Vince McMahon’s success outside the world of professional wrestling is not very stellar. It’s safe to say that any business McMahon started that did not involve a squared circle, failed.

Alpha Entertainment LLC, the company created by McMahon which has nothing to do with WWE, was set up to “explore investment opportunities across the sports and entertainment landscapes,” according to a spokesman. The rumors of the relaunch of the XFL picked up steam earlier this week when several football-related trademarks were filed. The same spokesman said that some of that “exploring” also includes professional football.

McMahon said in the recent ESPN 30 for 30 documentary that he thought about restarting the XFL in some form. The XFL name and trademark is owned by WWE so those trademarks would have to be sold to Alpha Entertainment LLC if Vince McMahon intends to spinoff the league from WWE’s books.

But as history suggests, things never go well for non-wrestling related businesses.

In 1979, Vince and Linda McMahon purchased the Cape Cod Coliseum and the Cape Cod Buccaneers of the Atlantic Coast Hockey League. That venture only lasted until 1984.

In 1991, Vince started the WBF – World Bodybuilding Federation – but that was canned after a year. In 1992, McMahon marketed the ICOPRO bodybuilding supplements, which went bust in 1995.

In 1999, WWF New York opened in Times Square as a wrestling-themed restaurant. It was later renamed to The World but business wasn’t good and the company closed it in 2003. In the year 2000, there were plans to open the WWF Hotel & Casino in Las Vegas after the company purchased the old Debbie Reynolds Hotel. The plans were abandoned and WWE sold the property in the same year. Two years later, WWE Niagara Falls opened on the Canadian-side of the Falls as a merchandise store. That was also closed a few years later.

But the biggest loser remains the XFL, a joint venture between WWE and NBC which was created in a bid to go against the NFL. The league began in February 2001 but lasted only one season, with both NBC and WWE reporting a loss of nearly $40 million each.