The founders of Chapter had a problem that millions of Americans would recognize. They had helped their parents navigate Medicare enrollment. The experience was confusing enough to suggest a business. To XYZ Venture Capital, that confusion contained something valuable: founders who had met the customer before they had written the pitch.
- XYZ invests in founders with firsthand knowledge of difficult markets.
- Its work includes customer introductions, hiring, product focus, and fundraising.
- Its portfolio stretches from Medicare advice to defense technology.
There is a particular kind of startup insight that arrives after an afternoon spent wrestling with a form. Someone discovers that a service people depend on is awkward, expensive, or strangely indifferent to them. The interesting question is whether the frustration is shared, whether someone will pay to fix it, and whether the founder knows how to reach that person.
XYZ has made those questions central to its business. Founded by Ross Fubini in 2017, it supplies venture capital and practical company-building help to early-stage teams. Its chosen territory includes enterprise software, fintech, insurance, and the public sector. The common thread is familiarity with work that outsiders tend to underestimate.
The customer hiding inside the paperwork
Chapter makes the thesis tangible. It combines software with in-house Medicare advisors, helping people compare coverage around their circumstances. XYZ led its $50 million Series C in May 2024. That was the total round, shared with other investors, rather than a $50 million check from XYZ alone.
The more revealing detail came earlier. Forbes reported that Fubini’s introductions brought Chapter two of its three biggest institutional partners. He also helped its chief executive prepare a fundraising deck. These are ordinary activities with unusually consequential destinations: the customer who signs, the investor who understands, the explanation that finally lands.
“Very few firms go on the whole journey with you.”
Matt Grimm, Anduril co-founder & COO
On XYZ’s website
A network with a memory
Before XYZ, Fubini was an engineer and entrepreneur. He co-founded CubeTree, acquired by SuccessFactors in 2010, and later invested at Kapor Capital and Canaan. His long relationship with Palantir supplied another kind of education: proximity to technical people selling into large organizations with complicated needs.
That became a source of founders. Anduril, the defense technology company, is the conspicuous example. But the network’s value was more specific than recognizing a famous employer on a résumé. Fubini knew people’s work, judgment, and ability to build. A reference accumulated over years can tell an investor things a polished afternoon presentation cannot.
Access still had limits. In his October 2026 We The Builders interview, Fubini described difficulty getting other firms to meet Anduril around its Series A. The obstacle was investor belief about selling products to government. Personal conviction could fund an early bet; it could not make the next financing automatic.
Keep the expert. Fix the work.
Newfront offers a quieter illustration. Its founders encountered cumbersome insurance buying, then researched the experience with finance chiefs, lawyers, and risk managers. The conclusion, as XYZ described it, was to equip brokers with better software. The professional stayed in the picture. The administrative burden was the target.
That distinction matters. An industry can look inefficient from outside while containing expertise that customers still need. Removing every intermediary is an attractive slide. Understanding which intermediary earns their place requires more patient observation. Newfront’s approach helps explain why XYZ prizes founders who have done the work themselves.
NationGraph applies a related instinct to government sales. Its platform organizes procurement information, including purchasing records, renewal timing, and signals from public meetings. XYZ announced that it led the company’s $4.5 million seed round in February 2025. The opportunity sits in making a buyer’s intentions legible before a vendor arrives too late.
Two pools of money. Two different jobs.
Venture firms have a financial structure underneath the advice. They manage investment funds for limited partners and acquire ownership interests in companies. Founders receive capital while sharing ownership and future upside. The practical cost of a particular deal depends on its negotiated terms.
In July 2024, Forbes reported that XYZ had raised $200 million for Fund IV and $125 million for its second opportunity fund. The first supports early company building. The second allows larger follow-on investments. Together, they give the firm room to stay involved as selected businesses grow. These commitments measure capital raised, not investment performance.
Knowing the problem is only the start
The team has expanded its range. In 2024, Art Clarke arrived with experience leading product and programs for Apple’s AI platforms and infrastructure. Camille Ricketts brought experience as Notion’s first marketing leader. In August 2026, XYZ added General Partner Manish Patel, whose background spans Google, product teaching, and venture investing.
Those backgrounds suggest why founders might seek XYZ alongside alternatives such as First Round or Canaan: they want help with a specific technical, commercial, or organizational decision. The sensible test is concrete. Ask which person will help, what they have done before, and what progress would look like.
For a founder evaluating that offer, diligence can work in both directions. Ask a portfolio chief executive for an example of help during a difficult quarter. Ask what happened when the company needed a hire or a customer conversation. Then compare the answer with the work your own business needs. A partner who understands distribution may be more useful than another general discussion about the size of the market. This is an editorial test readers can apply to any investor, rather than a promise about what XYZ will deliver.
The same test exposes the limits. In a Sacra interview, Fubini discussed procurement and compliance hurdles that can stop a good product reaching government buyers. A useful introduction cannot create an approved budget. An overlooked industry still needs demand, and a startup needs enough runway to survive its customer’s timetable.
The lesson readers can borrow is modest and demanding. Pick a real customer. Learn the buying process. Identify the next obstacle. Then seek the person who can help remove it. That is useful work whether or not a venture investor ever joins the meeting.