Speaking at an Australian Service for Knowledge of Open Source Software (ASK-OSS) legal seminar in Sydney on Tuesday, Waugh said there is a context to "why we are doing this" in the world of software.
"I thought I'd start and say something possibly controversial," Waugh said.
"Glasnost is often regarded as meaning freedom of speech, [but] it's kind of dismantling the autocracy in Russia and disabling the power of the autocracy to dominate everything else. And Perestroika was the restructuring."
When it comes to free software, Waugh said it is really a phase of Glasnost in the technology industry.
"We are undergoing this horrible feeling of 'vomit at the back of your mouth' Perestroika restructuring," he said. "It's going to hurt a lot of companies, but what it will result in is a better freedom for everyone and better business for everyone."
Waugh said that's the context in which he likes to see why software licences are, or are not important.
"If you use the Internet you are using free software and almost 100 percent of that infrastructural free software that's all around the place is BSD licensed," he said.
"The things that tell you the names of Web sites, a lot of the e-mail stuff it's all BSD."
So if organizations want to create a piece of infrastructure that everyone will use regardless of their perspective on software development or business goals, Waugh recommends choosing a BSD-style licence, which allows the code to be embedded in other products without obligation.
"The Internet naming service called Bind is used by absolutely everyone - you'll find it in Microsoft code, open source code, you'll find it everywhere," he said.
"That's a way of getting a piece of infrastructure that you absolutely want out there to everywhere as soon as possible."
Once the public face of the Ubuntu Linux distribution, Waugh resigned from Canonical last month citing his passion for and commitment to the Gnome desktop project as the primary reason.
"So, why now? I'm excited about Ubuntu, passionate about its mission, confident in its future, and have thoroughly enjoyed being part of it from the very beginning," Waugh wrote on his blog. "But ultimately, my heart lies with another [the Gnome project], and I have to take that chance, face that risk, while my family commitments and responsibilities allow it."
Waugh will also work on his own business, Waugh Partners, an open source strategy consultancy.
On the GPL, Waugh said between 60 and 70 percent of open source projects use it and "not just because everyone is a fan of Richard Stallman".
"Once you have that kind of momentum it becomes pretty important," he said. "Every time you have a piece of software that's incompatible with yours you are duplicating effort if you want to use each other's software."
Waugh said the GPL is often described as a viral licence, but questioned how many people got a virus and decided they wanted it.
"If the GPL were viral it would affect other software and you would have no say in it - it turns out you have every say in it," he said.
Waugh also questioned the role of many licences other than the BSD, GPL, MPL (Mozilla Public Licence) calling them "annoying or irrelevant".
"The reason people create other licences is personality, you don't want to call your licence by someone else's name," he said. "The MPL has been copied with the word Mozilla changed and there are about 80 different licences. Unfortunately this means all those licences are incompatible with each other."