In 2009, a CEO at some financial research firm in Ohio opened a cardboard box and pulled out a device that looked, in the words of the man sitting across from him, like a cheese grater that had been forced into a marriage with a disc player.

That device was the first Roku.

The man across the table was Kirby Grimes, then a UX designer doing perfectly forgettable corporate work. The kind of job where you log in, push pixels around, log off, and go home and quietly resent your own talent. He was about to be told the company wanted a Roku app. Nobody knew what a Roku was. Most people called it "Raku." Half of them did not understand that the internet was now connected to your television, which, in retrospect, is a hilarious thing to have to explain to a grown adult in 2009, but here we are. The future arrived in a box and most people thought it was a kitchen appliance.

That cardboard box launched a career.

Kirby and his business partner Tom Schaefer went on to build Float Left, one of Roku's first development partners on the planet. They built apps for Nickelodeon. They built apps for everybody. If you watched something on a connected TV between 2010 and 2020, there is a non-trivial chance Kirby's fingerprints were on the thing you were watching it on. Float Left got acquired by iMedia Brands. Kirby walked, started 4320, a B2B marketing and brand positioning agency for media tech companies, and then, eighteen months ago, decided the trade press covering his industry was so boring, so sanitized, so allergic to telling the truth, that he would just go ahead and start his own publication.

It is called The Streaming Wars. It is good. You should read it. I will wait.

He also raps.

Not metaphorically. Literally. The man records singles. He performs them. He has a Spotify profile. There is a song called "Anti-Thought Leader Thought Leader," which is also the name of a t-shirt he prints, which is also a philosophy he has about the entire content marketing industrial complex, which we will get to in Part Two, because I am a professional and I understand pacing.

He is 43 years old. He did graffiti as a kid. He owned a record label in high school. He went 42 years on this earth without watching a single Star Wars film, a fact he announced in his pre-interview questionnaire as if it were a personality trait, which, honestly, fair. He brought a therapist to his desert island and explicitly excluded family from the list, on the grounds that bringing your loved ones to suffer alongside you on a deserted island is, and I quote, the antithesis of love. He also excluded guitar players, because he plays guitar and is sick of guitar players. He wants a drummer. Or a horn section. Anything else. Anything.

This is not the guy you usually see on the streaming industry panel circuit.

The streaming industry panel circuit is populated by people in expensive blazers saying things like "we are leaning into a multi-platform monetization framework" while a moderator nods sympathetically and the audience checks LinkedIn under the table. Kirby is not that guy. Kirby is the guy who will tell you, on the record, that YouTube is television and the people arguing it isn't are using the wrong scoreboard. He will tell you that Wall Street is actively making the streaming industry worse. He will tell you that thought leadership is not a mystical art form, it is just the earned secrets in your head turned into content, and the reason most of it is bad is that most people are too lazy to reflect on anything for longer than the time it takes to microwave a Hot Pocket.

He will say all of this with the cheerful confidence of a man who has built and sold a company, runs two more, and does not need anyone's permission to be honest.

I have been ranting publicly about the state of digital publishing for years. The recipe sites that make you fill out a healthcare skin quiz before they will tell you how long to boil pasta. The news sites with an ad every fifty words. The display banners screaming for your attention while you are trying to read about the Federal Reserve. It is unusable. It is broken. It is, depending on your mood, either the natural endpoint of a market correcting itself or an industry collectively walking off a cliff while holding hands and pretending the ground is still there.

Spoiler: it is the second one.

Kirby has thoughts on this. A lot of them. Some of them will make ad ops people stand up at their desks. A few of them will make CFOs at publicly traded media companies need to lie down.

He has a framework, actually, that I have not heard anywhere else, about the three cognitive states of advertising and why almost everybody in the industry is solving the wrong problem. He has a model for what should replace display advertising in B2B trade publishing, and he is currently running it as a live experiment with his own publication. He has predictions about which streaming companies survive the next ten years and which ones get eaten. He has a take on the YouTube-is-TV debate that will annoy people on both sides, which is usually how you know somebody is telling the truth.

He has an answer for what is actually wrong with the streaming industry, and the answer is not the one the trade press is comfortable printing. Which is why the trade press is not printing it. Which is why I am.

We talked for almost an hour and a half.

What came out of that conversation is the most honest, useful, frustrated, funny take on the state of media I have recorded this year. The frameworks. The predictions. The parts where he goes after specific platforms by name. The part where he explains why the entire ad-supported model in B2B trade publishing is broken and what he is doing instead. The part where he predicts the 2036 streaming landscape and tells you which four companies are still standing. The part where he names the single most underrated thing in the industry, which, when you hear it, will reorganize how you think about every direct-to-consumer streaming product on the market.

That is all in Part Two.

Part Two is for ADOTAT+ subscribers.

Here is the deal. The trade press in this industry is, with a small handful of honorable exceptions, terrible. It is press release laundering. It is corporate stenography. It is the same nine people interviewing the same nine executives saying the same nine things, and then everybody gets on a plane to Cannes and pretends this is a functioning ecosystem. It is not a functioning ecosystem. It is a hostage situation with a media kit.

ADOTAT+ exists because somebody has to do this differently. No PR-laundered fluff. No platform tongue-bathing. No pretending the emperor is not, in fact, completely naked and also slightly drunk. Just the actual conversations, the actual analysis, and the actual takes the rest of the industry is too polite or too compromised to publish.

Part Two of this Kirby Grimes conversation drops behind the paywall this week. The frameworks. The predictions. The names. The receipts.

Subscribe to ADOTAT+. Read the part that matters. Stop reading the trade press that is lying to you.

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