The origins of the term "Jive" won't be settled by doing this. But someone motivated enough (not I) may want to contact Jive and ask them what they had in mind when they named the company. I wouldn't be surprised if they don't even know, or if the person responding to the message is not at a level to have such inside information. Probably, therefore, a fool's errand.
FWIW from the Online Etymology Dictionary
- 1928, "to deceive playfully" (v.), also "empty, misleading talk" (n.) and "a style of fast, lively jazz and dance music," Amer.Eng., from Black English, probably of African origin (cf. Wolof jev, jeu "talk about someone absent, especially in a disparaging manner"). Related: Jived; jiving. Used from 1938 for "New York City African-American slang." The adj. meaning "not acting right" is attested from 1971.
- "Jeu" (jev) game, would, seemingly, be from French colonial West Africa.
The correct (or even plausible) origins of the slang terminology of minority groups is often disputed by etymologists. See for example this note about the dubiousness of claims linking Black English slang to the Wolof language or the editorial review comments in the Amazon.com page for the Juba to Jive book.
That is in part because the literary references scholars study often appear long after the terms have lost their secret "insider" meanings or have been misinterpreted by "outsiders," sometimes with comic effect.
Maybe that's the case here. The Jive management team certainly don't look like "hep cats" but you never know.
You can argue the point intellectually as much as you choose, but I play and have played with the "cats" that actually use the word. It may have had a brief stint as a compliment (he's a real jive cat) but even that is questionable and from what I understand was often used as sarcasm for representing someone who coudn't cut it on the instrument. In 43 years of playing jazz I've never heard it used as a compliment or representing something other than a negative attribute, and I can give you hundreds, if not thousands of examples of such. The real "hip cats" of the era that used the term used it to mean a person was a bull*******, whether it be in dress, speech, manner and/or musical ability.
You mentioned Cab Calloway... who happens to be a classic example of jive.
Real musicians of that era looked down their noses at him for denigrating the music to the level of a carnival sideshow, all you have to do is look at the clips on youtube. This man was a showman, "trendy" (as in loud) dresser, an overly busy scat singer, (nonsensical verbiage) and appreciated by more white folks than black.
From the perspective of the serious musicians of the time... C.C. was a jamf.
Could it have been envy?
He made buckets of money (in the currency of the day).
On the other hand, your theory holds water inasmuch that I am white, and I (still, to this day) love Cab Calloway. I'm having a hard time thinking that anybody didn't regard him as a talented musician — serious or not. To me, he is (was) a FUN musician (sorta like Spike Jones, but a little more serious than that.)
In 43 years of playing jazz I've never heard it used as a compliment or representing something other than a negative attribute …
If you started playing jazz in the mid 1960's, I'm not surprised by this. But about a quarter of a century earlier it was not a negative attribute.
BTW, Cab Calloway was taught scat by Louis Armstrong & his band co-headlined with Duke Ellington at the Cotton Club when it was widely considered the premier jazz club on the planet. Along with Ellington, he is credited with breaking racial barriers on national radio. His band included such greats as Dizzy Gillespie, Cozy Cole, Danny Barker, & Milt Hinton. His best known song, "Minnie the Moocher," (1932) was not as lighthearted as most people think -- its subject was a "low down" drug user.
If you only know Calloway from YouTube, check out Stormy Weather (1943).