A Mad Men retrospective

The Thinker by Rodin

Eight years ago I wrote a retrospective for the TV series The West Wing, which lasted seven years on NBC. I am finishing the last season of Mad Men, which also lasted seven years. Mad Men appeared exclusively on AMC, a cable network, unless you include the many services belatedly streaming the show, including Netflix where I watched it. Netflix doesn’t have the last seven episodes available, however my wife has her ways so I am able to watch them anyhow.

Starting the series some months back I had to admit this was an unlikely choice of a show to hook me. It focuses on Madison Avenue in the 1960s. If you’ve been living under a rock, Madison Avenue is known principally for its advertising agencies. This was certainly true in the 1960s. Mad Men is a deep dive into this unlikely world, centered on Don Draper (Jon Hamm), the creative director for the fictional Sterling Cooper ad agency. Sterling Cooper is filled with creative but deeply flawed people. Some like Draper also have natural good looks as an asset. Draper may be a creative ad guy but he is something of a wreck as a human being. Aside from smoking and drinking too much (typical of those with the means in the 1960s) Draper is also a chronic womanizer, constantly in and out of beds of principally very beautiful women, all while being married.

He is hardly the only one in the office to engage in these peccadillos. Most of his fellow partners are doing the same, and this includes the son of one of the founding partners Roger Sterling (John Slattery) who has a torrid on again, off again relationship with the office manager Joan Harris (Christina Hendricks). It’s a world of directing work from the upper floors of tall Manhattan skyscrapers, suits, frequent dinners with clients and personality dramas. With the exception of Joan and Don’s secretary Peggy Olson (Elisabeth Moss) who becomes a copywriter, women are invariably secretaries. Pretty much every man in the place has one outside his door. The women peck away at their IBM Selectric typewriters and answer the phone while waiting to find the right guy to marry, who is often their boss.

It’s a world of wooing clients, losing clients, making pitches to clients and tenuously trying to maintain clients while dressed in fancy suits, smoking too much and drinking too liberally, mostly from the bars in their offices. These men drink more than most sailors; it’s a wonder they can function at all. And yet producer and creator Matthew Weiner makes this world eminently watchable anyhow, despite the white shirts, shined shoes, and neatly trimmed and parted hair. You want to root for someone in this show but it’s hard, not because everyone is evil but because they are caught in a system that rewards deceit. Peggy Moss is the closest the series comes to such a character. As for Don Draper, he’s pitiable and thus hard to root for until you get his weird but compelling backstory.

What the show has going for it is top notch writing and directing, overseen by its obsessive creator Matt Weiner, as well as standout performances by actors who are frequently required to show their characters’ seamier sides. Equally impressive in this period drama was the attention to detail to the turbulent 1960s. Many events at the ad agency overlap with dramatic news stories, such as John F. Kennedy’s assassination and the moon landing. In a world where image is everything, everyone including the spouses tries hard to model their image while the story and camera takes us into their backstories.

There are lots of good characters to enjoy, but few you can feel sorry for. You can feel sorry for Betty, Don’s first wife played by January Jones until you discover she’s pretty insufferable herself. There’s the eager new exec Pete Campbell (Vincent Kartheiser) with his own Stepford wife back at home who, like George W. Bush, has to live up to the family’s expectations. It would take too long to list all of them, particularly when so many of them drop out to be replaced by others. There are crises both personal and business-related, sometimes at the same time. Don himself gets pulled more ways than Silly Putty. There are societal issues that creep into the insular ad agency world, including women’s liberation, racism, drug use, the space program and computers. From the first frame to the last, you really feel like you are living in the 1960s. I lived through these events, although I was a child at the time, so I can say it is eerily authentic. If nothing else, Weiner nails the 1960s and gives the viewer a largely accurate depiction not just of the world of advertising but of one of our most transformative decades. Much of the craziness we are living through in the 2010s has its roots in the 1960s, so the show helps you put today in perspective.

The show is principally centered on Don and Peggy, but more on Don than Peggy. Fortunately both Hamm and Moss prove up to mastering their roles. A closer inspection will find other things to admire. For example, the directing is outstanding throughout, and the transitions between scenes are often inventive and very clever, like the advertising world. I found excellence in places I did not expect. For example, Kiernan Shipka does a terrific job as Don’s daughter Sally across seven years of the series, and grew as an actress in the process. By the last season her role was mature and her acting was so good you could see her model both character’s mother and father mannerisms.

Mostly I was surprised that Weiner could make this sort of show work across seven seasons so consistently and with such uniform excellence. I really wanted to not like this show, as I find advertising reprehensible, but I was suckered in anyhow and kept spellbound for much of the series.

In my retrospective of The West Wing I said it was a classy show rarely seen on network TV at the time. Given that Mad Men was only shown on cable, its excellence and commitment to quality is a delightful surprise. It’s a compelling character drama and worth the investment of time, delight and heartache to watch all seven seasons worth.

Ashley Madison stupidly lets itself get pwned

The Thinker by Rodin

So I have been streaming Mad Men on Netflix. It’s a strangely compelling series about the world of Madison Avenue in the 1960s. It’s a world of constant drinking, endless cigarettes and infidelity. The principle character is Don Draper (played by Jon Hamm), the creative director for the advertising firm Sterling & Cooper. As we quickly learn, Don was previously Dick, he is a deeply messed up man, and he also happens to be one hunk of a guy. Don’s a liberal drinker, a liberal smoker and a liberal bed hopper as well. He does this while somehow staying married to his ultra pretty and slinky wife Betty (January Jones).

It takes a few seasons but Betty eventually figures out Don’s infidelities. They divorce but Don keeps bedding the women, often inappropriately, including his secretary. Yet Don is hardly the only character in the series with his pants down. Most of the characters are involved in an illicit relationship or two. I have no idea how close any of this is to real life on Madison Avenue, but from what I’ve read it was not too far off the mark. Most of the men are caught between who they really are and the roles they are supposed to play. How they manage all this screwing around in these pre-Ashley Madison days is kind of mysterious, but likely all that booze helped reduce inhibitions.

Yesterday of course the infidelity website ashleymadison.com quickly went dark after hackers posted a dump of its database on a number of websites. While bad for cheaters out there, what it said about Ashley Madison was even worse. First, its security system was laughably bad. Second, even after the hack they could have taken down their site and saved their forty million members embarrassment, but they didn’t. They kept collecting fees right up until they went dark. In short, they gave the online infidelity business not only a moral stink but in an unexpected way: they were so busy chasing short term profits that they were willing to throw its forty million customers on mercy of their spouses. Doubtless the hackers provided samples to prove they had hacked the good stuff, including apparently seven years of credit card transactions. AM was hoping they would blink.

Doubtless too that marital counselors and divorce lawyers are going to get a sharp increase in business. It would not surprise me if their phones were ringing off the hooks. As for AM, I wouldn’t blame its customers if they arrived en masse to torch its offices. Cheaters of the world, unite! Anyhow, fifty years after Mad Men, there are still plenty of Don Drapers out there that are mostly hooking up online. Until a couple of days ago apparently Ashley Madison had the lion’s share and then some of this market.

What interests me is not that AM brokered infidelity. As disgusting as most people at least claim to view infidelity and those that aid them, there are far worse things on the Internet, with ISIS beheading videos coming immediately to mind. Some entities like AM are to be expected in our electronic age. What’s interesting and more than a little appalling is how bad a job they did in keeping their clients’ information confidential. As a software engineer, but also as a guy that is currently getting paid to ghostwrite articles about data security, AM gets an F.

Yes, AM kept a record of all its credit card transactions for the last seven years! It’s such a mind boggling, stupid and reckless thing to do, particularly given the profitability of the site. It would have made much more sense to give in to the hackers’ demands and quietly establish a new site under a new name, oh and fix those security problems too. Doubtless they had the money to do it. Forty million customers, figure 30 million of them men, figure each putting out at least $50 each, that’s at least $150 million in revenue. Since they’ve been in business fifteen years, it’s likely a lot more than that. Likely their overall revenue likely exceeded a billion dollars, not that we’ll know for sure. They aren’t publicly traded, although maybe their successor or whoever buys the brand (Vivid Entertainment?) will be publicly traded, and doubtless do a better job at security.

If I had fewer scruples and more money I might create the next AM site, one that its dubious clients could actually trust. Of course there are always risks in anything done over the Internet. AM’s clients now understand that. The next AM is bound to arise from its ashes, and probably sooner rather than later. Here are some actions items for whatever entrepreneur wants to sail in these turbulent waters in the future:

  • Do not keep records of credit card transactions. Just don’t. Purge these daily, if not more often, from any internal databases. Don’t journal them on backup somewhere.
  • Do not collect any privacy information from your customers, you know like their real names, address and phone numbers. Instead, let some third party act as your broker. Your client gives the broker some money and the broker provides some electronic token identifying the payee that doesn’t actually identify them to your company. The future AM should never collect anything that could identify their clients.
  • Accept more discreet ways of payment. There are lower tech and anonymous ways to pay fees confidentially: wire deposits and money orders, for example. I’d say accept BitCoins but BitCoins are hardly anonymous.
  • Don’t use cloud hosting. Use your own data centers that only you can access and control.
  • One person can’t do this in his basement. So find employees who have a history of being trustworthy, very talented, and discreet and pay them very well. Give them incentives to be discreet. Make their bonuses contingent upon their contributions to improving the business’s security.
  • Retain security experts. To get AM’s entire database required a whole lot of bandwidth. This can be monitored. The tools exist to cut off suspicious behavior already.
  • Do regular vulnerability testing of your website and applications. The tools are out there. Of course fix any vulnerabilities found quickly.
  • Hire a CISO, a Chief Information Security Officer with of course the right credentials.
  • Don’t store obviously sensitive information, like a client’s IP address. Passwords should be encrypted in a MD5 hash in the database.
  • Tell your customers what your security plan is. Get an annual (or more often) security audit from a trusted security auditor and publicize the results for your customers.
  • Provide your customers security tips, like clearing your browser history. I can think of another one. Figure out a way for clients to share pictures anonymously. I’m pretty sure it could be done with Instagram.

As for AM’s clients, those who are not on their way to marital counseling or divorce court, you might consider picking up strangers at bars again or just plastering them with lots of alcohol in the privacy of your office. It sounds cheaper and faster. It worked for Don Draper.