Why Founders Need Attention, Not Just Capital

Ian, I'm delighted with that pronunciation, and I'm fabulous. How are you?

Thank you. First of all, it's a real honour and a privilege to be on this platform. I've been a big fan of the work you've been doing in the fintech space. The fintech ecosystem is a small world in a lot of ways, so I'm delighted to share the platform with people who really understand the space we're building in and the folks we work with. Today I'm building a venture and media platform called Armada Ventures. We have a twofold mandate: one, to back founders at the earliest stages doing incredible work across financial infrastructure; and two, to provide support to not only founders but also funds who are seeking to advance in media and narrative and to build their positioning on a global scale. This leverages my background as someone who's been an investor, an operator, and also a media agent, for lack of a better term. I've been an investor for over a decade and in media for almost a decade, so we think we occupy a really unique spot within the ecosystem, investing in media in a way that few do. I'm sure we'll talk about that more. In terms of background, you could spend a whole hour on it, so I'll try to hit the highlight reel, and I'd encourage anyone listening to connect with me on LinkedIn to fill in the gaps. I started my career in technology, working in strategic finance at Netflix, back in the days when we were still shipping DVDs. I got to do really cool things like launch originals, pivot to streaming, and do the international expansion that made Netflix into a household name. I joined when the stock was about $25. Post-split it hasn't been as exciting to watch, because it's hovering at about a hundred or so, or maybe I'm wrong. I spent three years in Silicon Valley before making my way to the investment side. To summarise, I've spent time on pretty much every side of the capital stack, from oil and gas private equity, to leading corporate development at Vanguard and getting my first flavour of fintech partnerships, to spending time as an allocator, as a limited partner for a $7 billion foundation here in Los Angeles, allocating into private equity, venture capital, and public equities managers. That perspective has imbued me with a strong sense of how every part of the capital ecosystem connects, and it's what makes the work I do today such a joy.

Yes, exactly.

I think I kind of stumbled into it by accident, but in hindsight the building blocks were all there. I'll go way back to high school, if that's okay with you, because this is how fintech grew for me.

Even as a young person, I was never someone who accepted the status quo. I was always interested in innovation and what it meant for me. To age myself a little, I remember when the iPod came out, and I did my research on the type of MP3 player I wanted. I had this whole dossier that I sent to my dad, and I said, "Dad, I believe the best MP3 player for me is actually an iRiver, because it has a colour screen, the scroll is vertical, it has an FM/AM radio function, which is really important to me, Dad, and I can customise the colours." In the grand scheme of things, I was wrong. The iRiver no longer exists. But it should indicate the kind of diligence and enthusiasm I had for new technologies and figuring out what makes sense for me. Fast forward to when I graduated from business school. I went to Kellogg for my MBA, and I had this brilliant opportunity to join Vanguard on their corporate strategy team. When they gave me options of which part of the business to work on, there was this fintech part, and I was so shocked that no one I talked to was interested in it. I was like, "Guys, this is innovation. Vanguard, we manage 8 trillion, we invented ETFs, this is so cool." And it was just crickets in the corner. So that's how I really came into fintech: that combination of an early interest in what's new and at the edge, and having the chance to do it at a company as big and immersed in that space as Vanguard. That's how I got the practitioner lens. The timing was around 2019, 2020, so the pandemic started and, long story short, I found myself with time on my hands. I've always enjoyed writing, so I started writing, and through the writing I pitched myself to a couple of platforms, including Forbes. They looked at my writing, which was actually personal finance writing, and said, "You can write about finance and you work at Vanguard, you're going to be covering fintech." And I was like, "What is fintech?" With that question, I embarked on this whole journey I've been on ever since.

A couple of things. Maybe I'll approach it as the investor lens, the operator lens, and the writing lens. The easiest is the writing lens. As someone who covers fintech for a couple of publications, and now focuses on it for my newsletter, what I get to do that a lot of other folks don't is read a ton. I get a ton of PR inbounds and I'm constantly scanning the headlines to see what's happening in fintech. As a result, you build this mental map of the different types of competitors and solutions. You start seeing things that rhyme or repeat, and after 20 similar announcements you think, okay, this area is saturated. That's one angle. As an investor who's done direct investing into early stages, everything from pre-seed through Series B, both from the enterprise lens at Vanguard and the earlier side of things, I've seen what it takes for financial technology to get underwritten and to partner with large enterprises. I've learned that your product isn't enough; it can't just be a feature. It's got to be about the full life of the product and the way it can integrate. Then, as an allocator, this silent but mighty, almost omniscient piece of the ecosystem, these are the people who give money to venture capital and private equity funds. So it all comes back to: if you purport to identify really promising technologies, do you understand what it takes for them to grow? Can you help them reach enterprise scale? And can you execute on that such that the limited partners can believe in your vision? Even though they all seem distinct, they come back to the same thing. For fintech to be really impactful, it's got to make sense across all three of those non-obvious areas. That's where my lens allows me to have, I don't know if it's the right point of view, but it is a distinct point of view.

Correct, I'm the founder. For me, one of the reasons I really like financial technology, infrastructure, and regulated industries is that, by nature, the high barriers to entry are a kind of moat in themselves. Very few people think, "You know what, I'm going to build another bank." Maybe in 2020 they did, but these days it's a very limited number of people who understand the ecosystem well enough to think of a better solution and who have the right networks, skills, and experiences to bring something together. That's why I enjoy backing founders building for financial infrastructure. Most of the time they've been operators or practitioners themselves; they've seen it firsthand, and they have that founder-market fit, that advantage of understanding the problem and how to solve it in a nuanced way that accounts for things like compliance. We really back founders who have the vision to build fintech solutions that become a platform. For example, I was reading about how AI can now manage your subscriptions for you, and I remembered there were entire companies that raised millions of dollars as subscription-management solutions. In this new era, I don't think that's an easily underwritable company anymore. Subscription management might be a feature you build, but to be a backable founder for someone like Armada, it would have to be a wedge that then lets you build out something bigger, like holistic wealth management for your customers. So having that platform vision from day one is important for the founders I like to work with.

I shouldn't be surprised, but I still see so many pitches for financial wellness. Even though that's a category I've pretty much drawn a line in the sand around, in my opinion it's not an investable category for what I'm building, although I support financial literacy, which is literally why I have a podcast about it. I still see a lot of people trying to do things with financial wellness, in different approaches. Some are doing DTC with apps, some are going more B2B, leveraging benefits platforms. But it's a category I continue to see as crowded, hard to differentiate in and, most importantly, difficult to monetise and scale. A corollary is neobanks. You see it with a company like Chime. Sorry if you're listening, Chime, but I think we can all agree you're really good at the customer-acquisition piece. As customers scale and their bank accounts grow, though, that feature set no longer serves them, so Chime has a huge problem with retention and is constantly having to turn that customer-acquisition engine. I see a lot of similar examples with personal finance: great, you've got them with the hook, you gave them some resources, but as their investments grow, what you're offering no longer serves them as they build wealth. So it's a crowded area. I actually just heard a company today come back and I thought, "We're still doing this?"

Hot take: I just don't think it's monetisable. I always had a good metaphor for this, until GLP-1s came about, and now I'm like, okay, fine, GLP-1s, you won. But before GLP-1s, I'd say financial wellbeing is a lot like physical wellbeing, in the sense that everyone knows what needs to be done. There isn't an injection you can give yourself to suddenly become financially literate. Then GLP-1s happened, and, well, there is a drug for weight loss now, but there isn't one for financial literacy. So the tools and the resources are all there; it's about access and discipline. That's where I see a lot of content creators having this niche on lock, and AI doing really cool things, even though a lot of VCs don't want to admit it. I'll also say the real bet is around communities that are underbanked and face systemic exclusion from financial systems. Ironically, those are the areas no VCs are backing, because a lot of VCs don't perceive it as a challenge; it doesn't affect their lives or their world. On the education piece, that's kind of solved for. But connecting the gap between what you should be doing and how to actually do it, that glue, is where a lot of communities can still benefit. I'm not sure fintech is the answer, but that is where I still see a meaningful gap for education.

You're free to do whatever you feel with your personal finances. Someone once told me that personal finance is more personal than finance, and I totally agree. Where I'm a little wary of agentic solutions is, one, the data: garbage in, garbage out. I don't have confidence in the data sets they're trained on. For example, I'm an immigrant; my family and I are immigrants. How we approach everything from risk management to time allocation, I'm not confident a model has been trained on that. Sometimes when I talk to Claude, I'll literally say, "Claude, you sound like a frat boy, I don't like anything you're telling me." So why would I trust Claude, who can't even construct good sentences, to give me financial guidance? I'm a bit sceptical about the data sets. The other thing: I was at a session for my alma mater, the University of Pennsylvania, where some current engineering students talked about what they're working on. One young woman was working on a robotics project in San Francisco with self-driving cars, not Waymo but something similar, and she made the limitations very clear. Data sets are only as good as what they're trained on, but agentic systems don't have the same context we have as humans to think through when something unpredictable happens. In an age where seemingly every other day there's something unpredictable, that's where the agentic value proposition can be more tenuous. If a market correction hits, or we're seeing Anthropic valuations of two trillion, how index funds are weighted looks completely different today than it did pre-pandemic in 2019. So while I think it could give a good overarching picture frame for your financial guidance, how you paint within that frame is going to be up to the individual, and that's where the limitations for agentic lie. That said, what I like about agentic solutions, and AI in financial services or financial literacy more broadly, is that whatever gets people comfortable talking about their finances, whether it's an agent or a person, is the big win.

I don't think this is anything new. Even several years ago, when I was looking at early solutions, I would always ask what's proprietary, what's the moat. Back then there were many companies that were essentially wrappers, where they'd leverage an LLM or some data set and guide the output, but it was basically a wrapper. That wasn't interesting to me then, and it's even less interesting today, so the days of any kind of wrapper are far gone. But I also find the conversation around SaaS-pocalypse interesting, because sometimes when people say the word I want to quote Jennifer Lawrence on Hot Ones, where she's almost crying and says, "What do you mean? What do you mean?" I do wonder what exactly people are referring to, because I see several different things going on. One, there's a sense of jitteriness around public markets and the influence of SaaS on public-market valuations, which we're watching too. Two, it's about how companies are using these tools internally, both at the enterprise layer and at early-stage companies. For example, a founder of a company I backed earlier this year said they used to have a team of people for software engineering and now they use agents; the founder was a software engineer himself, so he's comfortable with that decision. Then the third layer of SaaS-pocalypse is in private markets, not just venture capital but private equity, where these same dynamics are compressing valuation multiples and changing how you make exits. It used to be that you'd package up a SaaS company, sell it to a bigger SaaS company, and call it a day. So my counter-question would be: which aspect of SaaS-pocalypse are we referring to? Each of those three has nuanced characteristics.

That's a good question. It's interesting, because this year I had the chance to go to Money20/20 Europe for the first time, and I had a great experience in Amsterdam. But one of the overarching sentiments I heard from a lot of attendees was that this year's edition was much smaller than prior years, the feeling being that fintech is a little quieter than the hype eras of 2019 and 2020, when everything was a neobank and everything was a fintech as long as it had an automation. So there's a sense within the industry that the headlines are a bit more muted; companies that want press for fundraising announcements find it harder to get that level of interest. That said, in terms of excitement and investable opportunity, it's not a coincidence that some of the companies you highlighted are not in the United States, and quite a few are in emerging markets. I continue to see significant opportunity across LatAm and the African continent. One reason I started writing my newsletter is that I began mapping trends around mobile infrastructure and mobile-first banking happening at large scale in places like Nigeria, and connecting the dots. I'm from Kentucky, and there are lots of pockets where broadband doesn't penetrate, so how can you deliver a superior banking experience to those populations too? I still see lots of opportunity for innovation in these more regional markets. Maybe my vision for a global financial infrastructure is a little too idealistic, but there are a lot of inefficiencies in these banking systems. The classic example is Nubank and what they did in Brazil, opening up a customer category long seen as unprofitable or too thin-margin for the traditional incumbents. So emerging markets, financial infrastructure, mobile money, and digital-first products continue to be really exciting. They're just probably outside the world a lot of US venture capital investors are spending time on.

There are so many things, which is why I've taken to TikTok to talk about this last point. But to your first question, what do people need besides capital? This is where the opportunity for Armada has been really big. As a writer covering fintech for a while, it's been great to see founders who've read my coverage or listened to the show say, "We like how you write about this; can you help us with how we position ourselves?" Founders in regulated industries are finally understanding that to unlock capital you need to convince people. You have to convince people to join your company, to invest in your cap table, and if you can do all that, you can probably convince the media that your company is worth talking about. Early-stage company building is that game of getting people to believe in you, period. It's great to see more founders realise that and reach out to us for help. What's happening in media, with the landscape being more fragmented, means there are more opportunities to be on podcasts like yours and featured in newsletters. Attention is much more scattered now, which is a great opportunity for early-stage founders who can operate with finesse and savvy, who don't need huge PR teams but who can reach out with their expertise and say, "I can talk to you about this." So attention is the thing founders need more than anything. What's also interesting, having built my own fund and worked at different funds, is that founders still need a lot of support. So many come to us and say, "Can you help us with introductions, because we know you have relationships with these enterprise clients? Can you help us with media?" And I'll say, "Wait a minute, you have a cap table, where are the introductions from them?" And they'll say the investors just sent them an Excel sheet. So VCs can talk all day about how much help they offer, but the fact is I'm still seeing a great number of opportunities to support founders with business development, positioning, and strategy. We want to be that call, and we're happy to serve them. So it's two things: attention and narrative, plus introductions to the right enterprise clients, the people who can champion you. Especially in fintech, the most logical outcome for a lot of early-stage companies isn't an IPO, it's probably an acquisition. So the sooner you can get in front of a Mastercard or a Visa, the better, and by the way, Mastercard and Visa are also reading the news, so the more places they've read about your company, the better off you'll be. I'd actually be curious what you've seen in this regard. My experience is that there's a K-shaped economy for venture capital fundraising. There's one side of the K raising mega-rounds from the Andreessens, the General Catalysts, the Sequoias, and that's plugging along nicely. But I've also seen more founders say, "I'm going to raise a smaller round. I just want a couple of strategics on my cap table who can unlock those doors, those customer relationships. I want to close that round faster." Almost a hybrid of bootstrapping and venture capital. Whereas before, the standard would have been "I just need a five-million-dollar round to get my idea running," coming back to SaaS-pocalypse, in a way it's become: if you need a round that big, what are you really doing? Don't you have these tools at your disposal to test your hypothesis? So I'm really interested to see what happens with round sizes, how long companies stay private, and how many Series A and subsequent rounds there even are, because there are huge implications based on founders opting for smaller rounds and longer runway. Does that make sense?

I was going to circle back to the media side, if that's okay. One thing I noticed early on, when I started writing for some publications, was the number of times I'd cover a company at a seed round and then they'd go on to become unicorns and raise mega-rounds. At first I thought they were just a great company, but now I definitely see a link between media mention, how you position your brand, and the valuation you're able to command. The best founders harness media to drive their valuation and their credibility. I'm not saying that being written about in the Wall Street Journal makes you a great company, or means you'll have a huge exit. But as I look back over my career and the companies I wrote about that I thought were doing cool work, some of the best founders came back and said, "You put us on the map; because of that coverage we were able to convince these investors." They were able to go from strength to strength, like swinging confidently from one monkey bar to the next in gym class. That's the angle on media I really wanted to emphasise.

Longer than most marriages, actually, probably too.

It's funny you said "shrouded in secrecy," because the Bear and the Bull is called that because it literally was shrouded in secrecy; it was anonymous. I was a faceless account on Instagram. I was scared of social media and didn't know what I was doing, and I'm a peak millennial. Remember when we had chat rooms and it was "never say your name, ever"? My AOL username was CoolBeTiny, just in case anyone was wondering. So that's the Ilona lore: be anonymous. The brand started because I was writing anonymously about personal finance, and then when I was picked up as a contributor for Forbes, I was like, well, that's my name, so what am I going to do? I had to come out of the shadows. In terms of my own writing platform, it's taken different shapes. For a long time I wasn't doing as much independent writing, because I was focusing on my bylines for places like Forbes, and now Entrepreneur and Fintech Futures. But I really revived the Bear and the Bull brand about two years ago, because as I took on more coverage and said yes to more media opportunities, I realised there were more stories I wanted to tell than I could realistically publish in places like Forbes, or where my tone and voice were a little different. That prompted the resurgence of my newsletter, which is weekly for the most part; I think 90% of the time it's been weekly, so I'm pretty happy with that. For me, as it pertains to investing and doing anything, writing is thinking. The best way to flesh out your thoughts is to write them down, and really write them, not just dictate them. When I'm doing deep writing, I'll take pen and paper and write out what I have going on. So it's been a great way to highlight areas that don't always translate to mainstream bylines, to remove myself from the pressure of needing certain clicks to make an article worthwhile, and, more importantly, to give myself discipline and structure around how I think about opportunities. Writing clarifies my thinking and lets me take a better position on things. You must think in order to write, and so writing makes you a better thinker.

The coolest real-world impact, and if anyone's a subscriber, email us, give us the thumbs up, has come from a little section in every newsletter where I say where I'll be in the world. The number of times people have said, "Hey, I heard you're in town, want to meet for coffee," and I say, "How did you know?" and they say, "I read your newsletter, duh." So as a way to stay connected with people, that little section has been the most fun; people follow up or connect me to someone. It's always awesome when someone responds to say, "You changed how I thought about this." I've had a couple of founders say, "The way you wrote about this company changed how we're building our product, thank you for shining a light on that." What's also been cool, coming back to media being fragmented, is that I've been doing more contributed op-eds highlighting different founders and CEOs. Most founders don't really care where they're featured, they just want to be talked about, and one thing I have in my network is a lot of founders. So reaching out to founders doing cool things, giving them the platform of the newsletter, they share it, and that way the platform grows. It's been nothing but positive. I've gotten some really cool subscribers, fintech celebrities, if I may say so myself, and seeing that reach has been wonderful.

The one a lot of people liked, because of the headline, was something like "Silicon Valley just discovered menopause." It was a better headline than I'm remembering, but it was a critical take on where early-stage investing is going in women's health. I like that too, because just because you cover fintech doesn't mean you don't understand other regulated industries, and women's health is an area with a lot of discussion and activity. I can't believe I butchered my own headline, because it was so catchy, but so many people said, "My God, that headline, I immediately read it." That gives you a flavour, because I'm also a little bit contrarian and I think that comes through in my writing.

That's a good point. In general, I think my strength as a writer is that I have a strong voice, and I also do a lot of good research. So I don't see it as a challenging balance. In college, a professor gave me feedback on one of my papers, and, not to brag, but I will, he said my writing could make him weep and that my prose was punchy. I'll never forget it, he said, "It's punchy." I try to think about that when I write; I try to make my prose really punchy, because it brought the professor almost to tears, so it's good writing. The professor wouldn't lie. For me, that's not a bug, it's a feature. I'll tell on myself here: one time I did a collaboration with a brand for my newsletter, I was running out of time, and I thought, I'll get the general ideas but I need Claude to help me backfill some of this. My God, they tore it to shreds, and I'm so glad they did, because they said, "We want your voice, your prose, your punchiness." That was an aha moment for me. Nowadays I really limit how much I use AI for anything related to writing. My point of view is the reason I was able to write with Forbes, and maybe the reason I'm on this podcast. The more I water down my point of view, the less fun I'm having and the less people care; the more I give that real point of view and punchy prose, the more people want to read it, because that's the craft, and it's rare. Anybody can read an AI-generated whatever, but the tone is what matters.

Thank you so much. I started Money Memories on my own, again in 2020. 2020 is the year of the Alonnaissance, when I started writing. At the beginning of the conversation we talked about how this all started with financial literacy, so I started writing about financial literacy. When the writing got picked up and I started writing about fintech, I still wanted to talk about financial literacy, but I felt there were already a lot of written resources, and I didn't want to get lost in the sauce of another 401(k) resource. In my conversations with people, it was the emotions around money that caused the most consternation. So Money Memories was born. I was literally on a walk when mental lightning struck: "Money memories, I'll ask you about your earliest money memories," and that would be the appetiser into talking about career and all those things. We've had the privilege of doing it for six years now. Initially I was independently distributed, doing it myself, and then I reached out to my local NPR affiliate in Louisville, Kentucky, and said, "I have this podcast, can you do something with it?" They said, "We'd love to distribute this show," and we've had this wonderful collaboration ever since. Now we're doing live shows. Today is October 12th, and we have our fourth live show of 2026, with LA Tech Week. It's been so fun. The podcasting world is still kind of the wild west in media in a lot of ways, but I love it; it's a really fun way to be creative and connect with awesome people like yourself.

I've met so many. One that stands out: an earlier guest shared that her father took out a payday loan to take her and her sister to the local state fair. First of all, what a memory, and what a thing to talk about, going back to having honest money conversations. In terms of how that shapes financial products, a lot of financial solutions these days continue to go towards the affluent, and with the SpaceX IPOs and things like that, we're getting more solutions for people coming into wealth. But many people's families are doing things like this, putting themselves at the bleeding edge of financial collapse just to do something better for their children or families. It's also an exercise in not judging; again, personal finance is more personal than finance. Everyone is doing the best they can with the decisions and information available to them at that point in time. Sometimes there's a tendency to treat a financial decision as, "Well, you made this poor choice, so you deserve this high interest," and it's like, no, these systems aren't always designed for long-term success. So that's a story that sticks out in my mind in a lot of ways.

You can connect with me on LinkedIn, if you know how to spell my name. If you're building in financial infrastructure, or need support getting your story in front of the right audiences and getting it right so it can move capital, we'd love to connect with you. Our website is Armada-Ventures.com. I'm on TikTok, I'm on Instagram, and please subscribe to my newsletter, Bear and the Bull. If I don't hear from you guys by the end of the show, it's because you chose not to connect with me, and that's okay with me too.