#FemaleFounders - Charly Lester

Charly Lester - co-founder of A League of Her Own

Charly Lester is the co-founder of A League of Her Own, an online learning platform and community designed to encourage more women to become entrepreneurs. Charly founded the organisation with Caroline Brealey, after the pair discovered they had faced similar challenges starting their first businesses. Charly is the founder of The Dating Awards - a global set of industry awards for the online and offline dating industries. In her spare time, Charly plays roller derby for Romania (she is half-Romanian) and is training for her first full Ironman triathlon.


1. Who inspires you?

Pretty much anyone who has found a niche area which they are passionate about, and really made their own. My friend Alix Fox is a great example of this - she's a leading sexpert, and has really come to own the 'sex' space, just because she is so interested in all facets of the subject. If you care enough about a subject, and really understand its nuances, the opportunities can be limitless - something Alix has proven!


2. What gets you out of bed in the morning?

Honest answer? My two dachshunds! They are the most insistent alarm clock I've ever owned! A necessity when you're super nocturnal and run your own business! I often work until 2 or 3 in the morning, because I've always been most efficient later in the day.


3. What keeps you awake at night?

Ideas! I always have my best ideas just when I'm dropping off to sleep, so I keep a notebook on my bedside table. My first business came from a late night brainwave.

4. What’s your signature meal and who would you cook it for?

I'm such a terrible cook!  I genuinely live off M&S ready meals!  I justify it by saying my time is probably better spent elsewhere, given how bad my cooking is. I live alone, and one of my requirements in a partner is that he can cook better than me!


5. How do you manage your time?

I'm a big list writer. Every month I start a new notebook where I write down my goals for the month. I then break these goals down into priorities for each week, and each day, and then try to ensure that every day I'm doing something productive towards those goals. I'm quite good at also setting time aside to exercise, and do non-work related stuff, as I think you have strike a balance, otherwise you burn out.


6. Best bits (s) of advice ever received?

To appreciate the value of my own time. Work out how much your own 'hourly rate' is, and don't waste time doing stuff that you can outsource to someone else cheaper - this is how I justify paying for a cleaner! But seriously, you can't do everything yourself and so it's really valuable to be able to work out what you can outsource and which parts you need to do yourself.


7. What is the best and worst purchases you’ve ever made?

Best - I never regret 'investing' in an expensive work dress. I see it as investing, because sometimes a really good work outfit gives you confidence. It's like armour. It helps you feel the part - and we all know how female entrepreneurs are constantly plagued by the imposter syndrome. I do quite a bit of TV - I was a guest judge on The Apprentice, and quite often get called in for shows like Newsnight when Tinder hits the headlines - and so it's important to have a few outfits I feel really confident and comfortable in, as TV is nerve-wracking enough! I should also point out, all my favourite dresses are from female-run British companies! I'm a big fan of Goat and Madderson.

Worst - As for 'worst purchases' ... over the years I'm sure I've bought lots of things I didn't actually use. Probably the most irritating was a double bed for a new house I was buying ... and then the house sale fell through. The bed is still in my friends' garden shed ... oops!

8. What is the closest thing to magic?

Love! I work in the dating industry, so I really have to say that, don't I?! That, and the amazing feeling when you make a huge chunk of money! Sorry - but it's true. You feel like you want to do a little jig! I love that feeling!


9. Do you have a mentor? What value do you think a mentor brings to a business?

I don't have a formal mentor, but I have a lot of peer mentors. It was something I realised early on - I was working on my own, and none of my friends really understood the challenges I was facing, or the industry I was working in. By finding peers in my industry who were in a similar position to me, I made a group of new friends who I could sound ideas off, tackle problems together, and collaborate with. Caroline Brealey was one of these peers - we both ran companies in the dating space and when we met, we realised we'd faced similar problems when we were starting out. It was these discussions which led to us launching 'A League of Her Own' together.

Nowadays both Caroline and I work as mentors for several female entrepreneurs. It can really help having someone who is a couple of steps ahead of you on the path, who can pass on words of wisdom, and let you know whether something is or isn't normal or to be expected.


10. What unusual food combinations do you enjoy?

It's not really a food combination, but I'm dangerously addicted to Lotus Biscoff spread! I can eat the stuff by the tablespoon!


11. How can female entrepreneurs further support each other?

Where possible, when I'm outsourcing stuff for my own business, I try to use other businesses run by women. I have a fab female photographer and videographer who work at all my awards shows, and for A League of Her Own we used female entrepreneurs for our logo and both the front and back ends of our website.

I think it's also really important to celebrate each other's successes, and not be daunted by the successes of others. In the League we try to interview as many female entrepreneurs as we can - not only to showcase their achievements, but also to show our members that female entrepreneurs (and their businesses) come in all shapes and sizes.

Inspiration Cover Pic.jpg

12. What’s something that will always be in fashion, no matter how much time passes?

Manners! They will never go out of fashion. And people need to remember that. In this day and age, where we are constantly communicating, and can use emojis as responses, people sometimes forget the basic stuff. Use people's names, say thank you, be polite. You won't be remembered for it, but if you forget your manners, you will be remembered, and for all the wrong reasons!


13. What was the last thing you did that made you really proud?

At the end of last year I was at the Oxford Union in their debate on the existence of true love. It is genuinely one of the most daunting things I have ever done. I had to prepare an 8 minute argument, knowing I was debating against professors, and being watched by a hyper intelligent audience. The speech went well (though watching the footage, I can see how nervous I was - and I do a lot of public speaking!) and I was absolutely buzzing afterwards. The audience vote with their feet by walking through a door. Watching all the people who agreed with our team walk through our door was incredible.


14. If you were to give advice to a fellow female entrepreneur what would it be?

Stick it out. There will be tough days, weeks and months. But they make the good times so much better. You need to graft hard to appreciate your successes. And network - reach out to other women in your industry and in your situation. Create a support network around yourself. You shouldn't have to feel alone.


15. What does success look like to you?

We just launched 'A League of Her Own' and it really is Caroline's and my baby. It's so close to our hearts because it is specifically designed to tackle the challenges and issues we both had when we were first starting out in business. As a result we are really passionate about it. For us, success is creating a huge community of female entrepreneurs, who inspire each other. We want the organisation to become a movement in itself - which the members themselves guide. We're five months in so far... I can't wait to see what it looks like when we're five years in!



Website - www.leagueofher.com | www.thedatingawards.com

Social - Twitter | Instagram | Facebook