Bob Gillespie
Managing Partner, REACH Commercial at Second Century Ventures
Chicago, Illinois
Bob Gillespie, Managing Partner, REACH Commercial at Second Century Ventures is an active investor based in Chicago, Illinois. This profile covers what Bob Gillespie backs, at which stage, and how founders can reach out in 2026.
Bob Gillespie is the Managing Partner, REACH Commercial at Second Century Ventures, a serial entrepreneur with over 25 years of experience in technology, leadership, and operations.
- Investor type
- VC
- Stages
- Early Stage VentureLate Stage Venture
- Invests in
- PropTech & Real Estate
- Location
- Chicago, Illinois
- Typical check
- $3.8M
How to reach Bob Gillespie
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About this profile
This profile is part of Round Funded, an investor database and outreach platform for founders. It covers 60,000+ active VCs, angels, family offices and accelerators with verified contacts, lets you send pitches from your own Gmail, and includes a free Data Room for your raise.
Frequently Asked Questions
What does Bob Gillespie invest in?
Bob Gillespie invests in PropTech & Real Estate, typically at Early Stage Venture and Late Stage Venture. Match your sector and stage, then reach out with a personalized pitch.
What stage does Bob Gillespie invest at?
Bob Gillespie typically invests at Early Stage Venture and Late Stage Venture. Lead with traction that fits the stage when you reach out.
What is Bob Gillespie's typical check size?
Bob Gillespie typically writes checks around $3.8M. Use it as a signal for whether your raise fits their stage.
How do I contact Bob Gillespie?
Unlock Bob Gillespie's verified email on Round Funded and send a personalized pitch. We surface only deliverable contacts so your outreach lands.
What is Round Funded?
Round Funded is an investor database and outreach platform for startup founders. It lists 60,000+ active investors with verified contacts, filtered to recent investment activity, and lets founders send personalized pitches from their own Gmail, track replies, and share a free Data Room. Round+ starts at $99 per month with a 3-day trial.