Jenene Crossan on why she decided not to end her life

Jenene Crossan: "I didn't want to be broken any more"

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Just a few months ago, entrepreneur Jenene Crossan lay on the floor of her bathroom, contemplating suicide. Everything was laid out that she needed to end her life.

“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, Flossie.com, 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


29 · Got a question about this story? Leave it in Comments & Questions below.


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29 Comments & Questions

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As a small business founder and owner (still) I can relate to everything written above. It can get pretty lonely out there in small business land at times. Twice we came back from the brink - the ANZ small business average is 2.5 times over 30 years. I was lucky to have a wife and partner (the same person) who didn't leave me. There were a couple of times I wouldn't have blamed her if she had. In the end it came down to the simple fact that we were too far in to turn back (we still owe ourselves half a mill) and in our case bit too long in the tooth to do anything new - that being 50. In the end (this being 60) we have managed to survive both as a business and a family, which considering what we've been through is a sheer blessing.
The good news is that there is good news if you want to stick with. Every year you do it you get a bit better with each passing cycle.
Now we have someone else who really wants to keep it alive for another 20 years and we're right behind her. Yes, it's family, with all the good and bad stuff that that brings, but I've run my course and set it up, she can now double it over the next 20 years with her skill set, slightly different to mine, but that's exactly what's going to do it.
Small businesses are the backbone of business in this country. They don't all have to grow into big businesses to be successful. They just have to be good businesses, and with the work-life balance bit in order, everyone can live happily ever after.

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Thanks Graeme for sharing your story.

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In ten years of television (back in the day) I don’t believe that I was ever involved in anything as raw and real as this. Thank you for sharing Jenene! I truly believe that you will have literally saved the life of a few that will watch this. 

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Apologies that it has taken me this long to respond to the wonderfully positive comments here. It was a pretty raw weekend - rather out there headlines will do that and obviously cause some distress in the family. But the conversations that have ensued have been incredibly positive and for that I feel grateful for the chance to share. Even if the shedding skin feels like walking around naked all day, not highly recommended, but as I keep saying, I do feel like a weight has been lifted off me.

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A very good piece, this; big ups to Jenene for the interview, especially this weekend on Anthony Bourdain's suicide.

For most of us not born into money, our economic lives can be hard, and even harder finding a balance between that and living a satisfying life; and entrepreneurs by their nature tend to higher peaks but bigger troughs (I reckon - noting I'm not an entrepreneur). You never can know another's life.

Recommend a read of Jenene original blog post in full; great that NBR provided the link.

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Topical yes, but not planned and actually that's the reality of every day in the world 2,200 people opt-out. There's a huge difference between mental fatigue / fitness and mental illness and this is one of the things that if we explore more, we may be able to find a pathway through this.

Thanks for your comment, it's appreciated and felt.

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Life has its ups and downs, but at the end of the day you only have one, and it's not that long. I'm a great believer in embracing everyday as a good one no matter how bad things get, because when it's over it's over forever.

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One of the reasons I like NBR, it's not purely focused on the economics of business, and looks at the human effects and causation for economic behavior.

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Amazing article, all the best to you Jenene.

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Thanks Andrew, I hope you're well.

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An alternate view is that 5 years and 12 rounds of funding for $5.5m raised would suggest this business is struggling to scale and losing momentum. At 5 years, you should either know if you have a winner or not. As MCB of Atlassian said " if you aren't growing very quickly, it's not much of a start up" ... Knowing when to throw in the towel and roll your learnings/ funding contacts into something else is also a key part of the entrepreneurial journey. NB: there is a massive difference between "small business" and "start-up business" : the models are like apples and oranges. If your start up business has not hit high growth ( ie 100 % - 1000% pa) within 18 months, you are already on borrowed time. There is a vc term for this- " the walking dead".

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I’m told that they grew just under 1000% in 16 months once they started scaling.They have grown net margin 90% in the last 6 months. The hard part is having to turn scaling off due to not having marketing funds. But the new strategy has them profitable in NZ, but with lower revenues and slower growth path (essentially 80% of their sales come from habitual customer base, vs when they were investing in growth that was more like 50%).

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Ah that's a tough break. Those are pretty good numbers. NZ really is a tough place to get a startup through the valley of death and offshore ( so little vc capital, almost non existent cap markets for smaller companies etc). Keep on Keepin on ...

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I think there are some real challenges building a business from NZ - one is capital and of course just lack of scale. So doing multiple rounds is a necessity. Made massively harder because in this case the founder is a female.

If this had been started in San Francisco with a male founder who knows where they might be.

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This is not a space that men can necessarily even see.

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Thanks Todd for stepping in and responding on this. Those are all accurate reflections of the business. However, I would suggest that if the outtake on reading my piece is simply about the business, then I would suggest rereading it as the point possibly has been missed. Lance, you're bang on the money too.

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Great thought provoking story by Jenne - well done! It has also brought about another stories on being an entrepreneur. For many, I would be seen as a successful entrepreneur - I started a company from nothing, renting fax machines, pivoted to rent water coolers, grew the business, did an IPO, and still own 70% of the business.

Yet, I have always said that if I knew what I knew now, I never would have started my own business.

There I was following a corporate career, high salary, traveling upfront and flashy car, to go to no salary, back of the plane and bomb car. Then with new baby, we lived for 7 years like paupers, on the edge of our loan facility, house and all assets on the line, so close to going under. And one bank did ask for their loan to be repaid; fortunately another bank took us on. Stress, stress, stress, when had I been in a Corporate career I could have walked away at any time - not as an entrepreneur!

Then finally success, to be destroyed by one rogue manager and my incompetency, you run up an $18 million debt, so 10years of hard work, no dividend, to get back to evens again.

Now I live in my dream home, nice car, a great wife and daughter, and I have no regrets. I was one of the lucky ones, and I know what Jenene has gone through, but just didn’t get the luck on the way through!

My thoughts are with you Jenene, and congrats in exposing the life of an entrepreneur - thank goodness you saw there is more to life than being an entrepreneur!!

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Tony, thank you. Your comment meant the world to me. I know of your fantastic ability to share via the EO network and my husband Scottie has been fortunate enough to get to see this up close. I really appreciate this - thanks.

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I have heard a lot of positive stuff about Jenene over the years and the energy she has to pursue her goals (and the success she has already achieved). Good on her for confronting such a sensitive topic and being refreshingly honest about the harsh realities of building a business from scratch.

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Thanks Terry. I don't doubt I've been the centre of a few conversations this last week, especially if I take it off the sheer volume of "are you okay?" conversations I've had both on and offline. But I can assure you it's not something that anyone would ever do for the attention, it's more vomit-inducing than most would imagine. But I keep saying it, it's been incredibly cathartic. My energy had been so depleted and now it's being rebuilt through genuine, honest conversations and support from extraordinary people. I am feeling a lot of gratitude (alongside the rawness!)

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A start up Tech company well known in NZ was a high flyer but got pummeled by sentiment on a spiraling sell down even though the company produced good results.
Alot of intelligent investors and high flying Directors had no control over a never ending sell down.
Harsh lessons were learned about Investor sentiment and NZ IPO's dried up and no other company wanted to dive in amongst the sharks.

NZ now has an IPO Crisis !

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Wow what a great article & comment by Tony F. Also very impressed with Jenene's honest and realistic approach to work and life. If I had the money I would certainly invest in her business any time.
I am in a similar predicament (I am the CEO Founder) but it is my wife (not in business) that is in the dark place, which puts me in a hard place. Hearing such stories makes it more normal and gives me hope, Thank You.

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I've met with a lot of people this last week and heard many, many stories from literally hundreds of people from all over the world. It's incredibly common and no, you're not alone. I really feel for the supporters, I know it's been hard on my husband this last week. And the more you're able to talk with people comfortably, the better. I hope for more dialogue as a way for us to find a way to help all New Zealander's get help when they need it, not when it's too late or incredibly dark. I'm doing some research into the "what" at the moment - it's a new learning curve for me too. Thanks for your comment.

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The model is broken. All of this ridiculous "let's be like SIlicon Valley" BS creates an utterly unrealistic expectation on founders, unrealistic expectation in terms of expected investor returns and unrealistic expectation on the part of boards of their CEO and exec teams.

And yet... again and again we hear the "let's emulate SV" line. Unfortunately, companies like Xero, and founders like Rod Drury make it look too easy, especially with unhelpful lines like "it all went entirely as planned" or "once you have the formula, it's easy." It's not easy, there is no formula and it almost never goes to plan.

So instead of trying to be like SIlicon Valley (gratuitous plug, but more on that little red herring here - https://t.co/787Z7JT1g7 - how about we learn to build businesses in a sustainable way - sustainable from a capital perspective and, most importantly, from a human one.

Jenene is a rock star, and I have incredible respect for her bravery in telling this story, but she shouldn't have had to tell it, she never (and other founders also shouldn't be) put in a position where even 1000% growth doesn't tick sufficient boxes for the board, investors and other stakeholders. It creates a never-ending spiral - the investor make demands of the board, the board makes demands of the CEO, the CEO makes demands of the management and so on....

Without getting into an argument about NZTE and Callaghan Innovation's priorities, it seems that, from a human perspective at least (I won't even go into the average returns from those who peddle the "hockeystick growth at all costs" line) we'd be better off looking at the entire startup and small business world through a different lens....

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I agree, and we need more stories bravely told like this to expose how irresponsible the Venture Capital industry is. The figures on average returns are from the investors point of view. The founder’s odds are much worse with the extreme downside protection measures.
Some of the NZ ‘Angel’ community are also guilty with the terms I’ve seen.
Even the Universities are teaching our young people that starting a business = seed round to get you to Series A.

We don’t require Venture Capital to grow $100m businesses. Of course there is a place for it, but NZTE and Callaghan and the ‘ecosystem’ seem fixated on helping companies jump on the fund raising train, which you can’t just hop off.

There is enough anxiety and stress in growing a business sustainably.
Our Venture Capitalists should be required to fund a support system for the founders that they statistically set up to sacrifice by design.

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Thanks Ben. Your comment is bang on the money. Wouldn't it be nice if the start-up heroes, such as Trade Me, Xero, My Food Bag, Pushpay told their real stories. I've heard a few of them myself, and they're not mine to tell, but I certainly know that every single one of them has had some vomit inducing moments. Sharing those would start to reset expectations.

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Jenene I interviewed you maybe 17-18 years ago about NZ Girl, and much water under the bridge since then, for both of us. I am in Australia having recently delivered a national tour presenting on Mental Health in the Workplace. There are 3000 suicides a year over here and one of the biggest barriers is opening up the space for people to be having brave conversations. And that's on both sides; the main emphasis of the program is to support business leaders to be having the brave conversations...opening them up to conversation intelligence ….and allowing vulnerability. We sometimes hold a vision of people we admire ( read my own admiration for your journey ) and can be surprised when some truths are revealed. I remember being shocked to hear of Robin Williams passing … it hit me deeply and called me to step even more fully into my own work. Your willingness to do "Open Kimono" here is a wonderful thing.....you remind people of our shared humanity and awaken others to what sits behind the mask so many wear! I use a video that shows stunningly what anxiety and panic attacks look and feel like and without exception participants in my programs have said" I had no idea" . I honour your courage!

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Lovely to hear from you Pat, I remember that! Open Kimono, I'll remember that. I like to think I've always tried to own the vulnerability, but I'm holding myself accountable for a greater reality dose of the journey. The stories being shared back to me are both harrowing and encouraging. I'd love to see that video, I can imagine what my own face must be like.

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I've written a follow up piece from last week -around mental fatigue vs. illness. Please have a read and help us with the discussion https://medium.com/@jenenecrossan/burnout-vs-mental-illness-1f9b6a97b2cb

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