This year closed a multi-million dollar partnership agreement, raised just under $1 million, launched into Australia, released a massive chunk of new software and grew net revenues by 90%. So how did they nearly run out of cash twice and why did founder Jenene Crossan hit a personal break point? She shares the answer to that question with brutal honesty.
The trough of sorrow taught me lessons I never knew I needed to learn.

I was coached by my first investor at the age of 22 to never let weakness show, “vulnerability is for pussies; people buy positivity”. And every day for the last 18 years I’ve believed that to be true. I’ve berated myself for not being tough enough, not having what it takes and for not being as capable as other founders. They say comparison is the thief of joy, and you better believe that is true.

In her article about Seed & Spark, Emily Best speaks of TechCrunch (a website that reports on business related to tech) being worse than Instagram for your self-esteem, and damn she’s right. Because on top of already feeling pretty left out, it has a way of making you feel bad for not being happy for everyone else and that envy shakes your values. When you’re a resilient person, and everyone recognises you as such, there are times when said resilience packs its bags and fucks off, and you realise it’s only really built on self-belief. There are only so many body blows self-belief can take before it disappears.


So, let’s go back a few months.

Let’s start with the positive. This year we’ve closed a multi-million dollar partnership agreement, raised just under $1m, been to the other side of the world pitching in front of global corporates, VCs, and the likes, a massive non-trivial chunk of new software across both sides of launched into Australia, released the business and grown net revenues by 90%. Not bad.

On the flip side, interjected ironically and often inconveniently in the middle of each of the above most critical junctures, the business nearly ran out of cash (twice); I hit the personal broke point (from years of being a ludicrously underpaid founder and every cent I have being in the business); restructured my team; had three operations; nearly destroyed my relationship; heard the word “no” about 300 times; and was told that stress was a major factor in a disease wreaking havoc on my fertility and quality of life. And lastly, speaking entirely candidly, I hit rock bottom.

The thing about hitting rock bottom is you never really know if it is actually, you know, the bottom.

“Pushing boundaries creates isolation and lack of perspective. When you’re making it up as you go along there’s no blueprint for success”


It’s painful to share this story and reading it may change what you think of me. I’ll live with that if it means that next time you’re either listening to a founder’s pitch or you’re working with someone who is in this space, it stops you from being an asshole.

Rewind to a few months and you’ll find me lying on my bathroom floor. Lined up in front of me, all neatly arranged and waiting to be washed down with Belvedere were 25 individual sleeping pills. I had no plan. I’d not thought it through. There had been no preparation, ritual or note. No final farewell.

I’d not dressed in my nicest clothes to be found how I wished to be remembered. In fact, the 'depressed chic' look I was sporting accentuated my bereft state. The fall from Most Inspirational Person 2016 to the cold hard wood next to my toilet knocked all of the polish off.

For hours I just stared at the little white ovals daring myself to make a decision; 'shit or get off the pot'. Opt out and all of this mess and pain will go away or flush them and face up to the long brutal rebuild ahead. Truth be told, I knew what I wasn’t going to do it, but forcing myself to face this moment of pure emotional brutality was the punishment I’d set myself.

I appreciate that this may come across as the most self-pitying, flagellating and selfish situation that I had deliberately put myself in. As the years of selfish behaviour were being added up in my head, the toll resulted in a new self-loathing that washed over me, annihilating the resilience and forcing myself to consider this the new low. What a horrific thing to consider doing to my partner, my step-kids, my parents, my friends. The pain of a friend’s death a year previous surged back, and even without an audience I remember flushing a bright red, utterly embarrassed that I’d let it get so bad. I saw the impact his death had - I lived the pain, I witnessed it.

How could it really be that bad?

Pushing boundaries creates isolation and lack of perspective. When you’re 'making it up as you go along there’s no blueprint for success and you’re trusting your gut instincts. You hear "no” all-day every-day. You put everything you have into it, on the smell of an oily rag, and then when you make all the milestones you said you’d make, do all the things you said you’d do, create technology and customer tools that are world-class (and recognised as such) and still have someone say, “but it’s not really tech, is it, love?”.

Said once and it would be almost amusing, but dozens and dozens and hundreds and hundreds of rejections, bad one liners, pats on the head and “you should haves” have a wicked way of breaking one’s self-belief. Pepper in some particularly poor health (what came first - stress or disease?), IVF, a shocking lack of finances, the brutal weight of responsibility and pressure — on that spiral downwards death seems like an almost obvious way to turn the noises off and to escape the corner you’ve managed to paint yourself into.

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, in 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. This was the path I had been sold on as to the one that would lead me to success. A notion I had told myself was entirely true, then sold others on.

The story isn’t over yet, but I’m pretty sure the journey I briefly took to the depths of my personal darkness will help me get to a happier, more content place.


As the hours rolled by, I began to see that I’d really put the suck into success. I could see the high cost I was paying for the life choices I had made. And then my husband found me. I don’t know whether he just didn’t notice the unusual line up or chose to not say anything, but either way he simply pulled me up and held me — for hours. How could I want to miss a moment with this good-hearted man?

Perhaps it was time to inspect my priorities, get a grip on reality, find my way back to health and figure out how to live my life another (more sustainable) way. Maybe success wasn’t all that it was cracked up to be, or maybe its definition is not what I thought it to be. Maybe I needed to figure out how to not let it suck — it couldn’t have this much of me anymore. I appreciate that when you’ve not succeeded the way you planned, to then state, “the cost of success sucks” sounds a bit like the kid who didn’t get picked yelling petulantly, “I didn’t want to play that stupid game anyway”. And, well, that’s pretty much exactly what I’m doing. I’m human and I’m acutely aware of my first-world, entitled problems. I’ve paid a lot of money in therapy to appreciate that doesn’t mean they’re not mine.

But like any good story, the moral turns out to be that it was the best thing to ever happen to me. The 'Trough of Sorrow' taught me lessons I never knew I needed to learn. I pulled myself up, I got honest with myself and others. I swallowed my pride and took on changes that hurt, but helped me — and us — out of the hole. I took the shareholders on the journey, and transparently shared that changes needed to happen. And they supported it, overwhelmingly. And so the rebuild began and I started to create space for me, Jenene Crossan, as a person, not just as a founder.

The story isn’t over yet, but I’m pretty sure as a result of the journey I briefly took to the depths of my personal darkness will help me get to a happier, more content place and space. And it will smell and look a lot like success — but perhaps this version won’t suck the joy out of life and myself in the process.

Or, at least, I hope that’s what will happen, and I’m holding myself accountable for doing so. I turn 40 in July and it’s a marker of movement for me, from the way I used to run this outfit, to the way I will from now on — and I’m doing what I can to consciously to tell the story differently than I ever have before.