There is a moment in this conversation where Haley Bryant, partner at Hustle Fund, describes almost passing on a company because the founder openly admitted he had no moat. His argument: in a world where software rewrites itself every few months, execution velocity is the only defensible position left. He saw that as a vulnerability. Haley saw it as exactly what she invests in. "I don't agree," she told him, not with the execution velocity point, but with the idea that it wasn't a moat. Execution velocity IS the moat. "That's our thesis. I'm writing you a check."
That moment captures the core tension running through this entire conversation. The traditional frameworks for evaluating early-stage companies (domain pedigree, proprietary technology, clearly defined moats, etc…) are dissolving faster than most investors are willing to admit. What fills the gap is less tidy but, as Haley argues, more honest: a bet on how fast a team can move, adapt, and learn.
The Investor Behind the Thesis
Haley did not arrive at venture through a conventional path. Before joining Hustle Fund, she was angel investing while building a company, advising startups, and working at content agencies and early-stage technology businesses. She describes her early days in venture as a period of real discomfort, specifically around the question of whether to be a generalist or a specialist. “I don’t know if I’m good at shifting focus so much and trying to be kind of the master of none,” she recalls thinking.
What resolved that tension, at least partially, was leaning into something she had always done naturally. Haley grew up overseas, attended a tiny international school where her graduating class included students from roughly 27 countries, and spent her career sitting at every lunch table rather than committing to just one. That instinct toward broad curiosity became a professional asset. At Hustle Fund, where she has now invested across more than 60 companies, it manifests as a portfolio with a clear spike in vertical artificial intelligence, a strong position in small business infrastructure, and a growing focus on capital-intensive markets in the Washington, D.C., region, including cybersecurity, dual-use technology, and energy.
Hustle Fund, for those unfamiliar, operates at the earliest possible entry point. Haley describes it simply: they are the first check in about half of their investments. The fund is generalist in structure but increasingly deliberate in practice, with Haley carving out specific sub-theses she can defend with real pattern recognition rather than informed guessing.
Execution Velocity as the New Underwriting Framework
The most direct expression of Hustle Fund’s current investment philosophy comes from a reference by Vedika Jain at Weekend Fund on the concept of slope. A pitch deck, as Haley frames it, is just a snapshot. What a VC is actually trying to measure is the rate at which a founder moves from one point to the next. “How quickly did they get here, and how quickly will they get to and through the next thing?” she asks. That question, more than any market size slide or competitive landscape chart, is what she is trying to answer.
Roughly 30 percent of companies that receive a first check from Hustle Fund pivot after the investment, and Haley expects that number to accelerate. The implication is uncomfortable for anyone who spent years underwriting businesses on the strength of their initial product or market position: the thing you invest in today may look entirely different in 18 months, and that may actually be a sign of health rather than instability.
She has been deliberately spending more time with teams before making a decision, specifically to observe pace. One example she raises is a company heading into a major fintech conference that she has been tracking for about six weeks without yet signing paperwork. The speed at which they have updated both their product and their investor materials is itself the signal she is watching. “That’s what we’re looking for,” she says.
On the founder character side, Haley is clear about what she is not optimizing for. She wants intensity, but she also cares about emotional intelligence, customer centricity, and the ability to build relationships. Her view is that not every transaction will eventually be executed agent to agent, and the founders who can only operate in automated environments will hit walls that relationship-builders will not.
Fintech as Infrastructure, Not Category
In the conversation, Drew frames fintech not as a vertical but as the invisible operating system running underneath businesses that do not present themselves as fintech companies at all. Haley builds on that and shares her excitement around vertical AI and the idea that once a company gets embedded in a payment flow, the switching cost becomes structural. “Once you’re in those payment flows, it’s a lot harder to rip out,” she notes.
This framing has specific implications for how both investors think about moats in the current environment. Data and distribution still function as defensible positions. Team quality matters more than ever. But what Drew identifies as particularly underappreciated is the unsexy, deep-infrastructure layer of fintech, the parts of how money moves that most generalist investors would not even know to look for. His argument is that those overlooked systems, historically unscalable, are now capable of becoming high-margin, fast-growing businesses precisely because the tooling to build and distribute them has dropped in cost dramatically.
Haley adds a related concern about the era of neo-bank proliferation, where copycat models with slightly differentiated go-to-market strategies crowded every available niche. She and Drew agree that AI has accelerated that pattern across all categories, making it harder to distinguish genuinely venture-scale companies from polished imitations. Haley has started picking up small signals in founder conversations: a founder who talks only about search engine optimization without mentioning answer engine optimization, for instance, is quietly revealing how current their thinking actually is.
Building Pipelines Through Community, Not Hunting
Haley has shifted meaningfully toward community-driven sourcing over the past year. For her, this means socializing deals more openly with trusted co-investors rather than holding a position close until a term sheet is signed. “A few years ago, I wouldn’t have done that,” she admits, explaining that it used to feel risky to signal interest before committing. The logic has reversed: in a market flooded with AI-assisted companies that are easy to build but hard to evaluate, additional perspective from people she trusts reduces risk rather than creating it.
One framework she has become genuinely enthusiastic about is what she calls the consortium model, referencing an unannounced portfolio company. The concept is straightforward: early-stage founders in adjacent spaces form a deliberate network, effectively bringing a complementary ecosystem to enterprise customers rather than showing up as a single point solution. The distribution advantage this creates, particularly in complex markets where trust and relationships drive procurement decisions, is something she expects to see more founders pursue intentionally.
She ties this back to her time before venture, when she was thinking about how to connect customers within a network so they could all benefit from each other’s momentum. “Everything is a network,” she says, and it is the lens she applies to portfolio construction, talent introductions, and co-investor relationships equally.
What Comes Next for Early-Stage Investing
Haley ends the conversation in a reflective mode, acknowledging that six weeks prior, she would have described the investment climate as genuinely unsettling. The question she keeps returning to is both practical and open-ended: what happens if the pace of change accelerates 50 times faster than current projections? What does ambitious even mean in that scenario?
Her answer, at least for now, is to keep orienting toward businesses with real barriers to entry, whether those come from founder networks, proprietary data, or deeply embedded infrastructure. A recent commitment she made to a satellite communications company in D.C., focused on laser-based data transmission as an alternative to radio frequency, reflects exactly that logic. The founder brings rare industry relationships and a specific technical hire that would be nearly impossible for an outsider to replicate. The market is enormous. The why-now is visible to anyone paying attention to where compute is moving.
That combination (a team with genuine access, a problem that requires earned knowledge to even identify, and a market that is large enough to matter) is the kind of bet Haley is increasingly drawn to. The tools to build companies are now available to nearly everyone. The ability to find the right problem and move fast enough to matter remains, for the time being, a genuinely scarce resource.
This season is supported by SVB. Silicon Valley Bank, a division of First Citizens Bank. Member FDIC. SVB is a trusted collaborator for the founders pushing boundaries and the investors who back them. We’re proud to have them as our sponsor. Please note, this podcast is for informational purposes and is not investment, financial, or legal advice. The views expressed are those of the speakers and do not necessarily reflect the position of SVB.
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