Monday Morning Check-In: Everything’s More Interesting With Money On The Line

Reading Time: 9 minutes.

I’ve gone through several distinct phases of how I approach a March Madness bracket, and none of them have involved actually knowing college basketball.

About a decade ago, I was the guy joining office pools thinking, “This is it. This is how everyone finally realizes I’m secretly a basketball genius.” This was a bold strategy considering I don’t really follow college basketball… at all. I’d try to watch games and just burn out. Also I’ve never had a strong local team to latch onto in college basketball, and keeping up with it feels like trying to follow a TV show where the entire cast gets replaced every season. Unless you’re rooting for one of those perennial powerhouse schools, it’s basically: “Meet this year’s completely new group of teenagers!”

So naturally, my strategy evolved.

I shifted from “prove I’m smart” to “maybe accidentally make money.” I’ve never been a full-on gambling degenerate, but I do get the appeal. Sports are objectively more interesting when you have even five dollars riding on whether some 19-year-old hits a free throw.

I haven’t done a March Madness bracket in a couple of years, but I did join fantasy football this year as the NFL is something I actually pay quite a bit of attention to. That went great—if your definition of “great” is being mathematically eliminated by midseason and continuing to check your lineup out of pure spite. Seriously like my top 2 picks were out for the season by week 2.

One thing I genuinely love about March Madness, though, is how gloriously random it is. Every year, there’s someone in the office pool who picks winners based on mascot vibes or jersey colors—“I just like bulldogs”—and they end up crushing everyone. Meanwhile, the guy who’s been watching tape since November is sitting there like, “Well, statistically—” and then immediately loses to a 13-seed.

It’s chaos. Beautiful, democratic chaos.

And that’s probably why I’ve never been into casinos. I don’t enjoy games where I know the house is going to win most of the time. Slot machines feel like donating money with extra steps. Blackjack is just a series of coin flips where the dealer somehow always has a 6 showing and still ends up with 21. It’s suspicious.

Poker, though—I kind of get. I’ll play on my phone with fake money and feel like a genius compared to the other goofs playing on there. Then I play in real life and suddenly turn into the most cautious human alive. I fold everything. I become a monk. And then, halfway through, I realize I’ve been playing like I’m protecting a retirement fund, panic, go all-in on something dumb, and I’m out five minutes later.

So yeah, I’m not exactly headed to the World Series of Poker anytime soon.

These days, I mostly stick to small office pools or casual online bets—just enough to make games interesting without needing to explain to my family why I’m eating ramen for a month.

Because here’s the thing: a lot of people don’t understand why anyone would sit and watch random sports games for hours. And honestly, if you don’t have a rooting interest, they’re right—it can be pretty dull.

But that’s where stakes come in.

Sometimes it’s emotional—like rooting against your rivals. As a fan, there’s nothing quite like watching your team win… except maybe watching your rival lose. That’s a special kind of joy. Petty? Sure. But also essential. In my case watching Wisconsin and Iowa teams in any sport lose is just great. When it comes to the NFL, watching the Packers and Vikings lose is better than the actual super bowl.

Other times, it’s just a little money. Not a lot—just enough to make you suddenly care deeply about a game you didn’t know existed an hour ago.

And that’s the secret fuel behind a lot of sports obsession: it’s not always about the love of the game.

Sometimes it’s about having just enough on the line to yell at your TV like it personally wronged you.

I’ve been hearing that the Minnesota Golden Gophers women’s basketball team is having a strong year, which is great to see. Minnesota just seems to have strong women’s sports teams across the board. It brings up a conversation I’ve noticed more online lately—why women’s basketball doesn’t get the same level of attention as the men’s game, both in college and at the professional level.

There are a lot of perspectives on that. Some people point to media coverage, marketing, and long-standing habits in how sports are promoted and consumed. Others raise a different angle: that fan engagement plays a role too, and that growing the audience for women’s sports isn’t something that can fall on just one group.

It’s probably more accurate to say it’s a mix of factors. Visibility, storytelling, media investment, and fan interest all feed into each other. More coverage can drive more interest, but interest also signals to networks and sponsors what people want to watch.

So instead of framing it as one gender’s responsibility or the other’s, as many seem to be doing, it might make more sense to look at it as a shared opportunity. When teams are competitive and compelling—as the Gophers seem to be this year—that’s a great moment for fans, media, and leagues alike to lean in and help build momentum.

At the end of the day, attention tends to follow excitement, familiarity, and access. The more those things grow, the more the audience usually does too.

I’ve been watching

Grey’s Anatomy. That’s right, I’m 22 seasons and around 25 years behind on that. I was busy watching House M.D. back then and couldn’t see any of those other medical shows being nearly as good as it so I never gave them a chance. But The Pitt has me wanting more medical drama so I thought I’d go back and watch the one that’s been massively popular for over 2 decades. I see the appeal, on episode 4 and I’m definitely into it. I like pretty much all the side characters. Meredith hasn’t really won me over yet.

I’ve been cooking

Corned beef & cabbage! Happy St Patricks Day, by the way. Oh, right, everyone’s moved on to Easter. And I just learned this year that Corned Beef & Cabbage isn’t really much of an Irish thing, more of an Irish-American thing. Oh well, I still love it, and wish it was something we made weekly! I guess I can just get a Reuben somewhere for my fix, though.

Boiled bacon (salted pork) + cabbage + potatoes is the more traditional Irish dish, which sounds just fine as well. I do like to make a cabbage soup that’s basically exactly that. Cabbage is so underrated, I just love it.

I’m preparing for

a trip to Florida that’s a bit different than my usual. No this is not one of my “sit in a chair, stare at a lake, occasionally burn a hot dog” kind of camping trips.

For the past few years, I’ve done a solid weeklong July campout on a lake with a beach, so I’ve been easing into the whole beach-adjacent, aquatic-vacation lifestyle. You know—dabbling. Splashing with intent. Owning at least one towel that isn’t from 2007.

But this upcoming Scouting high adventure in the Florida Keys at SeaBase? Whole different beast. This isn’t “relax near water.” This is “become one with water or perish (politely, under supervision).”

I’ve had to buy gear I never thought I’d need—things that make me look like I’m either going snorkeling or auditioning for a low-budget reboot of Baywatch: Midwest Edition. I’ve also been doing swim safety training, because Scouts are involved and apparently “vibes-based swimming” is frowned upon in leadership roles.

And then there’s the swim test.

Since I started actually swimming—like, on purpose—I’ve discovered my neck is apparently made of rebar and unresolved stress. Turning to breathe feels less like a natural motion and more like I’m trying to rotate a rusted bolt. Every time I attempt it, my body just panics and goes, “Nope, we’re doing a full side stroke now.”

The problem? I don’t actually know how to properly do a side stroke. It’s like my brain understands the concept, but my body is buffering. My swim instructors call what I end up doing “shark kicks,” which sounds cool until you realize it just means “flailing aggressively while hoping for forward progress.” I just can’t get that scissor kick down in timing with whatever it is I’m supposed to be doing with my hands.

I’ve been trying to practice a real side stroke, but it feels like learning choreography from a dance I’ve never seen. Arms go here, legs go there, breathe at some point, don’t drown—it’s a lot. Honestly, it’s like trying to walk and chew gum at the same time… if I were a one-year-old… underwater… with mild existential dread.

So yeah—here’s hoping this Florida adventure goes well, I pass the swim test which they apparently throw us into as soon as we arrive, but hopefully this all turns out to be one of those situations where I was wildly overthinking everything. Nothing wrong with overpreparing I guess.

Worst case scenario, I invent a new stroke: The Anxious Shark. I think it has potential. As long as I actually survive it.

I’ve been listening to

The Pretty Reckless. I think a lot of folks in the rock scene think they’re a manufactured, phony band. I feel like they’re pretty legit and if that were the case they wouldn’t have stuck with it for this long. They have a new album coming out this summer that I’m looking forward to. The couple of singles that have already arrived are sounding really good. Check out my profile on Last.fm for more on what I’m listening to and follow me there if you have a profile.

Our weather

Has been wild. It got up to 72 here on Saturday. That 12 inches of snow last week? Mostly gone. We’re looking at 40s and 50s this week which now feels cold again thanks to that tease.

Quote of the week

“Truth is strong, and sometime or other will prevail.” –Mary Astell

Don’t forget to follow me, you guys


Check out my recent posts

By Dustin