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The First Company I (Never) Sold


The email was sitting in my spam folder, wedged in between very urgent messages from Nigerian princes and very flaccid promises to cure erectile dysfunction. I generally don't make it a habit to check my spam folder, and my position on that wasn't much different back in 2012. But, I had a six-month-old baby, and sleep deprivation plus endless nights means you have to find new ways of entertaining yourself while praying your child would just go back to sleep. It was on this sleepless night that I chose spam as my entertainment.

"Huh, there's a lot of shit in here," I thought to myself, ready to flick the app closed on my phone. Right as my thumb hovered over the screen, I noticed an email that didn't seem as spammy as the rest. The subject line suggested at least an understanding of who I was and, interestingly, what I was doing as a side project outside of my day job.

Saw your writing on The 5.5 Hole

I should provide some context before you think I, too, was one of those email spammers sending junk about some mysterious thing called "The 5.5 Hole."

In baseball, every position has a number. Pitcher is 1, catcher is 2, first base is 3, and so on. On the left side of the infield, the third baseman and the shortstop make up positions 5 and 6. Tony Gwynn, one of the greatest baseball players of all time and the San Diego Padres was a left-handed hitter who could put a ball in play to any part of the field. When he had the opportunity or if he was ever–and this was incredibly rare–behind in the count, he would spray a hit the opposite way between third base (5) and shortstop (6). He called that area, the 5.5 hole.

In 2011, I decided to start a blog. I had been a late adopter to blogging's rise, but I had always been a writer. I knew I was going to write about one of two things: baseball or politics.

Lucky for me, I knew baseball better.

I started my blog, The 5.5 Hole, in late 2011 and wrote about the Padres only initially. I would later expand it to write about baseball in general. I used Blogger and never expected anyone besides maybe my father to read it. Here's what the site looked like in late 2011:

This brings us back to the email in my spam folder. Blaine Blontz was an editor for a site under the FanSided umbrella called Call To The Pen. He had somehow seen my writing on The 5.5 Hole, liked it, and wanted me to come write for FanSided. I would be paid…


But FanSided and Call To The Pen had large audiences. My writing would be seen by far more people. I would ultimately say yes so that I could chase something more important than money. I would be getting paid in exposure.

It's cliche now and induces full-on cringes from people when the idea is mentioned, but in 2011, writing for exposure was not an uncommon or even terribly looked down upon endeavor. With a day job working as an insurance claims manager, writing was all the pay I needed. For a while, at least.

Blaine and I would both write for a number of publications under the FanSided umbrella, but Blaine soon got an offer worth more than eyeballs. He was offered a paid editor gig at SB Nation.

SB Nation had a history much like my own sports blog but on a much grander scale. It was started by Tyler Bleszinski as a single blog called Athletics Nation, focused exclusively on the Oakland Athletics. It grew into a massive network of sports blogs and then expanded further into technology. SB Nation exists today and is still popular, and the company behind it grew to become the well-known media platform we today call Vox Media.

So, Blaine went to write for money. How much money? I didn't know, but I knew it seemed pretty rad to write for money. After a couple of months there, he reached out to see if I wanted to join as well. Together, we would write about baseball across multiple SB Nation sites, and we would even get paid for that writing. Well, for some of it.

Not all content on SB Nation qualified for payment. Certain blogs with longer-form content would yield payment, but many of the quick news stories did not. For the paid writing, we were paid $5 per article. It was barely enough to buy some shitty Taco Bell meal, and at the end of the day, I was once again writing for exposure.

The exposure was a real thing. My writing ended up in Sports Illustrated (online), I was interviewed on ESPN Radio multiple times, and I became a relatively known baseball person on Twitter. But something started bothering me. I suspected that the ad revenue SB Nation, FanSided, and Bleacher Report (another massive sports blog network) brought in was large. Was it large enough to pay writers more? I wasn't sure, but I wanted to find out.

Around this same time, I had an idea for a niche sports topic. Injuries were rarely covered, and when they were, the articles hardly touched on the consequences of the injury or went into any sort of deep impact analysis. I had the itch to start a new sports blog focused on this topic, and I had the itch to prove that an ad-supported blog could pay its writers more than $5.

I suppose this is the ego of an entrepreneur. To assume you can do something better than a large, well-capitalized incumbent cuts to the core of capitalism's optimistic insanity. It was with that ego and touch of insanity that I reached out to Blaine and pitched the idea. Would he want to come and build MLB Injury News with me?

Blaine was immediately intrigued by the idea. He saw the opportunity in covering a niche topic. He and I had both seen the rise and ultimate success of a site called MLB Trade Rumors. That site started as a small personal blog that grew into a fully self-sustaining business. All by covering a single topic with a single sport. So, we went to work.

Building a sports blog is not the hard part. The hard part comes later. To create our fledging "startup", we started with a logo (of course). Brand is everything and the right logo would set us on a path to success immediately. A logo to us was the equivalent of a Product Hunt launch to many new projects today. It was all you needed.

Or so we thought.

We paid a few hundred bucks for a custom logo, which still remains one of my favorite logos, and we got to work writing. Blaine and I had both learned that the key to traffic was volume and SEO. Prior to writing online for FanSided and SB Nation, SEO might as well have been a new Kia model to me. But I got my crash course in the high stakes game (read: unpaid game) of sports blogging.

Here's how our site operated and how we found content to write about:

We created lists of baseball writers (mostly the real beat reporters but also some independent bloggers) on Twitter. And then we spent all day on Twitter. If there was a report about a player's injury, we wrote about it. Immediately. This meant I was often sneaking away to the bathroom during work hours at my day job so that I could sit on a toilet in the privacy of the bathroom stall and hammer out an article on Apple Notes. I would then log into the web interface of Blogger from my phone, paste the story in, and hit send.

Of course, this only happened if we caught news during the day. The brunt of the writing Blaine and I did was early in the morning and late at night. Together, we could pump out somewhere in the range of 8-14 articles per day between the two of us. We had volume, but we didn't have distribution.

Fortunately, during our time writing for the larger sports blogs, we learned about a Fox Sports-owned site called Yardbarker. Yardbarker was the Digg of the sports world and provided a platform for independent bloggers to find distribution.

The company provided a platform for bloggers and sports fans to gain additional exposure for their sites by joining the Yardbarker Network which provided targeted advertising and increased promotion.

- Wikipedia

The last part of that description would prove game-changing for us. It took a lot of work to get accepted into the Yardbarker network. I can't remember the exact requirements, but they had a relatively high bar. For example, I remember sites had to have existed and been producing content for X number of months leading up to their inclusion in the network. We worked our asses off to clear the bar, and when we were added to the network, everything changed.

The interesting thing about Yardbarker wasn't that it syndicated content you wrote to their platform. Instead, it linked to your content from their front page. This meant that you owned every view that Yardbarker funneled your way. And you could monetize those views as long as you were willing to give Yardbarker their substantial cut of the ad revenue.

Which we did happily.

Yardbarker took MLB Injury News from a site that was read by maybe 1,000 people per month to a site that was read by 100,000 people per month. It took us from a site that generated $0 in revenue to a site that was generating thousands of dollars in revenue, even after Yardbarker took its cut.

In his book, Zero To One, the entrepreneur and investor Peter Thiel had this to say about distribution:

It’s better to think of distribution as something essential to the design of your product. If you’ve invented something new but you haven’t invented an effective way to sell it, you have a bad business—no matter how good the product.

Before Yardbarker, we had a bad business. After Yardbarker, we had a good business, but what exactly were we selling? We were selling attention, of course.

But we weren't alone in the Yardbarker network. We had distribution thanks to the network, but we had a massive amount of competition. In April of 2011, about a year before we joined the network, Yardbarker had more than 900 blogs participating.

We had distribution, but attention was finite. It was and remains a zero-sum game. MLB Injury News had to find a way to make sure the eyeballs funneled from Yardbarker's network landed on our pages more often than other blogs.

With strong distribution, products can shine. We polished ours daily. AI was more than a decade away from becoming mainstream, so we wrote everything ourselves. Fortunately, Blaine and I are both talented writers, and we put that talent into the content, creating a significantly better product than most of what existed in the sports blogosphere. But it wasn't just the quality of the product that allowed us to shine, it was also the double-niche nature of the product.

We niched down to covering baseball, but we took it a step further and covered injuries in Major League Baseball. No one else was doing that. This meant, we were the only game in town. And when you're the only game in town with a high-quality product, you are often awarded the holy grail for distribution.

A place on the front page.

Much like Digg was the "homepage of the internet", Yardbarker was the homepage of the sports internet. ESPN was there, but fans craved the more nuanced and passionate takes from sports bloggers. To make it to the frontpage of Yardbarker meant you would see a sudden daily spike in traffic to your own site. And that's exactly what set us on our path to success.

By working tirelessly–and I mean this literally as I was getting up at 4am every day to write before work–to land on the front page of Yardbarker, we increased our traffic and our ad revenue significantly. Something else started to happen as well. People started to learn who we were.

We had a Twitter account that we had used for initial distribution before Yardbarker, but it didn't have much of a following. Now, though, we had close to 20,000 followers on Twitter. We had people who would bypass Digg and come check MLB Injury News daily while drinking their cup of coffee. We had an audience and distribution and revenue.

But we were burning out.

Blaine and I had vowed never to bring writers on and not pay them. We had been so turned off by this practice at the large, well-capitalized sports blogs that we refused to do it. Now, we had enough revenue coming in to build a revenue split model with writers we would onboard.

The split was simple. At least it seemed like it would be simple at the time. We would track page views, and whatever percentage of the overall page views we got that were generated from an individual writer's posts would reprecent the percentage of the ad revenue we would pay out to them. However, we had to cover operational costs, so the pool of money available to pay was 50% of the monthly ad revenue. Let's say we took in $3000 in a month. 50% of that is $1500. Now, let's say you were a contract writer whose posts had generated 40% of our page views. You would get $600.

We were excited to launch this payment strategy, and the writers we ultimately brought on were excited to participate. What we didn't anticipate, though, was the monumental task of tracking page views in a world where analytics were still janky at best and wrong at worst. The writers would dispute the page views often, and this would lead to Blaine and I spending the time we thought we'd save from not having to write as much figuring out payment distribution calculations.

Despite the headaches, the site continued to grow, and we decided to expand. Rather than covering just baseball, we would cover injuries across sports. The network approach had worked so well for SB Nation, FanSided, and Bleacher Report. It would surely work for us. But we needed a different name.

The umbrella site we ultimately created was called Sports Inury Alert, and it covered injuries in the NFL, NBA, MLB, and NHL. We split some of the existing writing staff off into their favorite sports and brought additional staff on. Each sport was its own blog under the umbrella, so we had to retrace the steps we had taken with MLB Injury News. Because we knew what we were doing by this time, each site ratcheted up views and revenue much quicker–by the scale of the sport's audience of course. NHL did the worst in terms of views and revenue. NBA did OK. NFL and MLB were the clear breadwinners.

NFL and MLB? In the United States, the two most popular sports are NFL and NBA. So why was baseball outperforming basketball. It wasn't just that we had started with MLB, though we considered this a factor for a while. No, there was something more that Blaine and I had initially missed in our naive focus on just writing.

Our audience wasn't just made up of sports hungry fans. Well, it was. But it was also made up largely of fantasy sports players. Many of these players spent decent chunks of their salarly playing fantasy sports. In America, the two most popular fantasy sports are–you guessed it–NFL and MLB.

Now that we knew our audience (it's embarrassing that we had made it as far as we had without even exploring our reader base), we knew we could expand further. Fantasy sports weren't a niche thing like they were in the 70s, 80s, and 90s. Fantasy sports was big business. Today, it represents a nearly $26 billion market. We simply needed to lean into this market.

I began reaching out to fantasy sports websites to orchestrate partnership deals. This was late 2013, early 2014. Fantasy sports sites at the time were focused on strategy and would cover some bits of breaking news. But back then, they hardly ever covered injury news. Yet, injuries derailed a fantasy sports team as much as it did the real team. Understanding injuries in real-time and whether you would need to grab a reserve player or could ride out an injury could mean the difference between winning the week and losing your shirt.

One of the partnerships I managed to land was with a site called Fantasy Pros. They weren't as large as the ESPNs and Yahoos of the world, but they were larger than us. They had a paying audience, too. Much like we had done with Yardbarker, I worked out a deal with them to syndicate links to our stories on their site. This brought us targeted eyeballs, desperate for news about the players on their fantasy roster.

It was a match made in heaven. But that old demon I had staved off when Blaine and I brought on writers tracked me down once again. I was burning out.

It didn't help that I hated my day job, was living in a city I hated, and my wife and I were expecting our second son. As I negotiated and continued to build a relationship with the owner of Fantasy Pros, my family was trying to figure out what was next. As desert dwellers all our lives, my wife and I couldn't handle another year in Washington, DC. We couldn't afford it, hated the winter cold, and hated the summer humidity. We needed to escape.

A few months later, we left DC and moved to Dallas. With a new job and new baby on the way, the pressure of writing as much as I had been and the pressure of managing a team of writers boiled over. I spoke with Blaine–he knew about the partnership and the relationship we'd built with Fantasy Pros–and told him I didn't think I could keep going. He understood and we worked out a deal where I would sell my half of the company to him.

It wasn't a lot of money, but I was out. The crushing weight of raising a newborn and a toddler, figuring out a new city, learning a new job, all while trying to write 8-10 articles per day and manage a company had left me wobbly. Selling my half of the company stabilized me, but it also left a hole.

A few months later, as I started another new job at a startup in Dallas, Blaine told me that Fantasy Pros had acquired Sports Injury Alert and that he would be a managing editor at Fantasy Pros. I was happy, proud, jealous, and sad all at once. If I could have held out a few more months, what would have been different? Was the pay-day large? Blaine wasn't able to talk about the details of the deal and I didn't press him, but I wondered. I wondered if I had given up, if I had walked away from something hard like I had done so many times as a kid. I remembered quitting soccer when I was little because it was too much running. I remembered quitting football when I was a few years older because it was too much hitting. Now, had I quit this company because it was hard?

It took me years to evaluate this situation, but I think I understand now that it wasn't just about it being hard. Running a company on the side is one of the hardest things an entrepreuner can do. Had we been a funded startup where all of our focus was on the company, would have had the same level of burn out? Maybe. Or maybe it would have been a different type of burn out. Or maybe it would have been fine. All I know for sure is that by trying to juggle Sports Injury Alert alongside a day job and family life, I had put myself at a disadvantage. I would learn from this with my next two companies, ensuring I quit the day job and focused all my work energy on each of them.

The Fantasy Pros acquistion is a source of bittersweet pride. My ego wishes that the press release included my name. I had spent so much time courting Fantasy Pros, but I was not there when the deal got done. Blaine brought it across the finish line, and I was not there. But I'm still so damn proud of what we accomplished. Blaine and I built something from nothing. We competed against well-capitalized heavyweights. We made an impact. And as far as I know, Blaine still works for and loves Fantasy Pros.