Justin Hemmes believes in keeping a close eye on his empire.

"I can see everything," Merivale's chief executive says, swiping his mobile phone's screen to demonstrate. It lights up with a mosaic of live security camera feeds streaming in from the myriad corners of his Sydney hospitality business.

"I can see all the venues ... I watch all the cameras from here." He zeroes in on two particular live scenes to illustrate his point: a bar room showing someone arriving with a beer delivery, and another Merivale interior in which an employee is conversing on a phone.

"Wherever I am around the world I can keep an eye on things." He closes down his mobile. "Doesn't make for great conversation, though, at the [dinner] table."

It looks like a high-pressure time for the 43-year-old boss of this privately owned company. The next four months mark a period of extraordinary expansion, raising the questions "how" and "why".

Eight new Merivale outlets are scheduled to open – some within already owned properties, others bought for an estimated total of $66 million – with vast amounts more money flowing through them via refurbs and restorations.

Hemmes is just back from a two-week European holiday, appearing poised and at ease.Things are clearly changing for the man once described by CNN as Sydney's ultimate playboy and who today sports a casual blue T-shirt, loose trousers, carefree charm and an Aeolian Islands tan.

Half an hour ago, under the watchful gaze of his dog, Thunder, he was posing for pictures in the vegetable garden of The Hermitage, his family's harbour-front Vaucluse home. He is proud of having created this well-tended enclosure from a tennis court, and that it can now provide everything from blackberries and pawpaws to a regular supply of fresh eggs (one of which is laid during the shoot) from three types of chickens – silkies, bantams and Rhodesian reds.

Visuals done with, the CEO is sitting on a designer rocking chair in an airy room. As we speak he finds himself fielding sporadic questions from various Hermitage employees, including the gardener ("I'm never here so they're taking the opportunity to talk to me.") while his pregnant girlfriend, Kate Fowler, pads around barefoot in the background.

Their baby is due next month and Hemmes could scarcely be more smitten. The timing of fatherhood – indeed of everything – seems spot on, he says, bringing his focus unswervingly back to his company.

"I'm in a really good headspace. For the first time every element of the business feels right to me, the direction we're going, the team, it feels right. A lot of my life is about gut feeling."

As years go, 2015 could barely be more significant. It marks 60 years since his father, John, launched a Sydney fashion label named after Merivale, Hemmes' mother – a young milliner set to emerge as a remarkably able, prolific and influential avant-garde designer.

On March 1 the dapper "Mr John" died at the age of 83 from cancer. His passing prompted public review of a man who had survived brutal treatment during World War II as a child internee in the Dutch East Indies, and arrived in Australia as an adult with little more than the indefatigable determination that made him one of the nation's most intriguing self-made millionaires.

He masterminded a pioneering fashion label, switched his firm's focus from design retail to hospitality in the 1990s, brought his two children, Bettina and Justin, into the business and initiated what would become a significant property portfolio worth (according to media speculation) in excess of half a billion dollars.

His death was followed two months later by the unexpected demise of Angus Hawley, one of Justin Hemmes' oldest friends.

Hemmes became Merivale CEO in 1997. He quickly stamped his signature on both the operation and Sydney's CBD with the opening of the fashionable, buzzy bar-restaurant-nightclub the Slip Inn. Since then, amid a whirl of headlines everywhere from the business to the social pages, he appears to have barely paused for breath.

Merivale Group opened the Angel Hotel and Establishment in 2000; Lotus, the Grand Hotel and the Jam Music label in 2002; the Wynyard Hotel (2003); Ivy (2007); the Beresford Hotel and Felix Bistro & Bar (2010); El Loco at the Excelsior Hotel; the Upstairs Beresford live music venue, and 30 Knots in the Grand Hotel (2011); Mr Wong (2012); El Loco Slip Inn and Manly's Papi Chulo (2013), and Coogee Pavilion (2014).

The drumbeat of acquisition, reconceptualising, rebuilding, talent scouting and venue launching has seemed relentless. It has reinvigorated and reimagined Sydney's dining and drinking scene, and garnered an ever-increasing cache of major industry awards in the process.

Merivale has more than 50 sites and the empire is expanding. Shortly after his father's death, Hemmes bought the Newport Arms in Pittwater for a reported $50 million but when it comes to the size of the business, beyond the fact that Merivale employs about 2500 people, he is politely evasive.

"It's private," he says, gently batting off questions about turnover and net worth with a non-committal "Yeah – I don't know," before catching himself, grinning, and qualifying his comment with, "Well, I know but it's ... all just words and figures.

"All it does is allow me to grow more. The more successful the business is, the more money we can use to create new businesses, employ more talent to do more challenging, exciting things. That's all it is, it doesn't really make any difference to living."

He pauses. "All right, I suppose I wouldn't be able to afford the farm [in May Hemmes spent a reported $7.5 million on a spectacular, sea-hugging, 60-hectare property called Glasshouse Rocks near Narooma on NSW's far south coast] if it wasn't doing well.

"But we don't, my sister and myself, see it like that ... It's more, 'Let's just do it and have fun, and if it turns really good, we can do more.'"

Of late that is what has been happening, according to Hemmes, who seems driven by sheer enjoyment. He describes various aspects of his work life as "exciting", "beautiful", "a pleasure", and "inspiring ... I love it, I love it, I love it."

Over the past few years, Merivale's trajectory has been one of "exponential growth", he says, allowing him to fund "opportunities" by funnelling profits back into the business.

"The better a team that we have on, the more profitable, and I always reinvest back into the company," he says. "The team's stronger than ever, and our model is, I think, more solid than ever, so it allows that rapid growth. If I didn't have the right people in place I wouldn't be able to expand like this."

Hemmes mentions a couple of key personnel – Merivale's chief operating officer (Brett Sergeant, whose LinkedIn profile cites a quadrupling of business growth over a seven-year period), and Carol Campbell, group business and finance officer.

Asked if he has someone who scouts for potential new properties Hemmes shakes his head. "No, that's just me. I'll know within 30 seconds if it is going to be of interest or not."

"As soon as I see the opportunity I can envisage how it is going to look ... sort of 80 per cent of how it will end up," he says. "Once we've bought the site, 'Tini [as he calls his sister] comes in for the design process ... We have our internal team, which is myself, Bettina and another in-house stylist, and we work directly with the architecture firms. It all happens very quickly."

As Hemmes talks it seems he is stepping away from a series of shadows. His past, as relayed by the media, appears one of carefree rich-heir hedonism – peppered with tales of Hollywood buddies, beautiful girlfriends, fast cars and close calls (crashes include flipping his speedboat on Sydney Harbour). Yet he is very much his father's son, in that life ultimately revolves around the business.

Asked about mentors, he cites the late healthcare entrepreneur Paul Ramsay, Bruce McWilliam, of Seven West Media, and David O'Donnell, of Addisons Lawyers, the common denominator being "how these people are as people".

"I love that someone can be so personable and so warm and welcoming, and engaging," he says. "They are incredible minds, incredibly successful at what they do ... they've got beautiful families and are loving to their families."

Ruthlessness in business does not interest him, he adds. "You can be successful and a good person."

His high-profile father's death marked the end of an era but Hemmes says he had not been a pivotal part of the business for at least 15 years.

"I really don't have to report to anyone," he explains, returning to the topic of instinct. "Gut feeling is everything. It is backed up by financials and I am very good with figures. Figures have always been my forte."

At the beginning of each new project Hemmes creates his own forecasts of turnover and net profit. The end results are invariably "within 5 or 10 per cent" of those first, fast figures, he says.

"I get a lot of input from my team ... If we're borrowing from the banks, the banks have to sign off, but we have a great track record now, so it's a different process than it used to be."

In 2014 he tried something new, buying Coogee's Beach Palace site in a structured purchase arrangement. It was not a happy experience, culminating in a dispute with the vendor that was settled earlier this year in the NSW Supreme Court.

Of legal action in general Hemmes observes, "Kerry Packer said to me, 'The only time you should ever go to court is when you are wrong', which I think is just magic ... It is a very draining process emotionally and mentally, and unfortunately because I'm sort of like the face of the business, it becomes quite personal."

There have been ups and downs but "not financially", Hemmes says firmly.  He does admit, however, to having felt "very uneasy" at times.

Asked to clarify he talks about having "all your eggs in one basket", and a situation in which 70 per cent of commercial success comes from one operation. "That's stressful because if ... something happens, you can be in dire straits."

Today Merivale is "a stable offering and not susceptible to market influences or regulatory influences; I think we can almost handle anything that's thrown at us now".

"We've moved away from clubs too," he adds. "We were very club-heavy and a lot of the business was reliant on the night-time economy. The night-time economy is finished. It is destroyed. It is all over, and I don't see that changing any time soon."

Hemmes puts that down to the lockout laws, government regulations, public perception and the "tragic incidents that occurred in the Cross". In 2013 NSW government figures indicated The Ivy was the most violent venue in NSW.

"We were in the hands of the public and if they did something stupid, or they hit someone, or did something we are the ones that are held accountable for it," he says.

"I wouldn't sleep at night, and when I finally did get to sleep (Hemmes mimes being unable to breathe and bursting awake with his hands clenched) the first thing I'd do is look at my phone to see if there's any messages ... I was walking on broken glass every weekend. Ever since it became a real public issue, so probably for about six years."

By necessity and by choice Merivale is now more food-focused. "It's a better way ... food and beverage should be enjoyed together," Hemmes states, before bursting out with a laugh: "Also, I'm getting old. I don't go to clubs. This is a prime example of how the business shifts with my age."

He fires up his mobile phone again to reveal pictures of "the farm", his new retreat, taken with his drone, and floats the fantasy of populating this new kingdom with a quasi-commune of like-minded friends and their children.

It will be a place of simple, practical, nature-based activities far away from the city rush, the CEO says. He describes fishing for lobster, abalone and prickly sea urchin, a creature most people wouldn't know how to open. "My kids are going to know how to do that by the age of four.

"I've learned so much in the last year because of the intensity of what's happened," he adds thoughtfully. "Losing Dad and then Angus ... falling head over heels with Kate and then the baby coming, and then all these developments and growth of the business – such confusing emotions.

"I try to see the positive in everything now."

Merivale raises the bar with eight new Sydney openings

Justin Hemmes has long copped flack from keyboard warriors and pub politicians about "gentrifying" Sydney and promoting soulless "yuppie" culture. It's a bit of a rough call.

Would you rather have a supermarket-owned pub selling Shop A Docket schnitzel as your local or somewhere with a top-notch chef and floor your feet don't stick to?

Hemmes gives a genuine damn about making Sydney, a city a that he loves, a world-class food and drink destination, and the next five months are perhaps the biggest in Merivale's history. Here's what's on the cards.

J&M

Level 3, Angel Hotel, 125 Pitt Street, Sydney

Opening: Late October

The lowdown: This whisky bar at the Angel Hotel is a tribute to the late "Mr John" Hemmes (J&M stands for John and Merivale, you know). It has interiors inspired by old haberdashers, a drinks trolley named "the Sidecar", a long glass bar and chesterfield lounges (a prerequisite for any whisky bar). For its first three months, the bar will be a showcase for Chivas Regal 18 and provide a "unique, sensory whisky experience".

Why you should care: House of Merivale was a swinging, multi-level retail and dining hub when it occupied The Angel Hotel in the '70s. This a chance to sip a whisky and soak up Sydney history.

The Paddington

384 Oxford Street, Paddington

Opening: November

The lowdown: Handsome French rotisseries will be the centrepiece of the pub once known as the Paddington Arms, and former Momofuku Seiobo​ executive chef  Ben Greeno​ will be roasting everything on them from whole stuffed fish, lamb rump and beef to Jerusalem artichokes and celeriac.

"It's food that's going to lend itself to a good time," says Greeno. There'll be a cocktail bar upstairs and punters are free to rock in for a quick beer as they like (it's still a pub).

Why you should care: Greeno is a terrific chef and very comfortable in a pub. Expect nothing but deliciousness to slide off those rotisserie shafts.

Oxford Street Chicken Shop

382 Oxford Street, Paddington

Opening: Late 2015

The lowdown: Greeno has fond memories growing up in Britain and visiting his aunt's chicken shop in Dartmouth. This takeaway (name TBC) next door to the Paddington is a chance for Greeno to relive those memories by selling rotisserie chicken, sandwiches and the kinds of salads Greeno likes to eat. "Ones with a lot  of grains and pulses, that are fresh and light."

Why you should care: Too much takeaway chicken is greasy, tasteless and overcooked. This chook promises to be the kind of bird you can take to a Centennial Park picnic, eat in front of the telly or put on the table for a fancy long lunch.

Queen Victoria Hotel

167 Enmore Road, Enmore

Opening: January

The lowdown: Mr Wong's dumpling master, Eric Koh, is back on board the Merivale mothership and will be pleating up a sui mai storm at this Enmore pub.

Papi Chulo champions Patrick Friesen​ and Chris Hogarth will be joining him and looking after the barbecued meats and semi-traditional Cantonese side of things.

"It will Like Ms.G's, but with Chinese food," says Friesen. "We'll have typhoon shelter crab, which is one of the best things ever.

"It's basically a deep-fried mud crab tossed in deep-fried garlic, chilli and black bean. It's so tasty and just makes you want to drink beer." There'll be plenty of it to drink too, because the Queen Vic wants to be a locals' boozer, first and foremost.

Why you should care: Because there's schooners, fried crab and Eric Koh dumplings, of course.

Newport Arms

2 Kalinya Street, Newport

Opening: January

The lowdown: Coogee Pavilion for the northern beaches. Merivale purchased the massive hotel in March 2015 and the first stage of the redevelopment opens in summer with a huge outdoor food and drink concept headed by chef Sebastien Lutaud. There will be a sunset bar, cocktail bar, burger shack, seafood kiosk and a Vinnie's Pizzeria. Summer starts here.

Why you should care: The Newport Arms is an institution of the north with stunning views of the bush and beach and this redevelopment will bring it up to speed with the current age of drinking and dining. Vinnie also cooks a mean pizza pie.

European Wine Bar

50 King Street, Sydney

Opening: February

The lowdown: Pop-ups at the work in progress site (currently occupied by Eric Koh and his bamboo steamers) will stop progressing in 2016 when a sophisticated European wine bar (name TBC) sets up shop for the long haul. Former Sydney Morning Herald Good Food Guide Sommelier of the Year, Franck Moreau, is in charge of the bottles. Huzzah.

Why you should care: There's very few decent wine bars in the CBD so a new one with a Master Sommelier-curated list is cause to take the champagne off ice.

Fred's

380 Oxford Street, Paddington

Opening: February

The lowdown: This produce-driven restaurant from Danielle Alvarez (an alumna of Alice Water's Chez Panisse and the three Michelin-starred French Laundry) is the third venue in Merivale's Oxford Street mini-hub.

Alvarez has been forging relationships with organic horticulturalists since arriving in Australia a year ago and will be sourcing heirloom vegetables and native ingredients from the Blue Mountains to be cooked using a wood-fired hearth and oven.

"Cooking with fire forces you to be a bit more vigilant," says Alvarez. "It's not just turning on a switch, it's not just pressing a button. You're constantly looking, you're smelling, you're tasting and I think that creates a perfect result."

Felix's head sommelier, Adrian Filiuta​, will be looking after a 120-strong wine list with a focus on small-batch drops.

Why you should care: Because there can never be enough restaurants showcasing beautiful produce cooked simply over fire. This one's going to be special.

Sussex 1854

Basement, 380 Oxford Street, Paddington

Opening: February

The lowdown: A prohibition-styletapas bar, similar to Palmer & Co. in Abercrombie Lane but with its own distinct flavour.

In the basement underneath Fred's Bar and Bistro, it will feature seasonally led cocktails inspired by Danielle Alvarez's philosophy of letting ingredients speak for themselves.

Why you should care: Palmer & Co. is the best bar in Merivale's portfolio and an Oxford Street version of the same adds further life to the area.

-Callan Boys