or is it really just all over the map and we truly just need an army of humans to do this, in which case it wouldn't really scale. We blossomed that true skunkworks version of the product into a beta that frankly let us learn undercover. And I think this is this like old Uber paranoia that was implanted in me and will probably never die. But if I can grow my company under the radar without being out in public with all these big expectations or competitors with a microscope looking at what we're doing. I'm gonna do that for as long as I possibly can. And so what we found was not only were we operating— I eventually left Oscar to go do this full-time. We hired a team. We were able to hire some great people who were up for coming to work with a company in stealth. We were growing. Sure, word of mouth, people were like, you gotta try this product that I'm using. Can I get my friend or my brother on board? This is amazing. And we even managed to raise a Series A while still in stealth. I think people often think you need to be out loud and proud in order to grow. Like, there came a point this past fall that we said, okay, we're getting to the point where we now need the credibility of being out there in the wild and having some public presence in order to take our growth to the next level. But It worked for a long time, and I would encourage folks to not rush. Don't rush out of beta. There's a lot that comes in just being able to iterate and learn without the pressure of the microscope. The other thing that we were doing during that time in beta is making sure we weren't introducing any product features that we couldn't scale. What that meant in practice was developing AI and technology prototypes for everything we had humans doing. And that gave us the confidence that we weren't going to go out with a product whose product market fit was based on something that was inherently unscalable. And so what we did was we took that time and the very small MVP engineering team we had to build prototypes for everything we were doing. And that's when we really said, okay, we have the confidence to get out there because we know we can actually back up the destination unit economics that we wanna have here in this scalable model that we've been envisioning. And that's what gave us the confidence not only to come out of stealth and beta, but to take our growth to the next level because we knew we weren't going to be funding a negative gross margin product forever and one that really could never break even.

I love this approach of getting in front of iteration in a timeframe and in a scalable, sustainable way. As you said, not under the microscope and giving yourself time, which is probably the most valuable resource in starting a company. We've also had the Superhuman founder on, Rahul, who did a different kind of way to gate it. They were invitation only for so long, and he's talked on our podcast about that strategy, which in a way was a form of beta. And so just appreciate the approach you all took on not scaling infinitely immediately and having the foundation, cuz you knew going out too quickly would not necessarily help you in the long run.

That's right. It might help in the immediate term, but really not to build an iconic company that we know is possible here.

And it's a good reminder. We know that there's a lot of ways that you can do things, and it's great to see the creativity around what even is a beta. And then when is it time to let the cat out of the bag, which as you alluded to, you have. So first of all, congratulations on raising $33 million across a few rounds. Um, and most recently a Series A from incredibly iconic investors. War Runner inspired Grey Cough and War. Totally amazing. And we're really curious, as you were on that journey of going from inception to company, who was the first person that said yes to investing in you and Duckbill?

I love this question because I would not be here without these people. In reality, there were 3 that came in 2 groups. So the first was David Fialko at General Catalyst, who has been a mentor of mine since my early Uber days, and as much as anybody I know has a real commitment to finding diverse founders, really mentoring them and planting those seeds of you can do it before they even believe that themselves. David said to me a decade ago, when you're ready, I'm here for you. And I can't tell you how much that meant, especially from someone of that blue chip investor nature, as accomplished as David and who has seen so much like David. It really meant the world to me, and I think frankly stands out among his peers as someone who has put his money where his mouth is, literally, and really backed a far more diverse group of people than I think a lot of other fancy white male-based VCs have done. And the other people who were literally the first people to say we want to invest in Duckbill specifically were Alexa von Tobel and Lucy Deland at Inspired, who are two old friends of mine and heard about this idea that I was cooking and said, you need to go do that. And called me one day and said, check your email. There is a term sheet in there. We think you should leave your full-time gig and go start this company. And truly that was the catalyst. I would not be here if they hadn't done that. And they have just been incredible thought partners at every step along the way, all the way through the Series A. And so really, I am deeply indebted to David, Lucy, and Alexa. The three of them, I just consider fairy godmothers and father who I wouldn't be here without.

That's incredible that you've had really an army of people around you on the investor side who's pushed you into this unknown zone, but a space that you were excited to go into and learn through it alongside with them and get to launch what is Duckbill today. Going into the product a bit more on the team. You alluded to this a little bit, but it's such an interesting time in AI, and there's words that people are saying now that frankly, 2 years ago, no one even would've known what that meant. The models behind the product experience that you've built, how are you thinking about that more high-level strategy of proprietary in-house models versus partnering with more of the GPTs of the world and how that's informed your product roadmap?

The competitive landscape within AI right now is so fascinating and is one that business case studies and history books will pore over for how this new industry developed or not. I think it remains to be seen. I am super optimistic about this, obviously, but the playing field and winners here are very much to be decided. One thing we do know that is at the current moment in time, building your own large language model is exceedingly expensive, and you need to the tune of billions of dollars and not just capital, but an enormous amount of institutional energy on optimizing those models and their efficacy and their efficiency and the resources required to not only build that model, but optimize it day in and day out. And there are very well-funded and very successful companies who are building those utilities as we see them that we leverage every day. Our sweet spot and our competitive advantage, as I mentioned earlier, is really around understanding the— and taking that AI and putting it into an applied world where it can actually influence the real-world result. If you ask anybody today, how has AI changed your life? My guess is some people will say, oh, it writes my business emails before me, or it gives me some ideas on a blog post or a speech, makes my life easier, makes funny poems that I read at my friend's birthday parties, things like that. Very, very few real-world people have been affected by AI yet, and they will probably see that impact in the enterprise space first. I think consumer is even further behind. We have yet to really figure out what the winning business proposition and business model is within the consumer AI space. And so that's where we feel like at some point it might make sense for us to refine our own large language models or build micro models, small language models that we use in our own space. But for now, let's let those big utilities do what they do best and build on top of them to actually build the app. Application layer, and that's where our differentiation and our value comes in and where we think is the highest and best use of our resources right now.

That's a great segue into our next question around where you do think these application layer technologies are going and how you see yourself within the suite of products that are coming online.

So much of the value is created in the last mile. There is also an enormous amount of money created in selling the pickaxes. If you can be that utility selling pickaxes, go for it. I think it really is up for grabs. There will be money to be made and had in that more utility space. But for the rest of us, it's about the last mile. And in order to really understand the last mile, you have to understand the problem you're trying to solve. And this goes for both the enterprise and the consumer space. And you have to get in and understand the workflows. And understand where value is created in the chain, and then how to apply AI in meaningfully overhauling those workflows. The battle for that last mile is really only starting, and I think there's unbelievable potential there, and will be super exciting to see that evolve over the coming decades.

I love this framing of the last mile. I, when I was at Gap, we were doing last mile delivery, so it was much more in the physical world, but The idea of the last mile of where I could have technology supporting me day to day that would drive that outsized efficiency is huge. And as I said before we hopped on, I'm really excited to try Duckbill. I think I'm a prime candidate for using it. And the B2C experience of getting to be a business school student with a side hustle podcast, it totally is up my alley. How are you guys thinking about that B2C versus B2B go-to-market strategy? Maybe if you give us a hint on if you are thinking about going to B2B at some point.

We've had incredible inbound about a B2B product. We have employers who want to pay for this and offer it to their employees and say, this could be a benefit. And we're certainly open to that. We have a couple of companies who are paying for the product on behalf of their employees today, and that's fine. But it was a very strategic decision to keep the north star of the company in the B2C direction, and that's because I wanna build a product that wins for consumers, that really changes how consumers live. The minute you start selling to a B2B audience, you need to start thinking about what the B2B buyer wants, whether that's an HR benefits manager or some kind of procurement team. And they often value very different things than the consumer. And so if someone wants to pay for this on behalf of their employees, Great. We have a waitlist of companies who wanna do that. Like, we would love to have you on that queue, but we wanna build something that changes your employees' lives. And when we do that, I know everything else will fall into place. I know it will help with employee retention. I know it will help with giving companies a more cost-effective way to offer assistance to their people, but I can't take my eye off the prize at this stage in our development by building for anybody else other than that consumer.

I'm hearing you say it's a reframe of sequencing and when you go out with it, not an if but a when. So excited to keep tabs on that journey for your go-to-market. Just one quick question around being a founder. We talked to you a little bit at the beginning of how this wasn't necessarily core to who you were, but this passion and mission is what driven you into this career path. But being a founder is high highs and low lows. So maybe you could just touch on a little bit of a moment when things have not gone as planned in the last 2 years.

Oh my gosh. There's like several moments a day. I think probably both of you and any founder out there will nod and say like, yes, of course, this kind of adage that nothing is ever as consequential as you think it's going to be. You think as soon as we do this, all our problems will be solved. It never turns out that way. Success is what's added up after every 10% win after 10% win, and maybe a couple lucky breaks that get you further than 10% of the time all pile up together. And frankly, I think it's the will to get out of bed after a defeat, after a loss, after a disappointment and say, that's right, I'm gonna get back after it and do it again. And I think And that at the end of the day is what differentiates winning organizations, startups or otherwise, from everybody else. Because this is hard. This is so hard. If it were easier, somebody would've done it already. And so the game is, can you get back after it and continue learning and continue iterating and keep your head up and stay in it? The callus that you build over time as a founder of saying like, yep, we failed yesterday, we failed last year. Like, and you know what, we're still here and we're better than we were then, is what gives that strength to the team and allows them to keep going as well.

I, I just wanna pause and say, just hearing this as a founder that's getting punched every day, it's just so energizing and reassuring. Thank you for sharing that. I needed to hear that.

Of course. And don't ever let anyone tell you otherwise. Founding a company is the exercise of getting punched in the face daily. It is so hard. I still love it. Like, I still think it's the most fun thing I've ever done, but I just think we need to normalize that because people don't talk about it enough. And if you're a high achiever, you think, am I doing it wrong? No, you're doing it exactly right if you're getting punched in the face every day, cuz you're trying to do something that's really hard and nobody's ever done before, that takes a lot of work. And fear not, Claudia, you're in such good company.

Thank you. As we wrap up on time today, we chatted a lot about building Duckbill, but you are up to a lot of other things, including being a mom of two. Tell us, how are you balancing building a company that helps people take control of their to-do list while also building a family? Asking for a friend, AKA me and Madison, who will probably be on that journey in the future years.

I have to tell you a story that might be a little embarrassing, frankly. The other day there was this big storm in the Boston area and we had a tree down in our yard that was blocking the driveway. And my daughter, who is tiny, said, "We'll have to find a person for that." And I'm literally blushing telling you this story because believe me, I do not want to raise children who are like, "Oh, we'll have to find a person for that." Like, I want gritty kids who go out and move that tree themselves. But for And frankly, I realized it was her internalizing this ethos we are building upon, which is none of us should be spending time doing the things that do not give us energy. And if we can find people who, like, we have some incredible people who can, it gives them energy and joy to take a chainsaw and cut down that tree. And that's amazing. And you know what? Thank God for those people, because without them, I would not be able to be running this company and my husband would not be able to be doing the big job he has, and I would not be able to be spending time with my kids. And I will say right out loud, that is an incredibly privileged thing to say. It shouldn't be such a privilege. Everybody should have help that is affordable and accessible. It shouldn't be something, a privilege to say, We're gonna rely on competitive advantage and I'm gonna work with the support network in my community and in my system to have people who are better at cutting down trees to handle that. And I'm gonna do what I do best. And that's how we're going to build this ideal society, ideal community together. We had a bit of talk about grit and, you know, doing your own dirty work, but we also talked about, yeah, we are I'm so lucky to have help. And I think that's at the end of the day, the answer to your question.

I think honing in on the work that you are passionate about and good at and spending more time doing that is what's going to yield success is such a simple lesson, but also such an important one that I think we don't learn early enough in our years. So thank you for building Duckbill and the mission that you guys are on. Zooming out a little bit, we're gonna ask you the question that is really the hero question for our podcast. And we ask all of our guests this as we come up on time, and that is, who is a woman in your life that has had a profound impact on yourself and your career?

There are so many. I have been so lucky between my mom and extended family and so many teachers and professors and managers that there are so many I could list, but the one I will tell you about is my grandmother, my mom's mother, who was raising a family of 6 kids in the 1950s, '60s, '70s, and on the twilight of that child-rearing opportunity, decided to found her own company, which is something that today is all too rare for women and mothers and was even more rare when she did it. But she founded a local community newspaper to bring light to important issues in her community that she thought were really important.

Important.

And she never stopped till the day she died fighting for ways to make her community better. And that instilled in me this notion that the only way the world has changed is through a bunch of really dedicated people waking up every morning and committing to making it a little better. And so I thank her, Eleanor Mettler, for teaching me that. Since the day I was born.

Thank you so much for sharing that, Megan, and thank you for being on The Room today. It's been such a pleasure having you on, hearing about your journey and your story.

Thank you so much for having me, and we'd love to offer your listeners free Duckbill. Enter the promo code ROOM, R-O-O-M, for a chance to try it for free. We would be so delighted for them to try it, and thank you again for having me. It's so inspiring and energizing to speak with you.

Thank you so much for joining us at The Room Podcast. If you want more from The Room every week, subscribe to our newsletter at theroompodcast.com/newsletter. We'll be back next week with a new episode and inspirational guest. Tuesday, 10:00 AM Eastern, 7:00 AM Pacific. See you in the room.

Silicon Valley Bank, now a division of First Citizens, remains fully committed to serving founders, executives, and investors across the innovation ecosystem. System. As the largest banking team focused on technology, life sciences and healthcare, private equity, and venture capital, SVB is uniquely positioned to deliver specialized lending and financial solutions clients need to reach their ambitious goals. Find out more at svb.com.

Perkins Coie supports the most innovative entrepreneurs and investors in fast-moving and high-growth sectors, addressing their myriad myriad of legal needs. But the firm doesn't just provide end-to-end legal and business counseling to its startup clients. It also facilitates introductions to key advisors and sources of capital. Perkins Coie's interactive website, Startup Percolator, offers access to programs, resources, and rich dynamic content designed to assist entrepreneurs on their startup journey. To learn more about Perkins Coie, Go to startuppercolator.com and perkinscoie.com.