From jazz bars to breakthroughs: how a young entrepreneur turned coaching into his secret weapon
Launching a successful business during a global pandemic would be daunting for even the most seasoned businessperson, but Kent-based hospitality entrepreneur Oliver Kingsley made it look almost easy. Starting a car-boot drinks delivery business in lockdown when still a teenager, over the next five years Oliver grew his business into the South East’s most exciting high-end live music and cocktail lounge experience, the Grapevine Champagne and Jazz Bar brand.
Launching a unique and differentiated service concept is tough
The Grapevine Wine and Jazz Bar in Tenterden opened in autumn 2024 and quickly became ‘Tenterden’s new jazz hideaway’, delivering live music five nights a week. Like its candle‑lit sister venue, The Grapevine Champagne and Jazz Bar in Rye, it prides itself on quality wines, cocktails and table service, complemented by cheese and charcuterie boards from an award‑winning deli.
“We keep that spirit in Tenterden—table service, handcrafted cocktails and an ambience that wows,” says Oliver, who originally hadn’t planned to open a second venue. But he saw that Tenterden was missing what the bar in Rye offered. Oliver explains: “Tenterden lacked a venue combining our three unique selling points that differentiate the Grapevine brand. Diverse live music, elevated table service and unique ambience and décor.”
Oliver and his business partner analysed the town’s data, saw other high-end restaurants and venues thriving plus the evidence of Tenterden’s future growth and visitor numbers, and decided the concept filled a gap. “It had to tick all the boxes,” he adds.
Determined to work on the business rather than in it
After launching the Grapevine Tenterden, Oliver realised he spent much of his time hands on and rarely took time out of operations to think strategically. “With two thriving bars and the planning for a new delicatessen I’d been consumed by day-to-day tasks,” he admits. “I was working in the business rather than on the business, which I knew made it more difficult for me to be more mindful and devote time to critical thinking.
“Having heard about coaching, I realised that a coach could help and sought out Eleanor, an experienced coach and entrepreneur based in Tenterden who understands small to medium sized businesses. Following our initial discovery session, where our rapport was immediate and strong, I knew from her guidance and questions that Eleanor was the right coach to help me change my mindset and look at things from different perspectives.”
Our sessions gave me the time out from my business to step back, challenge my own assumptions, gain clarity and discover answers, all in a safe space. I left with a clear plan and the confidence and motivation to make the decisions needed to carry it through.”
A mindset for delegation and the confidence to take tough decisions
Other challenges facing Oliver when juggling the flourishing business’s demands included prioritisation, delegation and, occasionally, having difficult conversations. Oliver admits his hardworking nature drives him to try and do everything himself: “Working with Eleanor, I’ve developed a mindset that’s enabled me to design a system helping me prioritise and delegate effectively and then follow up without micromanaging. This has freed up time to focus on strategy and planning.”
When a restructuring meant letting a senior manager go, he sought Eleanor’s support before the critical meeting. Their coaching session let him rehearse the conversation, strike a firm yet fair tone and the confidence to accept that it’s quite normal to get emotionally invested in decisions, and that tough decisions are part of leadership.
Making time for success: work life balance
Another challenge was motivation, but not the lack of it, more where to allocate the surplus. Bombarded by social media images of entrepreneurs grinding 24/7, Oliver questioned whether he should be working constantly and felt guilty taking a break: “Everyone on LinkedIn seems to work round the clock,” he notes, “I felt guilty taking a break with loved ones or doing fun things I love, like playing golf.”
His coach Eleanor flipped the question—what does a productive, motivated Oliver, an entrepreneur in their twenties, look like? He realised he was already putting in the hours and seeing the results and impact, and that structuring his day and delegating could free space for leisure without guilt. “I realised I was doing fine.”
Working with Eleanor proved invaluable for Oliver. He describes emerging from each session invigorated, because she doesn’t just coach—she’s an experienced business owner who understands his pain points firsthand which completely changes the dynamics of the conversation. “Unlike friends or acquaintances who are tremendously supportive but can’t relate to my specific pressures, Eleanor offers a structured, empathetic space where I can honestly and openly explore even the issues I never thought I’d share,” says Oliver.
He concludes: “This safe, cathartic environment improved my clarity, unlocked deeper insights, and reinforced my confidence in my own skills and experience to take the right decisions to drive my business forward.”
Success
Launching
a unique and differentiated service concept is tough
Confidence