In 2014, after noticing how expensive good coffee and fresh cafe food had become in Sydney, we set out to create something different. Calypso was founded on the belief that great flavour, quality ingredients, and friendly service should not come with a hefty price tag, making good coffee and meals more affordable and accessible for everyone.
Jenny holds an accounting degree, but her career began in hospitality. In 2012, after several years as head barista at Swagmans Cafe in The Rocks, she moved into the banking sector with Westpac.
By late 2014, driven by a desire to make everyday food and coffee more accessible, Jenny returned to her true passion for hospitality. Together with her husband Derek, she opened Calypso, combining her business experience with a genuine love of great coffee and community.
Derek earned his pharmacy degree from a leading university, but over time he realised his interests were pulling him in a different direction. While working outside the field, he spent a lot of time in cafes and became interested in what made some places feel so natural and welcoming, while others felt a bit disjointed.
He noticed that when a cafe runs poorly behind the scenes, it affects more than just speed of service. It shapes the quality of the coffee, the overall experience, and what customers end up paying. That curiosity led him to explore how cafes could be run more thoughtfully, bringing structure and care together. Calypso reflects that vision: a space built to run smoothly and consistently, serving quality coffee and food at fair prices in a welcoming environment.
