So, What Really Happened To The Cauldron?

Thinking about launching your own media startup? You might want to consider my crazy story first.

Jamie O’Grady
The Cauldron
Published in
25 min readJan 14, 2019

--

The call came in late winter of 2013 from a New York City number I didn’t recognize. I had relocated to North Carolina two years earlier, but recruiters were still trying to lure me back to the Big Apple. I wasn’t remotely interested. The South had become home much faster than I ever expected — the people, the weather, the pace of life, the exponentially lower blood pressure.

The woman on the other end of the line introduced herself as Kate Lee. I had been recommended to her by someone in digital sports media, she said, and her company, something called Medium, was a recently-launched digital platform that was looking to incubate promising publications.

(Translation: She needed content. Good content.)

To that point, I had done a little blogging for the New York Times and Major League Baseball — more as a side hobby than anything else — and built a relatively small, but loyal social media following. No journalism degree. No experience as a Publisher or Editor-in-Chief. My coverage of the New York Knicks had led to a few guest appearances on WFAN-NY and ESPN Radio in New York, but I certainly wasn’t well known in the industry.

Five-thousand dollars a month. For three months.

That was the total funding Medium offered to conceive of and execute my vision for a sports website that would ultimately become The Cauldron. With just a three-month runway, it certainly wasn’t a lot of time or money to launch a national media startup. (And it was the primary reason why someone a lot more proven than me hadn’t already taken them up on the challenge.)

I had been working as a Wall Street lawyer for over a decade at the time, so it wasn’t about the money. Anything Medium paid me would be invested directly into the business. To be fair, it wasn’t even really a “business.” Not at first, anyway.

It was more of a scatterbrained concept:

Finding the time and energy to make a legitimate go of it would be no small feat. My wife was also working full time and sharing the demands of our toddler son and newborn daughter. And yes, there was my pesky day job as in-house counsel to a global investment bank to attend to, but no matter; I was determined.

We launched The Cauldron on June 1, 2014.

By we, I mean Andy Glockner and me, along with the dozens of freelance writers we initially commissioned to write stories and create content for us. Back then, our design sensibilities were, shall we say, nascent.

The practical reality was that The Cauldron never should’ve survived beyond the initial three-month run. Consider the competition we were up against: ESPN’s aforementioned Grantland, VICE Sports, Deadspin, and countless other fully-staffed and fully-funded media outlets with resources and distribution we had no way to emulate.

In fact, our funding was stretched so thin at inception, we couldn’t even afford an image license. Instead of posting pictures of the athletes and sports we were covering, we sourced nondescript royalty-free photos and clip art.

Still, even Deadspin’s resident wiseass noticed.

Somehow we managed to beg and borrow just enough content from sympathetic and hungry freelancers — some of whom had already established themselves in sports media, others who just wanted the opportunity to have their work seen on a national level.

Notice how I didn’t say steal, though. We paid our experienced contributors as best we could; some getting $50 per post, others up to and exceeding $1,000 per month in exchange for a weekly column. We also published aspiring amateur writers, too. The vast majority of them were unpaid, but we worked tirelessly to help them hone their craft and ensure that their work would be seen by a larger audience.

Andy and I published content at a breakneck pace; at least five 1,000-word-plus pieces a day (and often more than that), doing our best to not make any egregious errors — all while trying to ensure that our product was different than anything else out there.

It didn’t hurt that 20 or so of our better-known contributors trusted me with the keys to their social media feeds, allowing us to post “organic” links to our content directly from their accounts. People like Robert Silverman, Kevin McElroy, Howard Megdal, Greg Hanlon, the Kamenetzky Brothers, Colin McGowan, T.D. Williams, Tim Ryan, Tim Baffoe, and many others.

Can you imagine giving someone carte blanche to post from your Twitter account to build their business? Hell-to-the-no. Those writers’ collective faith in Andy and me enabled us to hit the ground running, and in retrospect, I’m not sure The Cauldron would have become what it became without that access.

Our use of writers’ social media accounts for distribution was never a secret. It was something we needed to do to succeed, and we never abused the privilege.

Andy and I dumped virtually every penny of the $15K of Medium funding into operations during those first few months. And while we started to gain some traction — we averaged around 250,000 unique monthly users by month three of the initial deal — it became painfully obvious that reaching Medium’s performance benchmarks was going to be next to impossible.

Back then, prior to the first of Medium’s endless company pivots, Ev Williams was focused on something called the total-time-read metric (“TTR”), a worthy, if ultimately fleeting content strategy designed to lure brands by touting how engaged the platform’s readership was. You see, if people spend a lot of time at Medium, then they surely will buy the products your company is hawking. Or something.

The problem with Medium’s TTR, however, was that The Cauldron’s traffic, however strong, wasn’t worth much to our bottom line unless people were spending significant time reading each piece. While that may seem like an insignificant detail, the rules surrounding Medium monetization at the time meant that we could only cash in on long-form pieces. Unlike other sites that relied heavily upon short-form aggregation of news and/or poaching content creators’ original work as click-bait, we couldn’t simply duplicate the seemingly successful business models of USA Today’s For the Win and The Big Lead, or Deadspin.

Posting real-time, short-form content simply wouldn’t have created revenue through the Medium arrangement.

In hindsight, though, we should’ve spent fewer resources on publishing so much daily long-form content. At the time, our audience just wasn’t large enough to digest five or more 1,500-word articles each day. And while it felt great to be paying journalists and aspiring bloggers to write, we were essentially lighting our meager funding on fire.

Investing exclusively in athlete-direct and viral videos would have given us a lot more bang for our buck.💡

Making matters worse; though we had demonstrated clear growth since launch, it was communicated to me by Evan Hansen at Medium that unless we exceeded certain TTR expectations by the end of our second three-month term, the Medium funding would not be renewed. Six months had come and gone in an instant, and we were essentially finished before we even had a chance to get started.

And then it happened.

Former NFL punter Chris Kluwe, unbeknownst to him, singlehandedly saved The Cauldron.

You probably saw it. Everybody in the tech and gaming world sure did. Kluwe’s epic, expletive-laced breakdown of the Gamergate controversy, published on October 21, 2014, went viral, garnering over 1.5 million page views.

I paid Chris $2,000.00 for that story. It was the ultimate gamble, mainly because that money represented the very last of the funds in The Cauldron’s bank account. Medium had planned to pull the plug on Halloween, just 10 days later.

Only, The Cauldron’s demise was not meant to be — not then, anyway. That one story paid out a $40K return on investment(!), and in an instant, Andy and I went from bankrupt to flush with cash to fund November operations and beyond.

We were literally that close to going out of business.

The next twelve months were an absolute blur. 19-hour days, very little sleep, a barrage of submissions from a rapidly growing legion of 1,000-plus crowdsourced contributors, and a relentless obligation to keep churning out content.

To the average websurfer, how the sausage is made doesn’t really matter. But for any publisher, keeping pace to ensure the audience comes back for more is a daunting challenge. It just doesn’t stop. Ever.

Even when I wasn’t actually creating or editing content at The Cauldron — or singlehandedly running the company’s social media accounts prior to the arrival of the indispensable CJ Fogler — I was busy recruiting even more writers and multimedia content creators. All while establishing and maintaining relationships with professional athletes, their agencies and management firms, brands, and larger media publishers.

Owing to the magnitude of the athletes I was able to secure, traffic to the site was way up, too.

There was Josh Flash Gordon, the troubled Cleveland Browns wide receiver, who pushed back on what he felt were unfair criticisms of him by the media. His story went absolutely nuclear, and took over coverage of Super Bowl XLIX in 2015. The Cauldron was all over ESPN, FOX Sports, Sports Illustrated and virtually every national sports media television show.

There was two-time NBA MVP Steph Curry, who explained how being typecast as weak and small only fueled him to prove the doubters wrong.

There was Stanley Cup Champion Sidney Crosby of the Pittsburgh Penguins, who shared just what motivates him to keep atop the NHL mountain.

There was NFL All-Pro running back Le’Veon Bell, whose story at The Cauldron led to a video profile at the NFL Network.

There was UFC fighter Chael Sonnen, who went public with his steroid use. And unabashedly defended it.

There was NFL offensive lineman kasey studdard, whose deeply personal story of having been called “retarded” as a developmentally disabled child inspired countless readers.

There was the enigmatic-but-always-entertaining Cleveland Cavaliers guard JR Smith, who finally learned why winning was the best medicine for his controversial reputation in the NBA.

And there were scores of other big names, too.

With our best-in-class athlete-direct content, we broke news, revealed deeply personal insights, and delivered raw, compelling stories that couldn’t be found anywhere else.

When The Players’ Tribune announced its intention to enter the market with the undeniable cache of Derek Jeter, Kevin Durant, and Kobe Bryant — and millions of dollars of Excel Sports Management’s investment capital — we were still in full bootstrap mode, wholly reliant upon the quality of our output and the relationships we had built with our subjects.

That’s not to say that we were better than TPT (or anyone else), but given our limited resources — in manpower, experience, funding, distribution, and total content output — our traffic and engagement dwarfed the competition’s.

And it wasn’t just athlete-direct content, either. We published stories that received industry-wide recognition and acclaim.

Like Julie DiCaro’s chilling and personal account of online harassment, a trend that has only gotten worse for many (female and male) journalists since her piece was published.

Or Colleen Curry’s incredible story about what it was like covering the Jerry Sandusky trial for ABC News for a year.

Or Claire McNear’s amazing journey into the NFL heart of darkness, or, as everyone else knows it: The Oakland Raiders’ Black Hole.

Or this crazy Trevor Kraus story about sneaking into the Super Bowl, the World Series, and just about every other major sporting event.

And so many more.

And we created quite a few videos that received millions of views, too:

Eventually, our ceaseless labor paid dividends, and by late 2015 we’d secured a distribution relationship with Time Inc.’s Sports Illustrated. And while SI.com had long since been eclipsed in the digital sports media landscape by ESPN, Bleacher Report and Yahoo!, Andy and I felt validated by the arrangement — buoyed, really, by the credibility such an affiliation granted The Cauldron.

SI.com, by all accounts, should’ve been a perfect partner for us. We were excited to access their significant distribution to raise our brand’s profile, and in turn, they got to run a variety of groundbreaking content that would, in theory, be easily monetizable, and attract a younger audience — something the suits at Time were keen to do.

For a variety of reasons, though — Time’s internal restructuring, changing editorial directions, management turnover, a lack of vision, crippling corporate bureaucracy — the relationship never created a sustainable revenue stream for either side. That’s not to say the parties didn’t operate with the best of intentions, at least initially, but large organizations like Time are ocean liners: They don’t turn on a dime. In this case, it didn’t turn at all.

Ultimately, despite Sports Illustrated’s clear interest in and excitement about The Cauldron’s potential, an outside publication not wholly owned by Time was simply never going to garner the necessary internal support — the sales team’s buy-in, specifically — to fund and grow the business.

And I knew that from the beginning. Each side was getting something out of the arrangement, and I was content with what it was.

As far as I was concerned, The Cauldron had arrived.

Hang around social media long enough — especially as a member of the weird and wonderful world of sports media — and you’re bound to suffer, eventually, the slings and arrows of the trolls. (This is where our story gets a little sidetracked, but I feel it’s important, for the sake of context, to tell the entire story of The Cauldron.)

Google my name, and you’re sure to find — rather prominently — search results painting me as a key figure in a lightly-reported (and even less interesting) 2015 online “feud” with something called Barstool Sports.

Not familiar with Barstool, you say? As far as target demographics go, the site falls somewhere on the scale between “offensive, crass, and occasionally funny” and “OMG, please pour bleach directly into my eyeballs!”

Robert Silverman wrote a damning story for The Daily Beast about the culture at Barstool.

Deadspin Founder Will Leitch explored for New York Magazine what, exactly, Barstool is, and attempted to understand how something so awful can thrive.

Put a bit more diplomatically, Barstool has established itself as a player in today’s digital sports media world by cultivating a significant and loyal audience. And though their content isn’t everyone’s cup of tea, there is no denying that the company’s model has proven durable and lucrative. In fact, there was a time — before the Age of Trump — when I considered Barstool’s popularity to be a good thing for sports media as a whole.

Unfortunately, however, the people who run Barstool — and the readership they incite — don’t take very kindly to criticism, no matter how valid it may be.

On January 7, 2016, I greenlit a piece by Nick Stellini titled, “How Barstool Sports Uses Social Media As A Weapon.”

Some people liked it. Others thought it was a hatchet job. A public, rambling, incoherent airing of private direct messages soon followed. As did physical threats made in video form and copious amounts of manhood-measuring — all of which fomented a perception by some that #BarstoolVsCauldron was a “thing.”

Actually, here … see for yourself:

Amazingly, on the same day the Stellini piece went live, Barstool announced it had been sold to the Chernin Group, supposedly for multiple millions of dollars. And the man behind Barstool, something called Dave Portnoy, felt it necessary to take time out of what should’ve been the best day of his life to inform me of his fiscal well being.

Back then, Portnoy was already well known for being the attention-seeking egomaniac who once posted photos of Tom Brady’s naked two-year-old son online, but his infamy had only grown.

You see, a story at The Cauldron that questioned Dave’s self-anointed greatness — on his day of Internet triumph, no less — meant nothing less than an act of war. An act that could only be responded to in kind: By unleashing his Twitter army to deliver a seemingly never-ending torrent of invective on social media directed at the author of the piece, at my staff, and at me, my wife, and my children.

(Dave Portnoy, Founder of Barstool Sports, all-around nice guy.)

The irony of Portnoy, his staff/minions, and social media sycophants launching into a full-on assault of online harassment was thick, to say the least. Particularly in light of the topics that had been credibly addressed by Stellini’s story hours earlier.

Still, I tried not to take the defacement of my Twitter mentions personally. These were the juvenile musings of the so-called “Stoolies,” a predominantly white, 20-something, Boston-centric digital army of Bros who were and remain desperate for some sense of digital validation by Barstool’s founder.

While Barstool’s staff launched an endless barrage of @s and subtweets intended to put me and The Cauldron in our place (I guess), Portnoy saw fit to flex his one-upmanship muscles.

Naturally, only a Ford Bronco would do.

This was Dave’s car just for when he goes to Nantucket. Where people with money go. Because he had money. Nantucket money. ¯\_(ツ)_/¯

Not surprisingly, Portnoy and his cohorts habitually disclaimed (and still do) their cabal of loyalists while simultaneously blaming the rest of us for “not getting” what Barstool does, as evidenced by a revealing interview Portnoy gave to Entrepreneur back in 2013:

“We don’t back down from controversy — we fan the fires. People think we go out of our way to create it, but we don’t. We’re not trying to gain new readers by being crazy-outrageous. Our readers get what we do, and I don’t think about what it’s going to look like to the outside world. I don’t really care.”

We fan the fires. His words, not mine.

But Barstool’s success isn’t the story of some well-meaning web dreamers whose creation took on a life of its own. They’re proud of who they are and what they’ve become. As Portnoy himself admits, it’s as much about the community — Donald Trump’s “so goddamn sick & tired of all this liberal PC bullshit” community — as it is the clickbait that fosters it.

In reality, Portnoy’s mission has never been to carry the flag of the anti-PC, fun-loving millennial crowd with valorous altruism. His primary goal — beyond achieving some degree of celebrity, if you can call it that — is to publish stuff and try to profit off of it. Which, in and of itself, is totally fine. This is the exact same thing any other media company does — except most of them don’t end up fueling loud, misogynist hate-armies on Twitter.

You know, by publishing things like this:

Now, years later, it remains undeniable that the underlying point of Stellini’s piece has been validated a thousand times over. I didn’t err by approving the story, I was wrong to extend what I thought was a modicum of professional courtesy by giving Barstool a head’s up about the story in advance.

I owed no such courtesy.

Someday, karma will bite Portnoy in the ass. It’s inevitable. You simply cannot be that awful a human being and not have it catch up with you eventually. And when it happens, I hope someone lets me know.

On February 22, 2016, I received some rather dispiriting news. While The Cauldron’s partnership with Sports Illustrated remained intact, word leaked that Medium had landed a very big fish to add it its portfolio. Bill Simmons was coming to Ev Williams’ shiny publishing platform, and a large contingent of the former’s ESPN/Grantland staff was presumably coming with him.

The Ringer, it was going to be called.

“I’m really sorry we couldn’t let you know in advance,” mid-level Medium staffer Saul Carlin reassured me on a hastily-arranged call. “This was negotiated at the senior-most levels of the company, and we had to keep it under wraps. We wanted to tell you before the official announcement, but trust me, this will be a good thing for The Cauldron. The more people that come to Medium for sports content,” he said, “the easier it will be for you to grow your audience.”

I was not at all reassured.

How in the hell was I supposed to compete with Bill Freaking Simmons, his audience, and his deep pockets? Would there even be room for two sports publications on the Medium platform? Wouldn’t Medium be motivated to get some return on its investment in him, making sure his content received preferential placement and social promotion? (As it turned out, the answer to that last question was an unequivocal yes.)

In fairness, I understood completely that Simmons represented a major coup for Williams and his top lieutenant, Edward Lichty. I knew that neither had any obligation to inform me of Medium’s plans in advance. Still, the news stung. Not only had I brought dozens of professional athletes to a Medium platform that wasn’t yet mainstream — you try explaining to DeAndre Jordan, Derek Fisher, or Dick Vitale what Medium was! — I’d also successfully deployed one of the first external-publisher URLs (thecauldron.si.com) in the Medium environment, a model that the company had hoped would exponentially grow the platform’s reach and utility.

And yet, no head’s up. No introduction to Simmons. No consideration given, it seemed, to the idea of marrying his content plan with my own to form a product that could upend the existing sports content marketplace.

Impossible? Overly optimistic? Unrealistic?

Perhaps, but I certainly felt like The Cauldron’s traffic and brand awareness at least warranted a discussion about the potential synergies.

(Not surprisingly, the marriage between Medium and Simmons ended up flaming out in short order.)

Even worse, on a personal level, working 19-hour days in two full-time positions was taking its toll — physically, mentally, emotionally, and on my ability to be present for my family. I was having trouble sleeping, my mind ceaselessly racing about what I could do to grow the business; about what keys I was missing to ensure that The Cauldron would “make it.”

Like many inexperienced startup founders, I was incapable of appreciating what I’d already accomplished because I was too busy worrying about what came next.

And when the reality of the business failed to fit within the neat little paradigm of expectations I’d set for myself, I began to lose confidence.

What I didn’t understand — what I didn’t fully understand — was that nothing in this life is handed to you. You have to go out there and bend the world to your will. Early success does not portend scalability, profitability, or sustainability. No one owed me anything; not Medium; not SI; certainly not Simmons; no one. I simply needed to regroup and turn what felt like a missed opportunity into something positive.

Lo and behold, four days later, opportunity came knocking.

There are certain days in your life that stand out from all the others. Your college graduation. Your wedding day. The days your children are born. The day you find out you’re going to be a millionaire.

I literally almost fell out of my chair when the email hit my inbox.

Here I was, having worked myself to the brink of exhaustion for over 18 months, having missed the vast majority of my two-year-old girl’s life, and everything was about to come up Milhouse. This wasn’t just any $2.5M offer, either. The Cauldron would be acquired by — and I would work for — one of the industry’s most respected companies, a firm with a massive foothold in sports, entertainment, media, advertising, and content creation.

Still, while I was obviously excited at the prospect of landing a deal of that magnitude, I did my best to temper expectations. Until a deal is closed, it isn’t.

Sadly, the next 60 days would see a slow and steady withering of the deal parameters; the goal posts consistently being moved from one day to the next by the acquiring party. Due diligence requests were expediently fulfilled, only to be met with ambiguous and illogical assertions that The Cauldron’s performance did not meet the acquirer’s arbitrary performance benchmarks. There were conflicting accounts of not wanting to use The Cauldron’s assets for anything more than marketing, and that the company mostly just wanted me.

Naturally, it struck me as odd that the party offering to buy my company was on one hand effusively praising what Andy and I had built, and on the other invalidating its worth. My incredulity eventually morphed into discontent as the negotiations slid further and further into oblivion.

Despite initial assurances that key staff members would be able to join me at the new enterprise — Andy and SportsPickle’s DJ Gallo, specifically — backtracking ensued, and a decidedly confrontational tone was conveyed by the acquiring party’s lead negotiator, ostensibly over why I needed to remain loyal to those who had help me build The Cauldron.

Discussions broke down entirely when I was presented with an untenable revised offer — for around 10% of the original deal. This, after I’d shared my existing business plan and a variety of new content creation concepts, some of which were subsequently deployed by the acquiring party.

It was a fairly devastating experience, not only for me, but for Andy, too. Despite the platitudes, the acquirer had only considered us vessels to advance their own interests. There was no legitimate respect paid, nor was there a shared interest in building something great.

But that didn’t mean there weren’t other whales out there to chase.

Anyone who’s ever tried their luck at fundraising knows it takes an incredible amount of time, effort, and patience to convince investors to part with their money. And meetings. Lots of meetings. Endless Powerpoint-tinkering with investor decks leads to conference calls and in-person pitches, most of which conclude with outright no’s or lukewarm maybes. In short, securing funding for your startup is not for the faint of heart. (Or those who don’t handle rejection well.)

I had one such meeting in mid-2016 with Vasu Kulkarni of CourtsideVC, a venture capital firm that “invests in early-stage founders that are transforming the intersection of sports, technology and media.” Kulkarni, as it turns out, had been an admirer and supporter of The Cauldron from the beginning, a revelation that initially made me optimistic that Courtside would invest.

Sadly, that wasn’t in the cards.

The problem, Kulkarni told me, wasn’t that The Cauldron wasn’t an excellent media publication; it was that we couldn’t provide the 20–30x return on investment his fund needed to justify taking an equity position. He conceded that I’d built something unique with very little resources and was impressed that I had done it while working another full-time job as a lawyer, but he didn’t sugarcoat things, either.

He went on to explain that I was likely to be met with the same resistance from other venture capitalists and/or angel investors, too. The Cauldron, though having undeniably carved out a fine niche in the sports media world, was really just a content creation experiment — largely dependent upon my ability to get athletes and influencers to contribute.

Sure, we had a robust social media presence and had produced a bunch of viral videos, but at the end of the day, there was no there, there. No technology. No standalone, proprietary platform. No way to reach critical mass on the distribution side without Sports Illustrated or another large partner.

His assessment was bleak, but all was apparently not lost.

Kulkarni offered to introduce me to someone with his own sports media company — let’s call him James Yoder — who was also trying to fundraise. According to Kulkarni, Yoder had purportedly built up a decent-sized user base for Chat Sports, his mobile phone app company. (The app was a relatively unsophisticated and nondescript knockoff of Bleacher Report’s Team Stream aggregation application.)

Actually, Yoder’s numbers were more than “decent sized,” if you take his word for it. 🤔

(Yeah, no.)

100 million monthly users?! That’s, like, Bleacher Report, ESPN, and Yahoo! traffic territory. And no, I had never heard of Chat Sports, either.

Anyway, according to Kulkarni, Yoder’s biggest problem wasn’t average monthly users or site traffic, but credibility in the sports media marketplace. That, and an inability to create the kinds of compelling in-house content that appeals to brands and advertisers.

If we could figure out a way to combine forces — combining Yoder’s existing technology and supposedly endless connections with investors with my existing brand equity and athlete relationships — Kulkarni surmised we just might just be able to kill two birds with one stone to create an attractive, turnkey investment opportunity.

It seemed like a workable theory: Athlete-Direct Content + Existing Technology = A sports-loving venture capitalist’s wet dream, basically.

Only, you know, best-laid plans and such.

After the initial introductions were made by Kulkarni, Yoder and I discussed high-level parameters for a deal by phone, text, and Slack almost immediately. He was extremely enthused about the possibility of joining forces — almost overly so — so it seemed perfectly reasonable when he suggested flying to North Carolina to meet in person.

When I picked him up the airport, Yoder seemed normal enough. Clean-cut, nondescript white dude, early 30’s with a just barely-still-there midwest accent. He fashioned himself a tech insider, habitually name-dropping the “heavy hitters” he knew or had access to. He spoke at length about organizing seminars with the owner of the Cleveland Cavaliers, billionaire Dan Gilbert. He said he had a personal relationship with Jim Harbaugh, coach of the Michigan Wolverines.

His Facebook pictures seemed to back it all up.

(James Yoder, left, and Dan Gilbert, right)

None of this is to say I picked up a bad vibe from Yoder, exactly, but it was immediately clear that he was not cut from the same cloth as me, and at no time during the hours we spent together — or anytime thereafter — did I get the sense that he knew much about creating good content.

And that was fine by me; we were joining forces to fill out the pieces of a greater puzzle. He didn’t need to be a “creative” — I had that side of things covered.

And, admittedly, my fundraising abilities had thus far proven, well … unproven.

By the end of Yoder’s N.C. visit — after walking through our company’s respective business plans and performance metrics, and fleshing out how a union might look — we loosely agreed upon the terms of Chat Sports’ acquisition of The Cauldron:

  • Sale of The Cauldron and all of its assets for $XM (in cash and equity in the new post-merger company that would be formed).
  • I was to be installed as Chief Content Officer of the new company with a generous compensation package, including salary and bonus structure.
  • The new company would open a North Carolina office and make five to seven initial hires — primarily focusing on athlete-direct video, podcast, viral and written content. The goal was to leverage massive player distribution over social media to entice brands to spend with us, essentially executing The Cauldron’s business plan that was disseminated to investors in early 2015.
  • The new company’s first two hires would be DJ Gallo and Jim Cavan, each of whom were original staff members of The Cauldron, and individuals I considered indispensable to any resultant enterprise. Andy’s role was TBD; not because I didn’t want him with us, but because relocating from Denver was not a plausible scenario for him.
  • The deal would be wholly dependent upon Yoder’s ability to close a ($YM) Series-A fundraising round for the new company — an entirely reasonable condition, given the need to secure funding in order to execute any of the planned content expansion initiatives.

Yay, we did it! 🤔

Only, nothing went according to plan. Unless the plan was supposed to include convoluted lies, forged term sheets, fake lawyer emails, defamation, and tortious interference.

In that case, #AchievementUnlocked!

In late February, Daniel Roberts of Yahoo! wrote an exhaustive investigative piece on everything that happened after the initial deal was signed. It remains a well-reported piece, and it’s worth your time.

Yoder’s side of the story used to exist here, but it has long since been deleted:

Chat Sports has actually been in the news before (via Awful Announcing):

This isn’t the first controversy for Chat Sports. They took a lot of fire back in December 2015 for a story about Ohio State head coach Urban Meyer being offered the “largest contract in NFL history” to coach the Cleveland Browns, something that was picked up by major media outlets, including ESPN’s Pardon The Interruption. That story came from “Mack Ferguson,” who had one tweet and 10 followers, so he seems like a good candidate to be one of those fake writers Yoder talked about. They’ve also been criticized for plagiarism and fabrication.

And last week, the University of Michigan’s Athletic Department took the virtually unprecedented step of publicly warning its student-athletes to stay away from Yoder:

As you probably guessed by now, the deal ultimately fell apart. It would probably be fairer to say that there never was a deal; that Yoder was essentially spinning yarn on the hope that he could land funding before I found out what he was up to.

Nevertheless, I wish that I had been a better judge of his character. I wish Kulkarni had instead recommended me to the founders of The Athletic, a company he had actually invested in that would have been a much better fit for a partnership with The Cauldron. And I wish that the Sports Illustrated executives I had treated with respect and professionalism saw fit to reciprocate by letting me know that Yoder was defaming me in written communications to Time Inc.’s senior management.

Unfortunately, when you’re running a startup, 20/20 hindsight doesn’t mitigate your prior miscalculations. All you can do is learn from those experiences and apply the lessons to challenges you will face down the line.

In the end, it doesn’t much matter who believes who in the sordid mess that was The Cauldron’s final days. I know who I am, I know what I stand for, and I know how I comported myself.

So what happens next?

I’m certainly not the first to say it, but the digital media business finds itself in an extremely tenuous position. Unless you’ve got deep pockets, built-in distribution, and a way to generate revenue without relying upon clicks, it’s a cold, dark world out there for startup publishers.

Andy and I assumed that good content would win in the end. Maybe we will be proven right someday. Maybe The Athletic’s subscription model will be the answer. Maybe ESPN and Bleacher Report will be the last men standing. Honestly, I haven’t the slightest clue how the industry will evolve.

Running The Cauldron for three-plus years was a dizzying, wild, validating, rewarding, frustrating, disappointing, challenging, and mettle-testing experience. I gained invaluable experience as a publisher, editor, and manager of a large staff. I met and worked with world-famous athletes, their agents, and professional sports team owners. I navigated the topsy-turvy world of digital media, and eventually figured out what to do (and not to do!) when you’re trying to land funding.

And despite the failure of The Cauldron, I remain extremely proud of what we built. I am hopeful that Andy Glockner, DJ Gallo, and Jim Cavan are proud, too; I could not have done this without them.

I also hope that everyone — there are far too many to list individually — who was involved with The Cauldron at any level came away with a positive experience. I did the best I could with what I had to be responsive to our content creators and to help them hone their craft.

As for our loyal and amazing audience, I remain grateful for the support. I hope that you found The Cauldron to be engaging, thought-provoking and unique; just like we set out to do at launch.

✌Jamie

--

--