From Social-Good Challengers to the Creator Economy, Cowboy Ventures’ Jillian Williams Is Excited about NYC Fintech

Jillian Williams has been in venture for the past five years, first at Anthemis and now as a New York outpost for Cowboy Ventures. “I'm from New York and have no plans to leave,” she says of her move to the West Coast-based shop. “I'm excited to see that we continue to have great top-tier talent come to New York and grow out of these companies already here. I think there's a lot ahead for the New York ecosystem.” Here’s a peek at what’s most exciting to her now. 

Given your loyalty to the New York tech scene, let’s start there: Why do you like investing in Fintech in New York? What's special about this space?

The tech ecosystem has grown tremendously, especially over the last five years and in fintech. Having gone out to San Francisco quite a bit—I think in 2019, at least once a month or every other week—I’ve seen in comparison the evolution and the growth have been happening in New York so quickly.

I have a bias, I'm from New York, but I think it’s having all these different industries that intersect. It's not purely a tech ecosystem: You have finance; you have fashion; you have so many other things happening in New York. So much of what we do as investors and builders intertwine with areas outside of our immediate domain.

And so specifically with fintech, obviously New York is in the finance capital of the world. So you have so many people who are so, so smart about the challenges and pain points within financial services, but then given the growth of the tech ecosystem, you have all these IPOs and senior executives leaving their companies to start something new. 

The intersection of all that creates so much power. To me, it’s about bringing all that mind sharing knowledge together. And I think we’re still in pretty early innings of it. The last year or two were really where you saw a lot of exits from New York City tech, and I think we're just going to continue to see that grow even more. So I'm really bullish on what the future looks like.

Tell me more about your fintech exposure, expertise, interest. How did you get into that space?

I grew up with both of my parents working together in finance. That was really the industry that I knew and assumed everybody went into. Right after college, I went into investment banking. When I was there, I focused specifically on financial institutions. The intricacies of how insurance worked was something that made a lot of sense to me. When I spent some time on the natural resources group, that really went over my head. I really did not understand oil companies. But my background and understanding, applied to tech, just clicked, and then that's how I got into venture capital.

I wouldn't say I necessarily loved fintech immediately. That love grew and really continues to. There's so much happening in what was defined as fintech even four or five years ago versus now is so different. In my previous firm’s first fund, a lot of LPs thought fintech was really narrow for a hundred-million dollar fund. Then for the next one, they were like, "But fintech's so broad, how are you thinking about it??" 

There really is so much that financial services or products intersect with that it becomes so interesting to just look at different industries and say: “There's a clear path for seamless integration." Those ideas are really exciting to me. 

Was there a moment in your career where you were like, "Wait, I do love fintech." 

When I was much younger and just joining venture, a lot of women peers and friends focused on consumer. They would have bags of stuff like earrings and food after meeting with companies all day. And I was like, "I'm so jealous." That seems so cool, applying everyday life to what you're doing versus talking to a company that helps banks issue bonds faster.

Then, I don't remember when, but I was talking to someone about some really deep infrastructure company that I was really trying to push at Anthemis and I was like, "But it's the coolest thing in the entire world, this is amazing." And they were like, "I'm sorry, this is so boring. I get that you love this, but I don't care." And I realized how excited I was getting over fintech. It wasn’t one company that all of a sudden flipped a switch, but it was like, "Oh yeah, this is really exciting to me."

What do you look for in early-stage fintech founders?

At Cowboy we do pre-seed and seed, so 90 percent of the time there is zero revenue, often zero product. And that's the area that I really love. A lot of it's based off the founders and their backgrounds—but not even necessarily how they look on paper or where they went to school—just what makes them the person or the team that's going to win this. What from their learned experiences or understanding of the world gives them some unfair advantage? At Cowboy, we like to call someone a ‘learning animal,’ they're continuously learning and coming back to us with additional insight; the founders work together and their skills complement each other; they attract and retain talent. That is something that is extremely crucial, especially at the earliest stage: Do top-tier people want to work with you? 

And then we'll do a lot of references to understand how people work with one another, how people take feedback, et cetera. It's not necessarily that we're looking for every single reference to be this glowing remark on the person; we really want honest feedback in terms of what happens when things get hard and how this person handles challenges.

How have you helped fintech founders in your portfolio find product market fit? What are some common mistakes here? 

I think one of the challenges I see quite a bit is people solving a problem that doesn't necessarily exist or they're solving a portion of it, but not necessarily the entire aspect. So it's more of a vitamin versus prescription medication or something that's actually needed. And so, how do we really think about this market and how they're solving it and maybe the product isn't 100 percent there today, but is there enough of a big problem? Do they understand it deeply enough that they're going to be able to wiggle their way there?

Any fintech startups in the portfolio you want to shout out? Smart things they're doing, lessons that could apply to other founders?

One of the companies we're really excited about is Tally. They're later stage, but really focused on helping customers consolidate their credit card debt. In that space, today's a really interesting time, because you see especially the younger generation being so allergic to debt, especially credit card debt, but they're thinking about it in very different ways, like using Affirm instead of a traditional credit card, which is obviously still a form of debt. 

What we really believe is that there should be a healthy relationship with your debt. Debt and credit are obviously necessary in this world in terms of building up a financial profile. But at the same time, we have more debt in this country and probably in the world than ever before. And that just continues to mount, and I personally think that we're getting to an inflection point within that, and you're seeing individual challenges to that, but also seeing, with the calls to forgive student debt for example, it's becoming a national and global problem.

Tally is coming out in a very human-centric way in terms of trying to help people manage their debt and then going beyond from there. So, we're helping you with a huge pain point in your life. How do we make you from a debtor to a saver and actually grow your finances as well? 

They have this mission and know where their North Star is. Fintech broadly right now is really hot. There are so many companies building in the space because, to be fair, there's so much opportunity and there's still so much white space. You do have people that pop in opportunistically. You can build a big company that way, it could end up working. But at least for me personally, having that passion behind it is really important because things are never going to go as easy as you think.

It is exciting to see how many Fintech startups in particular seem so committed to social good in that digital space. And that's something that maybe we're not used to as consumers.‍

So at Anthemis, we were early investors in Betterment. And a lot of those types of platforms came in simple, but they were coming out of the financial crisis as consumers realized these banks were not looking out for them. And then, you have some of the demographics banks as well, First Boulevard, which focused on the Black community, or Daylight, which focuses on the LGBTQ community.

These companies address the fact that even today banks still are not looking out for those types of customers; they treat them extremely differently than they treat their high-net-worth and more privileged customers. And so I think we're at a really interesting time for fintech where all of these social issues that are happening intersect with how we use our money. 

And given banks have such a huge control over our financial future, it's great to see so many people trying to innovate, not just like, "Oh, I want to build a big company in this fintech space," but like, "I want to do so in the right way that really works for the customer and fixes a lot of these problems that have existed today."

Any other Pandemic-era trends that you're excited to see founders in this space fall for?

A lot of the infrastructure companies are ones that I'm super excited about in terms of going into the picks and shovels of helping to build and offer different types of financial products very, very easily. I think another one that grew from the pandemic is the creator economy. Obviously it's existed for a lot of time, but when people were at home, more so, and had a lot more free time, I think that has helped it blossom.

It intersects with this future of the market for Gen Z, which is really fascinating to me as well, where they're really bucking the financial system and what we've all believed to be true for so long, and finding different ways to make money, like through TikTok and YouTube, but also finding advice via these platforms to really learn more about what they should and shouldn't be doing in financial services. Not saying it's always the best advice necessarily, but I think it's really interesting to see them go against what we've all been told.