by Dan Maccarone and Bob Sullivan

The voice is soothing, even sultry, as it cuts through the otherwise empty, black night.

“Overnight, under the covers,” he says, the bass in his voice turned up almost to Barry White levels. He invites himself into bed with you. “Me here, you there.”

Steve Somers is miles away. But suddenly, you aren’t alone.

He’s not offering sex. He’s offering sports. Specifically, “schmoozing S-P-O-R-T-S.” But he might as well be offering sex. Somers helped invent the category of overnight sports talk radio shows in the late 1980s, when there was one all-sports station, WFAN, in New York. Within a decade, there were hundreds of copycats in the lucrative new category. Steve’s late-night style worked because he understood a profound truth about human nature: most people are lonely. Really, really lonely.

It’s no mistake that Somers’ taglines hinted ever-so-gently at another 1980s late-night cash cow — 1–900 telephone numbers. In fact, in graduate school, Bob wrote a paper comparing Somers’ language to the then-ubiquitous TV commercials hawking 1–900 sex phone lines. After all, they were both in the same business. And so, most likely, are you.

The loneliness business.

Most people’s motivations are pretty primal. After they have food, water, and shelter, they want connection. Yes, they want a new television, or a pair of shoes, or a ride, or a piece of software, or a beer. But they really want a bridge. A bridge to other people. They want love. Or at least, like. Lots and lots of like.

Sell someone a thing, and they’ll drop you the moment they find that thing somewhere else. Solve someone’s “like” problem, someone’s loneliness problem and you don’t just have a customer. You have a connection.

This is most obvious in bars, of course. Bars don’t sell liquor; they sell social lubricant. Bud Light tastes the same everywhere. And it’s about 90 percent cheaper to drink it alone in the basement. But (most) people would rather pay $6 for glass of the stuff and…..and what? And a chance at getting some likes. That means if your patron is getting only beer at your bar, they’ll be bar hopping to somewhere else pretty shortly. The difference between “one-and-done” and a whole night of fun could be as simple as a cheery hello and just a few likes.


Corporations kill — and spend billions — for the kind of loyalty that can be won, or earned, for free.

A bartender may just be a “single-serving friend” — like someone you strike up a lovely chat with while waiting for a flight that’s delayed. But he’ll make you forget the delay, and leave you feeling comfortable, rather than awkward, while waiting for a friend who is late. See what’s happened there? There’s magic in making a stranger feel at home.

Irish pubs often have a saying over the door: “There are no strangers here, only friends who haven’t met yet.” That’s not a slogan; it’s a business model.

Teach a newcomer that it’s ok to walk into your bar alone, that uncomfortable feelings can drain away and even turn into warm familiarity, and she will come back: Even, perhaps, alone — a real business coup.

When Dan used to bartend “Sunday Funday,” that same principle applied. The goal wasn’t to sell a single beer, it was to create an atmosphere that kept pints of Blue Moon full, orders of pretzels and fries flowing, multiple groups (many that had just met) laughing together over Cards Against Humanity, and a steady ring as customers’ joy flowed into the cash register one dollar at a time.

That last bit may seems out of place, but when you’re in the business of creating continued splashes of happiness, that is an important part of it. The difference is there’s a humanity to it that spending billions of dollars just can’t fake. There’s the “genuine factor.” And the best bartenders know how to make every customer feel special, hand-hold them through whatever’s going on in their world that day and be the best listener that person has ever met.

Perhaps you aren’t buying that a single smile and hello is enough to inspire a lifetime of loyalty…and you’re right. It’s only a first step. That must be followed quickly by a second step: bringing the consumer into the community. Bartenders don’t have time to engage in long chats with patrons. That’s just not scalable. In fact, the art form requires learning to tell stories or engage in interactions that take no longer than the time it takes to mix an Old Fashioned. The second step is equally important. Bartenders must connect people. They must make introductions, the way a good party host does.


Finding commonality is, of course, the easiest way to ease loneliness. At Dan’s old bar, Destination, the easiest way to bring people together was sports. Spot a few people sitting by themselves, all cheering for the Pittsburgh Steelers or Boston Red Sox, and there’s your opportunity. Perhaps handing a few shots over brings them together, they start talking and they’ll now while away the afternoon together as fast friends. The bar has won.

Trivia Nights do the same thing. When Destination partnered with GawkerTV for a video trivia night, some teams came together, but often groups of two or three merged to spawn temporary friend groups united around their collective ability to outsmart (out snark) their fellow patrons. Again, for those two hours, the bar has won.


Of course, not everyone is great at conversation. And not everyone wants to feel like they are at a real-life LinkedIn or Tinder meeting. That’s where the other truth about the loneliness business rings true.

We are all therapists.

Every day, in every interaction, people arrive at your door with The Problem. Everyone has one. Good companies offer solutions to such problems. But smart businesses begin their sale by selling nothing more than understanding.

With most human beings, it takes less than 5 minutes to find out what The Problem is. The husband won’t listen. The mortgage is too much. Users can’t find the buy button on the website. Customers use your store as a showroom and only really spend money online. Employees hate you. Investors hate you.

They say there’s no vice like advice, and they are right. A good barman doesn’t listen to a customer for 10 seconds and then bark, “Just divorce her.” A good barman — like a good therapist — lets the customer process The Problem, interjecting only clever pieces of wisdom, and only when the time is right. Anyone can offer advice, or a piece of software, or a redesign.

People often land at your bar, or at your consulting firm, because they are hurting. Comfort the afflicted, and you’ll get something far more valuable. You’ll “get it.”

Nothing is more powerful than understanding. Anyone can take a fee; very few people “get it.” If you simply sell a solution to someone, you will likely never see them again. If you sell them understanding, they’ll come back again and again. This is the best way to inspire loyalty, because no one has just one problem.

Doing this can be scary as a business, because offering real comfort and understanding might put you in the uncomfortable position of recommending something that won’t profit you — at least not right away.

When Dan was discussing design for the original Hulu, a seemingly crazy idea came up. What do you do with consumers looking for video that’s not on Hulu? The obvious answer was to nudge them towards “similar” offerings that were on Hulu. “You’re looking for ‘Lost’? Sorry, we don’t have that. How about ‘Star Trek’ or ‘Lost in Space’?” The response from any normal person to that question would be “No, I want to watch ‘Lost.’ Thanks for nothing, Hulu.” After which they’d most likely head on over to Google and type in “Where can I watch Lost online for free?”

That’s what most media and entertainment products were doing back then, but the Hulu team chose to go a different route.The right answer was to help consumers find what they were looking for, even if it was on another site. So that’s what Hulu did. Yup, it sent customers to the competition — “Sorry, we don’t have Lost right now. But you can go watch it on” — a not uncontroversial decision for a young company. Why? Because in the Internet Age, your customers are going to find what they are looking for anyway. You might as well be seen as helpful, rather than as an obstacle.

Hulu had a choice: Right at that moment when a TV show fan was fumbling around looking for entertainment to keep their mind off the real world, it could be a friend or just a busineess. It chose to make connections. It chose to give people a warm, fuzzy feeling. Plenty of Internet firms now do this. Kayak, for example, steers visitors towards cheaper travel deals, even if it doesn’t make them money. News sites — smart ones, anyway — liberally link to competitors when they have scoops and better stories.

The fact is that most people don’t know what sites they’re visiting these days, so take the opportunities that come your way to stand out.


It’s not always the consumer that needs therapy or, rather, to be understood. Sometimes it can be your colleagues — people inside an organization that aren’t necessarily being heard. Regularly, when Dan’s working on products, whether it be with startups or multinational conglomerates, the same issues arise: people aren’t being heard. Taking thirty minutes to sit down and understand where someone has issues with their responsibilities, peers, boss, process, or all of the above can go a long way. Even when they’re looking to figure out how the make an overall product better for consumers, hearing how to streamline a person’s job could actually end up making it better for everyone.

Years ago, when Dan was redesigning Newsweek’s site, employees complained about the amount of “process” required just to populate articles on the homepage. It was clear in listening to the magazine’s team that there was a lot of frustration and too many steps. In the end, creating a more automated process freed people up to do the more interesting facets of their jobs as editors and, in the end, simplified the experience for customers. Everyone was happier.

The same is true in bars. Whether it be a free gift, a friendly bartender, a distinct enhancement to a common cocktail (at Destination, Dan used to add a splash of Guinness to the bar’s signature Bloody Marys), or a unique offering (Destination turned around slow Monday nights by creating “Mac and Cheese Mondays” which gave customers a variety of macaroni and cheese options for every drink they bought), the slight differentiating factor can mean the world to someone and inspire them to come back. Hopefully, with friends.

Don’t get Netflix’d.

On the other hand, there’s cable television. Big firms like Comcast rank near the bottom in customer service year after year, and often do all they can to trick customers into paying more than they should. That works for a while. But it’s no surprise that cable is getting “Netflix’d.” The movie service has done this before.

In his book, The Plateau Effect, Bob goes into great detail about the rise and fall of video rental giant Blockbuster. Many folks erroneously think that Blockbuster was a victim of changing times and technologies. Not true! Blockbuster, a Goliath, was slayed by Netflix, a true David at the time. It’s business model in the early days sounds straight out of the Pony Express archives. It mailed movies to people. Consumers didn’t dump Blockbuster because Netflix was better. They dropped Blockbuster because THEY HATED Blockbuster. With the passion of a thousand fiery suns. Blockbuster famously charged insane late fees, often far exceeding the value of movies rented, and went after “debtors” with the ferocity of debt collectors.

Blockbuster had reverse goodwill; customers couldn’t wait to dump them and say goodbye to late fees. Incidentally, that was a big part of Netflix’s initial marketing.

And so it is with cable. Cord cutting is the new mortgage burning. People don’t just cancel cable TV; they brag about it at parties.

Forget about helping people with loneliness; cable companies, with their endless “please come back” mail offers, are now a lot more like a crazy ex-boyfriend or girlfriend.

All industries face the challenge of serving customer needs versus barreling over customers just to make money. Sometimes the issues are less offensive than how the cable industry has backed its customers into a corner, but other times it’s because corporations can’t see what people want or need because they are blinded by their own agenda.

Several years ago, Dan was doing research for a large media company that wanted to build a variety of services for families — the largest segment of their audience. During this research two findings surfaced very quickly: 1) the products this company wanted to create didn’t resonate at all with parents and 2) there was one single service that every single respondent independently begged for without any prodding. Clearly, this was a product that the media company could and should build.

Towards the end of the research, Dan’s client sent him an instant message in all caps from behind the one-way mirror where she was watching. “GET BACK HERE RIGHT NOW.” After excusing himself, he entered the observation room and his client’s face was bright red and her team was quivering behind her — it was like watching a Disney villain getting ready to strike. “This is awful,” she said. “They don’t want any of the products we’re building!”

“I disagree,” Dan replied. “This is great. There’s only one thing these people want and you can easily give it to them.”

“But it’s not on our roadmap.”

“Then change the roadmap.” It really was that simple. They weren’t building houses or testing medication. They were making a website and changing it would have cost them nothing, probably saved them money in the long run. But instead of listening to their customers, solving a problem and inspiring loyalty, the company went on to build three tools that nobody used and ultimately ended in a digital media graveyard.

Companies that forget about the importance of connection are ripe for disruption. Yes, Uber is cheap and convenient. But Uber has risen to power so quickly in large part people really HATE taxis, and for good reason. Everyone has the story of getting taken for a ride, not to mention the smell.

Treat your friends like that, and you’re going to be lonely. Treat your customers like that, and your balance sheet is going to get pretty lonely, too.

More Barstool MBA:
The Brand as Experience >
The Well-Timed Free Gift >
Everyone Will Steal From You>

Dan Maccarone is the co-founder of Charming Robot, a digital product design agency in NYC. He also hosts the podcast Story in a Bottle, chronicling the stories of tech and media professionals. Follow him on Twitter @danmaccarone.

Bob Sullivan is a New York Times bestselling author and a Peabody award winning journalist. His work can be found at and you can follow him on Twitter @RedTapeChron.

Original Article