By the age of 26, Dean had his own Avro biplane and was renting it out. One customer took it out and didn't come back. The novice pilot thought having a dog fight with a friend in his rented plane (not Dean's) was good idea. One clipped the other and Dean's airplane and pilot wound up on a roof of a Williamsburg tenement. The pilot didn't survive.

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Shortly after, Dean looked for new and warmer surroundings and relocated to Miami, living in Little Havana on West Flager Street. He met Pappy Chalk and began flying for Chalk's Flying Service. In December 1937, he was one of 18 entrants in the 2nd Annual Miami-Havana Air Cruise flying from Miami to Key West then on to Havana.

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Dean not only continued to fly for "Pappy" but became a partner acquiring Grumman Gooses and operating them at Chalk's. Dean H. Franklin became known as "Mr. Grumman Amphibian" , building up a repair/conversion business and setting up many operating / leasing companies, such as Franklin Flying Service.

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• Grumman Goose N3945C (c/n B-43) to DH Franklin in May 1952 then to Franklin Flying Service.

• Grumman Goose N5538N (c/n 1086)​ to Franklin Flying Service in November 19526

• Grumman Goose N2721A (c/n B-54) to Franklin Flying Service in 1962 operated by Chalk's Flying Service as "Bimini Bonefish".

• Grumman Goose N88U (c/n B-100) to DH Franklin in January 1965 operated by Chalk's Flying Service as "Giant Tuna"

• Grumman Goose N1621A (c/n B-104) to Franklin Flying Service in July 1969 operated by Chalk's Flying Service as "Barracuda".

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In 1966 Pappy Chalk sold his airline of many years to Dean Franklin, and he made the decision to expand and add Grumman Mallards to the fleet, starting with N7356 (J-56) in 1967. 1970 saw the name from Chalk's Flying Service to Chalk's International Airlines, Inc. By 1972, Chalk's was operating 6 Mallards (J-6, J-28, J-36, J-43,J-55, J-56)

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Dean H. Franklin