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Podcast Notes: John Skipper and the early days of ESPN.com

April 4, 2019

The Bill Simmons Podcast: “Catching up with John Skipper”

Great episode with Simmons and Skipper giving an overview of their careers working together in sports media. One theme that comes up a few times is content formatting.

This includes when they first worked together during the dial-up days of ESPN.com. John Skipper says he came in thinking the site should be treated more like a magazine (around 17:30):

John Skipper: It had a couple of people running it. It wasn’t going great. Actually it wasn’t very good. It was sort of HTML text and, you know, it did scores.

Bill Simmons: The entire internet was pretty bad back then though. It’s not like anyone was running away from the pack.

John Skipper: No everything was ugly. Everything was ugly. I do think one thing that John Walsh and I brought to it was a magazine sensibility. I immediately went in and said we’ve got to have photographs and we’ve got to have typefaces and we have to have layouts so the thing looks good.I was met by a bunch of guys who came in with data and said, “You know how long this will take to load on dial up?” And I’m like, “I don’t really care.” I said they’re gonna figure out that technological problem out at some point. And we’re gonna win because it’ll look great, we’ll do photographs, and we’re gonna hire good writers.

Simmons mentions that Grantland was designed for desktops — I always loved the layout of this Grantland piece: “One Hundred Years of Arm Bars“. It’s fine on mobile but it’s so cool on desktop. They talk about how written content on the web transitioned from desktop to mobile and how live broadcasting is making that transition.

Don’t overreach — John Skipper: “You just keep getting bigger and bigger. And the company was extraordinarily successful financially. It was in people’s lives. We’re starting new channels. And overreached in a couple areas. People don’t really need to eat at ESPN. That was a bad idea, ultimately. You don’t need to eat there.”

Okay, sometimes overreach — They also overreached creating the ESPN phone (The Sanyo MVP). However, some good things came out of it. They built new infrastructure for the network that the phone ran on, which set them up nicely moving into a sports world that was delivered digitally more and more.

It’s over an hour and they definitely touched on plenty of other great topics:

  • Buying up all the live rights to pretty niche sport events (live sports remain valuable in the on-demand streaming world)
  • Content strategy (30 for 30 cost $500,000 per episode / $15M total but it was entirely worth it so that HBO wasn’t the only place for sports documentaries)
  • The ups and downs of success (the jobs that are most fun aren’t likely to be when you’re responsible for the biggest group of people — but fun isn’t the only factor in a good career)
  • Professional relationships having their ups and downs (Simmons and Skipper step through their falling out and what they would and wouldn’t do differently)

(I always enjoy listening to Simmons talk about his early days on the web. Check out this earlier post for more.)

  • Weblog
Bill SimmonsJohn Skipper

F04: Walk, Listen, Talk — “Digital Minimalism”

April 2, 2019


In 2006, Cal Newport released a book called How to Become a Straight-A Student. Here’s an excerpt about procrastination:

That little procrastination devil on your shoulder is an incredible salesman. If you give him even a glimpse of an alternative to your work, then he will close the deal. To neutralize this devil, isolate him.

In the 13 years since then, that devil’s feasted on our attention and become more powerful. We also decided it’d be great to carry him around in our pockets and check in like every 7 seconds.

The latest solo episode is about Newport’s latest book, Digital Minimalism. His previous books have been pretty influential for me. So Good They Can’t Ignore You changed how I viewed careers. (“Follow your passion” works great if you excel at your passion and it involves valuable skills. You’re going to have to put the work in.) Deep Work changed how I block time off each day and how I set up my environment for getting work done.

Room 1: Kitchen with a Las Vegas buffet set up

Here’s a summary of what digital minimalism is:

Digital Minimalism A philosophy of technology use in which you focus your online time on a small number of carefully selected and optimized activities that strongly support things you value, and then happily miss out on everything else.

If you’ve read Deep Work, you might remember his description of the farmer and his tools. If there’s some value in a tool, that doesn’t automatically make it worth the cost. For a farmer, there are more things to consider than just the monetary cost of a tool. The same goes for how you use technology. Assuming these things are pretty much all free, the cost is your time, attention, and energy.

I get a lot of value reading subreddits about government policy and educational reform. Ok so it’s actually r/NBA and r/MMA. The content there is entertaining and pretty self-contained. There are highlights and I’ll check out a few of the top comments and then I’ll get out of there. I try not to get too sucked into reading too far into the comments.

I try avoiding anything that presents a bunch of articles. Not that I don’t think the content is good. It’s really just too much of a good thing. There’s always going to be a handful of links to open up if I check Twitter and then a dozen if I open up Hacker News. If I read all of that, it’s an hour lost. If I see all of that and don’t read it, it’s a little more FOMO to carry through the day.

Instead, I’ve created an echo chamber in my email inbox that I’m addicted to. I’ll work on that, but let’s move on…

minimalists don’t mind missing out on small things ; what worries them much more is diminishing the large things they already know for sure make a good life good.

Alright so you see the prime rib at the other side of the buffet. Someone’s carving it up and passing it out. Actually he’s going pretty fast. It’s toward the end of the night so you know it might be the last few juicy slices.

But you stop at each station on the way there to grab like a mini slice of pizza, a scoop of pasta, a couple pieces of spicy salmon. Hey there’s a charcuterie station.

Of course, the prime rib station closes.

Should’ve gone there first.

Fill your plate with analog interactions. Put the effort in to schedule and spend time with people in person. Make time to call people. Live across the country from a friend? Start a podcast with them even if you have no listeners!

Room 2: Living room filled with smoke, cigarettes, and your friends

Newport talks about technology being addicting.

Addiction is a condition in which a person engages in use of a substance or in a behavior for which the rewarding effects provide a compelling incentive to repeatedly pursue the behavior despite detrimental consequences.

Look at all these kids on their phones all the time. Actually look at everybody on their phones all the time. (Thanks to The Big Picture, you can see this around the world.)

I’m addicted to my phone and have thought it’s a bad thing for a while. I’m guessing some people know they’re addicted to their phone but don’t think it’s a bad thing. And then there are probably people who don’t think they’re addicted to their phones.

If you’re at least aware you’re addicted, you’ll find a ton of value in Digital Minimalism. If you don’t think the excessive technology use is bad, it might change your mind a little bit. If you do agree it’s bad, then the tactics in the book should help. (Intermittent fasting, but for your phone.)

Room 3: Swimming pool filled with bells, chimes, and broken glass

I sort of skipped explaining why I put broken glass in the room for this memory palace. It was to represent our shattered attention.

The urge to check Twitter or refresh Reddit becomes a nervous twitch that shatters uninterrupted time into shards too small to support the presence necessary for an intentional life

All the distractions throughout the day make it challenging to be intentional. Deep Work opened my eyes to just how fractured my attention was. (And still is.)

I had a classmate in college (“Back in my days…”) that mentioned to the class that she’s addicted to her email and gets a twitch when she can’t check it. It seemed kind of extreme at the time. Now, an NFL team gives its players cell phone breaks.

Check out Digital Minimalism and I’ll now go and do things that are definitely not checking my email.

  • Podcast
Cal NewportDigital Minimalism

F03: Walk, Listen, Talk — “Linchpin”

March 25, 2019

  • Podcast

Podcast Notes: Jim Collins on rating your days (Tim Ferriss Show)

March 22, 2019

On the Tim Ferriss Show, Jim Collins talks about his spreadsheet for tracking days:

And so what I started to do is I started creating a code, which is plus two, plus one, zero minus one, minus two. And the other thing I put in — and the key on all this by the way is you have to do it every day in real time. You can’t five days later look back and say, “How did I feel that day?” And what this is, is a totally subjective “How quality was the day?” A plus two is a super positive day.

This is a good reminder that our memory isn’t all that great.

What’d you eat for dinner last Thursday? Are you sure? If you don’t have a system for either planning it beforehand or recording it afterward, you’re probably not sure.

This reminded me of something from Bill Burnett and Dave Evans’s book, Designing Your Life. In it, they talk about the Good Time Journal:

Bill was surprised that coaching master’s students, the students he likes and spends the most time with, was such a drain on his week. After journaling a bit on that subject, he discovered two things: (1) he was trying to coach in a bad environment (the noisy graduate studio) and (2) his coaching interaction wasn’t effective—his students weren’t “getting it.” Those two observations resulted in a redesign of his Tuesday-night class environment (he changed classrooms) and a shift in the coaching structure from meeting one to one with each student to coaching in small groups, so students could help one another during the interactions.

(If writing about a book is any measure of it being a favorite, then Designing Your Life is definitely up there. Wally and I talked about it on a podcast episode, I also mentioned it on our very first episode, mentioned the ‘bias to action’ mindset in another podcast post, and I mentioned it when writing about LeBron James conserving energy.)

Their scale of energy and engagement is something I think of often. However you score your day or activities, it’s good not to wait too long.

The surprising spots can be the most valuable. You can only find the surprises when your memory of something being positive contrasting with it actually being negative. (Or the opposite.) Those surprises act as good starting points for adding more of what makes your day better or removing things that are draining.

Then you can take your days from [puts sunglasses on] good to great.

  • Podcast Notes
Designing Your LifeJim CollinsTim Ferriss

Podcast Notes: Hasan Minhaj (The Dave Chang Show)

March 21, 2019

Check the full episode out: The Dave Chang Show — Hasan Minhaj on Comedy As a Conduit

Okay so I’m going to keep going with the memory palace gimmick that I’ve been doing in the solo podcast episodes. I’m going to start with text descriptions then I’ll draw them and see how that goes.

In the living room there’s a dinner party with Michael Jordan (in a Wizards jersey), Allen Iverson (in a Grizzlies jersey), and Shaq in a jersey but it keeps switching between the Suns, Cavs, and Celtics like the jersey is Shang Tsung — Dave Chang continues with great sports analogies. Hasan Minhaj says he misses just focusing on the craft sometimes since now he has to think about production and staff and has people on his show looking to him for direction. He asks if Dave Chang misses that and I thought Dave had a great response.

I often times feel like I’m doing the worst part of the job. And I have to be comfortable with that. Because I’m a dad at the age of 41 and I think that’s a good thing right now because I’m mature enough to understand the pros and cons and the trials and tribulations.

But for the most part, as a manager, as a growing business, I have to accept that I’ve already had my fun doing what I wanted to do. And now it’s time—much like maybe an athlete… you don’t want to be the clown that’s like, “I can keep on playing!” I have wisdom now and it’s accumulated to the point where I can distribute it out and make other people successful.

Continuing with the memory palace…

…glance over to the kitchen and there are a bunch of cooks sitting around the island chatting drinks — Dave Chang talks about how bad a manager he was early on. And that it took a while to realize and accept that the people that work for him probably weren’t saying good things about him. I like how he describes his goal as a manager now:

Dave Chang: You want to be the kind of manager or boss—when people have drinks and they’re talking about it and they’re always unloading their troubles—that they don’t talk poorly about you.

I mean, that’s a pretty good thing to strive for. I’ll try to remember that if I ever end up becoming a manager.

Ok moving through the memory palace…

…you take a glance through the blinds into the swimming pool and it’s filled with chickens —

Hasan tells a story about wanting to go to UCLA and deciding if he should go to UCLA (which he loved) or UC Davis (where his family lived).

This guy I ran into in the quad got in my head. I got scared. I grew up in a small town. I was on this big campus. I got shook. And I fucked myself over.

I remember the narrative I told a lot of people was like, “Oh my parents were really strict and they made me stay at home.”

It’s fucking bullshit. I fucking chickened out. It’s one of the biggest regrets that I had in my life. It’s not about what school I went to. It’s the fact that I psyched myself out. I didn’t lose on my own terms.

So that became a critical juncture. I’m like I’m never gonna be scared ever again.

Anyway, that’s the end of the palace. (And if you want another story, here are some cards I drew a few months ago when Hasan Minhaj was on J.J. Redick’s podcast.)

  • Podcast Notes
Dave Chang ShowHasan Minhaj

F02: Walk, Listen, Talk — “Moonwalking With Einstein”

March 18, 2019

Note from 7/20/2021 — Going back and adding posts for all the podcast episodes, just to be thorough. I want to revisit this book sometime because I think it’s one with lessons htat have actually stuck.

Memorization is underrated these days because you can look everything up. There’s something to being able to remember, say, 5 good ideas from a podcast you’re listening to without writing it down vs. remembering 2. Especially if the reality is that you don’t end up re-listening, reviewing, and writing notes for everything in your information diet.

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