The Death of Free Bill Simmons

The best part of college was access to something I never had before. Not drugs, not girls, not courses or books or parties. No, it was high speed internet access. My school had — for the year — the fastest internet connection in the country (or so new students were told).

It was there that I began to follow Bill Simmons’ work and was amazed not only that I could read him, but everyone with a website. Before college my access was limited to the local paper at home and a few national ones and the public library. At college it felt like I had access to anything.

From 2001 until he left ESPN in 2015, I read most of Simmons’ work. From mailbags to predictions to the long (and he was famous for long) articles. His Friday columns were as anticipated as the end of the work week and I was privy to the inside jokes without having to follow the links that explained them.

Simmons expanded from just writing to also podcasting in 2007. This timing was great because I had a new baby daughter a few months later. I would push her stroller through our neighborhood and bounce her to sleep as I listed to Simmons. After our baby food maker, the iPod was the next most valuable device in our home. As new parents can attest, having connections beyond your kids is crucial, Simmons was one of those connections for me.

Now Simmons is gone from ESPN and that doesn’t matter that much. His popularity grew on the internet — in part thanks to those accelerating internet connections — and he’ll thrive on any platform.

What I do care about is that Free Bill Simmons is gone.

That Bill Simmons has been enveloped by the folds of HBO and the new version will emerge will be behind a paywall. Like a Terminator rebirth, (See what I did there? Dropped in a pop culture reference in honor of the fallen Free Bill Simmons), he will be newer, stronger, and with an enhanced aura. The reason is twofold, successful advertising has changed and you can’t make people pay for something they think should be free.

The changes in advertising

Advertising has moved from a scattershot approach to one of data driven precision. Tyler Cowen was asked by Ryan Hoover what he might put on a billboard in NYC and Cowen said “nothing really.” To what extent does a billboard (sponsored tweet, blog sidebar, etc.) matter anymore? Cowen suggested that at a certain scale a billboard (sponsored tweet, blog sidebar, etc.) advertisement might might sense, but not for much more. Coke can buy the billboard and remind people to drink Coke, but will it get new people to drink it?

We see this online when someone like Christopher the Conquered was tweeted by Ryan Adams (who has 699K followers) guess how many sales he made from the deluge of traffic? Zero. Why? My theory is that people look who follow Ryan Adams don’t look for music suggestions as much as they look for backstage pictures or thoughts about songwriting. Twitter isn’t for selling things as much as it for sharing things.

Rewind to Simmons’ days at ESPN and even though he had sponsors, Subway and SeatGeek, they were in the middle of a podcast. This is the audio equivalent to the billboard. No one looks to the billboard to see what to do, but get nudged. No one listens to podcasts and thinks, you know what, I am hungry or I could go for some tickets. These brands (and more the former than the latter) were getting a scale effect for their brand, but not a conversation effect. The problem is the timing.

These things (sponsored tweets, podcast ads) don’t work because places like Amazon have trumped the old model. They catch you in the act of buying and then suggest more stuff to buy. This system will grow as mobile grows as well. If Starbucks can pay for location details and then pop into your Twitter feed as you walk by, then isn’t that more powerful than a podcast blurb?

Some people suggest that podcast blurbs work because it’s a captive audience (a billboard you have to see, a tweet you can’t skip). Unlike television commercials that people can fast forward through, a listener is often doing something else. They can’t fast forward through a commercial while they drive. Kinda. I know that the introduction to the Tim Ferriss podcast is 2–3 minutes and I fast forward through it. This seems too similar to television commercials and it won’t work in the long term.

All of this applies to printed words as well. Those college years searching for people like Bill Simmons to read also meant that I grew up with Google. After 15 years of searches I know all the tips and hacks and I know that I never click on the advertisements (except for results I don’t want, then I click to make the company pay. Take that Ticketmaster!). If you tracked my eye movements I’m not sure I would even look over that part of the screen. I’ve adapted to jump to the key parts of something. Much like the photography Rule of Thirds, I think about webpages in terms of where is the content I came for.

Even though the ads come up on pages or get read on podcasts, people quickly learn to tune them out. We get exceptional at things we do over and over again. Five thousand ads in a day is a lot reps to figure out what we should tune into.

The future of advertising is an expansion of the Amazon model. Broadcasting to everyone will continue to work for legacy brands (Coke) but it will not grow their base. For something to work well it has to occupy a relevant niched in a customer’s mind.

John Gruber’s Daring Fireball is a great podcast, but I can’t remember who most of the sponsors are. That said, he’s much closer to advertising well than not well. If I happened to need something (razors, back up plans) while listening something might click. I view his show (his brand too) as one that focuses on craftsmanship and so I endue those brands with that same ethos.

Does Bill Simmons have a niche like that?

The SeatGeek collaboration sounds good and I would love to know their numbers on conversation rates and costs. My guess is that they were decent for the industry, but how many of those types of sponsors could Simmons pull in? I could see a new movie sponsor his show for a week before a premier. Maybe a pay-per-view event. Maybe a new app?

This list is short and it’s why so many articles about the Simmons and ESPN divorce talk about the money. This is why we are going to have to pay for Bill Simmons.

You have to charge at the start

Do you hear that? That noise is the sound of podcasters around the world nodding their head in agreement as they struggle to row upstream to the Land of Profitability. That podcasting started out free means that people expect it to be free and only through a lot of work (see Dan Carlin as an example) can it become a profitable career.

Simmons and HBO are on the banks of a peninsula on the banks of the River Business on their journey to the Land of Profitability. Their boat, the Lady Subscriber is big enough for a journey like this and should navigate the waters safely. The only problem of the moment is the drag of barnacles on the hull. A pesky little creature known as the Endowment Effect.

Let’s jump ship from this analogy and see what this means.

People look at HBO and expect they’ll pay extra for the content, but people look at Bill Simmons and expect they won’t. How will these two things mix?

I think HBO should choose a tact that mixes the free with the paid. Bill Simmons is popular in part because he’s popular. His form is readily copied, but the brand Bill Simmons still draws in readers. If he’s not drawing in as many readers, then it’s not the same brand of Bill Simmons.

A compromise then is for Simmons to create some podcast/articles that are free and some that are behind a paywall. If he sold “season previews” or “award shows” episode/articles, that would set the tone that some things were free but some were not. If HBO decides to go all paid though I wouldn’t be surprised.

Economist Richard Thaler writes, to always set your regular price as your higher prices, because “removing a discount is not nearly as objectionable as adding a surcharge.” People don’t like it.

We can see this with another recent HBO acquisition, Sesame Street. The letter of the agreement is “R,” for “repugnant reception.”

Tim Winter, of the Parents Television Council said:

“In order to watch original episodes of the most iconic children’s program in television history, parents are now forced to fork over about $180 per year and subscribe to the most sexually explicit, most graphically violent television network in America.”

Ouch. Big Bird hasn’t taken a blow like that since Mr. Hooper died.

Winter is a smart guy, he knows that Sesame Street wasn’t made for free. He also recognizes that the same people, Sesame Workshop, will be making the same show in the same way. If things are the same, why was he so upset?

The stone in Winter’s shoe is the endowment effect. It’s the same stone that podcasters have been trying to work out. People get used to things being a certain way, and if they aren’t that way anymore they get upset. It doesn’t need to be just entertainment. Only a few years ago people were upset to pay baggage fees for flights.

HBO should make people pay for some part if not all of Simmons. They need to find some middle ground they could pivot from if things aren’t quite right but to error on the side of making people pay.

I could see some free content, but to make his podcasts and articles entirely free would be a big mistake. The move from ESPN to HBO created a new start for Simmons and HBO would do well to establish a pay-for-viewing model. Something tells me they have the ability to do this.

Advice for all parties involved

HBO and Simmons: Charge, charge charge. I say that as a fan who loved every Friday afternoon I got to spend with Free Bill Simmons. Those days are over and HBO should start out with a — fair — price to read and listen to Bill.

Possibly create tiers because of the endowment effect that plebs like me have. I would guess(hope) for a free column and podcast but don’t expect it to be like the buffett that ESPN rolled out.

It might also behoove HBO to roll Simmons into the HBO NOW package. People like “bullet points” on purchases like this. In cases of an upfront (monthly, annual, etc) purchase, most people view their subsequent consumption as “free” and that adds to the event experience.

For example, when skiers buy a six-pack of lift tickets they enjoy the slopes more than someone who didn’t. Anecdotally our family trips to the zoo feel free because we bought a membership.

CostCo and Amazon Prime memberships both function like this as well. I thought it was a great deal when I found out that as a Prime member I could read an ebook a month for free. For free! As someone who reads about a book a week this was certain to be a great deal. I’ve used it 3 times.

It’s why satellite radio and television give you abundant channel lists. They know you won’t and don’t want to watch all that. They also know that you do and will want to feel good about your purchase. The bounty of options lets them do that.

Podcasters: “In a sticky situation you are,” the master Jedi Yoda might say. Your best track is to begin to bundle options together — besides your podcast — and create some sort of channel of your own. Note, it has to be better. That means a longer podcast, a Google hangout, a private QA, something beyond. You can’t just slap a price sticker on something you had been giving away. Maybe for $3/month people get a bonus section of the podcast, a new article, and any e-book you write.

The more “bullet points” you can offer the better and the sooner you get people used to paying you for your work, the easier that selling it will become.

Marketers: I haven’t seen a marketing plan since my college internship with a minor league baseball team so this advice may be way off, but it’s what I see as a consumer.

I would begin to move away from advertising platforms in favor advertising people. Begin to build brand ambassadors like Evernote or Larabar. These authentic voices will do more to persuade people than cold opt-ins to your email marketing campaign.

The other thing is to create your own content marketing. Dan Norris has a book about this (I’m only partially through, but it looks well oriented) and it works. Look at the GoPro YouTube channel. Look at the Slack blog. It’s your story, so tell it.

SeatGeek specifically. What should you do? Capitalizing on seasonality looked like a good idea, but I think they went too broad. Rather than advertise with Simmons for NBA playoff tickets they should have gone to the markets the games were in — Cleveland, San Antonio, San Francisco, etc, — and done more there. The Fear The Sword blog for the Cleveland Cavaliers would be prime real estate if they could do something there.

They also have a great spot to upend Ticket Master — who no one says anything good about. If I were SeatGeek I would pull marketing dollars to buy event tickets to every #ticketmastersucks tweeter. Listen to the story of Kid Rock, and do stuff like that. Every Veteran’s Day game should have veterans there from SeatGeek.

Writers: Simmons began his career as a writer so what lessons can people who hope to write gain from him, present company included? Good question.

Simmons’ path began with a page on AOL after working at a local desk and through college. He got lucky landing at ESPN and then even luckier that Boston Sport succeed. Do not underestimate this effect. It was fun to read Simmons because he had a connection to teams that did well. Had it been Miami and not Boston this article would be about Dan Le Batard. This isn’t to say Simmons wouldn’t be good, of course he would be, but maybe not the figure that he is.

If his career combined new media + geographical success + hyper growth platform (ESPN) we might be able to create a similar mix.

A new writer hoping to emulate Simmons would have to live on the new conversation platform of Twitter (or whatever replaces it). She would need to hit either a geographical hotspot or sport vein (soccer or tennis or whatever replaces football). Finally, she would need to grow as fast as possible, and there won’t be any established brands that do this. It might happen as a contributor to something like Buzzfeed. Ultimately, like Simmons, she’ll be big enough she won’t need her brand.


Thanks for reading. If you want to tell me how I messed up, missed something, or made a good point, I’m on Twitter @MikeDariano. I also write the site The Waiter’s Pad where I breakdown podcast interviews to salient points. If you liked this post I suggest you start with the conversation between Mark Cuban and Zach Lowe.

For further reading about the explicit ideas here, check out Greg McKeown’s Essentialism and Richard Thaler’s Misbehaving.