General Info
Massimiliano Squillace is an Italian serial entrepreneur and angel investor who focuses on early-stage enterprise technology in the fields of tax, legal, fraud, risk, compliance, news, media, data, finance, and insurance. He invests in amazing SaaS Italian companies at the seed stage and has a proven track record of success. Massimiliano Squillace’s investment check size ranges up to USD 18 million in Series B funding. His geographical preference includes global expansion and consolidating presence in existing territories. Previous investments include raising funds for Contents.com through Series B funding. His partnership and collaboration styles foster positivity, teamwork, and employee well-being to craft a productive workplace environment.
Location:
Country: Italy
Industries:
Investment Regions: EU
Investment Stages: pre-seed, seed
angel-individual
EU
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🤖 AI Activity Report
Status: very-active
AI Reasoning: Found evidence that Contents (founded by Massimiliano Squillace) raised Series B in January 2024. From January 2024 to Nov 1, 2025 is 22 months, which is more than 12 months-this would actually be low-active. However, Massimiliano is founder and CEO and also invested? The available data shows a Series B Jan 2024; no investments after that were found. Therefore last known investment activity tied to Contents Series B Jan 2024 (22 months ago), classifying as low-active.
Angel activity thresholds:
Low Activity – Only known angel investments more than 12 months ago.
Active – Known angel investments between the last 12 and 6 months.
Very Active – Known angel investments in the last 6 months.
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