Virgin operated in more than 40 counties with diverse, small companies.
"There was always a strategy of, 'Let's brand something and see if it works'," he said. "It didn't make a lot of sense, the brand was the crown jewel so one of the changes I've made in the past few years is to get focused on strategic use of the brand rather than trial and error as before."
He was interviewed for the role of general counsel by Branson in the back of a London cab on the way to the Brit Awards in 2004. The pair got to know each other when stuck in a traffic jam for two and a half hours.
He was promoted to group chief executive in 2011 and among his key roles is overseeing the Branson family's investments of between $5 billion and $6 billion.
Bayliss grew up in Massey, West Auckland before his family moved to Mt Albert. He was in Auckland on a flying visit yesterday after receiving an award for being Mount Albert Grammar's former student or Albertian of the year.
Now based in Geneva, he pinches himself at times.
"I think I've got one of the great jobs in the world," Bayliss says.
"You're presented with opportunities in your life it's just a case of putting yourself in a position to take those. I've been fortunate that some great opportunities have come to me and there's been some wonderful people who have opened doors for me during the years."
Bayliss trained as a lawyer at Auckland University and was on the brink of becoming a partner at Slaughter and May, one of the "magic circle" of London law firms when he changed course into the Virgin group.
Besides oversight of investments another role is managing the Virgin brand, exploiting it and ensuring it is developed in the right way around the world.
"In the future we think that brands will become self-publishing - giving the brands a personality by stories, social media, creating events."
Bayliss also oversees new business opportunities, with the emphasis on big core projects including the Virgin Galactic space venture, entry into the lifestyle hotel market and the fast-growing cruise ship sector.
Virgin Galactic was on target for launch within the next 12 months. A space port had been built in New Mexico, the mother ship and space ship were performing as they should although the launch engine was being refined to get more power out of it.
About 750 passengers, including New Zealanders, had booked for the flights. Bayliss said hundreds of millions of dollars had been spent on the decade-long project and it was still possible there could be issues that had not been foreseen.
"This is rocket science and no one has done this before."
Virgin is about to launch into the hotel market, initially in the United States. "We should have been in the hotel business a long time ago but with [airline] Virgin America finally getting to profitability and becoming a successful brand in the US that gives us the opportunity."
"If you think of lifestyle hotels many of them have great public spaces, the bars, the restaurants, food and beverage is fantastic but the rooms are neglected. These will feel like a home away from home."
Virgin is also launching into the cruise ship market, an industry where there had been compound growth of around 8 per cent for almost two decades.
Bayliss said Virgin was likely to be a large minority investor in a two-ship venture. At between 160,000 and 180,000 tonnes the vessels would be among the biggest afloat and capable of carrying around 4000 passengers.
The ships would be based in the Caribbean.
Bayliss said he speaks to Branson several times a week. "He's very fair, he's fun and he's adventurous."