Leela Cosgrove knew from a very young age that she would one day have her own business. She grew up watching her mum and grandmother run their own secondhand bookshop and realised that she would one day be a successful business owner.
“From a very formative age, where you’re really starting to make sense of the world, I understood that this is what they do, women run businesses, so there was no question that is what I would do also,” she says.
Cosgrove’s first business was Strategic Anarchy, a boutique B2B consulting firm, which helps businesses manage and train sales teams, using a tailored software and management system, and has generated more than $20 million in revenue over the last decade.
It was borne out of a self-driven ‘apprenticeship’ with an events company that brought motivational speakers, like Tony Robbins to Australia, she says, and gave her an insight into what a successful business looked like.
“I started Strategic Anarchy in 2009, but before that, I was very lucky because I had a mentor who took me under his wing. I had a day job as well, but at night I would freelance for him for very little money — but that three-year-apprenticeship was foundational to give me the skillset and the experience, and the contacts and the networks to start my own business,” she says.
It kicked off an impressive career that has seen her named in the top 50 fast growth companies in Australia and top 8 of Female Founded Companies in the Asia Pacific Region. She has also been named as one of Australia’s top 25 female entrepreneurs and has collaborated with large corporations such as Hermes and Virgin Australia.
Cosgrove is also the Australian Chapter Leader for the Dell Women’s Entrepreneur Network and sits on their Global Advisory Council.
Recognising the importance of mentorship in entrepreneurial success, DWEN has established a mentorship program that pairs experienced entrepreneurs and Dell’s subject matter experts with emerging leaders. This initiative provides invaluable guidance, advice, and support to help mentees navigate challenges and capitalise on opportunities.
“I’ve been incredibly impressed with how Dell don’t just talk about empowering female entrepreneurs, they are actually doing it and through DWEN are providing a networking platform for women,” she says.
“It is such a broad range — from people who are in pure start-ups who haven’t made money yet, to people who are making a couple of million dollars, to those whose businesses are turning over a hundred million dollars.
“There is also a mentorship program that people can apply to be matched with a more experienced and successful business woman, which is just so valuable,” she says.
Alongside Strategic Anarchy, Cosgrove runs Australia’s largest witchcraft education and events company, High Priestess. She has spent the last 30 years working as a professional psychic and healer, providing guidance to Hollywood celebrities, billionaires, and rock stars.
Her unconventional CV has opened doors to exclusive business gatherings, including on Necker Island, owned by British entrepreneur Sir Richard Branson. Cosgrove describes these events as exceptional opportunities to network with accomplished professionals.
She underscores the value of face-to-face interactions, encouraging female entrepreneurs to leverage every chance to connect in person, as these moments often lead to significant opportunities.
“DWEN provides some very valuable face-to-face networking opportunities that can help you connect with people that you can share business experiences with. I think being able to connect with people in person really changes how you communicate,” she says.
“I met some amazing people on Necker Island, including a former executive from Credit Suisse who turned to me and she said, ‘yours is the most interesting bio I’ve ever read in my life’. I thought, wow, you are Credit Suisse — I must be good at this!
“That just wouldn’t have happened if I hadn’t been there and taken the opportunities in front of me to meet people and connect,” she says.
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For more than a decade, the Dell Women’s Entrepreneur Network (DWEN) has brought women entrepreneurs together from around the world to help them connect with each other, scale their businesses, and ultimately succeed. The DWEN community welcomes all levels of entrepreneurs, from start-ups to scale-ups. Joining DWEN will give you access to women entrepreneurs from around the world and valuable resources to grow your business – including the latest technology, access to funding resources, and best practices from a global network of members.
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