Dan Speakman was born and raised in Harwich. He attended Harwich schools until moving to the Dennis-Yarmouth district where he finished his schooling at D-Y in 1967. After graduating, Dan joined the Navy Seabees until 1970. In 1974 Dan earned his degree in Civil and Highway Engineering from Wentworth Institute.
From there he started working as surveyor-engineer for the Barnstable Survey Consultants, inc., before forming his own surveying and engineering firm. In 1980, Dan A. Speakman Construction was formed. He was, and still is, one of the only companies that offers Title V engineering and installations, surveying, land development, residential construction and general excavation contracting, all under one business.
In 1994, Dan added steel building repair, maintenance and construction to his services. Currently, Dan is a registered professional land surveyor, licensed construction supervisor, licensed home improvement contractor, and a licensed real estate broker.