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Putting the ‘suck’ in success, or how raising $5.5m over 12 rounds of funding in five years nearly killed me

Update: Inspired by the sheer volume of responses to her column, Jenene is hosting an event where this topic can be discussed more in depth. Join her at Flossie HQ at 29 Graham St, Auckland on Thursday July 19 to scope out ways in which to support founders and manage the ‘awkward teen years’ of capital raising and growth. The event details can be found here

I had been keeping my powder dry on writing this, including the title, for a book (oh, the juicy stories).

But today, having devoured and fervently nodded my way through Emily Best’s article, “How raising a $2m seed round really went”, it motivated me to overshare immediately.

In a similar vein, mine should probably read “How raising $5.5m, over 12 rounds of funding and five years nearly killed me”, but instead I’m just going to succinctly call it “Sucksess”.

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 clearly not being as capable as other founders. They say comparison is the thief of joy, and you better believe it. In her article, Emily speaks of Tech Crunch being worse that 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 the 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 (that things will work out, sticking with it will be worth it “in the end”). There are only so many body blows self-belief can take before it disappears.

“A to Z via every letter in the alphabet”, that’s what I’ve kept repeating for years as the formula for success. I would stand up tall, skyscraper heels, proudly on stage, looking all the Flossie I could, and beam out to hundreds of them at a time, “Try not to do too many letters twice!” 

I held up the sought-after Z like a pot of gold; Look! Here is the reward for the Persevering (and obviously slightly deranged). Not that I had got anywhere near Z myself, I’m still bouncing between D and F, occasionally going back to A and starting again (approximately every 12 months).

For a non-wallowy person, I reached a pretty new low point. God Scottie is going to kill me for telling this story. But, in reality I nearly beat him to it and for the love of god I just don’t want this to be how it is any more, FOR ANYONE.

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, VC’s, and the likes, launched into Australia, released a massive non-trivial chunk of new software across both sides of the business and grown net revenues by 90 percent. 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 the 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.

It’s painful to share this story, but like Emily, I feel compelled to and so reading it will probably change what you think of me. And 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. I have no one but myself to blame for my story, but our industry has a lot of things going on that we just treat as the norm.

#TBT a few months and you’ll find me lying on my bathroom floor. Lined up in front of me, all neatly arranged, perfectly formed 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 punctuated 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, but forcing myself to face this moment of pure emotional brutality was the obscene 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. And as the years of selfish behaviour were being added up in my head, the toll resulted in a new self-loathing that washed all over me, annihilating the resilience and forcing myself to consider this the new low?—?now also owning the status of Cowardice Shit. 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 blue print for success and you’re trusting your gut and 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 shoulds’ have a wicked way of breaking one’s self-belief.

From there, if you add together enough bad choices and ways to numb the pain, you’ll end up with additional regrets and sadness that then become all too real and loud. 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 and then, well, 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.

I’d fought for so much for so long and I was battle weary. My body was broken from disease, my mind lost to worry, my business felt in tatters?—?in spite of everything we had done and achieved, we weren’t getting there. I had tried, and I had failed to succeed. I was letting people down.

Weighing it all up in the brutal light of my bathroom reality, I was pretty sure that’s where I had gone wrong. I had consumed the cool aid which I had created and believed the hype I had conjured. Why? Because 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. When my vision struggled to get the funding, in spite of everything I had tried and done, the realisation hit that maybe I really had no idea what I was talking about, that the things I had been telling myself and others for years were entirely useless pieces of advice, let alone to be used as a formula for start-up success, well…well, I promptly fell apart of course.

As it transpired, I had no more insight into the how to make it work than the next person. Dumb luck, tenacity, the ability to sell and resilience had really been the only factors in getting me that far, and when they ran out I fell off my perch, crashing down to earth with my ego shattered all around me. It was a crushing blow. Every future remaining letter I hadn’t yet tried on for size was destroyed, alongside my confidence.

Success, the golden ticket to life, was going to allude me. I clearly didn’t deserve it and I wasn’t good enough.

Wait, hang on a minute. I’m calling bullshit.

It’s a big call, coming from a successful bullshitter such as myself. I’ve sold the snake-oil and profited from the economy of success for two decades. Try hard at school so you can be successful. Put in the extra effort. “Your positive action combined with positive thinking results in success”. Decide, commit, succeed. We’re sold success at every juncture. It’s a trillion-dollar industry.

But then I failed and when I did I thought it meant I had failed at life.

I felt like the joke that everyone else had known about all along. The dreaded self-doubt that most entrepreneurs carry around with them throughout their careers became like an unwinnable defamation case?—?because as it turns out I was an imposter and I didn’t have any sort of syndrome. Damn, guilty as charged.

And those feelings led me to this turning point in my life where I was seriously considering the end. No more sunrises, or sunsets. No more walks on the beach. No more making love at midnight. Or pina coladas for that matter. No more getting messy with friends, giggling conspiratorially, listening to music, playing cards with the kids, walking up big hills, lying nude on a private beach, riding a bike. All of my favourite things gone, and me along with it, because I had lost my way. I had pinned my identity on Being Successful, and had given it my all, only to find myself coming up short. I didn’t have enough chips to play and I was out of the game. What the hell was I supposed to do now?

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. Around that time 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 reinspect my priorities, get a grip on reality, find my way back to health and figure out how to live my life some other (more sustainable) way. Maybe success wasn’t all that it was cracked up to be, or maybe it’s 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 or sold it and 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 anyhow”. And actually, well, that’s pretty much exactly what I’m doing. Clearly, 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 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 laid the cards on the table and 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 like fuck 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 ongoing?—?and I’m doing what I can to consciously to tell the story differently than I ever have before.

Watch this space: Jenene 4.0.
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