Dan Caulfield

Active Investor

Veteran Mentor & Strategic Connector

Solana Beach, California

Dan Caulfield, Veteran Mentor & Strategic Connector is an active investor based in Solana Beach, California. This profile covers what Dan Caulfield backs, at which stage, and how founders can reach out in 2026.

Mr. Dan Caulfield is an Angel Investor. Mr. Caulfield served as San Diego TCA Member at Tech Coast Angels. He is a member of the San Diego Tech Coast Angels and the Entrepreneurs Organization (EO). He is also a Board member of two new media companies: Dayak.com, Recyclers Network. He most recently worked as the CEO of Tweetphoto, a real time photo sharing service. Currently, He is the Chairman of the Board of the Hire a Hero program operated by the Armed Forces Support Foundation. Hire a Hero is a web-based community, with web 2.0 social networking and referral systems, designed to help the military community network and connect locally so that its members can find the best career opportunities and support as they reintegrate into civilian society. He was the Managing Director of Helmets to Hardhats from. Prior to founding HQ Group, LLC, He was a Senior Manager & Principal at Cap Gemini Ernst & Young. He was on the leadership team that grew DareStep, the interactive agency, and consultancy. Before joining Cap Gemini Ernst & Young, He was the founder, President, and board member of MilitaryHub.com, a business-to-consumer internet portal serving the past, present, and future members of the US Armed Forces. Before MilitaryHub.com, He founded and was the President of Hire Quality, Inc., a staffing company which specialized in high-volume placement of people transitioning from the military. The company grew quickly from the back bedroom to over ten million in sales. It spun off and sold its technology business, called Hire Technology; it was one of the first Application Service Providers (ASP) that served the Human Resources, and professional recruiting industries, as well as the US Military. Hire Quality was sold to H. Ross Perot prior to the funding of MilitaryHub.com. Prior to founding Hire Quality, Inc. He was an infantry officer in the US Marine Corps. He served as an Executive Director at Defense Mobile.

Investor type: Angel
Stages: Pre SeedSeed
Invests in: Gaming & EntertainmentMedia & Content
Location: Solana Beach, California
Typical check: $150K
Past investments: 4

Notable investments

Military Charities: Hire a Hero & Helmets to HardhatsDefense Mobile CorporationLocalStackTech Coast Angels

How to reach Dan Caulfield

Angels and operators like Dan Caulfield reply to specific, personalized notes that show real traction, not mass blasts. Build a verified list, write a note that fits their thesis, and track replies, all on Round Funded.

Frequently Asked Questions

What does Dan Caulfield invest in?

Dan Caulfield invests in Gaming & Entertainment and Media & Content, typically at Pre Seed and Seed. Match your sector and stage, then reach out with a personalized pitch.