Entrepreneurial Lessons: Charly and Caroline, Founders of League of Her Own

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So, you decided to have your own business but don’t have a clue about how to start? Charly Lester and Caroline Brealey went through all the rough paths of being an entrepreneur when then started out. That’s why they created A League of Her Own, a membership community to help women set and develop their projects with affordable training, support, networking and collaboration opportunities that make all the difference! In this interview, Charly talks about the challenges of uncovering new territories, the importance of seeking role models and, above all, of believing in yourself.

Project M:  What motivated you to create A League of Her Own?
Charly Lester:
Caroline and I both started our first businesses 7 years ago, and we can still remember the feelings we had at the time.  We each started them alone, and we didn’t know any other women who ran businesses.  It was so daunting, and I can certainly remember questioning whether I was doing the right thing, and whether I could do it – because I was a woman.  And I hate that I had that fear and doubt, but it’s true and it’s because the only people I knew who ran their own businesses were men.

We both faced so many challenges and had so many questions in the early days, and didn’t know where to go for answers – and so years later, when we were sharing our experiences with each other and realised we had that isolation and those doubts in common, we decided to tackle the issue and design something for other women so that future female founders wouldn’t have to face the problems we had.

The League is designed to answer all the questions we both had when we were starting up, to provide women with hundreds of role models – to show that businesses, and the women who found them, come in all shapes and sizes, and to create a support network so women can ask questions and advice, meet peer mentors and share their wins.

Project M:  What are the biggest challenges you have faced so far?
Charly Lester: So far I don’t think we’ve had any major challenges with the League, other than having to create all the hours of content for the website (which literally took us a year before we launched!) however my biggest ever business challenge was with my US Dating Awards.  Running an event in another country can be really tough – you have to fly out multiple times to prepare stuff, and then fly your team out and sort accommodation etc.  And then when I got out there, I realised stuff is SO much more expensive in New York than London! I hosted my Awards at a ballroom in New York and I was charged $2 for every chair in the room, $10 for every table, and $300 for every couch! For a one day event (and on top of thousands of dollars of rental fees)! Crazy! I learned a lesson from it though, and will always check out those things in future and not take anything for granted!

Project MWhat advice would you give to those thinking about creating a business?
Charly Lester: To have confidence in yourself.  You will always have doubts and fears, but you need to believe in yourself, and surround yourself with people who also believe in you.  We all have down days, but every problem can be solved.  Sometimes you just need to take a step back and re-think it.  Be your own biggest cheerleader, and never undervalue yourself!

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