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Almost five years ago, I walked into Robbie Allen’s brand new office in a horrible mood.

Robbie and I had been meeting regularly at various Starbucks across the Triangle, and we had recently started discussing whether or not it was possible to automate content for websites for each of the NCAA Men’s Basketball programs, based on nothing more than StatSheet data. I loved these meetings. They were about automation, artificial intelligence, technology, writing, and sports – basically how I built my career mixed with how I spent my free time.

Robbie noticed my mood immediately. So I explained, with much animation, that I had just come from probably the worst meeting of my life –- a meeting that was supposed to have been about finalizing the funding of a project that I had been working on for close to a year.

Instead, what actually happened was an unbelievably bizarre rejection, and four months of free work, planning, and negotiation had just vaporized.

Needless to say, I was now in shock and without funding.  It wasn’t the first time. The technology product firm I had founded just a couple years prior was doing over $1 million in revenue, and it had taken a lot of “No” to get there. 

But this time I was furious, mostly at myself. A lot of trust went into that deal, and I got burned. Badly. In fact, I had turned down a lucrative consulting contract so I could work personally on this product, which was one I truly believed in. 

Robbie listened patiently to all my rage and then told me that he had been thinking more and more about automated content, and he thought we should get started.

My mood shifted instantly. “Give me the weekend to come up with a design,” I said.

By Monday, Robbie and I were underway, building what would become the StatSheet network. The codebase we created would eventually -- with a lot of help from a lot of talented people -- become WordSmith, Automated Insights’ NLG platform. 

Soon the automated content we were creating started gaining traction and getting attention.  Within a few weeks, Robbie asked me to come aboard full time, the first management hire. I thought about it long and hard – a million-plus business versus the chance to make automated content happen.

One is a nice gig if you can get it. The other changes the landscape. 

I pulled the trigger, with two caveats. 1) I would wind down my firm to dormancy so I could revive it again at some point. 2) I could keep working on the project that just got unfunded – because I believed in it that much.

Things happened quickly after that. I started hiring -- and every single hire is still with us today. As we began our Series A raise, it became apparent that applying our automated content platform to other industries was the way to go. Adam Smith and Scott Frederick, both of whom already had major roles in standing up StatSheet, came on full time. We changed the name, banked the round, and crushed the accelerator.

The rest is a blur. We landed Yahoo, and suddenly our content was reaching millions of people every week. Then came dozens of others, including the NFL and the Associated Press. We raised a strategic round just last summer, and moved into the most awesome office space overlooking the Durham Bulls ballpark. In 2014, our automated content, all of it going back to that first version of WordSmith, hit one billion articles. 

That should be enough.

But then there was that other project.

Which was ExitEvent.

ExitEvent went from an altruistic hobby to mission to full-fledged second startup in the space of a year, with just the three to five hours a week I could spend on it.

There was acquisition and funding interest in ExitEvent almost from the beginning, and by mid-2013, I knew that the path that we were about to embark upon at Automated Insights was going to eat up that extra three-to-five hours. I also knew that ExitEvent was starting to suffer from the limitations of my time. I knew it could be a lot bigger, and I knew, even though every instinct I had as an entrepreneur told me not to, that it was time to hand it off.

So I did. And less than 15 months after that acquisition, the first media source to announce the Automated Insights acquisition was the new, improved, bigger, better, smarter ExitEvent.

One thing that was unshakable during this crazy, frantic period was a commitment to doing things the right way. ExitEvent was my 9th startup and Automated Insights is my 10th, and they happen to be the two out of ten where the right decisions were made every time. Maybe they weren’t the best decisions, but they were the right decisions.

So when Laura asked me to write up a history of my time at Automated Insights and ExitEvent, those decisions were the first thing that came to mind.  I can’t go through all of them, but here are the common denominators that fueled those decisions. 

Don’t Follow the Playbook

This is the most important thing I can tell you. Don’t worry that your startup doesn’t look, act, talk, or feel like other startups.  Don’t build the next Facebook or SnapChat or Product Hunt or Automated Insights. And for the love of all that is holy, don’t mold your startup to work like other startups. No startup succeeded because it subscribed to the same management principles, developer methodologies, sales techniques, hiring practices, or funding schedules as the one that came before it.

Don’t Spend Money Unless You Absolutely Have To

You’d be shocked at how little money was actually spent at Automated Insights. We all took reduced salaries to be there, and the vast majority of us started out at a non-descript, cramped, smelly little hole-in-the-wall in RTP with secondhand furniture. But when we did spend, we spent wisely. Talent, proper benefits, R&D, and marketing, in that order. 

As for ExitEvent, that was all credit cards and favors called in.


Another common element between Automated Insights, ExitEvent, and every other startup I’ve created or been a part of  is that, at some point, I’ve coded. I’ll be the first to admit that I code with an undisciplined rage until things break, but those skills, for what they are, have been more than necessary. 

Learn to code, but don’t just learn to code. Code. Get in there and build. If you’ve got vision, you have to be able to express it in something other than English. If you’re not building a technical startup, learn and participate in the technical side of whatever it is you are building. No industry has gone without advancement. Make those advancements your secret weapon.

Don’t Raise Money Until You Can See a Massive Return

I don’t mean hockey sticks, TAMs, and ARR (you went back to the playbook again, didn’t you?). I’m talking about making sure you believe the home run ball has been lobbed right in front of you.

Too many times I see entrepreneurs seek out VC for startups that won’t get VC because VC isn’t right for them. Venture, or any other type of funding save for that which came out of my own pocket, was never right for ExitEvent. ExitEvent was, for me, a triple -- no more, no less. But in the end it wound up working out much better for me owning 100% of the company. And I believe American Underground can make it the home run it was meant to be.

At Automated Insights, we went out to raise only when we needed to get to that next home-run level. It was always time-consuming, mentally draining, and difficult. It’s never not. Keep that in mind.

Stop Worrying About Local VC

The state of local Venture Capital is not where an entrepreneur would like it. Nor is it where the local Venture Capital community would like it. Everyone wants more deals to happen here.

But while the numbers are disappointing, they’re not a death sentence. Never forget that Triangle startups should be building customer-first at all times.

Think About What You’re Building

We spend a lot of time talking about what Automated Insights should be, both externally and internally. Many management meetings are dedicated to product and company positioning. Internally, we dedicate time to the company mission, the culture, and the well-being of those people who sacrifice so much to work for us.

At ExitEvent, the mantra there was to be different and better than everything that came before it. That’s where “entrepreneur and investor only” Socials came from, that’s why I made money with ads instead of sponsors. That’s why I spent money on outreach instead of catering for the Socials.

There’s No Such Thing as Luck 

When the funding for the first iteration of ExitEvent fell through, I saw that as the worst bad break in my career. When it indirectly led to me joining Automated Insights, I thought that was one hell of a lucky move. I’ve had major highs and lows at both startups. And I could tell you that I was lucky enough to have both work out extremely well for me.

But after doing this ten times, what I can tell you is that there is no luck involved. There’s commitment, risk, sacrifice, wins, losses, recovery, and passion. That’s it. Things work out the way they were meant to. And as an entrepreneur, if that’s not good enough for you, you’re in the wrong field.