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Joining his father's firm, the [[Lewis Bear Company]], as a traveling salesman, he quickly became a full partner. He was also president of the [[San Carlos Hotel]], the [[Pensacola Crockery Company]] and the [[Ball Book & Novelty Company]].
In [[1912]] Bear built a large home in [[East Hill]], which later became known as the [[Scotland House]].<ref>"Scotland House a landmark for 80 years." ''Pensacola News Journal'', February 17, 1991.</ref>
In 1914 Bear arranged to take a "joy ride" in an early airplane and said of the experience, "A man should not try to go up in an airship if he lets anything akin to fear possess him, for it is then one is really in danger. But I will have to confess that air traveling gives one a fine sensation."<ref>"Pensacola's early aviation." ''Pensacola News Journal'', May 19, 2004.</ref>
