It’s a far cry from the three-piece suits the fashionista – once crowned one of Queensland’s 50 most stylish – is known for.

“Everyone keeps saying to me they’ve never seen me dressed so casually,” he laughs, apologising for his relaxed attire, adding he hasn’t had a chance to iron his shirt yet.

The informal accoutrement comes as a consequence of his new-found fatherhood, having welcomed son Krug – named after the premium French Champagne and its association with strength and individuality – in January.

“I took six suits to the dry cleaners in two weeks with all the baby spit-up and everything,” says the hands-on dad, who has returned from a business meeting at 6 o’clock that morning to which he took the happy, social bub along.

He and wife Courtney – who have been together for more than a decade and run one of Queensland’s most successful real estate agencies, Place Kangaroo Point – which has achieved more than $500m in property sales in the past 10 years, are handling first-time parenthood with the same stoic, get-it-done attitude they take into their business.

“Having a child didn’t mean we could just put a handbrake on business because people don’t go, ‘OK, you’re out, we’ll wait for you to come back’,” Caulfield says, revealing his agency scored top spot in the Place group for the first quarter of this year.

“So we really wanted to make sure that we delivered on both fronts and I think that’s what I love about being a dad is I just become more efficient with my time because I have to be home for him,” he shares, adding he’s still working 14 and 15-hour days.

“I do daycare pick-up or drop-off, I take him to meetings and I think 90 per cent of our clients love that.

“In a way it’s sort of been a little bit of a benefit to us as well. I’m sure a few people have signed contracts because they’ve been distracted by his cuteness.”

Caulfield also has no qualms about taking his son to work because it was the way his parents, Colin, a superintendent greenkeeper, and Cindy, a jill of all trades, raised him and his two younger brothers.

Leading a nomadic life going where the work was, his family moved from the country NSW town of Tamworth to North Queensland’s idyllic Airlie Beach, then down the Queensland coastline through the Sunshine Coast to Narangba, with his dad employed at various golf courses along the way.

It was during this time a young Simon would accompany his dad to work; his father teaching him how to mow the fairways and greens, rake bunkers and even cut holes in greens.

It led to a love affair with golf and dreams of making it professionally, but most importantly it taught him the life-changing skill of networking.

“Being a part of the golf course you’d meet people and I’m a questions guy, so I’d be like, ‘What do you do? Why do you do that?’,” he says, revealing he hasn’t changed.

While the dream of joining the PGA tour was quickly dashed when he realised his ambitions were greater than his talent, his casual conversations on the golf course led him to move to the “big city” of Brisbane on his own, scoring his first proper job as an 18 year old.

A bloke called Colin, who played at one of the golf courses Caulfield’s father worked at, offered him a gig as a wharfie moving about 1000 cars a night for an auto company at the Port of Brisbane.

“It wasn’t the greatest job in some respects, but I was appreciative of it because it was well paid and I got a bit of freedom and I’ve never been an indoors guy – you’ll never see me behind a computer for more than an hour,” he says.

It also allowed him to live out his bachelor dreams, renting an apartment at The Emporium complex in Fortitude Valley which, at the time, was the ultimate hangout for young people with the coolest restaurants downstairs and the city only a short walk away.

The wharf gig would then become the catalyst for him to pursue real estate, after meeting an agent on the job who saw sales potential in him and introduced him to her father – top Brisbane northside property gun Brian McGrath.

Caulfield, then 20, worked for McGrath for a fortnight before realising selling suburban homes around Chermside wasn’t for him, deciding instead to try his luck in the New Farm/Fortitude Valley area where he lived.

Dropping the McGrath name on his resume, he swiftly scored a job with a New Farm agency with no retainer, sick leave, holiday leave or benefits. That also meant no way to pay for his rent or food, so he took a part-time job at clothing store Diesel at Brisbane DFO, working Saturdays and Sundays around his 60-70 hour/week real estate gig to cover his bills.

“I think learning to sell jeans at $350 and selling a house at a million dollars was the same principles: asking questions, giving good customer service, and you had to be very good at identifying someone’s needs before they walked in,” he says.

After working for a couple of different agencies, Caulfield scored his big break when he managed to convince “Brisbane’s queen of real estate” and one of the state’s most successful agents in history, Judy Goodger, to give him a job at her new agency Place New Farm.

Synonymous with the Brisbane prestige property market, Goodger took the then 23-year-old Caulfield under her wing, becoming what he describes as a “second mum” and showing him the secrets of how she achieved more than $1bn in residential sales.

“If I didn’t join Place New Farm and be under Judy’s tutelage, I’d never be where I am today,” Caulfield says humbly.

“I just copied everything Judy did. She asks for ads in the paper, I’m going to ask for ads in the paper. She does auctions, I’m going to do auctions. She gets cash offers, I’m going to ask for cash offers. So I really mirrored myself off her and I think that helped me become very successful very early on.”

In fact, Caulfield achieved his first million-dollar commission at just 26 years old – a considerable improvement on his first ever commission of about $3000 for selling a home in Woolloongabba just a few years earlier.

He has since gone on to sell out entire buildings, including Walan residential tower at 2 Scott St, Kangaroo Point, for $44m, 11 Thornton St, Kangaroo Point, for $79.5m and Haven Newstead for $33m. He also holds 11 suburb price records.

For major milestones he rewards himself with something special for the time and effort that has gone into the achievement, revealing a passion for watches that saw him buy a rare timepiece when he sold Walan.

His other splurges are on dining out, travel and clothes, with a penchant for luxury suits from the likes of Hugo Boss and premium Brisbane brand Urbbana. They’re a far cry from his first suit – a two-for-one special at Tony Barlow when he began in real estate and it was all he could afford.

“For me, presentation is a big thing,” he says.

“Some people look at you and go, ‘If you don’t wear a tie and you’re not clean-shaven and you haven’t done your hair, you’re going to be scruffy so therefore you maybe aren’t going to be good at execution on the process of how you sell my home,’” he says.

“I wear three-piece suits even through summer because I still want to look professional … I think that’s the proud part. It’s a bit of self pride, self love. Be passionate about who you are.”

But don’t confuse pride for ego. While there is certainly an air of confidence with Caulfield, it’s not cockiness, and despite his successes he remains humble. Something he tries to impart on to his team. “In our industry, there’s a lot of flashy. You can wear a nice suit, you can drive a nice car, all that palaver, that’s great, but that doesn’t really define what you’re doing. That’s a reward element,” he says.

“It comes back to culture. What is it that we’re delivering? Are you hard working? Are you honest? Are you coachable? And I mean honest in the way that I’m conducting myself. Am I being honest with my clients?”

This honesty, integrity and humility is also what he wants to instil in his son as he grows up, despite the fact Krug will no doubt be living a privileged life, with his parents writing up about $150m in sales annually across the business.

“I went home from Tamworth Hospital in a Datsun, my son went home in a (Mercedes) G63 AMG – the world’s distorted in that sense,” he says. “But I do want my son to learn that life’s not easy. For him, it’s not giving him everything at his demand and want. We’re in that day and age of here’s a phone, here’s a new toy. We (my brothers and I) used to fight with sticks in the back yard.”

Also part of ensuring Krug doesn’t grow up entitled is providing a solid family unit for him, with the couple who live together and work together constantly putting time and effort into their relationship.

“Divorce – I’ve seen so much of it in my time in real estate and I hate it,” Caulfield says. “It’s one thing that motivates my wife and I to not be a statistic. How do you work together and live together and do everything, and I think when we see the challenges that people go through day to day, you are thankful that you’ve got a great home and a great partner and support.”

Whether the pair will have a second child, the 37 year old says is up to his 34-year-old wife, acknowledging the career imposition it places on her as one of Place’s top agents, as well as the physical and mental demands.

While he says he would be happy with whatever she decides, if they do plan to expand the clan, Caulfield will be prepared with his new office on Shafston Ave in Kangaroo Point, which will open later this year.

He’s currently working on a 400sq m premises that will be part office, part wellness centre, with a gym, sauna, steam room, cold plunge, golf simulation room that will double as a creche for the children of agents who need childcare after school, and a kitchen serving healthy, chef-cooked meals.

“Part of our focus of the business is the mums and dads who can come in with kids and not feel like they can’t go to work and still be part of the culture because, yes, you can work from home but you don’t get the culture, you don’t get the support, you’re literally on your own,” he says.

“And if people are busy they’re still eating good quality food and if people are sacrificing their health for their career, there’s no excuse because the gym, the wellness centre’s there.”

The top-tier facilities were inspired by a trip to the Google office in the US in 2018.

“I just learnt that you can enjoy your work and spend a lot of time there if you have the right people, the right environment, the right direction and vision. So Google really imparted with me that if I want to be a great business owner, I have to be in tune with my employees – or colleagues as I call them, and our clientele.

“There are mums who have to put a handbrake on their career because maternity leave is frowned upon and I think that’s ridiculous – it’s an important part of life.”

The office building will also boast a mortgage broking service and a law firm – creating an almost one-stop-shop for all your home-buying needs.

“We’re pretty pumped. It’s just making people’s lives easier,” Caulfield says.

“For us it’s an evolution of our organisation.”

It’s all part of Caulfield’s goal to leave the world a better place, which extends to his philanthropic endeavours. Place Kangaroo Point is currently supporting stomach cancer research after one of the staff recently battled and survived the disease, as well as melanoma research, inspired by Caulfield’s father’s battle with the skin cancer. They also donate to police, fire and ambulance and local schools.

“I try to find purpose behind it. To me it’s revenue you don’t miss,” he says, revealing his plan for next year is to contribute to homeless support charity Rosies in Fortitude Valley, where he used to help out.

And while baby Krug may not even be six months old, Caulfield is already planning for him to visit homeless shelters and soup kitchens, like he was encouraged to do by his parents as a child. “From an early age my mum made us go to St Vinnie’s and we used to do food banks and my parents weren’t well off, but we’d walk into a home where kids had nothing.

“That was the way we were brought up and I want to be able to do that with Krug. He’s going to have a very nice lifestyle, but he has to learn that there’s a different side to life as well.”

While fatherhood may have changed the way Caulfield dresses, more than anything it’s brought him back to his roots, where humility, respect for others, and an unwavering work ethic remain his strongest values.