Jenene Crossan on why she chose life

An entrepreneur comes back from the brink and takes control. Watch Jenene Crossan's Raw and Real interview with Todd Scott.

Just a few months ago, entrepreneur Jenene Crossan lay on the floor of her bathroom in crisis.

“My navigation was broken, and I didn’t know if I wanted to fix it anymore. I was tired of fixing it. The world just seemed to be, at that moment, a bad, sad, unhappy, unjust, disappointing place to be. I’d seen what was on the menu of life, and I didn’t want to order off it any longer,” she wrote in a no-holds-barred blog post last week, which soon went viral.

In a Raw and Real interview with NBR publisher Todd Scott, recorded just days after her post, she opens up about the events that lead to that point – plus her subsequent efforts to take control of her life, and for the first time, have a life, as she approaches 40.

Crossan grew up on Auckland’s North Shore, the youngest of seven children in a blended family.

Did being the youngest in a large family leave her feeling she had something to prove?

“I paid someone a lot of money to help me figure that out; you’re bang on the money,” she says.

“I’m very aware that the desire to want to prove yourself comes from being the youngest; the least, the one that no one probably had that much time for because they had quite a lot else on.”

Her father had his own business, which took most of his time.

She followed in his footsteps, but not via business school.

“I left school at 16 and have never sat an exam in my life,” she says.

I never went to university and made the friendships that go with that. I was already working fulltime. Then after that, going on an OE – I didn’t do that, I had my first business. I got married at 19 and bought my first house at 20 and started my first company at 20.”

Her first serious investor was the late Lloyd Morrison, the founder of Infratil.

Crossan had no idea who he was. Morrison had seen an article about the youthful NZ Girl online magazine founder, and emailed her to say he would like to put money in.

Morrison became the first of Crossan’s various high-profile mentors and backers; the group includes names like Greg Cross, Scott Gilmour and Rob Campbell.

The elusive cornerstone investor
And yet, it's always been hard yards.

Her latest venture,, lets people book a beauty treatment online. For consumers who don't want the hassle of a phone, it's easy. For service businesses tired of punters who cancel at the last minute or don't show up, it hands them a paid-up-front customer, who often returns.

Crossan feels she's hit all her marks over the past half decade with Flossie but 12 funding rounds have yielded a modest $5.5 million. 

"I tell people and they're like: ‘Jeez, you’re a sucker for punishment'," she says.

"It’s a hard landscape having a female-centric business in a sea of male investors; it’s a difficult place to raise money and New Zealand is not necessarily all that progressive in this space."

The master plan was to prove the business in New Zealand and Australia, then conquer London. The dream was – and still is – that a trade sale would follow to a multinational looking for the kind of e-commerce smarts and innovation that only come from a nimble startup.

But over the past 12 months, despite several pitching trips to London, capital has been hard to come by.

"We’ve hit all the milestones and we’ve still not gone further forward," Crossan says. "We haven’t got that elusive cornerstone investor."

She says a $5-10m injection would help to crack the fashion capital.

Instead, "It’s been fifty grand here and fifty grand there. And while that keeps you lean and hungry, it’s been hard to gain traction," she says.

"The runway was getting smaller and smaller and smaller and you get to the point where you only have weeks left of funding and that’s a really sickening time to be in.

"You’ve got people whose livelihoods are relying on you pulling the rabbit out of the hat – and that’s what it feels like at that stage because it’s luck; it’s dumb luck that you trip across something that allows you to save the day once more."

Slimming down
The dumb luck never eventuated, and Crossan decided to take things down a gear and concentrate on reaching profitability in New Zealand and Australia.

She wrote a new, leaner business plan in only five or six hours, concentrating on what was necessary to keep the business alive. 

It worked. "Investors who haven’t put in for ages started putting money on the table," she says.

But it came at a cost. 

"I had to turn around and restructure, and let go of people who were amazing; a lot of them were young and had never had that happen to them before so that was pretty devastating to go through," she says.

Imposter syndrome
Crossan says hundreds of people contacted her in the days after she published her blog post.

"The raw honesty from people I’ve never met telling me the deepest, darkest things that have happened to them," she says.

"I couldn’t get over how many people were in a really similar situation, or have been, or are going through.

"And I think the ones I could relate to the most were the ones who were founders, who could entirely understand the unrelenting pressure we put on ourselves that then is a pile on of all of the things."

"I think Ben Kepes nicely summed it up by saying ‘We expect our founders to be superhuman, to be superheroes, and then we put them on stages, and expect them to be gurus.’ You can see where the Imposter Syndrome comes from," she says.

She elaborated on this "fake it til you make it" point in her blog post, writing "I was coached by my first investor at the age of 22 to never let weakness show, “vulnerability is for pussies, people buy positivity,”

But suddenly, all that self-belief was gone.

Anxiety attack
Ironically, it was a relatively successful pitching trip across the Tasman that helped push her to the edge.

"It was quite a big pitch; I was pitching for our life, for a partnership and everything was on the table," she says.

"And it was probably hands-down one of the best presentations I feel I’ve ever done and you just sometimes you know you’ve nailed it; everything felt right. There is a whole variety of factors why these things might not turn out but I knew that I’d done everything I could. And I knew that at that moment, I was accessing all the bits that make me the person I am from a business point of view because that’s what I can do – and do that really, really well."

Two hours later, she was due to fly back home. That's when a panic attack hit.

"Do you think I could sit on that plane? No, I want to get off that plane. The wave of anxiety was unbelievable. And I’ve got a team member next to me who looks up to me, and I’m trying to hide this clawing feeling of ‘I want to vomit because I don’t want to be on this plane and I am going to hyperventilate in a minute," she says.

"It’s funny because I’ve never been in that place before. I’ve had lots of friends who have. Lots of people watching will have known the beautiful Mark Singleton, who died last year, who was the head of Cotton On. He was a good friend of mine. I thought it was a joke when I heard he’d died – to the point where I actually rang his wife because I genuinely didn’t believe it was true. She had to tell me. I still feel guilty about that. It was horrific. And the devastation that it caused; there were so many of us who just went, “I had no idea. He and I would do this for hours. We would talk about all sorts of stuff – usually, over a bottle of Belverdere and I loved that about him and I really struggle to reconcile that he is not here any longer, and that I can’t make that right.

"And I undoubtedly had that at the back of my head. I wasn’t drunk when I was lying on the floor. I was devastated and broken – and broken from worry and anxiety."

Back from the brink
The Sydney trip actually had a reasonably positive outcome (more on that next week).

But as Crossan lay on the floor of her bathroom, the outcome was still in doubt.

She couldn't see a way through her business problems or her crisis of self-belief. "I can’t see how to unravel this because I had built this and my reputation would be entirely in tatters if this falls over," she said to herself.

What allowed Crossan to literally pull herself up off the floor?

She thought, "I can’t ever do what Mark did; I can’t ever do what I’ve seen other people do. I can’t do this to my children, I can’t do this to my family, I can’t do this to myself. I can’t be this ungrateful for all these opportunities that I’ve had. I’ve got to get myself out of this corner and feel I’m not painted in any longer."

“And that’s when I started writing," she says.

“Not only to share but to figure out how to make my way through that."

It was hard, especially when she watched her 16-year-old stepdaughter read the post.

"There was a look of heartbreak. Her face just crumpled," she says.

But ultimately, "It was cathartic. I feel like I’ve shed a skin."

And through her writing, she's also developed a new outlook.

"I feel like 20 years of doing things a certain way has gone out the window. I don’t want to be the poster child for ‘stress causes cancer’, I don’t’ want to look back and say, ‘How did I not have my eyes open to what I was doing to myself, and what I was allowing to happen as well," she says.

Jenene 2.0
The past few months have seen Crossan scale down her business ambitions to a manageable level, and also take a new approach to her relationship with Scottie Chapman, her husband of eight years who also has a demanding business.

"Every three months we’d have a week together, somewhere, without phones or computers," she says.

They have already had their first getaway, at a one-bedroom B&B in Byron Bay.

She's partly going public so that people battling with anxiety know they are not alone, and to help promote discussion. But it's also to hold herself publicly to account. She's told the world she's going to have a decent work/life balance, so now she's got to follow through.

Flossie investors have been supportive.

"I’m very fortunate to have the phenomenal Rob Campbell as a shareholder – and he’s almost always the first person to say, ‘you’re doing great. I’m really proud of you'. So he was one of the first. And there was a steady trickle of others. They all knew I’d had a fairly tough time and I’d been candid about operations and me trying to get my head around the business so it didn’t require so much of me," Crossan says.

Her father sacrificed his home life for business. Crossan doesn't want to do the same – or at least, not any more.

Her attempts to have a child with Chapman have been a struggle for the past couple of years. Several rounds of IVF have been complicated by three operations for endometriosis. The time is approaching when she will have to decide whether to keep trying, or whether to get "everything yanked out."

She hasn't decided what to do yet. But she feels that now she can calmly think about it.

"For the first time ever I’m creating some space around myself so I can make decisions for the right reasons," she says.

"I don’t want to get to 60 and say, ‘I should have tried harder;  I let my business guide my decision [on having kids]."

Now, she's revisiting the decision, and this time the demands of her company do not factor in.

If you or anyone you know requires support for mental health issues at any time free phone or text 1737

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