Biting into the Big Apple: The Aussie entrepreneurs who have conquered New York

When it comes to business dreams, going global is well and truly up there.  And, out of all of the destinations in the world to conquer, New York is typically at the top of the entrepreneur collective wish list.

Dubbed the most competitive city in the world (according to the Global City Competitive Index, at least) as Sinatra famously sang, if a business can make it there it can “make it anywhere”.

And while America’s financial hub lures thousands of wannabes annually to its bright lights and concrete jungle cityscape, few of these fledgling businesses actually go the distance.

So, what does it take to make it in the Big Apple? We chat to a few of the expat Australian business owners who have taken their dreams stateside and have found success.

Wish You Were Here Group

When Sydneysider, Nick Mathers, first visited the city he fell in love with its energy and the sense of endless possibilities. But there was one thing that he found lacking: good coffee.

“Twenty years ago it was a real struggle to find a decent cafe that served good coffee,” he told Realcommercial.com.au.

But, despite having never worked in hospitality before, the go-getter took the plunge and opened a cafe in Manhattan using the money he made from selling a house that he had designed and back in Australia.

Little Ruby’s Cafe, New York. Picture: Supplied

“We ended up finding this tiny shoebox of a space in SoHo and opened Ruby’s Cafe with a menu that was inspired by my hometown of Sydney,” he said. And success quickly followed with the “shoebox” reaching cult status soon after opening. Indeed, Nick was approached by none other than Ralph Lauren to open a restaurant in the brand’s Washington DC flagship store and from there  success snowballed into a multi-brand hospitality and lifestyle company: Wish You Were Here Group.

Built on creating dining experiences inspired by travel, Nick’s portfolio is now responsible for some of the most beloved restaurants, cafes and bars across the country, in locations including Las Vegas and Los Angeles, and even overseas with an outlet of Ruby’s Cafe in South Korea.

And while the world is very much now his oyster now, two decades on and a dozen venues later, Nick still has his heart in the Big Apple. There are now four locations of the original Ruby’s brand in Manhattan with a fifth set to open in Brooklyn later this year and he’s still as passionate about his mission as he was when he first took a punt after arriving 20-plus years ago.

Mr Mathers opened Little Ruby’s Cafe in New York. Picture: Supplied

“I’m still loving the feeling and energy you get from meeting new people, inviting them into your ‘living room,’ and taking them someplace special through food, drink and design,” enthused Mr Mathers.

“When I first moved to New York I wanted to bring a small piece of Australia and its warm, laid-back Australian hospitality to the city, something that I felt was missing. I wanted to create a place where you’d come inside and it would take you away from where you were. That’s been the ethos behind Wish You Were Here Group since day one — we want people to feel like they’re on vacation when they come to our spaces. As we grow, we want that to remain the focus.”

TravMedia

When Aussie journalist, Nick Wayland, wanted to launch an idea he had that fused his career in travel writing with the power of a fledgling digital world, he was in no doubt that New York was the place in which he needed to make his mark.

“New York is the capital of the business world,” he told Realcommercial.com.au. “Every major publisher is headquartered here and for us to be taken seriously as a small Australian business, back in the 2000s, we needed to be rubbing shoulders with the movers and shakers of the industry here.”

Juggling travel and motoring sections for the “Wentworth Courier” and writing ski columns for national newspapers in the side, he saw the potential for a platform that connected the media with travel industry professionals.

“I knew the media game and travel and sensed a gap,” explained Mr Wayland. “What if there was a digital hub where travel stories and stunning images could be readily accessed by any journalist, anywhere? That’s how TravMedia was born — a simple website connecting the industry with the storytellers.”

TravMedia owner Nick Wayland. Picture: Supplied

Fast-forward 25 years and that simple idea has become TravMedia — a global network established in nine countries, connecting more than 45,000 travel professionals worldwide.

“We’ve swapped dial-up for dynamic events, hosting thousands of media and exhibitors around the world,” he said. “TravMedia isn’t just a website anymore, it’s the beating heart of travel media, a one-stop-shop where stories are born, connections are made, and the world is explored, one article, one image at a time.”

Now splitting his time between his native Sydney and New York, the CEO and founder thinks that having headquarters in the Big Apple is one of the best businesses decisions he’s made.

“From a time zone prospective, it’s ideally located,” he said. “In the morning you could be speaking with clients in the Middle East and Europe, and by the afternoon and evening Australia and Asia. Our two biggest offices are New York and London, so being located in one makes the most sense.”

25 years on and Mr Wayland has identified South America and the Middle East as areas for huge growth and has plans to expand the company into different verticals such as property.

“The journey has been amazing,” said the 52-year-old.  “I have been very lucky. We have managed to keep our costs under control during the Dotcom explosion and Dotbomb collapse.  If I knew we’d be successful then I probably would have expanded faster, but then again hindsight of very powerful — you just never really know! And with AI now revolutionising the internet and our lives, who knows where we will all be in 10 years time.”

Fishbowl

Despite salad bars being a dime a dozen, Nic Pestalozzi and his two friends believed that the simple concept could be done way better. And this deficit turned into one of Australia’s fastest-growing fast food brands, Fishbowl.

“We were studying at university when we dropped everything to open our first store in Bondi Beach,” Mr Pestalozzi said. “The first store was tiny and an extension of our personality, from music, design, uniforms, it was a fresh experience for the neighbourhood and we built a loyal following.”

Founded in 2016 as a healthy fast-food option for people that hate fast food, Fishbowl’s Asian influenced salad concept fuses an array of fresh ingredients, healthy dressings, and proteins all made from scratch everyday.

“We were filling a gap in the market for healthy, delicious and well-priced food,” said Mr Pestalozzi.

Thisbowl in New York. Picture: Supplied

Despite their journey to salad supremacy beginning a mere eight years ago, the brand now has some 46 locations across Australia and has disclosed sales well above the $50 million mark over the past year alone. But it’s their expansion stateside that has become the most recent cause for celebration.

“New York is the epicentre of the world,” continued Mr Pestalozzi. “An iconic city with global reach and exposure. We wanted to play in the most competitive market in the world because we believe in our offering, and had the experience and knowledge to back it up.”

Opening in the trendy NoHo neighbourhood in April, the unique fast food concept – rebranded as “Thisbowl” – was an instant hit with New Yorkers.

“Since Day One we’ve had a line out the door all day and night — we’ve been blown away by the response,” he said. “We’ve been featured in every news publication too  — from The New York Times to The Wall Street Journal.”

Thisbowl has been feature in The New York Times and The Wall Street Journal. Picture: Supplied

While the hype around the launch has been pronounced Mr Pestalozzi is quick to assert that their American debut wasn’t all plain sailing.

“The whole experience was new and challenging,” he said. “Navigating construction, permits, workers rights…it was all new and part of the process. But nothing good comes easy!”

Looking ahead both Mr Pestalozzi and his co-founders are looking to expand rapidly with another 100 or so Australian locations are in the pipeline.

“Opening New York has been the biggest milestone for our brand to date,” said the 31-year-old. “We’ll focus on NYC for the next couple years, whilst continuing to get better as we grow in Australia.”

A Man and His Sandwich Tours

When holidaying in New York in 2014 Sydney-born, Ben Gollan, had a career epiphany during the most unlikely of circumstances: whilst eating a sandwich.

“I enjoyed the greatest sandwich of my life there and actually started a sandwich Instagram account off the back of it,” he recalled. “I knew I needed to figure out a way to have that sandwich become a more permanent feature in my life.”

Ben’s moment came two years later when his wife — who worked for American-based company, Audible — was offered an opportunity to move to their New York HQ.

“We jumped at the chance,” he said. “Even though I knew my current career was not transferable as Australian public service jobs in there were almost non-existent, plus to practice law, I’d have to sit the New York bar exam, which I had no interest in doing.

“When I then discovered that not a single sandwich tour existed in the city — strange as it’s considered to be the sandwich capital of the world —  I was blown away. The next day I approached the owner of a great sandwich shop to be part of a ‘bar crawl for sandwiches’. They agreed, and so the ‘New York Sandwich Tour’ quickly fell in place from there.”

Ben Gollan of The Man and his Sandwich Tours. Picture: Supplied

Turning his back on a decade in the Federal public service to dedicate his life to sandwiches (“Mum and dad were very pleased with me!” he chuckled) Mr Gollan launched A Man and His Sandwich Tours, which neatly coincided with the launch of Airbnb’s ‘Experiences’ arm — a platform which proved to be the perfect vehicle for his offering.

“New York is a city filled with endless possibilities where even the craziest of ideas are not just supported, but are encouraged,” he said. “So, the concept of a sandwich walking seemed less crazy and less of a risk to launch here than had of I attempted it back home in Sydney.”

Now aged 41, the self-proclaimed ‘chief sandwich officer’ is happy to reflect on the last seven years and the milestones he’s reached.

“We have launched more than half a dozen different sandwich experiences – both in-person and virtual experiences – and become the #1 reviewed tours in NYC on the Airbnb platform thanks to the 27,000-plus guests we have welcomed.”

But success hasn’t come without some serious grafting.  “Like any business, staffing is a challenge,” he said. “The very nature of the tourism industry – with its seasonality and irregular working hours – means that employee retention can be a challenge.

“But, it has all been worth it and I wouldn’t change a thing. We’re expanding with a new tour in New York launching next week (The Sandwiches of Times Square) and we’ve actually gone beyond the city, launching a Nashville Sandwich Tour earlier this year. It’s our first foray outside of New York, but not our last, so watch out sandwich cities of America!”

Layla Bar

It was a final year university tour of the US that changed the direction of Stefano D’Orsogna’s life entirely.

“I graduated at the end of 2015 with a finance and economics degree,” he told realcommercial.com.au. “And then I travelled through the US with a few of my best mates. While we were in New York, I fell in love with the city, and decided to take a year off there.”

Leaving his native Perth for the Big Apple, when he arrived in 2016 he discovered that the Australian-style of cafe was booming.

“I was amazed at how vibrant and busy these places were,” he said of the time. “But I was also amazed by the fact that they were run by young Aussies.”

Inspired, he made his hospitality debut as part of team of Aussie expats opening a new cafe. It was here where he both cut his hospitality teeth and sowed the seeds for his own restaurant.

“I saw firsthand the founders having immense success in an industry that I had always thought impossible to crack,” he said. “Having forged a strong working relationship with the two owners, I then partnered up with them in 2019 to open my first restaurant, Sonnyboy.”

Layla owner Stefano D’Orsogna (left). Picture: Supplied

Managing the all-day Australian eatery successfully for four years, Mr D’Orsogna called time on the business in 2023, selling to open his new venture, Layla. A neighbourhood bar-restaurant focusing on aperitivo-style cocktails and a food offering inspired by Spanish and Italian cuisines, Layla, has become a go-to for Brooklyn’s hipsters.

“I wouldn’t change a thing,” he said of his journey. “I was definitely way too inexperienced to open my own venue back when I first arrived. I think that played into my favour as I was too naive to understand all the risks. I made a lot of mistakes in our first year of running Sonnyboy, but I think that accelerated my understanding of the industry.

“I was able to navigate the business through COVID and then we really hit our strides in 2021 and 2022. Having experienced a full business cycle from open to a successful sale, I had a lot of confidence I could do it again with Layla. And after just one year of being open, it has been pretty good.

“We’re already scouting other locations for a bigger venue and long term it would be amazing to be involved in the boutique hotel industry. I see hotels as the ultimate version of hospitality as there are so many different touch points to wow your guests and that really excites me.”