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Q&A with Lucky Pineapple Founder, Hayley Simpson

Q&A with Lucky Pineapple Founder, Hayley Simpson


Adding a bold touch of glitz and glamour to any occasion, Lucky Pineapple is a mobile cocktail bar specialising in fun yet fancy cocktail experiences. Serving up reimagined cocktails, prosecco & beer from their giant golden pineapple trailer, their presence at any party is a guaranteed show stopper.

We interviewed the founder of Lucky Pineapple, Hayley Simpson to find out how it all started.

1) Who is behind Lucky Pineapple?

Lucky Pineapple is me – Hayley Simpson – as well as a team of outrageously charming bartenders who support me at events on an ad hoc basis. They are brilliant! Day to day, it’s just me running things behind the scenes, but I have a lot of very talented friends who I love to involve in various projects – from graphic designers, through to drinks consultants – most of whom I’ve known from a lifetime of working in hospitality.

Hospitality is in my bones. From working front of house in cafes, to working my way up to a Head of Marketing & Brand Comms position for The Breakfast Club cafes & bars. I joined them when they were two cafes, leaving 9 years later when the business was 11 cafes and 5 cocktail bar sub-brands. I am their biggest fan and feel very LUCKY to have experienced so much with them.

2) Where did the idea for Lucky Pineapple come from?

Having seen the demand for creative decor, styling, and party props in live events, I wanted to build a show-stopping structure that also so happened to serve drinks. The bar is often the most functional point at any event, and I wanted to have fun with this. You could say it’s a two in one concept, but I like to think of it as one of a kind!

Lucky Pineapple has grown to be more than just our golden pineapple trailer bar structure. Since launching just under a year ago, we now have two bars that cater to all kinds of events in both the public and private spaces – from festivals and pop-ups: to weddings and corporate parties. I have a few more concepts up my sleeve but I am trying to balance my big ideas with measured and sustainable growth! We are still a baby business!

In a nutshell, Lucky Pineapple delivers a super-styled, aesthetically charged cocktail experience – from the bar structures themselves; to the break out spaces we style around them; to the delicious & high quality – yet super instagrammable (sorry for the cringe word ha!) cocktails we serve – all of which can be tailored around party themes or personalised.

3) What’s your mission statement?

Service, style & soul is a phrase I use over and over with Lucky Pineapple.

Service – we operationally deliver a very necessary party function, professionally and with flair. Offering a super smooth and personal end to end event experience as well as serving up high-quality cocktails made with the best ingredients and products.

Style – I want to grow Lucky Pineapple to be known as the most stylish and show-stopping cocktail party experiences in the live events market. Fun and fancy occasions that are special and memorable – even if we’re setting up in your office or in the middle of a field! The devils in the details, and we bring style through in everything from the bars we serve from, through to personalised/customised touches within the cocktails themselves.

Soul – All the style in the world means NOTHING if it’s superficial. How we make you feel is just as important as how we look, and it’s a top priority to hire amazing talent that represents the brand awesomely behind the bar. There are bar agencies that expertly blur into the background, performing a function and you hardly notice them. Those have their place without a doubt, but we will never be that. We have the honour of sharing some of people’s best occasions – festivals, their wedding day… it’s my number one priority to have the most charming characters on my team, who will heighten our guests’ experiences and make them feel SO good!

Similarly, this extends to how I look after my team. I am inspired by the owners of The Breakfast Club who treat their staff incredibly – creating jobs, amazing opportunities and being a real leader in showing how great a Hospitality job can be. If I can build a business that can afford to do even a handful of the amazing things they do, I know I am achieving what I set out to do.

If we deliver on those three key areas consistently as we grow, then I know we will smash it!

4) What’s a typical day at Lucky Pineapple?

In a life before the Coronavirus lockdown, days revolved around our upcoming events and preparing for them – what is needed for a wedding or corporate party is totally different to a pop up in a fashion store or a festival! Not one day is the same, but I am fairly strict on making space to work on the business instead of in it – especially in terms of marketing, outreach and relationship building. Growing awareness of Lucky Pineapple is the number one goal less than 1-year in.

5) What’s the best thing to order from Lucky Pineapple?

For private events, it very much depends event to event, mostly around our client’s preferences. For public events, we’re all about the classics served with a tropical twist. Favourites include coconut and ginger margaritas, frozen hibiscus daiquiris or a pineapple gin sour! We offer one customised cocktail for each of our private events. This could be a brand logo on an edible martini topper, or a heat-stamped orange peel. These tailored little details are a massive part of the Lucky Pineapple experience. For public events we incorporate these touches using Lucky Pineapple branding – people love it and always take pictures!

6) Are there any exciting plans for Lucky Pineapple?

I won’t lie, Coronavirus and the impact that it’s had on hospitality and live events hit me initially like a ton of bricks. I was just about to embark on a defining summer season for Lucky Pineapple. It is gutting, but it’s gutting for everyone. I gave myself a week off to gather my thoughts, grieve a little, and get my ducks and in a row before getting stuck into new projects to further our growth, outside of big live events.

I am getting ready to launch our umbrella brand called ‘The Lucky Party’, of which the cocktail bars, like Lucky Pineapple, and future branded concepts will sit under. The Lucky Party will also be the brand behind new creative cocktail experiences and income streams coming over the next few months – from a super-luxe cocktail subscription box membership launching in July, to cocktail masterclasses and workshops in London & Brighton once social distancing measures have eased. I am excited and feeling positive, to say the least!

Coronavirus is devastating! It won’t be an easy ride, but we will get through it. In a life after lockdown I can’t wait to get back out there with the bars and my team, and I look forward to the next time the Lucky Pineapple trailer can shine in a field! When the party is in full swing, music is playing, guests are relaxed and happy, the sun has nearly gone down, and the lights are twinkling. There is no better feeling… it really is what this is all about!

Bring the party home and recreate your favourite cocktails with one of Lucky Pineapple’s cocktail party boxes here.

Lucky Pineapple Cocktails

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