Connect with Haley

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Meet Haley

Key Quotes

Original Responses (Lightly Edited for Clarity and Flow)

Background and Personal Journey

What experiences in your life or career have had the greatest influence on how you approach investing today?
“At pre-seed, we invest in ideas, but we’re really investing in people. Thirty percent of the time after we write a first check, a team pivots. Maybe the market is too competitive, slow-moving, or small. So how do you choose who to back? It’s something I’ve thought about throughout my career, from growing teams at Apple to scaling a content agency.

What I’ve seen time and again is that talented people who are given a shot—regardless of whether they have a prominent school or company logo on their LinkedIn—outperform. I feel really lucky that throughout my journey, I’ve had people look beyond logos to see me, and I get to pay that forward. My path to VC is more of a career jungle gym than a ladder. When I wanted to escape retail management, Walter Chen, a serial entrepreneur and prolific angel investor, took a chance on me.

Can we find non-obvious founders who can quickly level up if they’re given not just capital, but also knowledge and networks? Ideally, Hustle Fund can be a platform for the discovery of great founders who look like anyone and come from anywhere, similar to the Mickey Mouse Club in the late ’80s and early ’90s.

When Matt Casella scouted for the Mickey Mouse Club, he met 85,000 kids over six years. And while he attracted rising stars like Justin Timberlake, he also saw something in Britney Spears, Christina Aguilera, and Ryan Gosling that others hadn’t. So I care less about résumés and more about energy, effort, and first-principles thinking.”

Who or what has shaped your worldview the most, and how does that influence your approach to decision-making?
“I’m lucky that my family is full of independent thinkers. My dad left corporate banking to build his own business almost two decades ago. My mom travels the world supporting public health initiatives. My sister pursued music and community-building instead of school, and my brother is a solopreneur delivering keynotes on creative thinking to executives. I have great examples around me of breaking free from ‘traditional’ paths and shaping my own worldview. But it wasn’t until after I’d had my son that I really began to think deeply about it.

Several years ago, I read Finite and Infinite Games by James Carse during a very reflective period. I worked with an executive coach to understand the patterns and habits that got me where I was but were also holding me back. The book opens: ‘There are at least two kinds of games. One could be called finite, the other infinite. A finite game is played to win, an infinite game for the purpose of continuing the play.’ It helped me shift away from a scarcity mindset and crystallized my desire to play positive-sum, infinite games.

Someone recently told me they filter their decisions through their 5-year-old and 80-year-old selves, and that’s essentially what Finite and Infinite Games gifted me—the space to view decisions on a super long-term basis.”

What’s the best advice you’ve ever received, and how has it shaped your journey in venture capital?
“Before I started working in VC, I participated in a program called the Decade Game. Over a few weeks, you set goals across your most important life pillars: self, loved ones, work, learning, and community contribution.

Carolyn, formerly an EY partner who’s been playing the game herself for more than 50 years, says: ‘You can’t get there from here, but you can get here from there.’ While we looked at vision boards 10 years into the future, the focus was on the 1% progress we could make each day. It’s these small steps that compound over weeks, months, and years. Overnight success stories really come from consistent execution.

In startups, strategy might be 5% of the job. We romanticize working ‘on’ the business, but especially in the early days, so much is just waking up day after day and getting after it. Set the long-term vision and then show up.”

Philosophy and Insights

How would you describe your investment philosophy in a single sentence, and what led you to this approach?
“When I started angel investing, my thesis was to invest in founders from and/or supporting underserved markets. Initially, this came from looking at the numbers and seeing a huge opportunity to close a funding gap.

A lot has changed in the world since I started angel investing in summer 2020. There is less receptivity to an explicit focus on underrepresented founders and people in general. In the last few weeks, we’ve seen unfortunate pullbacks on DEI programs. Still, the opportunity remains. What I’ve found is that the underserved markets I’m excited about attract founders with lived experiences who often happen to be underrepresented.

Companies building for underserved markets tend to have fantastic dynamics—lower CAC, higher LTV, reasonable valuations, and founders who are more missionary than mercenary. Fundraising for these long-tail markets is often challenging because VCs question the TAM, so these ideas attract capital-efficient, lean teams.

A big part of my desire to join Hustle Fund was the alignment with the ethos that great founders look like anyone and come from anywhere, and a focus on founders who are great at execution. I can’t say I’ve met 85,000 teams yet on my Mickey Mouse Club journey, but I’ve looked at more than 10,000 companies at this point, and my deal taste increasingly leans toward underserved or emerging markets. I’ve gotten excited about companies building for comedians, campgrounds, equestrian show organizers, and franchising—companies that see much bigger opportunities in the markets they’re serving.”

What principles or values do you prioritize when working with founders and early-stage companies?
“I look for founders who can manage vision and purpose to attract customers, capital, and talent, while balancing long-term thinking with high-quality and high-velocity short-term execution. These are people who are data-driven, experimental, and view failure as part of progress. Founders with previous startup experience often have a realistic grasp of resource constraints and can weather the inevitable ups and downs.

Beyond that, self-awareness is huge—specifically knowing your zone of genius and where you need help. This should be coupled with first-principles thinking about how to source not just talent but also advice. Vinod Khosla said that one of the most important things founders do is figure out who to take advice from. A big part of that is understanding why people give the advice they give, and being very thoughtful about who you listen to along the journey.”

If you could design the perfect pitch from a founder, what would it look like—and why?
“A great pitch at the early stages shows the big opportunity, educates by sharing a surprising insight, demonstrates early momentum, and highlights a team’s right to win. Ideally, you can cover team, problem, market, solution, and traction in no more than 10 slides. I love a deck with one sentence per slide that, read together, feels like a complete elevator pitch—too much text can obscure the key points.

Often I recommend starting with a six-page memo and progressively distilling it down. At Animalz, we worked with startups using McKinsey’s MECE framework to clarify thinking. While I love reading a detailed thesis, the deck should be more top-of-funnel to show clear thinking and get people excited.

The approach also depends on your product’s market. If you’re building for the future, share data on market growth and any technological, regulatory, or cultural shifts that offer tailwinds. If you’re entering a competitive market, address the elephant in the room early. Explain why you’re 10x better and how you’ll cut through the noise without breaking the bank.”

How do you personally measure success in venture capital beyond financial returns?
“When I did the Decade Game, my ten-year goal was to work on what I want, where I want, with whom I want. VC has already unlocked that for me. Every day, I meet the smartest, most passionate people building the future, chasing huge visions despite the risks.

Beyond incredible founders, I get to work with angels and VCs I respect and trust. Melissa Bradley of New Majority Ventures in DC often says VC is a team sport. Nasir Qadree at Zeal Capital emphasizes community. I think success in VC is about building a huge team and community of people working together to help companies survive, thrive, and create life-changing outcomes for customers, founders, LPs, and investors.”

Trends and Future Vision

Which emerging trends or technologies excite you most, and why do you believe they will shape the next era of innovation?
“I joined Hustle Fund in September 2022, just a couple of months before ChatGPT was released. Since then, our AI-focused inbound deal flow doubled—from 16% to 30%. There’s a lot of investment in AI, but I’m not focused on AI companies per se, because it’s extremely competitive. Instead, I’m interested in AI-first companies that reimagine legacy service businesses with AI workflows and SaaS-like margins, building an operational playbook that gives them a competitive advantage in process power.

At Hustle Fund, we invest hilariously early, so while VCs usually focus on market risk, we get in early enough at valuations that don’t require every company to become a unicorn for us to see a path to 100x outcomes. I’m often drawn to companies where the main factor is execution risk, betting on my ability to identify the best operators.

With the rise of AI agents, humans will spend less time interacting with software. I expect more consolidation over time. Initially, we might see middleware that integrates point solutions, but longer term, software will be increasingly commoditized. Platforms will build more end-to-end capabilities to reduce software spend and increase stickiness. We lose efficiency with context-switching across dozens of apps. A vertical approach is likely easiest, because startups can build purpose-built solutions for specific industry workflows.

Lastly, there are many consumer use cases that AI makes possible in finance, health, productivity, and more. But consumer can be tough—CAC:LTV is challenging even for companies like Netflix or Spotify. So I’m spending time on teams that use emerging tech for consumer needs but have found a disruptive business model. One approach is partnering with incentive-aligned businesses that can subsidize the cost, making the product a no-brainer for users.”

If you could improve one aspect of the venture capital ecosystem, what would it be, and why?
“One reason I love pre-seed is that it’s largely a team sport. As a $150k check writer, we partner with amazing angels and VCs to help founders get to the next leg of the relay race. At this stage, there’s an understanding that we win together, and people are open to sharing deals. There aren’t many sharp elbows.

That said, VC is still an insider’s club, with decisions often based on founder work experience, school pedigree, and upbringing. Pattern matching. There’s a great Endeavor study showing only one-third of unicorn founders got their bachelor’s degree at an elite university, and only 20% worked for an elite employer. As we become more data-driven, I’m hopeful that the next generation of VCs will evolve beyond this insider’s club mentality.”

What is the single most significant challenge that early-stage founders face today, and how can VCs help address it?
“Challenges vary by stage. When we meet founders, they often think their #1 challenge is fundraising, and that’s definitely tougher in today’s market with less LP liquidity. But if you look deeper, their real challenge is customer or talent acquisition. Many VCs need to see some form of market validation—whether customer discovery or LOIs/contracts. So we spend a lot of time helping founders with customer acquisition. Sometimes we’ll even pause a raise to build the business more, so the path from intro to investment improves.

Talent acquisition is another big challenge, especially for solo founders who lack technical expertise in highly competitive markets. I’ve spent a lot of time on this recently.

Over the last decade, venture-backed startups have become en vogue, but it’s getting cheaper to start and sustain a business. We love super-lean teams planning to raise once or twice to reach breakeven. We’re also seeing bootstrapped teams that have grown substantially on their own and are now looking for just enough capital to accelerate. In a world where capital isn’t the only concern, there’s more need for VCs to support founders with knowledge and networks—especially for customer and talent acquisition.”