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.
Bob Gillespie invests in PropTech & Real Estate, typically at Early Stage Venture and Late Stage Venture.
- Location
- Chicago, Illinois
- Typical check
- $3.8M
What does Bob Gillespie invest in?
- Investor type
- VC
- Stages
- Early Stage VentureLate Stage Venture
- Invests in
- PropTech & Real Estate
Where is Bob Gillespie based?
Bob Gillespie is based in Chicago, Illinois.
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- Startup investors in ChicagoStartup investors in the United States
How to reach Bob Gillespie
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About this profile
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Cite this page
Round Funded. "Bob Gillespie." Round Funded investor database, updated September 22, 2026.
Stable URL, it will not change: https://www.roundfunded.com/en/investor/bob-gillespie
Frequently Asked Questions
Who is Bob Gillespie?
Bob Gillespie, Managing Partner, REACH Commercial at Second Century Ventures is an active investor based in Chicago, Illinois. Bob Gillespie invests in PropTech & Real Estate, typically at Early Stage Venture and Late Stage Venture.
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.
Where is Bob Gillespie based?
Bob Gillespie is based in Chicago, Illinois.
How do founders reach investors like this?
Round Funded lists active investors with verified, professional contact details for signed-up founders. Filter by sector, stage and location, then send a personalized pitch from your own inbox.
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.
Similar investors to Bob Gillespie
Investors who share Bob Gillespie's portfolio companies, firm, city or investment focus.
- Mark BirschbachManaging Director at Second Century Ventures, Chicago
- Johan HolmbergPortfolio Manager at Second Century Ventures, Washington
- Sivan BlasenheimManaging Partner - REACH Israel at Second Century Ventures, Tel Aviv District
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- Ran LauferManaging Partner - REACH Israel at Second Century Ventures, Berlin Metropolitan Area
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