The passion of the posts
It might be a golden age for sole-proprietor projects, but everyone is just having a great first week on the job.
Hello and welcome to I’m Late to This, a newsletter from Myles Udland about stuff I haven’t stopped thinking about.
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I’d say we’re just getting started. But, well, this week’s newsletter might disagree.
Dave Portnoy, the new patron saint of Finance Twitter, fired off this take last Sunday to bookend the first “full weekend” of sports in several months.
I don’t have a strong view about his view about sports.
Some of this is working for some people.
Some of it is not working for others. Such is life.
Games are being played in front of simulated crowds so leagues and their media partners can recoup some of the billions of dollars lost to the pandemic so far. Professional sports are a made-for-TV event in normal times, but it’s just not as fun when the quiet part is said out loud.
But it also makes sense that Portnoy finds the current sporting moment dull. Not because of the games, per se, but because he’s found something else much more exciting to focus on — the stock market.
Every day, Portnoy logs on and fires up the #DDTG machine (Davey Day Trader Global) and finds himself in a way few people ever will. Yelling at computer screens from wherever it is Portnoy has set up shop, the founder of Barstool sports is in full flight at the top of his game, feeling his way into a new space in the media universe with the same enthusiasm that turned his yet-another-Boston-sports-blog website into a multimedia powerhouse. Portnoy is now named as a “key employee” in SEC filings, perhaps the first blogger to be so named.
And to see Portnoy infiltrate financial media over the last few months has been to watch, in real-time, an artist explore a new medium. Almost instantly, Portnoy was on about the financial media’s most tired trope: blaming the Fed for stocks going up. But then he pivoted this theme into Office-based TikTok’s and brought along his signature green hammer that makes stocks only go up.
And while Portnoy is no longer a media insurgent, the path he’s charted this year is one of a sole proprietor getting back to basics.
He runs a sports media operation. Sports stopped. But markets didn’t close. He saw an opportunity for Barstool and realized he needed to get this up and running quick, so Portnoy just did it himself. Just like he did when the business was just getting started.
And so now Portnoy is a financial pundit and seems to be having as much fun with stocks as he ever had with sports. Maybe more. But the spring and summer of 2020 are a reminder that the Barstool brand revolves around Portnoy, around the characters he plays and the characters that exist in that universe. It’s about a guy with a lot of energy and a feel for his audience giving people what they didn’t know they wanted.
And this on-the-fly entry into a new area of media, this rush of energy applied to a new opportunity, is a great lens through which to more closely examine another growing media trend that emphasizes the power of the solopreneur — independent newsletters.
This week, NPR’s Roben Farzad said the (incorrect) thing that many people are thinking.
This view is only correct because there are lots of Substacks out there now. (Hello!)
It is incorrect because you do not have to read them all.
Which is the point of the movement.
My consumption of newsletters has morphed into an after-the-fact binge. Rarely am I opening something that just hit my inbox. Instead of “reading the internet” at night by doomscrolling Twitter, I can now go into my personal, non-work inbox and catch up on stuff that I know is going to be interesting, long(ish), and probably not another version of why everything is bad. And it is definitely not news.
By now, just about everyone has read Kevin Kelly’s famous piece about finding a thousand true fans. I will not obligatorily recap the thesis. It’s right there in the title.
But Roben’s point about too many people starting Substacks is also wrong because of the Kelly thesis and the math we’ve all done in our heads: 1,000 subscribers at $100/year is a good living. Especially if you’re accountable only to yourself and your readers. (Plus, no meetings!) And in a world of 7+ billion people, finding 1,000 people who think you are interesting is not excessively ambitious.
The line from Kelly’s piece that I think about a lot is the idea that the most obscure node of a network is now just a click away from the most popular.
This new ability for the creator to retain the full price is revolutionary, but a second technological innovation amplifies that power further. A fundamental virtue of a peer-to-peer network (like the web) is that the most obscure node is only one click away from the most popular node. In other words the most obscure under-selling book, song, or idea, is only one click away from the best selling book, song or idea.
To use the financial newsletter space as an example, anyone can write a Substack that just one other person subscribes to. But if Matt Levine links to you, then you’re going to very quickly have more than one subscriber. All it takes is a single link to be discovered. In aggregator-speak, this gets the flywheel spinning. And the sum of all these obscure writers waiting to be discovered is larger than adding up all the big fish like Levine.
Etsy built a whole business on top of this insight. I suspect Substack sees itself as doing something similar.
And a dynamic that is even more bullish for the newsletter space is that traditional zero-sum media assumptions don’t apply to the internet. At least not strictly.
Your physical distribution area is no longer a constraint as it was for newspapers and magazines. A popular newsletter linking to a less popular newsletter doesn’t harm the leader but does help the follower. This is basically technology’s original promise — rising tides lift all boats when information is made free. (The overly simple reason everyone is so mad at Apple and Facebook and Google and Amazon is because they break this chain and renege on this promise.)
All of this is quite positive for the newsletter space. And indeed, it is an exciting time to have a strong thesis for a single operator media business. All you need to do is sign up for Substack, open a Stripe account, and you’re pretty much ready to go.
But figuring out the competitive dynamics and incentive structures for a new industry is the easy part. The hard part is actually doing the work. The hard part is actually writing.
Which brings us back to the Portnoy pivot and the long road ahead for this exciting moment in the media business.
For any new project, pure adrenaline keeps the work smooth for a while.
Maybe a few days, a few weeks, or a few months. Then reality sets in: the work is never going to be finished.
The apparent limitation of the ad-supported media business model is that there will never be enough traffic to satisfy the beast. But while subscription revenue is stickier and gives creators more runway and short-term security, eventually the flame that started any new project will be extinguished. A new muse will need to be found.
Portnoy, for instance, has gone from Boston sports, to all sports, to sports betting, to pizza, to the stock market. His success has taken many forms over the last 17 years. What this means for myself and everyone else in the early innings of a newsletter project is that whatever we’re doing right now will eventually have to be reinvented on the fly or abandoned altogether.
When I started this project, I figured I’d be so invigorated by the independence that I’d want to leave my job and write this letter full-time. Working for yourself, the dream! And, sure, I still think about this. Who knows what the future holds.
But more often I’m reminded of the classic Startup L. Jackson post about how to get rich in tech. And while no one working a job in media is doing it for the money, Verizon does pay for my health insurance and has a 401(k) match. In this environment, these are great luxuries. I am thrilled to have them.
The solopreneur evangelists tell us that these practicalities will eventually fall into place if you just do good work. The logic of a thousand true fans also supports this view. But the leaders in the passion economy show us that it takes a certain kind of creativity, a kind of transmutable enthusiasm across genres to make these projects work beyond the initial burst of energy.
And what Startup L. Jackson’s post really outlines is what going it alone doesn’t offer. Which is anything to fall back on when you’re in a rut, when it seems your good material has dried up, when you just want to mail it in for a quarter or two while you work out whatever it is that seems to make work a drag.
Very few creators, of course, will turn out like Dave Portnoy. And, of course, you don’t need to — there is lots of space between making a solid living writing on your own and selling your website to a publicly-traded gaming company.
But his arc will ultimately be familiar to anyone who stays in this game for a long time. Again, Portnoy had sold his company and had made millions of dollars and still he was the one who jumped in to create a new vertical in a pinch.
So wherever it is your newsletter is supposed to be going is not where it will end up. It is trite to say this. But also: it’s true. Don’t forget it.
Because eventually, the road will fork and it’ll be time to go all-in on whatever your version of day-trading in a pandemic happens to be. And you’ll have to do it alone and trust your thousand fans remain true.
Make sure you bring a hammer.