I run an online learning platform for female entrepreneurs, and regularly teach classes on social media, PR, blogging and business. Got a business or start-up question? AMA!

Charly Lester
Mar 8, 2018

To celebrate International Women's Day, I'm running my first ever AMA! I am co-founder of A League of Her Own, a platform and support network for female founders, designed to encourage women to start their own businesses, take their business to the next level, or turn an idea into a reality.

I run Masterclasses for the Guardian newspaper on different areas of business, and have 3 companies of my own, which I've been running internationally for the past 4 years.

I'm happy to answer any business or start up questions, or questions related to how I started my entrepreneurial journey!


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Conversation (63)

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How has starting your business and living your purpose balanced out to where you are now?
Mar 14, 10:34AM EDT0

I never planned to be an entrepreneur, but when I started my first company and understood the freedom and flexibility that came with it, I definitely realised it was the perfect life choice for me. When I came up with my idea for my Awards company I thought it was a career for life - but what I've since realised is that the entrepreneurship is the career for life, not that first company.  I didn't want to work in dating forever, and I also had more passion for entrepreneurship in general - and am passionately pro-equality and anything which levels the playing field for women. So starting A League of Her Own was a no-brainier - it allowed me to capitalise on the experience I'd gained, share it for others benefit, and continue my entrepreneur journey in a way I love. I know this won't be my last company but right now it has my whole heart! 

Mar 14, 12:55PM EDT0
How are the building blocks to creating sustainable income?
Mar 14, 10:09AM EDT0

You need to do the maths from the start, and be realistic.  Work out your business plan and monetisation model. Explore all the avenues for monetisation and be realistic with your estimations because your market will always be harder to sell to than you expect! 

Mar 14, 12:56PM EDT0

To celebrate this AMAFeed, we are running a special offer over at A League of Her Own- get £10 off the monthly membership (you can cancel any time).  

To reduce the subscription cost to £25 a month, enter the code SOCIAL25 at the checkout.    The code will only work 5 times, so act quick!

Join the League here.

Mar 13, 9:28PM EDT0
Any tips or suggestion for a female writer to start her own writing service agency?
Mar 13, 8:25PM EDT0

Join our League! We have trainings on everything from starting your company, branding, social media, doing your own PR ... :) www.leagueofher.com  (There are heaps of free resources on the website and if you want to do our study modules, click on Become A Member)

Aside from that - I'd say, get a really clear USP.  What kind of writing are you doing, who is your target customer, what are your packages.  Set out your plans in a business plan - and challenge yourself to answer all the awkward questions a bank manager or an investor might ask you.  

I think your website will be your primary investment.  Get a name and a logo you're happy with (if you need help with the logo, I recommend a company called Chelsea Creative) and make sure your website has good SEO and makes your proposition clear.

Then work out where your target audience are most likely to see you.  If you're B2B could you go direct to prospective clients? Base your marketing strategy on your target audience.

Quite hard to sum up starting a company in one paragraph, but hopefully that should give you some starting points

Charly xx

Mar 13, 9:26PM EDT0
From your experience, what are the basic steps somebody needs to take, to setup & develop a successful start-up development?
Mar 13, 2:54PM EDT0

It's hard to be too generic as obviously Start-ups come in all shapes and sizes, but I think the thing which applies to everyone is putting together a good business plan. Work out your monetisation model. Work out the questions, ifs and buts, so you can answer them if someone else queries them. Do your market research. Prove there is a customer-base and a demand. There is a great free template on the Prince's Trust website  which we swear by. And once you're up and running - tenacity, resilience and drive will keep you going. Running a business isn't easy but the challenge is part of the fun! 

Mar 13, 6:17PM EDT0
How difficult is it for a woman to start a company?
Mar 13, 12:20PM EDT0

Hi Maja! It is WAY easier than you think. The main issue we face compared to men is our own doubts and lack of confidence in ourselves, our ideas and or abilities! The best way to overcome that is by having a mentor, or peer mentors who can show you the way and reassure you that it's not as hard as you think! If you're thinking of starting a company or want some mentors, do check out A League of Her Own - we have a great community and learning materials specifically designed for women with business ideas.

Cheers, Charly 

Mar 13, 1:04PM EDT0
What difficulties did you face while making your dream a reality?
Mar 13, 10:13AM EDT0

I think it's probably the same problem most people face - getting others to believe in your dream. My first company was an industry awards company - so i needed to convince an entire industry that I had their best interests in mind and that I was building a legitimate business. Interestingly the way I did that was with my blog. My blog acted as an online CV or portfolio, showing my motivations and my thoughts on the industry and on account of that blog, I managed to get the support of the industry trade body.  Believe in yourself, hustle and don't stop hustling! It will all work out! 

Mar 13, 1:00PM EDT0

What motivates you? How has that changed?

Mar 9, 11:32AM EST0

Money! ;) haha nope honestly, turning an idea into a reality and genuinely seeing it affect people's lives is such a good feeling. Last year because of me, 150 people travelled to Amsterdam from all over the world to attend a conference. I literally changed the path of their lives for a few days, because of a random idea that I had in the middle of the night. What an incredible realisation! It's that buzz that motivates me - and to be honest when the passion and the buzz fade, that's when I know I need to move onto something new.  thanks for your question David! 

Mar 9, 7:00PM EST0
Do you think women feel intimidated in business and what are the reasons behind you answer?
Mar 8, 9:55PM EST0

Sadly yes, I don't think we have as much confidence in ourselves as men do - and I think that stems from the way we talk to young girls, the role models we provide them with, the toys we give them and the careers we encourage them to aspire to. There is a really sad statistic that women won't go for a job role they are only 95% qualified for, and yet men will apply for ones when they are as little as 35% qualified. We need to iron out these differences - and the different ways society views successful men and successful women - so that the playing field is more level. 

Mar 9, 8:08AM EST0
How and why did you become an entrepreneur and was it something you always intended for yourself?
Mar 8, 9:38PM EST0

Hi Sharon, so I fell into starting my own business. 

I was working in banking, and as a joke wrote a Facebook status saying I would go on 30 blind dates in the final 3 months of my 20s. My friends suggested I write a blog about it, and thanks to their enthusiasm and sharing on social media., 2000 people read the blog on the very first day. The blog went viral and The Guardian approached me to do some consultancy for me and work part-time as their dating editor. At that point I decided to make the leap and try going it alone, consulting. 

A few months later I then had an idea, based on emails people kept sending me, asking me to recommend a dating app or website. I came up with the idea of the 'Dating Awards' - industry awards for online and offline dating.  I now run them in the UK, and in the US and on mainland Europe.  It was through the Awards that I met my co-Founder Caroline, and we came up with the idea for 'A League of Her Own'.

So, in answer to your question - no, none of it was planned, but actually when I look back at my younger years, I have definitely always loved ideas and innovation and always been a bit of a 'hustler'! I think I've always had Entrepreneurial spirit!!

Mar 9, 8:14AM EST0

For International Women's Day we are running a special offer - get £10 off the monthly League of Her Own membership (you can cancel any time).  

To reduce the subscription cost to £25 a month, enter the code IWD2018 at the checkout - this code will only work for 48 hours. 

Join the League here.

Mar 8, 7:23PM EST0
What advice would you give to young women who want to succeed in the workplace?
Mar 8, 2:17PM EST0

My expertise is as an entrepreneur - so working for myself. But I would definitely recommend having a read of Lean in. Skill up - attend classes outside of work to broaden your expertise, take opportunities, and speak up. Be the best member of staff you can be, and when that is recognised, don't be afraid to ask for promotions and pay rises. Often young women get overlooked because they don't ask for the stuff young men do. Hope that helps! 

Mar 8, 7:21PM EST0

What tips do you have for growing your instagram following?

Mar 8, 12:07PM EST0

Hmm ... I have to admit I'm not great with Instagram.  I always say you need to devote yourself to the right form of social media, and in the past for me that's been Facebook and Twitter because I didn't want to spread myself too thinly.  With A League of Her Own, Instagram is a really useful medium for us, but my co-founder Caroline is definitely in charge! She definitely has the best eye for Insta out of the two of us! What I have learned from her ...

1) Know your hashtags and mix them up.   Have 3 or 4 lists that you mix up on different images.

2) Set a plan for your grid - maybe quote, product image, behind the scenes - and stick to it

3) Think about the colour scheme - maintain continuity and if you use filters use the same ones 

4) Engage with your audience - write a good length, interesting paragraph on each post.  It's not just about the image.  Ask questions, and reply to comments.

5) Follow relevant users who are interested in the same things you are.

6) Don't post too much - once a day is fine - but use the Story options to post regular content and truly engage with your audience 

Mar 8, 12:40PM EST0
Show all 3 replies
What were some of the methods you used for your company to gain credibility and which of these methods were the most effective and why?
Mar 8, 11:23AM EST0

Hi Boris, So my first business was industry awards for the online dating industry, and I actually gained credibility by writing my own dating blog - not that I realised I was doing that when I wrote the blog! It ended up as an online portfolio of my work, and my views on the topic - which the industry trade body then considered and trusted.  By then aligning with the the industry trade body, my company gained credibility. So I guess the overall lesson - blogs are great for some businesses for numerous reasons.  And partnerships and collaborations within your industry can really help you gain credibility.  PR can be a massive help to credibility - if you tell the right story in the right place.  And actually entering awards and being recognised by others can be great.

Mar 8, 12:33PM EST0
What have you learned about leadership, entrepreneurship and mentoring others through your journey?
Mar 8, 7:42AM EST0

That none of us believe in ourselves enough! Did you know only 5% of working women start their own business? And the reason for that is because they are scared of failure.   We all need thicker skins! We need to trust in ourselves, and take the steps we're scared of taking.  And if something doesn't work first time, work out what to change, and try again.

Mar 8, 12:28PM EST0

What has been your largest entrepreneurial mistake, how did you deal with this failure, and what did you learn from it?

Mar 8, 1:00AM EST0

Hi Anna, so this is probably the trickiest question someone has asked me!! Honestly, I've luckily had no major failures in my Entrepreneurial career. But one thing does stand out. I run an Awards company and I was desperate to take it to the States. Unfortunately I didn't appreciate how different some things are in the US and in UK. In the U.K. It's viable to run a one day event because everyone can get to London so quickly, cheaply and easily.  By contrast in the States some people will be travelling huge distances. Also, in England, if you hire a venue, all your furniture and staffing is included in the hire fee you're quoted initially. This wasn't the case in New York! I had to pay $2 for every extra chair, and $10 for every table! My budgets were thrown and the event attracted so many fewer people than I first expected. It wasn't a disaster, in fact the event itself was probably one of our best in terms of customer value and feedback, but it was an expensive learning curve and the profits were nowhere mar what I initially calculated! 

Nowadays I'm a lot more savvy to hidden costs! 

Mar 9, 8:18AM EST0
What are some of your non-work habits that help you with your work-life balance?
Mar 7, 9:43PM EST0

Ah I love this question Sarah! Last year I set myself 2 challenges - to read 100 books in a year (it was a book a week in 2016) and to do 300 days of exercise across the year (it was 250 the year before).  By setting those challenges, which mean I have to spend time relaxing with a book, or in the gym, I have reasons to step away from the laptop and spend quality 'me time' improving my body and brain.  I also have 2 dogs who make sure I leave the house and go for a couple of walks a day :) 

Mar 8, 12:24PM EST0
How do you conquer those moments of doubt that so often stifle so many entrepreneurs with great ideas and what pushes you through?
Mar 7, 8:52PM EST0

I think you have to believe in yourself.  But also - take the next steps with the idea.  Take the time to map out a business plan.  Think about the day-to-day realities of the idea.  How do you make money? How do you get started? Can you start with an MVP and test that first?  If you can write a full business plan from the idea, and explain the idea, and the business viability, that's how you turn an idea into a reality.  As for the doubts - well they affect everyone, all the time.  And to be honest, part of being an entrepreneur is the uncertainty and the adrenaline, and the buzz you get from turning something uncertain into something viable and successful.  So I guess learn to capitalise on that adrenaline, and try to devope as thick as possible a skin! ;) 

Mar 8, 12:22PM EST0
How were you funded or what creative strategies did you use to execute on minimal cash flow?
Mar 7, 7:50PM EST0

So all my companies have been self-funded.  My first company started on a shoestring - I needed £500 for the website and that was it.  The business model enabled me to pay myself back teh £500 within a month of trading.  I've never had a huge budget starting so I definitely recommend

1) asking friends for help - whether they volunteer some time, or you do a skills share.  You'll be surprised how many people can and will help you.

2) using freelancers for things.  At A League of Her Own we try to use female-led start-ups for any outsourcing we do.  That way we're supporting fellow entrepreneurs and our target clients.  But also - by using contractors you can be flexible and keep costs down.  Don't be put off outsourcing some stuff - particularly if you know your own time is better spent elsewhere or you don't have the skills for a job.

Mar 7, 8:26PM EST0
What is the best advice you received recently that you still follow, and why?
Mar 7, 7:27PM EST0

'Just do it' ... If you think of a quick task that you need to do, rather than write it down and put it off, just go ahead and do it now.  Applying that to my day-to-day life has massively changed my productivity and it makes you feel more on the ball and more efficient.

Mar 7, 8:23PM EST0
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