Lots of early presidents (and some later ones too) were plantation owners and/or farmers, so that's sort of like running a business, but I didn't look too deeply into those.

Most recently, both the Bushes were businessmen (H. and H.W. in oil, and H. in baseball).

Warren Harding published and revitalized very successfully The Marion Star newspaper

Truman and a friend had ran a haberdasher under the name Truman & Jacobson, which was initially successful but failed after the Great Depression

Woodrow Wilson set up his own law firm in Atlanta Ga but quit after less than a year.

Those are the most recent ones. I'll let you decide how successful they were for yourself