This National Family Business Day, we’ve been reflecting on what it really means to run a family business – the good parts, the difficult parts, the long days juggling kids and business, the dinner-table discussions and, ultimately, why we continue to do it together.
Next year marks 20 years since Rosie and Griff Cupitt opened Cupitt’s Estate in 2007. What began as a winery and small 30 seat restaurant has grown and changed considerably over those two decades, but family remains at the heart of it.
Today, the next generation of Wally and Tom, along with Tom’s wife Libby, are all deeply involved in the business, bringing their own skills, ideas and perspectives to what Rosie and Griff started.
And, as they’ll readily tell you, working with your family isn’t always straightforward.
“The dinner table often becomes the boardroom, and a nice meal can rapidly turn into a passionate discussion,” says Tom.
Anyone who has worked with family will probably recognise some version of that. There’s not always a clear line between work and home when the people sitting beside you at a family dinner are also the people you need to make decisions with the next morning.
But Tom says that closeness also brings something difficult to replicate in any other business.
“There’s a deep sense of trust that only comes from decades of family bond. There’s a great feeling in having three generations involved, building something together that supports not only our family, but our team and their families too.”
For Libby, family business has also meant watching another generation grow up around Cupitt’s.
“Our kids have been brought up inside the business. It’s all they know. They’ve been bribed with endless bowls of chips and ice cream to tag along to work with us every school holiday and weekend.”
It’s a funny part of the Cupitt’s story, but also a very real one. Weekends, school holidays and busy periods don't necessarily mean time away from work when hospitality is the family business.
“I genuinely hope they don’t resent us for it one day, but I think they’ll understand it was never really a choice; it’s just what family business looks like. The ice cream helps.”
There are also moments that make those sacrifices worthwhile.
“I see the pride they have in what their grandparents created, and that their friends love coming out here on weekends to run around and eat pizza. Those are the days I feel particularly proud of the community space we’ve built.”
For Wally, being fully invested in the family business comes with challenges, but also a strong sense of purpose.
“It’s challenging, but incredibly rewarding. It only works because there’s respect for each other and a real commitment from everyone in the family.
“For us, it feels like we’re building something more than a business. It’s our life, it’s a vocation, and hopefully it’s something we can hand down through the generations.”
That idea of generations is particularly significant for the Cupitt family.
While Cupitt’s Estate will celebrate its 20th anniversary next year, the family's connection to hospitality and farming stretches much further back.
A story that started before Cupitt’s
Rosie’s grandmother had a restaurant, making Rosie the second generation of her family to work in hospitality and her children the third.
Rosie herself is a winemaker, while Griff is a fourth-generation grazier who continues to run cattle on the farm today.
When they opened Cupitt’s in 2007, they brought those different family traditions together.
“We wanted to build something that combined our love of food and wine with the beautiful farm that we call home,” Rosie says. “At the time, we were simply taking a leap of faith and creating something of our own.”
Almost 20 years later, she and Griff have had the opportunity to watch the children take on the day-to-day running of the business.
“They bring their own ideas, energy and personalities to the business, while still carrying forward the values and foundations that we established back in 2007.”
For Rosie, that's one of the most rewarding parts of what they created.
“You start something because you have an idea and a passion for it, you work incredibly hard to build it, and then one day you look around and realise that the next generation has taken what you started and is making it their own.”
The people beyond the Cupitt family
Of course, Cupitt’s has never been built by the Cupitt family alone.
Over almost two decades, many hundreds of people have been part of the team. For some, Cupitt’s has been a first job. Others have built careers here, learnt a trade or skill, moved into leadership roles or gone on to take what they learnt into other parts of the hospitality, wine and tourism industries.
“The people who come through this business help us immensely, and I hope just as much that we give something back to them,” says Libby. “Real opportunities to grow, to learn a trade, follow a passion, and to be trusted with more than they expected.”
Tom sees that connection extending beyond current employees too.
“We love the connection we have with our team and the Cupitt’s alumni, and the bond that forms between our family and theirs.”
It's one of the reasons supporting a family business has an impact well beyond the family whose name is on the door.
Still writing the story
Next year, we’ll have plenty of reasons to look back as Cupitt’s Estate celebrates 20 years.
There have been changes, challenges, mistakes, new ideas and plenty of passionate family discussions along the way. The business today looks very different from the winery and restaurant Rosie and Griff opened in 2007.
But perhaps that’s exactly what a family business should do. We keep evolving as new people and new generations put their own mark on it.
As Rosie puts it, “We haven’t simply handed them a business. We’ve handed them a history, a set of values, a lot of lessons, and probably a few stories about the mistakes we’ve made along the way! But ultimately, they are creating the next chapter.”
This National Family Business Day, we’re grateful to everyone who has been part of that story - our family, our team past and present, our local community, and everyone who has chosen to visit and support Cupitt’s over the years.
Almost twenty years on, we’re still a family business. And we’re still writing the story.
