Bob Gillespie
Angel Investor @ REACH
Chicago, United States
Bob Gillespie is a seed investor at REACH in Chicago focused on Software and Real Estate. Bob Gillespie was the Co-Founder, Chairman, and CEO of InContext Solutions. He is currently the Executive Director at Second Century Ventures.
- Total investments:
- 29
- Last investment:
- Lead investor:
- 3%
Last updated:
For AI agents: llms.txt
Industries Bob Gillespie invests in
Stages Bob Gillespie invests in
Countries Bob Gillespie invests in
Contacts
| Type | Contact | Validation |
|---|---|---|
| Work email | ||
| Personal email | ||
| Work phone | ||
| Personal phone | ||
| Socials |
Investment Focus
Industry
- Software 12 (41%)
- Real Estate 11 (38%)
- Commercial Real Estate 8 (28%)
- FinTech 5 (17%)
- SaaS 4 (14%)
Stage
- Seed 16 (55%)
- Venture - Series Unknown 9 (31%)
- Series A 2 (7%)
- Pre-Seed 1 (3%)
- Funding Round 1 (3%)
Country
- United States 28 (97%)
- Estonia 1 (3%)
Investments
| Company | Description | Round | Links |
|---|---|---|---|
| Prophia is a data and document intelligence platform designed for the commercial real estate industry. The company's mission is to be the trusted data partner for commercial property data. Our vision is to leverage AI to provide the commercial real estate ecosystem with a unified data intelligence platform, powered by documents, that providesdata transparency, reduces transactional friction, and lower transactional costs associated with buying, selling, financing and leasing commercial properties. | Seed / Jul 29, 2024 | ||
| Urban vision factory - turning cameras into sensors using AI-sight | $2.1M / Seed / Nov 10, 2023 | ||
| Dwellwell Analytics is a technology-driven property maintenance provider that develops integrated sensors for residential buildings. It utilizes a sensor network and whole-home analysis to provide a view of the operation and performance of a portfolio of single-family rental homes or multi-family buildings. | Venture - Series Unknown / Apr 11, 2023 | ||
| RealGrader is a platform empowering professionals to measure, manage and maximize their digital identity on Google, Social Media & Professional Marketing Sites. We help professionals move from agents to influencers with our services: patent pending INSTACARD - The Digital Card, profiles setup and optimization, and our done for you social mediamarketing team. We serve over 70,000 users and have over 5500 paying monthly subscribers. | Venture - Series Unknown / Apr 11, 2023 | ||
| Plus develops an asset management and trading platform that allows users to enhance data, manage portfolios, and transact with unparalleled ease. Its Smart Loan technology and contemporary platform architecture enable smoother operational interactions for all industry participants. | Seed / Apr 11, 2023 | ||
| A closing platform built for top agents that beautifully markets their brand and wins more business. | Seed / Apr 11, 2023 | ||
| Rockport is a Commercial Real Estate lending management Software as a Service (SaaS) system that allows for complete organization and analysis of clients' internal information related to CRE lending: analytic tools, a centralized information repository for deal documents, ad hoc reporting, excel integrations, asset-specific chart of accounts,full disaster recovery/security protocols, user-defined fields for custom integrations into a client's workflow and a full audit trail for every field in the system for compliance concerns | Venture - Series Unknown / Apr 11, 2023 | ||
| APM Help is a team of AppFolio & Propertyware experts providing On Demand Consulting, Daily Bank Reconciliations, & Full-time Bookkeeping. | Seed / Apr 11, 2023 | ||
| BlueStreak offers commercial Internet of Things framework. It is at the epicenter of data from sensors, devices, networks, and software, which work together to offer useful, actionable data and automate important operations in retail, hotel, entertainment, health, fitness, real estate, and other commercial places. | Venture - Series Unknown / Apr 11, 2023 | ||
| Fortress is a core property management software. We provide real-time transparency into property performance with a user-friendly interface. Fortress revolutionizes property management with its real-time data & KPIs. Experience a new level of success managing leads, applications, renewals, move-ins/move-outs, final account statements,delinquency notices, lease expirations, tenant screenings, work orders and more. Learn more about Fortress by visiting www.FortressTech.io. | Venture - Series Unknown / Apr 11, 2023 | ||
| See all 29 investments → | |||
Co-Investors
About REACH
REACH is a strategic scale-up program owned and operated by Second Century Ventures, the investment arm of the National Association of Realtors®. Founded in 2013, REACH is focused on helping technology companies connect with one of the largest industries in the world: real estate. By helping companies innovate in the industry, they help hundredsof thousands of small businesses, millions of REALTORS®, and consumers, and the economy as a whole.REACH offers its member companies more than 350 mentors from top real estate companies as well as direct access to NAR's membership to become customers and partners. REACH works closely with other accelerators and incubators and welcomes graduates of Excelerate, TechStars, DreamIt, and YCombinator to apply to NAR REACH for targeted outreach, ongoing coaching, and support.REACH accepts companies at all stages of investment – from an early idea to a standing company with revenues and investors.REACH is an accelerator with a focus on technology companies in real estate and adjacent industries.
REACH Contacts
| Name | Phone | Socials | |
|---|---|---|---|
Ashley Stinton
Senior Director, Marketing & Communication
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Bob Goldberg
Founder
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Carlos Rousseau
Managing Partner
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Dale Stinton
Founder
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Dave Garland
Managing Partner
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FAQ
What does Bob Gillespie invest in?
Bob Gillespie invests primarily in Software, Real Estate and Commercial Real Estate startups, most often at Seed and Venture - Series Unknown stage. Most of the 29 investments tracked by Shizune back companies in United States. The Investment Focus section breaks down every industry, stage and country in the portfolio.
How do I contact Bob Gillespie?
Public channels for Bob Gillespie include LinkedIn. For a verified work email and phone number, create a free Shizune account — contact data is searched across 20+ sources and validated before delivery, so your outreach lands in the right inbox.
When did Bob Gillespie last invest?
The most recent investment recorded for Bob Gillespie closed in Jul 2024. Shizune tracks 29 investments in total for this profile, including round sizes, stages and portfolio companies, all sourced from confirmed public funding rounds and refreshed monthly.
Is Shizune's investor data accurate?
Yes — every stat on this profile is calculated from confirmed public funding rounds monitored across hundreds of sources since 2020. This profile was last refreshed in Aug 2026 and is updated monthly. Spotted something off? Use the “Suggest an edit” link near the top of the page.
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