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Markets & Martinis: The Inaugural Evening
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Cotswolds Lifestyle

Markets & Martinis: The Inaugural Evening

Elliott Wakefield5 min read

Last Wednesday evening, a sold-out crowd gathered at Club Ocho in Cheltenham for the inaugural edition of Markets & Martinis — an evening I’d been planning for months and one that, I’m thrilled to say, exceeded every expectation.

The concept was simple: take the things I spend my days thinking about — property styling, market positioning, the difference between a house that sells and one that sits — and turn them into a social evening. Not a seminar. Not a lecture. Just cocktails, some laughs, and things that make you think gosh, that is a good idea.

Club Ocho set up for the Markets and Martinis evening, with the Elliott Wakefield branding on the big screen

The Setting

Club Ocho was the perfect host — a private members’ club set within a beautifully renovated Regency townhouse on Imperial Square, in the heart of Cheltenham. We held the evening in its speakeasy jazz bar, a room normally reserved for members only — all sculptural arches, velvet seating and a sense of occasion the moment you walk down the staircase. It felt right for what we were doing: prestige property deserves a prestige setting.

Descending the staircase at Club Ocho, Cheltenham

Love It or List It

The heart of the evening was what I called Love It or List It — Cotswolds(ish) Edition. Armed with cocktail paddles, the audience voted on a curated selection of properties — some that sold for a fortune, some that languished on the market for 200 days wondering what went wrong. We looked at what made the difference: was it the photography? The styling? The pricing? Or something less tangible — the feeling a property gives you when you walk through the door?

Elliott Wakefield presenting the Love It or List It segment at Markets and Martinis

I also shared the story of our own home — the before-and-after transformation that first taught me how profoundly styling and spatial re-thinking can change a property’s appeal. Ink walls in the snug? Brave, perhaps. But every note deliberately cohesive. The audience seemed to agree.

The Atmosphere

What I hadn’t quite anticipated was the energy. The event sold out, and we even had walk-ins on the night. The vibe was more dinner-party-with-a-projector than conference — people chatting between segments, comparing notes on the properties, debating whether a particular kitchen was worth the premium. Exactly what I’d hoped for.

A packed audience at Markets and Martinis, cocktails in hand
The sold-out crowd at Markets and Martinis

The candid shots from the night capture it better than I can describe — these were taken in the moment, not by a photographer, and I think that’s what makes them honest. Real people, real reactions, real cocktails.

Guests deep in conversation during the interval

What the Audience Told Me

The feedback afterwards was incredibly generous — but the two things people kept saying were: “more listings next time” and “can we have a Q&A?”. Duly noted. Both are going straight into the planning for the next edition.

Watch This Space

Because there will be a next edition. The format works, the venue is superb, and — most importantly — the conversation it started is exactly the kind I want to be having: not about bricks and mortar, but about lifestyle, feeling and the art of presenting a home at its absolute best.

Elliott Wakefield backstage before the show

If you missed this one, don’t worry. Keep an eye on the site and my social channels — the next Markets & Martinis will be announced in due course. In the meantime, if you’d like to talk about how to present your property for maximum impact, you know where to find me.

All photographs are candid shots taken on the night — because the best evenings are the ones you forget to hire a photographer for.

Elliott Wakefield

Elliott Wakefield

Member of the Chartered Institute of Marketing (MCIM) and Prestige Property Expert in Cheltenham and the Cotswolds. Licensed with The Prestige Property Experts.

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