H14 family office invests in WeRoad’s $58M Series C

H14, the Milan-based family office of the younger Berlusconi children, joined the $58 million Series C round of WeRoad, an Italian group-travel company, which closed in May 2026. The round was led by Airbnb, which took a roughly 10% stake and a board seat, with H14 participating as an existing investor that had previously led WeRoad’s Series B. The financing brought WeRoad’s total capital raised to about $100 million and is earmarked for the company’s first expansion outside Europe, beginning in the United States with Austin, Texas. Founded in Milan in 2017 by Paolo De Nadai, Fabio Bin, and Erika De Santi, WeRoad organizes curated group trips for mostly younger solo travelers, matching them by age and shared interests and pairing each group with a trained coordinator. The company says it took more than 100,000 travelers on trips in 2025 and generated €130 million in revenue, up about 30% year over year. It has also built a companion product, WeMeet, for local in-person events, which it plans to use to seed demand in new US cities.

About H14: The Berlusconi family office

H14 is the investment holding of Barbara, Eleonora, and Luigi Berlusconi, the three younger children of the late Italian prime minister and media magnate Silvio Berlusconi. Based in Milan and chaired by Luigi Berlusconi, the office holds the family’s qualified stake in Fininvest, the holding company behind Italy’s MFE-MediaForEurope group, and runs a separate diversified portfolio alongside it. H14 invests across venture and growth capital, private equity, hedge funds, and public markets, with a focus on Europe and North America and a team of around twenty professionals. Its holdings have included stakes in the intralogistics group E80, the crypto platform Young Platform, the online-therapy startup Unobravo, and the asset manager Nextalia, in addition to WeRoad. The name is short for Holding Italiana Quattordicesima, or “fourteenth Italian holding.” In 2025, familyofficehub.io ranked H14 as one of the most active single-famiy offices in Europe.

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Article Source: TechCrunch, 07.07.2026