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The Front Page of Global Fintech

The the largest fintech community in the world. Subscribe to our newsletter to stay up to date on the latest in news opinions, and all things financial technology.

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This Week in Fintech: Special Guest Jillian Williams

Nik sits down at Money2020 with Cowboy Ventures' Jillian Williams to talk about the defining moment of the decade, what lifestyle changes we'll see in our lifetimes, and (of course) fintech.

This Week in Fintech: Special Guest Jillian Williams

Hello fintech friends! This week, we have a special podcast episode with guest Jillian Williams of Cowboy Ventures, who sat down with Nik at the Money2020 MoneyPot Podcast Stage for a candid conversation on life, the universe, and all things fintech.

This Week in Fintech Special: Guest Jillian Williams


fintech, people, companies, world, feel, happening, starting, money, bit, absolutely, honestly, big, terms, interesting, durbin amendment, point, build, investor, products, biggest.


Nik  00:00

All righty. Hi everybody. How's it going? You've got Nik Milanovic and Jillian Williams recording live at Money2020 In the MoneyPot. Hey there, Jillian, good to see you again. Good to see you as always really excited to have you on the show. Hey, FinTech friends, the podcast that we've been doing for about a half a year now. And it is normally hosted by the fantastic Helen Femi Williams on our team, but she has otherwise occupied in the UK. And so I hope to be somewhat not mediocre replacement for her.

Jillian  00:43

Bet you’ll be great.

Nik  00:46

It sounds like you'll carry the conversation for us both if I mess up. So no pressure. Good to have you on. I think that you're probably like one of the most well known people in FinTech, but for the sake of our audience, who may not have come across you before, we'd love to just get your quick background and overview and what you're focused on today.

Jillian  01:05

Absolutely. That's very kind of you. But I'm Jillian Williams. I am a principal at Cowboy Ventures. We are an early stage venture fund. Seed focused, generalist focused on the US and I focus on fintech. So I've been focused on FinTech for last like seven years. Previously, I was at Anthemis, a FinTech fund, and then was in traditional finance before that.

Nik  01:26

So what brought you into fintech? When you start your investing journey,

Jillian  01:29

Jonestly stumbled into it. I was in financial services, like financial institutions group at Barclays. And it was just like good timing, where they were starting to focus more on fintech. And because of that, I like being Junior there, they kind of just pushed us towards figuring out what was happening in the new like that next wave of tech. And I thought that was a lot more interesting than what was happening with the large asset managers, insurance companies, obviously, now, like, joke's on me, because I still have to deal with a lot of them. But I realized I really love just working closely with the people who are kind of building for that next generation. And so that was kind of my foray into it. I wouldn't say that, like I immediately loved in tech. But when I realized how much I understood it and what was happening in it, I kind of grew to fall in love with it.

Nik  02:21

Yeah, I feel like it's not as intuitively exciting as like some maybe more like consumer friendly areas when you get involved to start with

Jillian  02:29

Exactly when all my friends were like getting free products from their, like, from their companies that they were meeting with. And I was like, Well, no one's giving me free money. I was jealous, honestly.

Nik  02:40

My credit card, my bank account are still held with a like Big Five bulge bracket Bank, which is like embarrassing for me. My head I'm like, oh, maybe that just means that there's like still more banking space for FinTech to capture, capture. But really, anytime I like without my car to pay for something people are like you're a trader. And, you know FinTech has, it's interesting, like talking with somebody who has kind of this longevity of investing background and exposure to fintech. You know, a lot of people have become FinTech investors, for the first time over the last call it like three years, which really felt like an inflection point in FinTech. And we'll get to that in a minute. But you know, myself included, I think that FinTech now looks really different for an investor than it did a few years ago. And I'm kind of curious, like, what still gets you excited? You know, you've seen kind of multiple cycles now in this space.

Jillian  03:30

Absolutely. I mean, you've been around the FinTech space for a while. So I feel like you've been seeing whether it's not directly as an investor about from the outside as an operator. But it's interesting, because I think when I joined in the US in 2016, there were very few people in FinTech, I remember, especially in New York, especially on the female side, there were like probably four of us. And so the same four of us, like did everything together, because I only became very good friends because like, we were the only people who would like talk to each other at any like, honestly events. And so it's funny just to see how much that's changed and how exciting the FinTech world is now compared to Ben. And so I mean, I think it's such a massive industry globally, that even with kind of the growth in popularity, and what's been happening both ebbs and flows in the market. There's, like, I'm still extremely bullish of it. But obviously, the past two years have just been kind of like the Wild West, where, like both in terms of valuations both in terms of like the number of whether it's like the exact same companies all popping up and all getting funded. Or even, like, honestly, probably some unnecessary companies that like you don't need X, Y and Z for like, I don't know, like a new bank for every single thing that giving you rewards and like some things that are probably irrelevant. And so I think that's something that you're starting to see weed out a little bit but I think honestly, that's more of a testament to like the infrastructure that's been built and people realizing what can be built. And so I think what's interesting is like, as that falls away more of the things that are like long term sustainability will continue to grow out of it. And so I think that's what I'm excited about. And also, it's the, like, kind of, in my view, the first time that we're having, like, mafias really come out, where like we have all of these, like, really big companies have been built in FinTech. And now we can have those exciting people that are leaving those companies actually build the next wave and people that I know FinTech really well start to build

Nik  05:37

Our market going to ask you to name those companies that don't need to be built. But it's true, there's like, it's been such a it's been such an attractive money pot from like a founder perspective, because it's almost like you had a guaranteed venture check if you're starting a FinTech company for the last two years that maybe some spaces have gone like over verticalized. But to what you're saying at the beginning of your comment, it is really cool kind of how the composition of people in FinTech has changed over the last couple years to like, it's finally like a hot area to work in. I feel like it was kind of the unloved tech child for a long time. You had to have these like hyper nerds who themselves are just, you know, working in, you know, obscurity at a bank for 10 years and saying like, there's a better way to do this. But when you're competing with like Fang companies for talent, it's like, well, we don't have any free lunches. And we're not working on a problem that your parents will ever know how to understand.

Jillian  06:24

Exactly. I remember telling someone that was like excited about some insurer tech company at one point, and they just like gave me the weirdest look. And I was like, I do get I'm the weirdo here. Like, that's fair.

Nik  06:34

Yeah, I don't know. There's something to love about that, though, like unsexy areas, it just feels like there's a better opportunity to go in there and be smart about what can be done better. You're not kind of chasing the same problems that that everybody else is chasing completely agree. And now that like, you know, in the last YC cohort, there are three Buy now pay later companies, which like for me, you know, knock on Buy now pay later, there's like fantastically successful companies and category but I'm like, How much more can really happen in this space in a different way? And maybe we need to like see like a little bit more like normalization in FinTech?

Jillian  07:08

Exactly. And I mean, I know that probably happens, or not probably it does happen in every sector. But that is absolutely something that you're seeing more and more of, and I think that also is a factor because of how much help or easily is, you're able to build FinTech products as well, like an endless we are early investors into simple bank. And like, it took years to be able to build the initial bank because you didn't have infrastructure company is like snaps, unit rides, etc. And now that those exist, you can spin one up in like months. And so because of that, you can have copycats so much more easily that if something's taking off, someone can just be like, You know what, like, that worked. I want to build that. And so you miss that, like, drive that a founder has to like, actually why they want to build something.

Nik  07:55

It's so annoying, honestly, I like where were the service providers when we were building pedal? Well, when we were building funding circle, we could have used like fraud KYC out of the box, we could use like you kids don't understand how hard it was to build a fintech. But I know that you get a lot of time, not just at the conference, but outside of it, and in interviews to talk about FinTech and to talk about your thesis and your path as an investor. And so I was hoping maybe we could use this time to just draw outside the lines a little bit and go off field and just talk about kind of broader themes, especially like those that tie back to this base, but just see where the conversation goes. I'd love that. So thank you for helping me by putting together some really good question prompts for the conversation. I'm super curious to dive in to some of the bullet points that you wanted to cover. And so we might as well just start at the top and work our way through. Let's do it. So for anybody listening, Julia and I kind of talked about what conversation topics we could cover outside of fintech. And she had some fantastic suggestions. And I'm really excited to hear a little bit more on these. And so we have three general question prompts that we're going to try and get through today. And the first one is what are the three moments that defined FinTech in the last 10 years? What were the three kind of biggest inflection points that happened in this space over the last 10 years?

Jillian  09:24

All right, I guess I'll start. I think probably the first one that I'll say is the, I guess, like the passing of the Durbin amendment, because that was in 2011. It's a little off of 10 years ago, but I think that that was just honestly like fueled a lot of what has been been tech revenue for the last 10 plus years. Now, in terms of in terms of interchange fee. I think most recently, probably this past month has been increasing amendments to the Durbin amendment that may continue to change that and interchange fee The revenue hasn't been as loved anymore. But honestly, that created the opportunity for so many fintechs like time, current, etc. To exist without charging their customer and to compete with the large institutions in a way where it's like, hey, these companies are charging you tons of fees, etc. And we can actually give you a free offering. And so I think that honestly just propelled that space from a consumer standpoint, in a huge way. And I think honestly, probably more than any other regulation that I can that I can think of impure, impure, FinTech honestly.

Nik  10:39

Totally agreed. There's a great write up that I read from ao Majola who used to be blocking I think, is a carbon health called like children's urban, but he was just talking about how like that waterfall created. I couldn't agree more. For me, one was, this isn't obviously it's not like people say this a lot. But I feel like the plaid visa acquisition was kind of a watershed moment where for the first time you saw that like, a large scale with a $5 billion price tag that there were a possible existent FinTech and that kind of precipitated, you know, all this late stage activity, all these growth rounds. And then like this back wave, you know, money line nerd while I painted all these companies that went public over the last few years in FinTech. And so now for the first time, you kind of have proof that it's like a multi company category, and that it's a really viable asset class at scale. And that you can just indefinitely kind of tranche up like different companies that can actually still grow. And my guess is, over the next year, you know, in the environment we're in, we'll probably see a lot more m&a activity. And so it's kind of interesting to see how that shakes out with these acquisitions and kind of what that says about the exit landscape, but it feels like that really kind of kick started all this.

Jillian  11:49

It's funny, because when that happened, it was such a huge deal. And then I remember it wasn't like six months later how everyone was like, wow, Visa got was getting that for a steal like that. So well. And then now, like, some people are like, yeah, maybe that should have like, we they probably wish that went through like, who knows now just given how quickly how quickly the markets have changed. And so it's crazy, just how much last like year and a half really, how much

Nik  12:15

It's kind of stuff because like MasterCard that acquired Felicity and I think either acquired, like, has a strategic partnership with like tanking Europe and it's like, yeah, these apply fell through yet. MasterCards got an open banking acquisition now. Yeah, somebody I was meeting with earlier at Chase was telling me that plaid when the acquisition happened was a top five venture return acquisition of all time, which like blew my mind.

Jillian  12:40

That's crazy. I didn't know that. I mean, but to your point, I think plaid in general was also on my list. As just a guest. That's not like a moment. But like, some thing in FinTech, that was huge, because it really unlocked almost everything else in FinTech in a way that I don't think most people actually think about. Because your bank really just owned every single aspect of data of yours. And especially in the US, like there was really no other way of getting that. And for most of the companies that exist now, they usually need Platt or now like there's MX, ethnicity, etc. But like, eventually need one of these companies to be able to exist. And so I think like the existence of plaid and the fact that like, especially early on, now they have more partnerships, but like they were scraping your data, they were being shut down by the banks constantly, like they were doing everything kind of like a backdoor to get into stata was like really huge for growing the FinTech space, and even enabling all of these other apps to exist. And so that's something that I constantly think about that, like how massive of an opportunity to plaid was.

Nik  13:49

Yeah, totally agree. I mean, that's kind of perfectly, you know, one of the inflection points, I guess, or kind of key dynamics that was really interesting to me over the last 10 years is that you have this move down the stack. And a lot of people who tried to solve second order problems and realize they should be working on first order problems. I think Stephanie overt or am is a good example where she wanted to build basically like real time intelligent money movement, and like automatic optimization, I might move in and realize, oh, there's actually like a fundamental problem about like, how money is able to move in real time we're gonna go down the stack and plaid feels like a great example of that. Yeah. What are some? What are some other moments or other kind of big trends that I think

Jillian  14:27

the another one for me is? It kind of goes back to like, Alright, so the Durbin amendment is probably the biggest regulation I think of but other things that have been the big biggest catalysts in FinTech have honestly been like the macro economic. I don't know what the word is, like, macro environment events have been the biggest catalyst. So I think of like COVID FHA is a more recent one has been a huge one, especially in terms of consumer adoption. And just like consumer awareness of FinTech like if you ask most people that like aren't FinTech nerds like us before, like how many of them unheard of chime, probably bear view. And then they went from like, what like 3 million to like 14 niche million users in the span of a year, year and a half. That's tremendous growth. And like more people now know it, they exist or even like Robin Hood, Coinbase, etc, and the growth of those companies. But then you even think back to like, the global financial crisis in 2008. Like, that was the impetus for so many companies start, like, if you look at interviews of like, John Stein from Betterment, like, that is why he started Betterment was like, basically, in response to the global financial crisis. And so many of these companies were like, We need to take back what is happening with the banks, and also this kind of unbundling of the financial stack. It's interesting, now we're seeing kind of like a re bundling. But at that time, it was like, let's build something that we can actually have a better customer experience and build it for the customer. Because it was such a missed like, this, like loss of trust between the customer and consumer. And the banks at that time after that did a crisis.

Nik  16:02

Yeah, it's super interesting, when you read accounts of the financial crisis, and people talking about how difficult was to recruit at these, like prestige banks afterwards, if you're a smart Ivy League accomplished, you know, could walk and chew gum at the same time, you know, graduate, you could get a job at a bulge bracket bank, and you know, these investment banks were really kind of the premier, like status, occupation, and then all of a sudden that gravitated to like the fang companies and the tech companies of the world. We're making the world a better place, you know, in quotes. But that changed a lot. And I totally agree with you. I mean, the other answer I had in mind for this question was COVID, specifically, as a big macro driver. You know, you nobody knew what a QR code was three years ago. And now, I think we all hope restaurants are gonna bring back paper menus, because we're sick of using them or nobody put a card into a digital wallet before but then all of a sudden, you don't want to touch the point of sale system. And so now everybody's loading up Apple Pay and Google Pay. And I definitely feel like there's kind of a big paradigm shift. Like even like, so many news stories over the past couple years have kind of been FinTech adjacent, like the Gamestop mania, and all these meme stocks, you know, that were facilitated by the Robin Hood's of the world?

Jillian  17:11

Absolutely. I mean, I did teach my nine year old grandfather how to deposit a check on his phone during COVID. I don't think he ever thought he was going to do that. For a second,

Nik  17:20

I thought you're gonna say I had to teach my 90 year old grandfather how to trade options. And I was like, why? I mean, you know, YOLO, honestly,

Jillian  17:30

honestly, yeah, like the money sign.

Nik  17:35

Okay, question number two. What do you think the biggest lifestyle change? We'll see in our lifetime? Is? I'll take a jump on this one, since I think it's only fair not to make the answer first, every time. One of the biggest lifestyle changes, I think we're gonna see is is just kind of the endpoint for globalization. Like, especially since the this is as far out of my domain expertise as you go. So we'll see how many people call me out for being like, very out of pocket on this one. But like, since the collapse of the Soviet Union, you had like a much more interconnected world. And you had this kind of growth of the Chinese economy too. And a lot of manufacturing moved from centers like the US and Europe offshore to low cost areas, and you didn't really have like labor capital, moving across borders as much. But now all of a sudden, especially like with COVID, and as an accelerant, you have more and more people working remotely, like even in larger companies like in a sustainable way, like not on a contract basis. And Bain published like 10 years ago, this report called like a world awash in capital about how capital is moving really seamlessly to investment opportunities across borders, and it feels like something where you can't put the toothpaste back in the tube. Once globalization started, it's gonna be really hard to turn that off. And it's gonna be kind of a good test with like, Russia and China now, D dollar rising like whether you get trade bloc's, but it feels like capital, labor or investment should kind of chase the maximum points of return. And borders don't really matter for that. And so I feel like we're likely to see a much more globalized world, you know, kind of regardless of like little hiccups and like geopolitical events over the next 50 years, we're really you're working with an international team, and you're also competing against international competitors, regardless what industry you're in. And you have a supply chain that's diversified between like three different, like countries, like low cost centers, and that's just going to change like, the composition of what jobs are available and where and, you know, maybe it's the case that the best lawyers in the world all you know, are educated like Buenos Aires, Argentina, and so they become like the lawyers for like international corporations rather than like the Harvard Law graduates of the world. The interesting to say,

Jillian  19:45

I completely agree in terms of the long term moving there. I think, maybe this is like I jaded side a little bit, but like, there are a lot of hiccups along the road, especially due to politics that we're seeing kind of like across the world, not just the US, but like all around the world that are kind of trying to be like, very anti globalization right now. And so I think it's interesting to see how that tension plays out in the short term. I think long term, it's really hard to kind of fight that. And because of a lot of the a lot of what you said, but I do think it's interesting to see how that continues to play out. This kind of like back and forth tension. But I do agree with you in terms of like the long term, that's absolutely where we're moving.

Nik  20:29

Yeah, no, I think that's totally right. Like you, you have the pendulum swing, and then it needs to swing back a little bit. There's always a reaction. And I feel like there's a lot of political issues where that's the case where you have like, forward movement, but then you have the reaction, that forward movement, and you think it was Obama who is saying at the end of his term, he's like, you know, what, sometimes things Zig is sometimes things and you have to realize that like the trend lines go in the right place, even if you have setbacks in the way they're

Jillian  20:52

no, absolutely. I think kind of, maybe my first point is somewhat similar to yours, because I'm thinking about a little bit us focus, but I think there's gonna be a really big shift in the like structure of how we think of employment. And I don't actually think of this just because of COVID. And like remote work, but I think so much of our lives are tied to our employer, especially around our finances, like in terms of, obviously, how we get paid, but like 401k, or health care, and everything like that. And that's not necessarily the most sustainable. And then when we think about like, I mean, this is a problem that, like so many people have been talking about, but like to get loans, you basically need to be a typical salaried worker, because it is so much harder for people that don't have that normal structure job, when like, we are increasingly seeing people have alternative income. And even if they have a traditional job, they might be making a lot more money elsewhere, or having two jobs. I think there was like some employer recently that I think it was a big thing on LinkedIn, where like, they fired two employees, because they were having two jobs. And like he didn't know for months that he was they were having two jobs like,

Nik  22:06

it's like says like a little bit more about you as an employer. It's like, are you really getting everything?

Jillian  22:10

Exactly? Like maybe they were doing a good enough job to do jobs? I don't know. And so I think that we're probably going to see some sort of a shift in terms of really like how, and if it's just like the benefits, but how a how we structure employment in the US and what that looks like. And everyone exactly know what that will look like, whether it's like we move away from the typical w two, or that format, but also how we structure a lot of what's tied to it and how we structure all of the like, financial benefits that's tied to it as well, because I think that's just like so prohibitive towards most people, and how we're moving in the world. And so I think that that will be really interesting to see how that continues to play out over time.

Nik  22:52

Yeah, I totally agree. I mean, to to kind of like quick fire ideas that that makes me think about your comment is one, the emergence of Dows and web three over the last year, you know, there's a lot of hype, this base grew too quickly, it consolidated again, and we'll see kind of what the long term viability of like dals looks like. But it's kind of the first attempt to re architect like the, like, corporate Corporation structure that we've had new assets like persistent for, you know, hundreds of years. And it's interesting, it's like, do you have this third path from WTS, or 10 eyes? Do you have kind of a spectrum of options available to you, where instead of being a salaried worker, for one company, you are a participant in four days, and you work on four different products, and the amount that you get paid is like relative to your input, and you just kind of like move seamlessly between them. And the other thought I had was, when you talk to people who come to the US, especially from Western Europe, or like Nordic countries, they're always shocked, like you said, by kind of how much of your life outside of work is immediately dependent on like, Where specifically you're working, like not even the work you're doing, but like the company that you're tied to. And there's this quote, you know, a developed country is not one where everybody has a car, but it's one where rich people ride public transit, I feel like that kind of applies here to where the shift in labor classification might mean that hopefully, you get kind of better social services and a better social safety net. And so stuff like having like your, you know, healthcare tied to like we're working specifically isn't as much of like the model that we have going forward.

Jillian  24:24

Yeah. I mean, I think it's crazy that like you change jobs, and like you might have to entirely uproot, like what doctor you're seeing or might not be able to get like a specific procedure because of that, that like doesn't, that shouldn't make sense. So that's wild. But maybe I'll continue because I think maybe like next one is sort of tied to the healthcare system. I think one area and fintech that I've been like wanting to invest in forever is at the intersection of healthcare and in FinTech. And part of that's because like, I shouldn't shock everyone that like our healthcare system is fully broken, and I think like will continue to just get worse and implode upon itself, and so at some point in our life, I kind of hope it does, mainly so that it can hopefully be rebuilt. And actually, in a format that works is I think, one of the challenges as much as I continue to like, look at a lot of investments and really want to make an investment of space, I think that a lot of them are probably more so like, band aids. Yeah. And that, we probably just need to actually fix the structure because none of the incentives work.

Nik  25:31

Yeah. Tyler Durden Fight Club approach, just blow up the healthcare. Start from scratch. Exactly.

Jillian  25:36

And so I think that that is probably one of the things that I look at quite a bit because like, both in terms of like how people live their lives, whether it's a one of those spectrum, like some people are uninsured, and or people don't want to be insured, because like, they can't afford it, or people just like, then don't go to the doctor. And then it makes themselves worse. And so then when they have a catastrophic issue that like impacts our healthcare system, even worse, but then just like the impacting costs of our healthcare system, like compounding over and over, is, is insane to me. And it's both like internally within, like, between payers and like how I'm not gonna go into like, how billing is done and things like that. But also, just in terms of like, how consumers operate. And so I think that like, hopefully, I'm not sure it looks like another just like, new presidential health care plan fixes up other than, like, we actually need to do something to fix the entire structure of it. It's interesting,

Nik  26:34

you know, you being a FinTech investor and wanting to look at the intersection of healthcare and fintech, because like just from that description alone, you feel like you can see the parallels there. There's a lot of legacy architecture and regulation that creates a certain system in the way it's set up. And so even if you take a step back and say, Oh, this is actually the Pareto optimal way. To solve this, there's a lot of path dependency for how the system is now where you're going to kind of make incremental improvements within the bounds that you have. And like, it would probably be better to be able to just start over from scratch. But easier said than done. When you have a very strong vested interest from companies have poured a lot of money into lobbying.

Jillian  27:07

Exactly. Yeah, too many people get paid way too much for this to ever happen. So it's a little bit of a pipe dream for me. But we'll go can wish not me that's exactly.

Nik  27:21

Alright, well, I want to make sure that we're staying on top of our time here. What one other one? Oh, man, this is like come given the most basic answers. So this is where you can start tuning out if you're listening in. But another kind of trend that I think is gonna change our style and quality of life is more mass adoption of different like point solutions and AI. You're starting to see

Jillian  27:44

crbc Yeah, exactly. Yeah, as the new hot topic.

Nik  27:47

I'm investing at the intersection of AI crypto. All the buzzwords. Yeah, exactly. please invest my fun to not a general solicitation. But, you know, alright, so like, there's all this hype around these, like consumerize AI products like GPT, three and Dolly and stable diffusion. Now that like, I don't know, if there are like proven commercial use cases yet. So it's like really cool to play around with these tools. But, you know, there's a couple of interesting companies like Jasper that's like building like a marketing specific engine on top of GPD. Three, but not, it seems like early days. And I don't know, kind of how investable a category it is yet because a lot of the market hasn't been proven out a lot of kind of scale, like enterprise use cases are not there yet, are still very early. But eventually, you're starting to kind of see that what a lot of what's considered to be creative work or knowledge work is actually pattern recognition, like it did to kind of an extreme point where even writing a good book, or making an evocative piece of art, is actually kind of just pattern recognition, where if you look at enough, really, you know, vontade artists, you too, can make a painting that kind of looks like it should be, you know, high art. And then for whatever the you know, goal is of art or writing a book or doing anything creative. You can you know, pass off that product and monetize it and do it and automatically do it like this massive amount of scale, within seconds, rather than actually have like a human creative process. And so it feels like there's gonna be a big labor dislocation from that. And all of a sudden, you have, you know, the lawyers of the world who are not as necessary in bulk to be able to put together you know, all the underlying documents for like a large m&a deal or like a take private or, you know, an LBO. And so what the world looks like after that is really interesting. You know, what new jobs and like sectors and jobs crop up after that, and like, is that dislocation, you know, really disruptive to like a huge swath of the population who all of a sudden find that like their jobs are replaced by like aI they can do like or work like more efficiently than they can. War is like gradual and like do you have retraining programs? I think it's it's kind of it's gonna be an interesting question. See that play out?

Jillian  30:09

No, I absolutely agree. And I think that I mean, you see it across the board with, obviously AI, but then automation in general, like I remember even I interned my freshman or sophomore year in college on investor sales and trading. And like, there was like nobody on the equity floor, it was like three people or something like that. And because most of it was automated, and they just didn't need to do anything, like they didn't need to pick up the phones really, like everything was on IV, like Bloomberg chat, like, that's all they need to do. And like, they would talk about that. And I remember there was one guy on there who started his career, like on the floor of the New York Stock Exchange, as like a ticket runner. And like, he would talk about how like how much it had changed and how crazy it was for him to see like how basically, his job had been automated away. And to see that now happening in more and more spaces, where to your point, like, you think like a human is fully necessary, and you kind of need that like mental capacity. It's kind of like, it's it's very strange to be like, oh, yeah, no, like, we're actually not that necessary, like reading a book now. Like, have ai do that as well.

Nik  31:22

Yeah. What does it mean, when all of a sudden society progresses, like, in spite of humans, just not needed to like move the wheel forward anymore, it's probably a good time to come out and just admit that my newsletter and my tweets are all written by GPT. Three. I've been on vacation for the last two years. All right. And so final topic. This is actually the question I'm most excited about. I think it's a super interesting one. And I'm gonna let you answer first. Have we experienced the defining moment of the decade? If so, what is it? If not why?

Jillian  31:57

So it's interesting, because like, obviously, we're very early in the decade, but a lot. That's gonna say a lot of shit. I think I was told. So apologies if I'm not a lot has happened already. In this decade. I was asked this question, actually, like, probably a year ago. And at that point, I said, Yes. Now?

Nik  32:23

I don't think so. And was that COVID? A year ago?

Jillian  32:26

Yes. Now? I don't think so. However, I would probably say that, like, the catalyst for whatever is going to be the defining moment has already begun, and has already been said, meaning like, could that catalyst be like Russia? Is War On Ukraine, starting a much broader war? Potentially? Could that be us going into a much bigger financial crisis and recession? And like, Yes, I think there's a number could be like a much bigger political crisis that we have, potentially. And so I think there's a number of things that like, have already you're seeing like the sparks kind of starting, that I think could be a lot bigger. But I don't think that we've actually seen the climax of it quite yet. And I think that's where I kind of stand on that.

Nik  33:22

I like that I would have totally said, either COVID, or the war in Ukraine is the defining, like, touch point, like this decade? And when you said, No, I was like, okay, maybe I should up my game in this answer a little bit, like Think harder. And I was trying to think back of, you know, think back on what other defining moments and other decades have been, and you can kind of see, you know, in the in odd Suez, like the global financial crisis really feels like it stands out more than anything else, as an example. And so it feels like our understanding of the world order, and like the Pax Americana that we've had, since, you know, most people like the millennial generation have grown up, ended and abruptly shifted with the Russia Ukraine war. And so the outputs of that, to me feel like a very compelling answer for a defining moment of the decade. But if I had to align with you and say, No, there's something that's gonna be even more defining. In my mind, this is like, I want another one of my basic thought boy answers, but we've watched China grow their economy and grow their influence on the world stage over the last 30 or 40 years, and a lot of people refer to it rightfully so as a Chinese miracle. Because if you look at like the rates of extreme poverty, like they've pulled an amazing amount of people out of poverty that if you look at like the skyline of like Shenzhen or like, Shanghai, like over a 30 year period, like it's just crazy how fast it's grown. And you know, the economy has grown by like low double digits, high single digit percentages every year, and now you're starting to see that slowed down a little bit. I'm sure that a lot of it is due to like supply chain issues and COVID. But like, there's probably also some kind of secular slowdown in that growth as well. And so it feels like this decade is kind of could be a transition point between growing your influence and establishing, establishing yourself in the world stage and starting to exert your influence. And what exactly that looks like, I think is could be a defining moment for us politically, like, do we continue to live in like a unipolar world or a multipolar world? You know, do we have kind of another cold? Where where like, countries independently decide who they want to align with and whose model they accept? You know, a lot of the, like soft power influence like the Belt and Road Initiative, does that become hard power and kind of a more, a more kind of like overzealous foreign policy that feels like, it'll have ramifications for like, where we sit in the US and like, our position in the world, and like how we are perceived. And so that, to me is like, it's another like, raise and ensure that everybody's talking about but it feels relevant.

Jillian  35:54

No, I like that answer a lot. And I think my only answer, oh, my only rationale for why like Russia, Ukraine, currently isn't is. And again, this a little bit US centric, is because I think a lot of Americans have like a very short attention span. And so like, for awhile, it was like the worst thing ever. And then they kind of forgot about it for a little bit. And I think like, it's come back a little bit, but like until it is, unfortunately, like impacting our day to day a little bit more. People aren't going to think it's like the end of the world. And so I think that's where it's like it needs to progress, unfortunately, out outside Ukraine a little bit more. For it to, at least from the US perspective, be the defining moment. But I do think that Russia invading another country is a huge, huge, like moment in the world. I do think though, maybe it's also more so from my perspective that I do think it can easily lead to more and more of an expansion of of the war globally. And then also, like, there's the risk of like China and Taiwan and things like that as well. That don't seem as far off anymore in

Nik  37:11

this world. So yeah, exactly. Like now, it's like what we thought was unthinkable is no longer unthinkable. Exactly. If you read like early stories of World War One, World War Two, you have all these, like populations that didn't want to go to war. And it was just like, the inevitability of all these, like international agreements that kind of dragged you in there. And I feel like now steps are being taken to avoid that. But to your point, it's kind of hard to tell what steps will escalate things and how, like, what looks like to be to country conflict, spiral and have broader, like more severe international implications? Exactly. Definitely trying to place a premium on good leadership. Yes. Okay, now that we've covered all the easy topics. And I'm sure when this gets published, they'll have million VCs who become experts on the war on Russia, Ukraine. That's my word wrong. But we can we can take the blowback when it comes. I love the idea that you had for a FinTech rapid fire, just power through some questions like popcorn like top of your mind, right. And so let's start. Let's start with a question that I really have no good answer for but favorite FinTech

Jillian  38:26

ad. Recently, maybe this is just because it's top of mind. Cash App has a ad with Kendrick Lamar, Ray Dalio and some comedian his name I do not know I apologize. And it's basically like Kendrick Lamar is like the translator for Financial Services and Financial Literacy between the two of them because like they can't understand each other and it's actually very funny.

Nik  38:53

Yeah, that was wild, who saw Kendrick and Ray Dalio getting into a room together. So I want that podcast that's a podcast you're listening to Well, we talked about this for a second but I was I thought it was really interesting at the Super Bowl a couple years ago and so if I ran an ad about who should not apply for so if i car and I heard some reports afterwards I was like actually increase like their average like, applicant quality but I was just like, wow, like IT tech is like such a like positive and like, like you kind of paper over a lot of like, the underlying, like difficulties like products. They're just like, leaning into it. I was like, That was that was an interesting way. Roleplay Yeah, I guess. All right. Favorite FinTech or finance related

Jillian  39:41

book is probably the lamest answer possible, but like I love Michael Lewis. So The Big Short, like that was the book that like made me want to get into financial services officially. So I'll take that.

Nik  39:54

That's awesome. I want to trade the world. Actually, in the same vein, I would say My favorite book about that terrifying that I've ever read is the ascent of money by now for and and it's like very, like I feel like Michael Lewis is such an evocative writer and Ferguson also has like a great way of just like taking what should just be a really boring topic, like the history of like money movement, and like Western Europe developing the monetary systems like actually make like super engaging. More recently, I am a big, this is no secret to anybody who sees my twitter but I'm a big fan of Sofia Goldberg is the founder of word answer. And I picked up her book Field Guide to global payment systems. And yeah, it was really just easy to understand. And also kind of like, maybe appreciate, like how much domain expertise you build up in FinTech like, oh, yeah, like these are actually like, not accomplices, like everybody, like comes out of the womb, knowing

Jillian  40:46

Oh, yeah, and actually making it where people can understand like, that's like the payment stack is very impressive. And that making it interesting as well.

Nik  40:55

Yeah, totally agreed. It's a Christmas present, I'm getting for all my family. Getting invited back to Christmas. All right, FinTech app or product that you use the most.

Jillian  41:09

I would say. I don't want to say lame, but sorry. Marcus and betterman are probably the two I like automated to take to my paycheck every two weeks. So I'd say probably those two.

Nik  41:23

They love that. I mean Fintech is FinTech, even if you're getting it from Goldman Sachs. I mean, my answer is equally lame. It's like, it's definitely Venmo I think just you know, real time instant peer peer payments with my entire network, it just made my life so much easier. I have an issue actually, where I created a merchant account for this week in FinTech because we had to accept like Venmo payments at events way through. And they're like, threw me into like a, like a bottomless rabbit hole of KYC for my personal Venmo account, cuz like they're both linked to like the same, like, Chase Bank profile, even though they're two separate accounts. And so like, there was like, a little period where I went without Venmo. And I was like, this is awful.

Jillian  42:05

I had to, like, ask people to pay back your friends.

Nik  42:09

That was like, honestly, like, you think it'd be awful because like, people can't pay me back. But it was like, even worse for me. Like when somebody was like, Yo, can you hit me up for dinner? And I'd be like, can I write you a check? Or can I send you a zombie? Like, what kind of sketchy stuff? Have you been doing that? You know? I just realized how much I relied on it. All right, number one item on your FinTech wish list. I think

Jillian  42:31

it would be in like, there are some companies kind of trying to do this. But it'd be something that like, told me how to optimize my finance better, but at the point of action, and like, I hate no offense to anybody, but like, I hate PFM. Like, I don't want to see how poorly I'm spending my money. Like I know, I am not good at it. But like, at the point of me buying something, tell me what I'm supposed to use? Is it better for me to use? Like, which credit card? Is it better for me to use a affirm? Or is it better me to do X, Y, and Z? At the point of me getting paid when I move money into betterman, Marcus or anything else like which one is best for me to do and optimize? Or like doing it at that point of actual action, I think is the most impactful versus, like, just kind of giving me advice later on. I just don't

Nik  43:20

$200 at restaurants last week. Yeah. Like I know,

Jillian  43:23

all my money goes to food. That's not helpful. I'm not going to change that.

Nik  43:27

Okay, but who's released here? I actually have the exact same answer as you. I would love just an app that tells me where all my money is at any one time all my money like all three or $49. But like we're all my money, is it any one time and then like has a little flag that can tell me if something's not being used ultimately, like, you've got this much sitting in a digital wallet. Like you should be like, you know, investing in like, you know, T bills or something like while it sits there. Yeah, exactly. Okay, most underrated FinTech founder. Oh, God.

Jillian  44:01

I don't want to do anyone that I've I've invested into

Nik  44:04

Silla portfolio. So I will ignore that.

Jillian  44:06

This might be a little bit top of mind because I saw the person today. But I'd say two of my favorite fin tech founders, just because they're like two of the nicest people are Tommy Nichols and or Sigrun. They're just like, really great humans. And Allah is a great company.

Nik  44:28

I totally agree. It's been. It's been awesome. Like watching. We like beta, that company pedal. And I was like, Oh, this is like an interesting tool. And it's just grown so much. And I feel like they are so intentional about how they grow and structure the company and what they do and the kind of environment that they're trying to create their workforce and I'm a huge admirer of theirs. Absolutely. Oh man, this is like also top of mind, but not a company that I've invested in and I just want to shout her out but Daraja clued in her co founder of her right foot They're kind of in the same mold. Like, I feel like they're intentionally working on a problem that matters to a lot of people debt repayment, and doing it in a thoughtful way with a good product and kind of the right mentality. You know, do to reach out to me one point about making introductions to prospective investors to diversify, you know, her own cap table, and I feel like caring about that, like, not just like, that you're getting money in but like, where your money is coming from is like a level of intentionality that like I kind of hope to carry and like really respect,

Jillian  45:31

absolutely, Stephanie's her, Patrick, or I'm also really paid a lot of attention to that. And that's something I respect so much.

Nik  45:38

Yeah, I totally agree. So shout out to all of you. Okay, we're coming towards the end here. But who would be the mayor of FinTech town?

Jillian  45:50

I think this probably changes. But right now, it's probably the founders of stripe. I'd say they're just like, consistently the top dogs in FinTech. And I've really changed. FinTech probably the most in general. So shout out to Patrick.

Nik  46:07

Yeah. And they'd like to it was such a positive attitude to I feel like they're very, like, positive. So we're not going to get involved in petty infighting, we're not going to compete. We're going to layer climate into all of our products, which we don't have to do we have, you know, an oil Geyser of payments, revenue, and yet we're going to be intentional about what we see as bigger social issues. I love that answer. Mine is much more shallow. It's based on like, Twitter activity following alone, but I feel like it's hard to make a case against shield mo note.

Jillian  46:40

You know, I had a feeling you were gonna say him, for I

Nik  46:42

know, I'm too much of a fanboy. But I just feel like, he also I don't know. He He's older than I am. I'm 33. And he has the intellectual curiosity and energy of somebody who just learned about what FinTech was yesterday. And it's like really hard to retain that over time. Like you get kind of calcified. You get set in your ways you like develop beliefs, and it's something that I admire a lot, but like I see it, like, kind of go into like, how many people he wants to meet how he engages all of them and like to me, that's like, just going out and shaking hands and kissing babies and being being mayoral. Absolutely. Okay, we have three minutes. So we have three questions. So let's close the rapid fire. If FinTech were a movie, who would the bad guy be?

Jillian  47:26

I would say, you could argue like the regulator's for when they stop things from being able to happen. You could argue the bank sometimes. And also, like I think lenders are kind of oftentimes don't have really great intentions with consumers. So those are like probably my three that I'd say. Cuz you can always argue that they could be the bad guys.

Nik  47:50

Yeah, I feel like it's a play to another question we have, but I feel like there are a lot of non incentive aligned with customer products that exists in the traditional financial world. And crypto definitely and and fintech. And so being able to like understand kind of weed out those customer adverse products, I think would be like the thesis of like the FinTech movement. If you want FinTech to be around, you need to weed the bad guys out. Most transformative slash impactful FinTech

Jillian  48:21

I'd probably have to go plaid or stripe.

Nik  48:25

Totally, for reasons already discussed, like they just facilitated this whole ecosystem. This is like a little bit like outside of like my, like tight aperture, but I'd say UPI in India. Now it takes in Brazil a little bit, but like it's crazy, like how much innovation and building has been enabled, like government backed initiative for payments rails, like is the government of India, the number one FinTech innovator the last decade, you know, probably not, but like, it's just crazy how much has been built off of that.

Jillian  48:54

And pace. It was another one I was gonna say, Well,

Nik  48:57

yes, absolutely. I mean, like pick up like how big like the, like Pan African remittances ecosystem is now in terms of companies and like different quarters, and it's all from a pace. It's insane. Okay, last question. Why don't get down here? Is all FinTech net good for the world. No.

Jillian  49:18

No, I think that I think a lot of companies even when they want to necessarily do good, don't necessarily always have the best intention for the consumer. And I think it's very given that we are dealing with people's money, I think it's very easy. Whether or not there's intention behind it to get people in trouble because you're dealing with money. Other people don't know how to manage their own money. And so you can easily get people in trouble in that way. But then also, oftentimes, business models are not necessarily aligned with consumers as well. And so that can be a challenge.

Nik  49:52

Totally. I agree. Maybe a weird question or way to answer to end on but you know, finance is a tool the end of the day and the tool can be used for good and it can be used for not good I think it's our role as stewards of FinTech to make sure that we're moving more resources towards the good side. So, thank you for coming on to the show today and talking a little bit more about how you're making FinTech better.

Jillian  50:11

Absolutely. This has been fun. Cool. All right. Thank you are You didn't hit record