Gambling It All Away

Lessons in betting, the glory days of poker, the mad world of online sports wagers

Each week, a menu of sorts, around a revolving theme. After a week off because of work travel and events around the Chicago Marathon (including me running it), we’re back. This week: wagering it all, or at least some of it.

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Ingredient List

A list of things I enjoyed this week.

📖 : “The Hustlers Who Make $6,000 a Month by Gaming Citi Bikes,” New York Times (gift link) // I love a great side hustle or a good loophole exploitation (as you may remember from my past newsletter, “Never Let a Good Side Hustle Go to Waste”, and this is a great one.

“As America’s Marijuana Use Grows, So Do the Harms,” New York Times (gift link) // This is an incredibly well done and in-depth piece on the state of marijuana today, especially in high THC varieties and its effects on teens and young adults and those with cannabis use disorder. Everything has a trade-off, folks.

“Sports gambling takes a toll on Americans' checkbooks, research shows” by NBC News // I reference this article in the main course of this week’s email, but it’s one of the first research studies showing the large scale financial effects on households in states that have legalized sports betting. It’s not good.

🎧 : “The Mystery of the Vape Shop Kratom,” Search Engine // Another great episode from one of my favorite podcasts, this one investigates the mysterious opiate-like effects of “gas station heroin.”

“An Interview with Kilian Jornet, the Greatest Ultrarunner of All Time” The Drop // I had the incredible opportunity to interview Kilian Jornet for our podcast at Believe in the Run. In addition to winning almost every major ultrarunning race in the world, he’s also the fastest man to summit Mt. Everest without oxygen, among many other records. It was a great conversation.

And now, onto dinner service.

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Course 1

A Word of Gratitude: Well Done Table Stakes

There was a certain in-between time in my life when I first moved to Baltimore, after I had left the band, but was still trying to figure out how to survive. My life plan was operating on a month-by-month basis, but I was trying to extend that timeline a bit further, grasping for a bit of ground beneath my feet.

That past summer I worked for my brother-in-law, cleaning and detailing boats around Annapolis and Baltimore. For me, it seemed like a viable career option, so I made plans to buy the business from him and operate it on my own. To do this, I needed some capital for start-up supplies, mainly to outfit myself and my partner with two Makita power buffers, cleaning and detailing supplies, and uniforms. Stubborn and self reliant, I figured I could do most of this myself over the winter by working barback shifts at a Slainte Irish pub in Fells Point.

Over the course of a few months, I managed to save up nearly $2500 in cash, which was kind of a lot for a lowly industry worker. Towards the end of winter, right before the season began, there was a boat industry trade show in Atlantic City, so I figured we should go to make some connections or at least see what was new.

Of course, when you’re in Atlantic City, there’s only one thing to do: spend money.

Eventually, we found ourselves at the blackjack tables, the only form of gambling I approve of when inside of a casino, because at least you have a chance. You do until you don’t.

The limits were low, maybe $10, which is impossible to find anymore. Things were going fine, I was up a little bit, but then the table got cold. Suddenly I was skinny dipping in Siberia. To this day, it is still the coldest run of cards I’ve ever experienced. The dealer was winning on everything and I was busting hands at the same rate. Eventually I lost $200, which was my limit going in. You may be thinking: “Two hundred dollars, that’s it?” Reminder, I had nothing to my name at the time, except for that small business bankroll I had set up. So $200 was a lot, and while I told myself it was what I was willing to lose, the truth is, I couldn’t afford to lose it.

Fueled by a few beers and a strong “feeling” I could win it all back– that eventually my luck had to turn– I made a beeline for the nearest ATM and pulled out another $100. I went back to the table, pushed my cash to the middle and got my chips from the dealer.

I never lost $100 faster in my whole life.

I sat there, stunned, frustrated, angry that it was all gone. That $300 was the cost of a new Makita power buffer, and I really needed that money, which was almost an entire week of pay at the time. Simply put, I couldn’t afford to lose it. I needed it back and was ready to go back to the ATM. Luckily, my friend and partner Andy was there to pull me back from the edge and reason with me. So I left the casino, and Atlantic City, dejected and depressed and wishing I’d never come.

I can’t tell you how much I hated that feeling. It was such a deep pit in my stomach that lingered for a long time after. To this day, it was one of the worst feelings of my life. 

In hindsight, I’m grateful it happened, because it was a hard lesson I needed to learn that would serve me well throughout my life. I’ve had plenty of opportunities to throw away money since then, whether through meme stocks, crypto boom and busts, online gambling, or other trips to the casino. I’ve won some and lost some along the way, but it’s never been stressful. Now, I only play with what I’m willing to lose, and I’ve never had that pit in my stomach again.

And for that, I am grateful.

Course 2

Appetizer: Lined Up Lemons

Earlier this summer, I took my 8-year-old on a work trip to Lake Tahoe for the Broken Arrow trail running festival. I’ll skip the details of the trip since he was sick with a horrible cough, we were both dealing with altitude and jet leg, there was little for kids in the way of activities, and at some point I may have used my phone-a-friend lifeline to my wife to bring me back to earth. It sounded like a great idea at the time, but it wasn’t.

We made it through and made it back. On our way back home, we had a layover in the Las Vegas airport. If you’ve never been to Harry Reid International, it’s mostly just like any airport except it’s a lower circle of hell.

As a major transfer point to cities in the Southwest, it’s busy. But it somehow manages to take an already crowded situation and put it in a pressure cooker. Mainly because every square inch of extra space is filled in with either a slot machine or a smoker’s lounge. Mini casinos abound around every corner, every corridor, and in every terminal. The one-armed bandits meeting you in broad daylight for a showdown at the OK Corral: Hey, I see you waiting there, why don’t you just give me a couple spins? Do ya feel lucky, punk? Do ya?

Of course I felt lucky, because, well– you never know, right?

Our flight was delayed by a couple of hours, as if by design, so while sitting across from a little pow-wow of slot machines, I figured it’d be a good time to teach my son a lesson.

“See those things? People try to win money from them, but they never do. Don’t ever play them because they’re just for suckers. They think they’ll win, and it seems like a fun game, but really the casino takes all their money. It’s a scam.”

It’s one thing to tell a kid that, but to get the full effect of the lesson embedded as a core memory, I figured it’d be better to show him. 

Here’s the other thing about the Vegas airport– they cover the whole thing in a rash of gambling; extend a tape measure twenty feet in any direction and you’re bound to hit a slot machine. We were literally sitting at our gate, 10 feet from a slot machine, my 8-year-old watching people play. But if he steps foot into that area, which everyone is crowded around because there’s no space in the airport thanks to slot machines– a security attendant will immediately come over and order us to move, because no kids are allowed within the slot machine zone. Make it make sense.

I didn’t know this rule at first, and I must have caught the attendant sleeping, because I took Rye to the slot machine with me, to give him a real life lesson in loss.

“Here, watch how fast I lose this five dollars,” I said to him as he stood beside my chair. “This right here– this is why you shouldn’t ever gamble.”

I hit the button, betting $1 each time so I could advance the losses even more quickly. Loser. Loser. Loser. Winner (back up to $5). Loser. Loser.

Winner and– bonus match. 

Everyone wants the bonus match because it means you can level up the whole way to the main jackpot. On this game, there were five jackpot levels of varying degrees. And they’re very fun to play, so many colors and sounds and animations. They really do keep the customer engaged and entertained. When the bonus round was all said and done, we ended up winning the lowest jackpot of $10, putting us up to $13 on the machine, a 130% return on our investment.

Time to shift lesson plans. 

“Okay, so sometimes you can win at gambling, and if that’s the case, then it’s important to get out while you’re ahead.” So I hit the cash out button and took our winnings.

From there, we went to the gift shop where I bought some snacks and he bought… a miniature toy slot machine, which he spun the whole way home.

And that’s why you don’t teach lessons.

Course 3

The Main: Drugs, Alcohol, Chocolate, Crypto

When I was in eighth grade, my friend CK was already on a path to a lifetime of gambling. In study hall we’d throw dice against a wall for quarters, during baseball season he’d bring in the newspaper to analyze matchups and force me to bet on that evening’s games. I don’t think I had yet grasped the concept of odds; most likely I was placing bets on team colors or favorite players. I doubt I won money and I still don’t know where the house money came from. Maybe it was from his basement, where his dad had a dozen water cooler jugs filled to the brim with quarters, ten thousand dollars of change just casually mixed in with winter clothing storage.

My college years coincided with the peak of Texas Hold’em madness, that odd time in history when old men who spent their whole lives in smoky Vegas card rooms were somehow suddenly household names– Doyle Brunson, Amarillo Slim (whose autobiography is still one of my most favorite books ever), Daniel Negreanu, and Phil Hellmuth. Spawned by the movie Rounders and cultivated by ESPN’s coverage of the World Series of Poker, we couldn’t get enough of it. When an average guy named Chris Moneymaker (of course that’s his name) worked his way up the ladder of qualifying tournaments and won the 2003 version of the main event, he was all of us. We too could live that life, if we just ignored all our college responsibilities and went all in on poker. 

At that time, I was basically broke, surviving on whatever modest income I made by working the doors at a local funeral home; before the viewings I’d vacuum dropped flower petals around the casket, just me and a corpse spending its final moments above ground together. When I took that income and played poker with friends, it wasn’t on credit, it was real cash in my real hands that meant something if I lost it. It was a terrible spot to be in, because playing scared means you’re playing to lose, unable to bluff and bully when necessary. So while poker consumed a good amount of our free time, it was really never a stressful situation.

On the rare occasion we did want to gamble at an actual establishment, we’d either have to drive to the dog track in West Virginia (of which I’m happy to say only happened once) or to the Canadian side of Niagara Falls, where both gambling and drinking were legal for college students. Since we were only a few hours away from the great north, these could be impromptu trips; on one occasion, we left Beaver Falls at midnight and arrived at the slightly more majestic Falls at around 4 a.m. By dawn, my friend Kurt had pulled in $1,000 on the blackjack table, an amount of money that was truly staggering at the time, as if we had somehow pulled off a legal version of an Ocean’s Eleven heist.

On the flip side, we’d drive to Atlantic City over holiday breaks, a place that is the portrait of American misery, whose only real redeeming value is its contribution of street names on a Monopoly board and the inspiration behind Boardwalk Empire, arguably Steve Buscemi’s best performance outside the lipstick-wearing former classmate of Billy Madison. While I’d usually piggyback onto a comped hotel room via my friends’ rewards, I still wanted to leave within hours of arriving. Sadness abounds, especially in the dead of winter. One January, a friend of ours lost a large sum on the poker tables at the Taj Mahal; afterwards he walked into the ocean with all his clothes on. 

He was just one of my friends who ended up walking down the decrepit boardwalk paved by online gambling, which really began with online poker. Sure, gambling has always been there: State-sponsored lotteries, otherwise known as a luxury tax on the poor and uneducated, have been a stable stream of government income for decades. But nothing opened the floodgates like the world of online gambling. 

At first , it was a trickle. During the height of early aughts poker boom, sites like Pokerstars or UltimateBet blossomed, hosted on international servers to escape regulation which took nearly a decade to catch up. The user experience was pretty incredible for the time, so it was easy to get drawn in. I, like many of my friends, spent way too much time on those sites, convinced I could eke out a living or a side hustle if I just honed my skills. In the end, I never lost a lot of money, mostly seesawing between going up a few hundred and back down to even. Nevertheless, it was a colossal waste of time, hours of late nights spent playing $5 poker tournaments, getting nothing but little sleep in return. 

On the other hand, some friends ended up becoming professional poker players, while others languished as wannabe versions of ones. The successful ones were pulling all-day shifts with eight games going on at a time, pulling in hundreds of thousand dollars a year. One of them, a close friend from high school, eventually became an alcoholic and lost his family. The friend who walked into the ocean after losing his bankroll at the Taj Mahal? He played online for years afterward and eventually lost his entire life’s savings before admitting it to his wife and finally going to Gamblers Anonymous. 

I suspect that addiction hotlines and gambling recovery groups will see record numbers in the coming years. Because the rise of online gambling, spurred by sports betting, has been unprecedented and will only continue going up and to the right. 

Though the overall economy took a hit during the Covid years, the addiction economy saw massive gains– drugs, alcohol, chocolate, crypto, and especially gambling. From 2019 to 2023, sports betting in the United States alone went from 400 million dollars in gross revenue to over 11 billion dollars, a 2,600% increase. On the player side, in 2023, bettors placed almost $120 billion in bets in the U.S. alone, more than the entire GDP of the Dominican Republic. The explosion in growth coincides with the Supreme Court striking down a federal ban of sports betting in 2018, concluding that it violated states’ rights. Thirty-eight states and the District of Columbia now allow gambling on games.

If you have eyes and breathe, congratulations– you’re alive. It also means you’ve been subjected to the deluge of sports betting ads over the last several years; in fact, you’ll probably get even more of them now that you’re reading this. It’s nearly impossible to go a single commercial break during football season without getting a pitch for DraftKings or FanDuel or BetMGM. Even when you play your free CBS Sports March Madness bracket once a year, you’re still getting hammered with ads to try the betting version of it.

Celebrities and athletes have zero qualms about hawking a buffet of betting platforms, sweetening the pot by luring prospective bettors in with free sign-up bonuses. A friend of mine got caught on one of those, thinking he would get back his cash deposit if he lost his initial deposit, not realizing they just repay you in gambling credits. He went into a downward spiral of trying to win his money back, keeping it a secret until it was no longer a secret.

To be completely open, I’m not averse to gambling on a personal level– it’s the only way to get me to care about football at this point, so I usually link up with friends for very small stakes– $20 fantasy football or a $50 run through the playoffs, $10 squares for the Super Bowl. March Madness remains the greatest sporting event on the planet, and it’s worth spreading around a few $10 bracket buy-ins to juice up the excitement levels even more. And while I’ll go into a casino once a year when I visit CK down in Fort Lauderdale, I fully expect to lose the $200 I enter with.

For whatever reason, I’m hard-wired to take calculated risks, and for that I am lucky. I feel the pull of gambling, but I can just ignore it. I’m able to think rationally about it and know that safe, long term investing always pans out better than risky short term successes. For others, it’s not so easy. And as much as Vegas and FanDuel would like you to think it’s all glitz and glamor and bright lights and happy times, the reality is that it’s often broken families, empty bank accounts, and relentless dodging of debt collectors. 

A stunning report was published just two months ago, one of the first to look into the effect of sports betting in America. The researchers “found that legalization has led to higher credit card balances, lower access to credit, a reduction in longer-term and higher-yield investments … with the effects particularly pronounced among financially constrained households.” In states that legalized gambling, credit scores dropped a significant amount, bankruptcies increased 28% and debt transferred to debt collectors climbed 8%. Auto loan delinquencies and use of debt consolidation loans also increased. The saddest part is that the bettors were more likely to have children.

Of course, the coffers of the states are flush with cash. New York state has a 51% tax on sports wagering and pulled in over $2 billion the last three years alone. If it’s not clear to you yet, let me reiterate: sports betting, and gambling in general, is a tax on the poor. And if you think the states are reversing that any time soon, then I have a bridge to sell you in Manhattan; if gambling is your thing, we can flip a two-headed coin for it. 

It’s only going to get worse. As AI learns odds and calculates them faster and faster, in-game betting will become highly refined. Any game, any sport, any second of the day. Parlays of pitch speeds, ball rotation, crowd decibels, whatever you can perceive with your eyes and that what you can’t– it’s all on the table. All of this, of course, will be in the palm of your hand. Which is why mobile sports betting is essentially vaping for gamblers. The most addictive part of vaping isn’t the nicotine, it’s because it can go with you everywhere. It’s the same with betting, and especially sports betting. What was once a hurdle– driving to Niagara Falls or Atlantic City, finding a hidden poker room or rounding up friends for a game, calling a bookie on the phone to place bets– is now a guided tour inside of your own living room. As with vaping, the addictive substance is in your hand, at any time of the day. 

This newsletter is going out on a Sunday night. It’s very likely that some of you reading this have lost (or even won) a parlay earlier today. If not, you’ve seen this at a Super Bowl party or a family gathering for college football– the friend who is personally offended that the kicker for the Browns missed a field goal in the second quarter, or the brother-in-law enraged at Patrick Mahomes for downing the ball four times to end the game, pushing his rushing total into the under when they had taken the over. The oversized and outsized reaction to a play that just a decade ago would’ve gone unnoticed.

The toxicity is even more pronounced and awful on social media. Go check out an athlete’s account after a dropped pass in the end zone or a poor performance on game day. It’s appalling. Running back David Montgomery recently revealed how he contemplated suicide in his rookie year from all the hate and death threats received by fantasy football managers. (He was on my fantasy football team that year, and I thought he performed quite well for me.)

All of this is hurtling towards an awful end. I don’t know where that is or when it will happen. But it doesn’t sit well with me that, as a society, we have wholeheartedly embraced the legalization of online sports betting as if it’s a good thing, a true freedom to do what we want whenever we want. As with any addictive substance, freedom to use often leads to abuse. Statistics tell the truth– it is doing far more harm than good. 

Allowing unfettered access, combined with the endless promotion of it, will ruin families and relationships and retirements the same way gambling always has. Except, instead of it happening in a smoky riverboat casino, we’ve given the green light to turn our living rooms into card rooms, bedrooms into Vegas book bars, and the sideline of our kids’ soccer games into the betting line of a football game. All while funneling money to mega-rich corporations and state governments up to their necks in lobbyist influence.

Those are stakes that no dorm room poker tournament can ever compete with.

Course 4

Dessert: A Repast of the Past Week

Again, apologies for skipping a week, but we’re in the thick of fall marathon season which means that my work and life schedule is an absolute roller coaster. I also like writing under pressure and what’s relevant to me in the moment, so I never have any back-ups waiting in reserve. That’s just how it goes over here.

Two weeks after running the Berlin Marathon, I turned it around and ran the Chicago Marathon. It was an “interesting” time, but I finished the race. Leading up to the race, we invited our podcast listeners to run a sub 4-hour marathon with me, and 70 people signed up to do it. We hooked them up with custom singlets from New Balance, free race photos, some Robbe Raccoon stickers, and more. Most of all, we all got to be a part of a special community for one of the best marathons in the world.

It was also my wife’s birthday this week, so happy birthday to her. We celebrated by having some friends over for an afternoon of pickleball and an evening of karaoke at the always incredible and forever iconic Walt’s Inn here in Baltimore. First impressions of karaoke at the age of 42: you know you’re old when most of the songs are from the early 2000s. Way too much Eminem and Linkin Park and the greatest sin of all– the crowd looked lost during Kimi’s rendition of Gangsta’s Paradise. How are they so blind to see that the ones they hurt are you and me?

Other things I’ve written or edited this past week:

• Adidas Adizero Evo SL Review: Simple Bliss

I also contribute to The Drop, a weekly email from Believe in the Run, where I round up running news and stories in a generally sarcastic (and sometimes heartfelt) manner. You can subscribe here.

I’m also the co-host of The Drop running podcast, one of the top running podcasts in the country, where we mostly talk about things other than running that thousands of people seem to find entertaining. You can listen to this past week’s episode here, where we give a full recap of the Chicago Marathon weekend.

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Thank you for dining with me this evening, I hope the service was acceptable. Tips (whether monetary or recommendations to others) are appreciated, but not expected.

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