In this interview with Jennie Bayliss we learn about her extensive entrepreneurial journey and latest innovative venture, Letterbox Cocktails. Jennie shares how her path began over 15 years ago with an award-winning virtual PA company. Over the years, she has expanded with a portfolio across premium drinks, mentoring, and programme leadership.

A major turning point came when Jennie's team entered and won the Business Show £100,000 VIP Launchpad competition. This transformed Letterbox Cocktails from a side hustle into a fully-fledged business. Since then, the brand has gone on to win the Best New Business Award at the SME Bedfordshire Awards and has reached the finals of the Best Business Women Awards, recognised for its innovation, packaging, and product excellence. She also ran a successful crowdfunding campaign, which not only raised essential funds for branding and packaging, but also boosted visibility.

Jennie explains the inspiration behind Letterbox Cocktails: her desire to move away from service-based businesses to a tangible product, redefining luxury in the ready-to-drink cocktail market. The unique concept of cocktails that fit through a letterbox caters to time-poor consumers. The company has already expanded into weddings and seasonal gifting, and expects growth in corporate clients.

Looking ahead, Jennie shares her plans to secure investment, scale the business toward £8–10 million annual turnover, and exit within seven years. She is aiming to outsource production as a practical growth strategy and sees awards and PR as key tools for credibility and exposure.

Throughout the conversation, Jennie highlights the importance of building strong networks, staying adaptable, and avoiding perfectionism in the startup phase. Her advice for entrepreneurs is to focus on visibility, customer needs, and execution over details like logos. For her, success comes from persistence, risk-taking, and leveraging every opportunity, from awards to mentoring.

This is an episode with some impactful lessons for both budding and established entrepreneurs.

{2:05} How Jennie ended up in the world of cocktails.

{5:45} Going through a crowdfunding process.

{7:12} Why Jennie chose to start a cocktails business.

{9:12} The uniqueness of the product and the benefits of home delivery.

{10:55} The best-selling cocktails.

{11:32} Letterbox Cocktail's typical clients.

{12:25} The preparation for VIP Launchpad.

{14:28} Did Jennie expect to win at VIP Launchpad?

{15:21} Winning the Best New Business at the Beds SME Awards.

{16:33} The PR Jennie has gained through awards.

{18:22} Longer term plans for Letterbox Cocktails.

{19:22} Producing in-house v outsourcing.

{20:07} Jennie's business tips.

{22:30} The essential need to do something different.

{23:05} Jennie's advice for startups.

{25:46} Stop procrastinating - take action!

Connect with Debbie at: https://thebusinessawardsshow.co.uk

Connect with Jennie: https://www.letterbox-cocktails.com/

LinkedIn: https://www.letterbox-cocktails.com/

Facebook: https://www.facebook.com/letterboxcocktails1

Instagram: https://www.instagram.com/letterbox__cocktails/

TikTok: https://www.tiktok.com/@letterbox_cocktails

YouTube: https://www.youtube.com/@LetterboxCocktails