Home to The Successful Founder Print & Digital Magazine 
Advice Articles, Interviews, Founder & Brand Spotlights 
Home of The Most Advice-Feature-Rich Entrepreneurship Magazine Around
Anna Smith of Words With Wine

Meet the Successful Founder: Anna Smith of Words With Wine

Anna Smith is the founder of Words With Wine, the UK’s first book and wine subscription box. She is 30 years old and lives just outside of Edinburgh, Scotland. Prior to Words With Wine, Anna worked as a Head Hunter and before that, she had her own Wedding Planning company in Scotland. Her mission is to get more people to take some ‘me time’ by enjoying a book and a glass of wine. All whilst trying new genres of books from new authors and trying new styles of wine.   We were delighted to catch up with her to learn more about her entrepreneurship journey.

Can you tell us a little about your background and the company?

Before lockdown I was working as a Head Hunter for Marketing and Communication roles. I was put on furlough then made redundant due to the lack of jobs and hiring during the pandemic. I came up with the idea for Words With Wine on December 30th 2020 and after months of research I launched in April 2021. Words With Wine is the UK’s first book and wine subscription box. Each box contains a new book, a paired full size bottle of wine, an information card with facts on the book and wine and how to pair your wine with food. Along with membership to an exclusive online bookclub. Membership options are monthly, bi-monthly (both the book and wine of the month) or a gift box (book and wine of a previous month). We also have a limited edition Christmas box available in November and December with some little added extras.

How did the idea come to you for the company?

Prior to the pandemic I attended a separate book club and wine club but lockdown made it difficult to carry on with both clubs and I got stuck into the habit of only reading crime novels and sticking to the same bottle of red wine. I wanted to get back to trying new genres and different wines but couldn’t break the habit. I started googling to see if there was a company that would send me a new book and bottle of wine every month but couldn’t find one. So I decided to start it myself. I did a lot of researching until I was happy with the right suppliers and the message I wanted to get across to the customer. 

How did you achieve awareness?

Mainly through social media. I spent a lot of time growing the social media accounts, getting good images and contacting influencers to help promote the boxes. I ran a competition to win a box and a candle with an established small company also in Edinburgh and contacted my local news papers. I was then approached by Georgia at farq media about collaborating on PR. We decided to work together and she has managed to get Words With Wine into some great publications including The Sun and Sheerluxe. I also started using paid ads recently on social media.

How have you been able to gain funding and grow?

I have not applied for any funding. I put my savings into the company and all profits have been reinvested to help grow and attain more stock.

What are the key successes?

On launch day we had 27 people sign up to a subscription. For a brand new company I thought this was a great achievement.

We managed to grow to over 1500 followers on Instagram within the first 6 months.

What were/are the challenges and how have you overcome these?

The biggest challenge is getting the word out there about Words With Wine. We need more people to know about it. We are still in the first year of business so still fairly unknown. The best way to get the name out there has been through PR and paid ads on social media. Using influencers with the same target audience has also been very helpful.

What are your plans now/for the future?

The plan over the next 3-5 years is to grow the business. Get the number of subscribers up per month and launch more limited edition boxes based on holidays such as Christmas and Mothers day. I have a few plans for events to come in the future but for now the main focus is growth.

What would you like to share with others to encourage them to start their own entrepreneurship journey?

Go for it. There’s never going to be the ‘right’ time to start. It you are passionate about your vision, believe in it and are willing to put the time and effort into it, then go for it. Even if you start it as a side project to begin with, now is your time. No matter what you do, you are never going to be everyone’s cup of tea. So do what feels right to you, do lots of research into your audience and what they like and want. But most of all, enjoy the process. The end goal will always be changing because of progression and pivoting, so make sure you enjoy the steps along the way.

Can you share you top 5-10 tips for entrepreneurial success?

Research. Research everything and anything to do with your business. Suppliers, competitors, your audience.

Join a network for small business. You will have questions and sometime google isn’t as helpful as you think. Speaking to people who are in the same position or have been and can give you advice can be more helpful.

Enjoy the process. When you hit your goal, there’s always going to be a new goal. Don’t spend all your time chasing the goal and not enjoying the process of getting there.

Invest in a good website. Either take the time to learn how to do it properly yourself or hire a professional (depending on budget). Your website is one of your biggest selling points, you could have the best product on earth but if you website is difficult to use, customers will drop off.

Keep on top of invoices and accounts. There’s nothing worse than getting to the end of a financial year and having to spend weeks finding and pulling together all your receipts.

Make sure you take some ‘me time’. Go for a walk, go to the gym, read a book. Take some time away from your job. Most of the time my best ideas come to me when I’m out walking the dog, not thinking and forcing the ideas to come.

Who are the 5 people who inspire you the most?

Lucy Hitchcock (@lucyhitchcock_) – Founder of Sassy Digital and Partner In Wine. Lucy has put everything she has learned from her first company Sassy into her second and has proven massive success. She also shares her journey along the way, so you can give it a go yourself.

John Burke and Jon Hulme (@craftginclub) – No surprise here. The boys made a huge impact on the subscription box industry when they launched in 2017. And have grown the company to a great success over the few years they have been running.

Steven Bartlett (@steven) –  Founder of Social Chain at just 22, he took the company public on 2019 with a value of $200 million.

Grace Beverley (@gracebeverley) – Founder of Tala and Shreddy. Grace grew a following on social media as an influencer before spotting a gap in the market and launching an affordable and sustainable gym brand, which also feels amazing to wear.

My Dad (no Instagram unfortunately) – At the age of 43 he decided to change his whole career and open a franchise of Dominos Pizza. He put everything into it, made it successful and comfortably retired at the age of 60.

What are your favourite inspirational /motivational quotes?

“Your never too old to set up another goal or to dream a new dream” – C.S. Lewis

“Just believe in yourself. Even if you don’t, pretend that you do and at some point you will” – Venus Williams

What are your social handles and website links so our readers can connect with you?

Instagram – @wordswithwineuk

Facebook – @wordswithwineuk

Pinterest – Wordswithwineuk

Tiktok – @wordswithwineuk



TSF Reporters

The Successful Founder Magazine is the go to feature-rich magazine for founders on all stages of their entrepreneurship journey .