General Info
Rob Bailey, the CEO of DataSift, focuses on investing in distributed system (blockchain) companies targeting the enterprise sector. His previous investments include BackboneAI, where he served as CEO & Founder, and Kustomer, which was acquired by Facebook for $1 billion. Rob has a track record of successful investments, such as SimpleGeo, acquired by Urban Airship, and DataSift, acquired by Meltwater. He is based in New York City and has a strong preference for investing in this region. Rob’s investment check size varies depending on the opportunity.
Location:
Country: United States of America
Industries:
Investment Regions:
Investment Stages: pre-seed, seed
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🤖 AI Activity Report
Status: very-active
AI Reasoning: Found a public investment/participation event: CrewAI had funding announcements on Oct 22, 2024 (Boldstart and Series A led by Insight Partners) where Rob Bailey is co-founder and involved with the company. That investment event is 10+ months before the reference date, which is within 12 months? Wait: From Oct 22, 2024 to Nov 1, 2025 is 375 days – more than 12 months. But additionally Rob was active in 2024; however more recent evidence: LinkedIn post Jan 8, 2025 referencing investor activity indicates involvement in 2025 which is within 10 months before Nov 1, 2025? Jan 8, 2025 to Nov 1, 2025 is ~298 days (~9.8 months) – still between 6 and 12 months, which maps to active. However the CrewAI Series A Oct 22, 2024 is >12 months. The latest found activity is LinkedIn post Jan 8, 2025 mentioning investors; no direct investment by Rob then. The most recent clear investment participation is Oct 22, 2024. That is 375 days earlier -> more than 12 months -> 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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