
There are some very interesting loopholes in the world of marketing.Because businesses are always looking for an upper hand in a competitive category, loopholes can offer legal advantages.A loophole…
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Did you know that if you subscribe to our But Wait, There's More option, you get a bonus story in every episode of under the Influence. But wait, there's more. For the price of a cup of coffee every month, you get early access so you hear every episode a full week before everybody else. Plus you enjoy that episode ad free. Tsk tsk. And by subscribing you support our podcast. Just go to Apple Podcasts and subscribe to under the Influences. But wait, there's More. Did I talk too much? Can't I just let it go?
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You're under the influence with Terry O'Reilly.
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Roger Nielsen coached hockey for over 50 years. At one time or another, he was head coach of 10 different NHL teams. He was also one of the most innovative strategists in hockey history. Nielsen was the first to analyze video to pick apart opponents weaknesses. He was the first coach to insist his players follow a fitness regime during the off season. But more than anything, Roger Nielsen would pore over the rule book constantly. And he had a knack for spotting loopholes. Before he broke into the NHL, Nielsen coached the Peterborough Petes in the ohl. And it was there he spotted a loophole when it came to penalty shots. Nowhere in the rule book did it say that a goaltender had to be on the ice during a penalty shot. So whenever a penalty shot was awarded to the other team, Nielsen would pull his goaltender and put a defenseman out there instead. His reasoning was that a defenseman could rush the shooter and check him one on one instead of letting the opponent enjoy a breakaway against the goalie. His strategy worked. Every penalty shot against the peets was thwarted by his defenseman. But the OHL finally put an end to that tactic and instigated a new rule stating a goalie must be in net for penalty shots. The NHL adopted the same rule shortly after. Whenever his team had two men in the penalty box in the last few minutes of a game, Roger Nielsen figured out a way to overcome a 5 on 3 disadvantage. He leveraged an existing rule that stated a team can never have less than three men on the ice at any given time. Knowing that he would intentionally put too many men on the ice every 10 seconds, he would inevitably get a penalty each time. But he knew that no matter how many penalties he got, his team would always have at least three men on the ice. But by disrupting the play every 10 seconds, he would kill the other team's momentum and run the clock out. So the OHL wrote a new rule. Intentionally putting too many men on the ice in the last two minutes of a game would result in a penalty shot. The NHL adopted the same rule shortly after Nielsen exploited another loophole. In the final minutes of a losing game. When the face off was in the opposite end and he pulled his goaltender to put an extra attacker on the ice, Nielsen would tell his goalie to leave his stick directly in front of the net. That way, if a puck was shot from the other end, it would bounce off the stick, preventing a goal. There was no rule against it. The OHL put an end to that nifty trick pretty quickly, making the practice illegal. The NHL enacted the same rule not long after. All of those changes had a big effect on hockey. Roger Nielsen, the innovator, didn't break the rules. He just had a talent for spotting loopholes. There are some very interesting loopholes in the world of marketing, too. Businesses are always looking for an upper hand in a competitive category, and loopholes sometimes offer legal advantages. A loophole can help a company overcome barriers in the marketplace. Sometimes the way a product is marketed can give customers a loophole they can take advantage of. And as we'll see today, sometimes a 20 year old kid can spot a loophole that panics a giant corporation.
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You're under the influence.
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Back in 1953, the owner of the St. Louis Cardinals had a problem. He was about to serve a 15 month jail term for tax evasion and was forced to sell the baseball team. Not long after, he accepted a bid from anheuser Busch for $3.7 million. Sportsman's park, where the Cardinals played, was shared with another baseball team called the St. Louis Browns, who actually owned the stadium. But the Browns organization couldn't afford upkeep on the aging building, so it sold Sportsman's park to Anheuser Busch. The Browns then moved to Baltimore, where they became the Orioles, and the Cardinals now had the ballpark all to themselves. With all that settled, Anheuser Busch changed the name from Sportsman's park to Budweiser Stadium after its biggest selling beer. But the commissioner of Major League Baseball vetoed that decision, saying a ballpark could not be named after an alcohol product. That's when the brewery took advantage of a loophole. Anheuser Busch changed the name of the ballpark to Busch Stadium not long after, the brewery launched Busch. Thus, instead of naming a ballpark after a beer, they named a beer after a ballpark. A few years ago, I toured the famous Motown Studios in Detroit. While on that tour, our guide told us a story of how founder Barry Gordy Jr. Used a loophole to Kickstart his legendary R and B record company. Before Motown was Motown, Gordy started Tamla Records in 1959. Named after the Debbie Reynolds song Tammy, the first hit Tamla had was titled Money that's what I Want by Barrett Strong. One year later, the label had its first million seller, courtesy of Smokey Robinson and the Miracles called shop around. In 1961, the label landed its first number one record, Please Mr. Postman by the Marvelettes. Then the hits just kept on coming and coming. And that created a big problem. Radio stations in the early 60s shied away from playing too many records from one label. It invited accusations of favoritism and worse, payola, where record labels paid radio stations to play their songs, an illegal practice that prompted a congressional investigation. With all the new songs rolling out of Tamla Records, Berry Gordy was having a difficult time getting them played on commercial radio. He needed hits to generate revenue. So he took advantage of a loophole. He created multiple labels. The original was Tamla, Then came Motown Records, then Miracle Records, then Gordy Records, then Melody Records, Divinity Records, VIP Records, Soul Records, and a dozen more. Each label had its own distinctive style and color scheme. That loophole eliminated the problem of reduced airplay and got Motown songs played on thousands of radio stations. From 1961-71, Motown had 110 records in the Billboard Top 10. An incredible achievement for a small record label. Or should I say labels. Speaking of music, the Michigan based funk band Vulpec wanted to go out on tour. And they wanted the admission to be free. Except they had one problem. They didn't have enough money to mount a tour. Over the years, Vulpec had released half a dozen albums on Spotify, but the revenue was minimal. For every song played on Spotify, the band only received about half a cent. At that rate, it would take a long time to generate enough money to stage a free tour. That's when the band came up with an idea. In March of 2014, Vulpek decided to put out a new album on Spotify. They titled it Sleepify. It was a very quiet album. The reason? All ten tracks were silent. Completely silent. Then Vulpek released a video on YouTube explaining their idea.
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I'm proposing that if you stream Sleepify.
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On repeat while you sleep every night, we will be able to tour without charging admission. So if you streamed the Vulpek album on repeat while you slept all night, you would generate a grand total of $4. But if enough people streamed Sleepify on repeat all night every night, the royalties would add up. As the band pointed out, never in the history of music has it been so easy to support a band's tour. All you need to do is is make your sleep productive. Each track on sleepify was just 31 seconds long for a reason. Spotify requires a song to be played for at least 30 seconds to be registered as a play. It only took five minutes to stream all 10 tracks. If a fan slept for, say, seven hours and streamed the album all night, they'd generate $5.88 for Vulpek. If 100 fans did that, it would generate $588 for Vulpeck per night. And if thousands of fans streamed the album on repeat every night, it could add up. After 10 days, Sleepify had racked up 1 million plays. Seven weeks later, the album had 5.5 million, which translated to over $20,000 in royalties. That's when Spotify removed the album from its site. Spotify sent Vulpeck an email saying while they thought Sleepify was clever and funny, it violated their terms of content. In response, Vulpek posted a new album to Spotify. The title was Official Statement. The first track was titled Hurt. It was a spoken word performance where the band read Spotify's email and said it was hurt their Sleepify album had been removed. The second track was titled Reflect, where the band said they wanted to take 31 seconds to reflect on the situation, which was followed by 31 seconds of silence. Too funny because Spotify said Sleepify violated its terms. The band was unsure if they would receive any royalties. But Spotify did come through and sent Volpek a check for $20,000. The loophole had paid off. Which reminds me of the time a retired couple figured out a loophole in in a lottery. Dude, did you order the new iPhone 17 Pro? Got it from Verizon, the best 5G network in America. I never looked so good. You look the same. But with this camera everything looks better. Especially me. You haven't changed your hair in 15 years. Selfies check please.
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Did I talk too much? Did I just let it go?
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Jerry and Marge Selby lived in a small town in Michigan. They ran a convenience store for 17 years, then retired. One day in 2003, Jerry walked into the store they used to own and noticed a marketing brochure for a new state lottery called Windfall. He read it and in less than three minutes, he spotted a loophole. Unlike other lotteries that keep building until there is a winner, once the windfall jackpot reached $5 million and no one had matched all six numbers to win, a roll down would happen. That meant the money rolled down and was split between winners who matched just five, four or three numbers. Jerry quickly calculated that if he spent $1,100 on 1100 tickets, odds are he'd have one four number winner that would pay out $1,000 and at least 18 or 19 three number winners that paid $900. That meant his $1,100 investment would yield a $1,900 return for a tidy profit of $800. 64 year old Jerry Selby had a bachelor's degree in math and he loved solving puzzles. But because the loophole logic was based on rudimentary arithmetic, he feared a lot of other people would figure it out too. But for the longest time, no one did. So Jerry decided to test his theory. When a roll down was announced, he purchased $3600 in windfall tickets. Sorting through 3600 tickets took hours, but he made a $2700 profit that confirmed his math. Next, he purchased $8000 worth of tickets and nearly doubled his money. But he still hadn't told his wife, Marge. One night while sitting around a campfire, Jerry let Marge in on his secret. He was playing the lottery. He knew how to beat it. He had a system. He had already won over five figures. Marge didn't react. Jerry told her he wasn't doing anything illegal. He was just playing the game the way it was meant to be played. Except he had found a loophole. Marge was all in. As it turned out, roll downs would happen every Six weeks. He and Marge knew all the convenience store owners in the area, so they weren't bothered when the Selbys would stand at a lottery machine for hours on end buying thousands of tickets. The the strategy became so profitable, the Selby's invited their six grown children to participate. Then Jerry created a corporation called GS Investment Strategies and sold shares for $500 apiece to friends and neighbors. After 12 weeks of big roll down profits, the winfall lottery was shut down due to declining ticket sales. But a friend alerted Jerry to another similar windfall lottery in Massachusetts, nearly 700 miles away. So the Selbys traveled to Massachusetts every time there was a roll down, going as far as spending $720,000 on $2 lottery tickets. Then they would rent a motel room and go through each and every one of the 360,000 tickets looking for winning numbers. After nine years, the Selby's had grossed over $27 million in winning tickets for a net profit of 7.75 million before taxes. That's when a Boston newspaper started investigating locations where lottery tickets were being sold at an extraordinary volume. That triggered an investigation by the inspector general. But as it turned out, the Selbys had been playing by the rules. The lottery had worked the way it was designed to work. The Selbys had just discovered a very lucrative legal loophole. Don't go away. We'll be right back. Dude, did you order the new iPhone 17 Pro? Got it from Verizon, the best 5G network in America. I never looked so good. You look the same. But with this camera, everything looks better. Especially me. You haven't changed your hair in 15 years.
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Back in 1996, Pepsi launched a new promotion called Pepsi Points. Essentially you could save Pepsi labels and redeem them for points. Those points could get you anything from a mountain bike to a baseball hat. Then Pepsi put a lot of money behind this commercial. It begins with a young man wearing a Pepsi T shirt. Words appear on the screen that say t shirt 75 Pepsi points. Then the kid appears wearing a jacket, leather jacket, 1450 Pepsi points. Then he walks outside and puts on sunglasses. 175 Pepsi points. Introducing the new Pepsi Stuff catalog. Then the commercial shows a group of students in a classroom and the shadow of a jet flies over overhead. Outside the school, a fighter jet lands on the grass. Now the more Pepsi you drink, the more great stuff you're going to get. When the cockpit slides open, the kid we saw in the Pepsi T shirt looks at the camera and says sure beats the bus. Words on the screen say Harrier fighter. Seven million Pepsi points. Drink Pepsi, get stuff. One day a 20 year old named John Leonard saw the commercial on TV. He recorded it on his VCR and played it back over and over again. He couldn't believe what he saw. The Pepsi commercial had no fine print, no disclaimer. That meant you could actually get the Harrier jet. If you could find a way to accumulate 7 million Pepsi points. He did some quick calculations. His family would have to drink 190 Pepsis a day for 100 years. That wasn't going to work. The other way was to buy 16 million cans of Pepsi, which would cost over $4 million. Being a 20 year old, he had no money. But he knew someone who did. John Leonard loved to climb mountains. And he had met a millionaire named Todd Hoffman on one of those climbs. So he called Hoffman and pitched the idea. 16 million cans of Pepsi. It would take 600,000 cubic feet of storage space and 45 people to cart and stack. It all cost $4 million. But that $4 million would get you a Harrier jet worth 32 million. Hoffman was interested. His first question. Was is it legal to own a Harrier fighter jet? Leonard called the Pentagon and asked. He was told yes, as long as the jet had no missiles. Next question. What if we start buying 16 million cans of Pepsi and the contest ends before we accumulate them all? What do we do with millions of cans of Pepsi? The idea was just too insane. Hoffman was out. Not long after, John Leonard walked into a convenience store and saw a marketing display for the Pepsi promotion. He grabbed a Pepsi catalog and noticed some fine print. It said, once you submitted labels totaling 15 Pepsi points, you could buy additional points for 10 cents each. That meant you could purchase 7 million Pepsi points for $700,000. That was a lot less than $4 million. It was a major loophole. When he told Hoffman, Hoffman wrote a check for $700,008.50, and they sent it to Pepsi. Then they waited and waited. One day, a letter finally arrived from Pepsi. It basically said, ha ha. The Harrier jet thing was a joke. Here's your check back and coupons for two cases of Pepsi. Todd Hoffman took that letter to his law firm. The lawyers gathered in the boardroom and asked to see the commercial. They asked for it to be played again and again. There was no fine print, no disclaimer. So they drafted a letter to Pepsi saying, you made an offer. Your offer was accepted. We sent the check. Send us the jet. Otherwise it was false advertising. Pepsi responded by suing John Leonard. So Leonard and Hoffman sued them back. They knew Pepsi outgunned them in the legal department. But they had one powerful thing in their back pocket. They had the commercial. Pepsi then invited Leonard and Hoffman to New York to try and settle the issue. At that meeting, Pepsi wrote an offer on a piece of paper and slid it across the table. It was for $750,000 they were paying them to go away. John Leonard and Todd Hoffman excused themselves to chat in the hall. When they came back, the lawyer said, so what do you think? Hoffman said, johnny wants the jet. From that point on, it was a legal waiting game. Then Leonard's lawyer discovered Pepsi had run the Harrier jet commercial in Canada at the same time. But that ad carried a disclaimer. Obviously, Pepsi had made a mistake by leaving it off the American version. Then, in 1998, three full years after John Leonard had first seen the commercial, the lawsuit finally went to court. The judge ruled in favor of Pepsi, stating a reasonable person wouldn't find the offer credible. After all the time and effort, John Leonard didn't get his Harrier jet. Over the years, the advertising agency took the brunt of the scorn for the commercial snafu. But in a Netflix documentary titled Pepsi, Where's My Jet? The creative director on the Pepsi account, Michael Patty, revealed something he said when he first presented the commercial idea to Pepsi. He had written 700 million Pepsi points to get the jet. The Pepsi client said the 700 million line was too hard to read on screen. He insisted it be changed to 70 million, but then he thought 70 million was still too hard to read, so he had it changed to 7 million. It wasn't the advertising agency that got Pepsi in trouble after all. It was Pepsi itself. It's remarkable to think that with all the law firms, the lawyers, the impenetrable legal language, and the vetting, loopholes can still be missed. That's why when Jerry Selby first read the Windfall Marketing brochure, he was convinced a lot of people would spot the same loophole. As he said, all it took was grade 6 math. Yet people still missed it. In all of our stories today, marketing played a significant role. Whether it was the brochure that triggered the Selby's plan, or Anheuser Busch shortstopping a rule to promote its beer, Berry Gordy figuring out how to generate record sales, or Vulpec using a video to leverage their fans to take a loophole for a loop. Then there was John Leonard and the Pepsi commercial, a 20 year old kid who took on a major corporation and probably should have won that lawsuit. All of which proves one thing. It pays to read the fine print when you're under the influence. I'm Terry O'Reilly. This episode was recorded in the Tear Stream Mobile Recording studio producer Debbie O'Reilly sound engineer Jeff Devine Research Patrick James Aslan under the Influence Theme by Ari Posner and Ian Lefever music provided by APM Music. Follow me on social @terry oinfluence if you're enjoying this episode, you might also like the risk in the asterisk. Fine Print and advertising disclaimers season 8 episode 23. You'll find it in our archives on your favorite podcast app. You can now find our podcast on the Apostrophe YouTube channel. See you next week. Fun fact when Wolfpeck uploaded a response criticizing Spotify's decision, the band was able to make money off that two. Dude, did you order the new iPhone 17 Pro? Got it from Verizon. The best 5G network in America. I never look so good. You look the same. But with this camera everything looks better. Especially me. You haven't changed your hair in 15 years.
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Under the Influence with Terry O'Reilly
Episode: Johnny Wants The Jet: The Loopy World of Loop Holes
Date: October 11, 2025
Host: Terry O'Reilly
In this episode, Terry O’Reilly explores the fascinating, creative, and sometimes accidental world of marketing loopholes. From hockey strategies and record label tricks to lottery schemes and the legendary “Pepsi Jet” lawsuit, O’Reilly reveals how individuals and companies exploit gaps in rules to gain an edge. The stories illuminate how reading the fine print—and sometimes missing it—can change fortunes, rewrite rules, and create pop culture legends.
[03:46]
[08:12]
[12:15]
[17:43]
[24:09]
Terry O’Reilly wraps up by underscoring the power—and unpredictability—of loopholes in marketing and pop culture. Sometimes the simplest rules can be upended by observant individuals, and sometimes even billion-dollar corporations miss critical fine print. The episode ends on a note of playful caution: always read the fine print, especially when you’re under the influence of marketing.