When Kendall Baker spearheaded content at media company The Hustle, he found it increasingly difficult to follow one of his loves: sports. It was the first time Baker had worked outside of sports as he held previous positions at ESPN, Bleacher Report and ticketing company Gametime United before moving verticals in Jan. 2016.
The cadence had changed and evolved to the point where sports information was now largely pushed to consumers and fans, he said to Sports Business Chronicle. During Baker’s 15 months at The Hustle, where he launched its widely-read daily newsletter, he was consistently fighting to stay connected.
“It was pretty clear to me that I needed to get back into sports,” said Baker, who added that the idea for founding a sports media company percolated during his 2009-13 stint at the University of Pennsylvania.
What that looked like exactly and when he’d venture down the entrepreneurial path remained to be seen. Yet, now with a blueprint in tow for how to build a daily newsletter from scratch, albeit in a different vertical, Baker said he had the confidence to strike out on his own. Sports Internet was finally born on Sept. 11, the first Monday after the launch of the 2017 NFL season.
Baker’s hypothesis, at least initially, was simple: based on his experience at The Hustle, he could summarize yesterday’s sports headlines in email form. From there, he communicated to early subscribers that his approach would be experimental in the first month or two, testing different email formats, number schemes and color patterns as he and his readers journeyed forward together.
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He estimated that he tried eight different email formats in the first two months, one that had a similar look to The Hustle with three to four deep-dive stories per day. Still, sports was different than technology and business — there were frankly more stories across the global sports landscape. He needed to go deeper. Another newsletter template was inspired by theSkimm, the female-oriented newsletter founded in 2012.
Baker landed on a No. 1 to No. 8 format along with a pink and yellow color scheme to give the 7 a.m. newsletter a unique look. Hyperlinks appeared in bright pink, too.
“I didn’t want to be normal,” he emphatically said, citing Bill Simmons’ The Ringer as an outlet that had a distinguishable brand.
The numbering format made it easier for subscribers when they were scrolling through the newsletter, according to Baker. He explained that with the one to eight format, he could provide more sports coverage than was necessary for the non-obsessed fans but enough for the crazed fanatic, a win-win for everybody.
“If I have a reader who doesn’t give a crap about the NHL, and my second story is about the NHL, and they see that immediately because there’s a tag on top, and they skip it, that’s fine,” he continued. “If they hate the NBA also and that’s in number four and number five, and that’s all that was in the newsletter, maybe they’d get nothing out of it. I basically try and cover all of my bases. … I want there to be at least one thing in here you didn’t know, or you’re glad you saw.”
For example, a newsletter from March 2 started with a ‘Major League Baseball is A-Rod’ headline and shed light on the increased home run rate, which arguably was attributed to juiced baseballs.
At No. 2 was a detailed account of Arizona men’s basketball coach Sean Miller denying an ESPN report about his alleged phone conversations discussing a $100,000 payment for incoming freshman DeAndre Ayton.
Each day, No. 3 is reserved for trending news via social media, possibly a buzzer-beater, viral video or even a quirky GIF of ESPN’s Darren Rovell, who was featured that particular day. #BoxScoreThoughts slotted in at No. 4 while No. 5 centered around five bullets from the NHL. No. 6 highlighted a story about the Golden State Warriors’ 70-year-old truth-teller and assistant coach Ron Adams. Baker reserves the number for a link to the best article he uncovered on the Web the previous day. Top sports articles from business, technology and media follow before a final question for readers rounded out the newsletter.
If the above sounds like a daunting task, it’s because it is … to the tune of six to seven hours, Baker says. He’s on the brink of emails being clipped by Gmail.
Then again, though, the Sports Internet daily newsletter is his product at this point.
Said Baker: “You wake up in the morning, and Sports Internet is this robust thing that you can open at your leisure. When you do, you can sit down with it, and you read it from top to bottom or you scroll through. You see something in number four and then you end up going down a rabbit hole about that. That’s the feel I’m going for, this robust, longer thing every morning that feels like a piece of art, in a way, that you can do with what you want.”
Baker highlighted that the tagline ‘SportsCenter in email form’ painted the best picture for what he was trying to create with the daily newsletter. For those sports enthusiasts in their mid-to-late 20s and early 30s, it arguably reminded them of their childhood. Similarly, it’s viewed as an all-encompassing portrayal of the sports world.
The Worldwide Leader, Bleacher Report and Barstool Sports are among some of his competitors in addition to the regular sports publications, he explained. Specifically, though, SportsCenter AM is the competitor in Baker’s eyes.
When asked if he likens Sports Internet to a condensed version of Twitter, he said he had thought about it, but that the comparison is much more difficult to put into a sentence.
Though a majority of Baker’s experiences lie in sports media, he speaks like someone entrenched in Silicon Valley, where a prioritization is placed on talking to users, iterating and ‘scaling the unscalable’, as the technology community says. A media company operating like a technology startup some may say. Responding to readers’ emails has also been a key priority since launch, he added.
“If someone responds to your newsletter and then you get back to them and get a conversation going, I don’t know if it’s permanently, but the deliverability will increase for them,” said Baker, who declined to comment on subscriber numbers.
“People don’t naturally expect for a newsletter to respond, and they forget that there is a human behind it. … When people don’t expect that to happen and it happens, they’re like, ‘Oh, whoa’. If you have one conversation with them, they’re going to start opening everyday. Now, they feel a little more personal connection to you. They know you a little bit more. There’s just a lot of benefits to it, and then it’s great to get feedback, listening to your customers.”
For the near future, the Sports Internet model will continue to be newsletter-centric as Baker curates the Internet. Constantly iterating and tweaking his product will be top-of-mind over the coming months. He alluded to integrating the company’s website into the newsletter, where No. 6 in particular would feature a longer-form article by Sports Internet.
It’s the one-product-at-a-time deliberate approach, according to Baker, but podcast and video are possibilities, with all of the various mediums ultimately being in sync with one another.
Though he’s just six months removed from launch, Baker described a future where the newsletter could be the “sports world’s landing page,” possibly forming relationships with different sports-centric publications and companies via longer-form integrated partnerships.
For now, Baker’s a one-man show aside from the occasional contributor. He’s focused on the bootstrapped operation but did say he’s had discussions with venture capitalists, though he didn’t delve into specifics.
“My heart is really in building something big and meaningful. In order to do that, you don’t have to raise money. If you do raise money and do it at the right time, it’s just gasoline on the fire,” he said.