Our last President with serious business chops and financial success (non-inherited division) prior to becoming President was.....Hmmm.
Could be mistaken, but I believe that would be Hoover, who was an engineer and fairly wealthy, don't know if this was from having 'serious business chops.'
That said, gotta keep in mind that for the first 100 or so years, to become president meant being born into the right circumstances, and then later it moved towards party politicians being elected president, and continues to this day.
There will soon come a time when a business person runs for senate/governor and then runs and wins the presidency, but I don't think this would necessarily be a good thing. Some of the insanely successful businessmen that I know well are batshit crazy and think that everyone should just do what they did. Life isn't generally that simple, not everyone can get into Harvard because your parents and grandparents went there (yes I know someone that honestly thinks he got in on his own merit), nor has his parents pay rent and all bills while he goes from job to job, getting fired from many of them, until a family friend needs a loan for a new business and that business takes off, enabling him to say that he is a co-founder of a successful, public company (name withheld). Yet both of these guys are actively talking about running for office saying that they can teach everyone a thing or two about 'pulling yourself up by the bootstraps (slight exaggeration on my part).'