
Ideas Last · 2023-02-13 · 47 min
Key moments - from our scoring
Substance score
50 / 100
Five dimensions, 20 points each
Sagewell Financial addresses a largely underserved market: digitally-savvy retirees managing complex retirement finances. Rather than building the low-touch Mint.com-style product Zimmerman initially envisioned, user research revealed his target customer - young retirees with 70% of U.S. disposable income - needed a trusted banking institution, not a password-aggregation tool. Zimmerman's path to founding reflected his philosophy of prioritizing people and problems over abstract ideas: he spent years exploring the aging crisis as a systemic challenge comparable to climate change in scope, volunteered leading MIT's digital contact tracing platform (which reached 9 million users), worked as a quant in currency markets, and co-founded a travel insurance company sold to Capital One. His mom's retirement crystallized the problem: retirees face multiple income sources (pensions, Social Security, part-time work), complex tax optimization, Medicare bracket management, and major asset decisions (home disposition, legacy planning) with minimal institutional support. Sagewell positions itself as "payroll and benefits for retirement," helping members set their income tax-efficiently and manage budgets across decades. The company's product evolution - from prototype to full banking experience - demonstrates Zimmerman's commitment to iterative development and customer-centric problem-solving over pre-conceived solutions.
Sagewell helps retirees manage multiple income sources (Social Security, pensions, part-time work, investments), set their income tax-efficiently to avoid Medicare bracket increases and Social Security benefit reductions, and plan their finances across decades of retirement.
Early user research showed retirees were uncomfortable sharing bank passwords with unproven fintech companies but trusted established banking institutions; the target demographic preferred familiar digital banking analogs to physical banking rather than password-aggregation tools.
He spent years studying both climate tech and aging as systemic societal problems, eventually realizing the aging crisis was underserved by venture capital despite its massive scope, and his mom's retirement crystallized the specific pain point around retirement income management.
Sagewell positions itself as "payroll and benefits for retirement" - providing the income management, benefits connection, and financial wellness support that employers provide during working years, but designed specifically for retirees navigating their own finances.
Zimmerman looks for ideas meeting "head, heart, and hand" criteria (intellectual challenge, personal purpose, practical execution), and he writes an annual full-life obituary to clarify his long-term identity and evaluate whether opportunities align with who he wants to become.
Our reviewer’s read on each dimension, with quotes from the episode.
There are pockets of genuine operational insight - particularly around retiree psychology, the customer-service cost trap of infinite-time customers, and the banking-vs-fintech trust distinction - but they are buried under an extended career biography, an Iceland interlude, and generic startup philosophy. The novel-ideas-per-minute ratio is low.
the dirty secret in support is that you know 4% of customer service tickets drive 80% of the cost and most of that 4% is is my is was is is is older adults because of the infinite time they have
being a bank built online for older adults, people get it like there's like no, like they're fine to give their Social Security number because it's a bank
A few genuinely fresh observations surface - older adults prefer banking analogues over password-sharing fintech tools, and penny-pinching customers become unsustainable because of their infinite time - but the core frameworks (First Round's 'high expectation customer,' 'head heart and hand') are explicitly borrowed and widely circulated, and the pivot-story arc is a standard startup narrative.
they like analogs to physical real things online. And so pretending to be a weird bank account monitoring password thing is unfamiliar
a digital bank for older adults just has like that, like that like it could be an SNL skit, it could be a. And I wanted to be on that frontier
Sam is a genuine two-time operator - he built and sold a travel-fintech to Capital One and ran a 9-million-user COVID contact-tracing nonprofit - giving him real practitioner credibility; however the Capital One exit was self-described as 'more of a single than a home run' and Sagewell is still pre-scale, limiting the depth of at-scale lessons he can offer.
we had at our peak something like 9 million members, 9 million users across states and nations around the globe
The company was sold to. To Capital One. Like more of a single than a home run
The episode contains a handful of concrete data points (56 million adults on fixed income, 70% of US disposable income, 4%/80% support-ticket stat, 17-month build timeline) that anchor claims, but Sam repeatedly self-hedges ('I'm making up a number') and many product and market assertions remain at a hand-waving level of abstraction.
There's 56 million adults living on a fixed income
4% of customer service tickets drive 80% of the cost
The host asks generic, open-ended questions ('where do most founders go wrong?'), frequently summarises and validates rather than probing or challenging, and never pushes back on vague or hedged claims; the format is a friendly founder showcase rather than an interrogation of ideas.
So was that quick prototype, was that the first thing that you did, uh, when you started the product
where would you say you think most founders go wrong in building and growing their business?
Computed from the transcript - who did the talking, and the words that came up most.
Welcome to Ideas Last, the podcast about turning initial sparks into big results. On today’s episode, we have Sam Zimmerman. Sam is currently CEO and co-founder of Sagewell Financial. Sam founded Sagewell because he wanted his parents and the 57,999,996 other Americans like them to feel confident about their financial futures. Confident they are saving as much money as possible. Confident they are getting everything they have earned as seniors. Confident they are safe and protected from scammers who take advantage of folks their age. Confident they are going to be able to pass as much as possible to the next generation. Sagewell is an institute that specializes in banking for seniors. Sam shares his journey of how he came up with the idea and has built the company to where it is today.
Transcribed and scored by The B2B Podcast Index.
Speaker A: It has long been said that ideas are everything, especially in the startup world. But what if having a laser focus on your idea can actually hold your business back? In the Ideas Last podcast, Danielle Gillespie interviews startup founders whose success came from obsessively focusing on execution instead of ideation. Each episode dissects what it actually takes to build a long lasting, profitable startup, rather than simply launching one by, uh, putting your idea last.
Speaker B: Welcome to Ideas Last, the podcast about turning initial sparks into big results. I'm your host, Danielle Gillespie, and I'm excited to learn how top entrepreneurs turn their sparks into thriving companies. Today I'm talking with Sam Zimmerman. Sam is an experienced exited consumer fintech entrepreneur who is building a bank for his mom. Sam is currently CEO and co founder of SageWell. Hey Sam, welcome to the show. I absolutely love what you're doing at Sage. Well, and I'm excited to talk about your startup journey today.
Speaker A: Awesome. Thanks so much for having me, Danielle.
Speaker B: Great. So before we talk about your current startup, I'd love for you to tell me a little bit more about how you became interested in startups and a little bit about like your journey as a, an entrepreneur. Yeah, happily.
Speaker A: It's a great question. Well, uh, I, I start as that I was a math and philosophy major, so I studied a lot about how language worked, about mathematical models of languages. Really obsessed with that in college. And that led me to work at a startup doing machine learning and natural language processing. So my first experience at a startup was started my junior year and it was fascinating, really interesting work and I thought I was going to keep working at a startup until a week after I graduated, I discovered that the startup was going under, um, which was my first lesson in, in, in that industry. And honestly, I think if you'd asked me then I'd be like, never, I'm never going to work in a startup again. And so I, that, that experience got me recruited into the currency markets. They were looking at the time for a lot of like, machine learning. Like a lot of the techniques I'd been playing around with were, were interesting to, to those markets. And so I was a, I, I was a quant for my first job out of school. Move $20 billion around really fast, made some money along the way put. But I couldn't have told you anything about what I'd done in the world. I couldn't like, it was just, I just moved $20 million around and had a bunch of money. And that wasn't like, for the math philosophy major. That wasn't, wasn't super didn't jive with me. So I, I went to Iceland and read books for two weeks. Read a uh, Middlemarch and Brothers K and a bunch of. I can be a little dramatic. Love that it was, I would recommend it. So they've got open camping laws. It's really, it's pretty great. And yeah. And so I realized I wanted to build something. I really wanted to just like be able to be like I, I built this thing. I, I was really. I wanted to find real practical value and so. And at the same time I was really interested in the machine learning stuff. And so I did two things. I started working at a lab at mit, wrote up, ended up writing a paper or two out of that. And two, I worked at a consulting company that ha. Happened to have all the utility spend data transaction level and I there helped them um, machine learning to kind of switch from a consulting company to an AI company. And they were sold as an AI company a couple years later. And so that was that experience of like working with different stakeholders. It was a project that was kind of cut across data science, engineering analysts and marketing if we're, if we're honest. And I like, I love that process. I loved kind of taking it from kind of napkin up to something live. And after about two or three years of doing that I was like all right, I'm ready to be. I would love to get even earlier. And that means kind of building my own thing. And so I co founded a company with that was a riff on travel insurance.
Speaker B: Mhm.
Speaker A: So I was looking for that head hard hand. I wanted a really complicated financial model, a really complicated risk problem. And then I really wanted to work with consumers. And so we were a riff on what we do is if you had like an AMEX platinum card and you swiped your card, we would pull the information about the trip automatically and monitor your trip in the background with a pretty great flight monitoring solution. And then if your flight was disrupted, we would reach out to you, let you rebook in three touches on your mobile phone and focus on getting you to your new game. We actually had a. Yeah, everyone kind of has that story of when they had that flight that they. The wedding they missed or the event. And we just, we were a company that helped them do that, um, which was great. And it was. We had a hiatus NPS pilot and we were talking about all sorts of wonderful things in March of 2020 which is a really bad time to be a little baby travel insurance company. So we made a number of tough decisions and the company was sold to. To Capital One. Like more of a single than a home run, uh, scenario. But anything you can pull off in a pandemic as a travel insurance company I think is pretty great. Yeah, I was, I was, I was, I was, I was fine with that. And then I went and worked. I just, I wanted to. I really care about having impact in people's lives. And so I went and volunteered at this like MIT Covid nonprofit for. For two. And so I at the time they were just a group that was talking about using your phones to help contain the. Contain the pandemic. And it was kind of a novel idea. There's a couple other groups doing it and it just blew up into the world's largest digital contact tracing group.
Speaker B: My.
Speaker A: So we have yeah we ended up with at our peak something like 9 million members, 9 million users across states and nations around the globe. Really difficult. It was a research technology leveraging Bluetooth. We'd work opposite of Google and Apple and states and nations and we had a couple million dollars from a wealthy benefactor and but we were all kind of volunteering and that process of working like our okrs were like contain the pandemic which and we were, we were planning. I mean the technology was. Had it been adopted, it was like a lot of us, A lot of evidence suggests it could have been an uh, impact with the order of like masks or social distancing. And so it was having that experience of like a beautiful mission like aligning so many interests across states and technology and volunteers. It's like I want more of that. I want more like real mission with a capital M work and building. And so I built so I that technology never totally like we got to millions, but this is the sort of technology you need to get to billions in order to have a uh, real impact. And so we. I was thinking about what to do next and started a conversation with my now co founder Jeff, experienced insurance exec. And at this the lastly was helping my mom, a first grade teacher of 38 years retire. Oh wow. Yeah, she's. She was, she yeah raised, raised 4 kids on a teacher salary. Educated a bunch of first graders on how to read and Zoom came along and Covid and she'd been on the fence and she was like I'm ready to retire. And so this like kind of opportunity to think about like nations and states and systems and public health. This conversation with my co founder, a seasoned insurance exec Jeff, who's was. We aligned very quickly on you know, thinking about big problems and this experience of Helping my mom connect the dots across her retirement person who's, you know, super sharp, super with it, but. But where hadn't been thinking about her finances, but had a lot of other things to do. Those three things led me to found with Jeff Sagewell, which is I'm building a bank for my mom. And most of the folks around our team are building a bank for their parents or loved ones who, who are navigating the. Their end of life finances.
Speaker B: I think that that's great. I. There's just so many cool things you said there. First of all, is that, you know, I talk to a lot of students, college students, and they are having a hard time wrapping their head around going from first job to dream job, you know, and it's so hard at that stage to counsel them and say, you know, your first job is for you to actually like, look around and see what's out there. And you know, you'll make a series of small course corrections and you will end up someplace that you love if you're, if you're mindful of it. And I think that's, that's exactly what you did. It sounds like every step of the way you just, you stopped and said that, you know, is this what I want to do and what do I want to do? And go after the thing that you want? Um, which I think is an important skill set for a founder because you're always, you know, you don't just dream up an idea and stick with this idea. You look around, is there a problem? You know, you've taken all of your inputs and you've, you've been channeled in a direction that is meaningful, is rooted in a real problem. Your mom, not. Your mom's not a problem, obviously, but, you know, she's, she's, um, she's facing something that could be challenging. And you know, and, and do your research and figure out that, you know, this is actually, um, an interesting challenge that's searching for a solution.
Speaker A: Yeah, I think I look for people and problems before and frankly, like to a fault. I think a lot of founders, venture capitalists look for, they want vision. And I've learned that it's important to paint a picture of a solution, but in disposition and fact of how I think things actually go. It's like people and problems and listening and refining and mostly the. There's there. It's very hard to know exactly where you'll go. Uh, and so I definitely resonate with that. I have a crazy, kind of crazy practice that I think everyone should do. Around the point you just raised, which is each year around this time of year, I write my full obituary as if I have died.
Speaker B: Oh my.
Speaker A: So I write it as if I've died, lived a full life. And it's, it's, it's. I keep the format the same, like, same number of words as a normal obituary. But I think when people are navigating early careers and late careers, they're trying to solve two problems at once. Who do I want to be and how do I get to who I want to be?
Speaker B: Mhm.
Speaker A: And I think that for me, and I do think this is something that most people would benefit from, it's a little m morose, but I find it eminently, practically helpful. If you know where you want to go, then your question is, how does this path, how does this job, how does this problem, how does this person relate to who I want to be? Instead of. Which is a simpler inference problem. You're answering one question instead of two, or you're ritualizing one process. Who do I want to be? And it allows you to think much more practically and tactically about how you want to get there. So I, it's my, my end of year. It's a, My uh, my end of year practice is to sit down and write my obituary. And I think, I think a lot of other folks benefit from it too.
Speaker B: Yeah. So you, you said you, you write it from the perspective of you've lived for many, many years, not for you having lived as many years of you as you've already lived.
Speaker A: Exactly.
Speaker B: Yeah. Yeah.
Speaker A: As if, like, I mean, I don't say the exact year, but I think I. Yeah, like, I've had kids, I've had careers, I've had all sorts of things.
Speaker B: Yeah, that's cool. Have you already written it for this year or not yet.
Speaker A: Not yet. Probably in the next week or two.
Speaker B: Okay. All right, interesting. So let's, let's switch gears a little bit and why don't you tell us a little bit about Sagewell and what it does and you know, how would somebody interact with it.
Speaker A: Yeah. So Sagewell, our mission is, is to build a bank for our parents, young retirees navigating retirement. Our vision is to be payroll and benefits from for retirement when our members are the boss. So if you think about your career, the vast majority of Americans have an employer. They have a boss. And there's all sorts of negative things that come with that. Retirement is a wonderful era to not have a boss, but your employer does lots of things for you. They make your Paycheck, they help you through W2, they figure out your health care, they connect you to new mental health services or maternity and paternity support. That Gusto benefits platform just grows and grows and grows with features and support to help employees achieve health and wellness and navigate their finances. And then you retire. And for the average retiree today, they have multiple different retirement income sources, none of them sufficient. Very few have just kind of one pension. Most people have multiple retirement income sources. They have to set their income, they have to pay themselves. They have to connect the dots across all of them. And if they mess it up, no one tells you that. But in, in retirement, if you move money around the wrong way, it's realized as income and your Social Security for the year will decrease and your Medicare will increase and then your healthcare. These folks like read the newspaper to figure out whether you know, what will be included in Medicare this year. And they have a host of really important, vulnerable, complicated questions to ask and answer like what to do with the home that's important to the family but also is their biggest asset. You know, how, how long should they plan to have income for? You know, know, what do they want to give to their kids? What, what are their goals? And we don't think for the vast majority of Americans that there's an institution there that's they, we think that they would, they would benefit from an institution that, that does connect those dots, that does help them set their, make their paycheck, that does help connect the dots across other parts of their retirement. And so SageWell is a bank, uh, banking chime had millions of dollars calling themselves a bank and there was a lawsuit. So we're, we can just say banking. We provide banking specifically for retirees and helping them tax efficiently, helping them consistent with their budget, set their income, manage, manage their budget and have a plan for the decades to come in their retirement.
Speaker B: M. Yeah, I mean I think all of that is, it's really important. It's interesting is, you know, I talk to more and more of my friends who are trying to help their parents navigate and they now they're probably older than your target demographic, but they're still sort of in this situation where they don't really have so the, the, the children don't have an uh, understanding of what the parents financial picture is because the parents don't know. And you know, I hear over and over people say you know, or uh, my parents could have $10 or $10,000, we don't know. And it's just being spent in whatever way they feel necessary without any thought for how much longer they're going to be living again, like maybe a little morbid, but, but it's a, it's a real concern. Like, you know, how do you, how do you help someone, you know, manage your budget and you're saying multiple income streams and then what if, you know, even mid-50s, you decide to do some consulting work or you open a little business or a little shop or something, you know, like, how is that being managed and is that draining your finances or is it additive to the finances? So I think all of that is, is really pretty interesting and hugely relevant.
Speaker A: It's funny, we, we, we when we sat out to this, we fell in love with the customer, the young retiree, that is for us, that we needed them to be comfortably comfortable digital, like comfortable with technology. And I would have told you I would have built like mint.com for retirement. I would have thought that it would have been this sort of like low trust, nine or ten dollar a month. Enter your passwords and I'll make a plan and budget and you know, like Mint, but with all the retirement specific problems and functionality. And I distinctly remember early on in user research, I, I like made this, uh, our CTO made this really like lightweight Mint prototype and we were doing these user researchers and I would, I would go uh, on these calls and I would, you know, the user research that he was like, you know, $300. If you, you know, go work with this prototype, it will require you entering your bank account passwords here. Security. This is, we're building it for these reasons. And so like, they consented to it. They were like, yeah, I'll do that. And we, we gave them a lot because it was a very high trust. Very. It's very hard to kind of, it's, it's. Banking is a very, very, very sensitive thing. And they hated it. Even though that like, I, even though like the whole deal was that they had to do this. They hate. No one did it. I think I did four or five and I, I've learned that now I know that most of them don't know their passwords and the ones that do know their passwords don't. It's very high trust to just give a random company your bank account passwords.
Speaker B: Yeah.
Speaker A: And um, one of the user interviews, the woman was like, yeah, ah, I would never use anything like this. So I was like salvaging the interview and she was like, but I love my Chime bank account. I love digital banking. And I was like, oh, you and she's like, yeah, no, like. And that was when I realized that for this customer, that was the beginning of the insight that for this customer they are still very much non digital. They're very, they're very online, but they like analogs to physical real things online. And so pretending to be a weird bank account monitoring password thing is unfamiliar. Very high trust being a bank built online for older adults, people get it like there's like no, like they're fine to give their Social Security number because it's a bank. They opened accounts before they understand that the FDIC insurance is important. And for me, I think we fell in love with uh, the customer and the problem and the actual product solution was, was not at all what I thought it would end up being and was full of a lot of, a lot of good stories along the way to getting there.
Speaker B: Well, and that's really cool because I think a lot of entrepreneurs just fall in love with their initial idea and don't want to ask those kind of scary questions, you know, so you were willing to put something in front of people and let them be honest and listen, like listen and observe to kind of get to the root of, you know, why they're not, um, performing the behavior that you would expect so that you could get to a better place of something that people really love. So was that quick prototype, was that the first thing that you did, uh, when you started the product or. I mean a lot of, a lot of startup founders are curious like where to start. So I'm always just wondering where people decided to start.
Speaker A: Well, for me I have like several cheesy but true things and one is that I, I do look for ideas that are head, heart and hand and there's just not many ideas that I think meet those criteria. And um, there's a lot of ideas that meet too. I just had been for my first job, I realized that I really did need to have those three. And so I've been thinking for years, even while at my, my, at my travel travel company, that the two markets that I was most interested in were the climate crisis and the aging crisis. Um, and I think that the aging crisis is quite different than the climate crisis, but is comparable in scope and challenge from a societal perspective. Like I think population curves inverting is not something that we really uh, have any ideas how to support and, and think about. And so I, I, I advised a couple of climate tech companies, I saw a bunch of climate tech deals and I, a couple of them were successful, but I couldn't Tell you what a good idea what was a good idea and was a bad idea. I'm I like I I the problem was important. I saw lots of really smart talented people come running at it with really compelling interesting problem solutions and you know, two, three years later after advising I the one some of them work, some of them didn't but there I had no real insight as to I didn't think I had any expert knowledge and the exact form of the aging crisis. I didn't I couldn't have told you exactly where but I did know that was a massive market that did that the aging crisis it wasn't getting the intention that I think is is deserved of it and that I that population curves were changing such that digital adoption would enable digitally savvy older adults to problems in this stage of life in a way that so far haven't really happened online due to those adoption curves and and they happen to have 70% of disposable income in the US so they have the capital to rewrite and expectations that that will need to be met. And so I kind of directionally knew that I was interested in it's funny I was thinking at this kind of systems level quant perspective uh and then my mom retiring was a little bit of just this deeply personal to deeply universal that for me we did a tour around a bunch of retirement finance. It's a very nascent market. There's not been a lot of innovation. It's a lot of Web 1.0 type stuff like putting an annuity online, put X online. It's not really like marketplaces platforms like it's a, it's a lot of it is very and so we we did a tour of different potential solutions and before uh deciding that you know there's some really core challenges and income management that that would provide a lot of infrastructure for a set of other solutions and so yeah I would say my first cheesy thing is head hard hand. My second thing is that I I did devote time to both I was read I would read for years about kind of challenges and invalidated my expert opinion in the one that I thought I would be stronger at and was consistently drawn by the second one. And then third I like I think I, I I do think that you have to go where they're not and I I think that as you kind of heard in my my mid reasoning like the I this is a massive problem, a massive sector and most of venture is kind of pattern matching X, Y and Z do X for Y and I Think that my style, which um, is fine, actually I think they're probably more likely to be successful in long regards. But for me, I think I prefer to like be right at the boundary of like a joke and a great idea and like a digital bank for older adults just has like that, like that like it could be an SNL skit, it could be a. And I wanted to be on that frontier. Sorry.
Speaker B: Yeah, yeah, that's, that's a, that's a good way to put it. I call it entropy. Sometimes you're, you're uh, surfing the edge of between order and chaos. Yeah, you sort of, that's, it's a different kind of entropy. It's comedic entropy. Maybe. That's cool. So, so, so you, you determined, you know, sort of like the ballpark you wanted to be in and then product wise, did you. You built this quick and dirty prototype that you put in front of people. So in terms of building, was that the first thing that you created or did you, did you like, did you start building any. Like, I guess I'm interested in like how, when, what did you build and then how did you decide what else to build?
Speaker A: Yeah, it's a great. So we. So a. I would say like I'm a CTO turned CEO and definitely kind of biased towards product and iterative building and that I think I've. Has been maybe beaten into me. I would, I don't want to say that I'm like great at it. I feel like I just had have seen it done the wrong way and seen it like I, I uh, it's. It's more of a pained lesson than an intelligent lesson. But we started out with an insight that entering retirement is a psychological change for people. Like we did, we had these interviews and multiple people said literally word for word, every little bit helps. Like my parents in the pandemic went to a state an older adult appreciation dinner at their local bank. They were in line for three hours for a ham and cheese sandwich and they didn't know exactly what it was, but like they were in line for and like waiting in their cars for hours for a, A, um, sandwich. It was worth like, I don't know, not a lot of money. And we kept seeing in our user interviews this like very cost sensitive like behavior. And we realized that they have like infinite time retirees. Like one retiree said that retirement is the only job that with no days off, it's this like you have in a certain, like in a certain way you're in your third act. But in another way you have as much time as you'll ever have, and you have to stare at that empty calendar and figure out what to do. And you know exactly how much money you have. And you know, like, if you spend it, if you save a dollar, like that dollar, you know exactly what it means to your budget. What you have this, like, very felt, practical, intuitive sense of what saving money means in a way that if you're in a growth context, like, I'll. I'll make another million next decade. Like, there's just kind of this. You just. You. You're not in a growth context. You're in a spending down context. And so we, we started with that insight. We were like, well, if, like, what if we just built a deals platform? Like, what if we just tried to save our customers money? We know that they love saving money. We want to earn their trust. And we've seen a lot of different companies try to earn their trust, and we studied the ones that failed and we're like, all right, the trust is the major problem. And the way to build trust with this segment is to save them money. So we threw up a landing page and, and. And had a set of questions, type form questions, all sort of jazz all centered around like, you know, did you know that you can get a property tax exemption? Did you file your paperwork? Did you know that senior discounts are on Albertsons at Tuesday? And so that allowed us to get customers or that allowed us to get. And so that was very lightweight. M. And there was a lot of positive feedback that the top of funnel stuff was really promising. There was this kind of. It was a look like a lead gen sort of play. And. But ultimately what we determined was that that customer segment was going to be very expensive to service. Uh, they. So a. I mean, also the we. And we built the mint.com thing. It was like a plaid API integration. It doesn't take too long. Took like, I don't know, like a week to build a very lightweight version of that. Um, we weren't getting anyone online to do it, so we tried user interviews to. To get some feedback on that. But we thought we could do a lot more to save them money if we knew what they were spending money on. That could be our goal and we could, you know, you know, look for insurance, savings and all this jazz. And yeah, so, so they wouldn't do it online. We threw like a couple hundred dollars in and there was just no one who would bite on that. Um, so we went to the user research and we did a bunch of them there. And I think we also realized and we as we were doing our customer segmentation and for us like our problem, our market opportunity is so customer specific, customer centric.
Speaker B: Mhm.
Speaker A: Meaning like 80%. I don't know, I'm making up a number. 70% of our market will never ever you know do any sort of banking or wealth management with a fintech. They don't know what a fintech is. They're going to bank with their old buddy Larry who gave them a deal, you know who like they'll do their mechanic stuff on Thursdays. Like I'm uh, never going to displace Larry and I'm never going to displace you know, fidelity for people who just like want that big brand. So I have to find a digitally savvy, open minded, relationally oriented older adult and who is not gonna and this is an issue with this, this like bargain thing is that they, it turns out that that customer that like loves a deal also loves to drain your call center when they get, when they miss 50 cents on their like coupon that like we just quickly realized that we couldn't build a business that was servicing this infinite time penny pinching customer. We knew that deals mattered but it couldn't be anchor, it couldn't be the anchor because we, we couldn't service them in a scalable way. And like the dirty secret in in support is that you know 4% of customer service tickets drive 80% of the cost and most of that 4% is is my is was is is is older adults because of the infinite time they have. So then we're like all right, we have to switch target customers and we have to figure out which customer met those constraints and attach it to a business model to make sense and attached it to market opportunities and all that jazz. And so I could go on in pretty in in detail about the steps of how to get there but I think I, I, I'm fortunate enough to with our, our CTO Chris in my own experience to, to know how to. I'm as lazy as I can be until I know very much and have a lot of, a lot of confidence in m many parts of the business model from product product strategy. If you look at most of the companies that have come before us targeting this demo, they've been really poor products. They've tried to sell older adult software. Older adults don't give a shit about software. They don't care like they, they like want like real value in the real world and they'll do software to do it, but they're, they'll do it, uh, go online to do it, but they're not like, oh, that's a cute interface. They're like can I see the text and can I click the button?
Speaker B: And.
Speaker A: And did I do it right? Like they're, they're just not. And so yeah, I think for us it's. We, we had uh, enough technical fluence, enough of a lazy disposition and thought, enough with the business model, spreadsheet, product and market opportunity. I mean it took us, I mean realistically, it took us 17 months. I mean I was fortunate having sold my last company to be able to raise capital on market team and product direction. But, but it's my business particularly. And this one especially is uh, markedly tightly coupled across customer value, prop product, business model and opportunity such that any slight perturbations at any one of those knobs had, has pretty large reaching effects, which is fun. It's my game. I love playing this game. But it's meant that it's like I feel like a little scientist and I'm like, uh, various people around the company like when are you, when are you just gonna like run and start like scaling like crazy? And I'm like, well, we got like, it's a. I have a very clear set of like things we have to do. And we're actually quite close to that. But it's been far too often it's very easy to chase or optimize one metric due to the complexity of all of those like mutually constitutive complicated flows. And then what ends up happening is you end up with customer servicing costs that make no sense and you have to shuttle half your customers because you know, who are all pissed at you because you didn't, uh. So you end up with like, it's a. There's a million ways to hang yourself. And I think in this opportunity more than most I've seen, there's maybe 10 million ways to hang yourself. But that's part of the opportunity is kind of tight, tight walk roping across these very tightly coupled complicated constraints and doing so in an iterative, thoughtful way and then knowing when to dump money on the thing and scale. And I'm um. We're not quite there yet, but we're, we're quite close.
Speaker B: Sounds like you're pretty close.
Speaker A: I hope so.
Speaker B: Well, it always takes longer than you think it's going to take, but you know, it's where I think if you put the time and effort in up front, you'll find that you have much more success. Later on rather than just trying to, you know, release, release, release and you don't have any idea if anybody's even wants what you're putting out there.
Speaker A: We have a like, uh, foundational article for us. It's like in our okrs is there's an article by First Round Capital that talks about that the high expectation customer and building for the high expectation customer and finding your high expectation customer and they talk about that is essential to building your brand. And I would say that this company, more than my last company has been an exercise in finding your high expectation customer is a customer that. For Airbnb it was not the wealthy world traveler and not the couch surfer, but it was the, the customer like the, the, the consultant who had three months off and who like had the time to over research what where the best spot was and that would pay for good experiences but also like new quality but also wasn't kind of, you know, traveling in five star restaurants. That was the customer that Airbnb optimized for. They, they didn't directly take on the couch surfer that's looking for like, you know, the cheapest opportunity and like you know, free beer at the party on Friday. And, and, and that customer for Airbnb gave them the feedback, provided a self reinforcing effect that that customer is trustworthy. They, they're actually Airbnb central challenge was getting people to trust, you know, strangers to live in your home. And couch surfing had a lot of folks who you shouldn't trust live in your home. And, and so that was uh, you know, Dropbox's high uh, expectation customer was the, the person at work whose desktop you look at and you're like oh, that's cool. Like that. And they built like they, they got really good at that. Like you know, micro like desktop micro tool manager, like highly optimized workflow Persona. And what those two Personas do is if you acquire that customer and you service that customer, they'll put your business, the business model makes sense. They solve the core, hardest problems of the business model. Um, and they'll tell you what to build next. If you have the wrong customer, that's telling you what to build next, you'll build the wrong thing. Uh, and so I think for us we've been on the hunt for our high expectation customer, which for us meant that they were in retirement, that they were digitally savvy, that they were open to new products and experiences, that they would want support with a person, but that they would do things by themselves for some time or they would Find it that they valued paying for a service that they weren't kind of that penny pinching. You know I'm um, gonna take a dollar because I can type that they, they actually our customer actually has a. Most of them are care come from care careers and so they, they, they want our business to succeed and they're kind of happy to pay for goods and services that, that resonate with them and that I mean what I just articulated to you, you know, you know we're continuing to refine that but getting and finding that high expectation customer that you know makes the spreadsheet sing, that makes the brand sing, that tells you a product to build that's willing to pay and, and relentlessly finding that customer I think is, is I think the best brands and the brands I most admire have, have started there as opposed to a particular product idea or particular like it's a. I'm um, starting with your high expectation customer I think is one of my, my major learning from this brand.
Speaker B: Wow, that's great. That's, that's um, pretty cool. So, so your customer is it an uh, online product, A uh, mobile product? Both.
Speaker A: So we're a platform. I mean it's m. Banking is kind of, it's one of the challenges of consumer banking is that you have a lot of large product surface area. Kind of from the get go you. They expect to be able to you know, mobile check upload on their phones. They expect to use things on your desktop. So we are platform, we are Omni mobile desktop iPad. A lot of our customers use iPad. We have multiple financial products. So for us uh, a part of our core belief is that we're trying to switch people from a savings mindset. How do I pile more and more money onto my money pile and grow that money pile to income? Now that I have this money pile, how do I take it and make myself an income that you know, allows me to achieve my standard of living. So that entails having both banking and investment services. We need to kind of have a view into and be able to structure and support that pile of M money and all of the ways it should grow and protect you as well. Has have an eye into what you're spending, your budget, your bill pay, your um, your the Social Security check that's flowing through your system. And so we have, we're a platform with those two core products really tightly coupled and we are at the moment kind of building a lot more of functionality that sits in the middle between those banking and wealth management.
Speaker B: Gotcha. That's that's awesome. It's a huge undertaking, but also pretty awesome.
Speaker A: Yeah, every so often you're like, so I mean my, my last. The nonprofit. Like if that server was hacked, it could have brought down an election. Like oh, like State of Minnesota's, you know, exposure notification server. Like I, I don't know of a piece of infrastructure that has more potential. You know, if someone hacked that and spammed a bunch of exposure notifications on election day, like uh, uh, you're in trouble.
Speaker B: Who knows? Yeah.
Speaker A: And so I'm, I'm used to. I. In fact I love and excel in high risk, high compliance, high trust contexts. This one is like when you build the bank, like you have the keys to the vault and we have a bunch of protections in place. No one person can do it. But every so often you're like, wow, I got the keys to the vault. That's a big vault. Gotta make sure that we got it protected. Gotta make sure the bank robbers aren't coming. While we are not legally a bank and m. We offer banking through choice banks charter and our SEC registered robo advisor in a, in a, In a uh, in a very colloquial sense of the place that has the money. We were very much thank.
Speaker B: Yeah. Wow. That's a lot. That's so. That's. It's just, it's awesome. I love it. I love, um, I just love the thought process and I really like hearing how you, you know, kind of moved through your various options and you know, kind of got to the place where you are now and you'll continue to take that, that thoughtful approach to what are you building next? Why are you building it? What are you building and does it make sense and, and this, this highly engaged customer. I, I fully believe that the. You, you know, your, your m. Most, your power users are the ones that really have a great insight into what could be coming next or what you should consider putting on your roadmap. So that's all, that's all really cool.
Speaker A: I would encourage for entrepreneurs out there finding capital, finding. As you think about fundraising and you think about proving this out, I'm uh, um, like every many people at many times will push you to scale this before it's ready. Mhm. And they'll push you or they'll just be exhausted. They just, they're ready for the next stage. And as you're thinking about building a business and you're thinking about capital venture needs to scale quickly. But power laws are power laws and you need to have the right initial conditions for them to hit. And my advice to young entrepreneurs or entrepreneurs who are excited to do this is be patient, uh, and have people around you who are patient until they're not. The thing about scale and the thing about these opportunities is they are very small, but if you build them right, they can scale incredibly quickly and build wonderful businesses. And all too often people are obsessed with the scale and don't think about how hard the initial conditions are or they don't have people around them who believe and trust that they are, that they are kind of focusing on that venture back of opportunity and that, that, that you know, X, Y and Z does need to be resolved before we're ready to go. It's weird, but it's. In an industry that's all about speed like patience is, is a major virtue. And having people around you who trust in your competence that, that patience is not kind of uh, otherwise an issue is, is something I would as a, my second time through, I would say can't understate it.
Speaker B: Yeah, I fully agree. I've, I've seen a lot of entrepreneurs kind of rushing through the process and I, it, uh, honestly it like pains me to actually watch it happen. And you know, sometimes it's their own drive and sometimes it's the investor's drive, but it's, I mean you have to, you have to. The, the patience is important I think to really hit the ground with something that people are going to love. Uh, so, uh, where would you say you think most founders go wrong in building and growing their business?
Speaker A: You paint me a picture of the founder. I think different founders have. I said just because like a first time founder, a second time founder.
Speaker B: Oh, a first time founder. Let's do that.
Speaker A: A very simple one that I think is hard. It's a simple and hard thing is you are always going to be wrong. You're, you're at uh, any one time an investor, an employee or a customer is not mad at you like you should, you know, buy a lottery ticket. And I think that a very common failure pattern is to not acknowledge that you're, you're in the wrong or to not sacralize it. I think the people uh, who I think do this best love to be surprised. And as long as they're making new mistakes like that's, that's generating information and learning and surprise in a really important way. So my first, you will be both simultaneously needing to paint a very clear, strong vision and confidence that you can lead in a host of different people with very different incentives and very different motivations and very different backgrounds. And so you need to be very clear and strong minded. But uh, that does not mean that you're always right and in fact you mostly will be wrong. And more importantly, you need to build companies and cultures that sacralize and value being surprised, trying new things and learning. And if you don't model that, your company culture will fail and for the vast majority of opportunities, that culture will doom the enterprise.
Speaker B: That's great. That's a good take. I like it a lot. And then just for the last question here, is there something on the horizon that you're looking forward to, that you're willing to share? It could be anything. Personal, professional, company. Hmm.
Speaker A: M. That's a wonderful question. So one thing that entrepreneurs have, it's like they're on the border of like a, a good mental illness is we tend to be just like insanely optimistic and insanely pessimistic, but like deeply optimistic. And there's a moment where, there's a moment in a company where you can see that the arc of the company is progressing at a pace and scale where like exciting things are going to happen. Like, it's not like, it's like, it's not like there's a period where you're like, and you're just like, oh, we have it all figured out. And then you don't have it figured out because this assumption is totally wrong and you have to do all this stuff and you're like, you know, actually months away. And like that process happens for a really long time. It's like a, it's very common. It's very hard to estimate these large things. But the reaches in a point in time, when you have the problem clear enough in your mind, you have the major variables, you have the major challenges and issues, you've assembled the people to like address those issues. You see the progress being made and you're like, you know, like this thing's going to sing like, like this, like this. Like if things just keep going as they are and this, you know, we, we're not there yet, but like we've solved far harder problems than this and we've got to figure this one out. But you know, there's, we can do it when I'm there in the company and I for our opportunity. I mean the, the U.S. there's, there's 56 million adults living on a fixed income. Like take whatever haircut you want. If 70% disposal, like take whatever haircut you want. This is a, a really big, exciting opportunity with a differentiated Product and a important and that worth with customers who have real issues. And I don't know, I think that. What am I looking forward to? What. I'm excited. I think like for me we are. We're dangerously close to a very exciting scaling plan and I can, I can see it.
Speaker B: And that's a really good one. It's a fairly, really fun time.
Speaker A: We're not bored. Like it. And maybe you can follow up with me in a couple of months maybe, like. Because the tricky thing is that you can think you're there often and you're not, but I don't know. It's. It's the sort of mirage. Like, it's. It has a mirage like character, but at the other hand, like, it. It's a bit like your math homework too, where like you kind of get the problem in your mind and you're like. And then you. Yeah. You get enough headway where you know you can solve. Uh, feels much closer to that than in. And so I, I'd say that's. That's. That's the energizing feeling. I, I have too much energy. I have to go for runs all the time.
Speaker B: That's okay. No, that's. I think that's great. And I, I think you do know, I mean, like, you've put the time in. You've. You've done the reps. You've, uh. I, I think that your, Your, Your, Your optimism is probably warranted, even though you. It's never as close as you want it to be. But I think you're probably. You're. You're close. You're like, you're feeling. Your sense of being close is. Is probably a good one right now. So I think. I think you're on the money. My money's on you. So this has been awesome. Thank you so much for talking with me. I love hearing about the journey you've been on and how Sagewell's going, and I can't wait to see what happens next for it. And it's just been a really great talk.
Speaker A: Thanks so much, Danielle. Have a wonderful, uh, evening and wonderful holidays, everyone.
Speaker B: Thank you, Sam.
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