You may not know what he looks like, but you’ve probably had a drink in one of his venues. Paddy McKillen jnr shuns the limelight but his work is everywhere to be seen

In rush-hour traffic on Mespil Road, Dublin 4, the driver of a Volkswagen Golf is beeping his horn in greeting. I wave back politely, uncertain who the owner is; only later does it dawn on me.

The vehicle – unshowy, reliable and among the most common car models in Ireland – seems an unlikely choice for one of the country’s most successful restaurateurs and property developers.

But in a way it’s perfect: a typically anonymous vehicle for the low-profile Paddy McKillen jnr. His Press Up Entertainment group owns many of the best-known and snazziest restaurants, hotels and bars in Dublin.

McKillen’s father, the Belfast-born property tycoon Paddy McKillen snr, also liked to keep his head down. For years, the only image in circulation of McKillen snr was a dated black-and-white photo of a tuxedo-clad man.

Only when McKillen snr became embroiled in a 2013 High Court battle with the billionaire Barclay Brothers for control of London’s world-famous Claridge’s, Connaught and Berkeley hotels, did new photographs appear of a silver-haired businessman walking to and from the Royal Courts of Justice.

Developer Paddy McKillen, father of Paddy McKillen jnr. Photograph: Yui Mok/PA Wire

Likewise, his son and namesake remains unrecognisable to the public. To date, no photograph appears in print, online or on social media of McKillen jnr – or none that The Irish Times can verify.

He could all too easily have surrendered that relative anonymity had he chosen to put himself forward for this year’s EY Entrepreneur of the Year (EOY) awards. But instead he insisted that the potential plaudits and attendant publicity go to his business partner, longstanding friend and UCD classmate, Matt Ryan.

When Ryan was asked in a recent interview with The Irish Times why only he had been nominated for the award, he said: “It’s a testament to our partnership that Paddy felt I should go for it and represent the pair of us, and our companies, and our story. That’s a real partnership.”

Paddy McKillen jnr and Ryan’s Press Up Entertainment Group employs in excess of 1,600 people across the 46 venues it operates currently in the capital. It’s a massive undertaking by any measure, but particularly so in a market as concentrated and competitive as Dublin.

Asked how he conducts his business, a source familiar with McKillen jnr’s modus operandi says: “He doesn’t shout or scream or kick the furniture. He’s quiet, thoughtful and unfailingly polite. And he’s straight in the way he deals with you. What you see is what you get. There is no hidden agenda.”

Press Up Entertainment traces its foundation to Paddy McKillen snr’s acquisition in the 1990s of Captain America’s on Grafton Street and the later opening of a Wagamama franchise on nearby South King Street. The group as it is now known came into being formally in late 2009.

Ireland was in the depths of recession and was bailed out by the EU-ECB-IMF troika less than one year later. In this challenging business environment, McKillen jnr and Ryan took advantage of the downturn and the fear it engendered in potential competitors, to grow the Press Up brand aggressively.

Ten years on, the company’s various venues are listed on its website under nearly every letter of the alphabet, and are distributed across Dublin to the point where one would find it difficult to cross the city without stumbling across one of its hotels, bars or restaurants.

Press Up’s hotel offering alone now includes The Clarence Hotel, The Dean Dublin and The Devlin Dublin. These will be joined shortly by the Mayson, which is currently being developed by McKillen jnr and Ryan’s development company, Oakmount, next to the Central Bank’s new headquarters and Ballymore’s 1 million sq ft Dublin Landings office and apartment scheme at North Wall Quay in the Dublin docklands.

The Devlin Hotel, Dublin 6.

The company is also progressing plans for two new Dean hotels, which will be located in Cork and Galway respectively.

Outside of its plans to expand the Dean brand across Ireland’s main cities, the company recently established an office in London with a view to opening a Dean Hotel in the UK capital.

It is understood McKillen jnr explored the possibility of locating a Dean in Berlin also, but found it next to impossible to secure a suitable property owing to the ongoing surge in the city’s property values.

The list of Press Up’s bars and restaurants is far more extensive, and set to get even longer with the upcoming addition of a rooftop venue and boutique hotel on the site of Clerys’ former flagship department store on O’Connell Street. The ambitious Clerys Quarter will include offices, retail units and leisure facilities, and is being developed by Oakmount with its partners on the scheme, Core Capital and Europa Capital.

Elsewhere in the city centre, Press Up has a plan to open a new 300-seater steakhouse on the ground-floor level of the office scheme Oakmount is due to deliver as part of its refurbishment of the former headquarters of New Ireland Assurance on Dawson Street.

Moving beyond the capital, the company is set to open a new five-screen Stella cinema alongside a branch of its Elephant & Castle restaurant at the Florentine Centre in Bray, Co Wicklow. The 250,000sq ft retail-led scheme, under development by Oakmount, is due for completion in the first quarter of 2020.

Revenues for 2019 are expected to hit €80 million before eclipsing the €100 million mark by the end of 2021

Press Up’s current bar and restaurant stable includes: Americana, Angelina’s Bison Bar, Captain America’s, Dime, Dollard & Co, Elephant & Castle, Everleigh, The Grayson, The Liquor Rooms, The Stella Theatre, Stella Cocktail Club, Stella Diner, Peruke & Periwig, Tomahawk, and The Workman’s Club.

Press Up has been lauded for the standard of design and fit-out of its venues. They have certain things in common: thoughtfully spaced, well-finished, photo-friendly and comfortable in a masculine sort of way.

When it comes to the menu however, the critics haven’t been quite as effusive in their praise. While it’s understandable that there would be a certain sameness in the offering given the number of restaurants within the Press Up stable, the company has encountered a similar challenge to many of its competitors in attracting and retaining the chefs it needs to deliver the quality of food required to set it apart from the crowd.

The group plans to open a further 15 hotels, restaurants, bars and a cinema this year and next. Revenues for 2019 are expected to hit €80 million before eclipsing the €100 million mark by the end of 2021, according to Matt Ryan. Press Up’s latest set of accounts shows that its revenues came close to €58 million in 2017.

As exhausting as that all might sound, it’s far from being exhaustive when it comes to detailing McKillen jnr’s ambitions, or the schedule he follows to achieve them. Asked how the businessman manages to keep abreast of all that happens on a daily and nightly basis in Press Up’s venues while also directing the developments being pursued by Oakmount, a source says simply: “Paddy and Matt work very, very hard.”

The Food Hall at Dollard & Co on Wellington Quay. Photograph: Cyril Byrne

Though McKillen is married with children, his typical day sees him working at his office and onsite from 8am at the latest to 8pm at the earliest. Following the short drive home to Dublin 6, the developer is understood to use the hours between 10pm and 1am to send what one source termed the “yes/no” responses required by the 100-200 emails he receives each day from companies and personnel involved in the supply and delivery of goods and services to Press Up and Oakmount.

In describing his friend and business partner to The Irish Times, Matt Ryan credited him with being a “fabulous marketeer” with a “fabulous design eye” and a “very keen eye for revolutionary construction”.

While that might make it look as though McKillen jnr leaves the financial end of things for others to take care of, a source is adamant that he remains across the detail of each project as it is being progressed.

“Paddy could walk into a room in any of the buildings or venues and tell you, off the top of his head, what the wiring or the windows cost,” they said.

Ryan, for his part, describes himself as being “highly operational and team-led”.

“I’m in the engine room . . . I manage the fit-out team on the ground to make sure they deliver the concepts. I look after purchasing, all inhouse costs management, and I also represent us on a variety of fronts in the industry.”

While McKillen jnr’s empire continues to grow at an exponential rate and at breakneck speed, the sheer scale of the business in a market as concentrated and as saturated as Dublin leaves it exposed in the event of a downturn that could be precipitated by external forces.

The prospect of a hard Brexit, the unpredictable presidency of Donald Trump, and the EU’s renewed efforts under its incoming president, Ursula von der Leyen, to make US tech giants pay more tax in Europe, are just some of the factors that could make or break those operating bars, restaurants and hotels in Dublin.

The subject of property may have been a talking point among McKillen jnr and his childhood friends at The Birches, the exclusive residential development in Foxrock, where he grew up

McKillen jnr’s work ethic is something friends and acquaintances say he learned from his father. The 36-year-old’s 1am replies to work emails wouldn’t be unusual for McKillen snr either. The father travels across the globe to deal with his various property investments, which include the 600-acre Chateau La Coste vineyard in Provence in the south of France, as well as prime residential and commercial properties in the US, Dubai, Germany, Japan, Hong Kong, Vietnam, Argentina and Kazakhstan.

In an interview earlier this year, the senior developer spoke of his aim to bring Maybourne, the brand behind Claridge’s, the Berkeley and Connaught hotels, to Paris, New York, Los Angeles and Tokyo, while also developing a new hotel in Kyoto city in Japan and a biotech campus in Vietnam.

Does McKillen snr also play a role in Press-Up? Although he remains a 25 per cent shareholder, McKillen snr has made it clear that the business is managed by his son, Patrick.

Asked if McKillen jnr consults or defers to his father when making business decisions, a source says: “In the early days, Paddy snr would have called and asked what was going on. But that’s very much a thing of the past now. And besides, Paddy snr has enough to be getting on with with his own businesses, without looking over his son’s shoulder.”

While elements of the Press Up Entertainment portfolio are more readily associated with Paddy McKillen snr such as Captain America’s and the Wagamama franchise restaurants, a source with knowledge of the group’s structure and operations explained that these were being operated by the group for the benefit of the wider McKillen family.

The restored Stella Theatre, one of the country’s oldest cinemas, in Rathmines, Dublin. Photograph: Bryan O’Brien

“Patrick and Matt built the business out of the proverbial acorn,” the source said, before adding that: “Paddy [jnr] had to find his own way. He didn’t go into his father’s business when he came out of UCD. He went to work for Smurfits at its carton factory in Cork, and they threw him in the deep end. That’s the way both he and his father wanted it. He got his hands dirty, learned the hard way and it’s stood to him.

“Paddy didn’t want for anything growing up, but what he has now he earned himself. That was instilled in him from the beginning. When he wanted his first car, his father told him to save up the deposit and to take a loan for the rest.”

While there was never any guarantee that Paddy McKillen jnr would become involved in the property game, it was hardly a surprise that he did, given the immersive experiences he and his brothers, Tyrone and Dean, were given from an early age.

Indeed, in the case of Paddy jnr, it is said that he is fond of recalling his first exposure to his father’s business at the age of six.

“He’ll tell you that he can still smell the rotting bread and biscuits inside the former Boland’s Mill on Grand Canal Street,” one source says, referring to the time Paddy McKillen snr brought his son along on a visit to the property prior to its redevelopment by his then business partner, Johnny Ronan, as the Treasury Building.

The McKillen family photo albums are also said to document Paddy jnr’s interest in all things construction from the age of two.

“Nearly every picture you look at, he is holding a toy hammer or a shovel. He was always digging things up or building something,” one family friend says.

Quite apart from being a typical boyhood fan of Bob the Builder, and accompanying his father to construction sites, the subject of property may well have been a talking point among McKillen jnr and his childhood friends at The Birches, the exclusive residential development on Foxrock’s Torquay Road, where he grew up.

For a period in the 1990s, the estate was home to several of the country’s leading developers including Paddy McKillen snr, Johnny Ronan and Seán Dunne.

The children of all three businessmen became friends during this time. Paddy McKillen jnr and John Ronan jnr remain close to this day, notwithstanding their later rivalry on the rugby pitch as the respective captains of the St Michael’s College and Blackrock College senior cup teams in the 2000-2001 season.

Tyrone McKillen, Paddy jnr’s brother, celebrates St Michael’s College’s victory over Clongowes Wood College in the Leinster Schools senior cup game. Photograph: Matt Kavanagh

Paddy jnr’s brother, Tyrone, enjoyed a similar sporting rivalry with Seán Dunne’s son, John, in 2005, when they took to the field for St Michael’s College and Clongowes Wood in the Leinster Schools Senior Cup. Today, both men work as developers together at Tyrone’s LA-headquartered real estate development company, Plus Development LLC.

Alongside his involvement in the development of residential, hospitality and retail properties, Tyrone is an accomplished broker of high-end real estate with the New York-based agent, Compass Real Estate.

Prior to joining the company in March of this year, Tyrone worked with leading LA estate agent Hilton & Hyland, where he was responsible for numerous of California’s most valuable residential deals. The most notable of these saw him securing $88 million (€78 million) in 2017 from the sale to Beyonce and her husband, Jay Z, of a lavish 30,000sq ft mansion developed by his brother, Dean.

Designed by Irish architect Paul McClean, the house at 454 Cuesta Way has eight bedrooms, 11 bathrooms, four swimming pools, a basketball court, a recording studio, a spa, staff quarters, and limestone floors. The property’s glass-walled common areas, doors and windows are bulletproof.

In 2015, Tyrone secured the sale of another high-profile property in the sought-after Bird Streets neighbourhood in the Hollywood Hills to Calvin Klein for $25 million. The property was also built by Dean McKillen.

But while Tyrone and McKillen may be engaged in headline-making deals involving the rich and famous in the United States, their exploits don’t attract the same level of attention or scrutiny here in Ireland as those of their Dublin-based brother, Paddy jnr.

Paddy jnr’s brother, Dean McKillen, with his business partner, Luke Keily, of Bluemedia.

All of which is understandable when one considers the sheer breadth of Press Up Entertainment and Oakmount’s interests in the capital, and their contribution to the city’s social and economic life.

Only last month, The Irish Times reported on Press Up’s plan to expand its operations yet again, with the opening this autumn of its 47th venue on the ground floor level of the newly developed Opus apartment at 6 Hanover Quay in the Dublin docklands. Apart from catering to a traditional customer base of walk-in diners, the restaurant will also offer a delivery service to residents at their apartments and to the building’s private rooftop garden.

McKillen jnr and Ryan have a simple rule of thumb in naming their venues: Press Up’s hotels must have men’s names, while its restaurants have women’s names.

The rapid and seemingly relentless growth of Press Up and Oakmount’s portfolio continues to be backed by a number of financial institutions and funders including AIB and real estate specialist lender, Greenoak, which has its headquarters in London.

In terms of development projects, Oakmount is partnering with Derek McGrath’s Core Capital on several schemes including the Clerys Quarter, the refurbishment and extension of the former New Ireland Assurance Building on Dawson Street, and the delivery of a 40,000sq ft office block at No 73 North Wall Quay in the Dublin docklands.

While Oakmount is operated independently of the Press Up Entertainment Group, McKillen jnr and Ryan frequently use the development arm of their business to deliver buildings that the former can then occupy as a tenant.

For Paddy, property development is more than the numbers. He does it because he loves it, and he takes real satisfaction from bringing great buildings back to life

Explaining the strategy in an interview last January with the online real estate journal, Bisnow, Ryan said: “Oakmount will facilitate that by acquisition and development and Press Up then going in on leasehold. And sometimes we’ll sell that property on to a pension fund and return the capital spend back to Oakmount and remain on as a tenant. That can be very handy when Press Up really wants to get in somewhere.”

A 2018 plan to raise as much as €60 million of fresh equity for the business through an initial public offering (IPO) on the stock exchange remains under consideration, a source familiar with McKillen jnr’s thinking says.

View from Roberta’s restaurant in East Essex St, Dublin. Photograph: Dave Meehan/The Irish Times

“It isn’t something Paddy and Matt are looking to do right now. But the process of readying the Press Up for that possibility has been useful. It helps to maintain discipline around the business,” the source says.

That discipline was evidenced in the case of Oakmount only recently with the sale of the Lennox Building in Dublin city centre for €27 million to a fund managed by Swiss Life Asset Managers. Oakmount and Core Capital acquired the building’s 0.35 acre plot from developer Pat Crean’s Marlet Property Group for €7 million in 2017, and are understood to have spent in the region of €10 million on its development.

In another recent sale, Oakmount secured €10.5 million from the sale of a 0.55 acre site in Dublin 8 to the international co-living company, The Collective.

Oakmount is believed to have paid about €3.96 million to acquire the plot known as “55 Fumbally” in 2017.

But while those two sales are understood to have returned a combined profit of about €15 million for Oakmount and its partners, there has been at least one acquisition where seasoned property industry observers are of the view that McKillen jnr overpaid.

Commenting on the developer’s €38 million purchase of the former headquarters of New Ireland Assurance on Dawson Street, a source close to the sales process said: “There was a third-party application to have that building added to Dublin City Council’s Record of Protected Structures, and that drove the bids from the other parties down. The numbers weren’t making sense any more.”

The designation of the property as a listed building doesn’t faze McKillen jnr however, according to those who know him.

The Devlin Hotel, Dublin 6.

“For Paddy, property development is more than the numbers. He does it because he loves it, and he takes real satisfaction from bringing great buildings back to life,” one source says.

With works on the Dawson Street property due to get under way shortly, Oakmount and Core Capital are understood to have agreed heads of terms with a co-working space provider, WeWork (now rebranded as the We Company), for 70,000sq ft of office space at the building. This is to be complemented by the 300-seater steakhouse Press Up will operate from the property’s ground floor.

Elsewhere in the city centre, Oakmount is to begin construction of a 54-bedroom boutique hotel on the site of the former Howl at the Moon venue on Lower Mount Street. McKillen jnr and his partners acquired the property from the Mercantile Group for €3.2 million in January 2017. The property originally formed part of the now-defunct Capital Bars Group, which dominated Dublin’s nightlife scene during the Celtic Tiger years.

Other projects now under way include a 2,500sq ft mews residence at 10 Ely Place, a 5,000sq ft Georgian office building and mews at 41 Leeson Street, a 7,000sq ft office building on Cardiff Lane in the Dublin docklands, and a 13,400sq ft office development at 61, Thomas Street. In the case of the latter, the works involve, among other things, the restoration of the building’s 17th century roof beams.

Quite apart from its imminent delivery of new offices, hotels and residential properties in the city, Oakmount is gearing up to build 52 apartments on the site of the former Flanagan’s furniture store in the southside suburb of Mount Merrion.

Oakmount acquired the 0.84 acre plot in June 2018 for about €7 million. In something of a departure for the Dublin apartment market, McKillen and his partners intend to offer all 52 units for sale to prospective owner occupiers as opposed to funds and institutional investors. The developer is considering the same sales strategy for the 50 apartments Oakmount has planned for the adjoining Union Cafe site.

The Grayson, St Stephen’s Green, Dublin.

In nearby Blackrock, the company secured planning permission last month for the construction of 291 apartments and penthouses on a 9.7 acre site it owns on Temple Road. Oakmount acquired the lands from the Daughters of Charity of St Vincent de Paul for €30 million in 2017. The development is expected to comprise a mix of owner-occupier and build-to-rent units.

For Paddy McKillen jnr and his business partner, Matt Ryan, it’s all a long way from their first property venture together.

Firm friends from their days at UCD, the duo first joined forces in 2006 to acquire a small site in the exclusive Cork city suburb of Montenotte. Having secured planning permission for a four-bedroom detached house, the pair sold the property on for a handsome profit.