Leela Cosgrove on bridging the gap between the haves and the have-nots

Leela Cosgrove is not your average entrepreneur. Pulling herself up from housing commission roots, she’s built an impressive entrepreneurial and philanthropic empire that has earned her friends like Richard Branson and led to her launching the Australian chapter of the Dell Women’s Entrepreneur Network (DWEN). She joined editors Cec Busby and Adam Bub on the First Act podcast to share her incredible journey.

Leela Cosgrove is one of Australia’s most sought-after coaches, mentors and speakers and a keen advocate for women in business. As founder and CEO of training and education company Strategic Anarchy, media company The 8 Percent, and sales tech company Iron Cage, she also owns Australia’s largest witchcraft supply store, High Priestess.

Breaking the poverty cycle

Growing up in a housing commission estate in the Brisbane suburb of Zillmere, Leela had the odds stacked against her. Yet, she says her innate sense of hustle was evident at a young age.

“Zillmere was an intense area; a lot of drugs and violence, and a real rhetoric that anybody who grew up there was doomed to repeat that poverty cycle,” says Leela.

“But in my very formative years, the two strongest female role models in my life ran a business – my mother and grandmother had run a second-hand bookstore. So, I knew from a very young age that business was something that I wanted to do,” Leela recalls. “I was always selling something, making something, doing something.”

After high school, Leela started working temp roles in corporate land, but soon discovered that admin jobs weren’t for her. Signing up to a freelancer website gained Leela the opportunity to begin writing content for major business strategy consultant, Jay Abraham.

“I was getting paid $9 an hour and everybody around me said, ‘You’re crazy, you’re getting ripped off’,” Leela reveals.

With her innate sense of bold independence, Leela looked at it differently.

“I’m writing these articles for Jay Abraham, whose content is worth tens of thousands of dollars; I’m getting sent to his seminars. The education I received for that tiny amount was worth so much more than the pay. It was hard work, but the four years I spent working with him was such a crucible. I learned of the foundations of business and made a lot of connections and a network that were crucial to me being able to grow my own business.

“I worked hard for it because when you grow up in a household where there’s no food in the fridge, or the phone might be turned off, then you just don’t have the luxury of that middle-class guilt around money. So, I just wanted to make ALL of the money!” Leela laughs.

Turning expertise into a business

The lessons gained from writing about business gave Leela a wealth of knowledge that she felt determined to share.

“When I was freelance writing, people would ask me ‘How do you put together a unique value proposition?’, so I started teaching that. And then they’d ask, ‘But how do I use that with my marketing?’. I let the market guide me – what did the people in our community need next?

“Something I say to people a lot if they’re starting out in their early business is to start with service. People want to jump into being a consultant when they have corporate experience – which is fine – but doesn’t really translate to small business.

“Starting with service gives you a foundation of deeply understanding what you’re doing, but it also helps you organically understand over time what the pieces of the puzzle are that people really need. That’s always been how we’ve created our products and how we’ve moved and evolved our business.

“Richard Branson said to me, ‘We never go in looking to make the best product; we never go in looking to make a lot of money. We go in to look at where a market is not being served’.

“That’s very much the organic approach we’ve taken over the years,” Leela says.

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Bridging the gap between the haves and the have-nots

Leela’s passion for using her business success to support and boost other entrepreneurial women eventually led to her invitation to Richard Branson’s Necker Island. Leela says the experience further opened her eyes to opportunities to bridge the gap for women and underprivileged communities. 

“The big takeaway was that I have an interesting set of life experiences that not everybody has,” Leela reveals. “I’m on Necker Island with people who are generationally wealthy … and I’m Leela from Zillmere. The very idea of needing a job is just not within their realm of experience, and that gives me an interesting ability and a responsibility to walk between two worlds; to be able to navigate both and translate between the two. I really took that seriously after this experience and took that into my philanthropic work going forward.

“What I know from growing up in housing commission is that the cycle of poverty isn’t just financial, it’s a cycle of trauma. You don’t end up hooked on drugs and living in housing commission for no reason. There’s always some history of trauma, and that gives me an insight that not a lot of people have. So, I’m able to translate between those worlds and change the way that people think, and bring some humanity to the philanthropic works I do – making sure that the stuff that we are doing is practical and helpful in hitting the real problems.”

Bringing DWEN Women’s Leadership Conferences to Australia

Leela is now using her influence and network to bring together other entrepreneurial women in the Australian chapter of the Dell Women’s Entrepreneur Network (DWEN). Becoming the Australian DWEN chapter leader is another example of Leela’s forethought and tenacity.

“In 2019, I went to the DWEN conference in Singapore and was blown away by the quality of people in the room; women who are doing the most phenomenal things from all over the world. These women were so far ahead of me and my tiny $2 million-a-year business. Being able to be in rooms with women who’ve done that stuff and to sit down and have conversations with them is a rare opportunity.

“After that event, I reached out to DWEN and asked if I could start a Melbourne chapter because it was so valuable to me. DWEN came back to me and said, there’s no chapter here, have all of Australia. So, I took on the Australian chapter leader role.

“This ability to bring together magnificent people and connect them to one another makes me so happy. DWEN is a perfect way to be able to accomplish that.”

Leela Cosgrove speaking at an International Women’s Day event.

“I want to focus specifically on the challenges that women are facing from a leadership position,” says Leela. “I kept going to these events where the conversations would be about how women ‘just need to have more confidence’, or ‘women need to learn how to draw boundaries’ – turning the issues back onto women’s way of thinking about things.

“I don’t think the issues that women have in society are because they lack confidence or they can’t set boundaries,” Leela insists. “It’s one thing to set boundaries, it’s another thing if nobody wants to pay any attention to them. I know so many incredible, confident women, but they don’t get the same kind of airplay that guys get. The idea that that’s just a lack of personal confidence is quite crazy to me.

“So, I want to do something different. I want to have real conversations, curated by women and had by women. I want to bring the audience into the conversation too, because I know that there’s always a wealth of conversation and wisdom within the audience, not just on stage.

“That’s how the Women’s Leadership Conference was born. Over two days, on the 25th and 26th of October in Melbourne, we’ll be having these conversations to look at how we can work together to create movement on climate change and on the micro-aggressions that women are facing in the workplace. How do we work together to support one another?

“To me, women’s genius is in community; that’s where women shine. Where women excel is in creating communities and supporting one another in that way.”

Leela shared so much inspiring information in this episode of First Act. Listen to the full ep now to learn how she built her business empire, gained invitation to Richard Branson’s inner circle, and became one of Australia’s most respected female entrepreneurs.

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