AOL, Bari Weiss’ The Free Press Showcase Old and New Guard October M&A in Media
AOL, Bari Weiss’ The Free Press Showcase Old and New Guard October M&A in Media
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AOL, Bari Weiss’ The Free Press Showcase Old and New Guard October M&A in Media

Lerer Hippeau,Tom Lowry 🕒︎ 2025-11-04

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AOL, Bari Weiss’ The Free Press Showcase Old and New Guard October M&A in Media

This report is a partnership between WrapPRO and PitchBook, the go-to financial data and software platform that provides detailed information on private and public capital markets. As the media and entertainment world anxiously awaits what could be one of the biggest acquisitions of the year, Warner Bros. Discovery, October delivered some big M&A deals for an old guard company and an upstart. Forty-year-old AOL, whose brand is still associated with the early dial-up days of the internet and one of the worst mergers in history in AOL Time Warner, sold for $1.5 billion while the Bari Weiss-founded The Free Press was snapped up by the new Paramount to redefine its news business. The top six deals for media and entertainment topped $2.3 billion in October, according to PitchBook data. AOL lives. Coming off its acquisition of Vimeo last month, Milan-based technology company Bending Spoons announced it was purchasing the online services company. Yahoo owner Apollo Global management has entered into an agreement to sell AOL. Financial terms were not disclosed, but Axios reported the deal is valued at roughly $1.5 billion. “AOL is an iconic, beloved business that’s in good health, has stood the test of time, and we believe has unexpressed potential,” said Bending Spoons co-founder CEO Luca Ferrari. “By our estimation, AOL is one of the top 10 most-used email providers in the world, with a highly retained customer base counting around eight million daily and 30 million monthly active users.” Who knew? The Free Press As anticipated, Paramount in early October acquired Bari Weiss’ right-leaning publication The Free Press and named its founder as editor-in-chief of CBS News. The $150 million move, mostly in stock, makes apparent CEO David Ellison’s desire to shift the Tiffany Network’s news division in a more conservative direction while cutting costs and reshaping programming, tasks which Weiss has taken on aggressively since the deal was first announced. Toronto-based Blue Ant Media said it was buying documentary streamer Magellan TV for $12 million. Founded in 2018 by Greg Diefenbach and Thomas Lucas, veterans of National Geographic, PBS and Discovery, MagellanTV operates a streaming video-on-demand (SVOD) service and a growing portfolio of advertising video-on-demand (AVOD) and free, ad-supported streaming television (FAST) channels. They focus on history, nature, science, space and true crime. “This acquisition of MagellanTV increases Blue Ant’s scale and adds audiences and distribution capabilities that are highly complementary to our business,” said Blue Ant CEO Michael MacMillan. October in Startup Funding October saw 38 companies raise $176 million, almost replicating September’s activity. There was strong investor interest in AI-associated ventures and a large raise for a company supporting creators. For the year so far, raises exceed $7 billion but that figure may be misleading since it was thrown off by a single raise in January of $3 billion by Infinite Reality. The pacing of venture activity since in entertainment has been fairly consistent, with investors taking a discerning approach to the sector. Here is a highlighted company for October — with a full chart of the top 15 financings below (Note: When an investor is not listed, it indicates they were not disclosed by the companies, PitchBook says.). ShopMy, a platform that provides the back-end infrastructure to help creators on commerce efforts, raised $70 million in October. The New York City-based company said the latest raise gives it a $1.5 billion valuation. The round was led by Avenir, with participation from Bain Capital Ventures, Bessemer Venture Partners and Menlo Ventures. The round is also supported by several strategic individuals and firms including Sofia Richie, Gregg Renfrew, Raissa Gerona, Alex Mondre of AGM Ventures, Aimee Song and Jacopo Moschin. “ShopMy is fundamentally a bet on authenticity and that lasting brand value comes through curation and taste over ads and algorithmic recommendations, enabling consumers to discover and buy the world’s best products,” said Harry Rein, CEO of ShopMy. ShopMy has facilitated more than $1 billion in annual sales. Wolf Games, an interactive entertainment company that uses AI tech for narrative games, raised $9 million in a new funding round. The company is backed by TV producer Dick Wolf and was founded by his son, Elliot. “Generative AI is unlocking a new frontier for entertainment,” said Elliot Wolf, who holds the title of chief creative officer. “’Wolf Games’ platform is engineered to generate living, cinematic gaming universes that create new forms of daily play with world-class storytelling at their core. Our partnership with NBCUniversal unlocks the ability to expand beloved IP through this model, bringing fans new ways of connecting with the stories that they love.” The round was led by executives Maverick Carter and Tom Werner, and artist Rashid Johnson, alongside returning investors, the elder Wolf, Jimmy Iovine and Paul Wachter. On the NBCUniversal partnership, Lindsay Vogelman, senior vice president, strategic partnerships & partner marketing at NBCUniversal, said: “We’re excited to partner with Wolf Games, an innovative company that is respectful of storytellers and has deep roots in the traditional creative and production process. Wolf Games is combining human creativity with cutting-edge AI technology to create unique gaming experiences, and we look forward to exploring how this technology can be used to build out experiences for fans of our beloved IP.” Former Meta executives Campbell Brown (above), a former NBC and CNN anchor, and Robbie Goldfarb have launched Forum AI and raised $3 million. The new company will evaluate how artificial intelligence models handle complex and nuanced topics such as politics, foreign affairs and mental health. Forum AI will tap into world-leading experts, such as former cabinet secretaries, economists, healthcare professionals and foreign policy specialists, to evaluate for bias, missing context and appropriate tone while providing clear and independent feedback that can help other companies improve reliability and trust. The round was led by Lerer Hippeau, with investment from Perplexity AI’s venture fund. How the year is looking for VC deal activity And in media …

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