Lisa Messenger will always remember the day she decided to change her life. It was 8 November 2004, when, faced with a future that was “spiralling out of control”, she seriously contemplated suicide. “My life was an absolute train smash,” she says. “I drank way too much. I partied hard. I alienated my whole family.” But that rock-bottom moment proved to be the wake-up call she needed. Lisa gave up drinking the next day. “I made a conscious choice to pick myself up out of the gutter,” she says. Over the next several years, Lisa says she focused on her personal growth and development, using her savings to take self-help classes all over the world and eventually, in 2009, writing a book about what she learned called “Happiness Is”. Armed with renewed ambition, energy and purpose, Lisa began to turn her fledgling marketing agency into an empire. Lisa is the founder of Sydney-based Messenger Group, with its publishing and marketing divisions. Today, the Messenger brand encompasses 18 different offshoots, and she has set up a multimedia business, Collective Hub. “I haven’t been trained in any of this,” Lisa says. “But everything I’ve done in my whole life has kind of led to this point.” Lisa, who was born in a small town in New South Wales, was never sure of her career path. After school, she worked as a horse-riding instructor in Shropshire, England, where she says she learned to work confidently with other people. After moving back to Sydney, she worked in event management for various brands, including Cirque Du Soleil and The Wiggles. In 2001 she founded Messenger Marketing, an ambitious venture she admits to “bumbling” her way through. “I had no idea what I was doing. I was having a lot of fun,” she says. “I think this is the thing when people start out. You’ve got this hunger and this passion so you kind of do everything for nothing.” For the first few years, Lisa had a meagre turnover of about 50,000 Australian dollars ($38,600; £29,700) a year. She struggled financially but loved the work, though she was still waiting for her big break. “I kind of always had this deep knowing that I was destined for something bigger,” she says. The turning point came in 2013, when Lisa says she walked into the office and told her three employees that she wanted to start a magazine. She wanted to interview the interesting people she had met through the years and compile conversations with them into a lifestyle publication for entrepreneurs. The result was a monthly magazine, Collective Hub, which currently has a circulation of 50,000 across 37 countries, but is growing, according to the company’s sales figures. Sir Richard Branson, Anne Hathaway, Maria Sharapova and Debbie Harry, of rock group Blondie, are just some of the stars who have graced the cover. Lisa, who is the publication’s editor-in-chief, was not put off by the declining market and the thousands of other print magazines already on stands in Australia. “Naivety can be kind of a good thing,” Lisa says. She decided to make what could have been a stoic, masculine business magazine look like the kind of publication that was selling. “The flip there was, let’s make a business magazine look like a fashion and design magazine, so it was kind of messing with people’s chi,” Lisa says. “What happened was when we went into news agencies we were sitting – and still are – next to Marie Claire and Vogue and Harper’s Bazaar and Vanity Fair.” Lisa also says she had to do more than ask for the A$5,000 or A$10,000 that magazines might normally receive from advertisers. She went and asked for A$50,000 or A$100,000 at once, offering speaking engagements and sponsorship opportunities in return. “I thought much bigger,” she says, “which kind of goes against everything.” Lisa’s company has now grown to 25 full-time staff and 80 freelancers around the world. She says her “daring” approach to business and entrepreneurship hasn’t changed over the last decade. “I am purposefully counterintuitive,” she says. “Every single industry that we go into or idea that we come up with I continuously flip it completely on its head.” It’s a message she promotes in the range of books she has published through her company, including Daring and Disruptive: Unleashing the Entrepreneur, and Money and Mindfulness: Living in Abundance. Megan Dalla-Camina, strategist and author of the book Lead Like a Woman, says Lisa has a reputation in the Australian business community for being fearless. “She does what she wants,” Dalla-Camina says. “She doesn’t actually believe, I don’t think, that there are any barriers. She’s very bold in how she operates. Lisa’s latest venture is a collaboration between Collective Hub and Torrens University, which will offer a graduate certificate in collective entrepreneurship. She says she hopes to immerse students in the world of entrepreneurs. “Not everyone’s cut out for the entrepreneurial path. So I wanted to kind of hold their hand and support them through that,” she says. As for the future, Lisa says she likes to stay in the present and test opportunities as they arise. It’s all part of her signature fearlessness. “Most people will write a 300-page business plan and they’ll tick every box and cross everything off,” she says. “I’m much more about the ‘fail fast’ mentality. Go to market, test, iterate, morph, pivot, change. That way we are just continuously testing, testing, testing.” Any other way would be boring. “Business should be fun,” she adds. “It should be heaps and heaps of fun. Off the charts.”