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Ex-Meta exec, Sequoia partner seek $1b for AI upgrades

Ravi Gupta, a partner at Sequoia Capital, and John Hegeman, a former Meta chief revenue officer, are seeking to raise at least US$1 billion for Ithaca Holdings, a holding company that plans to acquire at least one public or private firm and upgrade it with new technology, potentially including AI, people familiar with the matter said.

Sequoia is a major investor in Ithaca and the fundraising and acquisition talks are at an early stage.

Gupta stepped back from his full-time role at Sequoia in January and Hegeman, who spent more than 17 years at Meta, announced his departure as chief revenue officer in November.

The effort reflects a broader trend of investors buying traditional services businesses and injecting AI and other technology to improve operations, with firms such as General Catalyst, 8VC, and Thrive Capital backing similar plays.

🔗 Source: Bloomberg

🧠 Food for thought

Implications, context, and why it matters.

Venture capital is adopting some private equity-like tactics

  • Ithaca Holdings plans to use a “holding company” structure (a company set up to own and operate other companies) to buy a firm, instead of the usual venture capital approach of taking minority stakes across many early startups 1.
  • The plan leans on a private equity style playbook by buying a company outright or taking control, then improving performance through new technology, potentially including AI, rather than relying on financial engineering 1.
  • The draft mentions General Catalyst, 8VC, and Thrive Capital as part of a wider move toward buying services businesses and modernizing them with AI and other software, though Ithaca’s target and approach could shift since discussions remain early stage 1.

Big Tech operational experience is increasingly being paired with capital

  • Sequoia Capital partner Ravi Gupta teaming up with John Hegeman, a former Meta chief revenue officer, signals a belief that deep operating experience can sit alongside funding to drive returns 1.
  • Hegeman announced in November that he planned to leave the chief revenue officer role at Meta, and the effort fits a route where seasoned tech leaders help buy and update an established business instead of launching a new startup 1.
  • Ithaca is described as aiming to acquire at least one public or private company and add new tools, potentially including AI, while the draft’s claim that “any legacy business” can become a high-growth tech company goes further than the available details support 1.

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