Entering into the world of venture capital has never been easy, especially as a first-time fund manager. But it’s especially daunting right now.
According to PitchBook data, firms raising their fourth fund “or later” captured a whopping 88.2% of U.S. VC fundraising dollars through the first three quarters of this year, while first-time funds captured a measly 4.5%. Just 81 first-time funds closed in the first nine months of 2026. That puts the year on track to be the worst for first-time managers in at least a decade, according to PitchBook’s estimate.
Olaf Sakkers has spent the past five years proving that difficult doesn’t mean impossible. He founded his fund RedBlue Capital in 2021 and closed its first fund with roughly $5 million in capital commitments in 2023. He has now held a first close on a second fund that he says will total at least $50 million.
Raised in South Africa, he studied anthropology at Princeton, focusing on global health and health policy, and wrote his thesis on HIV in his home country. He moved to Israel after graduating and was drafted into the Israel Defense Forces, where he says he had a desk job liaising with the U.S. military, and where he became interested in autonomous vehicles.
An introduction led to Michael Granoff, founder of the venture firm Maniv Mobility and an early backer of electric-vehicle startup Better Place. Granoff, who had money to invest, hired him on the spot, Sakkers says. Neither had been a venture investor at that point, so they built a fund “almost by accident,” learning as they went. Sakkers says he ran the investment process day to day, backing Israeli founders who were bringing cybersecurity skills into the automotive world, and later expanding to the U.S. and other markets.
Getting there has been a test of endurance as much as salesmanship, seemingly. Sakkers says that institutional limited partners, outfits like endowments and pension funds, have been the toughest to win over because his checks are small (and theirs are comparatively huge) but also because their risk model is built to “avoid getting a zero,” which is why they tend to gravitate toward established brands.
Says Sakkers, it’s akin to founders who come to be seen as “inevitable,” after they’ve previously founded another company. Meanwhile first-time founders often battle against the “gravity of perception,” meaning a more dominant brand can bend how people perceive a newer one.
His answer has been to let the results speak, but it takes time. “It’s a long-term game of building trust, demonstrating performance over time,” Sakkers says.
The first fund was a proof of concept, backed by LPs he had known for a while, including family offices. The second draws on family offices and institutions.
RedBlue writes small checks, $50,000 to $100,000, mostly joining deals led by other investors rather than leading them. That lets it do more deals and be “the last investor that they take” on by promising practical help, including introductions to lead investors like Andreessen Horowitz and Thrive Capital, and to customers. Founders expect little from VCs, in Sakker’s view, so RedBlue tries to overdeliver on the support part.
Public records support part of Sakker’s story. HappyRobot, which RedBlue backed early, raised a $150 million Series C at a $1.2 billion valuation in August. Westmag, which makes motors for drones and robots and which Sakkers backed at pre-seed alongside Nat Friedman, emerged in June with an $11 million seed led by Andreessen Horowitz. Flai, an AI startup for car dealerships, followed its 2025 seed with a $27 million Series A. And Humble Robotics, a driverless-truck startup in whose $24 million seed round RedBlue participated, announced a $51 million Series A led by Obvious Ventures earlier this month.
Sakkers argues that discipline is his edge. RedBlue publishes thesis essays, such as one on robotics, and runs on a custom database that he built with Claude Code to log relationships, meeting notes and introductions.
That lets him and his lone full-time principal, based in New York, work asynchronously. AI agents, he says, are “useless if they just have to guess,” so everything gets written down. He contrasts that with Benchmark’s more artisanal model, which he says suits a firm with a record he lacks. Long exit timelines for physical-world companies don’t worry him, either: even a $50 million to $100 million fund, he says, can sell stakes on the secondary market.
The data isn’t uniformly grim. Smaller venture capital funds between $1 million and $10 million consistently outperform larger funds of $100 million or more at the top end of net TVPI (total value to paid-in capital, which compares a fund’s total value to the money invested in it) across recent vintages tracked by the software outfit Carta.
In the meantime, Sakkers is out there knocking on doors, making introductions between disparate parties, and calling up reporters like this one to tell his story. It’s not easy to make a mark in a world where the spoils accrue to the few, but he says he never seriously considered a safer job. “Life is short, and regrets last forever,” he says.
