PayPal’s Embedded Finance Vision: Michelle Gill reveals how cash flow lending is reshaping SMB access to capital

As General Manager of PayPal’s Small Business and Financial Services Group, Michelle Gill is responsible for bringing together the products and services that help small business owners run and grow their business. She is my guest for this episode of the Tearsheet Podcast.

Michelle brings deep financial expertise and experience building platforms and tools that help customers manage their finances to her role on PayPal’s Senior Leadership Team. Michelle was previously Senior Vice President of Intuit’s business money management, payment, and banking service, QuickBooks Money Platform. Prior to Intuit, Michelle successfully integrated and expanded SoFi’s lending business as General Manager and Executive Vice President of Consumer Lending and Capital Markets.

Drawing on her early career experience as a Managing Director and Partner at Goldman Sachs, Michelle also served as SoFi’s Chief Financial Officer before moving into the product leadership role. Before that, Michelle spent a decade leading the U.S. Assets business for global investment firm Sixth Street Partners.

Given her career and experiences, Michelle brings a broad view of fintech innovation. She focuses on user-centered solutions. At PayPal, she leads efforts to help entrepreneurs navigate the complicated web of financial tools they often depend on.

“The preponderance of [small businesses] use greater than 15 tools to run their business,” she shares. “What they got into business for is the passion… and yet they end up spending more time on things that are not what they love.”

Our conversation explores how PayPal is actively trying to reduce that complexity. It does so not by offering more tools, but by making the ones they already use work better together. Gill outlines the strategy behind PayPal’s cash flow-based lending model and how it fits within their open ecosystem, whether it’s digital lending, embedded finance, or leveraging open banking.

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How PayPal for Small Business solutions addresses complexity

For many small business owners, managing finances often means juggling over a dozen platforms. PayPal is stepping into this chaos with the goal of integration.  “It’s not the adoption of the new tool in and of itself that’s the problem. It’s how it feeds back into your broader ecosystem,” says Gill. PayPal’s strategy focuses on streamlining tools through a single integration. It aims to reduce friction and give entrepreneurs more time to focus on their craft.

How PayPal cash flow lending works

PayPal’s approach to cash flow-based lending matches repayments with earnings. It is unlike traditional fixed-schedule lending. “Repayment is predicated on the receipt of those earnings,” says Gill. She describes the flexibility of the PayPal Working Capital product. This flexibility makes the loan more manageable for merchants with fluctuating revenue.

But, until recently, merchants couldn’t access more funds until fully repaid the loan. That’s changing. “We are changing our product to allow for the ability to redraw,” she notes. She signals towards an update that will help entrepreneurs recycle capital more efficiently.

Leveraging Open Banking for better lending models

Previously, PayPal could only lend based on what it processed. But open banking now enables them to assess a holistic view of merchant cash flow. “We now can have visibility into the entire merchant account, both on and off PayPal,” says Gill. This broader perspective supports more accurate underwriting. It offers larger loan sizes without expanding the credit risk.

PayPal is embedding finance into merchant workflows

PayPal isn’t just offering loans—they’re embedding them into the workflows merchants already use. Through the PayPal dashboard, users are notified of pre-approved loan amounts as they manage daily tasks. These are like refunds and chargebacks. “We are planning to add the amount that merchants have been pre-approved for, so they know going in,” Gill shares. PayPal is also collaborating with vertical SaaS providers, as well as with marketplaces, to bring financing directly into partner platforms.

Growing with merchants in the Open PayPal ecosystem

Through its open ecosystem, PayPal aims to grow alongside its customers. “We do things from point of sale to lending to online payments for e-commerce… we’ve tried to grow with our customers as they’ve grown,” says Gill. That includes helping businesses navigate newer challenges, like Generative AI and complex commerce models. “We do that through education, tools, and end-to-end services,” she adds.

The Big Ideas

  1. Small Businesses Face Tool Overload. “The preponderance of them use more than 15 tools to run their business.” This overload creates inefficiencies—PayPal’s integrated platform is intended to reduce that friction.
  2. Cash Flow Lending Matches Business Realities. “Repayment is predicated on the receipt of those earnings.” This model reflects how small businesses operate, especially in unpredictable markets.
  3. Access to Capital Expands with Open Banking. “We now have visibility into the entire merchant account… not only borrow against your PayPal receivables, but also your off-US receivables.” This broader access supports more accurate and inclusive lending.
  4. Embedded Finance Increases Accessibility. “Merchants who use PayPal come into their dashboard generally at least once a week… We let them know they have access to capital.” In-app lending notifications simplify the financing journey.
  5. Loyalty Grows with Product Adoption. “If you borrow once from us, you tend to borrow five or six times.” This repeated usage signals that the lending tools are resonating with merchants.

Read the transcript (for TS Pro subscribers)

A unique perspective on financial services

I’ve always loved serving the customer, as you mentioned, be it at the enterprise level, the consumer level and the small business. When you think about the number of companies that serve enterprises, it’s pretty meaningful. Similarly, the number of companies who serve consumers, it’s also pretty meaningful.

When you look at the number of companies that seek to serve small businesses, it’s actually a smaller number. And the complexion of small business is much more complicated in that they vary dramatically. And so far as the types of businesses that they are, both online and in store, both, you know, they have a pretty global reach and footprint their sophistication level varies all the way down from solopreneur up to small and medium sized small businesses.

It’s a really complex group of businesses to serve with single point solutions. And so what you find is there is a much smaller set of companies that serve them. And so the thing that I’ve loved about the ability to serve them is really getting to know them a lot better, understanding the complex needs that they have.

The preponderance of them use greater than 15 tools to run their business, and yet, the last thing that they have time for is managing that complexity. What they really got into business for is the passion that drives the particular thing that they built or are selling.

They end up spending more of their time on things that are not what they are core to them or what they love, and so our goal is really to reduce that complexity and really try to allow them to have that time back to pursue their passion.

Reducing complexity for small businesses

I think the complexity comes from, as you expand your business, or you think about doing new and different things, you often need to adopt an incremental tool through which to do that.

Whether PayPal offers that directly or through partners, the notion of being able to ingest it in a singular integration and not have to integrate with the new solution make it work with your reporting, having everything sync, right?

It’s not the adoption of the new tool in and unto itself, that’s the problem. It’s how does that feed back into your broader ecosystem, from a small business perspective, and making sure it all ties together.

That’s the place where it would be nice to have a single place to actually undertake many of these tasks, rather than having them distributed through a very broad ecosystem that doesn’t always necessarily work seamlessly together.

The challenge of scaling FinTech solutions

That’s right. As companies develop, they become incredibly specialized in one particular thing. And when I look at what I have loved about the portfolio that we have at PayPal is, we do things from point of sale, which is an in store solution, to lending, to online payments for E commerce.

We allow merchants to transact in over 200 currencies. And so the ability to migrate from geography to geography or online to in store, or complexity of the level of payments and how you’d like to accept payments, we’ve really tried to grow with our customers as they’ve grown.

Balancing growth with simplicity

At Investor Day, we talked about PayPal Open, which was bringing to bear all of our capabilities under one umbrella. One of the things I mentioned at our investor day was, you know, it’s one thing to come out with a brand. It’s another thing to come out with simplicity, and those two things are very different.

You can tell everyone, oh, everything is now housed under one umbrella, but as I described earlier, if that necessitates the merchant to have to actually do incredibly hard and challenging work to do the integration themselves, rather than having it all pre integrated on the back end and having just switches that you’re able to turn on and off as you’d like to actually utilize a particular part of a product.

In one instance, you’re asking the merchant to take on the complexity, and the second, you’re taking on the complexity. And so we’ve spent the last couple of years really taking on that complexity and ensuring that our products actually do work together under a single integration.

We came to market with that. We’ve now rolled that out in 200 countries. And we’re really excited about the ability for merchants around the globe to be able to adopt that single integration, which includes both getting the branded button, being able to accept credit card payments, being able to accept local, different types of payments, methods, locally in each geography, etc.

We’ve really tried to take all of the acquisitions that we undertook and all of the capabilities that we now have, and house them into one thing that makes it much easier for merchants to adopt.

The evolution of small business lending

Obviously, one of the things we’ve been tracking over the past few years, particularly with COVID, is like small business lending really changed dramatically, and has been doing so really over the past decade. And I’m kind of curious where you see the biggest gaps in the current market that PayPal is uniquely positioned to address.

A recent Goldman Sachs study came out and said that more than three quarters of small businesses are concerned about access to capital as they maintain or grow their businesses this year.

What we continue to see is the appetite for the simplicity of the product that we offer, and the way that that manifests itself to us is a very high net promoter score from the merchants who do take out that product. It is incredibly easy to use in that it is entirely a digitally native product.

The PayPal working capital product in particular, aligns incredibly well with the way in which a business earns. One of the concerns as a small business, particularly in a changing environment, and the current macro being amongst that, is, how do I know that predictability of the cash flow that I’m going to have coming in, such that I feel comfortable taking a loan on a fixed repayment schedule?

The reality is that businesses are cyclical, and there is a changing macro, and so you may be deciding to buy inventory to grow, and yet it may take you longer than you initially expected to sell out of that inventory. If that happens to be the case, then you’re on a fixed repayment schedule, as was the case with traditional lending, and now you’re in a situation where you have to repay the loan before you’re getting proceeds from the sale of that inventory.

The thing that we love about PayPal working capital, which our customers love as well, is it is the repayment is predicated on the receipt of those earnings and proceeds. Hence, the merchant can feel very comfortable when they take out a loan that they are not going to be in a situation where they’re forced to repay ahead of the receipt of proceeds.

Now, the downside of that structure, in current form is you could have paid down substantially faster than expected, and actually want to re up that inventory. And in today’s environment, which we are looking to change, we haven’t given you the ability to redraw on that loan ahead of the full repayment.

What ends up happening is, let’s just say that you have a small tail out there that you haven’t repaid. You’re in a position where you can’t redraw, and if you would like to recycle that capital and really put it back into inventory, you have to wait. And so we are changing our product to allow for the ability to redraw such that merchants can have the flexibility as repayments may come in faster than expected, to actually have access to that capital, to continue to double down on the growth of their business.

Product evolution and underwriting

It won’t be a difference in credit, right? Because realistically, it’s the same merchant that one is underwriting and you’re underrating again the ability to repay those proceeds. And so the underwriting box actually remains quite similar.

It’s really more of both a policy change as well as a technology change, a policy change. In the context of today, you cannot re borrow unless and until you’ve repaid. So you cannot have two PayPal working capital loans outstanding at the same time.

In the future, in order to allow this to happen, we would want to be able to have you have two PayPal working capital loans outstanding at the same time, which requires, again, like I said, both a technology change on our side as well as a policy change.

Advancements in underwriting technology

It used to be the case that we relied almost exclusively on PayPal data.

What I mean by that is, if you’re a merchant and you sell whatever your goods are that you sell and you receive X percent of your payments through PayPal, you could only borrow against that portion of your receivables, because that’s what you had visibility into.

Now, with the advent of open banking, we have visibility into the entire merchant account, both the receivables that they receive on PayPal as well as those that they receive off PayPal. And so we’ve recently introduced the ability to not only borrow against your paypal receivables, but also your off us receivables, because we now have the ability to have visibility into your entire business and the receivables, and the ability to collect against both of those.

That has been a very meaningful change. We’ve seen our customers that really have gotten to take advantage of this be very happy with that change.

The other change is, as I mentioned before, by consolidating all of the properties within PayPal, some of the receivables that were coming in at the physical point of sale, you couldn’t re borrow against, or you couldn’t borrow against, and now you have the ability to borrow against those as well.

What we’ve really done, again, with that single integration point is allowed all of that data to flow for both the PayPal receivables and then again, the ability to ingest that third party data and make credit decisions based on the holistic picture.

Embedding financial solutions into business workflows

The way in which we do it today is one way, and then we intend to actually expand on that pretty meaningfully.

The way in which we do it today is merchants who use PayPal come into their dashboard, generally, at least once a week, if not greater than that, and they review their outstanding receivables, whether they’ve had any disputes, refunds, chargebacks, etc.

As part of that, on that dashboard, we actually let them know that they could actually have access to capital. And we see a lot of that through the dashboard, both on the app and on the web.

We are planning to add to that, the amount that merchants have been pre approved for, so that they know going in. Here’s how much you’ve been pre approved for. And again, one of the biggest complaints has been loan size. But now, again, as I mentioned, with the advent of open banking and the ability to lend against a broader swath of receivables, there really should be the capability to achieve the loan size that merchants are looking for. So that’s one way.

Then you mentioned embedded finance. The other thing that we are working on with some of our larger partners is also embedding it into their experience, and making sure that as merchants log on to their experience, which may be something that is more persistent. You know, they also have access through that experience.

Lending is one of those things because of licensing is a little bit harder to white label. However, trying to make sure that it really fits into their experience, we’ve done a couple of tests with some partners where partners were looking for their merchants to upgrade the integration on the partner, and we’ve financed that integration, and really given a discount, actually on the amount charged to the merchant to borrow for that integration.

We’ve really enjoyed working with our partners to help them grow, and using lending as really an ability for them to help create the growth solutions that they want for both their merchants and themselves.

The changing landscape of small business finance

I think that when you look at small business lending, it really, despite the fact that everybody understands the need, I wouldn’t say there’s been a massive expansion of the amount of lending that is being done globally relative to the need in the market.

It is a very wide open space with a much bigger need than there is supply of capital. And I think the really interesting thing is, when we talk to investors who are interested in the asset side of this, there’s a lot of appetite for this asset.

I think people understand that it’s an incredibly interesting asset, particularly because it’s tied to cash flow. Investors really like cash flow based lending. It’s incredibly tangible. And so it feels as though there continues to be a dearth of supply of capital relative to the amount of lenders that are out there.

One of the things that’s been really interesting when we’ve talked to third party investors, is the reason they like someone like us lending relative to a third party is the access to data, a proprietary access to data that we have that allows us to do that lending responsibly, and allows us to do it in a way that doesn’t put merchants into a cycle of debt, that doesn’t actually hurt businesses, but instead helps them grow, is what they really like.

They like being part of that story. They like the history that we’ve had in the business, and they like the incredibly measured growth that we’ve had.

Interestingly, as we look at expanding, we’re not really meaningfully expanding the credit box. We’re expanding in the ways I just talked about, right, bringing in third party data that allows us to better underwrite the customer and be able to underwrite them for larger loans, serving segments of the market that we haven’t served historically, because we haven’t done loan sizes that are lower or higher.

I talked about that a little bit at our investor day. Is really a focus for this year of trying to ensure that we can really grow the base that we can provide capital to.

We are incredibly excited about all of these things, because we do think that businesses have and will continue to have a need for capital to facilitate growth, and the ability to do so at such an early stage in a company’s life is what can be a real difference maker in their ability to compete.

One of the things that we hear from our merchants all the time is, yeah, sure, everyone will lend to me once I’m successful and at large, it’s when I am starting out and I really need the capital. That’s when PayPal was there for me. And I will never forget that.

I think that’s something that really shows true. As I mentioned earlier, the Net Promoter Score and it again, it is much easier for a company like us, with the data that we have and the insights that we have into these small businesses, to be able to be there for them when they are smaller, and then to stay with them as they are growing, because we can uniquely meet their needs, because we understand their cash flow.

Creating a virtuous cycle

[Growth in the product has been almost exclusively organic. We really haven’t done much outside the ecosystem to inform and so we’ve started testing really trying to get to our merchants, not just through internal channels, but also external.

I 100% agree with you. I think what we see is, if you borrow ones from us, you tend to borrow five or six times, which is evidence of the fact that you like the product and that it is working for you.

I think the other thing that we see is, as you are borrowing, we do see meaningful growth in the businesses that do borrow, which is amazing. And then lastly, we also see that the more products you adopt, the greater your persistence and longevity is on the platform.

The things that we get excited about are the notion that the more PayPal receivables that you have, the greater amount that you can borrow. Obviously, the receivables that are off us are quote, unquote riskier to us in terms of the ability to collect against them, etc.

Yes, it 100% creates a virtual cycle of the more merchants do with us, the more like they grow, both for themselves and on us, and we really want to help facilitate that growth. That’s what we’re all about.

The future of small business financial services

So I think you’re one of a handful of people that sort of been at the epicenter of this convergence around serving small businesses. And I’m curious what your perspective is, looking ahead a few years, like, how do you envision the relationship between like, payment processors, banking services and lending platforms evolving for small businesses?

I think that small businesses will continue to face increasing complexity with the advent of agentic tools, agentic commerce, etc.

I think being able to be a place that can help them continue to navigate a changing landscape is really critical, and we do that through education. We do that through new tools. We do that through end to end services, and we try to take on the things that drive the greatest complexity, generally in their financial lives.

Because nobody is excited about doing their finances at the end of the month, but everyone is excited about seeing their bottom line grow. And so how do we take the stressful part of that out, and how do we bring the joyful part of that back and let small business owners spend the time doing the things that they really love doing, which is creating their product, speaking to their customers, growing their businesses in new ways.

And how can we be an agent for growth rather than that point of stress?

Venture Capital’s shift from consumer fintech to infrastructure ft. Ryan Falvey

Venture capital Ryan Falvey

In today’s financial landscape, innovation is more than just a buzzword—it’s a driving force separating industry leaders from those left behind. Finding, nurturing, and scaling the right technologies has become a specialized skill set all its own.

Joining us today is Ryan Falvey, Co-Founder and Managing Partner of Restive. Ryan has spent the last 15 years at the forefront of identifying and championing market-changing innovations in financial technology. His track record speaks for itself—since 2015, he’s invested in 40 early-stage fintech firms that have collectively grown to represent approximately $3 billion in aggregate equity value.

Before founding Restive, Ryan led the development of the Financial Solutions Lab, a groundbreaking partnership between JPMorgan Chase and the Financial Health Network. His experience also includes developing payment solutions with leading tech companies at Silicon Valley Bank and serving as Strategy Group Lead at Enclude Solutions, where he oversaw global strategy consulting for mobile-enabled financial products.

“We’re not investing in fintech apps — we’re investing in infrastructure,” Falvey explains early on. That distinction underscores a larger trend he sees in the market: a move away from flashy consumer-based apps toward foundational financial APIs. It also focuses on backend tooling and embedded finance capabilities.

Falvey’s insights aren’t theoretical — they’re rooted in his day-to-day decisions as an investor. At Restive, he’s helping startups through early product development. He emphasizes practical scalability and regulation-ready business models. “You don’t build a consumer business by launching an app anymore,” he says. “It’s not about the app — it’s about access, context, and integration.”

From fintech regulation to platform economics, Falvey shares grounded wisdom. He focuses on how successful startups are navigating today’s uncertain investment landscape. What’s emerging is a more nuanced strategy for funding — one that prioritizes durability over disruption.

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The shift from consumer apps to infrastructure

According to Falvey, the biggest shift in fintech is where the value is being created. “The last wave of fintech was all about building shiny apps for consumers,” he says. “Now, it’s about making the systems that power those apps smarter, more scalable, and more secure.”

He points to the importance of financial APIs. He focuses on other backend solutions that serve as the connective tissue of modern financial services. These are often invisible to consumers. But they are essential for delivering the kind of embedded finance experiences users now expect. “The infrastructure layer is where the real innovation is happening. That’s where we’re seeing the biggest opportunities for venture capital.”

Reframing embedded finance as context, not channel

Falvey is careful to clarify what embedded finance means in practice. “It’s not just about plugging in a payment widget,” he notes. “It’s about being in the right place at the right time, with the right financial product — whether that’s credit, payments, or insurance.”

For him, embedded finance is less about technology and more about use cases. When startups can identify the consumer-based need and deliver financial functionality at the moment of need, that’s when embedded finance makes sense. Otherwise, it risks being just another buzzword.

The new venture capital playbook

“Startups are now being built in a different economic climate,” Falvey says. Gone are the days of massive burn rates and growth-at-all-costs thinking. In their place: a greater emphasis on operational discipline, regulatory readiness, and long-term scalability.

He explains how venture capital firms like Restive Ventures are adapting. “We spend more time with teams on product development than ever before. It’s not about speed to launch — it’s about building something that works, that scales, and that fits into the regulatory environment.”

Navigating fintech regulation and compliance

Compliance isn’t just a checkbox — it’s a design constraint. Falvey emphasizes that startups must build with fintech regulation in mind from the outset. “If you’re in fintech, you are in a regulated business. You can’t build first and figure it out later.”

He sees a growing appetite for products that are “compliance-first,” and that build regulatory considerations directly into their infrastructure.

The Big Ideas

  1. Infrastructure Is the New Frontier. “We’re not investing in fintech apps — we’re investing in infrastructure.”
  2. Apps Are No Longer the Centerpiece. “You don’t build a consumer business by launching an app anymore.”
  3. Embedded Finance Depends on Context. “It’s about being in the right place at the right time, with the right financial product.”
  4. Venture Capital Is Recalibrating. “We spend more time with teams on product development than ever before.”
  5. Compliance Must Be Baked In. “If you’re in fintech, you are in a regulated business.”

Read the transcript (TS Pro susbscribers)

The evolution of fintech since 2021

Well, thanks for having me excited to be back. Maybe that’s a great way to start. I mean, that’s interesting, because we probably spoke at the absolute kind of high water mark of, you know, FinTech 2021, I was kind of the year. I remember, you know, you talked to other investors, and we’d like, man, we just should have done all the deals in the last like, shoot your fish in the barrel. Yeah. Any, any discrimination in selection was, was, was a, was a negative bias. And then, you know, things obviously changed really dramatically, starting in, starting kind of in 2022 and I think to a degree, continuing, kind of to the present day, really certainly been a shift in sentiment of fintech. More broadly. And then I think also, you know, kind of a shift in sentiment kind of increased a little bit away from tech too. So it definitely kind of feels more like kind of back to basics in what we’re investing in and how we’re working with the founders. But at the same time, I’ll say a lot of that. You know, we are investors in companies, and so the main thing we’re looking at is like, what’s the only performance of the companies? What are these businesses doing, and are they making money? And how much money are they making? And how fast is, how quickly are they growing? And what’s interesting and surprising is at the company level and at the portfolio level, it’s literally never been better. I mean, we already have companies that are growing much faster and making more money earlier in the life cycle than really ever in my investing career, going back into over a decade. Now,

Performance of recent investments

Yeah, do you mean honestly? I can tell you, I can tell you the date that things change, and it’s January 1, 2023 really? It’s really looking and I think it’s really the impact you had of a lot of these new kind of LLM models, AI driven tools, especially on the coding side, it’s just dramatically accelerated how quickly technical startups can develop product and iterate, try new things and kind of push, push their vision out in the world. And the faster you can move in a startup, the more things you can try, and the more, the more kind of shots on goal you have, and the more ways you can improve on a product once it starts working. And just to give you a snapshot, the investments we made since the beginning of 2023 now make more money into aggregate than everything we did in COVID combined. And there’s probably half the companies there, and the ones that are the ones that are the ones that are driving the revenue in that kind of COVID cohort are the most technical founders, like the strongest, you know, technology solution. And there we’re seeing a similar dynamic. There’s, they’re raising, you know, very little follow on capital. They’re running really lean teams, getting a profitability much earlier. And so it’s actually a really exciting time to be investing at the early stages, because we are, we are really seeing of COVID, the total phase shift in technology, and how these businesses are being built, and how big they can get.

Impact on exits

Yes, yeah. I mean, I think we’re already seeing, you know, it’s, yeah, I know when you’re going to air, air these this session, but, you know, it’s, it’s early April right now, and we’re seeing, you know, there’s a number of kind of FinTech companies that expect to go public here and in the next, you know, them kind of listed so far this year, yeah, the public fintechs have generally done, done relatively well over the last, you know, year and a half or so. So, I think there’s definitely a shift, kind of an appetite there in a late stage, and probably see more come. You know, the stuff that we’re investing in now. I mean this, many of these businesses are probably still five years away from from going public and you know you, we meet you, you tend to see mergers at this stage more and more frequent acquisitions. And I say that what we’ve seen on the acquisition front has been, has been pretty robust. But I think the best companies are probably not gonna be acquired. They’re gonna continue to try to grow. And I would, I would expect them to be, expect us to be seeing some, really significant businesses being built, kind of in this current era.

Thematic shifts in investment focus

I mean, we’re seeing a number of things. I mean, the big thing would be tech like, I can’t, like, you know, we’re investing in technology companies, okay? And that that is, and I think to a degree, you know, we, you know, we raise money ourselves, we explain to our investors, you know, we’re investing in technology companies who just happen to be in the financial services industry and and I think that that’s, that’s a real shift from 21 where, you know, people are like, Oh, we just needed digital. Stuff is going to take over, you know, so if it’s online, it’s going to be better than being offline. And you had just incredible growth of a lot of the businesses that existed and were doing which were strong, but it wasn’t like, hey, there’s a completely new technology here. And I think now we are seeing some truly new kind of technology innovations that are allowing founders to build entirely new, new approaches to financial services. And I’d say there’s kind of, there’s kind of, like six, kind of big categories where we’re seeing a lot of activity.

One is obviously generative, AI tools. The biggest impact there is actually probably within the startup, I’d say that, like, the best, best use case of AI is creating a company. Because, you know, if you have to create a bunch of stuff, you know, tools like, you know, chat, GPT and Claude and coding assistance like cursor, are incredibly helpful to create that stuff more quickly.

A lot of the crypto infrastructure that kind of got laid down over the last couple of cycles is now pretty useful, um, you know, there’s you there are there stuff out there that’s allowing for kind of agentic payments and ways of, kind of just automating kind of, you know, background, kind of purchase and inventory management systems that’s going to come directly out of, out of crypto. You have a company in a political Crossman that basically does that allows, you know, it was originally a lot of infrastructure for nfts, and is now being used to basically just kind of automate, you can automate payments, and, you know, just kind of set these kind of agentic payments to kind of run the background.

We’re seeing, I think the service industry, particularly around like consulting law firms, anyone who is making a lot of money by creating paper tax prep. I mean, those industries are under serious threat. And so we’re seeing startups there that are just, I growing at unbelievable rates, in large part because they’re just, they’re able to create advice layer. So, like in finance, about financial services, to say, like, you know that you have, you have services, and then you get a license from the government to do the finance part. And a lot of those services. You know, you’re you’re doing something that has an audience of one or an audience, maybe nobody. You’re just creating paperwork that sits on a shelf in case someone wants to see it in the future. I see you’re thinking about Iron Mountain. There’s a mountain just full of paperwork that somebody paper. Yeah, yeah. How much did all that paperwork has to get created? Like it was a lot. And if I can spin up it, like, you know, an AI engine that goes and generates that paper, and it takes five minutes instead of five months, that’s a huge cost savings. And there. A lot of parts of the financial service industry that just create paper. It might be you might might be support you need for a credit decision that you’re already going to do, but you need to go collect all that if you ever got apply for a mortgage. Great example, there was, like, tons and tons of paper associated with that. It’s all there for a reason. It’s all important in certain circumstances. It’s not necessarily all important to be done every single time by a human being. And so if you can find ways to kind of create, make, make that process automated, it’s really valuable.

You know, think about really expensive law firms that are reviewing a law firm might be reviewing multiple 100 page long documents associated with an extension of credit to a company, or the COVID signal back and forth. You know, a lot of that’s, you know, rope, boiler plate. It’s there for regulatory and legal reasons, and you’re still, every time you do all these deals, you’re spent, you might be paying millions of dollars to a fancy law firm to review all that we’re seeing that those types of the business can get start getting kind of get commoditized down very, very aggressively and very quickly.

Yeah, we’re seeing new technologies, like, kind of Horizon technologies are going a lot faster than you’ll be given credit for. Like, you know, there’s a lot of advances in quantum the first kind of uses of that will be in financial services, increasingly personalized and really intelligent ways of thinking about commerce. So we have a company a portfolio called aisle. Really interesting. They essentially connect brands directly to consumers. So instead of like you see an ad right now for, for, you know, Red Bull or something on online, online, and then maybe, maybe you go buy a Red Bull. And then, like, Red Bull kind of has to figure out, well, did the ad? Did it work, right? What happened here, attribution, models, all that stuff. Well, now this company allows Red Bull just, hey, go buy a Red Bull today, and we’ll just pay you back. And in exchange, like, the consumer gets a free Red Bull. That Red Bull gets to know exactly who the customer is, where they live, they shop. It’s like, acquiring a customer, post purchase in a way. And you know who they are. And very cool. That. So that’s, that’s a really good example of, you know, going to, kind of the future of commerce, where it becomes a lot more personalized, a lot more specific, and I think a lot a lot better, you know, kind of across the board.

The social impact of fintech

Certainly. I mean, I think you know when. So I, you know, I started my career. I started an accelerator that was backed by JPMorgan Chase in partnership with a nonprofit. And so we’re very focused on kind of, very consumer friendly financial services innovations. So we were investors in a company called dave.com which eventually has gotten now gone public and to help consumers avoid overdraft fees. You know, that’s probably on the podcast a few times. Yeah, that’s a really good example. I mean, I think we’re, you know that, like, as a public company, he had a, he had a little bit of a roller coaster ride. And, you know, over the last, I think last year was, like, the best performing stock, and like the net, like the Russell built a real business, yeah, and, and I think that that goes to show that, you know, if you dollar advances, right, yeah, yeah. If you have a, really, if you have an, if you have a, if you have a solution that really helps people, there’s, there’s a lot of, there’s a lot in that.

I mean, I think, I think it’s been, you haven’t heard as much about them, because I think the investor, investment community has gotten more concerned about, you know, kind of consumer businesses, large, I will tell you, as an investor in a number of these, because almost all these businesses are going to consumer facing, right, like you’re helping low income people or more moderate income people do something like, You need to acquire those people. You serve those people. There’s, there’s, there’s regulatory. Historically, there was regulatory kind of issues associated with, with, we’re serving those people. And so that was one category that was really kind of hit hard, kind of in that kind of post COVID, kind of, you know, FinTech, no crash again. Underlying company performance has been extremely strong. And, you know, Dave is a public company, and so anyone can see that, you know, that company grew throughout the last couple of years, it became profitable. As you said, you know, you kind of create a real business and that, and we’re seeing that kind of across the board. So I think investor sent them will probably catch up, and they’ll probably start hearing more about those types of solutions.

I’ll tell you that is one area where, where all of these generative AI. Tools are actually going to have a real big impact, I think, on customers. How so positive well we have so we have a company in the portfolio, small, small firm called charge back and basically look at your subscriptions that you rocket money has a similar solution with this too. They kind of look at your subscriptions, look for things that you can cancel, and kind of proactively go out there and try to save you money, cancels permission you might not be be using, and really just kind of low out there go looking for how to, how to, how to save, how to save consumers money. Well, they’re the ability to that, that that service, and I’m sure that with the team at at rocket has also made just dramatic improvements in what’s possible there, because I’m no longer just looking for, you know, Netflix to show up for, you know, 1399 every month. And these tools can go through and say, Okay, what? What it like, what are you actually using? Like, right? Like, I can connect your, you know, your browser history. Like, maybe you are getting a lot of value out of Netflix. Maybe there’s a service you signed up for that you really should cancel. Or maybe there’s a you bought something and you should have got a refund because they violated the terms of service and you didn’t know. And that is just that is a level of sophistication beyond where you saw before I saw I read something.

This is kind of off, you know, not, not really fintech. But I read something somewhere, some, some, you know, business, it was basically taking advantage of these individual arbitration clauses like forced arbitration. And everybody has been forced into, like, whenever you sign up or something, you basically agree to just binding arbitration. And the reason the companies do that is because, like, the most you’re gonna win is, like, $100 and I think this company was going, I basically, basically just doing this at like, mass scale. So like, instead of, like, you know, Disney video getting to fight you over $100 and you stop being worth it to you, like, they’re fighting 1000 fights for $100 across the country. And it’s just like, it’s more expensive than a loss it would have been. And so, like, that kind of stuff either requires a huge amount of technology to do that. But I think, I think you’re kind of going to see, see more of that in the coming years.

About Restive’s investment approach

Yeah, yeah. So we’re early stage technology investors. Our goal is to really be the first money into the companies and founders we back. So we like to say, you know, nothing’s too early for us. And you know, we are probably the first capital in the mains companies, and probably about a quarter to 30% of the time, and then, you know, the majority of the time, we’re going to be kind of pre seed investors. And so that might be a founder that’s raising, you know, let’s say one to $3 million probably, you know, pre might, might be pre product might be, you know, a couple months after rolling out a product. So probably, probably earlier than you assume, for kind of product market fit. But typically, we can get a sense of what they’re doing, understand what their vision is. And you might be a team of, you know, four, four or five people is kind of on average, and our strategy is to write relatively small initial checks. So our first check is about a half a million dollars into most these companies.

And then we work really closely with the founders to really help them to kind of to connect them to the broader financial services industry. So like I said, we’re looking for technology businesses just happen to touch the financial service ecosystem. So they might want to sell into them. They might want to manage, handle payments. They might want to, you know, access financial, financial data. And so we can bring a lot of expertise to the companies, and what we find is that can really be transformative to the best teams. And then we’ll look to really kind of dramatically build on our positions in these companies very quickly and grow and scale with them as they grow their businesses. So we’re pretty high frequency investors where, you know, we’re investing about once a month, we’ll find it. We’ll find a deal we like to do. And you know, like we at the outset, you think we were actually probably close to about 80 portfolio companies at this point. We’re now investing out of our third fund. And you know, we’re all, you know, former FinTech, you know, founders and operators, and so we really pride ourselves on being able to really try to become an extension of the management team and hopefully open up doors and kind of take things off the plate of the founders we’re working with, so that they can just move, move faster and grow more quickly.

Collaboration with founders

I think, I think most founders want help that’s helpful, right, right, like resistant against help that’s not helpful. We do try to be that help you with this podcast. You’re, like, probably not. You can sit there and like, you know, have a quiet room you can sit in. That would be the most helpful thing. Like, y’all need you with the dials and so.

We are, we are helpful in a really specific ways. We’re helpful in helping connect you the financial services you’re helping if you need to figure out, like a complex issue around your legal or regulatory dynamics, or you need expand your network to sell it or do more partnerships, if you’ve got a business that’s going to raise a lot of money, you know, our model is to connect our founders to downstream investors, and we spend a lot of time helping them build those relationships. And so if you know, for say, You got to bring it back to Jason today, if you know we’re one of the first investors in that company, help connect them to a series B investors, and we continue to be investors in that company now. And so we really see this as a really long term relationship. And, you know, try to be, try to be helpful in a way that’s, you know, going to be constructive to the relationship, and are going to get out of the way, or we’re not.

So we generally to that set. We generally aren’t taking board seats. As our view is, we’re really good at kind of pre seed and seed not super good at, like, series D, and like the decisions around going public, like, I don’t have great advice on who to your 18th engineering hire should be that, but there are investors who are really good at that, and those people should be on your board and and that. And you should the business should where it’s at in this life cycle. And so we are very focused on the part of the market we sit in. And I think we’re probably some of it, hopefully the most, most helpful investors to our founders at that category. And I what we found is, is most founders are quite appreciative of that, support. And, you know, they’re trying to build big businesses. And there’s a lot of talk of the Billion Dollar Startup of one person. I haven’t seen it yet. Yeah, we certainly have a number of billion dollar startups that have many people in them, and managing other people is hard and requires, you know, requires a lot of people helping, helping out to get there.

Geographic focus

Pretty heavy focus on the US. We have companies outside of the US market. But, you know, this is the market we know well, and you know, going to your earlier point. I mean, we stick to, we can what we know and where we think we can have a big impact. From an investment standpoint, this is also, like, the US financial services industry is maybe, maybe outside of, like, you know, big tech, the largest pool of revenue and profits in the global economy. And it’s a pretty dynamic one, where, you know, you have an interesting idea, you can very quickly get a lot of them. And so we think it’s a pretty good place to practice venture.

Evolution of partnerships with financial institutions

It’s gotten, I think, a lot more constructive for startups? Okay, great. I think it kind of to kind of two, two ways. One, there’s a, you know, I first started investing in 2014 2015 I was working, we very close to JP Morgan and very small startups. And I’d say it was a pretty common view that, well, we’re gonna, this will help us to partner with JP Morgan, and we’d have to be like, No, it’s not there. And that’s not the case anymore. I think there’s. There’s a lot of smaller financial institutions and banks in this country, across the board, and and also large FinTech companies that which has totally changed the dynamic of partnership. So if you’re just starting out, and maybe you’ve got it, maybe you’re a priest, you know, seed stage company, you’ve got a product in market, you can go and find like, stage appropriate partnerships, whether that’s an issue and maybe, maybe through handling payments. There’s, there’s banks that will do that if you’re looking to kind of, you know, sell into larger incumbents, or there’s kind of smaller, larger incumbents that will, that will buy the product and test it out.

And I think that the kind of that, let’s say that mid market category of financial services businesses that might do, you know, 50 to a couple 100 million dollars in revenue is they’re. Actually very smart now on technology. And there’s a whole more than I could that I know that would, that would be able, that would be excited to partner with startups, almost any stage, in any category. And then I think the larger financial institutions have also gotten very sophisticated, and for the most part, and how they engage with, kind of with startups, you know many of them, you know, many of the the venture capital programs, internal ones that they started, you know, maybe a decade ago now, are actually very sophisticated, really well run organizations that behave, you know, quite similar to VC funds. And so they’re looking for, they’re looking for investments that are going to make money for their companies, and also where there’s a strategic element.

But they’re, they’re, they’re much smarter. I don’t say that’s most that’s not the right way to any they’re, they’re just, they’ve come a lot more realistic on like, how this partnership can work, and like, with the constraints that that they like, the limits of how much a startup can affect their business, and how their own business could affect this. Affect a startup. And so I think it’s actually, again, going back to this has actually been a great couple of years in FinTech, because it’s a much more constructive environment for those partnerships, you know, like, or I can remember horror stories, you know, a decade ago where a startup would start working with a big financial institution and just get the Death Valley of meetings and pilots and all those kind of stuff, you just don’t see that as much anymore.

Can cryptocurrency and blockchain drive fintech innovation? Stanford’s Lisa Nestor weighs in

cryptocurrency lisa nestor

Could cryptocurrency be the key to bridging financial gaps? Can it create a more inclusive global economy?

Digital assets like stablecoins and blockchain technology are reshaping how we think about money. Their potential to level the financial playing field is becoming clearer. In today’s episode of the Tearsheet podcast, I sit down with Lisa Nestor, Research Director at the Stanford Future of Digital Currency Initiative to discuss how fintech innovation is paving the way for broader financial inclusion.

Lisa’s expertise spans blockchain technology, cryptocurrency, and fintech innovation. This makes her a leading voice in understanding the intersection of these fields.

Lisa’s career reflects a deep commitment to financial inclusion. 

“When I started researching Stellar,” Lisa shares. “It brought together what I had seen [and demonstrated] the power of providing open-source financial infrastructure.” This passion for creating accessible financial systems has guided her work. It also included her current research on stablecoins and digital dollar adoption.  

Lisa explains how cryptocurrency, stablecoins, and blockchain can make finance fairer. Her insights show how these innovations affect cross-border payments and financial inclusion. She also discusses their role in the evolving fintech landscape.

Cryptocurrency and Financial Inclusion  

Cryptocurrency has the potential to address the uneven access to financial services worldwide. Blockchain technology allows people in underserved regions to access digital wallets and stablecoins.

With new financial tools, more people can save, transact, and even earn. “Access to financial services is not an even playing field,” Lisa notes. “Distributed ledger technology can help level that field. It can do so by providing accessible and stable financial options.”

Stablecoins: Beyond Trading to Real-World Impact

Stablecoins are already impacting cross-border payments and savings in regions with unstable economies. Lisa highlights Argentina as a case study. She says, “Argentina’s economic situation has created a huge demand for digital dollars, with stablecoins playing a crucial role in hedging inflation and providing financial security.”

Digital Dollar Economy and Cross-Border Payments 

Lisa emphasizes how digital dollars simplify cross-border payments, especially for regions with limited traditional banking infrastructure. “Being able to hold a stablecoin in a digital wallet and earning some yield on it is a small but significant step towards democratizing finance,” she says.

Tokenization of Real-World Assets

Another emerging trend Lisa identifies is the tokenization of real-world assets (RWA). Blockchain makes traditionally illiquid assets, like real estate and art, more liquid.

This opens up global markets. “This approach improves liquidity. It makes these assets move seamlessly across the globe,” Lisa explains.

Fintech Trends in Digital Asset Adoption  

Lisa explores CBDCs (Central Bank Digital Currencies) and private stablecoins. She looks at how governments and businesses are adopting digital assets. She also discusses the opportunities and challenges they face. “Most central banks are researching how to launch CBDCs without negatively impacting their banking industry,” she says. Lisa highlights a cautious yet growing interest in these tools.

The Big Ideas

1. Open financial infrastructure creates a global ledger accessible to all. “The idea is to create a ledger that every financial institution in the world can operate on but can’t buy. It is open and available to everyone.”

2. Stablecoins provide financial security in unstable economies. “In emerging markets like Argentina, stablecoins offer a way to hedge inflation. They secure savings amidst economic instability.”

3. Tokenizing real-world assets improves liquidity and global accessibility. “Tokenizing existing assets brings improved liquidity and global accessibility to traditionally illiquid markets.”

4. Governments explore CBDCs to complement existing banking systems. “Central banks are focused on introducing CBDCs that complement. Rather than compete with, existing banking systems.”  

5. Digital dollars empower individuals in the gig economy. “More individuals are earning in digital dollars through online work. This is creating new economic opportunities without physical migration.”  

Listen to the full episode

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Watch the full episode