Just over a year ago, you might not have had the slightest idea what “I just unlocked the ‘Superstar’ badge on @foursquare!” meant. But since its launch in 2009, social media startup Foursquare has grown to nearly 1.8 million users, rolling out new products and accumulating serious cash (the company secured an additional $20 million in funding in June) along the way.

Dennis Crowley, along with Naveen Selvadurai, started the company around his kitchen table after shuttering a similar service called Dodgeball. “One of the reasons I think that Dodgeball suffered is because it wasn’t really a fun one-player experience. If you didn’t have 10 friends on it, you really weren’t getting much value out of it,” said Crowley. “So a lot of stuff we tried to build into Foursquare from the very beginning was about [exploring] the city by yourself. There’s a reason to check in beyond just sharing it with your friends.” Eventually the pair got out of the kitchen and made their first hire, and today they have a team of 27 that barely fits into the office. “We’ve been waiting for years and years to be able to do interesting things with mobile phones in the location space, and it feels like all the pieces are finally lined up to make those things happen.”

WebNewser editor Alex Weprin caught up with Crowley to talk about how he’s grown Foursquare and what’s next for the company.

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Name: Dennis Crowley
Position: Co-founder and CEO of Foursquare
Resume: Started out as a researcher for Jupiter Communications before joining mobile app provider Vindigo as a product developer in 2000. In 2003, worked on MTV’s wireless product development side, and held stints at PacManhattan and ConQwest 2004. In 2004, he founded Dodgeball.com, one of the first mobile location-based services. It was acquired by Google in May 2005; Crowley left in 2007 and Google shuttered Dodgeball in 2009. Crowley founded Foursquare in January of that year.
Birthdate: June 19
Hometown: Medway, Massachusetts
Education: Bachelor’s degree, Newhouse School at Syracuse University; master’s degree, New York University’s Interactive Telecommunications Program
Marital status: Single
First section of the Sunday Times: Sunday Styles
Favorite TV show: The Neistat Brothers
Guilty pleasure: Peanut M&Ms, Adidas ZX sneakers
Last book(s) read: The Facebook Effect, by David Kirkpatrick, and Boo Hoo: A Dot.com Story from Concept to Catastrophe, by Ernst Malmsten, Erik Portanger, and Charles Drazin.
Twitter handle: @dens

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[Foursquare] struck a couple of deals with television networks, Bravo and C-SPAN — is that a mutually promotional partnership that benefits each of you, or do you think it can actually drive revenue at some point?
We don’t disclose the terms of the deal. Some of them are generating revenue, and some of them are just interesting and exploratory. A lot of it is an experimentation to see if we get media properties and different media brands on Foursquare, are they seeing some benefit in terms of leaving different pieces of content around [the] real world for other users to discover? So every deal that we do is a little bit different. We’re inching towards a strategy that works for everyone.

How do you handle suggestions from users, like if someone has an idea for a badge?
We built a forum a while ago, almost like a year ago. We still go through it pretty regularly, maybe once or twice a month. And now we’re structured to the point that we have these badge meetings that go on twice every week, and occasionally we’ll go through the queue and pull out four or five good ideas and try to push those out.

“We’re doing a lot of things to explore and experiment in [the location-based] space to try to tease out the things that are going to be most interesting to venues, but a lot of value to users, too.”

Do you think Silicon Valley has more people willing to fund ventures compared to New York?
Yeah, I think that might have been the case before. I know when Alex [Rainert] and I were trying to raise financing for Dodgeball back in 2004, we had a really tough time because there really wasn’t a strong angel network here in New York, especially for tech startups. And even when Naveen and I were trying to raise financing really just last year, it was a little bit more difficult. But I think even since that process, a lot of other firms have opened up shops in New York. There’s definitely a resurgence of the New York tech scene, and I think you’re seeing that and also in the presence of other investors here, too.

What’s the best business advice that you’ve ever received?
Well I think it goes back to what my mom used to say, way back in the day, because I never believed it. She was like, “If you keep working on the stuff that you really love and you’re really passionate about, then everything else will just kind of work out.” When I was like 20 and 22, it didn’t really make much sense, but with these projects, even Foursquare — I’ve been hammering on some of these issues or some of these questions for about 10 years, and it seems like her advice is generally pretty good now.

What advice would you give to an entrepreneur?
I think it’s being persistent with what you’re trying to do. I always encourage people to try and go out and team up with folks who can help them build a prototype. It’s funny, I go to these parties or conferences, and people will pitch me these ideas that they have: “What do you think? Isn’t this great? Can I raise financing on this?” And you know, I think all those are good and interesting ideas and stories, but it’s really difficult to take an idea and execute on top of it. So I really encourage people to team up with different groups of people or different groups of skill sets and really try to get something off the ground.

Where do you think the biggest revenue opportunities are in the location-based social space?
Location’s pretty broad, so I guess it depends on what you’re tackling. For the stuff we’re looking at ,I think there’s really good opportunities in connecting users with local businesses. We’re doing a lot of things to explore and experiment in that space to try to tease out the things that are going to be most interesting to venues, but a lot of value to users, too.

Is there any concern at Foursquare about Facebook launching its own location-based service?
We’ve spawned a lot of different competitors, and we definitely look at what Twitter and Facebook are doing. We’re really interested in the way that they’re approaching location, too. I don’t really have a lot of insight into what those guys are launching, but we look forward to seeing what it looks like when it does come out, and if there’s ways that we can work together with them.

“We’ve been waiting for years and years to be able to do interesting things with mobile phones in the location space, and it feels like all the pieces are finally lined up to make those things happen.”

What do you think Foursquare will look like in, say, five years?
I don’t know. It’s funny because we have a road map that could take us a couple of years. But again, you look at even four years ago the iPhone wasn’t out, and look at how much things are even going to change just with iPhone 4 coming out and all these background location tasks suddenly being available. It’s hard to really gauge, but we’ve been waiting for years and years to be able to interesting things with mobile phones in the location space, and it feels like all the pieces are finally lined up to make those things happen.

What’s a typical day at Foursquare like?
We’ve got this one floor in the Village Voice building, and there’s three different companies there, and there’s just no more room. Like, you walk in and there’s absolutely no more room. That’s after we moved about 10 people downstairs. There’s a lot of shuffling back and forth, people moving around trying to find a conference room, trying to find a place to sit, trying to find a place to work. It’s pretty hustling and bustling. A lot of people come in for their first time and take a look, and they’re like, “Oh my gosh, I can’t believe you guys actually work here.”

I probably get in around 9:00 or 9:30, and it’s really running from meeting to meeting and trying to catch up with as many people in our office as possible so I have a general idea of what’s going on. And then usually speaking to some brands and speaking to some potential partners that we’re doing, either media companies or mobile companies. It’s not a lot of coding these days. It’s a lot of coordinating and just communicating with people.

How do you and Naveen [Selvadurai, co-founder] work together?
We sit next to each other. He’s managing the client team, and I’m running around to get a bird’s eye view of everything that’s going on. A lot of what I’m doing is helping Alex [Rainert, chief product officer] out on trying to organize and get a lot of the product stuff up and running. And a lot of that touches what Naveen is doing on the client team. So we work pretty closely but not every single day together.

What mobile devices do you use?
I have an iPhone — not the new one, the old one.

There’s a bunch of them laying about in the office. We occasionally do this thing where someone will trade in their preferred phone and take out a Blackberry for a couple of days or take out the Android for a couple of days just so we can get a feel what it’s like to exist in one of these other apps.

What places are you mayor of?
I think I’m only mayor of one. It’s Scratcher, which is the bar across the street from our office. I’m pretty proud of that one because there’s a lot of people checking in there all of the time, and I’m still holding down the fort. I used to have a ton of them, including the Chinese food restaurant in my suburban Boston town, and someone took that away from me a couple of months ago. I don’t know who it was, but that’s a sign that the service is growing.

Tune in to our Media Beat video interview with Dennis Crowley airing next week on WebNewser to hear his take on Silicon Valley startup culture vs. New York’s, how Foursquare handles celebrity users, and his tips for media entrepreneurs.

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Blake Gernstetter is mediabistro.com’s associate editor.

When Seth Godin talks, millions listen. With one of the most successful blogs on the Internet, the New York Times bestselling author and marketing guru has guided his readers on topics such as leadership, viral marketing and new media. Corporations like Aol, Microsoft, Procter & Gamble, Sony Music, and Sprint have hung on his every word, hiring him as a speaker for their private functions.

And as a testament to his influence over the media, after Godin broke the news in an excerpt from this interview posted on mediabistro.com’s blog GalleyCat that he will no longer publish his bestselling books with a traditional publisher, news outlets went berserk. The Los Angeles Times, New York Observer, Fast Company and even The Wall Street Journal took our lead in covering what some say could be a defining moment in the already shaken book publishing industry.

But this is just the beginning for Godin. He has plans to roll out his teachings via eBooks, print-on-demand, audiobooks, podcasts and apps on his terms, no doubt bringing his millions of followers along for the ride.

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Name: Seth Godin
Position: Author, entrepreneur and marketing consultant
Resume: Began as a brand manager for Spinnaker Software while pursuing his MBA from Stanford. Created Seth Godin Productions, a book packaging company, selling more than 120 books. He then formed one of the very first online marketing companies, Yoyodyne, and introduced the world to the concept of “permission marketing” — the basis of his book of the same name. Unleashing the Ideavirus, Purple Cow, All Marketers are Liars, and others followed while he spent a stint as the VP of direct marketing for Yahoo!. Wrote 12 bestsellers on marketing, formed mega-successful online portal Squidoo, and become a vocal advocate of change for media and the book publishing industry.
Birthday: July 10, 1960
Hometown: Buffalo, NY
Education: Tufts University with a degree in computer science and philosophy. MBA in marketing from Stanford Business School.
Marital status: Married
Favorite TV show: Does not watch TV.
Guilty pleasure: “80 percent or higher dark chocolate, the more handcrafted the better.”
Last book read: Nothing Sacred, by Douglas Rushkoff
Twitter handle: @thisissethsblog

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Starting with ground zero, how did you build your audience?

When I launched Permission Marketing, I had an email newsletter. This was before blogs, and it grew to more than 20,000 people. I would write once or twice a week; anything I felt was relevant to my readers. It wasn’t about me selling anything or me pushing things at people. It was about delivering a message I thought people wanted to get. The side effect was that every time I would send out an email, approximately one percent of the people would hit reply and argue with what I said. That meant I was getting 200 or so annoyed or angry emails every time I hit send. I got conditioned into believing that I shouldn’t send an email because I knew I would be hit with a torrent of “nasty-grams” in return. So, I just stopped ’cause it wasn’t making me happy.

“I’ve decided not to publish any more books in the traditional way. 12 for 12 and I’m done.”

A couple years later I was at a conference which Fortune magazine sponsored. I met the founders of Google and was introduced to TypePad. I started blogging for real and again, only 30 or 40 people were reading it. The secret is 3,700 blog posts later, if you add 10 or 20 or 50 or a 100 people every day, it’s going to get to be a big number. That’s, I guess, the short version of how the core of the audience came to happen. It’s drip, drip, drip every day — asking people for permission, not violating their trust, giving them what you promised and nothing else. I never try to make a profit from the interactions I have with people in that format. I think I owe them something, not the other way around, and so as long as I can write for them, I figure then they will keep reading.

You made headlines by giving away your book, Unleashing the Ideavirus, for free. Is the free model still effective today with so many choices now for free product?
Permission Marketing had already been a New York Times bestseller when I wrote Unleashing the Ideavirus, and as I was writing it, I was thinking,’Am I going be a hypocrite, or am I going to take my own advice?’ The book is about the fact that the ideas that spread win and the best way to get your ideas to spread is to make it easy to spread, and hardcover books are really hard to spread.

So, I decided to take my own advice and publish it for free. It’s worth noting that I made more money on that book than the book I sold a year before because after the book spread, we self-published it in hardcover for 40 bucks, which Amazon sold at a discount, and it went on the bestseller list. There is a lot of free stuff out there, but either it’s junk or it comes with so many strings attached that people don’t wanna touch it. Then, the amount of stuff that is out there that is free and juicy and worth sharing is actually pretty small, and so there is an opportunity. I’m not saying that everyone needs to be in the free content charity business. I think that there are ways that you can leverage the attention that you get for free into a permission asset, build the tribe, and actually make money doing so.

You could be described as a modern day philosopher on marketing with your parables and illustrations. But what specific advice do you have for those who want to create and build their brand?
You can’t be a wandering generality. You have to be a meaningful specific. You have to “stand for something,” as my friend Zig would say. And that is not so easy because a lot of people I know who write are just plain smart, and they are smart about a lot of things. They don’t necessarily want to be disciplined enough to be smart about just one thing. It’s also boring to be smart about just one thing, until you break through and your brand gives you the leverage to go really deep.

“There are ways that you can leverage the attention that you get for free into a permission asset, build the tribe, and actually make money doing so.”

I have a blog post called “First 10,” and what I’m arguing is that everyone has 10 friends or family members or colleagues or people in the street who will read something that they write, who will look at video that they made. Those 10 people, when they are exposed to what you do, if they have no interest whatsoever in spreading the word, then why do you think the next 10 people will? At some point, the work you do has to be magical enough that it spreads without you harassing people, ’cause otherwise it just doesn’t go anywhere. There is a number of critical masses, probably more than 10, but it’s less than a thousand. If it’s not, then you need to work on the work so that once your work is exposed to those kinds of people — 20 or 30 or 40 or 50 of the right people — they’ll spread it. Then, you’re on your way and if not, you have to think hard about who you’re exposing it to and what the work is like.

You blog every single day. How do you keep your ideas fresh for your readers?
l don’t buy that the people don’t have enough ideas. It is hard for me to imagine how someone can go through the whole day and have talker’s block, I have never met anyone who woke up in the morning and had so little to say they were mute until they went to bed that night. People don’t get talker’s block, so why do we get writer’s block? We get writer’s block ’cause we are afraid, it’s easy to talk because you can deny it later and it disappears, but once you write it down, that’s when the fear comes from. That’s where you say I don’t have any good ideas and all I do is write like I talk. If I have something interesting to say, I say it and then I write it down, it’s not that hard. I think that the art here is in chopping down the wall, the barrier between what you want to say and what you are afraid of, and letting people hear your best stuff.

“I’m at a loss to think of one thing the book industry does well in 2010 that it wasn’t already doing in 1990.”

You have been very vocal about what the book publishing industry could do better. What are a few things you see them doing right?
The book industry does a great, fabulous, miraculous job of doing what they needed to do in 1965. Great jobs for good people. Ethics that matter. Good taste. Products to be proud of. In terms of responding to changes in the world, I’m at a loss to think of one thing the book industry does well in 2010 that it wasn’t already doing in 1990. Not one new thing done well.

Authors have so many opportunities now to self-publish or publish their own eBooks. Is this something you as a multiple New York Times bestselling author would consider?
I’ve decided not to publish any more books in the traditional way. 12 for 12 and I’m done. I like the people, but I can’t abide the long wait, the filters, the big push at launch, the nudging to get people to go to a store they don’t usually visit to buy something they don’t usually buy, to get them to pay for an idea in a form that’s hard to spread… I really don’t think the process is worth the effort that it now takes to make it work. I can reach 10 or 50 times as many people electronically. No, it’s not ‘better,’ but it’s different. So, while I’m not sure what format my writing will take, I’m not planning on it being the 1907 version of hardcover publishing any longer.

What are three of the biggest mistakes people make when trying to build their brand?
Impatience. Selfishness. Spending money instead of conquering fear.

NEXT >> Making an eBook: Getting Started

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Jeff Rivera is the author of Forever My Lady (Grand Central) and the founder of GumboWriters.com.

In late 2008, Jeff Bercovici at Portfolio observed that, because The Atlantic was known for its “commitment to long-form narratives and quasi-academic takes on culture and politics,” it was a “somewhat unlikely” candidate for success on the Web. And yet, succeeding it seems to be. In June, when most people’s thoughts turn to beaches and bikinis rather than bills and bluster, TheAtlantic.com attracted 4.2 million unique visitors—numbers it had previously not seen since the frenetic lead-up to the 2008 presidential election. Also that month, The Atlantic Wire, the new standalone opinion-curation site the magazine launched last year, had almost one million unique visitors. The industry is also taking notice. The site won the 2009 Webby Award for best online magazine and was nominated for best magazine website at this year’s National Magazine Awards.

Leading the magazine’s charge into the digital future is Bob Cohn, Wired‘s former executive editor and a 10-year veteran of Newsweek‘s Washington bureau. He spoke to mediabistro.com about the future of the 10,000-word article and the necessity of, ultimately, surrendering to the chaos of the wild, wild Web.

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Name: Bob Cohn
Position: Editorial director, Atlantic Digital
Resume: Started in Newsweek‘s Washington bureau as an intern before eventually rising to legal affairs correspondent where he spent 10 years covering Capitol Hill, the Supreme Court, the Justice Department, and the Clinton White House. Became editor and publisher of Stanford magazine and executive editor of The Industry Standard. Served as executive editor of Wired from 2001 to 2008 before joining The Atlantic in January 2009.
Birthdate: April 18, 1963
Hometown: Chicago
Education: BA in American Studies from Stanford; master’s in the Study of Law from Yale Law School
Marital status: Married, two daughters
First section of the Sunday Times: “I triage by scanning the front page, looking at ‘Book Review’ table of contents, studying the magazine cover. I’m mostly in note-for-later-reading mode. The first section I actually read is typically ‘Week in Review.'”
Last book read: The Good Earth, by Pearl Buck
Favorite TV show: Friday Night Lights, Mad Men, Weeds
Guilty pleasure: Red wine and dark chocolate, late at night while working or watching TV
Twitter handle: @1bobcohn

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The Atlantic magazine, in print, is quite successful as a long-form, lean-back experience. Why bother investing in a Web presence?
Because there’s a clear sense that people want to consume news, analysis, and information on the Web. We want to be in that game. The Atlantic was actually on the Web very early. We were one of three magazines that America Online came to in 1994 and said, “Can we put your magazine content into our new online community?” The Atlantic‘s commitment to the Web has ebbed and flowed over the years. Over the last three years, there’s been a deep commitment to making The Atlantic robust and exciting on the Web and having the Web component of the magazine be as important as the print component.

What’s your mandate? At the end of the year, what are you judged on?
Editorial success: Can we create a website that is editorially vibrant, that attracts readers, that plays a role in the national conversation, that occasionally breaks news, and that is constantly pushing forward the ideas and themes that are out there in the news cycle?

Is the bottom line part of your responsibility, as well?
Everybody here plays a role in making sure that the company is both an editorial success and a financial success. I don’t have any revenue obligations as part of my job, but I certainly participate with the business side in trying to make sure we’re a success.

How does that influence the editorial strategy?
I don’t think it’s that different [from print]. Editorial leaders have always been in conversations with business leaders. Our day-to-day writers, editors, and bloggers are not thinking deeply about the revenue side. They’re thinking deeply about making great content. To the extent that that great content attracts readers, that’s part of the definition of great content. That’s not the only way. [Great content] can [also simply] be important and advance the conversation [while not necessarily] being a reader magnet. But one way to judge our success is whether people want to read our stuff.

“When I was working on magazines, I felt like I could touch every single page… At a site like TheAtlantic.com, where we put up more than 100 posts a day, you have to surrender to the chaos.

What are some of your short- and medium-term projects?
The main thing we’ve been doing over the course of the last six months is to really build out “channels” — vertical sections of the site which we can bring on strong writers and editors to run and which also are attractive to advertisers who like to buy into sections of the site rather than just build around generic blog content. Over the last year or so, we launched a Politics channel, a Business channel, a Food channel, a Culture channel, and now a Tech channel. Continuing to vertical-ize the site is a focus for the next six months. And also to expand The Atlantic Wire, which has been a real success for us.

What’s been the biggest challenge you’ve run into so far?
The biggest challenge for me personally was making the transition from print to the Web. What I learned pretty quickly, but took a while to live with and accept, is that you lose control. When I was working on magazines, I felt like I could touch every single page. I read every story three or four or five times. I could touch every headline and every photo caption — multiple times. At a site like TheAtlantic.com, where we put up more than 100 posts a day, you have to surrender to the chaos.

What’s been surprisingly easy?
The skills that go into being a good print editor are completely transferable — editorial judgment, managing processes and people, setting editorial goals, and trying to move the enterprise to achieve them.

You’ve been leading the Atlantic’s digital editorial strategy for more than 18 months now. What are some things that have worked surprisingly well online?
Contrary to what we all think, long-form magazine journalism works very well on the Web for us. We routinely publish 6-, 8-, even 10,000 word stories on the website. It is not surprising for a magazine story to get a million page views. If you accept that people still believe in high-quality, long-form journalism, then they want it wherever it they can get it. Some people prefer to consume that in print. Some people prefer to consume news and information online.

iPhone, iPad — What’s your philosophy?
We’ve had iPhone apps out for the Atlantic Wire and TheAtlantic.com since late last year. We have a couple of iPad apps coming out. One is just the magazine. Another is a premium iPad strategy which will have magazine content, blog content — basically everything that the Atlantic is doing in print and on the Web. [Ed. Note: One of the iPad apps came out subsequent to this interview.] We’re on the Kindle. We haven’t met a mobile device yet that we’re not trying to figure out how to put our content on.

“Pay attention to how users are using the site or the app, rather than how you think they will.”

If you knew when you started this gig what you know now, what would you have done differently?
We did a major redesign of the site that came out in February. We would still do it, but we’d go into it with our eyes open even wider about the ambition and the gargantuan nature of it. You’re touching so many pieces of the site, not just the technology, but also the look and the journalists’ interaction with it. It ended up being a very big task.

When the redesign came out, The Atlantic’s Daily Dish star blogger Andrew Sullivan was vocal about the fact he thought it didn’t work for the site’s blogs, which he said had contributed mightily to the site’s success. What did you think of that?
We did a lot of things right with the redesign, and we did a couple of things that weren’t perfect. We have incredibly intelligent, opinionated bloggers, and they weren’t afraid to let us know what wasn’t working for them. We reacted very quickly and made some changes within 48 hours. And they were good changes to make.

The Atlantic has been recognized, in the form of awards, for the quality of its online site. What’s one thing you think more news organizations and magazines should be doing as they build out their digital offerings?
Pay attention to how users are using the site or the app, rather than how you think they will. Pay attention to whatever data you get and whatever studies you do. And be flexible enough to say, “We thought on the whiteboard that this was going to be the way it would work, but in fact our readers are saying that doesn’t make sense. So let’s move this module this way. Or, Let’s not do a carousel, but instead do three side-by-side photos.”

Last question: Do you ever have people downloading the Atlantic’s iPhone app mistakenly thinking it’s the Virgin Atlantic iPhone app?
(Laughs) No doubt we do. But they’ll probably be disappointed with our soundtrack.

NEXT >> 10 Tips for Pitching Multimedia Content

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E.B. Boyd is a freelance journalist based in San Francisco.

A year and change ago, Justin Halpern was just another 20-something struggling to find a toehold in Hollywood. He and his writing partner had sold a script for an independent film and had another one optioned, and they were hammering out a show, on spec, for Comedy Central. But for all intents and purposes, his bank account remained bone dry. So he moved back home with his parents, where he was once again subjected to the quirky harangues his father had doled out as he was growing up. Halpern started a Twitter feed for no greater purpose that to share those mumblings with his friends, while he concentrated on his day job at Maxim.com and focused on breaking into Hollywood as a screenwriter.

Fast forward a year. After the Twitterverse caught wind of Halpern’s unintentionally hilarious tweets, an agent came calling, and a book contract was quickly inked with HarperCollins. The book, Sh*t My Dad Says, came out in May and debuted at No. 8 on the New York Times bestseller list. In the meantime, CBS picked up a pilot for a half-hour sitcom of the same, though slightly modified, name, $#*! My Dad Says, which premieres September 23. Halpern tells mediabistro.com how it happened.

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Name: Justin Halpern
Position: Author, television writer
Resume: Author of Sh*t My Dad Says, co-executive producer of television show $#*! My Dad Says, senior editor of Maxim.com, and self-described “lucky son of a bitch.”
Birthday: Sept. 13, 1980
Hometown: San Diego, CA
Education: B.S. San Diego State University, 2003
Marital status: Engaged
Favorite TV show: Breaking Bad
Guilty pleasure: Top Chef
Last book read: Cloud Atlas by David Mitchell
Twitter handle: @justin_halpern

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When did you first realize your Twitter feed might actually lead to something much bigger?
At first, I didn’t even know how to check “@ replies.” I didn’t think there would be any, so I never learned how to check them. Then I figured it out and started scrolling through them. I was getting so many, and I saw one that said, “Hey, I think there might be a book in this. If you get this, please Direct Message me.” I did, and then I talked to the guy on the phone. He was like, “What do you think about doing a book about this?” And I was like, “I haven’t even told my dad that this is going on.”

What did your dad say when you finally told him?
He seemed not to really care.

So what happened next?
I asked the agent to send me a sample of a book proposal, and I said, “I’ll write one, and we’ll see if anybody’s interested.” At first, I didn’t even know if there was a book in this. If there was, it wasn’t going to be just a collection of tweets. That’s not a book, that’s a wall calendar. I just sat for a few weeks and came up with the proposal and structure of it and how I wanted it to work thematically, and the stories I had to tell. Even though it’s a silly little book about my father and me, I was attempting to tell a story and make it centered around, not just the father and son, but stories to have lessons to them. My agent sent the proposal out, and we eventually signed with HarperCollins.

When the book proposal went out to the all the publishing houses — it’s pretty incestuous, in terms of publishing houses and studios. They’re all kind of intertwined. A lot of producers got ahold of it. My literary agent started getting a lot incoming [calls]. My writing partner, Patrick Schumacker, and I took a few meetings for feature-length [film] adaptations. But I felt like I wasn’t the right guy for those. I didn’t know if I wanted to write a movie about this subject. It’s a small story. There’s not a large, high-concept to it. It’s very relatable, and, in a sense, mundane, in terms of what was happening in my life, and in my father’s life. So we asked ourselves if this was a TV show, and we started concepting it. We went around to the studios and said, “If you’re interested in the idea, we’d like to meet with show runners that you have deals with.” I knew no network or studio in their right mind is going to hand over a TV show to two 28-year-old kids who have no credits. And I wouldn’t have been prepared to take that thing to where it needed to go. I would have failed. So we met these two guys David Kohan and Max Mutchnik who had created a hit show [Will and Grace]. They were good guys. They just wanted to create a good show. And they wanted to mentor us. That’s what we were really looking for. So we partnered with them, and we pitched the networks. And we ended up signing up with CBS.

“The Internet has, in a way, democratized ideas. If you have one that’s really good, or you have a piece of content that’s really interesting, it can make its way to the top. “

It’s really interesting that, for each medium — Twitter, book, TV show — you haven’t just reproduced the content from one to the other, but really molded the general premise into something unique for each medium.
The Twitter site was just a happening. It wasn’t premeditated. It wasn’t thoughtful. The book was much more so. The relationship I had with my father was very similar to the ones my friends had with their fathers, and there wasn’t a book on the market that, I thought, was an honest depiction of a father and son. They were very syrupy with these really saccharine moments, and I just thought that was bullshit. (Laughs) It wasn’t my experience with my father, and it wasn’t any of my friends’. So I wanted to write a book that people could say, “Yeah, this reminds me of my father.”

With the TV show, it’s funny because the first thing [people asked me after he signed with CBS] was, “Why are you doing this on a network?” Instead of for a cable channel, like HBO. The first response I would say is, “I don’t recall receiving any calls from HBO.” (Laughs) But also, I told the honest story that I wanted to tell in the book. Any recreation of that on TV or in a movie is going to be a bastardized version of it. I thought we should do it a different way, so it’s not me trying to film versions of these stories on television. I thought we should do the best we can to tell fun stories that have that same kind of vibe and keep true to the character of my dad, but also break free of that and make it work for television.

Why do you think Shit My Dad Says has resonated with so many people?
I think my dad reminds people of someone in their family or someone they know. I also think, as a parent, there are so many times when you just want to tell your kid what you’re thinking, and you don’t, because the social conventions that are in place right now dictate that we don’t do that. It’s somewhat liberating that, if you can’t do it, to hear someone else call their kid a dumb shit. (Laughs) But I also think that my dad has a way with words. He’s a hyper-intelligent dude who has this really blue-collar element to him. I think it was a take on that that people hadn’t seen in a while.

What have you learned in the past year that might be useful to those wanting to follow in your footsteps?
The first thing I would say is that, on the Internet, people like stuff that is honest and has a kind of voyeuristic element to it. If you look at videos that are popular, they’re real slices of life. They show someone who’s being really genuine but also doesn’t know that they’re funny. Like the double rainbow video that just became gigantic. That guy doesn’t think that he’s funny. He’s not saying these things as jokes. He’s unintentionally funny.
Next, I’d say, keep creating as much content as you possibly can. If something strikes you as funny, or you have an idea for something, keep at it. Because eventually, hopefully, you’ll break through. The Internet has, in a way, democratized ideas. If you have one that’s really good, or you have a piece of content that’s really interesting, it can make its way to the top.

And last, I’d say when you’re in a position where you have a piece of content that other people want, try to think long-term. There will be a lot of short-term offers that sound really good but that will really kick the legs out from what you’re trying to do.

“Son, people will always try and f*ck you. Don’t waste your life planning for a f*cking, just be alert when your pants are down.” — Twitter.com/shitmydadsays

Like what?
When the Twitter feed was blowing up, I was getting crazy-weird offers to do stuff. This one hotel in Las Vegas wanted to fly my dad and me out and have us tweet at this pool party. My dad is 74. He doesn’t give a f*ck about a pool party. He’s not going to do that. And if I did that — they were offering a good sum of money — if I did that, anyone who’s following my Twitter account, they’d say, “This is so stupid. I’m not interested in it anymore. I’m not following it anymore. And, in fact, I actively hate it.” (Laughs)

There seems to be only a single picture out on the Internet of your dad. It’s at a ball game, and your dad and this young guy are looking at the camera, and there’s this other guy, off to the side, with his face mostly in shadows. It turns out that last one is actually you. Do most people think you’re the guy looking at the camera?
People do all the time, which is fantastic. (Laughs) My poor friend Brad. The British publisher, who’s publishing the book, for a while they thought that was me too. They designed a cover that had that on it. In a starburst in the middle, it’s Brad and my dad. I showed [a mockup] to my dad, because I thought it was funny. My dad didn’t think it was funny. He wrote this scathing email to Macmillan Publishers, in the UK, and he tore them a new asshole. (Laughs)

What pissed him off about it? Just that they hadn’t done their homework?
Yeah, it wasn’t even that they were using the wrong picture. I think he just thought it was lazy and half-assed.

NEXT >> How To Be Funny Online — Even When You’re Not

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E.B. Boyd is the Silicon Valley contributor to WebNewser.

You might wonder if Starbucks has gone off its rocker, given its recent announcement that it plans to roll out a digital content network in its stores later this fall. Content is expensive. There are more publishers than ever competing for the same number of eyeballs. And as anyone who works in publishing knows, the secret to making a dime on online content remains elusive.

But spend a little time talking with Starbucks digital ventures vice president Adam Brotman, who’ll be speaking at mediabistro.com’s Think Mobile conference in San Francisco tomorrow, and your skepticism might start to waver. The coffee chain has noticed that its customers increasingly reach for their mobile devices to cure what Brotman calls “micro-boredom.” So if they’re looking for entertainment online, why not have Starbucks — with its long history of curating music, books, and DVDs for patrons — serve it up to them? And when you find out that the company got rock-star publishers like the Wall Street Journal, Nickelodeon, and Apple to pony up premium content — for free — you just might begin to think the coffee giant is on to something. Mediabistro caught up with Brotman to find out about the big breakthrough idea behind the Starbucks Digital Network, whether the network’s success is contingent on the rise of paywalls, and what he learned from his famous entrepreneurial uncle.

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Name: Adam Brotman
Position: Vice president of digital ventures, Starbucks
Resume: Founder and CEO of PlayNetwork, 1996-2006; senior vice president of Corbis, 2006-2008; CEO of Barefoot Yoga Company, 2008-2009. Joined Starbucks in 2009.
Birthdate: September 20, 1969
Hometown: Mercer Island, WA
Education: BA from UCLA in Classical Civilizations and Business & Marketing. JD from the University of Washington Law School.
Marital status: Engaged
First section of the Sunday Times: Sports
Favorite TV show: Monday Night Football (or any football on TV)
Twitter handle: @adambrotman

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Many companies are struggling to make online content pay. So what’s the big breakthrough idea behind the Starbucks Digital Network?
The unique combination that Starbucks is able to bring together for its customers to give a win-win-win is what makes this different. Starbucks has a bunch of unique assets. There’s our brand, our baristas, and our product. However, we also have hundreds of millions of customers coming into our stores every month. We have a huge footprint. We have this amazing “third-place” experience that we’ve built up. We’ve become known as the place away from home and work where you can go, collect your thoughts, meet a friend, connect with a barista, relax, and recharge. And on top of that, we have a history at Starbucks of curating and recommending content — whether it be books or music or newspapers. Our customers really trust our taste.

So how does this all come together?
We went to the various content companies that we wanted to hand-select for our customers, based on a lot of talking to our customers and based on the kinds of content they’d be interested in. And instead of charging them for access to our customers — and many of them would love to have access to our customers — we said: “Why don’t you provide something of value that they can’t get for free on the Internet, or that they can’t get at all because you make it a ‘sneak peek’ or exclusive to us.” That differentiates the content for our customers, but it still gives these content partners [the ability to raise] awareness [among Starbucks customers] and [have those customers give their content a] trial within our stores. Then we share revenue on the upsell, so we become like an affiliate network.

“We win because we’re enhancing the customer experience, and we’re doing so in a way where everybody’s happy to be involved in the transaction.”

So how does that produce the win-win-win you talked about?
We give this great awareness and trial benefit to our content partners. We win because we’re enhancing the customer experience, and we’re doing so in a way where everybody’s happy to be involved in the transaction. Hopefully, most of all our customers.

What’s the mobile angle to this?
More of our customers access Wi-Fi in our stores through mobile than they do through laptops. So we designed the site to be a seamless experience across different devices. The design of the site is meant to be easily touched and swiped. It works really well with a mouse, but it works just as well with your fingers on an iPad or iPhone.

Also, the site is a location-based site. It knows what store you’re in. So we can do a number of location-based features and engagement points on the Starbucks Digital Network that you normally would associate with a mobile phone. For example, we can work with Zagat to provide full, unrestricted access to their subscriber ratings for restaurants that are right near the store you’re in. Or we can work with Rodale — Men’s Health, Women’s Health, and Runner’s World — to come up with biking and running routes that start and stop at the very store that you’re in. We can even provide weather reports, down the latitude/longitude of the store. And we’re doing a lot of community-involvement services, like our work with DonorsChoose.org, where you can fund public school projects that teachers have posted at schools right next to the store.

It seems like you’re moving the idea of what constitutes “content” forward as well, developing stuff that can be consumed in brief “interstitial” moments.
I’ve heard it called “micro-boredom.” Particularly at Starbucks. You’re in line, or you’re waiting for your latte, or you’re waiting for a friend to arrive, or you’re just drinking your latte and you’ve got 10 minutes. A lot of time, people will pull out their phone and check email. Maybe they’ll want to learn something or discover something because they’ve got a few minutes. That’s happening in our stores a lot.

So will the content be optimized for the person who’s just got 90 seconds or 10 minutes, rather than a longer stretch of time?
Sort of. We are designing the content experiences to be “snackable.” If it’s a free iTunes pick-of-the-week digital download, that is something you can get done in 90 seconds or less. You can check out The Wall Street Journal for free and the New York Times e-edition, which you normally have to subscribe to. Those are very snackable. But if you’ve got an hour to kill and you were going to be online anyways, we hope that we can provide an interesting alternative to what you were going to do anyways on our free Wi-Fi.

Will people be able to take any of the content with them when they leave?
Some of the offerings will be downloads, like the iTunes pick-of-the-week.

“‘Premium’ doesn’t have to just mean you have to pay for it. It could be a window of an exclusive.”

Some observers have said the success of the Starbucks Digital Network is contingent on paywalls going up at content sites that are currently free. Is that the case?
No. We don’t know what’s going to happen in terms of paywalls. We’re pretty agnostic to what happens there. There will always be the desire and the ability to create premium content. But “premium” doesn’t have to just mean you have to pay for it. It could be a window of an exclusive. For example, right now [with ebooks], you can preview the first chapter or two of a book that is already in print before you buy it. When we work with publishers, we’re looking to say, “Let us have a preview before anyone else has a preview.” So that makes it premium for our customers. When we work with magazines and other publishers, we might say: “Why don’t you create something interesting just for us, by repurposing something that you’re doing, or at least give us the first crack digitally, for the first week, where you can only get it via the Starbucks Digital Network, before it goes on to your website.”

The Starbucks Digital Network is a curation play, and curation plays depend heavily on the curator. Who’s your curator and why do you have faith in them?
It’s a curation play, but it’s really a customer experience and engagement play. We’re not looking at ourselves as some grand arbiter of taste. We’re more focused on: What is our brand? What is the customer experience in our stores? And what makes sense for us and our customers around content and engagement?

You joined Starbucks a year and a half ago. What was your mandate?
Be entrepreneurial. Make sure to be innovative in how my group leverages Starbucks assets. Be nimble. Be humble to our customers and our brand.

Why did Starbucks decide they need more entrepreneurialism inside the company?
I have to give a lot of credit to my boss [Starbucks CIO] Stephen Gillett. He and [founder and CEO] Howard [Schultz] and the leadership team came up with the idea that there are certain activities — particularly in the digital sphere — that shouldn’t ladder up directly to traditional IT or marketing, that are more about engagement and innovation than other marketing activities. They believed that if we set up a group that worked very closely with marketing and public affairs and operations, but was tasked with being innovative and entrepreneurial, and leveraging opportunities with innovative engagement with our customers, that that could hopefully unlock some results that are harder to achieve otherwise.

Your uncle Jeffrey Brotman co-founded CostCo. The customer experience at CostCo is the antithesis of the experience at a place like Starbucks. Did he give you any advice that was transferable from running a large discount chain to operating intimate coffee shops?
The two companies share a passion for understanding what the customer wants and expects. My uncle has always mentored me to focus on the customer and focus on the customer experience. CostCo has always impressed me as a company that understands that the customer wants great product in a no-frills environment. If you boil it down, both companies are equally passionate about what the customer wants — and about the core competency of the company. And so whether it be at PlayNetwork, or Corbis, or now at Starbucks, that’s a lesson that I’ve always taken to heart.

See Adam’s presentation on how Starbucks Digital Network is harnessing content partnerships and location-based services at our Think Mobile conference September 23 in San Francisco.

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E.B. Boyd is the Silicon Valley contributor to WebNewser.

After graduating from the University of Oregon in 1996 with a degree in Sports Marketing, Mark Sacks spent the better part of a decade working for two of the world’s biggest brands, Nike and Starbucks. In late 2004 Sacks detected what he calls “the brewing of a perfect storm.” With almost no knowledge of Internet technology, Sacks moved to Creative Artists Agency to work in new media and corporate consulting. He explains why technology is changing the face of entertainment and what marketers must do to keep up, detailing how he became a new media agent.

Up until two years ago, you’d spent your entire life studying and working in marketing. What led you to believe there was about to be a major change in the business?

I was at Nike during an incredible period of growth and transition for the company. I was responsible for our advertising, sponsorships and event marketing in the Southwest United States, with our primary focus on the NikeTown stores. The goal of these stores was to educate, inspire and entertain the costumer. We were using them as three-dimensional expressions of the Nike brand. They weren’t so much “stores” as Nike museums. It was the beginning of “retailtainment,” leveraging people’s passion for sports and entertainment to connect with them on a visceral level.

When I arrived at Starbucks, I was struck by the fact that while we were a coffee company, we were also providing a community gathering place where people could come together to connect and discover new things. Our customers gave us permission to be part of their entertainment discoveries because of the trust they had in our brand. Starbucks started with Hear Music, and now they have a 24-hour digital music channel on XM Satellite Radio, books, magazines and a partnership with Lionsgate [when they helped] market and distribute the film Akeelah and the Bee.

What became clear to me is presence is not the same at relevance. Just being in front of people stopped being meaningful. There was too much clutter, too much noise. Everything I was seeing and experiencing pointed to a perfect storm of change in the worlds of brand advertising and marketing, and across the media and entertainment landscapes.

How did you connect this “storm” with technology and entertainment?

By this time, it was becoming pretty evident to most people in the industry that technology would turn the existing business models on their heads. Technology was putting the consumer in the driver’s seat and giving people the power to choose when, where and how they consumed marketing and advertising messages.

The idea behind advertising used to be, 1) identify your target audience, 2) figure out when and where they are consuming entertainment, news or information and 3), interrupt their experience with your message.

Time-shifting and place-shifting are general ways to refer to the benefits of technologies like Tivo, iPods, Sling Box, Xbox, AppleTV, Moxi, MobiTV and GoTV. Collectively, these technologies and devices let consumers watch on-demand content when they want, where they want (cell phones) and even how they want (i.e. commercial-free).

Now, with people time-shifting and place-shifting and taking full advantage of ad-skip technologies, that model was broken. The message itself needed to be compelling enough that people would choose to watch it. As an advertiser or marketer, to be effective, you had to be able to turn your marketing into entertainment and entertainment into marketing.

What do you mean when you say technology is changing the face of entertainment?

When television is delivered as a digital signal over an Internet connection, the content itself can be manipulated. When television was delivered through antennas, each station was limited to one macro broadcast. What you watched was exactly the same as what your friend across town watched.

Now, with digital television delivered to set top boxes, the paradigm shifted. Content can be targeted based on geography, which is particularly important for advertisers. You and your friend can still watch the same program, but now the ads can be different, based on where in town each of you reside.

If advertising can be targeted to individual set top boxes, then why can’t programming? Television of tomorrow will programmed like your iPod and the ads you get will be very personal to you.

CAA reps some of the most famous, successful celebrities and artists in the world. Why would a Web site need an agent?

Along with actors and actresses, CAA represents writers, directors, producers and executives across music, TV, gaming, movies, theater, all forms of entertainment. We work very closely with production companies, movie studios and TV networks.

Whether it’s Brad Pitt, Jennifer Aniston, Bon Jovi or Will Wright [a video game designer], we know our clients intimately, so we’re ideally suited to looking out for their interests, minimizing their risks and maximizing their upside for any endeavor they invest their time in.

The same principles that guide us in representing individuals apply when we’re representing companies. Whether you’re talking about established brands like Coca-Cola, Sprint and Harley Davidson or new media companies like Joost.com or iMeem.com, we’re keeping the big picture and their long term objectives in mind and making sure their good work is famous.

As far as New Media, we represent content creators like YoungHollywood.com, content distributors such as Joost, and social networks like iMeem.com. It makes sense for them to come to us, and for us to represent them, because executives in my building are on the phone every single day with Les Moonves, Sumner Redstone and all the other presidents and network heads. Eventually, these Web sites will do deals with these people. We can help them obtain and maintain the right contacts. They benefit from our access.

What are you working on right now?

I’m excited about TV 2.0 and mobile 2.0. The changes going on in these two spaces will change so much of how we experience news, information, entertainment and even each other. When you combine the interactivity of Web services we’re getting on the Internet right now, with the trend toward on-demand and anywhere viewing, you start to get a sense of how significant and meaningful these changes will be.

What’s a typical day like for you?

The last thing I do every night before leaving the office is establish a game plan for the next day with my assistant. Then, the next morning, as soon as I’m in the car, we start making calls. Often, I have a breakfast meeting before getting to the office, so we’ll try to make as many time-sensitive calls as we can before those meetings even start. [My assistant] keeps the ball rolling while I’m in that meeting and then, as soon as breakfast is over, we get back on the phone and pick up where we left off. The rest of the day pretty much goes the same way.

How many hours a day do you spend on the phone?

More than I’d like to admit. I probably make and take no fewer than 60 or 70 calls a day. So much of our business is based on relationships and early access to information, it’s critical that networking be a part of every day’s agenda.

The assistants help with “rolling calls.” As I’m wrapping up a discussion, they’ll get my next client on the line so I can move on to the next piece of the business. I also get between 150 and 200 emails a day. I’m happiest when I leave the office and there’s no more than a screen’s worth of emails in my inbox. I try to get to fewer than 10, but it always seems to fill back up by the time I hit the Blackberry before dinner.

Our new media clients are so passionate. The work they’re doing is revolutionary. I want to be right there by their side all day, because I really believe in what they’re doing.

How long does it take for someone to become a client of yours?

It really depends on the agent or team who will be signing the client. Some signings take weeks and some take years. More than anything else, trust has got to be established and expectations must be consistent for everyone involved. I like to work with someone for awhile before signing them. I can’t work with a person unless I trust them. The client needs to know my working style. When I ask for something, I expect them to deliver. I don’t have time to waste with people who aren’t getting their stuff done. [Potential clients] usually have been emailing with me for 6 months to a year, even over three years.

What are the benefits of high-tech entertainment?

The definition of community is so different than it was 3 years go. MySpace, LinkedIn, YouTube. There are 80,000 new blogs a day! People are relating, helping, changing each others lives and they’ve never met each other. Services like Wikipedia have democratized information and made it accessible to everyone. The web is facilitating interactivity-on-demand and personalization. Customers want to get services when they want, where they want them, how they want them. Technology has leveled the playing field. You can be a millionaire or a guy in a garage. Over the last couple of years, I’ve learned if I can think it, it can happen.

You’re dealing with so many new, cutting edge companies and Web sites. Is it challenging to be on top of everything all the time?

The greatest challenge for me is, and always has been achieving a sustainable work/life balance. There’s way more to do that I just can’t possibly get to. When you’re working at a place like [CAA], opportunities and access abound. There really aren’t any doors we can’t open. It’s tough to know when to say, “No.”

Honestly, I would do more in a day if I could. Our new media clients are so passionate. The work they’re doing is revolutionary. I want to be right there by their side all day, because I really believe in what they’re doing.

Were you computer-focused before you came to CAA?

No. In fact, being interested in technology is really new for me. Two years ago most of the new media companies we’re working with and that are defining what will be possible tomorrow, didn’t even exist. What got me in the door [at CAA] was I understood the importance of marketing.

There a lot of TV shows out now that highlight the role and experience of assistants at big companies. Ari and Lloyd’s relationship from Entourage comes to mind. How important is your assistant?
Important.

Could you survive for a week without him?
Yes. But it would not be pleasant.

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Four Things to Know If You Want to be an Agent:
1) You’re going to start as an assistant.
“You’ll learn what the business is really all about, how relationships are cultivated and how to gain access to information,” Sacks says. “Then, if you’re doing a great job, you’ll get promoted to the mailroom.”

2) The mailroom is where meaningful professional relationships develop and solidify.

“People bond over the shared experience and they gain an even deeper understanding of the business and the agency while they’re there,” Sacks says.

3) Don’t believe everything you see on TV: Agents should remain realistic.

“Be honest when it comes to work,” Sacks say. “Always under promise and over deliver.”

4) It’s easier to drink the Kool Aid when you and your company share similar values.

“When you’re at the right company, it ends up feeling like family,” Sacks says. “The work I do is very meaningful to me. We only have so much time in life and I’ve figure out I want to make my part count.”

Stephanie Burton is a New York-based freelancer.

Born of founder Ben Lerer and his buddies’ need for better date spots, retail guidance, and watering holes, Thrillist launched in 2005 as a daily newsletter committed to keeping New York’s 20-something men in the know. Each day’s installment boasted (and still contains) one key tidbit on the best outlet or location offering an interesting product or an unusual experience. In under two years, the e-newsletter has begun influencing countless more men with the launch of versions in Los Angeles, “Nation” (so guys stuck in the middle stand a chance at matching their coolhunting coastal counterparts), and most recently San Francisco. We sat down with Lerer to discuss the highs and lows of expansion, and how tough it is to find his patented “Thrillist guy” in Chi-town.

Describe your exact role at Thrillist these days: What’s your day-to-day like, versus what it was like when you first launched?
I guess it’s probably changed a lot. Personally, I used to have a daily deliverable. There were certain things I was responsible for doing on a daily basis, whether that was ad sales, accounts that I worked, people that I worked with, or in editorial. There was a time when I obsessed over every line of every piece that went out. Now that we’ve been growing, my role has changed a little bit because I’m not as obsessed with all the little details. Although I’d like to be, it doesn’t make sense. I’ve broken the company into four divisions, with technology and content and marketing and sales. My role now is just kind of making sure that the people who run each of the divisions are happy and having fun and we’re still kicking butt.

Who’s obsessing over all your editorial these days?
Adam, who’s my partner from the beginning. He’s the editor-in-chief now. It’s funny: he’s kind of grown into an editor because when we started, neither of us had any experience in editorial, and now he’s gotten really good at it — more than really good. Now he has really become the direction of the voice, and he’s the top editor at the end of the day. Most of the editors choose topics and make sure that we stay consistent between the cities, voice-wise. Then we have an executive editor named David Blend who was our New York editor for the first two years, [who] really came in and taught Adam how to take what was in Adam’s mind and put it on paper. [David] has been kind of a driving force on the editorial side and someone we kind of love desperately, and who has been incredible from the beginning. Each of the editions has one editor, so when we launched San Francisco we had brought in a guy Patrick Heig — he’s our everything in San Francisco. He’s the guy who runs the show out there, picks all the topics, who hires the freelancers, who works with the tipsters, who works with the PR companies, and he’s become the face of Thrillist in San Francisco. We have the same thing in L.A., same thing with New York with Steve [Bryant], and the same thing for our national edition, with a guy named Ben Robinson, who is also somewhat new — he’s kind of our national editor. He’s based in New York as well.

So, Patrick in San Francisco. How did you find him?
There’s a magazine in San Francisco called Todo Monthly. It’s a kind of hipster magazine that comes in the back of taxis — it’s a little hand-held kind of book — and he was a writer there for a few years. Adam went to high school with a guy named Michael Moskowitz, a great guy out in San Francisco who’s the founder and the publisher of Todo. Michael said, ‘I’ve got this guy Patrick, writing for me for years, and I don’t have a full-time thing for him and frankly I don’t think he wants to write full-time for me, but I think Thrillist is the kind of thing he could wrap his head around forever.’ He is as natural a fit as I could ever find, that I could ever imagine for any job in the history of the world. Everything about him: He looks the part, sounds the part, he sounds like a Thrillist guy. Hanging out with him, he’s what Thrillist is all about. We’re really lucky to have him.

That prototypical Thrillist guy: What does he look like, sound like?
I think the idea is you’re young, you’re hungry, you’re hard-working, you’re pretty smart. You work hard, you play hard. You, sometimes you have to wear your suit, and get all dressed up, but you probably prefer to be sleeping on the sofa watching football. A guy you went to college with or you went to grad school with.

How did you pick San Francisco as the next market for Thrillist? After launching New York, national, then L.A. editions?
We went national second, not necessarily because we thought that national was the next strongest market for us, but because we were kind of scared of letting the voice out. National we could run from New York and keep a very close hand in what was going on, and make sure that the consistency was there.

So it was strategic?
Exactly, as far as training an editor, and just getting the voice, being able to replicate the voice, when it wasn’t just David writing and Adam editing. Now that the structure was going to change, [it was] trying to find just how to train the person, how to recruit the right person for the job, and how to develop a network of contacts that, if we were doing it in L.A. first, would have been a little bit out of our league. We went to L.A. second, kind of blindly. We just said, “Why not L.A.?” It seems like the natural move, since L.A. and New York are the two biggest cities.

San Francisco was a little bit more strategic: One reason is that Adam is from San Francisco, so it was not as far from home in some ways as it might seem. Also, it’s a city where we saw that there was a real hole, media-wise, for anything like what we were doing. Daily Candy is obviously out there doing their thing, they’ve had a lot of success there. There are a lot of people working in technology and media out there, with Apple and Google. We thought that in New York, we’re really strong with that community — same goes for L.A. — and we thought that that kind of a guy would be into what we’re doing. Also, we’re out on the West Coast a lot. For business purposes, it’s a short trip. It’s easy. So Chicago is next.

When do you expect to launch in Chicago?
We don’t know. We’re ready from a technical standpoint and we’re ready from an advertising standpoint. I think [with] content, we just want to make sure we get San Francisco very comfortably on its feet before we take the leap [to Chicago].

Do you have an editor yet for Chicago?
We don’t quite have our editor, we’re looking around. In the past, we’ve hired people when a job opportunity presented itself: We need a new salesperson, we need a new this, we need a new that, and we’ve hired not necessarily the first person we’ve found, but one of the first people that had the right kind of experience on paper. This is the experience of starting a company when you’re a little kid: [When hiring] you have to know deep down if it’s the right guy or it’s not the right guy. We’ve met a lot of cool, confident people in Chicago, but we want to wait until we find the guy who [is] so Thrillist, they just live and breathe it, and they’re someone who we are really proud to have representing the brand.

Does the challenge of finding your Chicago guy have anything to do with the Chicago market itself?
I would never have said yes until I started to talk to people: Yes. There must be something in the water there. I don’t know exactly why we’re having so much trouble finding a really good Chicago guy, but it could be there’s something bizarre in Chicago and it could also be that we’re getting better at knowing what we want and we’re being more particular: The skill set needs to be more exact, and it needs to be a better fit. In the past we’d just shoehorn people into jobs that weren’t necessarily perfect. Now, we’re able to be a little more deliberate in everything we do and I think [hiring in] Chicago is maybe the first time that we’ve really been quite so careful.

We didn’t interview 60 people in San Francisco — we interviewed five and we met Patrick and it was great. We’ve interviewed a lot of people in Chicago, and we haven’t found a perfect fit. Although we’ve met with tons of really talented, really funny, really interesting people, no one has been Thrillist.

We’re only as good as our next piece of content.

You’ve said before that expansion was a possibility when the number of subscribers hit a certain threshold. What did it take, subscriber-wise, to be able to move forward with new editions?
I think it’s less about that now than maybe it was. I don’t even know what the number was, but the idea was about proving the concept in the city before it. We didn’t want to launch the Nation until we knew that New York had worked. We didn’t want to launch L.A. until Nation had steam behind it — we felt like it was really cooking, people were liking it, the product was working. Same goes for San Francisco.

Now we’ve been able to replicate success in several cities because we’re finding the local people there. It’s not about us, it’s about them once we get to the city. We have a nice model and a nice voice, but ultimately it’s about finding the right editor who really just gets it, and understands the city and what people want in the city. I think now we know we’re going to be successful in San Francisco. We know it’s going to work there because we have a great editor, and I think the voice works for the city and we’re finding cool stuff. San Francisco is just an awesome city with a lot going on. There’s just so much cool stuff to discover, and it’s kind of wide open for us.

So, would your direct competitors be San Francisco Magazine and the aly-weeklies?

Those, or city guides. Absolutely.

We never like to think in terms in competition. All that competition is going to do is bog us down and get us worried. It’s a waste of time for me to think about it — we just have to focus on doing the best job that we can do, and not getting caught up in the little details of other people trying to eat our lunch, because it’s just going to drive us crazy.

Describe why this approach works in an online format versus a print format? You guys are daily, and very granular about what you’re choosing; it’s interesting that there seems to be an opportunity online where there isn’t in print.

First of all, everyone is online right now that we’re going after, so it’s a natural fit. The cost to start something up online is so much less than the cost to get something started up in print, so we never even conceived of print early on. Maybe in kind of a pipe dream, but it was never a realistic opportunity, so online was the only place, and I think that it works.

I think the success of Thrillist is based on email, not just online. It’s a habit. Email is a personal thing, it’s a habit, and getting invited into someone’s email box is such a great way to communicate with somebody that I think a lot of Web sites don’t necessarily see. If you’re a Web site you have to remind people — you have to use more marketing to remind people to come back and check you out. With us, if somebody finds us once and decides it’s really interesting, we’re going to come and remind them that we’re around every day. If we remind them often enough, and they don’t like what we’re doing, they will very quickly remove us from their life, which is fine with us, it keeps our list tight, and it keeps it with the people who are signed up for Thrillist are the people who want Thrillist.

What have you covered that has engendered major reader response, positive or negative?

Just very recently in San Francisco, we wrote about a woman who takes old clothing that you have — old jerseys or old t-shirts, things that are no longer wearable — and makes new clothing out of your old stuff. [She] kind of brings it back to life and makes hoodies out of it, and makes new t-shirts, and other cool things. It was a really interesting one for us because, typically, we move the needle so much more for people as our list grows. As we’re in a city longer, we have more people reading, so when we write about things more people respond. But, this was our first or second piece in San Francisco, and we had 4,000-5,000 people reading that day. We ended up really changing this woman’s business in one day.

We did it and she got a lot of pick-up from other places, and that kind of viral effect really took hold, and now the woman can’t fill the orders she’s been getting. It kind of changed her business from what she told us, which is really exciting because it was very early in the edition. We did move the needle in the first week — it was good for Patrick, it kind of got him really energized, so that’s a recent success.

This is an embarrassing one: We wrote about this shirt that looks like you’re wearing tattoos. It’s like half-see-through, a really silly, funny shirt that I saw someone wearing out one night. I thought it was really funny, and I showed it to the editors, and we thought it was really funny. We didn’t actually recommend it as something that you want to go out and buy, it was more of a Halloween costume, but we featured it on Thrillist Nation, and we got skewered by everyone from Gawker to Vh1 online to Best Week Ever, just ripping on the shirt and us for writing about it. I completely understand where they’re coming from, because there is that inherent recommendation [in covering it], there is the endorsement there, but sometimes we’re writing about something that we think is funny rather than really cool.

Do you still have a book project in the works?

We don’t have a book project in the works. We’ve been approached. Right now I just don’t know what our book would be about and I think that that’s a bad way to start a project. We started Thrillist because we wanted something like Thrillist to exist. We were frustrated that there were a bunch of crappy city guides. Trying to diversify Thrillist into a book when we don’t have a passion to write a book about something would be a mistake and would just be kind of greedy of us, in trying to extend the brand and to create like some Thrillist guide to something that we don’t think would really deliver value to people. At the end of the day, that’s what Thrillist is about, it’s a service; we want to provide value. We want people to be able to walk away and feel like they got something out of reading Thrillist. Unless there was something we naturally thought would be a good idea, and we really wanted to do, we wouldn’t do a book.

Any other projects in the works?

Not really. We’ve kind of had our heads down. We’re trying to do one thing really, really well. The expansion we’re looking at is geographic expansion first and foremost: As much as we want to keep growing to new markets, we really want to focus a lot of our attention to making sure that what we currently have is great, because we’re only as good as our next piece of content. We want to make sure that what we send out to our current readers on New York and San Francisco and L.A. and Nation is great.

Have you gone through any fallow period, maybe transitions between editors, when interest waned?

I can’t necessarily pinpoint it with any user metrics. Growth has never slowed — growth has only gotten faster and faster as we’ve grown, and the response has only gotten bigger and bigger. The only time where we’ve ever been able to pinpoint anything like that is internally, when we’re reading.

The company is a pretty good focus group. There are 13 of us, and we’re all in the demo: we’re all between 25-35 and living in New York or L.A. or San Francisco and we’re young guys. Aside from the editorial staff, if we think the content is taking a little bit of a step back, we let the editorial guys know.

We recently made a big transition, where our Nation editor left, and we had a new Nation editor come in, and our New York editor left to become the executive editor, and we got a new New York editor, and we launched San Francisco. So our staff went up with three new people. It was a really big change because it takes a long time to get the voice, to get familiar with the format, the deadlines and the way that everyone works. So it was tough — It was about a month and a half ago or two months ago where everyone was working many, many more hours a day than ever before. Now we’ve kind of settled back in to a good system and everyone is happy again, but we’re always trying to improve and we always find — once a week, in at least one edition — there’s a piece that afterwards people in the office are like, “That stunk.” We try not to let it get us down when we don’t print the best thing we’ve ever printed. In general, I think four to five days we’re sending out really, really great stuff. You don’t need to hit a homerun every day, you just can’t strike out.

Do you ever worry that you might enter a market and saturate it — hit the bottom of the barrel as far as new things to cover?

I’m definitely nervous about it. I don’t think we’re ever going to run out of stuff in New York or L.A., or San Francisco. I worry that there are other cities around the country that may not be able to sustain it. I’m not sure if we can do five days a week in Seattle or Atlanta. We’re not necessarily married to a daily model in every market we’re in if there’s not enough stuff. In New York, I think there are five great things a week, whether we find them every week is another story. Sometimes we don’t find all five things — we do our best to — but I think there’s always going to be enough content. A friend of mine is a big restaurant foodie guy, starting a food Web site. He was telling me that he’s trying to pinpoint the top 1,000 restaurants in New York, and he has a theory that there are never more than 1,000 great restaurants in New York City. I was saying, what about when a new place opens? He was like, “I guarantee you a place that was in your top 1,000, a place closes.” There is so much turnover in everything.

There’s always new stuff popping up [in our current markets], and we’ll have a neverending supply of content. I don’t think the well can run dry, but in other markets, there may never be enough. So we need to be very careful before we make a commitment to a city that there’s enough. When we launch a new city, we actually launch four days a week rather than five, to give ourselves that day of rest, and that day to be sure that we don’t put that pressure on ourselves early on. We want to be sure that there’s a solid four, that everyone’s happy, and that there’s almost more that we want to cover. We want to get the contacts in place and the freelancers and tipsters, so that there’s too much, that there’s not enough days in a week, and when we get there, we know it’s time to go to five.

What would you say is the most challenging aspect of growing Thrillist?

Entering new markets, I think the most challenging aspect of any of this stuff is a) hiring the right person, and b) just for us, emotionally staying strong and staying focused and looking at this from a long-term perspective. We’re growing this thing and we’re really trying to do the best stuff and not letting one day of content that we’re not in love with make us sad throughout the next day. Just staying focused on doing as good a job as we can, and knowing that we can’t be perfect.

Have you ever had to let anyone go?
We have. There have been a few people that didn’t work out for various reasons. It’s not fun. It’s an awful, awful, awful thing, and everyone who has worked for Thrillist we brought in because we obviously thought that they were great. There aren’t any who left that we’re on bad terms with, I don’t think, but sometimes someone’s not quite right.

It’s really very sad and unpleasant. It’s something that we really don’t want to do, which could be part of the reason we’re so careful with who we hire.

How do you cope with that from the standpoint of a relatively young professional who is responsible for this larger organization, including the morale and the direction of the group?
I rely on the investors a lot to give me advice and help to lead me through those situations and handle them in the most professional way possible.

I haven’t had that many jobs. I’ve never been fired from a job before. So, just going through the process of the way you’re supposed to do it and the way you’re supposed to be sensitive: asking [the investors] about the potential questions people ask, the worries any employer has for somebody who’s not going to be there anymore, from a security standpoint to an emotional standpoint, for the person and for the morale of the team.

We really do try to have a team aspect all the time so it’s not at all out of the ordinary after something like that happens, we have a team meeting when everyone can talk about how they feel. The culture of the company is so much of what we’re about and what we do. Letting somebody go can really shake that, so we’re really careful that everyone understands why decisions get made.

Are there any things that have changed in your day-to-day role that you’ve had to let go that you’ve been sorry to part, work-wise?

I loved reading the pieces, but at the same time, it’s stressful. It’s a big time commitment and it’s tough.
Other than that, I don’t really miss any specific thing. I miss the idea of having daily responsibilities and feeling worthwhile. Today, I feel like I didn’t get anything done. There are so many days now where I feel like I didn’t get anything done because I don’t have anything to show for the stuff that I’m doing necessarily. I miss that a little bit, coming home, being like, “I did something great today,” rather than, “We did something great today.” But, I can definitely settle for “We did something great today.”

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Tips on taking your venture into new markets:
1) Have realistic expectations.
Sometimes things don’t go as planned, and sometimes you look back and wish something had turned out differently. “You don’t need to hit a home-run every day,” Lerer says. “You just can’t strike out.”
2) Play with the model.
“We’re not necessarily married to a daily model in every market we’re in if there’s not enough stuff.”
3) Lean on the experts.
Lerer says sometimes, he needs a little guidance. “I rely on the investors a lot to give me advice and help to lead me through those situations and handle them in the most professional way possible.”
4) Appreciate team successes.
With the expansion of the business to new editions, Lerer’s had to trade individual responsibilities for ones benefiting his organization. “I miss that a little bit, coming home, being like, ‘I did something great today,’ rather than, ‘We did something great today. But, I can definitely settle for ‘We did something great today.'”

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[Rebecca L. Fox is mediabistro.com’s managing editor.]

Imagine you started a brand new magazine last January. A year later, you’ve managed to attract 30,000 subscribers, and at least 200,000 people are picking up individual copies at the newsstand, with many hundreds of thousands more paging through your publication at the checkout line. Not only that, the magazine is already in the black. And all without mentioning a certain pantiless pop star. Sound far-fetched? Not if you’re Leo Babauta, the author behind Zen Habits, the rookie blog sensation of 2007. OK, it’s not a print magazine. But in this brave new world of online media, it could very well be the next best thing.

Babauta, a veteran staff and freelance writer, started the blog at the beginning of 2007 as nothing more than a personal journal about simplifying his life. At first, family and friends were his only readers. But word about the blog started to spread. Visitors stopping by for a look found themselves getting hooked on his soothing prose and insightful advice. Other bloggers started singing his praises. The numbers kept mounting. And by October, Zen Habits had achieved the near-impossible: It cracked the Technorati 100, the list of the most popular blogs in the world. Today, the blog is in the Technorati 50. (For those who’ve lost track, there are at least 100 million blogs out there. And counting.)

Over 30,000 people subscribe to the Zen Habits RSS feed, and that number will surely rise — it’s already up from 24,000 a month ago. In December, Zen Habits received 800,000 unique visitors, with 200,000 of those returning more than once. (For comparison, the Drudge Report received 1.3 million unique visitors that month, according to a recent article in Portfolio.) The blog, which makes money off advertising, is doing so well that Babauta, a modest, 34-year-old father of six who lives on Guam, is now quitting his job as a legislative analyst to devote himself full-time to the blog, as well as to a new online business venture, and … drum roll, please … a brand, spanking new book contract.

mediabistro.com caught up with Babauta to ask him how he went from being just another Joe Blogger to one of the leading Internet scribes, and a self-supporting one at that — all in a single year.

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How did the idea for Zen Habits come about?

I had a great year in 2006, making some amazing life changes, from quitting smoking to training for and running my first marathon to starting to wake up at 4:30 a.m. to getting my life organized to eating healthier and simplifying my life to doubling my income and starting to eliminate my debt. Accomplishing goals like this, and creating a series of new and positive habits, it’s something you want to share with people. So I created a blog, most of all to post my goals and hold myself accountable for them, but also to share what I learned along the way with others. It turns out that there were a lot of people like me, looking to make similar life changes.

When you started, were you trying to create something that would have a wide readership and would become well-known? Or were you just creating something for family and friends?

It was mostly just something for myself, and family and friends, but there were points in the beginning when I was reading other blogs and thought to myself, “I can do that!” I mean, I read some great blog posts, but they weren’t anything that I couldn’t write. I felt I was as good a writer as most bloggers out there, and that I had a lot of things to share too. So I wrote some early posts with the desire to learn the new medium of blog writing (which is different from other forms of print journalism), and to see how well I could do it. When I thought I could do it well enough, I started to share links with others, and it just took off from there.

At what point did you realize the blog was becoming bigger than just one guy’s personal journal?

There wasn’t one point. The few early visitors to Zen Habits just loved my posts, and it encouraged me to try more. The more I wrote, the more people came, and the more positive the reactions were. I mean, these were extremely positive, praising reactions. It was very encouraging.

What did you start doing differently, once you realized you had a real audience out there?

Every writer, if he’s good, writes for an audience. That might be an audience of one or one million, but you have an audience with certain interests and backgrounds in mind. With new visitors came a new audience, and I began to feel them out, based on their comments and
emails, and to start the process of discovering what they were interested in, and to write with them in mind. Writing is a conversation, and as new people came into the conversation, my writing changed. I’m still going through that process, and probably always will be.

What specifically did I do differently? I think I began exploring the form of writing on blogs that’s a cross between a feature magazine article and a memoir. That is to say, they are often how-to articles that address a particular reader problem, written in a more conversational style. I’m still experimenting with that form now.

How did your readers find out about you?

Well, in the beginning I had to tell them I was there, otherwise no one would have found me. I posted a link or two on other blogs, just letting them know about a related article I’d written. I also posted on some forums now and then. Those links would bring in perhaps a dozen readers. But those readers would stay, and some of them would post a link on their blogs. From there, things grew, a little slowly at first, but they snowballed. Bloggers link to me, and other bloggers
read those blogs and then link to me, and so on.

There are a jillion blogs out there, and a bunch of them focusing on self-improvement. What about your blog stood out from the rest and led to the following you’ve built?

That’s something I’m trying to figure out myself. Based on what my readers have told me, it seems that I offer very practical, rubber-meets-the-road advice, as compared to more generalized advice you might find on some blogs. I’ve also been praised for my style, which people say is humble and down-to-earth. It’s hard for me to judge whether that’s true or not, but I’ve heard it enough times from readers that I can’t discount it anymore.

But just as importantly, I think I’ve tapped into something that many other people haven’t. Specifically, I focus on simplicity in a world where others focus on doing more. They are worried about getting things done with new technology, while I’m more concerned with scaling back in the face of the chaos of our technological world. I don’t eschew technology, but instead advise that we don’t have to do everything, just because we can. There is more information available than ever before, but we don’t need it all. We get thousands of emails, but don’t need to respond to all of them. That has turned out to be a powerful message that appeals to a lot of people like me.

How much do you think using the word “Zen” in the blog’s name and its visual design (with its soothing white space and gentle gray font) has played in the blog’s appeal?

The word “Zen” and the uncluttered look of the blog tie in directly to the message of simplicity that runs throughout my blog. The name, design, and content are in unity, and I think that’s incredibly
important. It’s easy to talk about simplicity, but it’s harder to actually do it. The simplicity of my message that’s implied in the name Zen Habits has hooked into a consciousness that rarely has an outlet in our online society. I think that’s helped my appeal tremendously.

How is the blog doing financially?

I make more money blogging than I do at my day job these days. In fact, I’m quitting my day job.

You’ve said on your blog that you’re conservative in the number of ads you accept. How has the blog been able to meet your financial needs, if you aren’t taking as many ads as you could?
You have to think about the reader first. When I go to another blog and there are a lot of ads on it, it turns me off, and I don’t come back. My fear is that I’m going to overwhelm the reader with too many ads, so I’ve tried throughout the year to limit how many ads I have on there, to keep it relatively clutter free, and to use the ad networks that really work.

Having a bunch of ads does not guarantee revenue. What really brings revenue is traffic. So what you really have to focus on is attracting readers — ads don’t attract readers, great content does. First, build up a destination. The readers will come, and if the readers come, the revenue will come — not the other way around.

“The reader is the new editor.”

In addition to your day job, you’re also a freelance writer. Historically, freelance writers have been at the mercy of the traditional media establishment. Newspaper, magazines, and books — run by editors and publishers — were the only ways a writer could get their work out, and make a living. But blogging is changing that. With blogging, a writer can get their work out and generate income all on their own. How is this changing the equation for writers, or changing the balance of power between editors/publishers and writers?

Going from freelance writing to blogging is incredibly, incredibly liberating. I’ve always been at the mercy of an editor. I can propose topics for articles, but in the end it’s their call. I can write articles with unique angles, but in the end, if they don’t like it, it doesn’t fly. I can put in my personal opinions and anecdotes, but more often than not they will be cut out. So my creativity is
stifled by the traditional freelancer-editor model.

As a blogger, I can write about whatever I want, whenever I want, however I want. The pressure of deadlines, of meeting someone else’s expectations, of being limited to a certain kind of writing, it’s all gone. The need for an editor is gone.

I’ve been an editor. I know the value of an editor for a newspaper or magazine. But for a blog, it’s completely unnecessary. In the end, the reader is the new editor. The reader will decide what he likes to read, and if a writer isn’t good, the reader will go elsewhere. The reader’s choices are the ultimate edits.

You made a somewhat controversial decision recently to make all the content on your blog copyright-free. Anyone can use it any way they like, though you’ve asked folks to credit you if they do use it. Why did you decide to give up your copyright?
It highlights the changes that are happening in the publishing world. It’s definitely a change in the mindset of traditional publishing. Copyright was necessary when publishing and distribution was limited and expensive. But nowadays distribution is unlimited and publishing is extremely inexpensive.

I see the new business model being completely different. Now, the more people who know your name and know your brand, the better. From a business standpoint, if someone wants to share my content with friends, and they share it with more friends, you might say you’ve lost revenue … but from my point of view, I haven’t lost revenue because I never would have gotten that revenue anyway. But this way I’ve gained more readers, and the model of the future is to gain as many readers as possible.

What’s in store for you in the year ahead?
First is just to continue to improve Zen Habits. That has become my greatest joy in life.

The second thing is my book [The Power of Less, to be published by Don’t Sweat the Small Stuff publisher Hyperion]. That is going to be a major accomplishment in my life, one of the biggest things that has ever happened to me. I want to do a great job with it.

I’m starting a second blog, called Write to Done. It’s a blog for writers. I’m going to cover everything from writing your first novel and selling a book to writing great blog posts and the business side of freelancing. I’m not really doing it to make money but to write about stuff that I’m interested in writing about. If it eventually makes money great, but if not, it’s a great outlet for me to write about things I want to write about.
And I’m starting an online business with a partner, Glen Stansberry of the LifeDev.net blog. We’ll be selling a series of short ebooks, guides to doing different things on the Internet. It’s a way for me to share some of the things I’ve been learning online. The online market is really growing. People are just starting to get into writing blogs, even to get into reading blogs. The audience for these kinds of things is going to be greatly expanding in the next few years.

So you get to the end of 2007, and there are at least 30,000 people out there who think you’re a rock star. How about your wife? Does she think you’re a rock star? Or just the same old guy who can’t manage to get his dirty socks in the hamper?
[Laughs] She definitely thinks I’m a rock star. She’s been so supportive and so excited about my success — more than anyone else, with the possible exception of my mom. Every time something great happens, I call her up or instant message her to share it.

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Tips for creating a blog with mass appeal
1. Be useful
“Figure out what problems people face in their lives, and write incredibly useful articles that help them solve those problems. The more useful info, the better.”
2. Write great headlines
“Headlines are the most important words the blogger writes. They are the only thing people see when they read your blog in an RSS feed reader. They see a bunch of headlines and decide whether they’re going to read more based on your headline. I use magazine covers as a model — whether Cosmopolitan or Men’s Health — they have a bunch of cover lines that are designed to draw readers in.”
3. Sell yourself
“Promote your brand by networking, by writing great guest posts for other blogs, and through social media such as Digg and del.icio.us.”
4. Integrity builds loyalty
“Always, always, always remember that the readers must come first and must be central in everything you do. If you have things on your blog that are about your blog’s promotion, or about promoting anything else, and are not there for the reader’s benefit, remove them.”

In five short years, entertainment reporter Jane Boursaw has gone from doing the typical freelancer thing — picking up gigs catch as catch can — to creating a series of syndicated columns that now run in more than 300 publications and Web sites nationwide. Boursaw, the author behind Reel Life with Jane, focuses on family films and TV shows, and her syndicated TV and movie reviews appear in regional and parenting publications nationwide. She’s also kept up a vibrant freelancing career, often penning profiles of child celebrities, including, most recently, a profile of Heroes actress Hayden Panettiere that appeared in American Eagle’s Latitudes magazine. The kicker? Boursaw is no typical Tinsel Town scribe. Instead, she does it all from her home near Traverse City, Michigan.

mediabistro.com caught up with Boursaw to ask her how she landed her syndication gigs and how she stays on top of the latest Hollywood shenanigans from 2,000 miles away.

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How did you get the idea to start covering Hollywood from Michigan?
I’ve always loved movies, TV and celebrities, and I had one of those “If I could do anything, what would it be?” moments. What I’m doing now is what I envisioned when I posed that question many years ago.

How did you get the idea to create a syndicated column?
I saw a need for a good family movie column for the many regional family publications in existence. I love family movies and enjoy seeing them with my own kids, so it seemed like a natural path for me.

How did you get started?
My first column was on MommaSaid.net, owned by Jen Singer (author of 14 Hours ‘Til Bedtime). Jen has been my loyal supporter from the beginning, and she was more than happy to launch my column on her wonderful parenting site.

Any false starts in getting this underway?
Not really. I think you just have to be patient and not expect that it will happen all at once. It takes a long time to establish yourself and build a presence in any given niche. I’ve never had a time when I had 50 new markets come in all at once. It’s more like two here, three there — the goal is to keep marketing all the time and building slow and steady.

Always market yourself — try and do some sort of marketing every day. Keep building a good Web presence and keep networking in a lot of different areas.

When did you start feeling like you had momentum?
Probably a couple of years ago. I hired a professional Web designer to redo my Web site, and that helped to solidify my brand, Reel Life With Jane, on the Web.

What’s the key to being a successful syndicator?

Always market yourself — try and do some sort of marketing every day. Keep building a good Web presence and keep networking in a lot of different areas. Aside from the syndicated column, I write for a variety of markets, providing TV, movie and celebrity content. All my articles and bios include a tagline with info on the syndicated column. So even if it’s a celebrity profile in Latitudes, an editor for a regional family publication might see my tagline and contact me about the syndicated column.

Which of your columns is the most successful?
The weekly family movie review — an in-depth review of a new family movie each week. Most regional family pubs have an online presence, and many use this review for their Web site. I think there was a need for an affordable, down-to-earth column that would tell parents which movies are OK — and not OK — for their kids. Parents can’t see every movie before their kids do. I have a responsibility to offer parents good info that they can trust. The MPAA ratings system isn’t always black and white, so there may be some PG-rated movies that aren’t appropriate for kids. That’s why my reviews include detailed content on profanity, violence, and sexual innuendo. It’s amazing how many PG-rated animated movies contain all of these elements.

What are editors looking for from a syndicator?
Someone who’s reliable, delivers clean copy on time all the time, and isn’t priced out of the ballpark. Most regional family publications don’t have a huge budget, and I’m happy to work within their budgets. I concentrate on building a good client base, so that I’m not dependent on a few markets to keep me solvent.

What’s hard about covering Hollywood from 2,000 miles away?
My particular niche doesn’t require me to live in LA or NYC. I’m well-connected within the industry, so I generally get intel regarding movies, TV shows and many celebrities before it reaches the general public anyway.

Do you ever get any pushback by folks in Hollywood, because you’re not on their home turf?
Never.

What’s the key to staying in the loop?
Being connected doesn’t necessarily mean living in LA or NYC. It means building good contacts with publicists, TV networks, and movie production and distribution companies. I’ve spent years doing that and feel like I have a pretty good handle on the inside track. Also try to diversify yourself as much as possible. During the past few years, I’ve focused on having a variety of clients. Good markets end all the time, for reasons beyond our control. You don’t ever want to be in a position of having all your eggs in one or two baskets.

You covered Spinal Tap actor Michael McKean from Michigan for a Southern California magazine. How come the editor didn’t just go with a local writer?
Editors are looking for good writers who deliver clean copy on time. I’m a phone call away from any celebrity, so I don’t think you necessarily have to meet with profile subjects face to face. Other than my Web site, I’m listed in a variety of places, including Freelance Success, ASJA, mediabistro.com, JournalismJobs, and others. All of my listings give editors a good idea of the types of work I do, and I still query editors with ideas, as well. I also belong to several online writers’ groups. Those give you a built-in networking community.

How do clients find you?
Many clients come to me through referrals from current clients or via my Web site. My Web designer has done a fabulous job of placing me high in the search engines, using keywords for my niche. But I’m always marketing, scanning job boards for new clients and possible gigs, and all my writing buddies send me job opportunities that seem like a good fit for me.

In addition to the three columns and assorted freelance assignments, you also contribute to five blogs (including your own Reel Life With Jane, Ruby Shoes, and Film Gecko). How do you find the time?

I’m really geeky when it comes to using lots of different tools to streamline my work, but it’s a necessity to keep track of everything. For overall planning, I use both a hard-copy calendar on my desk, as well as Franklin Covey’s PlanPlus on my computer. I use Google Reader to collect news items and intel from at least 300 sources every day. That keeps me up-to-date on the inside scoop from pubs like The Hollywood Reporter, Variety, IMDB.com and a variety of RSS feeds.

I use an offline editor (Windows Live Writer) for composing blog items, which streamlines the blogging process tremendously. That program allows you to easily compose blogs, add photos, videos, Amazon links, hyperlinks, tags and other necessities. Right now, I have five blogs on Windows Live Writer, each in their own file.

I use multiple spreadsheets to keep track of what’s been blogged where and how many blog posts I’ve done on any given day. More specifically, for FilmGecko.com, I have a spreadsheet with upcoming movies for the year, and each movie has a column for trailers, news items, interviews, casting news, previews, reviews, contests, etc. That way, I can know at a glance what I’ve covered for a given movie and what still needs to be covered.

Best Hollywood reporting moment?
I think a lot of people feel like celebrities live in another world from the rest of us. But all the celebs I’ve interviewed are just regular people with families, schoolwork, and jobs they go to every day. Because we see them in the press all the time, I think there’s a tendency to feel like they’re somehow different. But I haven’t found that to be the case. Most are friendly and down-to-earth and just trying to get by like the rest of us.

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Tips for starting a syndicated column:
1. Offer options: I offer two versions of the syndicated column. The monthly version includes short synopses of upcoming family movies. The weekly column is a detailed review of a new family movie released each week. If there are no new theater releases, I’ll do a DVD review. I find that most editors like the monthly column for their print pub and the weekly for their Web site.
2. Market continually: I market all the time, usually every day, in one form or another. I send emails, scan writing job boards for family pubs, and work from a couple of reliable contact lists.
3. Work within their budgets: The rates for my syndicated family movie column vary from $5/mo. for really small pubs to $100/mo. for larger pubs. I’m OK with that. I’m here to serve them, not the other way around.
4. Offer them something they can’t find elsewhere: In my case, I have a particular voice to my writing that’s chatty and conversational. Again, I’m here to serve the clients and offer their readers something interesting they won’t find anywhere else: Me.

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E.B. Boyd is a freelance writer based in San Francisco.

Back in 2002, Jessa Crispin’s job as a fundraiser for Planned Parenthood kept her occupied for all of one hour a day. Needing something to fill the other seven, Crispin started blogging about books. In 2003, her site, Bookslut had grown into a Web zine with a handful of writers, and Time named it one of the 50 best Web sites of the year. How they found her, Jessa doesn’t know. She wasn’t actively seeking stardom. Eventually, however, she did become a full-time writer — out of necessity. When she moved from Austin to Chicago and started job-hunting among nonprofits, prospective employers threw her name into Google to check her out. The name “Jessa Crispin” being somewhat distinctive, they inevitably stumbled across Bookslut — and the explanation of how it got started — and suggested that perhaps her passion lay elsewhere.

Today Bookslut is one of the leading literary Web zines, with about 9,000 unique visitors a day. Thirty to 40 writers contribute to the daily blog and write features, Q&As, and reviews for the monthly magazine. At a time when newspaper book review sections are folding and traditional book reviewers are grousing about the quality of criticism on the Web, Publishers Weekly declared that Crispin is “rewriting the rules of reviewing” and called Bookslut “one of the most provocative and erudite” of online book sites.

In addition to Bookslut, Crispin freelances for NPR.com’s Books We Like and for The Smart Set, the online reincarnation of the early 20th-century literary magazine that once featured the writings of Dorothy Parker, F. Scott Fitzgerald, and Theodore Dreiser. mediabistro.com caught up with Crispin to find out how she turned her literary musings into a leading Web zine.

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Bookslut started out as a place to record your own thoughts, but today it’s fairly prominent. When did you realize it was having influence and resonance beyond just your friends?
It took three months for me just to check the stats to see if other people were reading it. It was sort of a surprise when I did and there were. There were also two major milestones. One was when Time called us one of the 50 best Web sites [in 2003]. And then, about six months before that, Neil Gaiman [of The Sandman comic book fame] linked to us and brought us a huge audience. I had not told Neil we existed, so it seemed surprising that someone found us on their own, especially someone like him. But I also realized [it had traction] when I no longer had to search for new reviewers and new writers, when they started coming to me and wanting to write for me.

How far into it did that start to happen?
About a year into it.

You’ve said you prefer the multiple-voice approach of a Web zine to the single-voice approach of a one-person blog. Why is that?
It’s helped me just so that I don’t get bored. Sitting there talking to yourself day after day, you get tired of yourself. It helps to invite some other people to join in the conversation. But also, I think it helps the audience, so they don’t get totally bored with you. One person may hate me but love Sticky Pages, which is our Tuesday blogging section. It just broadens your appeal.

You’ve watched other literary sites come and go over the past six years. Why have some succeeded and others failed?
The ones that have stayed around have very unique voices, and they’re updated on a very regular basis. The ones that have fallen away the most seem to be the ones where the writer was like, “Oh, I can do this too, but I’m not going to put that much effort into it.” It’s hard to get an audience if they don’t know when to check for updates.

Also in the last two to three years, there have been an overwhelming number of blogs about literature, so I can’t imagine how somebody outside of The New York Times, which just launched their books blog, or The New Yorker, which also launched a books blog, would be able to find an audience without some sort of already established site or established audience. I can’t imagine it would be easy to get anybody’s attention.

Why have you decided not to make Bookslut your full-time job?
We realized that trying to be supported completely by publishers’ ads wasn’t going to do it because they don’t advertise that much, especially online. So the idea of opening the site up for conventional advertising — the liquor ads and that sort of thing — that whole system is dependent on page views. It’s the Gawker way of running things. I realized Bookslut would probably have to turn into something [that] encouraged page views and would become something that I wasn’t proud of anymore.

You’ve said that, since the bankruptcy of the parent company of book distributor Publishers Group West, online ad sales from publishers have plummeted, so now you’re paying writers in books. Why do you think so many people, good writers, are willing to write without pay?
Part of is that we don’t put a lot of restrictions on what they’re able to write about. I don’t mind if they wander in territory that they didn’t initially sign up for. They appreciate that. And there are a lot of people out there who really enjoy writing about literature and the authors that they like. I guess I should have figured that out since I was doing it myself. It was sort of surprising when I found out there were others who wanted to do it, too.

Also, the other day I was talking to one of my feature writers, who writes books. She does criticism, and she said all publishers expect you to have an established platform when you come to them with a book. She said there’s no better way to build that platform than to do a consistent column or feature online, so people know where to find you.

Does she have to have to show traffic stats to the publishers to prove she has an audience?
She’s never asked me for stats. I think the name Bookslut carries enough weight these days that that’s all people really need to know.

Did that change your thinking about what you’re doing?
These things sort of momentarily freak me out, and then I try to forget that I know them.

“I’m pleased as punch that the idea of the authority is going away. The New York Times never spoke to me. If you were one of those people who don’t agree that Philip Roth is the greatest American living writer, where were you supposed to go to find new books?”

You’ve mentioned that you don’t follow your traffic all that closely. You don’t break down what your audience is reading, for example.
I’m afraid that will influence what I do on Bookslut. Once you start chasing the reader, that’s when the reader loses interest. There’s all this talk about what can we do to capture the attention of a particular demographic, but I think having a conversation is probably the least productive thing you could be doing. I like what we’re doing on Bookslut. Our audience likes what we’re doing on Bookslut. So I just sort of leave it at that.

If the stats started spiraling downward, then I would probably pay attention to see what’s going on. But as it is, we’re seeing consistent growth, so I try not to obsess over “Why do poetry reviews not get as many page views as the fiction reviews?” or “Why does this column not get so many hits?” I like what we’re doing, so I figure that’s enough. It’s a dictatorship; it’s fine.

A benevolent one.
Yes, I’m a very benevolent dictator.

What reactions do you get from authors you ask for interviews? Do they get what Bookslut is about and understand what you’re doing? Or do they think you’re coming out of left field and don’t understand how it fits into conventional book promotion?
Most authors like us unless we give them reason not to. Most writers like the enthusiasm, and they like that there’s a new, more approachable avenue that’s not The New York Times. Obviously we don’t get the traffic that The New York Times gets. It doesn’t give them the hit that that would. But at least we’re enthusiastic, and we’re paying attention.

What are your favorite sites to go to learn about new books?
I really like the Guardian books section a lot. As far as other blogs, I like Journalista [the blog of The Comics Journal] and Maud Newton — and I read Jezebel way too much.

What do you like about Journalista and Maud Newton?
I like Maud because she’s very thoughtful. She much more thoughtful than a lot of other bloggers, and she doesn’t have an ax to grind with anyone. I like that she keeps her distance from any sort of literary scene.

And Journalista is just… A lot of comic book Web sites are overrun with geeky nastiness, sexism, and weird obsessive-compulsive behavior. Journalista is not like that. It has a very good sense of humor.

What’s wrong with being a part of the literary scene?
I noticed that, when the literary blogs first started to be accepted as a credible thing, a log of bloggers would brag about what parties they got invited to, and there were pictures of them at the parties. And then those writers would get glowing notices in the blog. It seemed they were spending a lot of energy trying to get into the cocktail party scene. They were willing to trade their legitimacy for a party invite.

Many traditional book reviewers look still askance at online literary sites. In fact, The News Hour just had a debate on this very thing, after the Los Angeles Times jettisoned its standalone book section. Why the animosity?
Part of it is the disappearing newspaper book sections. It’s so hard to make a living as a book critic. The newspapers don’t pay very much for reviews. But people who had worked out a system saw the rise of Internet criticism, not even criticism, but just the blogs, at the same time as they saw newspaper book sections declining. I think they thought the blogs were the cause of the demise. But they weren’t. No blogger has ever said that their goal was to destroy the newspaper book section, or even that they thought they could replace it. But I think there was a lot of animosity because the reviewers’ livelihoods were disappearing, and they thought us young whippersnappers were invading their territory.

What do you think the world of book reviewing is going to be like 10 years down the road? What’s going to change? What are we going to gain? What are we going to lose?
There’s going to be a lot more original content online from both “legitimate” sources and so-called “non-legitimate” sources, the “legitimate” sources being The New York Times or The New Yorker or the like. A lot of lit mags will move online because a lot of them are hurting trying to meet printer costs.

With the demise of newspaper book review sections and the explosion of book Web sites, how are readers supposed to figure out where the voice of authority is? In the past, all you had to do was open your newspaper’s book review section, and there was your bible.
I’m pleased as punch that the idea of the authority is going away. The New York Times never spoke to me. If you were one of those people who don’t agree that Philip Roth is the greatest American living writer, where were you supposed to go to find new books? I think it’s great that that filter is changing.

As far as finding your authority, you just have to read a lot and find the person that you like or the book review section that you like. I get more accurate book recommendations from the London Review of Books than I’ve gotten anywhere else, and it’s taken me years to find that thing. I understand the exasperation, especially when so many books are published, hundreds of thousands of books are published in a year. It’s difficult for the publishers, for the writers, and for the audience, because nobody knows who to turn to. But I think the longer that we get used to this, the easier it will become. The blogs or publications that survive will survive for a reason, because of their quality and because of their dedicated audiences. I think things just haven’t evened out yet.

Are there any unexpected side benefits to being the founder of a fairly well-known Web zine?
It certainly opens freelance doors. I don’t have to make blind pitches. I can say, “Hi, I’m the editor of Bookslut,” and people already know where I’m coming from. That recognition has helped considerably. But also the books delivered to my doorstep are very nice.

Fill in the blank: If the Internet hadn’t come along and I wasn’t doing this, I would probably be working in/at ______.
A nonprofit. That’s what I was doing when I started Bookslut, and Bookslut turned into either a distraction or a course correction. I sort of wandered between the two. But I really loved working at Planned Parenthood.

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Tips for starting your own literary Web zine

1. Find a niche. The literary zine market is saturated. To stand out, you’re going to have to focus on something in particular — like young adult novels or science fiction — where you have a chance of getting noticed.
2. Stay regular. “Regularity in posting is so important,” Crispin says. Audiences get created when readers make regular visits to your site. They’ll make those visits if they know when the new stuff is going up.
3. Trust your intuition. Crispin says she regularly gets unsolicited advice from all corners, including established figures in the literary world. So far, however, she’s followed her inner compass. After all, the Web is still uncharted territory. Nobody has the secret to what will make it work, including those operating from maps drafted in the offline world.
4. Find soul mates. Join forces with other writers whose aesthetic you share and trust. Multiple voices increase the chance a visitor will find something they enjoy, and common aesthetics ensure that the zine develops a distinct identity.
5. Don’t pander. Resist the urge to try to figure out what readers want and to give them that. It’s a really good way to chase them away. After all, readers are coming to your party. They want to see what you’ve got going on.

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E.B. Boyd is a San Francisco-based freelance writer. She blogs about the future of the news business at future-of-news.blogspot.com.