From product manager to COO to VC - the long way around, on purpose.
Steve Schultz spent a decade building financial products before he ever thought about investing in them.
He ran Yahoo Finance's product organization when it was the default place Americans went to check a stock price. Then he joined a startup called Check and turned it into one of the fastest-growing mobile financial services of its era - 10 million users, a billion dollars in payment volume, and a $360 million exit to Intuit. After that, he went inside Amazon Web Services and built their partnership with Y Combinator, sitting across from hundreds of early-stage founders and watching, close up, which ones actually had it.
By the time Steve Schultz walked into Diagram as a General Partner in 2023, he had done the thing most investors only study. He has shipped products, run operations, negotiated enterprise deals, and watched a startup get acquired. Now he backs founders doing the same, from a $100 million fund focused on the intersection of fintech, web3, and climate technology.
Diagram is based in Montreal but Schultz is planted in Menlo Park - which is precisely the point. He is the firm's live wire into Silicon Valley, the person who can call a YC founder and have them pick up the phone.
The investors founders trust are the ones who have shipped something, broken something, and fixed it. The rest are just reading the same pitch decks.- The operating thesis behind Steve Schultz's approach to early-stage investing
There is a specific kind of investor who has never had to file a quarterly report, negotiate a bank partnership, or explain to a board why a product launch slipped three months. Steve Schultz is not that investor.
He spent the dot-com era learning enterprise sales at Epiphany. He spent five years at Yahoo Finance understanding what financial data products need to do to survive at internet scale. He spent four years at Check understanding what it takes to move money for ordinary people - bill payment, paycheck tracking, the unsexy work of financial infrastructure.
When Intuit paid $360 million for Check in 2014, it validated more than a product. It validated an approach to market - direct consumer acquisition, deep bank partnerships, a payments stack built for real-world use. Schultz had a hand in all of it.
Then he went to AWS and watched it all over again, from the outside. The YC partnership put him in the room with the next generation of fintech founders - giving him a comparative lens that few investors get to develop.
Diagram is not a typical VC. It started as a venture builder in Montreal in 2016 - a studio that creates companies from scratch, validates ideas before funding them, and then writes the check. By the time Schultz joined, Diagram had evolved into a hybrid: part builder, part traditional early-stage investor, with a specific thesis around fintech, web3, and climate technology.
Fund III - the raise Schultz joined - closed above $100 million and marked a deliberate geographic expansion. Two new US-based partners, including Schultz, were brought in to extend Diagram's reach into Silicon Valley and the broader American startup ecosystem. The logic is straightforward: the best fintech founders are building everywhere, but the networks that accelerate them are concentrated in California.
Schultz's role is to be that bridge. His relationships from Yahoo Finance, Check, AWS, and F-Prime cover a significant swath of fintech - from payments infrastructure to lending technology to capital markets software. For a Diagram portfolio company trying to land a bank partnership or negotiate an enterprise deal, having a GP who has done it before is a material advantage.
The things that got Schultz where he is - curiosity about financial systems, comfort with operational complexity, willingness to stay in a role through the hard parts - were not formed in business school. They were formed at companies that were building something real under real pressure.
Epiphany was an enterprise software company that tried to solve marketing analytics before the tools existed to do it elegantly. Working there in the early 2000s meant learning product management in an environment where "data-driven" was an aspiration, not a default. It also meant watching a category get built from scratch, which is the kind of experience that does not come from case studies.
Yahoo Finance was a different education. It was already at scale when Schultz arrived - tens of millions of users, real advertising revenue, the center of attention for every public company's investor relations team. Running product there meant making decisions that affected how ordinary Americans understood their own financial lives. Portfolio trackers, market data, earnings calendars: Schultz was responsible for the systems that translated Wall Street's complexity into something a retail investor could actually use.
Check was the pivot that defines how Schultz thinks about fintech today. Joining as COO from inception meant owning everything that was not purely engineering: product vision, bank partnerships, consumer acquisition, enterprise deals, regulatory conversations. By the time Check crossed $1 billion in payment volume and 10 million users, it was no longer a startup in the traditional sense - it was a platform with real financial infrastructure underneath it. Intuit saw that. The $360 million acquisition in 2014 was a validation of infrastructure, not just growth metrics.
AWS was the phase that completed the picture. Inside one of the world's most important cloud providers, Schultz built and managed the partnership with Y Combinator - which meant sitting across from hundreds of early-stage founders and watching which ones had the specific combination of technical credibility, market insight, and sheer stubbornness that eventually becomes a real company. It is, in retrospect, the best possible preparation for writing early-stage investment checks.
Schultz started his career at Epiphany during the dot-com era - a company that tried to solve marketing analytics before the infrastructure existed to do it. It gave him a long view of technology cycles that most fintech investors simply do not have.
He ran Yahoo Finance when it was the default place Americans went to look up a stock price - long before Robinhood, Bloomberg Terminal for consumers, or mobile-first brokerage apps reshaped financial media entirely.
The Check acquisition rebranded the app to Mint Bills under Intuit's umbrella. Schultz navigated the post-acquisition integration from the inside - an education in what happens to a fast-growth startup after the deal closes.
His AWS role gave him a direct line to hundreds of Y Combinator founders - a rare vantage point that shaped how he evaluates early-stage teams. Most investors read about YC companies; Schultz worked with them as they were building.
Diagram was founded in Montreal in 2016 - a year before most American investors started paying attention to the Canadian startup ecosystem. Schultz joined a firm that has been building financial technology companies for nearly a decade.
His full California academic pedigree - Economics at UC Davis, MBA at Haas/Berkeley - mirrors the academic arc of many operators who eventually cross into venture. What's unusual is how long Schultz stayed on the operating side before making the jump.