Time’s Web3 bet

Keith Grossman is content to wait out the crypto winter

Quick favor: Please share The Rebooting with a friend or colleague you think would find it valuable. I stumbled onto Substack’s “top list” for business publications, and found The Rebooting there, so that’s a good sign. I haven’t figured out all the growth levers yet for this kind of media, but what I’m pretty sure of is referral is most effective. I’m still unsure about offering the lure of a TRB-branded coffee mug, but I’m open to a pivot to merch. In the meantime, my referral reward is a thank you.

This week:

  • I spoke with Time president Keith Grossman about his attachment to Web3
  • The pitfalls of hypocrisy
  • Downturns as sorting mechanisms
  • The interplay of running and writing

First up, a message from Permutive. If you haven’t already, check out the podcast I did with Permutive CEO Joe Root about why further privacy regulations are an inevitability and how all sides of the media business need to prepare.

Audience-owners are the guardians of user data. By ensuring that it is protected, publishers and advertisers regain their central place in the process of discovering, planning for and activating audiences. Permutive ensures that every targeted ad impression, from open auctions to direct, is based on consented, non-PII, directly-sourced data. The Permutive Audience Platform empowers publishers and advertisers to responsibly activate audiences without any third-party access to personal data.

Why Time’s Keith Grossman is still a Web3 believer

The Gartner Hype Cycle is undefeated since its debut in 1995. New technologies explode onto the scene driven by evangelical fervor. They promise a new world, a utopia, an overturning of the old way of doing things, resulting inevitably – we are an excitable species, after all – in a Peak of Inflated Expectations. And then… they hit a wall. That’s when the Trough of Disillusionment hits, ultimately followed by the Slope of Enlightenment.

I’ve seen this cycle repeat itself with the original commercial internet, when the dot-com bust caused many to write off the whole thing as a fad promoted  by West Coast huckster, and then the shift to mobile, when many dummies doubted whether Facebook could ever make money from tiny ads on phones. It’s not a stretch to see the similarities with the uneven and messy development and deployment of blockchain technologies.

The crypto winter has pitched the giddy excitement over the endless possibilities of Web3 – my definition: a collection of blockchain technologies that aspire to give users new rights and controls over the platforms and tools they use – into the Trough of Disillusionment. Consider:

That’s just a sampling, too. The drumbeat of negativity hasn’t shaken Time president Keith Grossman’s confidence in Web3 providing a new path to sustainable business models. Time, now under the ownership of billionaires Marc and Linda Benioff, has become the most aggressive large publishing brand in exploring the possibilities of Web3. To date, Time has:

“I started to see collaboration. I started to see Web 2.0  is about the audience, but Web3 is really about community,” Keith told me on this week’s episode of The Rebooting Show. “I started to see a different way in which brands could evolve. “

Keith and I discuss Web3 within the context of Time’s growth agenda. Legacy magazine brands are in a tough spot. There are plenty of examples of these publications entering a strange zombie state in which they’re not quite dead but also not quite alive, mostly used as a way to milk revenue from their brands through licensing, SEO and other harvesting. There are multiple paths to take, but I appreciate that Time has a growth agenda, helped, as Keith notes, by being a private company that has the luxury of taking a longer view.

“What you look for is a brand that has a small perception today but huge potential, not one that is larger than what its potential can be,” Keith said of Time. “That give you the room to expand the brand.”

Check out the episode with Keith on Apple and Spotify. We also address the incredibly niche issue of whether it’s better to live in New York or Miami.


We live in a time of purpose. Companies have cast about for ways to turn themselves into something of a mission. You can’t just make paper towels, you need to empower families to build remarkable homes. I can only imagine how much “brand purpose” will be thrown around in Cannes later this month. This can be a sound approach. After all, research shows “purpose-driven brands” grow quicker. The problem is when this kind of purpose runs up against hypocrisy. (I’m fully aware that journalists obsess over hypocrisy more than regular people who have bigger concerns in life.) Apple’s brazen move to use the figleaf of protecting privacy to harm rivals and build its own competitive advantages in digital advertising has surprisingly gotten little mainstream focus. Must not retail as well as Facebook-is-destroying-the-world stories. Privacy-focused browser Brave is also beating a hasty retreat after its privacy purpose was undermined by a direct mail campaign that failed to anonymize the names of recipients. The lesson for me is more humility. Companies are too often too full of themselves, whether it’s in their idiotic and high-falutin mission statements, glomming on the latest political issue or pandering to ESG activists. Making stuff people need is a good mission. Doing it ethically and responsibly is even better. But better to take a break from being so preachy because it often ends up bad since every company has to make compromises.

Sorting mechanisms

I got a note this week asking for more thoughts on what steps to expect from publishers during a recession. One critical step is in mindset: The boom-and-bust nature of capitalism makes downturns not a bug but a feature. They are, in essence, a sorting mechanism that corrects for overinvestment and froth that capitalism inevitably produces. Most companies with strong foundations shouldn’t shy away from such tests. Tactically, a few points:

  • Focus on what’s working. One of the hard parts of operating a business is focusing on what you’re good at while spending on developing new capabilities. I always felt  a natural rhythm at Digiday over the years was periods of expansion followed by times of consolidation. Downturns are time to consolidate.
  • Adapt to your customers. Dunno, maybe this is too obvious, but listening is the most important part of sales, and sometimes that’s overlooked during frothy times when closing deals is just easier. My brief experience in sales with The Rebooting has led me to believe it’s not that different than reporting: You gotta listen and pick up signals for what’s important.
  • Slow down but don’t stop. I remember before the Iraq invasion – the second one – feeling the uncertainty paralyze the business where I worked. Decisions just weren’t being made. Uncertainty breeds delay, and it all rolls downhill. There is clearly a need to slow down – hiring, spending, product launches, expansion plans – but that can’t mean paralysis.

Final note: On running and writing

Running and writing are complementary activities. Both are completely basic. We start running almost immediately after we learn to walk. We start writing at about age 5. In both instances, most people move on to other things, but a small group of people are attracted to these solitary activities. Whenever non-runners asked why I run so often, I tell them I never felt worse after a run then before a run. The same holds true for writing. Both require consistency. Both force you to confront your limitations. Both force introspection. Both reward persistence. One of my favorite books on running is “Once a Runner,” which describes the main character’s attraction to running this way: “It was all joy and woe; it made him weary beyond all comprehension. But it also made him free.”

Thanks for reading. I’ve just arrived in Portugal for the FIPP World Media Congress. I’m excited for the event, but also to return to Cascais, where I once went on a family vacation in 1993. Shoot me a note if you’ll be there: bmorrissey@gmail.com.