Good morning, and thanks for spending part of your day with Extra Points.
This newsletter is brought to you in part by by SherpaSports. See more info later in today’s newsletter.
Chicago/Illinois residents: I’ll be on WBEZ this morning around 9:30 AM CT to talk about the financial impact of March Madness, if that’s a thing you’re interested in.
I’m sad that I wasn’t able to make it to either Final Four this year. Family, business, and other responsibilities kept me in Chicago this season. One of those was the Online Media Association national conference, which was held in Chicago last week.
I don’t normally go to these sorts of things, but this year’s conference was in my town, I was asked to speak a few times, and you know what? I really needed a few days to talk shop with my peers and surround myself with the excited energy of news nerds trying to build something better amidst the ashes of the internet.
There’s a ton of other stuff to talk about right now, sure, but as I looked over my notes from that event, I really think a lot of my takeaways could very much be applied to college sports…whether you’re a coach, administrator, academic, or startup.
Live your values
Most of the folks that I talked with at ONA were either local reporters or niche independent publishers. These gigs usually don’t make that much money or offer much in the way of long-term professional security, which means that the folks who are throwing themselves into these jobs are often motivated by something other than maximizing a paycheck. That isn’t to say that they don’t care about making money (in fact, quite a bit of the convention was centered on helping people make more money), but that they care about other stuff more.
When I think of the most successful publications I know, the ones with loyal audiences that do meaningful work, I think they all share one thing in common. They know exactly what their values are, they communicate those values to their readers, and they strive to live those values every day.
For the bulk of local and indie news, I believe those values usually center on service. What can this outlet do to answer questions my audience has, surface information that is accurate, meaningful, and important, or seek to solve problems? Readers will trust somebody who they think is fundamentally in their corner, rather than in the pocket of advertisers, powerful special interests, or various platform algorithms.
Reasonable people can usually disagree about various policies or business strategies if they can at least point to how those policies are driven by those established values. But if your policy choices aren’t anchored in an attempt to follow those values, you can run into trouble…whether you’re a newspaper, a small business, or an athletic department.
In my humble opinion, this is a major problem with college sports reform and governance, as it isn’t clear what the real animating values of the institution are…or at least should be.
Here’s an example. According to Yahoo! last week, the NCAA basketball tournaments are almost assuredly going to expand in the near future.
Barring something unforeseen, “it will happen,” says one high-placed source.
According to a proposal socialized with members last year, eight games would be added to the current “First Four” played over Tuesday and Wednesday of the first week of the event. This new “opening round” — the verbiage used to describe it — would feature 24 teams playing in 12 games over the two days at two sites (Dayton and another). Those involved in the negotiations caution that plenty of this could change through the course of continuing talks with TV partners Warner Bros. Discovery and CBS.
The 12 winners of the opening-round games — likely six games pitting lower-seeded automatic qualifiers and six pitting at-large teams — advance to an awaiting 52 teams in the original bracket. Under this concept, eight teams are extracted from the main bracket, plus the eight new at-large selections from expansion.
So let’s ask ourselves…what are the values that are driving this potential reform? Is it service to the fan? That doesn’t seem to be the case, as virtually no fan group has been agitating for an expanded tournament field. Additional games, travel, and missed class time for more athletes doesn’t seem to line up with the professed goals of academic achievement, so that probably isn’t the key value.
I could potentially understand if actual value driving expansion was a belief in the magical egalitarinism of the NCAA Tournament, one that provides meaningful championship access to smaller programs with less revenue. But if expansion happens absent reform to the NET or existing scheduling/selection philosophy, the expanded field is almost assuredly going to skew more towards established P4 + Big East teams, with more low-majors seeing their tournament experience end before the main bracket.
I don’t honestly think tournament expansion is “good” or “bad” by itself. If God had a recommended bracket size that should never be altered, I missed that lesson in Sunday School. But if the actual reason for the expansion (politically placating the biggest conferences) doesn’t line up with the other values expressed during the tournament, well, fans get cynical.
There are lots and lots of potential college sports reform policies floating around. But without an agreement on what is actually supposed to drive any of this, besides just money, it’s almost impossible to evaluate those proposals on their merits. And if that doesn’t get cleared up, you run the risk of eventually alienating your audience. Like newspapers. Or boxing fans.
AI can be helpful without becoming a hysterical LinkedIn hype machine
Like almost all of my journalist peers, I do not use AI or LLM tools to write the Extra Points newsletter. I don’t use it for outline suggestions, don’t use it to “organize my thoughts” don’t ask it research questions about college sports business, punch up any paragraphs, or produce the core newsletter product in any meaningful way. Typos, terrible jokes, and mistakes are all regrettable, but they’re my mistakes.
I know very few writers who feel differently about using AI to produce their core craft.
But I don’t mind admitting that Extra Points, the business, uses AI sometimes. I used Claude and other AI tools to help prototype and develop some of our (free) Extra Points game offerings. I’ve used similar tools to segment and analyze some of our audience retention or reader acquisition strategies.
But where I’ve probably use this stuff the most is with building unique, specific tools to automate or organize some of my non-writing work. We’re a small company with limited financial resources, and I need all the manpower and executive function I can get to keep everything else functioning, so I can focus on writing and reporting.
So sure, I’ve hacked together simple tools to help keep track of my email inbox, file and track FOIAs in bulk, extract financial information from PDFs, and automate business stuff. I had a lot of fun at ONA26, chatting with other reporters about hacking together tools to do everything from track high school sports statistics to graph government appropriations to make booking hotels faster.
Schools can do this sort of thing too
The following is a sponsored segment by SherpaSports:
Last week, DJ Johnson, a former athlete-turned-entrepreneur, told me that one of the biggest challenges he sees in college sports administration is figuring out how to get all the myraid tools departments use to collect data to actually talk to each other. And that’s hard, because every school has very different needs, but often buys software off the shelf.
This is the problem he’s trying to solve with SherpaSports, an AI-driven tool meant to help “bring Silicon Valley into college sports.” Sherpa allows schools to bring their own data, on everything from athlete contracts to weight room numbers to social media activity and build dashboards and interactive tools specific to each athletic department.
“We don’t want to come in and uplug everything schools already have,” Johnson told me. “But sit on top of it or run alongside it.” The goal is to essentially help athletic departments build program-specific tools, just like I’ve done with my newsletter business, to help them streamline recruiting, evaluation, ticket sales, and more.
In practice, that might mean building dashboards to integrate athlete performance data with social media platforms, so brands (and NIL departments) can better identify potential sponsorship opportunities. It could also mean building tools to help in-house sales teams build better target lists for athlete and schol sponsorship opporunities. It might mean combining compensation data with athlete training information, to more efficiently deploy team resources. Or it could mean finding easier ways for the marketing folks to talk to the front office types, and for everybody to make sure they’re on the right side of compliance.
To learn more about how SherpaSports can fit into your athletic department needs, click here.
You have to be willing to change
Earlier in my career, I didn’t have to worry too much about anything other than writing. How that writing found an audience, or made money, or any of that other stuff, was mostly someone else’s problem.
Obviously, that’s not the case anymore. But many of the strategies that worked a lot for newsletter businesses in 2022 don’t work in 2026. I, like all of my peers, have to constantly look for new strategies not just to produce good work, but also to help people find it and convince somebody to pay for it.
Software wasn’t on my radar in 2022. Now, it’s a vitally important part of our business. Twitter used to be the biggest audience discovery source AND a better network than LinkedIn to find our next job. That…is not the case anymore.
The college sports industry is the same way. If you’re selling your tickets the same way in 2026 that you did in 2021, you’re probably doing it wrong. You certainly aren’t recruiting players the same way you did five years ago. You’re not approaching revenue generation the same way you did five years ago. You’re probably not thinking about capital projects, government affairs, travel logistics, or anything else the same way either.
It’s easy to get despondent about many of those changes, especially the ones that you can’t control. But boy, it sure was nice to spend a few days around so many people who are very much struggling with those same changes but approach them with energy and, if not optimism, at least resolve.
I’ve got a few more ideas on how to make better work, produce work that’s sustainable, and make sure that EP lives out the professional values that I think are important. As “crossover season” wraps up and more folks in this business find a second to exhale for the first time since February, I hope they can do the same.
The problems aren’t easy. But they are solvable. But they can't be solved just by complaining…no. matter how good and righteous that can feel sometimes.
