Contenting is Hard

I, for one, welcome our new professional creator overlords.

Note: If you’re new to this newsletter, it’s a continuation/simulcast of the blog I started in 2004 at I also started a weekly NYC tech/events newsletter in 2009 here, which you can also subscribe to separately. I also tweet and when I’m not producing content, I’m one of the earliest stage investors in NYC, leading pre-seed and seed investments in local startups at Brooklyn Bridge Ventures.

In Kara Swisher and Scott Galloway’s predictions episode of Pivot, Erica Anderson made a call that I couldn’t agree more with:

“The era of everybody having a podcast will close out. Only the best content will survive and be amplified.”

Having been a blogger for almost 17 years now, I couldn’t agree more—and it doesn’t stop with podcasts.

(I still think of this as a blog—but I moved the e-mail version of this over to Substack because that’s feeling a bit like the beginnings of a community platform and an interesting place to be).

I started posting in February of 2004 and by the time 2007 rolled around, it seemed like everyone had a blog. There were conferences and meetups—and some big venture capital dollars followed into platform companies.

One company seemed to be a bet on everyone blogging. Six Apart, the makers of Typepad and Vox (a different Vox), which were meant for indie and small bloggers, raised $12mm from August Capital in 2006.

The other, Automattic—maker of Wordpress—pulled in $30mm at the end of 2007 and was focused on more enterprise solutions as a platform for professionals.

Automattic went on to raise hundreds of millions of dollars and is now seemingly on the verge of an IPO. Six Apart merged into a variety of other companies over the years, shut down Vox, and never seemed to find its way.

That’s what happens with new social platforms:

  1. Early adopters rush in to stake their claim.

  2. Most don’t stick with it.

So what tends to happen with these new mediums? Why do so many people drop off of “the next big thing that everyone is going to be on"?

There are a few reasons for this.

1) No medium will work for every means of expressing yourself.

Each new social media platform enables users to do slightly different things, with the various features, limitations, etc. fostering different types of creation that plays into the strengths of different types of people. People good at Twitter or desiring to consume it has very little to do with participation or consumption on TikTok, Youtube, Medium or a newsletter.

I can see this with my own blogging. It used to be the place where I posted every thought—my publishing tool for everything. I would often post brief thoughts on my blog multiple times per day—tweeting before Twitter was a thing.

Once I joined Twitter, that micro-activity moved to that platform as well as Instagram over time.

I still like to write, though—and so for the past few years, you can count on me for at least 30 or so posts per year.

Other people just haven’t kept up at all.


2) Coming up with good content is hard.

Choosing a topic is hard. Being interesting is hard. Staying engaged with your audience is hard. So is driving traffic.

Most Clubhouse rooms are, well… pretty terrible, much in the same way that most conference panels are pretty terrible.

That Power Law of Quality is true of podcasts, TikToks, Meetups, blogs, Instagram accounts, newsletters, Skillshare classes, etc.

The two sides of “democratization” of this form of expression is that while we’re no longer beholden to the laziness, cronyism and structural inequity that occurs in the programmed media world, we’re opening up the floodgates and letting the audience dominate the conversations, often with mixed results.

I mean, once in a while, Soundcloud spits out a Billie Eilish, but most of it is a sea of mediocrity. It’s hard to be really good and not everyone is going to find a following. Continuously producing content and not finding success will eventually be disheartening to people and they’ll stop.

Especially when they get nudged aside and…

3) The professionals take over.

In 2007, Fred Wilson wrote the following on how blogs were changing:

“The other thing that has changed is that many of the blogs I "grew up" with are not individual blogs anymore. Rafat has a team, Arrington has a team, Om has a team. ARS, RRW, SAI, Valleywag are all group blogs. They are much better at putting out a stream of blog posts all day long, but they aren’t the same thing as Mike and Om blogging along with me. And you can’t compete with an army of bloggers on the techmeme leaderboard.”

As social mediums tend to go, they tend to professionalize. Sometimes indie creators become pros for practical reasons—because if you do something well, you might as well be paid for it, which requires some infrastructure and overhead to maintain the kind of quality people pay for.

People who are really good will rise far enough that they’ll be able to focus on it full time, leaving everyone in the dust. The money will be in servicing this group and the new features will be, too.

Years ago, Andy Weissman referred to Twitter’s change in how @ replies on Twitter were viewed as “The GaryVee feature.” It used to be that if you followed someone on Twitter, you saw everything they wrote—including half conversations in reply to people you didn’t follow. For some, it was a great way to discover the friends and peers of people you followed.

For others, it became unmanageable. Gary Vaynerchuk was using Twitter 24/7 to build up an audience. Every two minutes, it was tossing shoutouts to people who were “killing it” the way Trump tosses paper towels. He became unfollowable—until Twitter made the change to hide replies to people you didn’t follow.

It allowed people who had professionalized their social media to engage with their audience at scale (and for Comcast to show everyone they were providing shitty service to that they cared).

That’s going to happen to Clubhouse and Substack, too. Feature development eventually follows the money—and the money is in the whales, not the long tail.

Other times, the professionalization comes from other mediums. When you look at the list of most-followed Twitter and YouTube accounts, for example, they’re mostly people who gained a following outside the platform on “mainstream media” like musicians or existing media companies.

How long before the most popular Clubhouse is either CNN Townhall or Josh Constine’s newly venture-backed Clubhouse media company JoshCo?

In fact, these platforms often go mainstream because of this kind of usage. When news outlets started posting their Twitter handles in TV broadcasts, it drove tons of people to the platform. These outlets require a lot of the kinds of features the long tail users don’t really need—and the platform eventually turns its focus towards making CNN happy versus making it easy for someone to come out of nowhere and rise up the charts.

4) People like their friends more than they like strangers—unless the strangers are amazing.

In its search for meaning, Clubhouse sometimes feels like a weird cross between a support group and a SXSW session. Audience members occupy more and more time—making it less about learning from experts and more about connecting with like-minded individuals.

At some point, people realize that they’d actually rather connect directly with these new online friends (or people they know from real life) in smaller, private groups rather than constantly trying to entertain or suffer others.

This is going to be a real test over the summer. When COVID numbers come down and outdoor activities open back up again, people are going to be thrilled to connect with other humans in real life—making the bar for Clubhouse participation over social connection with friends really high.

Come 7PM on a Wednesday night in June, where am I going to want to be in 2021? I have a feeling it’s less likely to be on Clubhouse unless you really like all of the people you’re hearing from or it’s a can’t miss level of content quality.

If the latter, I wonder if the ability to time-shift this level of quality from your favorite podcasts to later at night, or during a walk or workout doesn’t win out.

I’m all for exploration of these new platforms. I’ll participate on them as they come out, but I won’t stick with all of them. Sometimes that’s because I’d rather hangout with my wife or my friends. Other times, it’s because I just can’t dance or flick playing cards well enough to be on TikTok.

Either way, I encourage you to make your own way. Share and participate how you want, because there’s never any one thing that everyone is doing—and even when they do, most people don’t stick with it.

If you’d like to explore the medium together, and you’re in NYC, join me this Thursday, January 21st at 8:30AM ET as I begin a regular room for NYC investors, founders and innovators on Clubhouse.