Cal Simmons
InvestorPartner at Early Light Ventures · Washington, DC Chair at TIGER 21
Washington, DC Metro area
Writes $100K – $1M checks · typically $400K
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About
Cal Simmons is an early-stage angel investor focused primarily on the Washington, DC Metro area, with more than 50 portfolio companies. Before investing, he built two travel businesses — Cal Simmons Travel, a 13-branch agency serving corporate accounts such as National Geographic and The Discovery Channel, and Five Star Alliance, an online agency marketing luxury hotels, both of which he grew and sold. He has chaired the Washington, D.C. chapter of Tiger 21 for a decade and previously served 12 years as chairman of the Virginia Tourism Corporation. He is also the coauthor, with John May, of a book on venture capital for entrepreneurs.
Beyond investing
- Founded
- Founded, grew, and sold Cal Simmons Travel, a 13-branch travel agency with corporate accounts including National Geographic, The Discovery Channel, The Advisory Board, and Friedman Billings Ramsey. Founded, grew, and sold Five Star Alliance, an online travel agency marketing luxury hotels, with a successful exit to Questex Media and a private equity firm.
- Boards
- Served 12 years as chairman of the Virginia Tourism Corporation.
- Communities
- Has chaired the Washington, D.C. chapter of Tiger 21 for a decade.
- Hobbies
- Has traveled to over 70 countries.
- More
- Coauthored a book on venture capital with John May, praised by Motley Fool cofounder David Gardner.
From Cal's own website — common ground for a warm intro.
Experience
- Tiger 21Washington, DC Chaircurrent2010 — presentWashington, DC
- The Five Star AllianceFoundercurrent2004 — present
- Congressional BankBoard Membercurrent2003 — present
- Five Guys EnterprisesFranchiseecurrent2009 — present
- Industry DiveInvestorcurrent2011 — present
- Big League AdvanceInvestorcurrent2016 — present
- EVERFIInvestorcurrent2014 — present
- Zachary Piper SolutionsInvestorcurrent2014 — present
- Zignal LabsInvestorcurrent2012 — present
- XAPPmediaInvestorcurrent2014 — present
- RevinateInvestorcurrent2009 — present
- Clowder®Investorcurrent2013 — present
- GoingPlaces AppFounder/Publishercurrent2016 — presentAlexandria, VA
- Travel Red BookFounder, CEOcurrent2014 — presentAlexandria, VA
- Blue Cotton Tech ServicesOwner and Chairmancurrent2003 — present
- Travel OnionPublishercurrent2009 — present
- The Dinner ClubsManagercurrent1998 — present
- Virginia Tourism CorporationChairman2004 — 2014
- Outtask Inc.Board Member2003 — 2008
- Cal Simmons TravelFounder1976 — 1997
Skills & more
+12 more
Mergers & AcquisitionsMarketing StrategyBloggingSEOOnline MarketingDigital StrategyLead GenerationDigital MarketingVenture CapitalSmall BusinessE-commerceSEMFrom Cal's professional profile.
Investments
Led
Five Star Alliance
Investor
Big League AdvancePointsHoundReelGenieZignal Labs
Sources: the investor's own website · curated public sources.
Podcasts & interviews
featuring Cal SimmonsCal's Meeting
Cal Simmons
Cal Simmons at CoE2010 - Every business needs an angel
Wamda

Talk / interview
youtube.com
Colleagues at Early Light Ventures
Network5
Investors connected to Cal in public investor directories — a warm-intro map.
Frequently asked questions
- Who is Cal Simmons?
- Cal Simmons is an early-stage angel investor focused primarily on the Washington, DC Metro area, with more than 50 portfolio companies. Before investing, he built two travel businesses — Cal Simmons Travel, a 13-branch agency serving corporate accounts such as National Geographic and The Discovery Channel, and Five Star Alliance, an online agency marketing luxury hotels, both of which he grew and sold. He has chaired the Washington, D.C. chapter of Tiger 21 for a decade and previously served 12 years as chairman of the Virginia Tourism Corporation. He is also the coauthor, with John May, of a book on venture capital for entrepreneurs.
- Where does Cal Simmons work?
- Cal Simmons is Partner at Early Light Ventures.
- What check size does Cal Simmons write?
- Cal Simmons typically writes checks of $100K – $1M.
- What companies has Cal Simmons invested in?
- Investments tracked here include Five Star Alliance, Big League Advance, PointsHound, ReelGenie, Zignal Labs.
- Where did Cal Simmons go to school?
- Cal Simmons studied at The University of Kansas (BS, Journalism); George Mason High School.
- What podcasts and interviews feature Cal Simmons?
- Tracked appearances include "Cal's Meeting", "Cal Simmons at CoE2010 - Every business needs an angel", "Talk / interview".
- Does Cal Simmons lead rounds?
- Yes — Cal Simmons has led 1 tracked investment.
Same school
Also attended The University of Kansas180
+ 174 more
Also attended George Mason High School1
Shared employers
Also worked at Industry Dive3
Also worked at Big League Advance3
Also worked at EVERFI17
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