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Musings: The future of The Athletic, and the journey to The Daily Six

On Thursday, it was announced that The New York Times was purchasing The Athletic for $550 million. What do I think about the future of the company? And do I have any regret over not being a part of it?

There was no game last night, and Friday is typically a slow day for engagement anyway. I'll instead use today's musings to provide some thoughts about the future of the company I spent nearly half a decade with, and one that I owe a great deal of gratitude to. This post is long, as yesterday's news was an oddly emotional day that caused me to reflect on a wild five years, and also may not be interesting to anyone, so feel free to skip it entirely. We'll return to our regularly scheduled programming on Monday.

Yesterday morning, a report came out that the long-rumored sale of The Athletic to the New York Times was complete, a $550 million deal that has the chance to drastically (Or not. We'll see.) change my old stomping grounds. A few hours later that deal was confirmed, an investor call was held and the deal officially announced to the world.

When news of the acquisition first broke, my mind couldn't help but turn to all the friends I made during my time with the company. I went through an acquisition before, during my previous life in the tech world, and it is a strange mix of being both excited and terrified, a perpetual state of being cautiously optimistic while also being unavoidably tense over mounting uncertainty. Even the best of acquisitions are nerve-racking.

The second place my mind went to was to think back to this teeny, tiny little company that I agreed to join back in the summer of 2017, and to reminisce about the journey that has led me to here.

Finally, my mind went to look towards the future, and to ask myself whether I had any FOMO over not being a part of it anymore.

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When you hear the word "acquisition" there's one word that immediately comes to mind: "layoffs".

That association exists with good reason. A recent study by the Harvard Business Review found that 30% of employees are deemed redundant when firms in the same industry merge. That's obviously not directly applicable to this situation, but it's understandable why the unknown creates so much fear and tension, especially among the rank and file. That's true even if you have faith in the company's leaders, and faith in the acquiring company's vision.

For me those employees aren't a liability on a balance sheet. They're a friend, a valued former teammate and, in some instances, a mentor I owe a great deal of gratitude towards. I am hopeful that the acquisition works out for the best, and intrigued by the potential of what it can become, while still being concerned for people I care about. It's just unavoidable.

That being said, while acknowledging that I have no insight into the thinking of The New York Times' upper management and what their long-term plans are with The Athletic, I do believe that the Times is (theoretically, at least) a pretty good landing spot for The Athletic.

First, they've got a ton of cash on hand, upwards of $1 billion in cash, according to this write-up. While that doesn't guarantee the long-term job security of everyone at The Athletic, it does at least provide some hope that the Times can keep The Athletic operating in the red longer than it could have been if it remained independent. It also shows that they can put resources behind it to accelerate its growth, if they choose to do so.

Second, there isn't much overlap between the Times' sports coverage, which is more focused on the intersection of sports and the real world, with The Athletic's style, which caters much more directly to sports fans.  I think The Athletic fills an obvious void in the Times' portfolio, and increases the strength and breadth of their digital empire, making a more enticing, NYT+ style bundle possible in the future.

I think having The Athletic available to them can add value to their core product as well. Even if they don't want to increase the quantity of sports coverage in The New York Times proper, having a paid staff member at virtually every sporting event in North America can be beneficial for when national stories unexpectedly break out.

There have been rumors surrounding The Athletic's future for the better part of a year now, and there was a detail on the NY Times investor call last night that made it obvious why: the Times estimated The Athletic's operating losses at approximately $55 million for 2021. That's not entirely uncommon for VC backed companies in the growth stage of their lifecycle, but it did mean something was likely to give going forward.

When you line up all of the potentially viable paths for The Athletic in 2022 and beyond – raising more money from investors to keep them running as-is, massive cuts in the operating cost (aka staff) to limit the losses, selling to one of the other rumored suitors (Axios/FanDuel/Draft Kings), or selling to the Times – there's reason for optimism that this could end up being the best pathway forward* for them, not just as a company but for the job security of my former colleagues.

(*Note: that doesn't necessarily mean The Athletic, as a product or as an employer, will be better than it has been up to this point. It could be. Or the Times' acquisition could simply be the best of the less than ideal options available to them. We truly don't know which it is right now, and may not for a couple of years).

Again, reasons for optimism, mixed with unavoidable concern.

One thing that does put me a little bit at ease is that I do believe in Alex Mather, the co-founder and CEO of The Athletic who will remain with the company as general manager, and co-president, of The Athletic under the Times.

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I have a little bit of a different relationship with Mather than some at the company do, for two reasons. First, he grew up in the Philadelphia area, and was born with the unfortunate disease of being a long-suffering fan of the Philadelphia teams. That's something I can relate to.

More importantly, back when I came on board, The Athletic wasn't the juggernaut it has since become. There wasn't a big, established media entity to prove their vision, nor was there the prestige of one to draw me in. There weren't layers and layers of editors and directors to give me their watered-down spin on the company and its mission. It was quite the opposite of that, in fact: it was just some guy with an idea, given a little bit of funding to see if it could work, who had to convince me to believe in that vision, and to believe in him as the person to lead us there.

Mather first approached me about potentially writing for his new venture back in January 2017, the very same day that Philadelphia magazine closed down its sportswriting department. The Athletic existed in just two markets at the time, Chicago and Toronto, with plans to launch in Cleveland soon. I was dead set on covering the Philadelphia 76ers, so there wasn't any kind of an arrangement that made sense at the time, and two weeks later I launched my own subscription newsletter covering the 76ers through Patreon instead.

Mather and I remained in touch over the coming months, chatting about the industry at large, the future of The Athletic and my experiences running my own subscription newsletter. By June, Mather had just about secured additional funding and was looking to expand into Philadelphia, and wanted to gauge my interest in helping launch The Athletic in Philadelphia when the new round was finalized.

The Athletic was now up to three cities (Cleveland launched in March 2017), but it was still hardly a household name. It was far more of an interesting concept than any kind of an established player in the media landscape. This was more than a year before the company hired Shams Charania, and a full two years before John Hollinger's arrival. This was well before Jayson Stark joined The Athletic. In fact, I played a small role in that recruiting effort (Or, at least, he humored me into believing our chat was helpful in any way. In reality it was probably more me trying to hide the fact that internally I was saying "oh my god, that's Jayson Stark, what am I doing here" the entire time).

There was no national staff to rely on, and no name recognition to drive our subscriptions.

With The Athletic having only raised a little over $2.4 million prior to that point, there wasn't a massively long safety net to count on, either. We had to succeed.  On top of that, my Patreon had done far better than I expected and, for the first time in my career, covering the Philadelphia 76ers was my full time job.

This is a long-winded way of me saying that it wasn't the security of an established company or the lure of a media heavyweight that drew me in. In fact, the success of my newsletter had created significant resistance to change. I was my own boss, I was writing directly to the fans, and I had complete editorial freedom. It wouldn't be easy for Mather to pry me away from that.

Alex had work to do to convince that this fledgling company had staying power, and he had to convince me that we would have the resources needed to build out the rest of the Philly staff in a way that would lead to success. Paying for sports coverage was far from the norm at that time, so we had to be able to target the right people to round out the staff, and we had to be able to offer them the freedom to cover their teams in their own unique ways. He also had to convince me to trust that his vision for the future of sportswriting aligned with my own, and of how I wanted to cover the team.

Even after we started talks for real in June it took Mather more than a month to finally convince me to make the jump. I tend to be very deliberate and methodical (sometimes to a fault), especially as it relates to my career. But Mather, with his passion for the industry, his willingness to empower us as sportswriters and to allow us to develop our own voice and our own style, his commitment to building something unique and his vision on how to get there did eventually win me over, and I'm immensely glad that it did.

The boost that working for The Athletic gave to my profile, the connections it allowed me to develop over the years, and the freedom I was given to continue to hone my style have all helped get me to where I am today. More importantly, having a role in building out the staff and launching The Athletic Philadelphia, and watching it become a staple in the Philadelphia media market, truly was one of the highlights of my professional life, and immensely rewarding. It was an honor to be a part of that.

None of that would have been possible without Alex Mather who, at a time when his company was in its infancy and when success was still hanging in the balance, showed the faith in me that he did. I don't know if I appreciated that show of faith properly at the time, but I certainly do now, especially after having watched that idea of his grow into a half a billion dollar enterprise that became the second largest acquisition in the New York Times' history. He provided me with one hell of an incredible opportunity, and for that I will be forever grateful.

Which sort of brings me into another reason why I feel optimistic. If the Times does eventually decide to make cuts, numbers will matter, and Philly has always killed it in that regard. I don't want to get into specifics here, but back when we launched The Athletic Philadelphia we were given a target of how many subscribers to bring in over our first two years. It was a goal which, if we reached, would roughly cover our salaries.

We needed just 13 months to reach that number.

Obviously, things have changed drastically since then. The Athletic Philadelphia as an entity is no longer a thing, with writers now rolled into national sports verticals instead. The operating cost of the company has increased exponentially. But the staff that remains in Philadelphia – from Bo, Sheil and Zach to Charlie, Rich and Matt -- are all exceptionally talented, and have proven their worth in the market many times over. That eases at least some of my concerns about the acquisition.

Perhaps this is me trying to talk myself into optimism at a time of massive upheaval, but I'm genuinely hopeful, both for the future of the outlet and for the well-being of my friends and former colleagues.

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So, am I experiencing any FOMO that this didn't happen while I was still there? Or do I feel like I dodged a bullet?

Neither, really. I am intrigued by what working under the umbrella of the Times could have been like, but also confident that I am at the right spot for this phase of my career.

Obviously, the constant rumors of The Athletic looking for a buyer were in the back of my mind when I was debating my future over the summer. When I left in early December, did I know that a sale would come less than a month later? No. But when you really sat down and looked at all the variables, I thought there was a reasonably high probability of a sale coming in the near future.

Still, as I said above I do earnestly believe that the Times is a good landing spot for them. When talks with the Times seemed to break down last summer, I was concerned that the deal which was, in my view, the best option from an editorial perspective was now seemingly off the table.

The end result is that after the acquisition I'm now more encouraged about the future of The Athletic than I was three months ago, not because I'm ignoring the chance that being acquired by the Times poses a risk (those concerns were where my mind went to first, and where I led this article off with), but because there were risks in every pathway forward. This path, at the very least, has the chance to mitigate those risks, while also offering significant potential benefits to The Athletic as well. (Again, caveats about not knowing the thinking of upper management still applies).

Beyond the reasons I listed above about why the Times might be a good landing spot, they also offer a couple of benefits that would have intrigued me personally.

First, one thing I always wished The Athletic invested more heavily in was data visualization, especially as someone who uses data and trends to help paint a picture, but has no data viz skills to speak of myself. The Times is fantastic at that, and I would have loved to tap into some of those resources and expertise.

Second, one of the benefits to being truly independent is the freedom to pursue non-writing opportunities. Specifically, a little over a year ago I was approached about doing a video documentary, something that intrigued me quite a bit, but that I ultimately wasn't able to pursue because of a non-compete clause in my contract. The Times, it just so happens, has a world class video production squad, and while I have no idea how much overlap there will be in the content side, the prospect of working with something like that would have been enticing.

But at the end of the day my preference for going independent again would have been there regardless of what the future holds for The Athletic. My stance was never that the Athletic treated me poorly. The opposite, in fact. I was treated well, with a stable job for four and a half years, with more freedom than any other major outlet would have offered, and with the increased profile and visibility that came along with it.

My position was also never that The Athletic was a bad product, and I still believe in both its vision and its execution. When my contract was winding down I never reached out to other outlets, either national or local. The only debate was whether I was going to be covering the team for The Athletic or whether I would return to scratch that independent publishing itch, an itch that never truly left. Those were the two options that intrigued me for this phase of my career.

In the end, the chance to build something again, with complete editorial freedom, and to control my own destiny from top to bottom was a challenge I wanted to tackle once more, especially since I felt like there was some unfinished business from my last go-round as an independent publisher back in 2017.

Is there some FOMO for not being a part of The Athletic under The New York  Times? Maybe some. But there would have been much more regret if I elected not to pursue this route with The Daily Six.

Reflecting back on the first month on my own has only reinforced that I made the right decision. The loyalty that so many longtime readers showed by following me to a new venture is simply overwhelming. That loyalty is everything to me, and serving that loyalty has to be my true north. When I sit down to write I want to be almost solely focused on what I can do to be useful enough to convince you to renew your subscription. I think that is how I can do my best work, and how I can keep a role in this constantly evolving sports media industry.

I am incredibly grateful to Alex Mather and The Athletic for the opportunity they gave me, and have absolutely zero doubt that joining their upstart company was the right move for me back in 2017. I wish them nothing but the best, and hope this latest development works out well for everyone involved, from top to bottom.

I am also confident that this is the right place for me in the next phase of this journey, and hope that I can prove that to you all over the days, weeks, months and, hopefully, years ahead.

-- Derek