Artists, suits, engineers

My approach to analytics is a bit old school. I look at dashboards like we all must, but I tend to put more weight into what I hear from people than open rates or download numbers. That’s because this kind of model doesn’t work neatly within the industrial process of media. I’ve found over the last two years that I’m more likely to hear about podcasts than newsletters.

Email has been the workhorse of digital media for over a generation. It is not dead or close to it. What I think is going away is email as the totality of a media product. I see it more as infrastructure. True, email is less reliable as a distribution channel than it has been, but it is still core to developing a direct connection with an audience.

Substack’s recent messaging about email becoming less reliable struck a chord. Pushing people into the app was a major reason I departed Substack. I’d seen enough time how publishers got trapped on platforms and sacrificed control of their audience. The app itself is a good reading experience, but as a publisher, I didn’t like the intermediation tradeoff. 

Meanwhile, Beehiiv, which is a partner of The Rebooting, is rolling out podcasts, webinars and more publishing tools. I still believe in email, only it’s inevitable that most successful newsletters become multi-modal, whether with texting, podcasts or streaming.

Today, I’m unpacking why I see the shape of media organizations dictated by their mix of artists, suits and engineers.

Reminder: If you’re coming to Possible next week, we will have an informal lounge set up at Nobu on Tuesday. We are recording a series of executive video interviews there as part of a series underwritten by EX.CO and we will open the space for a respite from the craziness of the Fontainebleau lobby scene, in case you want a quiet place for a call or meeting. We are also holding a media executive dinner at Possible on Monday, April 27. Thanks to our partners at Marvelous Works, Core Advisors and Launch Potato for their partnership. Let us know if you’ll be at Possible by dropping a note to Marci Chocky: [email protected].

Please fill out this form if you’re interested in invitations to our activations there and elsewhere during the year.

The hardest part of the media business is managing tensions. The core tension in media businesses has long been between content and sales. This is the artists vs the suits. It’s a tension that exists in most content business. 

I take an expansive view of artists. The Artists are in various fields, from ad creatives to designers to actors to writers to journalists. They’re defined by their motivations. Unlike suits, artists are not intrinsically motivated by money and overindex in chaotic energy. This drives the Suits crazy because it makes no sense. Artists create media because they want it out in the world.

Artists create different types of products. They tend to skip a lot of the market sizing exercises and instead trust that they’ll figure that out (or not) later. They tend not to have three-year plans. They often favor optionality and autonomy. They tend to have what the Silicon Valley people call taste, which I’d recast as sensibility. Artists operate by feel, not spreadsheets. They’re Bill Bradley in “A Sense of Where You Are.”

Suits make more money but have lower social status. It’s a tradeoff every Suit will take because Suits are practical people. At their best, Suits are what Hearst Newspapers exec Bridget Williams calls “thoughtful mercenaries.” They recognize that the Artists need to be saved from themselves. Suits often get a bad wrap from the Artists but in truth, the Suits are the most important people in the organization. That’s because if the Suits don’t sell, nobody eats. This is why everyone should honor sales. 

The new entrant to this mix is the Engineer. For the last couple weeks, I’ve been helping out Troy with his vibe coding project that’s grown surprisingly sophisticated. It’s made me realize that engineering is decoupling from technical expertise. Just as most writers I know cannot diagram a sentence and often have a shaky grasp of grammar, engineering is less a collection of technical skills than a Rick Rubin-like understanding of products.

The Engineers tend to work backwards from what works. They reverse engineer successful products. You can media products like TBPN, which reverse engineered successful models in streaming (Twitch) and linear TV (SportsCenter) to create a new media product. The Engineers are defined by their fealty to finding growth hacks (clips in TBPN’s case) and attention to the details, particularly in matters of optimization.

The most successful Media People are a mix of all three. The best Suits have artistic sensibilities, and the most successful Artists have understood business dynamics. Now, engineering, freed from technical gatekeeping, is a third core competency.

Most media products suffer from being too weighted in one direction. My initial reaction to the TBPN clone Monitoring the Situation is that it feels too engineered, as if someone tried to unpack what made TBPN work and optimized it to expand the TAM. Engineered media risks feeling soulless. TBPN was born of an engineering approach combined with singular talent in its hosts to make uncool people feel cool by proximity. That kind of talent is artistry. 

You can tell a Suits-driven product when you see it. At their worst, they feature a “content slit” that is compressed on all sides by what Troy would call “high ad density.” They admirably do not overthink it when it comes to monetization. Where there’s an opportunity for incremental revenue, you will find Suits. This can, of course, go wrong. By its nature, this approach is rarely centered on audience needs. Suits understand who pays the bills, and rarely in media is it directly from the audience.

Similarly, this is no time for pure artistry products. The marketplace is not rewarding this. A problem of journalism right now is that the purest form of it – original reporting – is not highly valued in the market. In the flood of information that swirls, scoops don’t last long. Earlier this week, a subscriptions-focused publisher said the outlets scoops didn’t drive conversions, in-depth analysis did. Journalism is based around a reverence for scoops, the same way ad creatives venerate the Big Idea. 

Alongside those Big Three are the Coordinators. This is a group that exists in every department of every company. I discount the AI doomer predictions for most areas of business – why do we still have radiologists? – but not for the coordinator class. This is a critical function that will increasingly be directed more effectively by AI systems.

The media industry is simply more competitive than it’s ever been. Being good at one thing is not an option anymore, which is understandably destabilizing for many who immersed themselves in craft and ignored other aspects of the business. The most in-demand people will be deep generalists, who can marry native expertise with fluency in the other core areas. 

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