Chauncey Hamilton | XYZ Venture Capital
Venture Wishlist shares ideas and themes VCs want to fund. Brought to you by Purpose Built venture studio.
Chauncey Hamilton is a General Partner at XYZ Venture Capital, an early‑stage firm with a $750+ million AUM with a core fund focused on preseed and seed plus an opportunity fund for Series B+.
Chauncey’s venture wishlist
🏭 Tech‑Enabled Services in ‘Dusty’ Industries: Apply AI + software to businesses that still run on paper or spreadsheets. Think accounting, benefits administration, etc.
🤖 Personal Automation & Agentic Workflows: Voice‑first or “pocket companions” that ingest scattered data to bring Superhuman‑level productivity to consumers.
🩺 Health‑Span: New diagnostics and delivery models that let consumers manage longevity and chronic conditions themselves, especially in personalized spaces.
⚡ Infrastructure & Hard‑Tech: Anduril‑style moonshots to rebuild U.S. infrastructure, defense, or energy with novel hardware‑software blends.
🌎 Industrial Software: Esoteric but giant markets like procurement, duty‑drawback, carbon auditing, or facility retrofits where SaaS can unlock hidden savings.
Other insights
🕵️ Primary Research Edge: Conviction comes from dozens of first‑hand customer and expert calls; this includes insight from the high density of talent and domain expertise in our own portfolio; desk research alone is a commodity.
🕰️ Timing Is the Riskiest Variable: Willing to bet on ideas slightly “early” if team & market insight are exceptional.
👩🎓 Founder‑Market Fit, Credentialed or Scrappy: Either deep insiders or relentless outsiders who earn unfair insight.
⚖️ Skepticism on Roll‑Ups: Compared to vertical SaaS, PE‑style roll‑ups are hard to execute without killer integration DNA.
🎩 Open to Weird Bets: Mining the moon, 28‑hour‑day hacks, or robot‑roofing companies are fair game if the problem is colossal, the market is there, and the founder uniquely qualified.
Full interview
Tell me about XYZ Venture Capital.
XYZ is an early-stage venture firm primarily focused on pre-seed and seed rounds, along with opportunistically small Series A investments from our core fund of $200 million. We also have an opportunity fund of $130 million, which is for Series B and beyond, mostly for existing portfolio companies to continue concentrating capital. We are very ownership-oriented, typically targeting between 10% and 20% when we invest at the early stage. We aim to be a long-term capital partner for our companies that reach escape velocity.
Did you have any particular trends or big opportunities that you wanted to talk about?
Historically, XYZ has invested in enterprise, fintech, and the public sector. We have a good amount of density and strength in both defense tech, like Anduril and Apex Space, and modern social services, like Chapter – helping expand access to more Medicare benefits. But across the board, we are drawn to overlooked industries that have not seen much technological innovation, which often leads to opportunities in tech-enabled services like Rivet for corporate taxes or Ranger for QA. We’ve also explored climate software, procurement, and AI applications. We really like niche subjects that might seem boring to others, but we find them very exciting.
That means you can get a good price if other people aren't thinking about it — it's neglected – and therefore valuations are lower? Why focus on "boring" things?
We think that focusing on less popular areas can sometimes lead to better pricing, but the pricing advantage is more about investing early rather than the industry being "boring," though they can go hand in hand. When this is the strategy, you are investing when it's just two people and a dog, as Rob Hayes, an investor I worked with at First Round, used to say. There's often better pricing, but I think some of the greatest outcomes in venture have been non-obvious. Regarding "boring" industries, we get excited about founders who are deep domain experts, obsessed with a problem that others might find mundane, but where they see a greenfield opportunity. So, our investing is very founder-centric.
I think "boring" can also be correlated with things that were established earlier and therefore might be large markets. If you can build something better in those areas, you can sell a lot.
If you can improve an existing process of something that’s considered arcane and outdated, that’s an opportunity. If someone says, “It’s always been done this way,” that signals an opportunity.
And I think "exciting" markets are often correlated with markets that don't yet exist. It’s a bet that many people will want to buy something new.
Yes, that’s true. Founders who are very vision-driven, who believe the world will change in a certain way even if it hasn’t historically, and who are betting on shifts in consumer behavior, are exciting but involve significant risk. Often, those are what Parker Conrad called “compounded startup” bets or what Josh Kopelman would call a “domino rally,” where many things have to go right for it to succeed. But those can lead to the biggest outcomes in venture every so often you just have to believe multiple things at once.
Do you avoid doing things where the industry has to be created or grown substantially?
No, we don’t. We are drawn to opportunities that feel large rather than incremental. This can range from pitches by people who want to mine the moon for resources to those building new infrastructure in different countries. For example, we were early investors in Anduril. We also invest in healthcare, especially in regulated industries with a lot of friction, complexity, and hard technical problems.
Are there any more specific themes that you’re excited about?
From a consumer perspective, I think there’s a lot of room for automation. I dislike the word “productivity,” but I think much more could be automated in daily life. I see an opportunity in synthesizing data and taking action on it, ideally with a voice interface. This might be a bit nebulous, but I envision a sort of companion in your pocket where you can tell it things that need to be done, and it collects data from different places. This might be an agentic workflow of some sort. I know there’s no investment to make more hours in the day, though my partner Ross Fubini would love a 28-hour day. I think there’s a new opportunity in personal productivity, and there’s a growing willingness from consumers to pay for things that make their lives easier. At a certain tipping point, AI will become mainstream for the mass market.
You saw Superhuman be able to charge a lot for email, which people thought they were getting for free or ad-supported before.
Exactly. And that’s still largely on the enterprise side. I don’t know the exact breakdown between consumer and enterprise for that company, but even little things like Skylight, a digital calendar for families, show potential.
I bet Skylight becomes a big business. I haven’t fully explored its functionality, but they allow you to forward your email to automatically add events to the calendar. There’s still friction, like how it figures out which class my kid is in, but we’re getting closer to that sort of automation, which is exciting.
I heard someone describe being a parent these days as being an executive assistant for your kids, and how great it would be to delegate that work.
My partner Ross’s chief of staff said yesterday, “I’m the chief of staff to Ross. I’m also chief of staff to my one-and-a-half-year-old, Zoe.” That’s accurate. Depending on how many people you’re managing, the coordination and logistics are significant. There are personal pain points where I’m excited for people to build automation, even between multi-app technologies. We see many companies doing this in enterprise, automating workflows, but less on the consumer side.
Another theme is preventative care and increased health span, one might put this in the longevity camp. Many founders are entering healthcare, thinking about care delivery, new consumer products, or new ideas in data collection, all geared toward increasing quality and length of life. That’s exciting.
And have you made investments there? Or do you want to?
I want to make investments because there’s a growing trend of people taking their health into their own hands, realizing the system won’t do it for them – along with new consumer behaviors and willingness to pay. I’ve been looking at functional medicine and new care delivery models, anything biomarker-related. I don’t have a clear thesis, but I see a shift where more people are diagnosed with autoimmune issues or other problems and are trying to navigate it on their own. New companies like Function Health or blood marker companies like Life360 show that the appetite is there.
Who’s that guy doing the biohacking – Bryan Johnson? He’s next level, but he’s pointing to broader trends in health and wellness that we are seeing being widely adopted.
I think it’s interesting how hard it is to time the market. When I was at Wired Magazine, this movement was called “the quantified self” and was a big topic for biohackers and longevity enthusiasts. That was over a decade ago, and a lot of it is just now coming to fruition.
Maybe it's timing or maybe it’s because he looks good in pictures, but he’s gotten a lot of attention. He’s saying what Ray Kurzweil wrote about 20 years ago: stay alive until you get uploaded. Everyone reacted like, “That’s weird!” Johnson is saying the same thing, and many people are reacting with, “Oh, buy me some supplements.”
Venture is often about whether there are new iterations of old ideas. Webvan led to Instacart, which succeeded because of timing.
Similar need but a very different approach.
Yes. The technology shift was mobile adoption enabling Instacart. Market timing is a big challenge in venture. Getting it wrong leads to failure or a need for enough capital to fight another day. This is all compounded by how quickly AI is moving right now. New technology unlocks emerge every day allowing for newer solutions even as existing ones are only getting off the ground.
Bill Gross from Idealab seems to think that’s the most important factor. How do you know if the timing is right?
You don’t. We are all using our own crystal balls to predict the future. My process relies heavily on primary research. It’s the only edge we have. Everyone can ask ChatGPT for information, but I love calling people in and around the market, whether they’re the target customer or industry experts. I gather anecdotal data points and do background checks on founding teams to understand why they’re exceptional. Team, idea, and market timing are all important. I’m most willing to take risks on market timing.
It sounds like you believe you’re forced to take risks, so you might as well focus on the other things. And it sounds like you believe in founder-market fit. Why is this founder the one to solve this problem?
Yes, very much so. But they don’t necessarily have to come from the industry. They need to have done the work. If they’re not from the industry, I like to see that they’ve done things like becoming an outsourced CFO for private practices to understand payments and revenue cycle management before building a new company in that space. I like to see founders get credentialed in their industry, like taking a tax or claims exam. I like to see them understand how the industry works currently and do everything they can to understand it deeply.
Does that detract from their outsider beginner’s mind approach?
Not necessarily. I think there could be two archetypes here. One is from the industry, knows it deeply, and has a theory on what to build. In that case, I like to challenge the founder with, "What have you learned that you didn’t believe before?" I want to see how quickly they are adapting and changing and challenging their own beliefs in customer discovery, and hear how they decided this was the right idea.
The other archetype is someone learning about an industry and coming in with a beginner’s mindset. In that case, I try to understand how deeply they've navigated into that market to give themselves an unfair advantage. You can bet on either archetype, but the diligence and work you do to understand whether that person is the right founder for the company are slightly different.
Are there any startup ideas you wish that you could invest in?
The last three investments I’ve made were in healthcare, energy, and education. I’ve also invested in companies selling into HR, developer tools, and tax automation. The range of what we do at XYZ is vast!
Right now, I’m spending the most time on tech-enabled services. These are traditionally service-oriented businesses where the application of AI can make things faster, cheaper, and better. I’ve been talking to many companies selling into SMBs or automating arduous tasks.
Within tech-enabled services, I’m more interested in companies building vertical solutions rather than the current venture trend of using a private equity playbook to roll up businesses and automate workflows.
I’m looking for founders in these "dusty," forgotten industries that have seen little to no innovation in the technology they use daily.
Do you think those kinds of M&A-driven businesses are VC-backable?
I'm negative on that right now. It feels easier said than done. You see many firms investing in rolling up tax firms or QA firms. I'm skeptical but open-minded to see how it plays out. Do you see anything like that happening where you’re investing?
I’ve certainly thought about those ideas, about starting various M&A-driven companies. I liked, but don't totally agree with, the piece by Slow Ventures on Growth Buyouts. They were trying to say there's the IPO path, there's the build-a-software-startup way, and then there's a third way in between. Some people talk about a third way as being like a Silicon Valley Small Business or a one-round-and-done startup. But they were talking about a third way where you buy your customer because they're too slow to adopt technology, you buy customer margin savings, and then you buy more for expansion.
They have a great example with Metropolis buying the parking garage company. The jury is out. I’m more in the software-enabled bucket plus the third way when maybe the company progresses to a later stage. But with multi-stage funds, they're taking big bets in the space of, "Here’s $20 million, go buy up a bunch of these and see how it goes." I think we’re in the early innings of seeing that strategy play out.
I’ve seen a robot roofing company. Rather than start by selling robots to roofing companies, they’re selling directly to homeowners. It’s vertically integrated. I understand if you have such adoption problems with your customers and a genuinely better solution, not just reducing margin but increasing margin and reducing costs, why you might choose to vertically integrate. It’s a different choice, though, if you’re going to be M&A-driven, which is a specific skill set And if you don’t have much experience with M&A, it can easily backfire.
That’s the awareness piece in backing different founder archetypes: Is this person curious, a lifelong learner, and do they know they don’t yet understand how to do M&A? Are they able to hire and attract someone who can work with them on that?
It goes back to the founder archetype — digging deeply into who that person is, their motivation, and their humility and awareness regarding the skills they need to acquire or develop. That’s yet another reason I take a very founder-centric approach.
Any other things you want to mention that we haven’t touched on?
One thing we didn’t highlight as much is that we’re definitely open-minded to “weird and wacky” ideas. We’re very open to someone trying to solve a really big problem, like, “How do we build more infrastructure in the US?” And then exploring what technology needs to be built, both bits and atoms, to accomplish that.