“Ooo. That’d be fun,” I thought, “Except I’m in the middle of writing a book and have no time.” But then I realized that one of the great things about my approach to writing books is that it actually leaves time to write other things. And I’m not alone. The New Yorker recently wrote about Trollope:

…three hours a day is all that’s needed to write successfully. Writing is turning time into language, and all good writers have an elaborate, fetishistic relationship to their working hours. Writers talking about time is like painters talking about unprimed canvas and pigments.

And so, here I am, 4:05 PM on a Friday, feeling like the lord of the manor. All my daily goals are done. I have a few hours before I need to make dinner for my wife. And so, yes. Yes. I will write an article on how I write a book. The more I thought about it since Derek suggested it, the more I realized that the tips and tricks I’ve learned to speed the process are as important as the knowledge, creativity and hard work (“turning time into language.”) We can say that the tools of the trade are just pen and paper, but that’s like saying music’s tools of the trade are just a voice and an instrument. Tell that to Drake. Or Max Martin. Knowledge of the tools is vital, as is a mastery of habit.

Note: I am concerning myself primarily here with non-fiction books. This is because I have published one, written a second, and am working on a third. I’ve tried my hand at fiction, and while I’ve succeeded at novellas, I have yet to complete a novel. I’m going to keep at it. And while I’ve yet to succeed, many of the tactics I outline here made my last attempt so much more successful than my first, so I have a hunch that they are applicable to fiction, though it’s admittedly still a hunch.

Onward!

Write. Always Write.

In many ways, the process seems so straightforward. You’ll find a million quotes about how to write a book, and most of them revolve around the basic concept of “just write.” Write, and don’t stop. It’s like Douglas Adams’ maxxim that the secret of flying is to jump at the ground and miss:

There is an art, it says, or rather, a knack to flying. The knack lies in learning how to throw yourself at the ground and miss. Pick a nice day, the guide suggests, and try it.

The first part is easy. All it requires is simply the ability to throw yourself forward with all your weight, and the willingness not to mind that it’s going to hurt.

That is, it’s going to hurt if you fail to miss the ground. Most people fail to miss the ground, and if they are really trying properly, the likelihood is that they will fail to miss it fairly hard.

Clearly, it is the second part, the missing, which presents the difficulties.

The key to writing a book is to write. Or, rather, to write every day. I mean, sure. Yes, you can miss a day here and there. But you should strive towards writing every day. Fit it into your life. Make room for it. Make time for it.

There are many tools for this, but I would like to introduce you to just one: 750 Words.

My friend Buster Benson built this site, and I cannot thank him enough for it. It has literally changed my life. Now, I have always managed to write every day, at least for the last 30 years or so. The problem was that I always wrote for an audience. I wanted my writing to be productive. And it killed my writing. As much as I miss the old days of Livejournal where a wonderful, supportive group of online friends nurtured each other and their writing, the fact that I was writing for an audience stunted my writing. 750 Words is private writing. In this world of sharing too much, there are virtually no sharing features on 750 Words. You can tweet out that you wrote that day, and maybe a few stats, but that’s it.

The interface is free of distractions. The lack of an audience makes it easier to try new things, to ramble, to bitch and moan to just get the words out. There are days that it is so painful to keep writing that I literally write “I don’t know what to say,” or words to that effect, over and over until I am done. This will happen to you, too.

There are other days that I wrote something brilliant that came out of nowhere. Many of my best and most successful Medium posts, such as The Economics of Star Trek, and Life as an Arcade, started as 750 words entries.

This is an important point: it’s okay, after you’ve written, to share the writing somewhere else. The point is to have no agenda when you set out. If it turns out, great.

750 Words is part of my morning routine. I do my exercise in the morning, check my email, and do my words before I go through much of the day. In other times in my life, I have done it on lunch breaks, on long walks, or last thing in the evening. It can function as a journal entry, it can function as therapy. Sometimes I take a pause and use my 750 Words to write a longer email to a close friend that I know needs to be done.

And sometimes, when I am working on a book, 750 Words warms me up, much like a morning stretch. I might be stuck in the book and it’s bothering me. So I will pause and do my 750 words, and bitch about how I am stuck. Nine times out of ten, just writing about the blockage, rather than trying to write the book, will unclog the blockage.

Make 750 Words part of your life. Write every day. The site will remind you to do it. There are little gamification tricks to keep you incentivized to keep at it, and a nice community of writers who, while very much in the background, still inspire you with their diligence. It still needs an iOS app, but if you add the site to your home screen, it can pretty much feel like an app. Protip: Set the time zone setting so that the end of the day is after you go to bed, and not midnight, if you like to do late night writing like I do. I have my 750 words turning over to the next day at 4 AM my time.

{iOS/Android note}

You will find my comment about 750 Words not having an iOS app will be a recurring theme in this article. Many of the best writing apps are bound to the desktop. I suppose this makes sense, as many people still feel the need for a full-sized keyboard when writing. But I do think that as tablets and phones slowly replace our computers, this will change. The specific tools aren’t set in stone. It’s the habits and developing a workflow that are important.

Reading

When writing an essay, or a blog post (god, definitely a blog post), it’s often the case you can just bang it out without doing a bunch of advance reading. This is almost never the case with a book. The odds are very slim that no one’s tackled the topic you’re tackling. Even if you are writing an autobiography, a working knowledge of the various forms of autobiography is somewhat essential. My first book, Agency, was a book that took my twenty years of experience in the ad industry and offered concrete advice on agency management. It was, in theory, as much of a book of “just type down what you know,” as can be. I still had to read dozens of books to complete it. The point is, you are going to have to read.

The reading time for your book is separate from the writing time. You will need to do both every day. Typically you need to read the books ahead of the writing, though we don’t always have that luxury (new things are being published every day, and you will undoubtedly eventually experience the unpleasant sensation of someone publishing something super relevant to your book when you are in the final stages of editing.) Generally speaking, though, you want to do your reading before you do your writing. If you know the topic in and out, and have been living and breathing it for years, you may be able to start writing without doing additional reading. However, you’re still going to find yourself needing a specific quote, and it’s much nicer to have it on hand than to have to go dig it up and mess up your flow.

When you’ve gotten really good, you might get to the point where you’re writing one book, while reading books in advance of your next book. This is a pleasant sensation if you prefer to not live and breathe a single topic your whole life, but can also be distracting. I typically pick up a new topic in depth when I’ve reached the editing stage. Or, well, I aspire to. Hasn’t quite worked out that cleanly yet.

Analog v digital

Various people have various opinions on reading paper books or kindle books. These biases are going to accompany you into this project. This is okay. However, you should prepare yourself now for having to read documents & books in both formats, regardless of your preferences. And you’ll need to develop a workflow for each format. Some books are only available on paper. Some books are $100 if you buy the one copy on Amazon of that 1912 out of print book, but are free in Google Books.

Books, Research Papers, Articles

You’ll also be reading many different types of documents. This will necessitate different workflows. For example, I prefer, when possible and affordable, to read my books on the Kindle. However, when reading a scholarly paper from an academic journal, I typically receive these in PDF form. These are much harder to read on the Kindle, and not only that, I can’t take notes or highlight in the same way. You will need to develop a workflow for each type of document.

Note Taking & Highlighting

From all of this reading, you are going to need to draw quotes, and remember what was in that book. When I first started, I made the rookie mistake of thinking that I could do all of this in my head. You won’t be able to. Assume from the beginning that everything you are reading will be forgotten. Learn to take notes. The important thing when finishing a book or other document is to make sure that when you’re done, you have marked up the document thoroughly, so you will be able to quickly find anything you need in the future.

The old fashioned process for note taking was to use a pen or a highlighter, highlighting passages and taking notes in the side. I still find myself very (occasionally) doing this. However, for me, I prefer to have these notes digital as soon as possible since, as you will see, the goal is to get all of them into a digital form as quickly as possible.

This can lead to some absurd situations. I take pictures of the screen of my Kindle. I take photos of books. Whatever it takes.

It’s important that all of these notes and highlights end up in one place. In the old days, when I was a kid, that meant note cards for each note and highlight. These days, for me, it means Evernote.

Evernote is the grand central station of book organization. Everything you are going to put into your book can and should go into Evernote (or some other equivalent product — I’m sure they’re out there, but.. Evernote!) Evernote works on desktops and mobile. This makes me prefer Evernote over the powerful book writing tools we’ll talk about later. Evernote is highly configurable and customizable.

The first important thing to do is to set up several notebooks in Evernote, where you are going to store your notes. Notebooks in Evernote can nest, so you can have a folder for your entire book project, with various notebooks. It might look something like this:

From here, it’s simply a matter of making sure that every note goes into the right notebook. Let’s walk through a few workflows to get there:

For Kindle books, I highlight and take notes using the internal highlighting and note taking tools built into the Kindle and Kindle apps. I then use the Kindle desktop app for Mac, open up the book, and go through my highlights:

I copy each highlight, and paste it into its own Evernote note. Note: this is kind of nice, because when you do it, the Kindle App helpfully appends a source to the copy and paste:

Note that the Kindle helpfully pastes an attribution, along with the page number. Also note that you can plug your Kindle into your computer, and grab an .XML file of all your highlights. You could theoretically find some automated way to do this into Evernote I suspect, but I do it manually because a) I’m not that tech savvy, and b) I often find that notes and highlights may go into different notebooks.

For PDFs, I use an app called iAnnotate on my iPad, or just the Preview app on the Mac, to highlight portions of PDFs and to make notes on them.

I use Dropbox for all the files related to my book, and sync it between my computer and my iOS devices. iAnnotate allows me to take a PDF out of the “research” or “to read” folder I have set up alongside my book, make edits, and save it back to that folder. From there, I can quickly scroll through the PDF on my desktop, and copy out any highlights and notes into Evernote. I SHOULD do this immediately upon finishing the document, but at least even if I forget to, when I go back to the document, all the important bits are highlighted and my notes are right there.

For articles on the web, I use the Evernote plug-in for my browser. Gosh, is it great:

Find an article, click the Evernote icon in your browser, and you’re confronted with a whole range of options. One thing I love is the “simplified article” setting, which strips away all the crap and just gives me the article:

You can also select the notebook you want to put the article in, and add tags. And, best, because this is an article from the web, Evernote will keep the URL and title, making citation easy.

Paper Books and magazine articles are undeniably the most difficult to get into Evernote. The main challenge for me is to get the note quickly into the digital space, without disrupting my reading and thinking. I have two approaches. First, I may read the book with a highlighter or pen, marking up the book as I go along. i.e., the old school approach. After reading it, I go back and transcribe the notes into Evernote. There are several things that suck about this. First, you can’t do it to library books. Second, you need to have a highlighter on your person. I don’t always have a highlighter on me.

But you know what I do have on me all the time? My phone. It’s time to introduce you to my favorite little app, jack of all trades, best buddy and home screen denizen: Captio.

Captio is an app that lets you rapidly email yourself something. That’s it. Deceptively simple. But so powerful.

First, you can email photos. So when reading a book and I stumble upon a highlight, I can whip out Captio, take a picture of the relevant passage, jot down a quick note, and email it to myself. This is wonderful.

And getting these notes into Evernote is a breeze. Because you can set your Captio up to email automatically into your Evernote. Oh my god, it’s the best. Here’s what I do. Following these instructions, I set it up so I can email into Evernote, going into a default notebook. Then I set up Captio to email to that address and my personal email address. I do this through a quick Gmail forward hack. If I only used Captio for emailing myself notes from paper books, I wouldn’t need to do this, but turns out I use Captio for everything. (Thanks to Michael Galpert for telling me about Captio years ago. Seriously. It changed my life).

You can also set things up to automatically tag the notes, but I don’t bother. I just have all of my Captio notes sent directly into evernote into a notebook called “Random Captio Emails,” and then occasionally parse it, placing the notes into their various appropriate folders. This is such a powerful life hack. More on this in a moment.

Best of all, you don’t need to carry a highlighter, there is no transcribing (until later, and then only if you’re directly quoting the source), and you don’t mark up your books. My condolences to future historians who have relied on personal, note-riddled copies of books for autobiographical source material.

I also use this technique for paper magazines.

People who value simplicity could well point out here now that I could also use the Evernote mobile app to take my picture and notes, and bypass the Captio step here. That is very true. This step also has the potential bonus of allowing Evernote to use its text recognition technology to do the transcribing for me. The reason I don’t take this approach is because I value Captio’s rapidity. It lets me go right back to reading within seconds. Evernote mobile is a great app, but it is harder to create on it than the desktop app, which has many wonderful features such as a distraction-free writing mode. However, I find it very time consuming to open the app, select new note, assign it to a notebook, click on the photo, click on the document-scanning mode, and take the photos. Captio gets me back to reading more quickly, which it my nominal task at this point. Your mileage may vary.

Don’t Forget the Book Report

I have also learned that the best thing to do when finishing a document is to immediately write a quick book report on it. I do this in my 750 Words the day I finish the book. Oh, dear god, I wish I had done this sooner. It is the best. If you’re dilligent in this one thing, in many cases you can have a third to half of the book done before you even begin. Trust me, it is glorious.

Do this as soon as possible. Preferably within a day or two. Don’t bother to look too much at your source material, or mine it for quotes. Just get your thoughts and impressions down. Do it like you were telling a friend. Don’t worry about “book voice.” By writing down your pure, unfiltered thoughts on the topic, you’re getting your point of view about the work. Not what other people want you think, and not what the book says itself necessarily. This is original work!

Creativity and Inspiration

We’ve tackled how to consume and parse third party material, but there’s also your own thoughts and material to contend with. This really comes down to two parts: getting your thoughts down to paper, and getting them organized. Let’s tackle the first here.

Even when we know a subject well, it is often hard to remember everything we know about it. When starting to write Agency, I first tried to just write down everything I knew. Seems simple enough. Turned out that even a year later, as I was finishing up the editing, I would suddenly remember a whole topic I hadn’t mentioned that was important for the book.

Thoughts are going to hit you all the time. I often think of a thing I need to get into my book as I’m falling asleep, cooking or on a walk. These are important to get down right away. It’s easy to think that it’s so important you will remember it, but you won’t, and few things can be as frustrating.

(I should pause for a moment to say that Evernote has a wonderful line of paper, analog notebooks in partnership with Moleskine that could, theoretically, provide as flexible and awesome an interface as my Captio-to-Evernote workflow. I haven’t tried them. But I always mean to. I guess that’s the evidence in itself I don’t need them. Because it’s just another thing to carry. It’s another thing to have on hand when the moment strikes. Also, we are writers, we use words. And I can type words. I can see the Evernote-Moleskine combo being hugely useful if you are in a visual medium. Our goal here is to get words down. )

Again, Captio comes in handy here. Have it on hand all the time. When in the thick of writing a book, I send myself literally a dozen notes a day. This morning, while on a walk, something hit me and I jotted down a 200 word Captio note. I felt awesome when I started today’s writing having that head start.

Walk walk walk

On that note, go for walks. Get away from the computer. Do things. A book, no matter the subject, is an expression of creativity. Creativity does not only happen in front of the computer. It happens at the movies. It happens in the kitchen. In the bed (bom chicka wow wow). Be ready to get it written down the moment it happens.

There exists, of course, the risk that you’ll spend too much time on the “creativity” and not enough on the writing. But this is where routine comes in. We’ve touched upon this with our 750 Words habit. We’ll expand upon it when we get to targets.

When spontaneous words become books

We should also point out that our 750 Words habit, even during the research and discovery phase of a book, can yield whole chapters of a book. If the mood strikes you one day, and you’ve written on the topic of your book (as opposed to about your day, your love life, or how hard it is to write — a surprisingly popular topic I’ll wager), copy and paste it out of 750 Words and into Evernote.

Organizing & Outlining

Once you’ve read all your source material, and captured a large amount of your own personal thoughts through inspirations tapped into Captio, unexpectedly genius spontaneous 750 Word entries and the like, it’s time to get everything organized.

Of course, in a way, everything is organized, in Evernote. In a way. But now we take it to the next level. It’s time to outline your book.

It is here I introduce you to a new piece of software I couldn’t live without: Scrivener.

Now. Before we go any further, I need to warn you that Scrivener is only a desktop app. Their attempts at developing an iPad app have been long and miserable. It is really sad. The company is getting close to being completely moribund. This may matter to you. What I have found is that for me, the need for an iOS version of Scrivener is more academic. I rarely write on an iOS device, and when I do, I write right into Captio, sending it to Evernote, or I write my 750 Words. However, I am a well off dude that owns, like, 6 Macs, and has been typing on a full sized Apple keyboard since 1983 or so. Some people can’t afford a full Mac. And some people are more comfortable typing on screens, or mini keyboards, than I am.

If these are concerns of yours, there are two up-and-comers who you should consider. The first is the aforementioned Evernote. They seem to be working very hard at turning Evernote into a viable option for book writing. My friend Nicholas Carlson wrote his whole book directly into Evernote. The second is Storyist, which is essentially a new version of Scrivener that actually also has an iOS version. Storyist also seems to be a bit more robust if you are writing screenplays.

I stick with Scrivener because: a) the current book I started was 3 years ago and this wasn’t an issue as much, b) Evernote is built for so many people doing so many things that they are very slow to iterate on longform-writer specific features, such as Kindle export, and c) I can’t live without targets (more on them later). For my fourth book, I will probably move over to Storyist if Scrivener hasn’t come around. I’ve also had a hankering to try a screenplay out, so all the better.

All that being said, Scrivener is still awesome. If you had visions of writing your book in MS Word or Pages, give them up now. While Scrivener has many strengths, one of them is in content organization. It’s so good, that there have been times I have thought about abandoning Evernote completely. Scrivener has many of the same organizing features (including great web clipping organization). But in the end, Evernote is a large, iterating company, and Scrivener isn’t, so… I use each tool for their speciality. I, along with many writers, dream of one tool to rule them all, but I suspect it’s a long way off.

Anyway, Scrivener’s organizational tools are superb. Note cards, outlining, everything you need. Lots to learn. I have spent hours of my life watching Scrivener tutorials, but it is so, so worth it.

Whatever tool you use, the goal here is to outline your book. At a minimum, make one document for every section. Not every chapter, every section. The more granular the better. All of these tools allow for nested documents, and include folders. In the end, you want your outline to look something like this:

Outlining is vital. You want to break it down so every section is (not coincidentally) 750–1,000 words. You’ll find many of your outline topics from your inspirational Captios, such as “don’t forget to write about x.” Go ahead and make X a section. Make major book reports sections. Make anything you can think of it’s own separate section. Keep adding them. You may kill a few later, but add all that you can think of, for now, and then organize them.

This does two things:

1. It decouples the act of writing a section from deciding where to put it. You will change your outline hundreds of times. That’s okay. When you do, the work that you have written will move with it. Yes, you may need to tweak transitions here and there, but your writing will still be intact.
2. It breaks down each larger section into smaller, more easily writeable chunks. This is the first, major break in transitioning from thinking of your book as one long document to a series of smaller documents.

This is huge. The importance of this cannot be overstated. A journey begins with a single step and all that yang. No one can look at a blank paper and start writing. Actually, I saw that happen once in a documentary. A famous screenwriter had finished his film and he sat down to start the sequel, and typed out the name on a blank piece of paper, like he was gonna write the whole thing in order. You know who that was? George Lucas. Revenge of the Sith. Do not let this happen to you.

Writing

While this whole article can seem like an exercise of walking in circles around the prey instead of attacking the prey, that is exactly the point. The prey is much, much bigger than you. You need tools, you need weapons, you need to study it, be prepared, and find its weaknesses.

Then we attack.

Setting Goals and Targets

At this point, we write. We write a set amount each day.

And, truth be told, it’s not much. Let me introduce you to another vital feature: Project Targets.

These are the best! Here’s what you do. You set a deadline, you set a word count, you tell it what days you want to write, and a few other things, and Scrivener automatically tells you each day when you hit your goal. It is AWESOME. It gives a little beep each day when you’ve hit your target and it is the best feeling in the world.

If all has gone well, you will write one section of the book per day, and those sections will be about 750–1,250 words. It will never align this perfectly, but those are good guidelines.

On a good day, when I’m hyper and productive, I can hit it in 30–40 minutes. On a bad day, when I have NOTHING, I can hit it in a couple of hours.

So, yes. You can write a couple hours a day and finish a book in no time. Look at my targets. I started this book, in earnest, about 3 weeks ago. I want to finish this draft 10/1. It’s not bad at all. I also set my target for 100,000 words even though I’m writing an 80,000 word book because I want to leave room for editing.

That’s all you need to write in the day. Sure, there are times when you find yourself on a roll and doing much more. This can be good. I find that it’s not always good when writing non-fiction, as often what is actually happening is you’re writing parts of other sections of the book and you’ll have a miserable time merging them later, when you write that section. With fiction, I find that an inspirational bout of writing a lot more is almost always good. Roll with it. But don’t sweat it if it doesn’t happen.

Find a Routine

So, a typical writing day for me will look something like this:

• I wake up, have a quick breakfast, enjoy the morning for 30 minutes.
• I go on a long walk. I listen to instrumental music, mainly, from a Spotify playlist I have of “writing music.” (I warn you some of it is noisy). I look at the trees. I people watch. I write notes into my Captio, some about the book I’m working on, some not.
• I go home, and I do my email and whatever else needs to be done for my part time day job.
• I write my 750 words.
• I write my words for my book. Sometimes, my 750 words all but did this for me. Other times, this can take a few hours.
• I do other things. I read, I cook, whatever. I read before bed, on trips, and if a day goes so perfectly I finish everything else early.

Lest ye think this is the life of privilege and leisure and oh man how can you do all that without a job, this was my routine while holding down a job as a very busy internet executive:

• I woke up around 7:30, I got to work around 8:45. I took notes on the subway, and read on the subway.
• I worked all day.
• I wrote my words for a book during my lunch break. It was a very short book — 50,000 words. I needed to do about 750 a day. I used the organizational techniques here, which I laid out in advance, on the weekend, so all I had to do was get my words down in my break.
• I walked home, which took about 45 minutes. I cleared my head, thought about my writing, and took lots of Captio notes.
• I made dinner, and did my 750 words after dinner.

You can find a routine. I have friends who have three kids and still write books and hold down jobs.

Editing

Once your book is done, you will need to edit it. I believe editing deserves its own post, but I will say a few words here:

I believe it’s better to over-write than to under-write. Cutting your work can SUCK, but it’s better than not having enough.

I export the whole book to PDF from Scrivener, and then use iAnnotate to read the book, highlight, mark edits and changes, and comments and notes for myself. I do this at least twice before I let anyone else read it. It can suck, because once other people are in the equation, your book can still radically change, and you’ll think “why did I polish it that much before I gave it to someone else?” But I still feel it’s the right thing to do. Better to show people something more polished. I hear stories all the time of people who let people into their writing early, and I’ve just not had much luck with that. I need to get my vision down first. You may find a different approach is better.

Then comes the real editing, which involves usually, a ton of cutting, some painful re-writes, and at least one major re-organization. That’s okay. Because, through this whole portion I am just thinking “whatever, I’ve written this book. I did the hard part, I can do any of this.” Major re-writes can be accomplished via similar means described above. Major reorgs will occur to you on walks more than once. Eventually you’ll need to settle on one outline until you make final decisions with your publishing editor, if you have one. If not, you can do whatever the hell you want. Maybe ask a friend. Maybe not. It’s cool. Because you wrote a book. Congrats.

PS: It’s 6:45 PM. I also took a call in that 2 and a half hours. I wrote this today because my conscience was clear after a beautifully executed day of routine. It was a lucky day, they are not all that lucky. I will still have to edit this before I publish it, but… hey. It’s done.

PPS: And now it’s Monday, I’ve given this an edit, and tweaked about 5–10% of it. There are probably a load of typos, but I trust you guys will point those out for me.

PPPS: If you enjoyed this, I have also written a piece on My Reading Habits.

My Book Writing Habits was originally published in Rick Webb on Medium, where people are continuing the conversation by highlighting and responding to this story.

There’s a lot of work, it goes late. This is the old-school advertising all nighter, where there is still a paste up room where people can smoke. Storyboards are still being put on easels. There are six or seven people on the joint international team.

It’s an intense non-romantic, platonic work collaboration, between the man and the woman. The woman leads the French team, the man is simply a team member. The illustrator, perhaps. Something craftsmanlike, and grounded. Not an art director, not a manager.

The later it goes, wine and cigarettes come out. It is, after all, France. It’s probably the 90's. For a brief moment as things wind up, the whole thing descends slightly into a parody of a French version of Friends. Spirits are high.

After work, it’s nearing dawn. The job is done, and there is a sense of accomplishment and excitement. Also, unusually, there is not an imminent need to rush off to the pitch or the meeting. They’ve solved the problem, cracked the code, and their work is done. The team disbands, leaving the man and the woman, who are wrapping up, and heads out together.

They decide to take a walk, as they are nominally headed in the same direction. They walk and they talk. They knew each other by reputation and had met once before prior to this night, but were not friends. Yet as they walk, they realize that they have so much intimacy to share. Not romantic. Just… they each were, for the other, one of those people with whom you can share any feeling, be honest, talk about things you’re never comfortable talking about with the people with whom you are closer in life. They share deep dark secrets — not that either is anything more than a normal, fearful, complex human being. There are no murders or scandals, and only mundane betrayals in their past. They talk easily but intensely, aware it’s rare and magical, but not inferring anything more from it. Could someone actually marry someone like this? The magic go away, of course it would go away. Such honesty cannot withstand real life. They do not even consider such possibilities. They are too wrapped up in the moment, in the honesty they are exhilarated by sharing, and the agreement they feel.

They walk and talk into the early morning. The woman grows drowsy. They find a small cafe in the lobby of the office park within which they work. They have ended up making a large circuit, and are again standing back by the office. They have perhaps an hour until they need to be back at work. The woman falls asleep in her chair. The man covers her up with her coat and stands up, walks around. Smokes a cigarette. Taps on his phone.

Anon an agitated man comes rushing up to them. He wears a grey raincoat. It is the woman’s husband. He’s been looking for her all night. Did she not tell him she was working late? Is he possessive? It is unclear, but he is angry. The ad man explains they were working all night, points to the man’s wife sitting some yards away and says “There she is. She’s tired, but she’s fine. She will be happy to see you.” But the husband is having none of it. He rants and yells, threatens violence, finally attempts to physically intimidate the ad man by pushing him. The ad man is having none of it, and is well-versed in physical altercations. He rapidly and easily subdues the husband. He drags him over, sits him down next to his wife, and shakes him. He looks him in the eye and says “Your wife is a good woman, and nothing happened. Pull yourself together or your jealousy will consume you and you will lose her.”

As he finishes saying this, the wife wakes up. She groggily comes to and sees her husband. She smiles at him. He sees in her eyes that what the ad man says is true. He is ashamed, chagrinned. His wife beams at him and introduces him to the ad man. Says they had a long night of working and talking but that the work is done, and they feel good about it. That they must have the ad man over for tea one day before he heads back over the channel. The husband, embarrassed by his misinterpretation, but still somewhat sullen over the obvious intimacy between the two, endeavors to assent enthusiastically.

“Yes, yes you must come,” he says to the ad man.

The ad man is still somewhat flush from the rare exertion of physical force. He, too, is confused. Not because there was any temptation for physical intimacy with the woman. Indeed, if there were a temptation, and it was overcome, he would feel that his position was somewhat strengthened for having resisted some temptation. But he cannot claim in the moral court of his consciousness that he actually fought off any evil. Does that make this more or less innocent? He is unsure. He’s unsure if the extreme emotional connection he just experienced is acceptable or not, at a deeper, truer level. For he knows that every human, and every couple, have different ways of interpreting and incorporating these more ineffable connections. Some can handle it, some can not.

But he’s damn well not going to back down now. He catches the husband’s gaze and looks right into his eyes and says firmly “Yes, yes I shall come visit for tea. I would like that.” For all of the complexity of the ties between these three, he has made his decision. This relationship will be normalized. It will be returned to the plane of every day existence. It is the right thing to do, at this moment, even if the connection is never again experienced.

The husband catches his meaning. He nods, barely perceptible to the ad man, and passing unnoticed by his wife.

The ad man makes his leave.

The Paste Up Room was originally published in Rick Webb on Medium, where people are continuing the conversation by highlighting and responding to this story.

Essentially, Bataille states that the planet is covered in swirling eddies of excess energy, which know no human boundaries. These eddies are then harnessed by the labor of men, who use that energy to convert into food, buildings, what have you, through labor. Labor then produces currency. Boom. Economics.

However, these eddies do not swirl exactly evenly over the globe, and thus in some places and in some times, the eddies can be harvested and converted into materiel in greater quantities — indeed, in quantities greater than are needed to just feed and house society.

This excess energy (“the accursed share”), Bataille posits, will eventually destroy a civilization through war or indolence unless it is “burned off.” Here enters Bataille’s theory of the “Potlatch.” Bataille borrows the term from the Native Americans of the pacific northwest, where a potlatch was a massive, excessive, gift giving feast. The whole point was to show how wealthy your tribe was through gift giving and destruction of assets. Says anthropologist Dorothy Johansen, “In the potlatch, the host in effect challenged a guest chieftain to exceed him in his ‘power’ to give away or to destroy goods. If the guest did not return 100 percent on the gifts received and destroy even more wealth in a bigger and better bonfire, he and his people lost face and so his ‘power’ was diminished.”

Bataille painstakingly shows that this practice of pointlessly destroying your wealth was by no means confined to the pacific northwest native Americans. He offers up examples from throughout history — human sacrifices, the building of pyramids, etc.

Indeed, Bataille posits that the act of potlatch is central to the human condition, and you cannot understand economics from a purely rational point of view. You must include the concept of excess “the accursed share,” and the concept of the Potlatch — the non-rational destruction of wealth.

It doesn’t take a leap of imagination to place the Super Bowl in the provence of Potlatch. Forty million people waste the day doing nothing but stuffing their faces staring at an electronic box. Hundreds of millions of dollars are squandered through barely, marginally effective advertising, illusion-of-safety-based “security measures,” disrupted air traffic at one of the nation’s largest hubs, tens of thousands of over-priced hotel rooms purchased by the struggling, increasingly strained middle class, and excessive salaries for the players and producers of the event.

The important thing to remember is that to the average citizen of the society, unless you were the one being sacrificed in a human sacrifice, a potlatch can be a hell of a lot of fun. And the potlatch is essential to the smooth-functioning of an economy. For not only does it keep those resources from being spent on war, but, more importantly, it burns them up. It completely wastes them. For to do otherwise, the energy would stay bottled up in the society and destroy it.

So, go Pats.

The National Accursed Share League was originally published in Rick Webb on Medium, where people are continuing the conversation by highlighting and responding to this story.

Hey Donny -

Sorry for the delay. I have just moved down to Chapel Hill, NC, and been unpacking and setting up this house and haven’t been hitting the email much. Just now starting to get settled and back in front of a computer with any regularity.

Read your email, and you’re right. A lot of it rings familiar. To give you a quick summary, I used to play in bands, a lot, and was really making a go of it. Me and some other friends from other bands started a record label as a collective together — the Archenemy Record Company. It’s still around, but it’s really just kind of a hobby at this point. From there, I got into tech and advertising, and eventually started an agency, the Barbarian Group. Worked there for ten years, sold it. Loved it, but eventually left in 2011, and since then I’ve been working mainly in tech — consulting for startups like Tumblr, Soundcloud and Percolate. Lately, though, I’ve decided to pull back a bit and focus a little more on my art again — this time writing (hence the move to Chapel Hill). Not completely, but… more.

The thing about this path that makes it different from you is that we chose the exact worst time to start a record label. The CD market was imploding, but there was no robust online alternative yet. No Sound Exchange, no iTunes music store, no streaming, maybe a little internet radio, but it paid nothing. Our bands were decent and the label had good buzz, but it was so, so hard to make a go of it then, especially without any money to fund things for a few years as we got off the ground. Recently I read a history of an 80's English label, Factory Records. It all sounded pretty familiar until I got to the part where they decided how many copies of their first 7" single to make. 25,000! Can you imagine, in the 90's or 2000's, someone pressing 25,000 copies of a vinyl single? Hell, I’ll bet Taylor Swift didn’t make many more copies of 1989 on Vinyl. I mean, if we could have sold 25,000 copies of a single, we’d have done great! But by then, you were lucky to sell 1 or 2,000.

ANYWAY, because I couldn’t really make a viable go of the label, I decided to “get a job” and just “play in a band.” My friend asked me to start Barbarian Group, our agency, with him, and I thought “that’s a way to make some money. I’ll go back to trying to live off of my art afterwards.” And, so, 14 years later, here I am.

So… what do I think now? Well, I’m rich, so that’s nice. In terms of my art, though, I still feel like a dillettante, I still feel like it’s a hobby. I never did the trial by fire of trying to make a go of it no matter what, no matter whether I made money or not, and ajusted my living habits to those of a poor artist. Is that good or bad? I don’t know. I have friends who stuck with it, just kept going no matter what, and they all sort of eke out a living off of their music these days, which I find to be really amazing and impressive. Of course, they probably find my own accomplishments impressive, so who can say. The grass is always greener, right?

I’ll tell you another story. 1999. I was at SXSW. On a photo pass from a friend’s zine, one of my friend’s bands was playing a showcase. Another friend was down there tour managing another band. Our label was still going, but I had started freelancing in advertising to pay the rent. I wasn’t doing tons of work, but the money was insanely good compared to what I was used to. Me and these friends and some of their friends were all sitting at a bar at SXSW and eventually a few of them all started talking about how much money they made. These were like A&R people at major labels, stuff like that. They all made NOTHING. I mean, ridiculously low salaries. Like I made more in my 1–2 days a week working in advertising than they made. And it just struck me: Of COURSE they don’t make anything. EVERYONE wants to work in music, and they’ll do anything to work in the industry. You can never make a good salary working in music.

Since then, I’ve touched over to the music industry through the years. Did a bunch of work for Justin Timberlake for a few years, a bunch of work for Shakira. I would go with their managers to go meet people at the labels. At their web divisions. Etc. And you are 100% right. Well, you’re 90% right. There ARE a few smart people in the music industry, but the industry as a whole is SO DUMB because a) it’s institutionally set up to deny the reality of the internet and b) there are SO MANY dumb people who just want to work in music that the ratios are so far off that it’s impossible for the smart people to make a difference. And the smart people are usually either biding their time to get out, or they’re just biding their time till retirement.

Many people realize this, and typically people in your position upon seeing this think to themselves “well I will start some startup in the music industry and change it all and make a mint!” I confess I’ve fallen prey to this line of thinking a few times in my life. Here’s what I’ve found, however:

First, the exact same laws of supply and demand apply that applied when I was sitting at that bar at SXSW in 99. So many people want to work in the music industry, and so many of them have realized how broken it is, that they’ve all had the bright idea to start a music startup. SO there’s tons of competition, low valuations, etc.

Second, the music industry itself isn’t THAT big as industries go, so there’s not a ton of investor temptation for these startups.

And third, like many things, it’s an insiders game. Look at the big wins in music lately — Beats, Spotify. These things weren’t started by scrappy outsiders. This isn’t an industry where the young outsider can win big. Sure, they can destructively disrupt the thing (think Napster) but any money is gonna be made by insiders.

Reading your email, I think you’ve sort of hit the nail on the head. You seem to be at a crossroads. It seems to me you could go all in and give everything to your album, or you could let it take a bit of a backseat and go make some money and put that money towards your “art.” I can’t really answer that, but i do think it’d help you to decide which one is going to be your “career” for the next few years. Not necesarily forever, but for, say, the next 3–5 years. Are you going to be an artist, 100% all in, or an entrepreneur that has a hobby in art?

(The “investment” is a wrinkle I can’t advise on. It’s not clear to me what you took it for, from whom, or what they’re expecting. There’s a bit of a world of artists taking “investment” these days (Google “Jakob Lodwick and Francis and the lights”) but not much. I guess my advice would be to put the investment aside, make some larger decisions, then deal with the investors as necessary.)

Anyhow. It’s hard to look back on your life and ask yourself if you did the right or wrong things. I’m very happy in my life now. I know if I decided to go “all in” on art, it would be very different. Would it be better? Worse? I don’t know. I do know that there was no half-waying it, though. At that moment in my life, I needed to decide which path to took. I think the one I took has been quite an adventure.

I know this probably isn’t super helpful, but there it is. Hope you take something out of it.

r.

An Email to Donnie was originally published in Rick Webb on Medium, where people are continuing the conversation by highlighting and responding to this story.

Note: I wrote a post a little while ago that was a sort of rambling, personal, essay in the form of an email to a friend. Probably slightly-too-personal, and not very self-helpy. Really not the sort of thing that you’re supposed to post to Medium if you’re a go-getting tech dude. No rah rah, no promotion, barely anything from my current career. Just. Musing. It was kind of fun, so I’m going to do more of them. This one started out as a journal post today.

My whole life, my basic MO has been to get to know a field — a topic, a career — just enough to grasp its basic workings, and then I get bored. I’ve been doing this my whole life. I’m as yet undecided on whether this is a good thing, a bad thing, or a neutral thing. In my brief time in each of these fields, I’ve sussed out the basics and had some modicum of success, and then moved on.

The best analogy I can think of is being in a video arcade. You walk up to one game, and you try it out. Sometimes you do great, sometimes you die instantly in a minefield or a hail of alien bombs. When that happens, you deposit another quarter, and try again. You keep doing that until you get the gist. To extend this metaphor, I basically play the game until I can get on the high score list. Not the top slot mind you, just anywhere in the top 10.

Now, this is just one Asteroids machine of many throughout the world. Each one has a top 10 list. There is no real correlation between the top 10 scores on your machine and all the other machines. Your machine may have been reset last night, and only like 100 people have played it since, and the #10 score is only like 40,000. Somewhere else in the world, there’s an asteroids machine that’s never been unplugged since the day it was placed in that arcade in (Wikipedia tells me) 1980.* That game might have a high score of 1 million. And, of course, both of these scores are just the highest score on that machine. A theoretical maximum also exists. A perfect game.

I am not a perfect game player. I am a high-score-on-that-machine-and-move-on player. Now, some of those machines might have (relatively speaking) high scores across all machines, and some may not. So, by the time I’ve gotten on the high sore list of that machine, my skills in that game may be, like, nationally ranked, or just best-on-the-block.

Then, of course, there’s natural talent. Some of these machines I could walk up to and start playing and be preternaturally good. I might be a natural. A prodigy. I might get on the top 10 immediately. Now, I admit, when I encounter such a field (remember, this is a metaphor here), I tend to stick around a *little* longer. Maybe a few weeks, months or years. But in the end, the “browsing the arcade” metaphor holds, and I will move on from that field.

So, then. I may have gotten really good because the machine in my arcade had some really high scores relatively speaking. I got really good at math in high school because my school had some amazing mathematicians, for example.

Or I may have gotten really good at something because of some innate natural talent that I milked a little further. I happen to be very, very good at Ping Pong. No idea why. But once I got really good and started beating everyone at the student union, I just gave up and moved on, rather than, you know, pursue an illustrious career in ping pong.

This, to me, is a really interesting little nugget: you can get good at things for different reasons. Both of these reasons, you’ll notice, have little to do with “passion.” That’s a topic for another occasion, I think. We can safely limit ourselves here to a passing acknowledgement that passion probably influences which arcade game you step up to next: we’re not necessarily trying every single game in the arcade in order.

This is something I am just really coming to terms with about myself. I’ve known it for a long time, but I’ve never really thought about the ramifications. It was always obvious to me that this was the right approach. I’ve never questioned it. It’s only occurring to me now, really, that other people do not take this approach. That, maybe, leaving a career or abandoning a field or hobby right when you get good at it is a wee bit self defeating. I am undecided on this topic.

A few tableaux:

Yesterday: I was on a call with a portfolio company at the fund I work at. Their product is awesome, and they are, in bro parlance, crushing it. It’s a product related to one of my old fields. A field in which I managed to obtain some notoriety (I guess that particular arcade game in the gaming parlor hadn’t been unplugged in a few years). They asked me for intros and whatnot, and I thought to myself how I barely even talk to people from that world anymore. And I was SO INTO IT. For several years. But, like, in getting these guys’ update it was super clear to me I barely even know what’s going on with that field anymore, and I have lost touch with many of my friends in that industry. That was not a super great feeling.

Also yesterday: we had some dudes come to our new house to help us with some Ethernet issues. They saw my studio. All my musical gear. This has happened a few times now. The electricians. The movers. A couple neighbor kids. They ask if I’m a musician. I am currently trying to be a writer and an investor but there’s just one little computer and some books in the corner of my office for these particular pursuits because, well, they don’t take up as much space as keyboards and guitars. I never know what to tell these people when they ask if “I am a musician.” I know they really mean am I some sort of professional, and I am not. I gave that whole thing up, inexplicably, even though our band was really good and people went to our shows and we had fans and everything. But when that band encountered a few problems, I just moved to another game in the arcade. I remember knowing very well at the time that the problems were surmountable, but I also kind of knew this was pretty much it. If I kept going with the music thing, the BEST thing that could happen is I’d be drinking in night clubs even MORE often, and on the road with no money even MORE often and, also, I felt like the secret nut had been cracked, so, really, what was the point? Everything beyond RIGHT THEN was going to be… just… tactics. So I moved on. And now, in my basement studio, I just sort of dodge their questions. I say (not fully honestly) that this is the first time in years I’ve had it all set up and I’m going to play around again, so… “we’ll see!” (always end on a note of optimism).

A few days ago: my friend Doug and I were on a good weekend vision quest in fields of mud. At some point in the weekend he asked if I would ever “take a job” again.† I didn’t waste much time before I said “no way.” What’s the point. I had jobs. I was good at them, I did well. But the same things happen each time.

This calls for a bit of a tangent:

There are two currents of my personality that intersect, but are not as related as they seem to be:

First, I’m terrible at keeping my head down. If you’re not a leader at a company, just a regular worker, it seems to me in 90% of corporate America your success is at least partially defined by your ability to keep your head down. Hunker down, ride out the absurdity, and don’t get too involved in the bumps and scrapes of the every day drama. And I am just not good at that. I sometimes envy people like that, and I’ve occasionally attempted to get better at it, but I’ve had to come to accept it’s just not in me. For better or worse.

Secondly, I’ve had a temper my whole life. It’s much better these days. There hasn’t been an “anger bagel” incident in years (long story). The Webb Advisory hasn’t had an emergency update in three years and counting. I’m trying, getting better, and keeping my mouth shut. But I’ve never been especially good at it. Lately I’ve learned to control my temper by doing what I think is hugely responsible and adult — just getting out of the room. So I walk out when things get tense. Apparently that is still a pretty dramatic, annoying thing, when people get upset and just walk out of the room. But for me it’s such a hallmark of maturity.

In any case, both of these elements make it hard to work a regular job in a non-leadership position, I was explaining to Doug. Because you want to do right, you want to participate, so you try and help and say something when you think something’s off track. I still believe it’s the right thing to do. But many, many people don’t want to hear it. So they tell you to shut up, which kicks in the temper, so you walk out. Two separate habits, but lethally intertwined.

ANYWAY, I was explaining all this to Doug, when it struck me: this is actually related to my arcade approach. Doug is a polymath too. Even ignoring the arcade thing, we read books on millions of topics, explore different things, get obsessed about all sorts of things. We don’t fit into the usual “engineer” or “product designer’ roles. We have opinions on all aspects. And there’s really only one place for polymaths in companies: leadership.

Now, some great leaders manage to harness polymaths in their organizations. I’ve had a few bosses like that, and I am forever in their debt (thank you, Derek).

And there are some polymaths that are able to compartmentalize: I know I am a decent designer, too, but they want me for my back-end coding chops, so I’ll just park the rest outside. I’ve not been able to do that in my life. Spoilt by too many years in leadership, when it was a trait that was important to build. Too much experience knowing that all fields, all bodies of knowledge, converge and are useful. The realization that I am blocking much out only to be a cog in a larger machine is, I suppose, too much for me. I guess, despite my best efforts, I’m too individualist? No, that’s not it. It’s because I’ve learned through the crucible that I’m not as helpful to the greater whole playing that of a limited-knowledge cog.

So, then, I suppose the arcade approach to life has its pros and cons. It turns you into a polymath, which I am not too cynical to say I believe to be an unqualified good thing. But it also leaves you with a trail of past lives. And… I guess I’m coming to terms with the fact that it has a downside.

Now, several of these “arcade games” lasted years. My time at Barbarian Group lasted a decade. It’s a fallacy to say that the arcade theory keeps you from learning how to handle obstacles or doesn’t build fortitude. I mean, we’ve all experienced the sensation of playing a new game and dying immediately, over and over. Then we look at the 12 year old kid playing it and kicking ass, and thinking “I HAVE to learn how to do this.” Then we play for hours, days, weeks until we’re pretty good at it. No, the arcade approach doesn’t mean giving up. It means developing a competency, even a mastery, no matter what it takes, but once you have it? Move on. Good or bad, I’m still not sure yet. Hell, I’m only now realizing there were other approaches to life. But at least I’ve come to terms with the fact that this is a part of me.

* Did you know that Asteroids earned $150 million in unit sales and $500 million in coin deposits? In 1980? That is $1.5 billion in today’s dollars.
† I have a job, btw. And I like it. He meant a full-time, operational thing at a product company. We both knew that.

Life as an Arcade was originally published in Rick Webb on Medium, where people are continuing the conversation by highlighting and responding to this story.

How I manage to read 60 books a year without being a speed reader.

Since posting my 2014 books read list, (along with 2013, & 2012, etc.), several people have asked “how I manage to read so many books in the year.” I don’t have handy advice at the ready when they ask, but it’s gotten me thinking a bit about it, along with my larger reading habits. Here are some tidbits of insight into my reading habits, both for books and other things.

So here you go. Eight minutes of reading about reading. These are the tricks that work for me. Thanks to my boss Pedro for reminding me to finally write this.

ABR. Always Be Reading. This is huge. People assume I’m some master speed reader (see below) — I’m not. The single biggest way to read a lot of books is to always be reading. On your commute. Before bed. At lunch (oh, the joys of a lunch alone with a book). I still do my civic duty watching the requisite TV shows (Mad Men, Game of Thrones, etc) and seeing the important movies to be seen. (Never mind, you know, having a job or a family). It’s not about reading at the cost of doing something else, it’s about reading when you aren’t doing anything. You’d be amazed at how often you can sneak in a few pages. Baby napping? Read a page. Also, drunk subway reading is the best.

Set a goal. If you were to go back and look at my 2009 reading list, it has almost nothing on it. Maybe 2, maybe 3 books. I had, previously, set myself a goal of reading the entire issue of The Economist every week. That literally took up all of my time. While it was wonderful to be the scintillating life of a party talking about the wacky antics of Alberto Fujimori (that guy gave me endless talking points), I found something was missing. So I set a new goal: to read, on average, a book a week, or 52 a year. It doesn’t work out to exactly a book a week, but the goal keeps me on track.

Don’t try and read what you, or others, think you should read. This one is huge. Reading is a curious pastime. If you think about it, the relationship between the consumption of various entertainment mediums and your friends is kind of interesting. I believe each medium lands in a different place along a personal-social scale. That is, some of types media consumption are profoundly personal, while other types are more social. With the socialization of the web, we don’t often think about this. There’s always been some effort at socializing reading (think book clubs), but the web, Twitter and, especially, Goodreads, have furthered this. Yet at the core, I believe reading is a more personal activity than, say, listening to music, watching TV or going to movies. If each of my friends put out a top ten list of their favorite movies or albums of the year, for example, I believe that with most friends I’d share several albums or movies. But when even very close friends post their year end reading lists, I find there’s often very little overlap. My good friend Rachel and I only share a couple books, while my friend Diana and I, for example, share only one, that she recommended to me. That’s okay. I still added several books from each of their lists to my reading list. My point is this: if I were to spend my time trying to read the books my friends, or the press, or the public, or Twitter wanted me to read, I’d not enjoy reading as much. Some types of books just don’t do it for me, no matter how much I should like them. If something is hugely important to me to read, I’ll slog through, but I’ll bookend it on either side with something I want to read.

It follows, then, that Guilty pleasures are totally okay. Fantasy, sci-fi, romance, whatever floats your boat, read away! Some of the works of great literature, today, were guilty pleasures in their day, and some of today’s guilty pleasures will become timeless classics. I believe, too, it’s better to be reading something rather than reading nothing.

However, Don’t be afraid to branch out. This is especially important if you’re still trying to get your reading habit going. It’s a lot like finding a career. We don’t always settle into what we think we should be, or wanted to be when we were young, because we have since been exposed to new experiences. Exposing yourself to new types of books increases the likelihood you’ll find something that captures your attention.

Don’t be afraid to quit a book, but do so sparingly. If some book isn’t doing it for you, it’s okay to quit reading it. But I’ve found that persevering often reaps rewards. A good rule of thumb is to only quit a book after you’ve gotten a third of the way, or even half of the way through. Also, I try to only quit 2–3 books a year, tops. More importantly, after I’ve finished a book, if I don’t think it was worth my time, I adjust my reading list and opinions to avoid reading books I think might be similarly displeasing in the future.

Different media for different environments. There are times it’s not practical to read a book. You might only have a few minutes. There are also times where a physical book is better to read on than your phone, or your kindle. Have media of all types at hand, if you can. I have a great Instapaper queue, and if I’m having a super fast lunch, or if my subway ride is only a minute or two, I’ll probably just read an Instapaper article.

Different material for different environments. The biggest problem in getting a good book reading habit going was, for me, was trying to figure out how to also accommodate long-reads from magazines that I felt like I had to read, for personal or professional reasons. It’s very, very difficult to keep up with the latest New Yorker profile on Samantha Power or Angela Merkel (both of which were excellent, by the way) and also manage to read books. Have different environments for both, and stick to the system. My solution? I only read magazines on the toilet. Books everywhere else. It works. Amazingly well. I’ve also been experimenting with only graphic novels before bed, but it’s not working out so well.

Embrace digital. The Kindle is amazing. Several years ago, at the dawn of the Kindle age (oh, that sounds so important), my friend Noah Brier told me he read way more ever since he got a Kindle. Since that was right around the time I had set myself a new goal of reading more books, that was all the encouragement I needed. It was a life changer. This is coming from a man that read Mason & Dixon, in hard cover, entirely on the Boston T. That hurt. Physically. The joy of hundreds of books in your pocket, virtually weightless. God, I must be old, but it still feels like magic. Recently, a good friend, my age, stunned me when he told me he read the first four volumes of A Song of Ice and Fire on his iPhone. That is amazing. But it works for him.

Reading speed doesn’t matter. I’m not some speed reader. I don’t read particularly quickly, and I don’t employ any skimming methods. I read every word, and I make sure I comprehend it. If anything, I’m too methodical, and there are times I think to myself “I could really skip this part, I get it already” — especially in non-fiction. But I don’t skip. I read it all. As an aside, I am obsessed with Spritz Inc’s Reimagined Reading app. With it, I can comfortably read over 500 words per minute. Alas, it’s not super widely implemented yet, but, god. The day it exists on the Kindle? I will be in heaven.

Avoid distractions. Turn off the wireless on your Kindle, or read paper. I keep my wireless off on the Kindle so I don’t click through too much to Wikipedia articles (the internal dictionary usually suffices). I’ll read background Wikipedia material later. I actually own a Kindle specifically so I don’t read on my phone or iPad, where I am too prone to distraction. This is, of course, a luxury, to have a separate, additional, reading device. If you’re using your phone or your tablet, turn off the wifi, and turn on the do not disturb functionality.

Give audio books a shot. They’re not my thing, but I can see the appeal. Listening to an audiobook counts as reading. Most of my exercise is walking on a treadmill, so I read my Kindle, but I’ve recently been experimenting with books on tape on my iPod while walking out in the world. It’s nice. I worry it’ll cut into my music-listening time (a whole other, not unrelated, time management issue), but I get the appeal. Whatever works.

Take notes or highlights. I’m not sure why, but once I started taking notes and highlights in my Kindle books, I started to read more. I believe it makes you more engaged. At first, my highlights were only profundities — little passages that seemed completely genius and shareable. Now, I highlight all sorts of things: funny quips, little two-word turns of phrase I’m impressed with. Things I want to remember — and, notably, references to other books. Recently, Amazon introduced a neat feature where if you highlight a single word and look it up, it will save all of those words into a list for you. This is a great vocabulary development tool.

Which leads us to the tenet build a reading list. Have a list. Always be re-sorting it. Keep it varied. Mix it up. If you’re reading a long, dense tome on economics, bang out a young adult novel afterward. Right now I have about 80 books in my queue, and I’m constantly rearranging them (most recently because of Rachel’s reading list and books on there I’ve been meaning to read for years). If you finish one book, pick up the next. I like to read a single page of a new book as soon as I finish the last book. This way, I’m committed to reading another book. Protip: There is an insane amount of $1 or less out-of-copyright books on Amazon. This year I read the complete works of Conan Doyle and Jane Austen on my Kindle. For a combined price of $1. Amazon also offers many books on a borrowing basis to Amazon prime members. I keep a dedicated Amazon wish list of these books.

One book at a time, or many books at once, either is okay. I used to obsess about this all the time. Now I just don’t worry about it. I have one book by my bedside (100, by Bill Drummond), that I’ve been working on for two years. So what. I’ll finish it some day. I’ve put down a book, read a whole second book, and picked up the first one again. Readers talk a lot about this, and what the best approach is, but I find that whatever works, works.

There you go. Let me know what works for you. Always looking to improve my approach. I hope this helps.

PS: If you enjoyed this, I’ve written a companion article, My Book Writing Habits.

My Reading Habits was originally published in Rick Webb on Medium, where people are continuing the conversation by highlighting and responding to this story.

I wrote this five years ago this week

(I wrote this originally for a now defunct ad magazine in 2009. We are *almost* out of this phase now. It seems that it only took 5 years.)

The year: 1923. The city, New York. The setting, a board room on Madison Avenue.

Over the past 20 years, a lot of shit has gone down. Seemingly from out of nowhere, this strange new device called the Telephone has burst into the American zeitgeist. Just ten years ago there were less than three million of the things in the United States, on something like 2,000 independent circuits. The circuits were unable to talk to each other, and the device’s utility was mainly confined to calls to the drug store and the neighbors. But the last decade wrought profound changes. In 1913 people cried monopoly and AT&T was made a government utility. In 1915 the technologies were invented to connect the independent circuits. These two events allowed this strange new technology called “long distance” to be invented, and over the past couple years it had become all the rage. Household penetration rates were pushing 40% and climbing fast.

And, in our board room on Madison Avenue, all hell is breaking loose.

“We can’t just answer this thing.”

“Dude.” (people did not say dude back then) the young turk planner (they did not planners back then) states his case: “These people are calling us whether we want them to or not. They have something to say. We need to listen. And preferably, we should say something back. There’s this whole new vibrant world of communications. And yeah, a bunch of it isn’t really about brands, but… Get this. People actually talk about our products on the thing as well. And sometimes… they just call us up to tell us something about our product. Something that before we’d have to pay hundreds of dollars to learn in one of those new-fangled focus groups.”

A well-coiffed, well-tailored Senior VP takes off his glasses in exasperation. “Yes, but think of the ramifications. We’d have to employ dozens — maybe eventually hundreds — of people, just to talk back. They’d all have to stay on message. They’d all have to be empowered to make offers and fix things. There’s just…” he starts to lose it at this point. “There’s just no way.”

“We’ve been yammering on to our clients about knowing our customers and the value of research for ages. This is what our clients pay us for. To know our customers. And here they are, just… just… telling us outright how they feel about our brand, and we’re not going to listen? We’re not going to talk back? We’re not going to ask them questions?”

“There’s just no way to control it. There’s no way. And have you even thought about the money? How are we going to make money off of this?”

“Our clients will save money on research by having this freely-available data at hand. They can take those freed up resources and spend them on other marketing services.” The young turk planner has found his groove again. They most definitely had groove in 1923. “And in any case, we could make money off of employing the people who answer these things. I should probably also point out that we’ll still need good quantitative research, this will never kill that off.”

The young turk planner goes in for the kill. “Look, I know it’s not pretty. It’s disruptive. It’s a pain. I know we’d probably rather keep making posters and ads in the papers — and don’t even get me started on that ridiculous radio thing. But we have to face it. Times are changing. Do we want to the kind of agency that keeps making newspaper ads forever —”

The Senior VP cuts him off. “And why not? What’s wrong with just making newspaper ads and posters? Business is great, we could keep doing this for a hundred years.”

“We could, we could,” the planner conceded. “But other agencies will move in and take this business. I heard those guys down the street at Ayer are starting a whole telephone department.

“Okay, okay, I might consider this. But I want a plan. I want a feasibility study. I want to know exactly how we’d integrate this… this… telephone into our marketing and our processes. How we could profit from it. Who’s gonna pick the damn thing up? How are we going to train that person? Whose budget is it going to come out of? How are we going to make any money off of this damn thing?”

“Well…” the young turk planner tentatively ventured… “I was thinking we’d start by picking it up when it rings and saying ‘hello.’”

From the Archives: Twitter v. 0.1 was originally published in Rick Webb on Medium, where people are continuing the conversation by highlighting and responding to this story.

The super rich should quit their jobs. 

There is a surplus of millionaires in the world. By 2020, there will be over 30 million millionaires on the planet, and nearly 20 million in the United States. The decline of the scarcity economy, combined with the increasing stratification of wealth distributions are contributing to the fact that, despite the fact that the rich are getting richer and the poor are getting poorer, there are more rich people than ever. Furthermore, planetary demographics, the onset of power shifting from the boomers to Gen X, and the tech boom insure that more and more of America’s millionaires are young. While the average age of a millionaire is 57, and only 10% of america’s millionaires are under 40, these stats still mean that by 2020 there will be over 2 million millionaires in the US under 40.

We should now insert the usual caveats that a millionaire is not rich enough to retire. Roughly the top 10% of the world’s millionaires have $5 million or more of assets. This is enough to never work again. This means, statistically, that there are some 200,000 people under 40, and around 2million people under retirement age in the United States who are rich enough to never work again.

The super rich should retire.

I believe these people should stop working. The super rich should retire. I believe this is almost (not quite, but almost) a moral imperative, contrary to conventional wisdom. There is nothing noble in the continued employment of these people. There is nothing good about their continued accumulation of assets through work. It’s impossible to not continue making money when you have money, through investments and management. But it is not impossible to stop taking jobs that other people could probably do better.

Were wealth a zero sum game, it would be flat out immoral, as the additional money from your unnecessary continued employment would be better used going to those in need, by employing them instead. The world economy is not a zero sum game, it must be admitted, but neither is it the exact opposite of a zero sum game. I believe It’s closer to a zero sum game than not, if you will. There is not infinite money for everyone. This is a personal belief, and difficult for economists to prove.

It is also, however, irrelevant. The math works without it.

Even without the zero sum game argument, it seems to me that there is still a clear moral imperative for these people to stop working. The work they do will be picked up by others. It is a popular American myth that these wealthy people are somehow more talented than those who would replace them, and thus their continued employment will contribute to the economy more than if other people held those same jobs. I do not believe this to be true, and see no empirical evidence to prove it in any economic statistics. Indeed it has been my experience that the opposite is true. The people I have hired have often been monstrously more talented than myself.

I’ve seen a few arguments around luck vs skill in success lately on the web (okay, on Secret). I find that for every person who claims we should credit luck more, many people come out and feel a spontaneous need to defend the skill quotient. I find this curious. It’s nearly impossible to find an example of someone who succeeded that we can conclusively prove that luck did not play a factor. Conversely, all around us we find evidence of idiots who have managed to be wealthy without any shred of skill. When we’re bitching about them, we spit out the word luck contemptuously, but are all too willing to acknowledge its existence. When it’s us, however, we are far more reluctant to do so. Nonetheless, it seems to me we have acknowledged the existence of luck conclusively in these dialogues.

In my view, based on past experience in hiring, the lack of economic data to the contrary, and the clear evidence that much of their previous success was luck, we can safely assume that there is a good chance that whomever replaces the wealthy in their former jobs may well do just as well, if not better.

If the ultra wealthy were to retire they would, I believe, shift from accumulating wealth to a) protecting it via investing and b) slowly spending it to live. This is a stimulus on the economy. Other people would take their jobs, which means 2 million new jobs as people replace those that move out of the workforce that do not need to be in it. By my rough calculations this, alone, would be accountable for a 1.2 point improvement in the unemployment rate of the United States.

This, alone, would be accountable for a 1.2 point improvement in the unemployment rate of the United States.

There is an argument to be made about whether, upon leaving full time employment that the wealthy would shift their fortune to safer investment opportunities, so as to not lose it. This has not been my experience, as the primary gating factor on undertaking risky investments among the wealthy, I find, is time. Once they’ve got the time to pay more attention to their investments, they tend to take a bit more of an active role and, therefore, undertake at least some more risky investments.

Then we have work stress related illness and the commensurate costs associated with it. Only 6% of workplace stress stems from job security. This, clearly, would not be relevant for the super rich. An additional 20% comes from difficulty judging personal and work lives. Though I’m sure the super rich feel this to some extent, let’s be charitable and say they do not. The balance of workplace stress comes from “workload” or “people issues,” that seems safe to say applies to any of the super rich working. Stress related health care costs the US $200 billion a year. Three quarters of all workers report experiencing stress in the workplace. Apply the math to all this pro rata and you have costs of around $1.7 billion of stress-related health care expenses for the super rich or their replacements. These costs, of course, can be borne by the super rich, and the stresses would most likely be felt just as acutely, if not more so, by their replacement workers.

Trickle-up economics > trickle-down economics.

But right now those replacement workers are one level down, already feeling the effects. They, in turn, would be replaced by people the next rung down, et cetera. Jobs would “trickle up” to replace the super rich. At the very bottom, the 1 million new entrants into the workforce are likely to be more expensive to provide health care, now, than they would be while covered by new, employer-provided health plans rather than the public sector.

Let’s call this trickle-up economics. People are promoted to replace a deluge of absences at the top.

This is not at odds with the nobility of work.

It seems to me the largest obstacle to this is the moral/social point of view. Simply put, Americans find working noble. Many of the super rich believe not only that they are providing social good by working (they are, let’s assume, but so would their replacements), but that it is ignoble to retire early. That work is inherently GOOD. I do believe there can be health benefits to staying busy. And, while I question the belief personally that work is inherently good, this theory does not require that. This theory is not incompatible with a belief of the nobility of work. But I question the assumption that this work needs to be done in pursuit of greater wealth. Bill Gates, of course, provides ample evidence to the contrary.

In many ways, this only makes sense. Why should a retirement age of 60 apply when you have already accumulated enough to be set for life? Why hasn’t society adjusted as more and more people achieve that level of wealth at an earlier age. And OF COURSE many more people are achieving that level of wealth at an earlier age, given economic trends that are very much in that direction.

I wrestle with this personally. I have achieved this level of wealth, on paper, and think there is something to be said for stopping. I believe there are other ways I can keep busy, from pursuing charity and philanthropy to the arts to spending more time with my family. That being said, my wealth has not been stabilized or manifested in a safe form. It is still very much paper wealth and liable to sudden disappearance. So, then, I must continue to work until it is truly safe. But I see no reason why I should be on a treadmill of more and more stress, working ever more challenging and difficult jobs just to enrich myself.

Many will argue that they continue working in order to continue striving to make the world a better place. Let’s look at that. Even if I WERE endowed with some genius insight or idea where I felt the world absolutely needed it and to not bring it to fruition would be somehow immoral, I believe the right and moral thing to do would be to work towards getting that to happen, and put younger, more in need, equally talented people in charge of it. Getting it off the ground, so to speak. I see no moral imperative that *I* need to be the one to do it, and important ideas suffer no difficulty attracting talented people to execute them. It’s hubris and ego to think that I, myself, would be vitally important after the idea came into existence (again, being generous to myself and assuming that somehow I was the only one to ever think of this idea — that does not happen).

I’ve written extensively about my belief that those who accumulate wealth have a moral imperative to re-invest the bulk of that money into job creation and things that help others (at the very least: charity, too, is an option). I now further believe that this should be taken a step further. Ask yourself why you continue to work. Ask yourself if someone else couldn’t be doing it. If nothing else, consider trying it for a year. See how you feel. On top of all of this, I believe there is a good chance you will be happier.

Edit: I forgot to mention this but it should go without saying, if you’re in the middle of the thing that made you rich, and you haven’t gotten it to a stable place yet, of course you shouldn’t quit and let it crumble. No one is suggesting that.

Trickle-Up Economics was originally published in Rick Webb on Medium, where people are continuing the conversation by highlighting and responding to this story.

Event listings online are still broken. And as ad dollars move to the web, local advertising has forgotten brand. 

This post is basically an ad. If an ad is a thing you write saying why you like something, when you didn’t get paid to write it. In fact, you paid them to be a part of it — as in you invested. So I guess, technically, it’s not an ad. Is it journalism? No. I am not a journalist. But it is honest, and true, and an expression of my feelings and why I love this company. Take this as a disclaimer that I am very, very biased towards DoStuff Media. This article aims to explain why.

You’ve probably not heard of DoStuff. If you live in Austin, you’ll know them as Do512. If you live in Chicago, you’ll know them as Do312. And now, if you live in New York, Los Angeles, San Francisco, Boston, Seattle, Nashville, Indianapolis, St. Louis, or Mexico City, they have arrived in your town, and you should check ‘em out. If you live in another city, look out for them. They are growing fast.

DoStuff exists in each city for one reason: to help those who want to go out and have a good time find the best things to do.

My love of DoStuff comes down to three things:

1. DoStuff is the easiest way to find out what’s going on in your town, and helps me find the rock.
2. DoStuff gives brands something new that they’ve been craving.
3. DoStuff is a great business in which I am psyched to invest.

I’m going delve into each of these reasons. And I’m not gonna lie. This is long. I suppose that’s partly because I’m so excited. But it’s also because I’ve been wanting to lay out everything I love about them for a while. Companies in quiet growth mode are always fun, but eventually I want to be able to tell people why I’m into an investment, and that time has come at last for DoStuff. Now I can just point people here!

Part 1: DoStuff helps me find the rock.

I love rock shows. I love going to rock shows. I haven’t seen 400 bands in a year since 2010 or so, but I still see a hundred or so every year.

I love the internet, too.

It’s always kind of confused me why the internet has not been more helpful to me in finding rock shows.

There is SonicLiving, SongKick (primarily in the UK) and BandsInTown, of course. But they always seem to be telling me David Bowie is playing at the local club down the street when it’s just a cover band. They also conveniently forget to tell me about half of the shows that really matter to me. The problem is clear with them — they are automated. They’re done by scraping, by algorithms, by machines. This, on paper, sounds great, but so far, I’ve found that in reality, they don’t quite work.

All of them have great social features — this is a must in any concert-going app, of course. But how good are those when the listings aren’t right? It’s the listings that matter first.

Now, there is an option to get accurate event listings on the web, but it’s a laborious one. You could go to every website of every night club, every couple weeks, and check and see if anyone good is playing. This is what I do now, but I miss things all the time — new venues spring up that I am not thinking of checking, and it seems kind of silly that in the year 2014 I can’t get some sort of alert from them when someone I like is playing.

The most upsetting thing about this whole thing is that this wasn’t a problem before the internet. I lived in Boston, so all I did was pick up a copy of the Boston Phoenix every week, flip to the back of the paper, and boom. There you go. All the listings for all the bands. God, I miss that.

The reason why DoStuff works for the user is because they faced head on the uncomfortable truth that other listings sites on the web want to ignore: you need feet on the ground.

The reason your local alt weekly was so much better than SongKick (and made tons of money for decades) was because they had a true local presence. They knew the community. And you need to be part of the community to make this work. You need to be there. You need real people telling other real people what is going on, what’s cool, and what they will like.

These real people are the only way you’re ever going to get that close-knit effect that allows you to do promotions and specials that matter: ticket giveaways and free shows (sponsored by brands!)

The reason this works for the user — and for DoStuff — is because DoStuff’s local properties in each city are a partnership with one of the city’s most important and active folks in that live music scene.

And what a list of participants it is: the owners of The Bowery Presents and Brooklyn Bowl in New York, The Echo in LA, Lollapalooza in Chicago, and the famed Noise Pop fest in San Francisco, to name a few. Plus the legendary Don Law in my beloved Boston, festivals like Bonnaroo, Governor’s Ball, and New Orleans Jazz Fest, and seminal music sites like KCRW, Brooklyn Vegan, and Okay Player. Damn.

Part 2: DoStuff gives Brands something new that they’ve been craving.

Let’s face it: Local activation at scale is hard. Walking around SXSW the other week, I had a ball looking at the “brand activations.” They really are pretty funny, aren’t they? What is it about them? I used to do a fair amount of marketing at SXSW for my old agency, The Barbarian Group (I’m particularly proud of the GE Carousolar we did a couple years back). These days, we don’t just see internet agencies and tech companies marketing to other nerds at SXSW: we see brands.

Most of these, of course, fall short. But some of them work, I suppose, are pretty good. But the whole strategy is kind of odd. A brand shows up at SXSW, because we’re supposed to be influencers. And we, the SXSW attendees, have lots of Twitter and Instagram followers, and we’ll talk about what cool thing that brand is doing, hopefully. And then other people, who follow us, will see it, too. Earned media! Brand activation!

This, in the past few years, made a lot of sense. These days, I’m kind of wondering one thing: is it really a logical proposition that all the influencers in social media are at SXSW? It used to be the people with the most followers on Twitter were a bunch of nerds. Now? Not so much.

Aren’t there influencers in every city?

Of course there are. Brands know this. But they come to SXSW for two reasons: on-the-ground, experiential marketing is expensive. And budgets are limited. SXSW is an easy place to hit a lot of “influencers.” There are other events, of course: rock festivals and sporting events and other trade shows. But boy, it gets expensive. Everything is custom. Everything is a one-off deal. Even if I take the thing on the road, it’s a massively complex, time-consuming, hella expensive endeavor.

Doing local requires genuine human connections. You can’t scale it using technology alone. You can spend immense amounts of money trying to replicate these human connections on the ground. And even then, that lack of a local spark — as we see with so many of these flat SXSW activations — will be a major obstacle for you.

Or, you can make it work with a partner like DoStuff. In the past, such an organization didn’t exist across multiple cities, so marketers were left with two bad options: work with a “product” company with no on-the-ground presence, or work with an array of local media properties across the country — a labor-intensive proposition, and one which loses any potential for any national economies of scale.

I first met the DoStuff guys in my Barbarian days. I was doing work for a client who needed a digital, social and local campaign. I partnered up with Lollapalooza to deliver, and I met a gentleman named Michael Feferman (aka “Fef”), who as Digital Director was my point man at Lolla. The campaign I bought from Lollapalooza was a giant success.

This is all well and good, but I wanted more. There was one problem: Lollapalooza was only in one city.

DoStuff grew out of Fef’s festival collaborations with Scott Owens, who had already co-founded Do512, now Austin’s most popular listings site. While working together on software for Lollapalooza and the Austin City Limits Music Festival, they saw an opportunity to take the Do512 concept national and provide something that brands have been looking for without success: combined local + national brand advertising in the digital age.

This is experiential, local engagement for brands at scale — a massive, untapped market.

Brands, naturally, love this. Especially brands that want to be on the ground around the country. Brands that want to connect locally and nationally. Brands that sell a brand, not a discount.

By having these partners on the ground, DoStuff is able to do three important things:

1. By giving their audience the best, up-to-date and accurate listings, they can get people to come out to a show or event.
2. They can offer discounts, specials, and free tickets, just like your old beloved college radio station.
3. They can offer local advertising in-market and build a national ad network, allowing to achieve real local engagement at scale, both online and off.

The third reason above is why I am not just a fan and user of the service but also an investor. For me, they hit all the sweet spots: they have deep, on-the-ground access to offer great digital local advertising in major markets. They can combine this with unique, special events on the ground — they are not just delivering local from afar.

And remember: this isn’t just on-the-ground. It’s digital and physical. They can support local activations in multiple markets with digital local and national ad support. They can also provide localized content creation and influencer marketing in those multiple markets, and they can tie it all together for a brand into a single integrated campaign that gets executed in each market by people on the ground with long-term local relationships, knowledge, and audience — so that it actually works.

No one else can offer this. Not even close.

DoStuff solves two problems in my life: one as a user and one as a marketer. Turns out they are related.

Part 3: Why I’m psyched to invest in DoStuff

And what they offer in the local market is unique: it is brand advertising. It’s emotional, it’s about brand association and lifestyle, not just “buy now” or “20% off” or “try the fish.”

This is worth talking about. There is a difference between brand advertising and direct advertising.

If you know me at all, you’ll know that my career, both in advertising and in technology, has been spent looking at how advertising dollars are spent in America and trying to find opportunities that help advertisers more effectively move their advertising online. I’ve been particularly interested in “brand” advertising vs. “direct” advertising. Think “Just do it” vs. “buy now.”

I’ve extensively written about how even if we brought every last advertising dollar to the web, there will only be, at most, nine more Googles. And it’s my belief that until we offer better options for brand advertising — “Just do it” — there are giant pots of money that won’t come over to the web. This is what we tried to do at Barbarian Group: create compelling brand advertising on the web. And it’s what we were trying to do at Tumblr: offer brands a platform where they can communicate emotionally with their customers.

Google, of course, was an early tech darling not because it was the first company to bring over significant advertising dollars at scale — Yahoo! did this first with display advertising. But display advertising, despite claiming improved metrics over broadcast and print, primarily only worked as brand advertising. It acted more as a billboard (inspirational, emotional) rather than a coupon. Google upended this, allowed for perfect trackability and accountability, and in the process brought billions of dollars to web advertising.

The evidence, to me, that brand advertising is a giant opportunity on the web is in spending on television ads.

You’ll see that not only is television advertising not shrinking, but in fact it’s growing at quite a nice rate, and projected to continue to do so.

And brand advertising is not a small market. eMarketer estimates that brand advertising comprises a minimum of 27% of the ad budgets in the travel industry, and up to 63% in sectors such as CPG and Entertainment.

Ad money has been coming to the web, and is still coming to the web, but direct and brand dollars have been coming over at different rates, and there is much more brand money still in traditional media than on the web. Most brand money has still not moved over yet.

This is one factor that I look at when searching for compelling investments in the ad space, both as an angel investor and at Quotidian Ventures: opportunities for great brand advertising on the web.

The mythical “internet dollars” slide

Many of you, in your travels in the digital advertising world, will see this slide at one point or another. This version comes from Mary Meeker’s last internet trends deck:

The accompanying narrative to this deck usually implies that there is a great discrepancy in ad spending and media levels, and all money is coming to the web eventually. And yet, and yet, you’ll notice that most of this money is coming from print and radio and not television.

You see what I’m getting at? The reason money isn’t moving out of TV budgets is that marketers know how important brand advertising is. And yet somehow the same marketers keep looking at the web as merely a direct advertising platform.

Now, this isn’t entirely irrational. It’s because digital hasn’t provided great brand advertising opportunities yet. Direct? Sure. Google killed it. Brand? Um, well, we have display? Native advertising is attempting to provide some opportunities here, and there is much potential there.

But. Native can only work in certain situations.

Which brings us to local.

One hundred and thirty two billion dollars. That’s how much money is spent on local advertising in the US these days. $132 billion. Of that, so far, $25.7 billion, or just under twenty percent, is spent online.

To give you a sense of proportion, total spending on advertising in the United States in 2013 was $171 billion.

In short, local advertising comprises 77% of all ad dollars spent in the US.

Now, where is that money being spent in local? As we can see, 20% of all local ad money is being spent on the internet, but let’s look at the details:

The internet has, thus far, really only made a dent in newspapers. We all know this. Local advertising on the web — especially Google, & Craigslist — has hollowed out newspaper classifieds. Yelp! has done a great job bringing some of that money over to the web, and Foursquare (who I am invested in and love) is starting to make inroads as well. This is primarily coming from local newspaper and yellow pages.

But what I find interesting here is that we’ve made nary a dent in direct mail, cable, magazines, and out of home. This makes sense. It’s the bread and butter of local advertising.

So, then, where is the local brand advertising on the web?

Foursquare is making some progress at grabbing local brand dollars with some of the ads you receive at checkin, and it’s one of the reasons I love them. But that’s it.

To help think about this, I think it’s helpful to think about three things: local billboards, local television spots, and local non-classified, non-circular ads. Think of your college weekly paper. Think of all the ads in there for rock shows, local banks, cell phone companies (and, I suppose, escort services, but we’re not going for that here). Where has that gone?

Nowhere.

This is the real investment value in DoStuff. Massive local brand dollars are waiting to be moved to the web at scale. They’ve just had nowhere to go. Until now.

On top of all that, they’re everything you want in a tech investment: they have users (they’re just getting started but their registered users are already in the seven figures), they make real money (7 figures and two years of solid growth pre Series A!). From a financial perspective, they avoid the GroupOn hellhole that is thousands of local sellers. By partnering in joint ventures in each market with an established local presence, they have instant, deep access to the local market without trying to break in from outside, thousands of miles away.

In my travels in tech, I’ve found that few tech investors — even the great ones — have a firm handle on the holistic economics of the ad industry, local and national, online and off (my next book is about exactly this topic.) But I think this has been part of the reason that many of the investors in DoStuff thus far have come from the world of live rock promotion. They immediately grasp what’s been wrong with the previous offerings in event listings, and intuitively understand the local ad markets in which they operate, and what we’ve lost as we’ve lost print. What digital hasn’t replaced yet.

But the tech investors that have invested are exactly the ones that understand this space: Owen Van Natta’s Luminor Group, John Battelle, and Andrew Razeghi, along with the elite of their Austin hometown tech who know a great company when they see one: Bill Boebel (Quotidian’s co-investor in Moveline), Pat Matthews, Jim Eustace and Rony Kahan.

They do something useful for users and clients, they’re a great investment, but — best of all — they are really, really nice. Also, they live in Austin. Who doesn’t love that laid back Austin lifestyle?

Scott and Fef are two of my favorite people. I’ve been working with them for years now, both at C3 and at DoStuff. I’m proud to finally be telling the world about what they’re doing, and why I believe that DoStuff isn’t just another listings company. They still have a way to go, of course. They are constantly working to improve their product, and while their mobile web experience is great, they will serve their audience better once they’ve got a native app. And DoStuff is in 13 cities now but the network effects only grow stronger as each of those properties matures and as they add new cities to the mix.

But — all those are details. Right now, DoStuff has a product that its audience loves, uniquely valuable offerings for brands, and a business model that is to die for.

And they’re just getting started.

Why I love DoStuff Media was originally published in Rick Webb on Medium, where people are continuing the conversation by highlighting and responding to this story.

Note: I am gathering some of my better essays from the past and collecting them on Medium, as they are easier to store here than my Tumblr. Original here.

This one was written September 11, 2013.

It’s okay. We all want to do it. The show is amazing. The mood is wonderful. You want to remember it. And hey — it’s the 21st century. You CAN remember it. You can take a picture. Ten years ago, this may have been considered the height of rudeness, but there’s no getting around it now. It’s too much to expect the general public to refrain. The thing is, however, that you are most likely still completely annoying to others while taking this photo. But with a few simple tricks, you can get a decent photo without seeming like (too much) of an asshole to those around you.

Follow these simple rules!

1. Be aware of your surroundings. Not all rock shows are the same. Seated theater shows, especially, require additional consideration. It’s one thing to stick your camera phone in the air when everyone is standing and screaming and waving their hands in the air like they just don’t care. It’s another to do it in a dark theater, at a show where everyone is having an emotional moment with a sensitive artist.
2. Turn off your fucking flash. Seriously. It doesn’t work. it makes your photos worse. And it’s annoying as shit to everyone around you. And the artist you supposedly love. Every time someone takes a photo of a rock show with a flash, a kindly grandmother gets punched in the face.
3. Turn off the sound on your phone. No one wants to hear your stupid shutter click sound, and YES, they can hear it.
4. Turn the brightness down all the way on your screen. The most annoying thing about others taking photos is how ridiculously the light it creates in the darkness (see rule 1) drawing EVERYONE’S attention away from the stage and pulling people out of the moment. You don’t need to do this to anyone. There are people behind you. There are people RIGHT behind you. You are in a dark room. The bright screen does not make your photos better. Bonus: Longer battery life.
5. DO NOT USE A FUCKING iPAD TO TAKE A PHOTO. Seriously. This is not allowed. A camera and an iPad are not interchangeable.
6. At a seated show, there is no real reason to hold your camera way up in the air. Try and block the screen with your head for the people behind you. If you must raise the camera to get a photo, follow rule 7.
7. Now. here’s the tricky part. Put your finger on the shutter button. Raise the camera, and align everything. Then rapidly take 3-5 pictures in a second or two. Then bring the camera down. This is the most important thing. You do not need to hold the camera up the whole show. You will not get a perfect shot by waiting with the camera in the air. If it makes you feel better, it’s not you. The shutter button has a tiny delay that basically makes this impossible.
8. Lay off the video. It’s gonna look like shit, it’s going to sound like shit. You’re never going to watch it again. Someone else there is doing it better. This is really just for the pros. I have, once or twice, shot a live rock video on my phone, posted it to YouTube and gotten a couple thousand views. But you’ll notice that a) they still look and sound like shit, b) these were at outdoor festivals where I wasn’t annoying anyone and c) there are still better versions on the web. Plus, you are being totally annoying to everyone around you.
9. Don’t bother putting the photo on the web until after the show. Seriously. First, you’re totally missing out on a band you paid a bunch of money to see. Second, you are being totally annoying to everyone around you, and finally, really, any bragging rights you’re getting from the photo you can get just as easily if you put it up after the show. If this is something that you vitally, absolutely, need everyone to know you’re at RIGHT NOW, you have two options: either post the obligatory blank stage photo before they band has started, saying how excited you are, or go out into the lobby and post it from there.

BONUS TIPS FOR THE PHOTO ACTUALLY COMING OUT SORT OF OKAY.

1. Often, much of the stage is dark. Dramatic lighting looks cool in real life, and experts can capture it with good cameras, but your camera phone isn’t going to do it justice. The only time it’s worth trying to take a photo is when the whole stage is brightly lit. Wait for these moments. Take your burst of photos then. Quickly. Put your camera phone down the rest of the time.
2. Don’t bother trying to zoom. Take the whole stage. You are not going to get the beautiful close up shot of just the singer that seems to be in so much vogue with Brooklyn Vegan and Pitchfork.* If you must zoom, you can zoom when you are putting the photo into Instagram, as Instagram generally has a lower resolution than your camera’s phone, and you can do so then without loss of pixels. Consider artistic compositions with the stage, lights and crowds. If you’re REALLY far back, a slight zoom of maybe 10% is acceptable, but it’s still gonna probably look worse.
3. If you have an iPhone or any other phone that allows for touch exposure control, touch the darkest place on your screen before you shoot one burst, and on a second burst touch the brightest place on the screen (assuming you have followed bonus rule 1).

Thank you! Follow these simple rules and not only will your photos come out much better, you will be far, far less annoying to the people around you.

* I’m not sure what’s going on with this. It’s like the music pubs own little version of the loudness war. If the trend continues, eventually music pubs will be publishing photos of the nose hairs of our favorite singers. I suspect it’s the one way the pros have a way to highlight just how great their access and equipment are. Personally, even when shooting pro I like a 50 mm F 1.2 lens, from further back, catching the atmosphere and, you know, the rest of the band, who actually do matter.

From the Archives: How to Take a Photo at a Seated Rock Show Without Being (Too Much) of an Asshole was originally published in Rick Webb on Medium, where people are continuing the conversation by highlighting and responding to this story.