[4] Baldwin repeated the feat on multiple occasions as a paid entertainer, netting $1500 from one dangerous jump over the water from 600 feet at Rockaway Beach in August 1887 marred by parachute difficulties.

In 1902-1903 he supervised the construction of California Eagle, based on the ideas of August Greth and financed by the American Aerial Navigation Company of San Francisco.

It utilized a De Dion-Bouton engine and paddle propeller based on marine technology so prevalent in airship design in the period.

After collaborating with Greth and John J. Montgomery in 1903–1904, Baldwin acquired sufficient knowledge to begin his own independent airship project.

[6] In June and July 1904, Baldwin built an aerodynamic cigar-shaped hydrogen-filled dirigible California Arrow, using a 7 hp (5.2 kW) Hercules motorcycle engine manufactured by Glenn H. Curtiss.

[7][8] In August 1908, after several test flights at Fort Myer, Virginia, the Army Signal Corps paid Baldwin US$10,000 for a dirigible that could be used for sustained and controlled navigation.

On the return flight, the aviator astounded the crowds by flying under both the Eads and McKinley bridges at fifty miles per hour (80.5 km/h).

He put together a company of aerial performers including J.C. "Bud" Mars and Tod Shriver in December 1910 and toured countries in Asia, making the first airplane flights in many of those locations.

At seventeen, flying a Baldwin-designed biplane, Peoli qualified at the Mineola, Long Island airfield on June 22, 1912, becoming the youngest person to gain a pilot's license.

He was commissioned a captain in the Aviation Section, U. S. Signal Corps and appointed Chief of Army Balloon Inspection and Production.