Wine Flirts and Wallflowers: The Different Drop Story | #162

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Tom, self confessed wine flirt, talks content, delivery and shares the simplified tech that makes his business hum.

ep 162
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Nathan Bush is a director at eCommerce talent agency, eSuite. He has led eCommerce for businesses with revenue $100m+ and has been recognised as one of Australia’s Top 50 People in eCommerce four years in a row. You can contact Nathan on LinkedIn, Twitter or via email.


Tom Hollings spent the formative years of his career working alongside Australia’s finest artisan winemakers in companies including Cellarforce and Langtons, before taking the plunge in 2013 with his two best mates to launch Different Drop. Different Drop is a digital platform making it easier than ever to explore the wine world and access the most exciting hand-crafted wines on the planet. Nearly a decade on, with industry-leading tech and delivery, thousands of talented winemakers from every corner of the globe, and more than 30,000 happy customers, Different Drop has become the ultimate playground for Australian wine lovers!

You can contact Tom at LinkedIn

In this episode of Add To Cart, we are joined by Tom Hollings from Different Drop.  Tom is a self-confessed wine flirt whose passion turned into an eCommerce business.  With a focus on wines crafted by real people with a sense of adventure and authenticity, Different Drop unearths the best and most exciting drops from producers all over Australia and with some great tech know-how, makes them accessible to all.  In today’s chat we cover a heap of ground from how he and his Co-founder Brett, started the business from Brett’s mum’s garage in 2003, how they pivoted to doing their own delivery and what he learnt from meeting the great Ricky Ponting.  And we ask a very controversial question – ice cubes in red wine. Passable or hell no? Tackling the big issues here. 

“If they wouldn’t want to drink it themselves, then it doesn’t go in…”

Tom Hollings

Questions answered in this episode include
  • How and why did you pivot to doing your own delivery?
  • What’s your approach to content?
  • Tell us your top tech recommendations?

Delivery pivot

“When the pandemic started and Australia post really crumbled under the pressure, we had orders to the next suburb that were taking weeks to deliver. We’re an online retailer that couldn’t deliver.  Even though we had all these other people landing on our site, we couldn’t give a good service.

So, we pivoted into doing our own deliveries, which came about fortuitously. We had a lot of contacts in the industry like sommeliers and wine reps and staff who were out of work and they were asking us if they could help us pack boxes, or do deliveries or whatever. And next thing we know, we had a fleet of well-known Sydney wine traders, whipping around Sydney dropping boxes of wine off everywhere!

And Brett, my business partner, who looks after all of the technology and operational stuff, he found some really neat software called Onfleet, which routes all the deliveries and has great live tracking and communication to the customer. Fast-forward now, we’ve got a little fleet of our own vans on the road, and we’ve really lent into it. 

Someone in a Different Drop shirt and a Different Drop van who knows the product with the live tracking, it was a totally different experience. And every single day we get customers write to us saying how much they love the delivery and it’s become a real competitive advantage for us.”

Crafting content 

“We take all of our own original bottle shots for a start, which is unusual in the industry as it is. Usually, they’re just hodgepodged either from a winery or some competing website. We wanted a uniform look across the site, so we take all of our own images. We have a lot of the imagery of the producers. That’s really important to us. We’re trying to show that these are made by real people. That’s always the story with wine, but it’s not always the reality.  A lot of wine sold is made in a big factory somewhere. These are made by real farmers. And really, the best way for us to get that across is visually. 

And then probably the biggest part of it and the hardest part is we write our own original copy on each wine too and each winery and that’s a longer form, anywhere from three to five paragraphs of proper wine copy.  It was just me in the beginning, but I’m a rubbish writer.

So these days, we’ve actually got a team of external writers we’ve put together,  people that write for other publications, wine reps, sommeliers. A couple of winemakers that just love wine can write a bit and we’ve got them all plugged into this system. We’re using some software called Airtable which is a database management software. It’s really cool. And again, it plugs into Shopify.”

Wine geeks and virgins alike

“If you’re a wine geek or a real power user, so to speak then Different Drop is like Disneyland. There’s so much stuff there and you just do it yourself.  But we don’t want to be too exclusive or elitist or intimidating for just an emerging drinker.

So we put a big focus on navigation around the site. And probably the biggest thing for us has been our mixed packs. We’ve dabbled with different subscription offerings over the years, and they’ve actually never really taken for us. We tend to find our customers want to buy what they want, when they want it. But the mixed packs are an easy way for them to just go, “You know what, I want to try natural wine. I’m hearing all the cool kids are doing it and I don’t know where to start. I don’t know which one’s good or which one’s not.”

We’ve got ‘It’s Only Natural Mixed Pack’ or ‘It’s All Greek To Me Six Mixed Pack’. We’ve got all these silly names we come up with. And there’s probably 50 or 60 different packs on the site at the moment with every different kind of style and lots of different regions and they just aim to be the introduction, starting point, if you’re not sure.”

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