Bischoff had more success...by a large margin. ECW had a cult following, they were never as big a player nationally as WCW or WWE. It's debatable if they were as big in the mid 90s as TNA is today (maybe better thought of by fans, more original programming, but in terms of ratings, attendance, etc, was ECW really any bigger than TNA today ??)
In terms of creativity however I think its Heyman...by a large margin. Bischoff rose to power in WCW at a time that the company was at its lowest point. Amazingly he came this close to making Sid World Champion which probably would have set him back light years. However, going with Flair as champ started bringing back casual fans and some of the lost NWA fans, wrestling fans that were loyal to the brand and never cared for WWE. Reigniting Flair-Steamboat gave WCW another shot in the arm numbers wise, although the total wrestling audience was way down at this time (the middle of WWE's New Generation Era, probably the lowest point they've been at during Vince Jr's tenure). Having Flair back however gave Bischoff the ability to sign Hogan & Savage. Flair personally recruited Hogan to come in and made numerous concessions storyline wise to get Hogan on board for a long term deal. He was instrumental in bringing in Savage as well.
Although NWA fans never took to Hogan and he never generated the attention WCW wanted from him initially they did see another substantial rise in their numbers, now basically equal or very close to WWE. Of course this set the stage for the NWO angle and the explosion was on.
It is fair to criticize Bischoff for a lack of originality. Did he turn to Flair in 93 because he realized his value to the older audience or was it the lack of star power on his roster after firing his Sid ? I'll give him a pass on that one. Still, Bishcoff's WCW 94-96 made a lot of $$ reviving old WWE feuds (Flair-Hogan, Flair-Savage) and old NWA feuds (Sting vs Horsemen). Supposedly Bischoff had seen the NWO angle played out in New Japan before trying it in the states. Now obviously WCW was doing well enough in the ratings and money wise to convince Nash & Hall as well as Lex Luger to jump ship. Still, it was the NWO angle (apparently not an original idea) that really put the company on a fast track to its best period of success since it was still Jim Crockett Jr's NWA in the mid 80s. His four biggest angles from this period were effectively re do's of Vince, Crockett, & New Japan.
Heyman in ECW created a completely different style of pro wrestling television, taking the gritty, more adult, more violent old school NWA of the 80s and turning it up several notches. His programming was a lot of things, good and bad, and yes it created a dangerous environment for the wrestlers and enabled a lot of guys with little or no talent to become successful, at least short term, due to their ability to perform those crazy "hardcore" spots in matches. Where Bischoff succeeded with proven name talent (proven names that were almost exclusively made famous by Crockett & McMahon) re hashing previously done storylines, Heyman created something totally original, and out of nowhere created a niche market for his product. Wether it was bad business decissions, the company becoming boring because they couldnt adapt and modify their style, or some various other reason, ECW was not viable long term, but Heyman created something fresh & original.
Wrestling by it's nature is often repetitive because it's a soap opera and there are so many ways to essentially tell the same stotries over & over. Vince McMahon created Demolition as cheap copy of the more popular Road Warriors from the NWA. Verne Gagne and the AWA created The Midnight Rockers as copies of the ultra popular Rock & Rol Express (the Rockers were used much the same way in WWE). There have been stories that the "Million Dollar Man" gimmick was in part a take off on the jet flyin, wealthy, "Nature Boy" persona popularized by Ric Flair. Vince created the dynamic of the heel tag team Hart Foundation with their overbearing southern manager Jimmy Hart vs the squeakly clean kid friendly British Bulldogs to copy the success the Mid South and later the NWA had with the heel tag team Midnight Express and their overbearing southern manager Jim Cornette vs the squeaky clean teeny bopper Rock & Roll Express. Vince spent a lot of time in the 80s watching his competition and trying to replicate their successful ideas. Vince also built his company in the 80s not on the backs of home grown talent discovered and promoted by WWE but on established wrestling stars well known to large portions of the audience, guys who had perfected their trade elsewere and been very successful. Greg Valentine & Roddy Piper were top stars in the NWA before they ever signed with Vince. Ted DiBiase was one of the biggest stars in the Mid South region. Curt Henning was AWA World Champion. Randy Savage and Liz were playing a near identical act in Mid South before coming to WWE. Two of Savage's best early feuds were against Tito Santana & Ricky Steamboat, both NWA stars (Steamboat headlined at the Meadowlands vs Ric Flair a year before he signed with WWE). Shawn Michaels was a tag champ in the AWA, Harley Race was seven time NWA champion, and of course Hogan was headlining vs AWA Champ Nick Bockwinkle before he joined. Dont forget Rick Rude who cut his teeth in Texas then became "Ravishing" in the NWA before he joined WWE. These were the guys that he built the foundation of his company for two decades on, I dont even have to mention Luger, Flair, Legion of Doom, Scott Hall, Vader, all headliners elsewhere before joining WWE. Certainly Vince proved very creative in his promotional tactics, his use of TV production values and pioneering the PPV field. As a head promoter, Vince relied heavily on other people's talent and storylines to be successfull. Bischoff, who also significantly upgraded production values and appearance in WCW, was very similair in that context to Vince.
Heyman's problems have always related to his reputation of being hard to work with, a guy who knows what he thinks is right, isnt afraid to say it or defend it, and doesnt always feel the need to go along with ideas he dislikes if he doesnt want to. How much of that is overblowm hyperbole and how much is true (if any) is hard to say. Bischoff's problem was getting too close to certain talent which caused him to make bad booking decissions, not pushing through with certain storylines or burying talent that was over with crowds but not part of his "in crew". Bischoff also had a reputation for being antaganistic towards much of the talent, at least the ones who werent part of his "buddy list". Like Heyman, he was an excellent on screen character. Although Heyman was always a take off on Jim Cornette he was very good. Bischoff as an onscreen character was an original, the first full time heel boss. For many years in televised wrestling authority figures were either good guys trying to fight off heels or witless morons unwittingly duped by heels (but they were good guys, just not always real bright). Jim Crockett and Bob Giegel, Jack Tunney, WCW Commisioner Nick Bockwinkle, all portrayed as good guys. Bischoff was the first full time boss, on TV full time, as a total heel, AND HE WAS GREAT. Stripping The Steiners of the tag titles, telling referee Randy Anderson's kids that he was fired, beating up Ric Flair's son while the NWO held back his wife, as an on screen jerk few guys in the last 20 years generated the kind of heel heat EZ E did. On the mic he was one step below gold. the whole Mr McMahon character was just another in a long line of storylines and characters that Vince McMahon stole from another wrestling company. He did it great, dont get me wrong, and as a promoter he did it better than Bischoff because Vince understood in the end his character has to lose or the audience wont watch (too many times it seemed as if EZ E & NWO triumphed without any consequences, it turned off the audience). Creating the whole "Evil boss" dynamic is the one thing truly visionary that Bischoff did.
Overall, who was better depends on how you want to judge them, by what standard. Bischoff had an established company with ties to a large, loyal fan base and a national TV contract that gave him a platform to promote nationaly toe to toe vs WWE, plus he had the bankroll to sign Flair, Hogan, Savage, Nash, Hall et all. Still, you cant deny he was more sucessful longer running a company than Heyman. Heyman howver re invented the product, creating a whole niche audience, filling a void that previoulsy no one knew existed. Bishcoff essentially did in WCW what Vince McMahon did in the 80s with WWE but he wasnt a good enough business man to keep it going. Heyman created an entire business out of nothing and for awhile made it successfull. Like Bischoff bad financial management doomed him in the end. As on screen characters they were both very good but I'll give the nod to EZ E because his character was more original, and inspired the whole Mr McMahon persona that is still around today in WWE.
If you're judging just by financial success and length of success as heads of company I'd still pick Bishcoff. If you're judging more on creativity and originality it's Heyman.
