Duckpins CEO Lauren Cappell on Launching a New Business Idea | builders podcast

0:00That's really kind of where the starting point was, was how do we help people get a handle on what has traditionally been thought of their paper life when we live in a digital life.

0:14today i speak with ceo lauren capel about the business she has just launched called duck pins it's a really big business idea about creating managing and storing the documents that every adult really should have throughout their life whether it's a power of attorney will trust etc and in doing all of this for the digital age we discuss why lauren chose this category her career career working with a venture studio and you get a real sense for a day in the life of a CEO in the middle of a company launch.

0:51Hi Lauren, how are you today? Good to see you. Good to see you too. Thanks. I'm good. And you? I'm great. You've got to be really excited. Your new company Duckpins is launching in the next week. Probably as folks listen to it, it will have been launched already. And it's a really big, big category. Tell the folks listening about the business, about Duckpins and what you're trying to solve for. Sure. Yeah. And it is an exciting time. It's been, as always, a long road to get to this point. And so it feels nice to be at that finish line. Duckpins is a service that is there to help you create, manage, store, and share life's most important documents.

1:29And it sort of spans kind of, I think, multiple categories. And that's what's a bit interesting. We are starting with helping people draft and execute what's traditionally thought of as estate planning documents. But we didn't come into this with an intent to solve for estate planning or probate or anything like that. And I think a lot of the people that I look at in this space are really focused on that. When we started thinking about this problem space or general area, it was really about thinking through how I felt like my life was a bit of a mess. And obviously I'm being a bit simplistic, but I mean, my documents are all over the place.

2:06You know, I created a will when I had two kids, I lived in one state, I moved to another state, I had a third kid. We, you know, you buy and sell homes or assets, you move places and it's all a bit, you know, none of it is properly captured. And I just sort of, when I looked at my own life, I thought like I'm pretty organized with my work life, but all of this paper stuff in my life is all over the place. And so that's really kind of where the starting point was, was how do we help people get a handle on what has traditionally been thought of as kind of their paper life when we live in a digital age?

2:39And as we started digging into it, the fact of estate planning documents being an area where there really isn't as much tooling, functionality, help, and online help as you need, really stood out to us as a good starting point. But the broader perspective was really, you know, as working people, we have all these amazing enterprise tools to manage stuff. And when it came to managing your home life, it's all sort of on Gmail, in a desk drawer, you know, maybe if you're really fancy, use some kind of document storage online, but very few people I've spoken to have done that. So it was really about sort of not just about creating documents, but really about taking you sort of end to end from creation all the way through getting them executed, which is a key part.

3:27A lot of the problems that we heard about were people have certain documents, they print them off from an online service, and then they sit on their desks for months because they've never been notarized or witnessed properly. And they don't even know how to do that or where to do that. We often heard people had their documents, but they didn't even know where they were, didn't know if they were current. And so part of it is helping people know where they are by storing them in one place, by giving you the ability to share your documents with other people in your life who need to know where this stuff is.

3:57And really you're building for that broader set of people around you and then helping you by removing some of the sort of obligation to keep your documents up to date. And so I think that's a big piece of it too, but it's really about focusing on what you need for your life as opposed to thinking about death, which is, I think, what you often see in this category. I was really excited when I heard about the business because you're creating your will, your power of attorney, your other documents. You're getting them witnessed and notarized and signed, like everything to make them legally binding in the software online and then storing it.

4:38And I understand there's been legislation around allowing you to do all of this online where you couldn't necessarily do it before. Actually, I was talking to folks at dinner last night about it and they were telling me, both of them were talking to lawyers and they're like, how much is this going to cost? They're telling me that they're spending like $2 ,500,$3 ,500 creating these documents the paper way. So I know you're going to tell me a little bit later about how it's different. Actually, maybe I could segue to now in one sense, which is there are other companies that have online document support.

5:19I can think of LegalZoom being one, or I think there's one called Trust and Will. How is Duckpins different than that? Because I know you talk about Duckpins as like an evolution of that. Yeah. So maybe what I'll do is I'll start by just talking briefly about sort of the online will piece, because I think it's an interesting... Again, when we started looking at this space, we didn't know anything about that. But as we dug in more, it became clear that there's some interesting developments on the legal side and on the sort of like legislation side that make this an even better opportunity and show more promise here.

5:53And so the difference or what an electronic will is, it's a document that's created online, you know, on any kind of platform, but also notarized or witnessed and signed online. So all digital, you know, using remote online notary services where they, somebody comes on a video screen with you, like a video call, and you sign your documents and they notarize your witness at the same time. And then as you say, those documents live on as digital documents, not paper. You can always print out a copy. You can even print out what's called a certified copy. But the point is it becomes a digital asset as opposed to a paper asset where you're going to store the backup online.

6:33This is one where the original is in fact an online document. And there's about, I think, 13 states that now offer electronic wills and sort of acknowledge the validity of an electronic will. And I think that number is only going to grow as we move forward. And I think it makes a lot of sense. And I think even beyond the will space, there's other legislation that speaks to other testamentary documents. So things like you said, powers of attorney or trusts or health care directives also being able to be executed online and stored online. and those being valid. And, you know, I get people worried about, is this valid?

7:10Am I going to be able to show this to someone when I need to show it to someone, whether it's a doctor at a hospital with a healthcare directive or a probate court or probate official with my will or anything like that. But the point is, that's where the world I think is moving. And in the US, we're already seeing that in 13 states. And I think this is only kind of then accelerated by COVID where you had a bunch of people who wanted to buy homes or sign their wills or write a healthcare directive. And we needed to be able to find a way to get them to do that legitimately. And so the infrastructure to enable this has grown, but I think there's so much more we can do to help with creation and management and storage of those documents.

7:54I think management and storage are key parts of it from what I'm hearing. And the management part is really interesting. My own story is my wife and I were, um, we're going to go to, uh, Europe for our 10 year anniversary. And we realized we didn't have our documents in order. We went, we went in and, and got some with, with a lawyer. And that, that was great. Since then, that lawyer has retired and there are all these things that have changed in our life. We, you know, we've moved the potential guardians that we have might need to change and stuff like that. It's not easy for us to take those documents and like, and like update them, but it's, It's not it like when I think about in the digital world, it shouldn't be that big of a deal, like update an address or like say I had a third kid and I want to do the same things.

8:40It's really cool. I think that that we're now at a position where we potentially do those things. So not only do we want to make it easier. And like you said, yes, you can modify your will or another document or you can write an amendment to it called a code of sale. But you can also, you know, part of it is getting it done. Right. Like saying, I want to change my will. I want to add a third kid or whatever. Making that decision, finding the time, finding the time to make it a priority and getting it executed. But I think more importantly, it's just not top of mind to update your will when you have a third kid or when you buy a home.

9:16And we're all in that space. Everybody's busy. They've got a lot going on. And I think traditionally, culturally, we think of a lot of these estate plan documents in particular as being kind of scary. something I don't want to think about, something I don't want to engage with. And so even if you did think I've had a third kid, I should probably update my will. That's never going to make it to the top of your list, right? It's just, especially if it's not super easy to do. And so part of what we want to do is make it really easy for you, in part by taking the burden off of you to stay up to date.

9:48So yes, you're going to have to decide if you want to update your will. But if there are public records databases that give us a signal that something your life has changed, we can scan those databases, say semi-annually, and send you an update. Like, hey, it looks like you moved states. Do you need to update all of these documents to ensure they're compatible with the state you're now living in? I'm not suggesting if you don't do that, that you're in big trouble and your will is totally invalid, but there might be things you could take advantage of in your new state, or there might be different things that have otherwise changed in your life that you want to update for.

10:25And we can at least give you that push to say you can do it. And not only can we do that, we can say, we actually took the liberty of rewriting your will with this new asset or reflecting the laws of your new state or acknowledging that you've had a third kid and we've assumed you want to keep everything else the same. Why don't you review it and let us know if you want to kind of redo your will, like top to bottom, change lots of things, or is it just about adding an asset or changing it to ensure it complies with the new state or anything like that? And again, then hop online through our platform, connect with our third party notary provider, and you can have it executed in minutes.

11:00The other thing that you said, I think, which is really, really interesting, is you talked about there are these these documents like in the event of your death. And then there there are documents you need or really any any adult needs a different stage of their life. I have a child that's about to become like not a minor. I don't know if that's a major or whatever, but not going into the doctor's office with him anymore. He wants my opinion on medical issues, but I don't necessarily have the right to know those. Or the same thing with an aging parent or things like that. So there are all these parts where legal documents can really help you.

11:43But again, you've got that same issue of it's not top of mind and it's not easy. Yeah. And I think that's part of it too, right? Like regardless of whether you call it estate planning or something else, you know, the use case you just gave of, you know, a kid hitting the age of majority, right. And maybe going off to college, you wouldn't maybe think to go to them and say, like, it's time to talk about your estate, right? That feels really weird, but you could say, talk to me about, you know, do you want me to have access to your healthcare information? If so, you should sign this authorization to release medical records because under federal law, you as a parent would need that to be able to access his healthcare records.

12:20And I think that's super important for all of us as parents to have when a kid hits a certain age. And you could also have the discussion with them, you know, if you're open to it around a healthcare directive. So what are your preferences? What do you want? You know, because these are, again, things that might only come into effect if something bad happens, unfortunately, but I think it's important to have that in place. And I think it's also important for us to sort of change the nature of the conversation. This is maybe a bit of a higher level than the question you thought you were asking. But the reality is we kind of live in a world where people are living much longer lives, in some cases, healthier, in some cases, not entirely healthier lives.

12:57And so I think it's really important that we sort of slowly open up to changing the way we think about these things and ensuring we help the people in our lives know what we want. I love kind of understanding the roots of a story, what leads someone to want to run a certain type of business. And it struck me that this is a really, really big problem space or opportunity space. You were at Amazon. I was too, although we didn't cross over there. What were your experiences there or maybe in other places that prepared you to think about a business with such massive potential and such like a big area to play in?

13:36Yeah, I mean, I think so much of what I did at Amazon was amazing preparation for this, not the least of which is that I'm building this with Jelly Collective, a venture studio that is filled with ex-Amazon people. And that's how I ended up working with Jelly Collective. So part of the preparation and maybe even the most important part is that I am working with this venture studio that is filled with ex-Amazon people. And so the beauty of it is that we come from different Amazon businesses, different functional areas, whatever, but we speak a common language. And I think we sort of refer to that as a bit of a cheat for us, but it's been an amazing cheat because you just don't have to go so deep when you're working with people you don't even know that well because you know you've all approached problems in a similar way.

14:22And it goes well beyond sort of thinking about a peer FAQ and like how you would document your first sort of approach or thinking around a problem space to, you know, really everything sort of how you communicate, how you disagree, how you think about structuring your thoughts, how you think about scaling, right? what you're going to do first and next, how you're obsessed with the customer. I mean, I think really a lot of those leadership principles or LPs from Amazon still guide a lot of what we do, you know, whether that's customer obsession or ownership or inventing and simplifying, you know, those are all, I think, a big part of my training to do this, but also just what enables us as a group to work so much more effectively and efficiently.

15:10but specifically with the training i think the leadership principle around invent and simplify is a big part of it you know you really get great training at amazon for how to look at a space where things were kind of quote-unquote always done one way and say well let's take a step back and not only if we've never done this before but if we don't even have like the background in this industry how would we do this and um part of my career at amazon i spent in health care at Amazon, running BD across Amazon in healthcare and life sciences. And I think that was maybe one of the best kind of training grounds because I went in with no background in healthcare life sciences.

15:48And it's obviously a highly technical field, highly regulated, super complicated. But without having that training, you know, what you do is you do two things. One, you go find experts who can help guide you. And two, you're sort of free to think much more broadly and differently about a problem space. And I think that's kind of what we're trying to do here. So it was a really good experience and good parallel in some ways. I think also what's really nice is that Amazon, because even when you're working in an established big business at Amazon, you're often, I think most people are encouraged to do kind of that exploratory thinking work of like, well, what would we build if we started from zero?

16:30And so for me now being, for the first time in that zero to one space of starting a company when you have nothing and trying to get to launch in your first customer. You do a lot of that at Amazon and you do it in a fairly condensed manner. And that's sort of like writing the press release and the FAQ when you want to build a new business, right? It's sort of, you have that practice of saying, I want to go do something different. How do I convince all these other people that it's a good idea? And so that goes well before trying to actually build something. But that idea of wrapping your head around a new problem and how you approach it.

17:03And what are the questions you need to ask and answer before you get started, I think is, is, has been great training. I love that answer. And I wonder if folks have picked this up listening to some of the words you use, but, but way before Amazon, when you started your career, you were a lawyer. Yeah. And, uh, and so probably when you're giving specific legal terms, people might've, might've picked up on that, but you, you practice for five years or, or so. And I, I would, I guess I asked the question, did you always know you wanted to be an operator kind of transition away from law or did that just sort of, sort of happen during the course of you starting to practice?

17:41Yeah, I had no idea. I mean, I was one of those people, I think, well, a, one of those people who grew up in a family of lawyers and be one of those people who loved, loved, loved law school and never loved the practice of law. So, you know, I worked in a great firm in Canada where I'm from with amazing, brilliant people. And I was happy to go to work every day, but it was never the perfect fit. And, you know, it's kind of amazing that I was there for five years, having just told you it was never the perfect fit. And I think I did know that all along, but, you know, you come out of law school, like you come out of any professional program and you're, and you're goals oriented and you're like, well, how do I do this?

18:21How do I do that? How do I show that I can do this? And sometimes it takes a long time to sort of sit back and go, do I even want this? And so for me, that's what I did was I, you know, at some point five years in, I sort of said, well, look ahead at, you know, do you want to be a partner at this firm? Do you want to be, do you aspire to something more? Do you, is it this firm that you don't want to be a partner at? Is it another firm that would suit you better? And I sort of said, no, like if I was going to practice law. This is the best place for me to do it, but I don't think I want to practice law.

18:50And I had found at that point, I was just sort of doing some reading. In fact, what drew me to leave law was, this was in 2010, I think, and the news industries were changing. So, you know, newspapers and publications were starting to go online and they were starting to put up paywalls and trying to figure out new business models. And I thought it was such a fascinating transformation of a traditional industry and an industry that I have a lot of regard for. And so that's kind of what started to motivate me to go look for other things. But I had no intention of leaving law. And lots of people around me saying, like, go in-house at a big company, like go be a lawyer in-house somewhere and continue practicing law.

19:39Try doing it in a different setting and see if you like it anymore. And I think I really came to the fact that I wasn't happy practicing law. And so it was partly being sort of interested in the news industry. And partly also I found at that point, I was working in bankruptcy law. And I found when we were working with clients that I was more interested in the business problems they were trying to solve than the legal sort of machinations of how to get them the result that they wanted. And so it was a combination of those two things that kind of pushed or pulled me out. And I ended up getting a lucky break and getting a job in business development at BlackBerry.

20:14And and that's, you know, really within the first month of being there. And I wasn't at BlackBerry for that long, but I knew right then that I had found the right kind of place for me, that I was like had a totally different attitude to work than I'd had before. And so I got lucky. And I think in some ways, like for a former lawyer to move into the tech world, I took a business development role. In fact, working on getting newspaper, magazine, and book content onto BlackBerry, their phones and tablets. It was kind of a dream role for me. But doing a BD role is one where you can really leverage your legal skills, right?

20:52Yeah, totally. Write term sheets and contracts and then hand it over to BlackBerry Legal, who maybe didn't always love me, but ignore the parts I didn't want to deal with. But in terms of structure and deal, you've kind of got this cheat that allows you to move really fast. At some point, it sounds like after BlackBerry, you moved to Thomson Reuters. I don't know if that was directly after or sometime after. But one thing I thought was really unique about that place is they have a rotation program. And Amazon has a rotation program also where at Amazon, you're encouraged to go to different companies, different business units, different functions, because their feeling is as you learn more different types of the business, you're going to find your perfect role and it's going to be good for the company.

21:36Um, and it seems like that would advice I would give to anybody. If you're going to be in a big company, try to get, try to have one that's, that's a rotation program. What would, what would you recommend? What was your experience like, like there? And, um, and what'd you learn through that? So from BlackBerry, I went and did my MBA over in Europe. And, um, I think Thompson Reuters recruited on campus, like in the first six weeks of the program. And so I remember I think I had actually sprained my ankle playing either soccer or rugby. I don't remember which. And then I had to get over to London for the interview.

22:10And I remember going around on crutches. And it was like not a good scene overall. But that's how I ended up at Thomson Reuters. And it was sort of, again, like in the news industry, which is why it appealed to me and why I took it. But they had this management rotational program. And that's what the interview was for. And I had a real debate about taking the role. And so I hope this is sort of helps answer your question. The debate was because, you know, this was a company in the news industry and that's where I wanted to be. And when you do a rotational program, you're really expected to move through their different divisions.

22:42So they have a finance, they have tax and accounting, they have news, but news is actually much smaller. Right. And they have a legal business. And, you know, they actually wanted me to start in a legal business. And I kind of hemmed and hawed and I almost said no in the end because it wasn't where I wanted to be. But I took it and I think I took it for a good reason. And in terms of recommendations I give, I think big companies, it can be really hard to get started. It can be hard to build your network in a big company. It can be hard to sort of get visibility, both get visibility on your work and get visibility into how a company operates.

23:19And I think those rotational programs are designed to do that for you. And I think that's a gift. And so I think there's a lot of value in doing it. I also got good advice at the time that was, you know, I know you think you know what you want. And in the end, I think I was right that news was the best place for me at Thomas Reuters. But they said, this is the path upwards in this company. And you have got a spot here if you want it. But if you go and take, we can get you a job in the news, you know, business, if that's really what you're focused on. But I think it's to your disadvantage. So I sort of it was almost put to me as like, take the hit, don't see it as an advantage and take the hit, do the rotational program.

23:56It will benefit you in the long run. And I think that is true of companies that offer those programs. I think they're built in to help people navigate a really big company much more efficiently. And I think separate from that, where they are really valuable is if you don't have clarity on the kind of work or the kind of industry you want to be in. And so then it's just like a freebie. Like you get to go spend six months doing product work and six months in finance and six months in a BD role and six months, you know, I don't know, doing something else. And that's you're never going to get that, you know, at a more senior point in your career to have that opportunity.

24:33And so if you're not sure, it's a great way to get that exposure. It can also be a great way to build your skills as a generalist, right? You don't have to do something forever, but you learn the basics of marketing, you learn the basics of finance, and then you sort of take those skills. And I think it would make you sort of a better generalist or GM in the future. Yeah, it's probably a good segue back to duckpins because you don't get to just have a single function as CEO. You're kind of everything, especially at an early stage. Thinking back over the last nine months, six months, 12 months, what have been maybe some of the challenges of the biggest challenge in incubating this company?