‘I don’t like the word failure’: How James Kennedy turned a small family business into an empire 

The thriving luxury watch market is showing no signs of slowing down, and CEO James Kennedy is more than ready for whatever it throws at him. 

James Kennedy always assumed he would end up running the family business. What he couldn’t have predicted was how good at it he would prove to be. 

Founded by his parents in 1976, Kennedy Watches and Jewellery was a small boutique in Sydney’s Double Bay that “provided a good life” for the family for over two decades. The younger Kennedy speaks fondly about hanging around the shop as a kid, helping as a teen and in his early 20s before flying the coup for a career in finance. 

Following his father’s death in 2008, a then 28-year-old James left a promising trajectory at Deutsche Bank to carry on the family legacy, bring their analogue business into the digital world and drag the rest of the Australian luxury watch market along with it. 

“Even then, the whole industry was archaic and digital retail hadn’t fully taken off yet,” he says. “But the business also needed a shake-up, and some tough questions needed to be asked.” 

Though full of ideas, James could see that his immediate priorities were interrogating and stabilising the existing business. He took his time getting to know the ins and outs of his parents’ lives’ work and reflecting on what he’d learned at Deutsche Bank about structuring and managing the day-to-day of a thriving corporation. 

“I’m an ambitious guy,” says James. “I have drive and desire and I’ve taken my share of risks. But taking on a business, especially when it’s your family’s business, is like playing with live ammo: if you get it wrong, you wear the consequences.” 

Fifteen years later, the consequences seem altogether positive. James has grown Kennedy from two small Sydney boutiques to 10 stores in three cities. He attributes expanding his parents’ brick-and-mortars beyond their wildest imaginings to technological advances, savvier consumers and an ever-evolving industry. 

“It’s a radically different time to mum and dad’s days, requiring an entirely new skill set,” he says. “The local market was still quite immature when I took over but now consumers are driving disruption, demanding different watches, materials, and technologies, and understanding that helps me propel the company forward.” 

James acknowledges that it hasn’t been all smooth sailing, that his success hasn’t been linear or without missteps. Like all of us, he’s been cocky at times, taken ill-advised risks, and made decisions that haven’t panned out. But after 15 years at the helm, he’s philosophical about it. 

“I don’t think my wins would have come without my losses and I don’t like the word failure. Everything is a learning experience. Everything can lead to something else, something better, and the key to success is making the most of your highs and limiting the impact of your lows.” 

This willingness to stumble and a refreshing humility have served the business well. He says he’s learned to be more disciplined and risk-averse but laughs when told he’s been called a bold and visionary leader. “Only when I get it right,” he jokes. He counts his wife and son as his “real wins” but does admit to having gifts for predicting trends and identifying opportunities, and there is no shortage of opportunities in his trade. 

The global luxury watch business was valued at over USD$40 billion in 2022 and is expected to exceed USD$60 billion by 2032. It thrived in the post-Covid luxury goods frenzy, survived the post-post-Covid cooling off period, and despite cost-of-living crises everywhere you turn, continues to go from strength to strength. 

“Wealth doesn’t go away, it moves around” 

James Kennedy

Plus, almost a decade after the advent of smartwatches, then widely presumed to be the death knell of mechanical timepieces, new demographics continue to embrace them. 

“Smartwatches helped the industry by reinvigorating worn timepieces. We even see people wearing a smartwatch on one wrist and a mechanical watch on the other. Smartwatches brought in a younger market and wealth is getting younger.” 

So, what about eCommerce? Luxury eTail has come a long way, but most major luxury watch brands still don’t sell directly online. While Kennedy has a strong eCommerce platform, James says most customers still want to touch and try watches before purchasing so his focus is retail. More stores are planned across the country, including concept stores with expanded jewellery offerings and new categories such as fragrance and stationery. 

“Come into a Kennedy Boutique, spend an hour or two having a luxury experience without necessarily purchasing luxury-priced items.” 

When asked what the future holds for him, the watch soothsayer is excited yet uncertain. 

“I had my first evolution in the last 15 years and now it’s the next phase. Let’s check in in another 15 and I’ll tell you how it went.” 

We’ve set our watches to do just that and look forward to hearing about James and the Kennedy journey from here. 

For more information, visit https://www.Jameskennedy.au