Highmoon Capital

Founder and Managing Partner Megan O'Toole leads all investment decisions. O'Toole established the office in 2017 after her family sold its food-and-beverage manufacturing business. Will Gordon, a Partner who joined from Insight Partners in 2019, focuses on enterprise software sourcing and diligence. The office's lean structure means final approval rests with O'Toole.

Highmoon relies on an operator and founder-referral network rather than auction-based deal flow. Gordon's tenure at Insight Partners provides access to private software companies, while O'Toole's consumer-brand relationships generate opportunities in the direct-to-consumer space. The office avoids widely shopped rounds, preferring introductions from existing portfolio founders.

Highmoon is a single-family office investing exclusively the capital of Megan O'Toole's family. It does not accept outside limited partners and does not charge management fees on family-directed investments. While its check sizes and stage focus resemble a venture firm, its permanent-capital base and lack of a fund-return timeline distinguish it structurally.

Highmoon invests from late seed through Series B, occasionally participating in later growth rounds. The office writes $1 million to $5 million per initial check and reserves for follow-on across enterprise software, fintech, digital health, and consumer. It avoids pre-revenue biotech and hardware-heavy companies.

The capital originates from the sale of the O'Toole family's food-and-beverage manufacturing business, a multi-generational enterprise. Specific company names and transaction terms have not been publicly disclosed, but the exit provided the permanent-capital base that Highmoon has deployed since 2017 into technology and consumer companies.

O'Toole and Gordon take board observer seats selectively but typically do not seek full board representation. The office prefers to influence through informal founder relationships and strategic introductions, a posture suited to its concentrated, high-conviction portfolio.

Yes. Highmoon co-invests regularly with institutional venture funds, including in Robinhood and Superhuman syndicates. It operates as a value-added, non-competing capital source, which helps secure allocation in competitive founder-led rounds.