How Jamie Green Went From Sleeping Rough to Social Entrepreneur


“I had hit really rock bottom.... as in no money left, collecting debt by the day and selling everything."


Jamie Green’s business started with a one-night stand. That’s right. He stood upright inside a Perspex box for 24-hours on an inner-city Melbourne street. The stunt marked the launch of his sleepwear range and, in addition to bringing in a cool AU$27,000 in pre-orders, captured the attention of a certain Sir Richard Branson, who took it upon himself to publicly congratulate Jamie on Twitter.

At 7am this morning, Jamie, along fellow ‘crusader’ Zac Miguel, once again made a public statement about enduring injustices in the world. Enclosing themselves in a small space with only a glass window to the world for 156 hours, their Melbourne-based box is where the two friends will eat, sleep, bathe and sleep for the next six and a half days, raising awareness for the tens of millions of people around the world who are trapped in modern slavery.

Two years on from that first stunt, and before Jamie enclosed himself in a box, he tells Collective Hub about how his growing brand, One Night Stand, has found love with General Pants Co., settling down in an exclusive partnership.

“We’ve gone from ‘Jamie doing absolutely everything’ to working with a huge [brand] who’s doing a hell of a lot more for us and distributing us throughout the whole country online… so we can make a bigger impact,” says Jamie. And he doesn’t just mean in bed.

One Night Stand adopts the one-for-one model (think TOMS but with PJs). Every sale sees a meal provided to homeless youth through giving partner, Ozharvest, and 50 per cent of the company’s profit is donated to shelters and employment projects.

“We’re sort of blossoming out of our start-up years and moving into something a little bit more secure,” Jamie continues. “The roller coaster is not so rough at the moment!”

And rough, Jamie knows. In 2010 he was sleeping on friend’s couches and the floor of his struggling café.

“It was my first really, really major failure,” he says. “I had hit really rock bottom. And rock bottom as in no money left, collecting debt by the day and selling everything. I sold another business to keep this one afloat, moved out of my apartment because I couldn’t afford to pay rent anymore… it was really rock bottom.”

But giving up didn’t come easy to this steadfast entrepreneur, who buried his head in the pages of Richard Branson’s Screw Business as Usual and, as luck would have it, got a fresh start with the sale of his café and a scholarship to Melbourne’s School for Social Entrepreneurs.

“Going into an incubator was probably the best thing that could’ve ever happened to me,” says Jamie, who dropped out of school in Year 10. “You’re literally getting shoved in a room and pitched to the board at Macquarie Bank for AU$10,000 and you’re like, ‘Holy shit!’ That’s not even like a pretend thing, it’s real money and I’ve got to pitch to these guys.”

As well as rounding up a “huge network”, it was here that Jamie discovered the importance of having a mentor (he’s since kept a few on rotation) and picked up the art of ‘action learning’: “Which is where you sit in a group of say seven people and submit your problem. Like, ‘I don’t know how to raise funds for my business’, and for the next forty-five minutes they ask you open-ended questions and you’ve got to solve your own problem.”

Then there were the lessons he wishes he’d known back at the café.

“A lot of stuff, like piloting an idea before you throw absolutely every single cent that you have at it… [and] involve yourself in the market that you’re going to enter as much as possible. So if you’re entering the fashion market and you’ve not been in the fashion market before, indulge yourself there for three months and go to every single meeting you can go to, read magazines about it, really educate yourself well before jumping ship. Because a lot of it is [about] relationships.”

As Jamie’s found firsthand with General Pants. Even in its infancy, One Night Stand had the support of ING Direct’s Dreamstarter Program and fellow social enterprise Grill’d.


“Those guys that were already successful in the market, they’re doing something, and if they believe in your idea, they can lift you up and boost you and push you out into the market a lot quicker,” says Jamie, who didn’t shy from making his budding business known.

“When I was building One Night Stand I literally just met anybody I possibly could meet with the title ‘C-E-something’ or ‘C-O something’, and I was so blessed to get introduced to some pretty big players in the market. It was very much just starting off with cold-calling and cold-emailing, if that’s a thing… You’ve just got to be yourself basically, and if you back your idea enough and you’ve got enough passion behind you, most people at least give you a shot.”

Having just dropped his second One Night Stand range with the General Pants Co buyer in mind (“We did research into their customer and found females were more into sleepwear. Men tend to just sleep naked or in an old t-shirt”) Jamie, true to form, is on to something brand new.

“I teamed up with a couple of entrepreneurs and we started a company that builds other start-ups and social businesses. That’s what I do with my spare time. I build other businesses!” he laughs. “And that company’s called Marching Elephants. We’re constantly seeking new opportunities and new relationships to build businesses that will have impact in the future. Obviously we see a lot of holes in current business models where they’re not being sustainable and they’re not thinking about the future of the country or the world, so we want to help those people with those ideas and get them to market.”


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