The bright side


Rosemarie Milsom

"I'm living such a big life now": Lisa Messenger.

"I'm living such a big life now": Lisa Messenger. Photo: Jennifer Soo

If ever a home symbolised a clean start then it is Lisa Messenger's rented North Bondi apartment. It is whiter than white. There are freshly cut white flowers in an array of vases, an utterly impractical white lounge covered with white cushions, white walls, scented candles and a white marble-top coffee table. It is a small yet surprisingly impersonal space, more like a boutique hotel room or high-end spa.

Messenger puts this down to her need for a "neutral sanctuary". "I don't want 'stuff' now," she says, curling her legs beneath her at one end of the lounge. She is wearing artfully ripped white jeans and is bare foot, though her toenails are painted fuchsia. "I'm living such a big life now and I have such a big vision for what I want The Collective to be [and] it's not about me or about money or about owning things."

Given her hectic work-load as chief executive and creative director of The Messenger Group and publisher and editor-in-chief of The Collective, a monthly glossy magazine that celebrates creativity and the entrepreneurial spirit, Messenger outsourced the interior design and her "team" oversaw her relocation last month.

Messenger and her cavoodle, Benny, may have only moved a short distance from the beachfront apartment she briefly shared with her former fiancé Jack Delosa, but she has covered vast emotional terrain since the abrupt and unexpected end of the relationship a year ago.


Rewind to April 2015 and Messenger had every reason to feel on top of the world. As the chief executive of a rapidly growing publishing company and creative agency and a best-selling self-published author whose positive, Oprah-esque affirmations have attracted a cult-like following on social media, she was making waves as a savvy entrepreneur, or in the current jargon, a "disruptor".

Early last year, Messenger had also just released her third book Life & Love: Creating the Dream, in which she described herself in the foreword as "unapologetically, deliriously happy". She was out and about promoting its message of self-love and authenticity, engaged to fellow entrepreneur Delosa, whose elaborate proposal happened over 24 hours at three locations. The couple had just moved into an expansive – and expensive – seaside apartment. At 44, Messenger was looking forward to marriage and motherhood.

But by the end of the month every mantra and affirmation she had ever promoted was suddenly drowned out by grief. First, she experienced a miscarriage. Then her relationship with Delosa suddenly ended and she did not hear from him for months, though she resisted the urge to check on him via social media.

"Life & Love had gone to No. 1 on Booktopia, which was amazing, and I had to go out there and talk about it when my heart was ripped into shreds," she recalls, hugging a cushion. "The two things I hold most sacred in my life are respect and loyalty and those things, in a hideous way, were destroyed. I'd dedicated the book to this guy." (She has since published a post-breakup version dedicated to her parents.)

The green-juice-loving health nut who happily boasts about getting eight to 10 hours' sleep a night found herself relying on sleeping tablets and cigarettes. She lost a sixth of her body weight. It took her devoted team and close friends to help her crawl out from beneath a thick blanket of despair.

She says she began to feel like herself again four months after the breakup. She did not speak publicly about it other than issuing, via social media, a brief and, given the circumstances, generous statement, which then triggered a flurry of positive feedback.

Messenger had not planned to write another book but a year later she has published Break-ups & Breakthroughs: Turn an Ending into a Beginning, her fourth and fastest-selling title. (She expects her books to generate more than $900,000 in sales this year.) This time, though, she decided not to participate in a round of promotional events.

So why write it at all?

"I didn't want to go back into that negative space but then I thought, 'If this is bigger than me then maybe I can own it.' I had discussions with my team and a few people said that if I was going to be authentic with my community, I couldn't just have Life & Love out there. Hopefully from now on my books will focus on more business-y stuff."

That might not be the case given the next chapter in Messenger's interesting life story, one which has so far included a failed starter marriage, depression, heavy drinking, a period of estrangement from her mother and sister (who were hiking overseas when she got married) and then a decade of intensive therapy and soul searching.

"You name it, I've done it," she laughs. "I do believe there's such a thing as too much self-analysis. By the time I launched The Collective, I thought, 'I'm so sick of myself.' I was like, 'Okay, I'm all good now. I know my self-esteem is intact. I'm strong.' "

During a holiday to Bali last December, Messenger had a profound experience on her 45th birthday. "That morning my friend said, 'Okay, I've organised your day' and I was really cranky. I didn't want to be pampered.

I thought, 'F... it, I want to do something worthwhile.' So I put a message on Facebook and asked for tips on how to give back.

"Someone mentioned the Jodie O'Shea Orphanage [in Denpasar] and I called and they told me what they needed and I went to the supermarket [to buy formula, nappies and cleaning products] and was there in two hours."

Not long after her arrival at the orphanage, Messenger spotted a five-month-old baby on a mattress on the floor. "I sat there with her for five hours," she says, tears welling.

"I really thought I could adopt her. I spoke a lot to Alison, who owns the orphanage, and she explained you've got to be a resident of Bali for three years. There's so much red tape. I felt I could make this happen, but I couldn't.

"So I thought, this is the year. I'm 45, this is it. I am going down the sperm donor path and seeking to have a baby. I'm really excited. I feel ready and I feel strong enough to do it on my own."

Those close to Messenger describe her as fearless. Her mother, who was a single parent for much of Messenger's childhood, describes her as a born disruptor. Messenger spent her primary school years on a 1800-hectare property outside Coolah, a small town in central west NSW, and was forever in trouble.

Boarding school in Sydney failed to tone down her rebellious streak. "Teachers would say, 'Just do it, stop questioning.' It was very rigid. I was always in trouble. I'm still asking questions, but as an entrepreneur that behaviour is celebrated."

Her friend Cathie Read says Messenger has an "incredible appetite for risk". "I think she truly believes in the value in what she is doing so she will find a way to do it."

When Messenger launched The Collective in 2013, it was an audacious move. She invested $1.5 million of her own money to secure the printing and distribution of the first four issues and she remains the sole owner of the magazine – and the other arms of her business. Although she was experienced with custom publishing and brokering sponsorship deals, she did not have any previous magazine experience.

"Lisa was Howard Hughes-crazy to launch a magazine," says friend Bradley Trevor Greive, the best-selling author and philanthropist. "I tried and failed myself 10 years earlier with a similar venture and I probably had far more pieces in place than Lisa when she dreamed up The Collective."

Now the magazine is distributed in 37 countries and her team has increased from three to 26. "There are so many pretenders in business who go to great lengths to talk up their virtual empires, their cutesy apps and greedy IPO plans," adds Greive. "Lisa has quietly built the real thing from the ground up with her own two hands using bricks and mortar, blood, sweat, tears – and chandeliers."

If Messenger needed any more proof of her growing influence, earlier last year, before the end of her relationship, she enjoyed an inspiring jaunt on Sir Richard Branson's idyllic Necker Island where she chewed the fat with the charismatic British billionaire.

She also broke her toe after trying to escape a snake that popped up unexpectedly while she was on the toilet with her shorts and undies around her ankles. She and Branson later laughed about the incident. "I'm always flipping things, searching for the positive in the negative. That's how I operate in life and business. I thought, that's one way to leave an impression!"

She commands up to $10,000 a speaking gig and is invited to address senior management at corporations such as McDonald's and has even presented a graduation address at her alma mater, Southern Cross University. The first of her books, Daring and Disruptive: Unleashing the Entrepreneur will be published in the US in September.

Messenger says she wakes up each day and asks one question: What is my purpose? After years of feeling unsatisfied and directionless, she now knows the answer.

"I want to be an entrepreneur for entrepreneurs and I want to show that anything is possible," she says.

"My life is so full on and so crazy, but I wouldn't change it for the world because it's [The Collective] so much bigger than me now."

On my way out, I notice some black writing on a mirror splashback in the open-plan kitchen: "Something wonderful is about to happen." It is pure Messenger and it's hard not to feel a warm flash of optimism.