December 27, 2014

The Next Fork in the Road

I had several friends and advisors review this post prior to publishing it; most encouraged me to go forward with publishing it but others cautioned that future investors / business partners may choose to pass on a deal with me due to the content below. I took time to consider their warnings. I’ve decided that any businessperson who would deny me business simply because I express what it’s like to be a vulnerable, actual human being going through a sustained period of immense stress is someone I don’t want to do business with in the first place. That being said…

It was just over a month ago that we made the decision to shut down MarkedUp, and in the time since I’ve been on the road visiting with family and friends I neglected during my three years of 100+ hour work weeks working on MarkedUp.

While I’m proud of everything I accomplished at MarkedUp, I’m compelled to write about part of the experiences I had creating it before I can move onto what I’m going to do next.

This blog is the fruit of my labor on my very first startup from the summer of 2010, Social Media Measurements – we never shipped a product and I didn’t work on it for very long. But I learned a lot, and was rewarded for sharing that knowledge openly on this blog by way of landing a sweet job with Microsoft. That job at Microsoft ultimately led to starting MarkedUp.

When I look at what I’ve written in the past 2-3 years, the “MarkedUp Era” – I’m struck not by what I’ve written but by what I haven’t. I’ve acquired vast sums of knowledge in the time I spent on MarkedUp – and at great cost. My savings. Relationships. Twenty five pounds. Three years of hundred hour work weeks. Never taking more than three days off in a row during that span. Sleepless nights. Brutally hard decisions. But despite the expense to obtain this knowledge, I’ve documented little of it.

It’d be easy cast this glaring omission aside with the wave of a hand and the perfunctory “I was just too busy” excuse I dropped tens of thousands of times over the past three years, but that wouldn’t be true.

If you find yourself in a position of leadership, your job first and foremost is to set a vision and direction for your organization and sell everyone else on it. This becomes an agonizingly difficult task the first time your market thesis is rejected by customers, and you have to pick up the pieces and alter your vision.

So you have to wear a mask over your doubts and concerns. You have to keep them hidden, like state secrets that can destroy you. Send the pain below. Keep a stiff upper lip. No crying in the newsroom. And so on.

You even have to wear masks around your inner circle – one for my girlfriend. One for my family. One for my friends. One for friends I don’t know as well. The only people you can be truly open with are the ones who don’t have an agenda for you, and they’re few and far between.

So I put on a mask for this blog too – saying nothing that could add risk or complicate my ability to get a deal done. Hence why I’ve said little of substance beyond some technical knowledge and mild self-reflection. I’ve had pitch meetings where investors showed up with print-outs of previous posts – they’re fair game for researching deals, so I treated them as such.

Eventually, when we were in the midst of executing our pivot – I stopped wanting to talk to people about my startup altogether. I can relate to Travis Kalanick’s story about his saga with Red Swoosh.

Anyone who knows me in-person knows that I have a hard time keeping my mouth shut – for the first 14 months of working on MarkedUp, I wouldn’t shut the fuck up about it. For the past 12 months, I talked about it less and less until I eventually stopped talking about it – I just wanted to quietly get on with my work and successfully execute our pivot.

I became withdrawn and increasingly isolated, still working hundred hour weeks all the way. Pushing and pushing and pushing myself, knowing that we were running out of time. Eventually fatigue found me and I started having trouble getting out of bed, finally forced to catch up on the sleep I cheated for the previous two years.

After we had shipped MarkedUp In-app Marketing and executed our pivot – we were on the verge of nailing it. But the deal we needed to execute in order to keep going fell apart at the last minute, as is all too common.

So with the final nail struck in MarkedUp’s coffin, I felt immensely disappointed and exhausted in every dimension (physically, intellectually, emotionally, and financially.) I wasn’t disappointed in myself or the efforts of our team, but mostly in the outcome. I made the decision to publicize our shutdown because I considered that to be the right thing to do for our customers and the honorable thing for me to do personally.

I’ve received an overwhelming amount of support from friends, investors, MarkedUp users, and others since. I sincerely thank you all for it.

Starting in 2015, I’ll be embarking on a new adventure that I look forward to sharing once able.

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I'm the CTO and founder of Petabridge, where I'm making distributed programming for .NET developers easy by working on Akka.NET, Phobos, and more..