Bob Gillespie in

Bob Gillespie

Visionary · DISC type Ds
Managing Partner, REACH Commercial at Second Century Ventures
📍 Dallas-Fort Worth Metroplex, United States

Bob is a serial entrepreneur and the Managing Partner of REACH Commercial at Second Century Ventures, a venture capital fund dedicated to real estate technology. With over 25 years of experience, he focuses on building great teams and has advised over 200 startups. He holds an MBA from The University of Chicago Booth School of Business.

While his public profile centers on his extensive career in technology and venture capital, he is deeply engaged in the startup community. He frequently shares his expertise on equity structures, funding, and governance to help founders navigate complex financial decisions, demonstrating a passion for giving back to the entrepreneurial ecosystem.

Companies Bob has founded have achieved an enterprise value in the several billions, raising hundreds of millions in venture funding.

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Experience
35 Years
Current Role
Managing Partner, REACH Commercial
Location
Dallas-Fort Worth Metroplex, United States
Personality Overview

How Bob shows up

Objective Evaluator
Direct & Assertive
Risk Tolerant

Reading between the lines and seeing beyond your words comes naturally to them. They are very professional in their approach and can weigh multiple perspectives together. They might take some time to make their mind up but once they do, they don't change it easily.

Priorities

Topics Bob cares about

PropTech Innovation
As Managing Partner at REACH Commercial, he is actively investing in and scaling the most promising new technology companies in the real estate sector.
Startup Mentorship
He has worked extensively with over 200 companies in accelerator programs, providing mentorship and network connections to drive growth and secure funding.
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Career

Work history

1-2019
Managing Partner, REACH Commercial
Second Century Ventures
1-2012
Strategic Advisor
Cap Table Expert
3-2013 - 8-2025
Board Member
Conference Software Solutions, Inc
2-2016 - 12-2018
Executive Director
Elmspring Accelerator
3-2015 - 1-2016
Partner
Anka Capital Management, LLC
In the press

Media appearances

Second Century Ventures Announces 9 Companies for 2025 REACH Commercial Scale-Up Program. Featured in GlobeNewswire
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Education
2008 - 2011
MBA
The University of Chicago Booth School of Business
1986 - 1990
BA
Knox College
Social presence
in
Behavioral profile

DISC profile (public)

D

Dominance (D)

Dominance (D) reflects how goal and task oriented a person is, and their ability to accomplish results irrespective of how demanding the circumstances might be. Those scoring high tend to be motivated by winning, competition, and success.

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