Rollin' Like Sisyphus

There’s No ‘I’ In Success, But There Is Failure

Posted in The Fail Pail by Huckleberry on May 6, 2014

More honest than investing in software development.

More honest than investing in software development.

I’m about to share one of those stories that you just sift around in your head for a while, trying to find some way to circumscribe the earnest stupidity, but I’m frankly not Magellan enough for this voyage. Rather than dive into a preamble that attempts to explain or guide you in this, I’m just going to jump into the meat of it:

On the surface, it seemed like I had the best life. A popular blog with millions of readers. The perfect relationship with Brian, the most adoring fiance in the universe. A great set of supportive friends and a nice social standing in Austin, TX. And, last but not least, an awesome company, making marketing software, with a great team, that was making money and (finally!) shipping products.

In Writing 1A, they teach you not to be so patently obvious in your foreshadowing.
It’s okay.
I can pretend that I have no idea what’s about to happen.

Yet something lurked just beneath the surface. It would come out at awkward times, like 3AM, when I would wake up and feel an edge, a discomfort. Something felt broken. But when I looked at my life, I couldn’t spot it. What was going on?


Then, one day, a few weeks ago, an event happened (I’ll save the details of that for some other time.) Suddenly a torrent of emotions poured in. I was overwhelmed. I stayed home from work one day–my best friend Erica sent me some poetry, and I just cried. I wept. It felt like my soul was pouring out of me, one tear at a time. I reeled from the onslaught of emotions for days, and soon thereafter, I broke off my relationship with Brian. Whatever wasn’t right in my life wasn’t easy to find. It went deep into myself. Brian was shocked, and as well he should be. I loved Brian. I still love him. But something wasn’t there. It wasn’t right. It was why we weren’t getting married. He was the perfect guy on the surface, but for some reason he wasn’t perfect for me.

Don’t worry, Venture Capitalists, your investment dollars are perfectly safe. Just some personal issues to work through.

Today is my fourth day in Boulder, and I have not stopped crying. Yesterday, our largest customer, representing 22% of our revenue for Whoosh Traffic, cancelled. Because of their cancellation, we could no longer make payroll next week.

Oh, fuck it.
Well, at least her company gave 110% and left nothing on the field.

The truth was, I didn’t really want to build a huge SEO software company.


If MarketVibe was what I really wanted to do, why wasn’t I launching it on my blog? Why wasn’t I doing whatever it took to get paying customers and make it successful?


The brokenness pervaded my dreams, leaving me exhausted when I woke up in the morning. I developed a sugar addiction and a video game addiction. I gained so much weight that many of my clothes stopped fitting. It’s hard to explain the contrast between the abject depression that ate at me in the middle of the night when I was alone and vulnerable, and the “everything is OK” smile I’d put on as my “public face.” It was why I stopped blogging.

Fuck that.
Where’s the Goddamn investment money?

Today I write this, still in Boulder, still reeling emotionally from the large volume of changes in my life in the past week. I write this humbly, with a complete lack of ego.

No, seriously, where the fuck is the money?

My business failed and it took my savings, and $640,000 of investor capital on top of that, with it. I let my blog income sources dry up while I focused on the business, and now I must figure out what’s next, from an awkward place I haven’t been in in many years: no money, no salary, and some credit card debt on top of that. Sometimes you have to rip everything apart to find the core of yourself, the beauty inside you. And this is where I am today.

So you ripped “everything” apart because an event that you won’t detail forced you to reckon with the fact that your life was either completely empty or that you’re simply a bipolar wreck of a human being.
Would have been awesome if you could have told the VCs before they invested in whatever the Hell this marketing company was supposed to be.

My business failed, but I am not a failure.

You’re half right.
But never fear, she’s learned something, so grab a pen and paper.

The people who embrace that vulnerable core of themselves are our true next generation of leaders, and today I get to stand up and say: That’s me. That’s not just who I want to be–it’s who I am now. I had to break my entire world to find it in myself, but now I stand before you, humbled, having failed in a way but having found something even better from that breakdown.

That’s it?
Well, just what in the Hell are you going to do now?

I want to keep our team together. Paul, Amanda, and I work together well.

No you don’t; the company failed and you fled town for a week at a crucial time. Who in the cold blue fuck is going to go through THAT again?

So we may form a new company, or rearrange the current one.

Quick straw poll – both Andy and Amanda say Negatory on that one.

I think I may do some consulting for a month or two, recovering my finances and helping other authentic leaders of larger companies find their voices and build better teams. (Email me at erica at erica dot biz if you’re interested in talking about this further–it won’t be cheap, but it will be worth it for you.)

Yes, that’s just what my business needs, vague declarations of “finding yourself” when the company’s circling the toilet due to failed leadership and an admitted apathy toward doing, well, anything really.
But don’t worry, Erica has already provided us with the perfect tagline for her business cards:

I’m sorry I lost your money.


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )


Connecting to %s

%d bloggers like this: