Inspirational Woman: Charly Lester | Co-Founder, A League of Her Own

Charly LesterCharly Lester is the co-founder of A League of Her Own – an online learning platform and membership site for early stage female entrepreneurs and women with a business idea.

She is the CEO and Founder of The Dating Awards, an international set of awards for the dating industry, and she is the former Global Head of Dating for Time Out Magazine.

Charly teaches business classes at The Guardian and was a guest judge on the final of The Apprentice in 2015. When Charly isn’t working, she’s training for her first full Ironman triathlon.

Tell us a bit about yourself, background and your current role

I’m the co-founder of an organisation called A League of Her Own which is an online learning platform to support early stage female entrepreneurs and women with a business idea.

I have been running my own business for the last four years – I run international Awards for the online and offline dating industries – and together with my co-founder Caroline, we designed  A League of Her Own to tackle the problems which we faced when we were first starting our own businesses.

Did you ever sit down and plan your career?

Haha no, not at all.  I fell into the dating industry when a blog I wrote as a joke went viral.  It led to me working at Time Out and the Guardian, and I spotted a gap in the market and just decided to launch my first business – The Dating Awards.  I ended up being seen as a dating expert, and then as an expert on areas of business marketing, and that led to me starting A League of Her Own.  Something I’ve learned about business is that it pays to be reactive sometimes.  Which can be hard if you’re normally proactive and a planner!  That said, I always start the year with clear goals and every month, week and day I plan with lists!

Have you faced any particular challenges along the way and if so, how did you deal with them?

There are always challenges in business.  An idea won’t take off the way you expected it to.  Something will cost more than you thought, and you have months where you make a loss.  At first I used to think that was a direct reflection on me and my business, but then the more business owners I spoke to, the more I began to understand that it’s just an everyday reality of running a business.  There are swings and roundabouts, and every experience will make you stronger.  It’s clichéd but you really do appreciate the successes more when you’ve felt the lows too!

If you could change one thing for women in the workplace, what would it be?

Equality, equality, equality.  We just are not there yet.  There are more women than men in the population, and yet that isn’t represented in boardrooms, and C-suites.  We need to keep pushing for parity in all areas.

How do you feel about mentoring? Have you mentored anyone or are you someone’s mentee?

I’ve mentored a number of women in business – both formally, and more informally (we have a Facebook group for League members, where they can ask questions and get feedback as they grow their businesses). I’m a huge fan of women helping other women.  If you are even a few steps ahead of someone, turn back and help lead the way.

What has been your biggest achievement to date?

Probably being a judge on the final of the Apprentice.  That was a pretty cool experience!  That and working for myself for the last 7 years, and not having to ‘return to a day job’.  I have so many people in my life who still don’t really understand what I do, or how I can pay the bills.  But when you work for yourself, every bill you pay from your own steam and your own ideas is a real success!

What is your next challenge and what are you hoping to achieve in the future?

So we just launched a book – ‘The Female Entrepreneur’ which is a step-by-step guide to starting your own business.  It’s been so exciting holding it in my hands, and seeing people on Instagram taking photos of it and saying how much they are learning from it.  We also have two new podcasts which have been keeping me busy.  I have a second book in the pipeline – Modern Marketing for Start-Ups which will come out later this summer, and who knows? We would love to grow A League of Her Own into a huge global community of early stage female entrepreneurs.

How can you get involved with A League of Her Own?

Head to  Our blog is full of free resources, including workbooks, blog posts, videos and podcasts.  We produce monthly modules which you can either buy individually – on topics like blogging, business branding, Instagram, getting investment, podcasting and doing your own PR – or you can come and join our community.  You get a new module every month, which includes video training, 3 expert interviews, a workbook and FAQ sheet, and we do a live Q&A session each month inside our Facebook group.  If anyone has any questions they can also find me on Twitter and Instagram @leagueofcharly.

Related Posts