Nearly a decade later, YBR has announced its transitioning to a franchise model - a process that will result in layoffs among management-level staff, as the company consolidates following the acquisition four other businesses.
And while Mark may have built his profile by exclaiming 'you're fired' on the reality TV program, The Apprentice, letting staff go is something the YBR Executive Chairman says is never easy.
"I don’t like that."
But to be successful, Mark says one must be able to survive.
"Markets change...so in Yellow Brick Roads case, financial planning, mortgages, etcetera - those markets change, and I have no control over that what-so-ever. None. All I can control is the way I address that. And that sort of kills your confidence because you're building up a model that says 'I will have this amount of sales and I can carry therefor this amount of costs for the next 12 months,'" he explains.
"I'm always working within those changes so my ability to survive is the most important measure of success for me."
The entrepreneur also credits his success to the work ethic instilled in him by his family. His father migrated from Greece in the 1940's, while his mother comes from an Irish-Catholic background.
"All my family [have] always been in small businesses and it comes from that small business mentality of Greeks, Italians, etcetera, people coming after world war two and the best way to make a quid is to make it on your own," he says.
"I watched my father and my mother work their butts off all their lives just to get ahead and improve our lives. So I just did what I always saw... and what I saw was hard work, hard work, hard work, and if you can, work for yourself."
Always be ready to sell
Mark’s keen to see other business succeed as well, and says government can do much more to help.
"I really do believe there should be websites and portals where small businesses can get on and learn how to run their small business. It's one thing to have a great idea and to be skilled. That's a lot different to be running a business around those skills or great ideas, and I think government should be doing that."
He says small businesses often approach him for advice on issues ranging from cash flow management, to digital marketing. One of his biggest tips for owners though, is being ready to sell.
"You should from day one, be prepared to sell your business because you never know when the opportunity is going to come along," he says. "Everything that you do one will be looked at someday by somebody else and their due diligence process... So make sure you're not backfilling. Be forward-filling."
That business savvy has come at a price though, and Mark admits there’s been little room for life outside of work.
"I'm good at the work part, I'm not great at the life part... I've been divorced twice, my personal life has sort of always taken a back step to my business life. But equally I would probably say that's one of the reasons why my business life has been successful."
Mark says he's recently been considering readjusting that balance, with the idea of heading back to Greece, finding a little village and rowing out in a fishing boat growing in appeal.
"It is one my dreams," he smiles. "I'm at a stage in my life now where, to be frank with you, the next five years I've got to start thinking that way, about how do I tone my life down a little bit and get back to being a Greek fisherman."
In the meantime, there's much more work ahead as Yellow Brick Road transitions to its new business model.