Traditional media outlets are floundering because more and more readers are getting their news from the Web. This is not news. But what is news is how Web outlets are drawing readers and advertisers and making money.

BuzzMedia is one of the largest independent publishers of online content — and it’s one to watch. Its portfolio is a mix of music and celeb news sites, like Just Jared, Celebuzz, Idolator and Stereogum, and the personal websites of celebrities like Kim Kardashian and Britney Spears. BuzzMedia’s model of blending celeb-created content with original and breaking celebrity and music news has been so successful, the company was able to recently acquire three music blogs and form partnerships with three more to expand its portfolio and reach.

This newly expanded music portfolio, which currently reaches 6.7 million users a month, is headed by editor-in-chief Jeff Leeds. A former New York Times music reporter, he says he made the leap from print to the Web because he saw the writing on the wall early. But is his snark-loving band of misfits tapping the final nail into the coffin of arts and culture journalism? Not so fast.

Name: Jeff Leeds
Position: Editor-in-chief, BuzzMedia Music
Resume: Started his career as a reporter for the Los Angeles Times, where he worked for nine years, covering a variety of beats from white-collar crime to politics. Covered the music industry from the business desk at the LAT for two years before moving to the New York Times‘ L.A. bureau, when he covered music and the business of the music industry. Left NYT in 2008 and joined BuzzMedia.
Birthdate: December 15
Hometown: Fairfax, Virginia
Education: Bachelor’s degree in American government from University of Virginia
Marital status: Married
First section of the Sunday New York Times: “I never miss the wedding section.”
Favorite TV show: 24
Guilty pleasure: Batman comics, Millionaire Matchmaker on Bravo.
Last book read: Iron Fists, by Steven Heller
Twitter: @jeffleeds

How did you make the move from a traditional journalist into the position of editor-in-chief of this group of music blogs?

I left The New York Times in mid-08 as a result of the company reorganization of the editorial staff. At the time, I really felt like there would be some interesting opportunities in the digital music space. BuzzMedia was one of a couple of companies that I thought had figured out or was in the process of figuring out how to create really compelling programming for the most passionate, engaged music fans. I knew the company a bit just from reporting on the music industry. I just wanted to be close to an experience that was social and offered the chance to create something new.

What does your job entail?

In my job here, I help create editorial features, secure exclusive content like song or video premieres, monitor the performance of specific programming and our sites overall, develop new site concepts and designs, advise our sales and marketing teams on campaigns, and scout and analyze new site acquisitions. It’s sort of the “fixer” role — if the company needs to figure something out in music, I try to help. Our portfolio includes really leading sites in different genres and fields of music: Stereogum.com, Buzznet.com, AbsolutePunk.net, and Idolator.com.

Do you interact with any of the other BuzzMedia sites that aren’t music sites, like Videogum, The Superficial or Just Jared?

As a whole, we do try to operate together when possible. Sometimes there is overlap that can work in places like pop music where Celebuzz, which is our big celebrity entertainment hub, can work with Idolator, which is our pop music site. There’s always been a lot of overlap there. So, where possible, those sites create content together, link back and forth and hopefully deliver more readers to both sites.

BuzzMedia also owns the official blogs of celebs like Kim Kardashian. How does the company internally differentiate between sites like Idolator and KimKardashian.com?

Our talent sites are really run separately. Each of those celebrities has their own site and has someone here who is here to help them produce it. But they don’t really work directly with us, and certainly not with the music sites.

How has the transition from print to the Web been for you?

I think it’s been refreshing. There’s so much that the print world is only beginning to learn about how to operate on the Web. Before I came here, I was really fascinated with the Web, and I think it was clear to everybody that writers and editors in traditional media needed to find ways not just to produce content using the Web, but then actually using the Web to distribute that content. At the Times, we had a weekly music podcast, and I was really trying to think of interesting segments and content for that. And around 2007, I was also really interested in creating content exclusively for the Web. It was increasingly clear that so many readers consume content basically on the Web. One endeavor was before the SXSW music festival. We planned out a series of stories that we decided to tell via special Web-only videos, mini TV segments essentially. So I worked with a producer and went to Austin and shot a series of segments.

Do you still get to write?

I do [write] a bit. I do a fair bit of line editing and a little bit of writing, a little bit of production of other kinds of content including photo and video content. But I try to prioritize the strategic needs of the sites.

Do you miss writing long-form pieces?

Sometimes. I think that I don’t really see a clear avenue for me to write that kind of piece at the moment, but sooner or later it might be fun to try that again. I think that obviously the open question for everyone is: Where are people reading that kind of content in large numbers?

Do you think that the 2,000-word celebrity profile or 500-word music review is obsolete?

I don’t. I think whether you call it a review or not, there’s a great deal of intelligent discussion going on around music and around new releases, in and out of our portfolio. I do worry sometimes about the overall health of traditional music criticism. But at the same time, I’m incredibly excited by the passion and creativity that I see on all of our sites, up to and including content created by users.

It seems like more and more artists and celebrities break news themselves through Twitter and Facebook. How has covering breaking news changed since you were doing it at the Times?

In terms of competing on news itself, I think breaking news is still vital and I think truly great stories will always command eyeballs. But it does feel like the pace of the news cycle just doesn’t allow for stories to have the ripple effect, or to create weeks of discussion the way it once did. I actually see one example of that, and a response to it, in music, in that artists and record labels are slicing their songs and videos more and more finely in order to try to pique interest several times, instead of just once. You may notice — at least in certain genres — the artist or label will first release a series of images from a new music video, then maybe a snippet of it, then a behind-the-scenes clip, then a related playlist, then maybe the video itself. The reason it works sometimes, of course, is that the audience’s appetite for information remains gargantuan.

What advice would you give someone who wants to get into music writing and reporting?

It almost goes without saying, but I’ll say anyway, that anyone who wants to be a writer simply needs to write as much as possible. Pursue internships, freelance, start a blog and treat it seriously, all of that. I also think it’s essential for writers to find a way to get really comfortable communicating directly with readers, to hearing instant feedback, to arguing their own cases, if you will.

I think it’s also a good idea to be active in an online community someplace, and to really try to build an identity there. In music, I’ve seen some strong young writers emerge from the readers of sites like Absolute Punk and Buzznet, two of our sites. I think the writer’s life is always going to be a little lonely, but I think that participating actively in these kinds of distinct communities can provide great inspiration and remind you that you actually are part of a wider world.

Amanda Ernst is deputy editor at Crushable.

Gossip Girl, the popular teen soap, has opened up the fashion world of Upper East Side Manhattan to young women across the country, much like Sex and the City did for a slightly older generation of women. So it’s not surprising, then, that the man responsible for Gossip Girl‘s fashionable clothing choices, costume designer Eric Daman, honed his skills styling for Carrie and company as Patricia Field’s assistant.

Daman, who has no formal fashion training, sort of fell into the biz. After studying at the Sorbonne and working in a Paris boutique, he held stints as a model and editorial stylist in New York before landing his first costume design project on an independent film. Later, an acquaintance from his Paris days offered him the ultimate gig. “I ran into Patricia Field. She was just getting ready to start up the second season of Sex and the City, and they were looking for a new assistant to come on who had an editorial background but also understood costume design. I ended up doing seasons two, three, and four and winning an Emmy.”

Now, with the book You Know You Want It in stores and a line of party dresses for Charlotte Russe debuting next month, Daman is happy to be known as a trendsetter in teen fashion — even if the honor comes with a little responsibility.

“I don’t want all the girls who watch [Gossip Girl] in the Midwest to feel bad because they’re watching something that they don’t think they can ever be a part of,” he said. “What we want to do is to show people that you don’t have to be a millionaire to look like a million bucks.”

Name: Eric Daman
Position: Costume designer, Gossip Girl
Hometown: Monroe, Michigan
Education: Sorbonne, where he studied French literature
Resume: After school, worked in Paris boutique Magic Circle, where he also did PR and marketing. Moved to New York to model in the early ’90s, then launched stylist career by working in editorial for small publications like ID, The Face and Visionaire. Started as a costume designer on 1998’s The Adventures of Sebastian Cole, then worked on Sex and the City, The Door in the Floor and Gossip Girl.
Marital status: Not married
Favorite TV show: Gossip Girl
Guilty pleasure: “Enjoying watching the show I actually work on. It is true. I’m a big fan and it’s funny because I love teen girl movies, and I was read the books, and it’s a pleasure to watch it and enjoy it as much as it is to work on it.”
Last book read: American Psycho by Bret Easton Ellis

As a costume designer for a TV show, what do you do day to day?
I was on set this morning. Whenever there’s a scene, I know when all the extras will be there. My assistant usually oversees all the extras, but sometimes I’ll go for an extra big party scene and help dress the extras in the morning. Now I’m on my way to an appointment at Louis Vuitton to pull clothes for [characters] Serena and Blair. So it’s a mix of shopping and reading scripts and production meetings and dressing people and running around the city to pull clothes. And in between that, last year I wrote a book, and in between that I have side projects, as well. Right now I’m working on a line of party dresses coming out for Charlotte Russe, and right now we’re shooting the campaign for that. So I leave set and shoot that and then come back and go to a production meeting. I definitely stay busy during the day.

When you pick clothes for the show, how is your approach different from editorial? Do you have to think about lighting, camera angles, and things like that?
You have to think about everything. The first thing you think about is what looks best on the girls themselves. And then… each script dictates what has to be going on, either a school day, or a date, or a ball. There’s a lot of different things that you really have to take into consideration. And then also, for me it’s really important to take into consideration the emotion that’s going to be going on in the scene, as well. You don’t want the outfit to overpower the emotion that the actress needs to show. You want to embody and support that. You have to think what [the costume] needs to inspire the actress to do in the scene. And it also has to look amazing and fashionable.

I’ve always wondered — does the school have a dress code?
They are always in a version of the uniform. Definitely the Gossip Girl version of the uniform. We definitely took liberties with it. But Blair was always in her navy skirt — they were always in navy skirts and white blouses and some sort of tie. Sometimes the skirts were shorter, sometimes the skirts were short, but we definitely took liberties with it. We basically took the idea of what a Catholic school uniform was and then slowly transcended that into the Gossip Girl universe.

Do you think that some of the actors who you’re working with on Gossip Girl have taken on the fashion personalities of their characters?
They’ve gotten some really good fashion lessons from what they’ve learned on the show. When I first met Blake Lively, she wasn’t having lunch with Karl Lagerfeld… I’m like a fashion professor, and I’ve taught them all about these labels and how to wear clothes and they really appreciate it. To see them go out on their own and become these fashion icons is really great. I’m proud of them. To see Leighton [Meester] in Lanvin going down the red carpet and Blake on the cover of Vogue is really thrilling… Blake is a little more symbiotic with who Serena is, where Leighton is very different from the way Blair is on TV.

Fashion on reality TV, and on shows like yours, has become a huge industry on TV. What do you think the media has gotten right about the fashion world?
I think fashion is so much more available and people are really getting into it, especially the younger demographic that is watching all these shows and is part of the marketing and branding of it and is so savvy about seeing things on the Internet… And I think a lot of these young girls really capitalize on the idea, texting and that whole thing… but also in terms of the branding and the marketing. If you go online, you can see what Blair was wearing that night and where to buy it. On Project Runway, they all have these social networking devices that really lend themselves to the fashion marketing. There’s really brilliant marketing and branding behind all these shows. I think it just hits the mark. I think it really just launched a fuse on fashion intelligence, and people really have a hungry desire.

What traits to you think a costume designer needs to have in order to be successful?
A good nature and an open mind. Because a lot of designers out there get really stuck on the fact that ‘This is my vision, this is what I want the clothes to be,’ and I think it’s really important to have a relationship with the actresses and with the clothing so it’s not just stuck on this one thing.

What are your Fashion Week plans?
I don’t know. I’m definitely working on Gossip Girl. I’ve been invited to a few shows, but usually I can’t make it to the shows because they’re during my work day. We just review them on Style.com. But there are a couple of shows that I’m going to go see. And I’ve been invited to participate in a couple of Fashion Night Out events. Last year I did an event at Henri Bendel based around my book and teaching girls how to accessorize. That was a lot of fun.

What advice would you give someone who wants to get into costume design?
I feel like life is a bunch of paths that cross and you have to take chances. You have to put yourself out there and take risks, and you just have to believe in yourself and have determination. It’s not necessarily about school… A lot of it is being in the right place at the right time and knowing when to take that jump. If I had never met Steven Meisel, I never would have moved to New York. And moving after seven years of life in Paris was a big choice, but it was right. I think a lot of people tend to get scared and not take chances. I think life is all about chances, and if it doesn’t work out, then it doesn’t work out.

NEXT >> So You Wanna Work in Fashion PR?

Who’s Amanda Ernst? That’s a secret I’ll never tell. XOXO, Gossip Girl.

There’s something very attractive about career reinvention, especially in this anemic job market. But how to start?

Pamela Mitchell, career coach, author, and founder and CEO of The Reinvention Institute, is uniquely able to walk clients through that transition — because it’s something she’s experienced twice herself. And, when she went through it, there weren’t any companies like hers around to help.

“What I found was that most career coaches, career services and books were built upon the assumption that you wanted to climb the ladder in your career,” she said. “There was nothing that talked about what happens when you want to switch industries and how to make that happen. So I had to figure it out by myself, the hard way.”

Drawing on that knowledge and a desire to help others, Mitchell launched The Reinvention Institute. Her company, which employs career coaches who have worked in corporate America themselves, focuses on providing clients with the tools to break into an entirely different field, basically rounding out their skill set in a different way. And for media professionals, Mitchell says the next frontier for career success may just lie in… gaming?

Name: Pamela Mitchell
Position: Founder and CEO of The Reinvention Institute. Author of 10 Laws of Career Reinvention: Essential Survival Skills for Any Economy (Dutton)
Resume: First handled international partnerships for Wall Street information provider Knight Ridder, but went through first career transition to move into the entertainment industry. Worked for Discovery Channel and Playboy.com before leaving to launch The Reinvention Institute.
Birthdate: July 22
Hometown: Milwaukee, Wisconsin
Education: Undergraduate degree from Harvard College, master’s degree from Thunderbird School of International Management.
Marital status: Married
First section of the Sunday Times: “Styles.”
Favorite TV show: “I watch a lot of home and garden television, any design show. I’m not a big TV watcher, but on Saturday nights and weekends when I want to relax, I turn on HGTV and see what kind of home design shows are on.”
Guilty pleasure: Bridezillas
Last book read: Influencer: The Power To Change Anything
Twitter handle: @reinvent

Having gone through career reinvention yourself, what is it like for you to see people going through a transition?

For me, it’s not an abstract discussion because all the emotions that they go through, I myself have gone through and had to work myself through. I did all the legwork and the research to find the tools to help me through it. When I decided to do this, I also went back to school and got a certification as a coach. I decided I would marry all my business experience and personal experience with reinvention, and I would go get my certification so I knew how to work with people as a coach to take them through it. I think all three together give me a really unique perspective.

The other thing, too, that makes me unique in this is that I’ve worked in corporate America and I’ve worked in line positions; I don’t come out of human resources. So I know from firsthand experience in terms of hiring what it takes because I’ve hired, and in terms of the politics of what you have to deal with in order to be successful in those environments. When I’m working with clients and teaching people, this gives me a very valuable edge because all the things that they tell me, I understand.

What are some common issues you’re seeing lately?

People are dealing right now with a lot of fear and sadness because of formerly safe industries, like media, newspapers, automotive, are going through such rapid changes that they feel very unsettled. They don’t really know where to turn and they’re mourning it because they didn’t really want this reinvention but they’re being forced into it. Then, the key is: What do they want to do next? There’s a desire that comes up pretty frequently to find a safe industry. What’s the next hot industry that I’ll be safe in? But if we learn anything from what’s happening now, it’s that there are no safe industries.

What advice are you giving your clients to deal with that?

We advise people to start by looking at what kind of lifestyle they want to lead. Not just financial needs but time-wise, how do we like our day to flow, what kind of work environment do we want — all of those things. Then once they’ve come up with this profile, then they have something tangible to begin evaluating which industry fit those profiles. Also, although we’re kind of on an upswing in terms of hiring, it’s not really pulling through yet, so people have to really extend their timeline for reinvention. What used to take six months to a year could now take 18 months or longer.

Taking that much time for reinvention can be difficult financially. What kind of advice do you give people in terms of staying afloat financially while going through this reinvention process?

You have to have what I call the Plan B job. You can’t reinvent yourself if you’re worried about how you’re going to make the rent. And there are people who come in who are out of work but really want to reinvent themselves and want to hold out. And I tell them to go get a job. Get some cash flow coming in, even if you have to temp. The thing about the Plan B job is that you want it to be not too demanding. It’s got to be easy for you. It can either be what you’ve done in the past, just doing it on a contract basis so that you have some cash coming in, or something that’s easy for you so you have the time to move toward your reinvention. Don’t take a Plan B job that is so consuming that you get stuck.

What advice are you giving to clients of yours from traditional media who want to get into the new media space?
The first thing with old media is to understand that the old way isn’t coming back and to deal with your emotions around it so that you can let that go and move on. Then the second step is, if you don’t have your new media skills, you should have them already. You’re overdue. But I really encourage you to go beyond that, to get an iPad and think about how are people experiencing information these days and what kind of skills can you bring to that. Where else do people need to be told stories? It’s not just in a newspaper.

One of the things I suggested to someone was to go look at the gaming industry. It’s now a multi-billion dollar industry with storytelling. There are opportunities out there once you take your mind out of ‘what other media outlets can I go to?’ and start looking at the skill of storytelling, the skill of reporting, the skill of editing, where are these things still needed? And then using those skills to move you forward as opposed to saying, I’m a reporter and I need to look for another publication or another network.’

What ways do you recommend someone find job openings?
By the time something’s on a job board, you’re already competing with how many people. I recommend really looking at the product. What trends are there and how can you contribute to those trends? You should be reading your paper and saying, hm, I’m reading about Starbucks moving into music licensing through their stores, or AOL wanting to hire journalists because they want to create content. That’s a trend. We think that content is what going to have people come here. And thinking, not just AOL is going to be hiring because they’re believing in content, but where else? All those companies that want to create rich iPad apps. You’ve got to take your blinders off and think that now there is this other platform; there are more people who need content in a different way. Once you’re out there, you can see, who do you know in those organizations? Have a conversation, and you can create jobs or projects that maybe don’t exist. So all of a sudden you’ve opened your pool for opportunity beyond just the job boards.

What do you think is the most important part of applying for a job — cover letter, resume, networking, etc.?

It’s all important but the thing that will probably kill you more than you might imagine is not having your materials — your resume, your cover letter, your “Hollywood pitch” — not having those targeted and shaped towards your target market. That’s what I feel is most important, especially when it comes to a reinvention. Many people look at an opportunity and say, I have the perfect skills for that, and they send it off and then they hear nothing. Why? Because they haven’t taken the time to shape their background so that it is targeted to that particular industry, so that those people understand what they have to offer. This is the most critical piece.

What’s one mistake that you made in your own career and how did you rebound from that?
Of course, I made a ton of mistakes. The biggest mistake that I made was quitting my job before I had another job. In retrospect, I look back and I think I had to do it because I was so miserable, but a couple of things: one I was two months away from qualifying for a pension. Dumb, very dumb financially. Two, maybe if there had been a company like mine, I probably wouldn’t have quit because I would have had a resource to turn to. But when you don’t know what you want and you quit a job, now you’re dealing with not knowing what you want and financial pressure, that’s a really difficult spot. And it’s not something I recommend for people, at all. People will come to me who are really unhappy and want to leave their job, and I tell them, don’t leave your job. Use your job as a launching pad to where you want to be. First and foremost, it funds your reinvention, it gives you a paycheck. Now let’s look at other ways that it can help move you forward.

Pamela Mitchell signs copies of her latest book and talks about transitioning to a new career in media at the Mediabistro Career Circus on August 4 in New York.

Amanda Ernst is deputy editor at Crushable.

Lisa Sugar turned PopSugar from a fun hobby into a successful, venture capital-backed new media company and blog network — in less than five years.

It all started with Pop, which Lisa launched in 2005 while she was still working as a media planner at ad agency Goodby Silverstein & Partners. Lisa drew on her husband Brian’s tech know-how and her own celebrity gossip magazine obsession, added a friendly, fun female voice, and watched as readers flooded in. “Within six months, Brian said, ‘Wow, these numbers are crazy,'” she said. “He had launched J. Crew’s Web site and he had launched Bluelight, which is Kmart’s Web site, so he’d seen how fast it took for sites to ramp up… And when he saw how fast Pop was taking off, he said, ‘Let’s turn this into a real business. This is like too good to not do something with.'”

The couple founded Sugar Inc. in 2006, and launched the new company on June 1, just as Lisa went into labor with their daughter, Katie. And as Katie has grown, so has Sugar Inc. Today, the company has about 120 employees, draws 12 million unique visitors per month to 16 different sites, offers e-commerce through ShopStyle (which it acquired in 2007) and lets users take advantage of its technology to start their own blogs with its OnSugar platform. Now, the company is looking to the next frontier: video.

Name: Lisa Sugar
Position: Editor-in-chief of Sugar Inc.
Resume: Worked at FOX in public relations and at Showtime network as a media supervisor before moving into advertising at Young & Rubicam and Goodby Silverstein & Partners in San Francisco, where she worked in media planning.
Birthdate: October 8
Hometown: Potomac, Md.
Education: George Washington University, where she studied psychology and English.
Marital status: Married 10 years to Brian Sugar, CEO of Sugar Inc.
First section of the Sunday New York Times: Style
Favorite TV show: “Right now, American Idol.”
Guilty pleasure: “Handbags, that’s my addiction.”
Last book read: Eclipse by Stephenie Meyer. “It’s required reading around here.”
Twitter handle: @lisasugar

How did you make the transition from advertising and PR to launching PopSugar and the entire Sugar network?

I would say that my background in advertising and media definitely fueled writing [PopSugar]. My favorite part of those jobs was having to know everything about every magazine and every television show and getting to watch pilots and all that stuff I had to know for my clients. I had a friend — Om Malik who writes a site called GigaOm — who was a writer, and he knew I would write things here and there. He was over one day and he was like, ‘You should really just start writing this and create the next celebrity online thing.’ That was back in February/March of 2005. My husband helped me create a site, taught me how to do HTML and code and all that fun stuff. And that’s when PopSugar launched, in March of ’05. I was actually doing that while I was at Goodby. It was the type of thing where I would be at work and I would take a break and I would go to all the large sites that people knew about then, like Gawker and People and stuff like that, but I would want them to just be updated more and more and more. And I just started writing every day and I started getting addicted to having people comment and looking at my stats and having more people come back. I think at the time when I launched Pop there was a niche in the marketplace. There were a lot of other celebrity blogs that were starting, but having the friendly female point of view was definitely different than what was out there, and people reacted to that.

So it all started with Pop, but how did it evolve into a bigger company with 16 different blogs?

Brian and I started looking at all the other categories that were out there. From my advertising experience, I knew the different genres of magazines and how big they were and how popular they were. No one was doing this online yet. I knew even when I was writing Pop that I wanted to write about a bag that I wanted to have, or I wanted to write about the new must-have beauty thing. And there was really no space for it in Pop. People didn’t want to see Britney getting her groceries and then the Jergens self-tanning cream that was all the rage one story after another. It just didn’t flow. So we knew we were going to have to launch various sites for everybody and they all wanted more, which was great. So we launched DearSugar, which is now part of TresSugar, which was the advice site with Q&A about love and sex. That was actually the second site. And then TeamSugar [the community site] and FabSugar. Those three came out of Pop all pretty quickly.

Sugar Inc. was founded in April in ’06 and in July we launched those other sites. And in September, we got funding from Sequoia, which was a big deal for us. They’ve been an amazing partner. And then myself and Krista, the managing editor who was one of the original staffers, went on a hiring binge. We went crazy hiring and training people and launching sites. We launched another four or five before the end of the year, and in ’07 we did another batch of site launches. So we kind of did it in two big waves.

That was almost three years ago now. How has it evolved since then?

We as a company realized there are other things besides the content that are really important. So purchasing ShopStyle [in the summer of 2007] was a really, really great investment and something we always thought editorially and as a company was always a really great asset for us. For example, you read a story on Fab and there is a Trend Alert, and I always wanted it to be a lot easier than a magazine. When you read a magazine, they sometimes give you information of a store or a Web site that might have it, but it’s actually really difficult to get the item that they highlight. So the beauty of having ShopStyle integrated into our posts is that it made it that much easier. If I’m going to tell you that a one-shoulder dress is in style right now and these are the cobalt blue colors that you have to have, there are 12 options right underneath and all you have to do is click and buy. So that whole concept is making it that much easier for a woman to get what they want, because we all know that the Web is great for instant gratification. That was a big thing.

What is your philosophy behind Sugar?

Our philosophy, and even our corporate culture, is just a very fun, laid-back environment. We want everything to be very approachable, so we don’t want our editors to seem standoffish. So that’s why our readers can actually get in touch with us, whether it’s via comments or email. It’s not somebody on the 55th floor in some corner office who is not going to respond to them.

There are so many other blogs that have names on every post, but at Sugar every post has a generic editor byline. What is the reason behind that?

That was something that started when we started the site. It was sort of like the girl in the corner and readers related to that. They would say, ‘Hey, Pop whatever,’ you know. And they gravitated towards that. I think it’s very obvious now that our sites are written by more than one person behind it and there’s a team behind it. So even if one person is writing one story and somebody else is writing something else, there are still a lot of people and eyeballs and brainstorming that bounces off of each other, so a lot of stuff is actually written in the collaborative format.

Were you affected at all by the recession?

Just at the time when the world was seeing some not fun things happen, we had actually just brought our sales staff in-house because we had just gotten big enough that we wanted to represent ourselves. So, for us, we were just ramping up our in-house sales team. Also, as a company, we run things pretty frugally. We like to act as a startup and be bare-bones, so luckily we’ve been in a great place the whole time. We have great investors and they continue to invest in us, so we’re in a good place. We just recently hired a bunch of engineers who are going to launch a game. If there’s an opportunity, we’re not hesitant. We just bought a company a year ago in May, and they’re helping us with the video. I think there’s so many ways to go with video, too, whether it’s actually on the Internet or actually on TV, we’d love to be producing beyond just online video. We’re still pretty young with video, but we’re ecstatic with the amount of people who are watching it and watching the whole thing. We think there are a lot of other directions we can go that we haven’t tapped into yet.

What advice would you give someone to launch a blog?

I think it’s actually easier now than it was years ago. OnSugar is a good example of the fact that anyone can do it. There are a lot of really great original writers, and I think that’s one of the great things about this day and age — everybody’s becoming an expert in their own world and they’re excited to share what they know. The tools are there and they’re easy to use and learn, so it’s a lot of do-it-yourself type teaching. For example, if you’re a fashion or beauty blogger, one of the things we have with ShopStyle is a thing called ShopSense, where you can make money off your links to ShopStyle, just like a lot of other affiliate programs. Depending on what category you want to write in, I think there are ways to make money. The biggest challenge for the writer is just, you know, getting the word out and consistently writing and challenging themselves to make it fun and exciting and getting people to find their site through networking and marketing on their own. A lot of it is our own editors are doing it on their own, or I did it on my own when I started Pop, just making friends with editors who are out there.

Do you ever look around and say, ‘Look at all the other sites we’ve surpassed and outlived’?

I think it’s sad when they aren’t still around. I think it’s interesting the directions that people take their sites and their visions. There are definitely people who are happy doing one thing and staying in that area and maybe owning that area, and then there are people branching out in a number of different ways. I think there is so much more out there than there was five years ago. But I think that the audience is different. The audience wants to read five things — they don’t want to just read one thing any more.

Amanda Ernst is deputy editor at Crushable.com.

Josh Lieb, executive producer of The Daily Show with Jon Stewart, has a dream job. But when the writers’ strike halted production of the Emmy Award-winning Comedy Central show, Lieb decided to use his time off to pursue another dream: writing a young adult fiction novel.

“I’ve always wanted to write a book, but it always felt like cheating on my job,” Lieb said. “Then we went on strike and I suddenly had months off and I had no income, and I was married and I had an apartment and dogs, and my wife and I were going to have a child. Writing a book sounded practical if I could do it.”

With a clever title and a few sample chapters, Lieb sold his book proposal and the movie rights to I Am a Genius of Unspeakable Evil and I Want to be Your Class President, which hit shelves on October 13, for around $1 million combined. That’s a big chunk of change, but still not enough to make him as rich as his book’s 7th grade protagonist. Now Lieb is a pretty busy man, promoting his riotous satire, which could be the childhood portrait of a James Bond villain — a fat middle schooler who is actually a rich evil genius bent on controlling the world, though he has trouble even making friends.

Lieb’s also working on the screenplay of the movie and outlining the sequel, I Am a Genius of Unspeakable Evil and I Want to Take You to the 8th Grade Formal, all while working at the funniest fake news show on TV. Still, the very busy Lieb is ever so humble about his success — as evidenced by his answer when we asked him where he keeps the heap of Emmys he’s amassed while working at The Daily Show.

“Mine are stuffed into the kitchen pantry right now,” he said. “They’re a weird thing. You don’t really know what to do with them. It feels very odd to display them in any way. I like them, I guess, but I don’t want to look at them every day, and I don’t want to lord them over anyone because I won them in collaboration with other people.”

Name: Josh Lieb
Position: Executive producer of The Daily Show
Resume: Writer for The Jon Stewart Show; writer and producer for sitcom Newsradio; joined The Daily Show in January 2007.
Birthdate: June 4, 1972
Hometown: Columbia, S.C.
Education: Harvard University
Marital status: Married with one son and a second baby on the way
First section of the Sunday New York Times: “‘Week In Review,’ the sports page for college football games, then the magazine.”
Favorite TV show: “The Daily Show is my No. 1 favorite show of all time, but otherwise right now I don’t watch a ton of TV because it would be all-consuming. The Andy Griffith Show and Sanford and Son, which aired in a block every night when I went to sleep as a kid, were very influential for me. They are two fine, very human sitcoms. That charm and hilarity are all you really need.”
Guilty pleasure: “Whiskey sometimes. I like to watch football games, and a friend talked me into joining a fantasty football league.”
Last book read: The Light That Failed by Rudyard Kipling. “I also read really bad books from the airport when I fly. That would be another guilty pleasure.”

What projects are you working on right now?

The main thing is The Daily Show, which is a full-time job. But I’m also promoting the book, I Am a Genius of Unspeakable Evil and I Want to be Your Class President, which [came] out October 13, and I’m very excited about that. I’m also working on the screenplay of the book for Warner Brothers, and hopefully that will start filming some time next year. I’m also working, only in the notes on the moment, on the sequel to I Am a Genius, which my publisher Razorbill is being very patient about. And The Daily Show is also collaborating on another book, which is also a lot of work, so I’m spinning a lot of plates right now.

What is this new Daily Show book?

I don’t even know if it’s been announced, so I’m almost afraid to talk about it. But I can say that if you liked America the Book, you’ll love this one.

Tell me about your work on The Daily Show. What’s a typical day like for you?

I get into work around 9:30 [a.m.] and we’ll have a meeting with some of the writers and some of the people from the studio department — who are the people who put together the montages — and our head researcher. And then Jon [Stewart] will usually join us, and we’ll talk about what is in the news today and who we are planning to have on the show that day. The studio department people will show us clips of things that they’ve seen or might be working on. Head writer Steve Bodow will dole out the assignments to the gathered writers, [and] then we’re in meetings for hours with all the departments about the day ahead.

Later, me, Rory Albanese, Steve Bodow, Kahane Corn, Jim Margolis and some of the other producers will meet with Jon again to talk about what’s going on that day. We complain about our families a lot. Then the scripts start coming in. We start reading scripts, picking jokes, asking writers to do rewrites or fold ourselves into groups of writers to do rewrites. We’ll go into a conference room with a projector and put the script up on a big screen, and three or four of us will sit in a room and go through it. We’ll bring in Jon, and he’ll sign off on things.

In the early afternoon, there’s a lot of prep to be done before rehearsal: mock ups to be made, clips to be pulled, revisions to the script. Around 4 or 4:15 [p.m.], we’ll rehearse the show and we see what works. And then we’ll make notes and go off and Jon, me, Rory and a writers’ assistant and script supervisor will sit in a room and do a script rewrite. The show is at 6, and hopefully we’re done by 7. I usually get out of the office around 7:30. There are people who work much worse hours, and I’ve been in jobs where I went to work on Monday and came home on Wednesday. I am grateful to have a job that allows to have me a family life.

The show has become known for its video montages. How do they come together?

It’s kind of magical. It’s a brilliant collaborative mind that makes it all happen. We have a lot of really savvy people working at the show who all watch all these disparate shows. We have this amazing, talented, very funny writer who watches Fox and Friends every morning. Nobody asked him to do it, but he does and he’ll come in and tell us if something funny happened that morning. Then we have an entire department, the studio department, devoted to recording every channel and keeping track of it. Jon is a real stickler for the montages. We obviously take a great deal of pride in them, because they really do have so much impact in a very short time, and they can be very funny.

With so much to get done every day, what is the work environment like?

You find that a lot of comedy shows can be a caustic environment, and there is some of that here, but this is definitely the nicest environment I’ve ever worked in. I think that comes from the top, from Jon. I remember on my first day on the job, I went to the break room and there was a sign on the fridge that said, “If you don’t clean up after yourself, who will?” And I was reaching in to the pocket to write “Your mother” on it with my pen, and I looked at this paper and it was obviously aged and yellowed and nobody had written graffiti on it yet. I realized I would have been the guy who would do that his first day, so I decided against it. It’s a rare environment, but it’s kind of a safe haven.

The Daily Show just won its seventh Emmy for Outstanding Variety, Music or Comedy Series, and you also won the Outstanding Writing award this year. Does it ever get old?

Not for me, but I’m comparatively new here. The best writing award this year was very gratifying. Winning Emmys is great. If any of those shows that were nominated win, it’s well-deserved and no one can feel cheated. But it’s definitely nice to bring home that award. I don’t think Jon really cares one way or another, but to everyone else it’s absolutely gratifying to get a nice shiny trophy.

How did you come up with the idea for I Am a Genius of Unspeakable Evil and I Want to be Your Class President?

I wish I could say there was a eureka moment when I saw a fat kid on the street and said, “He looks dumb, I wonder if he’s faking.” I love young adult books, not only when I was growing up but still to this day. I love the power fantasy element of them — like in Harry Potter, for example — when someone unexpected is actually so powerful. So many of the characters we love as kids we love because he is a super detective, or she is super strong and can eat 1,000 hamburgers. [The book’s main character] Oliver fits right into that wheelhouse. I came up with the title and impressed myself with what a good title it was. Then the book wrote itself.

I really wrote the book not just for young adults but for people like you and me who continue to read young adult novels. I wrote it like the books that I really remember and love, the ones that really challenged me. I didn’t know what they were talking about, but they didn’t impede me, books that made me feel like I was being led into an adult conversation and I felt like that was what I would be talking about in five or 10 years. I wrote one of those books. It has some more complex ideas in there that adult readers will enjoy. So I can see college kids walking around with a copy of it.

Your book deal and movie option made big news last year. Is it true that you’re going to make over $1 million from this?

I don’t think that’s accurate. I know I didn’t sell the book for half a million dollars, but if everything follows right and the movie gets made and I get full credit, I think it could add up to $1 million or so. God willing that will happen, but there are so many slips that can happen in the movie world. All the numbers meld together to mush in my head and all I know is that if I hand something in, I should get a check for it. If I was good with money, I wouldn’t be a writer.

The big news in the TV comedy world right now has been the David Letterman scandal. What was your reaction to the news?

It looks like he handled it magnificently. It looks like the worst situation imaginable. Now, of course, we’ve got 100 tabloids that are going to dig into it, and we’re going to hear all the sordid details about it over the next six months. But he did all he could to take the guts out of it, and I applaud him for that. As someone who has a real relationship with his audience, it was the right forum for him to share personal things with the audience on his show.

Amanda Ernst is editor of FishbowlNY.

It’s the conundrum that still has media execs scratching their heads: If the Internet is the future of media, how are they supposed to make money from it? Consumers are used to getting just about everything for free on the Web, especially when it comes to news and other original content. So, the challenge is convincing people who haven’t paid for something to start paying for it. That’s easier said than done, which is where the “freemium” model comes into play.

Using freemium, companies are able to offer their products and content for free to some, while others can pay extra for advanced features and capabilities. One tech startup testing the freemium waters is HootSuite, whose product of the same name is a dashboard allowing teams to manage all their social media accounts in one place.

HootSuite’s CEO Ryan Holmes, a speaker at mediabistro.com’s upcoming Freemium Summit East, can talk about why his company has decided to recently launch a freemium paid content model — “we didn’t want to cannibalize our growth” — but don’t ask him to give other companies advice about using freemium. At least not yet.

Name: Ryan Holmes
Position: CEO, HootSuite
Resume: A “serial entrepreneur,” Holmes launched his first company, a paintball field, in high school. Then he started a restaurant, but got into tech right at the dawn of the boom in 1999. He worked at a now-defunct dot-com shortly before launching his own digital agency, Invoke, in 2000. HootSuite, an application developed by Invoke, debuted as a standalone company in January 2010.
Birthdate: December 30, 1974
Hometown: Vernon, BC
Education: University of Victoria
Marital status: Single
First section of the Sunday NY Times: Business
Favorite TV show: Mad Men
Guilty pleasure: Yoga
Last book read: Born To Run by Christopher McDougall
Twitter handle: @invoker

How did you go from restaurateur to tech entrepreneur?

I sold the restaurant in ’99, and I was always interested in computers. Web was blowing up at that point, so I basically self-taught on HTML and managed to put together a decent enough portfolio to get a job at a dot-com. I worked with them for about six months and honed a lot of my skills there to a point where I was able to found Invoke.

How did HootSuite get off the ground? And how did it get from there to where it is now?
Invoke was working on a bunch of different social media campaigns for clients, and we needed a tool to help better manage our campaigns for our team and our clients. We were looking for a tool and we just couldn’t find one, so we decided to start building one. That was really the inception of HootSuite.

One of the most interesting things about HootSuite is its use of the freemium model. How does it work, and why did you choose to go in that direction?
By the time I speak at the conference, I’ll have a lot more information for people. We just launched it for new users. We’re investigating how it’s working for people and seeing what they’re liking and what they’re hating, and having success so far. We decided to go with freemium because we didn’t want to cannibalize our growth, so we wanted to keep the product free. We think it’s important to have a strong base of users out there who are passionate about the product, and we have very passionate users and loyal fans who use our product every day. We go to conferences and meet people there, and [I] introduce myself and it’s really amazing to see people’s eyes light up. They say, “Oh my god, you’re with HootSuite, I use your product every day.” And it’s funny because I don’t think anyone gets that passionate about like, “Oh, you’re with Outlook, I use Outlook every day.” Or “Oh, you’re with Firefox, I use Firefox every day.” So we have really great fans and users who ultimately evangelize for us. And then on the paid side, we have people who really need good user functionality and a solid tool, and we’re able to provide that for them… We always had plans to monetize through freemium.

How does it work? If you’re joining and you’re a new user, you can choose to upgrade to paid use?
Exactly. It’s free for — we’re actually thinking it’s going to be free for about 95 percent of our users and paid for 5 percent. The pay wall usually shows up based on the number of paid users so if you have a large teams you’re going to end up being on the pay plan, or you can reduce your team size down… but that’s kind of one of the big matrix of payment. We have other features like support and increased analytics that also go with the pay plan.

What percentage of HootSuite’s users are companies versus individuals?
We have a lot of companies using it. We have a huge base with small and medium enterprise users. We have power users as well, but for the most part, we don’t have consumer users, we have users who need bigger better tools. That’s really where our base was at. In terms of actual numbers, I don’t have the statistics offhand. It’s really hard for us to tell, even from looking at our data, where the business versus power user split is.

How does HootSuite make money besides freemium?
Through the history of Invoke we have built new products that were successful from day one. So we built out an e-commerce platform, we sold it to a client and they continued to sell it. Same thing with our video conferencing platform. With HootSuite, it was a little bit different. The launch was moving so quickly, we had a small team dedicated to it, but we just needed to keep our velocity up. So we kept that going for over a year of bootstrapping it, self-financing it. And then it got to a point where it was blowing up and so it made a lot of sense to take on some investors. So we took on investment in January 2010 and we continued on with that. But our goal is to get to profitability, and we’re pretty much there.

A lot of media companies are trying out freemium. Why do you think freemium is a good choice for media companies?
I think that with regards to media, I’m not sure it is [a good choice]. But I know for products, it definitely is. I think it can be a good way to get people in and get eyeballs on your products, or content for media companies. I think it’s one of the proven models that’s out there right now. But right now there’s definitely more that will be discovered, and we’re at an interesting point in time for the discovery of new ways.

Do you think media execs are rightfully worried about getting users to pay?
We’re definitely going to see a reinvention of media companies. One of our investors is a media company: Hearst. So they’re looking at diversification in this era; the way that media is distributed and the content that is being created have completely changed. And if you don’t adapt, you become a dinosaur, like the music industry. If they had their way, everybody would be going to retail music stores and buying jewel case CD albums. But I think the video industry learned some things from the music industry and kind of adapted. With the media industry or content and publications, I think they’re diversifying a lot and they’re looking for other ways of creating content, different models, and I think that they’re actually appearing to be the most adaptable in a lot of ways.

Ryan Holmes details how to make the transition from free to freemium at the Freemium Summit East on October 25 in New York City.

NEXT >> Hey, How’d You Use Social Media to Crowdsource A Cookbook, Food52?

Amanda Ernst is a freelance writer living in New York. She also manages business development and social media marketing for B5 media, the publisher of three women’s lifestyle sites.

Lucking into a position as a magazine editor through friends and connections seems like a classic old media story. And that is exactly how Deborah Needleman says she came into her position as editor-in-chief of the now-defunct Conde Nast home lifestyle magazine Domino.

But Needleman’s story took a decidedly modern turn in 2009, when Conde shuttered Domino, putting her out of a job. And with very few magazine editor positions remaining in the industry, it was over a year before she ended up in her current position, launching The Wall Street Journal‘s Saturday style section “Off Duty” and working to revamp the financial paper’s luxury lifestyle magazine, WSJ. She’s already been through the failed magazine thing once, but she thinks this time will be different.

“I think there’s still a place for magazines as one of the ways we consume media,” Needleman said optimistically. “And I think as long as there’s newspapers there will be newspaper magazines.”

Name: Deborah Needleman
Title: Editor-in-chief of WSJ. and editor of The Wall Street Journal‘s “Off Duty,” a Saturday style section launched in September.
Birthdate: November 23
Hometown: Cherry Hill, NJ
Education: George Washington University
Resume: Worked as a photographer’s assistant and “pretty bad freelance photographer” before becoming a photo editor at The Washington Post‘s Sunday magazine. Then she wrote about gardens and design for The New York Times, Slate and House & Garden, where she was editor-at-large. In 2005, she helped found Domino, which folded in fall 2009.
Marital status: “Very much so.” (She’s married to Slate Group editor-in-chief Jacob Weisberg)
Media idol: “I have two: Arianna Huffington and Susan Lyne, chairman of Gilt Groupe and former CEO of Martha Stewart Living Omnimedia. They both manage to do a lot, do it creatively, do it in their own way and are still incredibly warm, fun people. I think they do work well.”
Favorite TV show: Friday Night Lights and 30 Rock
Last book read: Just Kids by Patti Smith
Guilty pleasure: “It changes all the time, but right now it’s solitaire on the iPad. It was Angry Birds and now solitaire is on it’s way out, but it’s still there.”
Twitter: @debbieneedles

You say that your path to becoming a magazine editor was non-traditional, so how did you get the job as founding editor of Domino?
I was really fortunate that someone took a chance on me and gave me a job that my resume didn’t exactly warrant. It wasn’t like I was on a clear or a very ambitious trajectory to become a magazine editor, I wasn’t. But then I really was lucky and I conceived this magazine solely in my head and amazingly was given the opportunity to realize it.

It was based on a lot of the premises of Lucky. I came to James Truman, who was then the editorial director of Conde Nast. It was amazing. I was so lucky that he saw it in me even though it wasn’t apparent.

So you had this idea and you pitched it to James Truman? It was really that easy? That sounds incredible.
I had the support of Kim France, who was the editor-in-chief of Lucky at the time, and she was a friend of mine. And she made the introduction. It was an amazing, lucky confluence of events and timing.

How did you learn that Domino was closing?
It was very similar to when my parents got divorced. My parents always got along really well, and then one day my mother called me aside and I just knew what she was going to say. And this was the same thing. I had heard rumors about Domino, but it really was successful. Its newsstands sales were up when everyone else’s were down or flat; it was growing and had all this consumer engagement. So I didn’t really believe the rumors. And then Tom Wallace, who was the editorial director, called me up -– and he would call me up all the time –- but for some reason that day when he called me up it was the same thing, just a pit in my stomach. Like, ‘This isn’t going to be good.’

You certainly weren’t alone at being suddenly out of work. What did you do next?
As sad as I was, it was a huge and great break. I had worked so hard for five years and put so much of myself into that magazine that it was actually kind of a relief. Not that I wanted it to happen, but it was great to have a big change. I was so absorbed in the magazine, and it was nice to just walk around the city in the middle of the day. If the unemployment had gone on longer I wouldn’t have been very happy. But I was really, really happy for the break, because we all work so hard mostly from the time we can work, and we rarely get a big break. And it’s kind of great.

Were there ever talks about Domino coming back in another form, like Gourmet‘s iPad app?
I was actually in talks with Conde Nast about licensing the name Domino for a Web business that I was going to do. There were all these rumors about them doing all these Domino-related things.

How did you end up at The Wall Street Journal?
It wasn’t like anyone was beating down my door, and then this thing just landed. Someone recommended me to Mike Miller, who is the deputy editor [of the Journal], for this section that they wanted to start. They genuinely liked and appreciated Domino and it was that sensibility, although it’s very different from the Journal, that they wanted to bring in a sense of liveliness and style. And so it actually wasn’t a crazy leap. It’s not like I’m heading up the political coverage.

Has The Wall Street Journal ever tried luxury and lifestyle sections or magazines before?
The Journal started the magazine two and a half years ago. The Journal had been a business publication and it’s been expanding consistently, especially since Rupert Murdoch bought it. So they started with the New York section; then they started covering more general news. They’ve been expanding and the lifestyle coverage is the latest part of their expansion.

Do you think the fact that WSJ. is owned by The Wall Street Journal will help it to survive better than if it was a stand-alone luxury magazine?
It has the power of The Wall Street Journal behind it, but it’s its own separate business within the Journal. It’s not being bankrolled by the Journal, but there is the support of the greater paper. The editorial support and the resources I can pull are incredibly helpful, and the sales team is selling not just the magazine but the entire Journal franchise. So, it’s a much stronger sell than just going out and selling the magazine individually.

The Wall Street Journal typically has a mostly male audience, but the audience of luxury magazines is usually female. How are you trying to bridge the gap between those two audiences?
Part of what I’m trying to do is broaden the reach of the newspaper’s readership. It used to be much more male dominated and now I think it’s 60-40. And so the gap is being bridged. A lot of what I hear about people reading “Off Duty” and the magazine is, ‘Oh my God, I didn’t know The Journal did this. I got it from my boyfriend or my husband.’ So I think it’s a shift that’s still happening. But the idea is that the kind of news and information that the newspaper and these lifestyle sections offers is not like a boy’s playground –- it’s for everyone.

What advice would you give to someone who wanted to become an editor of a luxury magazine?
I can’t imagine someone would go to college these days and think, “I want to work at a magazine.” It’s about creating a product — an interesting, enlightening, amusing editorial product — and that can be done in so many ways now, magazines just being one of them…I do think luck is important and putting yourself in situations where you might be the beneficiary of luck, if that makes any sense. It’s going to sound corny, but people just need to put their happiness first…It’s not worth slogging through something just to get somewhere else…I think it’s just about reading a lot, and being open to things and being open to chance.

Would you advise your kids to become a magazine editor?
No way! But then again, who knows? If you really love magazines, I bet there will always be a way to do something great.

NEXT >>

Amanda Ernst is a freelance writer living in New York. She also manages business development and social media marketing for B5 media, the publisher of three women’s lifestyle sites.

While readers of New York magazine generally pick up the weekly for its award-winning journalism, local shopping or restaurant coverage, or even the “Approval Matrix,” there are plenty more whose first flip is to the crossword puzzle in the back of each issue.

Unlike its more high-brow sibling in the Times, this grid doesn’t require a reader to be a member of Mensa to solve it. New York puzzles are challenging enough to make an F train rider feel smarter than the person next to him, but accessible enough for the liberal arts grad who may not know how to spell Kazakhstan.

And, for decades, the sense of accomplishment readers got from cracking a difficult clue can be chalked up to master creator Maura Jacobson, who has been crafting the word puzzles for the magazine since 1980. New York readers’ love for Jacobson’s work became evident when she announced her retirement after 31 years at her post, resulting in an outpouring of support. (One reader even equated Jacobson’s stepping down to “losing a family member.”)

“I just couldn’t believe anyone was sorry I was leaving,” Jacobson said, modestly. “I’m really proud of that.”

Name: Maura Jacobson
Title: Longtime crossword creator for New York magazine
Birthdate: April 28
Hometown: New York City
Education: B.A. from Hunter College
Resume: Quit teaching kindergarten when she had her daughter, and created a puzzle on a whim and sent it to The New York Times. In 1971, started creating consistent puzzles for the Times, and later Cue magazine. When Cue was bought by New York in 1980, she came, too, creating a puzzle a week for the magazine for the next 30 years. (She’s been doing a puzzle every other week for the past year leading up to her retirement).
Marital Status: Married, with one daughter
Media idol: Margaret Farrar, the former crossword editor at The New York Times, “If it wasn’t for her, I would have never been in the job.”
Favorite TV show: Baseball games — she’s a Yankees fan.
Guilty pleasure: Chocolate
Last book read: None

How did you get into professional crossword making?
I would play with crossword puzzles in the magazines or in the newspapers. And, one day, I decided to try my luck and made up a terrible crossword puzzle which had made-up words in it. And, very brazenly, I sent it to the Times and the Times‘ editor of puzzles at the time, Margaret Farrar. If she had simply said, “I reject this. You made up words,” well then I never would have sent in another puzzle to anyone. But she was gracious. And she said, “I cannot find these words anywhere. However, if you want to try again, I can make a few suggestions.” So that was big news. You know, you get your name in the Times.

So I followed her suggestions, and she published the puzzle, and I started making larger puzzles for the Sunday edition. And then after a while, I lost interest, really. In 1971, I had a very bad auto accident which kept me off my feet for a year, and Margaret, again, sent me graph paper and she said, “Stay with it and it will be okay.” And then she had to resign because The New York Times at the time had a ruling that you couldn’t work after [age] 70. The position was taken over by a wonderful man, Will Weng, and he apparently liked my puzzles.

When New York magazine bought Cue, did you continue to create crosswords for the Times or just New York?
When I started working for New York magazine, I stayed with them only and I’ve had maybe one puzzle in The New York Times since. [New York Times crossword editor] Will Shortz was always asking me for puzzles for the Times, but I didn’t have time to do both.

There is this whole community of passionate people who create crosswords and love them and do them fanatically. I know that you take part in the Crossword Puzzle Tournament, so how did you get involved in that community?
There was not very much contact between the people who made puzzles until 1977. Will Shortz was a young man from Indiana, and he was trying to make a place for himself. He was asked to make up a crossword tournament at the Stamford Marriott, because it was a business hotel and they wanted people to stay on the weekends when business was not being performed. So, he undertook this because he really had nothing else lined up. And that was in 1977; he’s been doing it ever since. I’m the only person who he has asked for a puzzle every year since, which I have given him.

People say that your puzzles have very unique attributes. What would you say is your trademark?
I try to make the puzzle solvable, just simply that. I think other crossword makers try to fool the solver and I don’t. I just go straight and apparently that gives people a way to move and they enjoy coming up at the end of the puzzle and being able to say, “I finished it! How smart I am.” You know? And I feel I would like to be that kind of solver, so I do it for my puzzles.

Have you ever made a mistake in a puzzle and been called out on it?
I can’t remember ever finding an error, except in my very last puzzle for New York magazine. And it’s not my error — there was an error in the clues, a misprint or something. And that bothered me, because I used to go over every single word and I don’t know where this crept in. I had a young lady at New York magazine who went over every word with me, and I checked this after I saw the mistake. Apparently, the mistake went in at the printer, I think.

Is there enough money in crossword puzzle making to do it full time?
There’s not enough money in it unless you have a weekly job. If you have a weekly job, then yes, you can manipulate that. But if all you can do is send a puzzle to the Times or some other publication and have one accepted and one rejected, you’re not going to be able to have a steady income.

What about getting into it? You sent a puzzle to Margaret. Is that still the way to go?
I got lucky, and I was lucky with Will Weng as well. He liked my puzzles and he would go out of his way, I felt, to put me in the Times. And that helped. Today they would send a puzzle to Will Shortz or to another editor. Will Shortz will give your puzzle consideration and if it’s good enough they’ll publish it. I see a lot of names in the bylines in the Sunday Times puzzle. So, there are a lot of new names in there, and these are people who took the puzzle they made and sent it to Will Shortz. That’s really the only way.

Has anyone ever sent you a puzzle for advice? Have you ever mentored anyone?
I’ve given advice but [finding other people to create puzzles] wasn’t my job, so I didn’t really go at it.

What if someone wanted to send you a puzzle now and asked for your advice?
I’d rather not be involved anymore.

What are your plans now that you’re retired?
I’m planning to do some reading, because as you may have noticed, I couldn’t come up with the name of the last book I read.

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Amanda Ernst is a freelance writer living in New York. She also manages business development and social media marketing for B5 media, the publisher of three women’s lifestyle sites.

Clara Shih literally wrote the book on how companies can use Facebook to promote and market their products and brands.

After creating the first business application for Facebook, Shih put her insight and research on marketing and social networking sites into The Facebook Era, which is now being used as a textbook at Harvard Business School. Shih later founded Hearsay Social, which offers companies a technology solution to better manage their social media. So, if you’re planning to hear Shih speak at AF Expo later this month, you better believe she has the experience to back up her advice.

Yet, Shih is modest about her influence in this relatively new world and is wary of self-proclaimed ‘social media experts.’ “Only about once a decade do you have such a massively disruptive technology that creates this window of opportunity for true innovation and for really big businesses to be built from the ground up, taking advantage of the new normal,” she said. “Anyone can learn to talk the talk, but who’s actually shown, through their actions and the results they’ve received, that they can execute against a strategic business?”

Shih can.

Name: Clara Shih
Position: CEO and founder of Hearsay Social
Birthdate: January 11
Hometown: Born in Hong Kong but grew up in Arlington Heights, IL
Education: Studied computer science as an undergrad and graduate student at Stanford University. Received a second master’s degree in Internet studies from the University of Oxford’s Internet Institute.
Resume: Worked at Google before joining Salesforce.com, where she managed AppExchange, the company’s marketplace for partner solutions. Used knowledge from both jobs to create the first business application for Facebook, Faceforce, in 2007. Researched and wrote The Facebook Era, then founded Hearsay Social, which launched in beta in February 2011.
Marital status: Engaged
Media idol: Sheryl Sandberg from Facebook. “She’s a mentor of mine,” said Shih.
Favorite TV show: “Embarrassingly enough, I don’t watch TV.”
Guilty pleasure: Playing Facebook games. “My favorite is Bejeweled Blitz. Every week, I have the high score in my network. It’s something I’m very proud of.”
Last Book Read: Little Bee by Chris Cleave
Twitter: @clarashih

What was your initial vision for Hearsay Social and do you think it has lived up to that vision, surpassed it, or evolved into something else?
Well, I think it’s going to be a long road. Certainly, we’re off to a fantastic start. We launched in beta in February, and we have tremendous customer and market momentum. Our initial vision, and it’s still true today, is that we recognize that social media has changed the relationship and interactions that companies have with their customers to one that’s much more ad hoc, much more real time, much more authentic. And also one that’s much more two-way instead of one-way.

In your opinion, how important is it for a company to have a social marketing strategy? What if a company wants nothing to do with Facebook?
A lot of people said that about the Internet 15 years ago, but can you imagine today being a business and not using email or not having a website? It definitely depends on the company. It depends, number one, if the target audience is on the particular social network. If you’re a business and none of your customers are on LinkedIn, then you don’t have to worry about LinkedIn. On the other hand, if they’re all on Facebook talking to you, then you should probably be there. The other thing that matters is customer expectation. Even if your customers are on Facebook, is there demand from them to interact with your brand on Facebook?

Do you think these sorts of social media strategies are something companies can do in-house, or should they look to companies like Hearsay Social to help them?
It depends on the size of business. Hearsay Social is a technology that lets their team more effectively manage social media. Whether it’s an in-house team or a digital agency or a combination of in-house and out of house, it’s really up to them. As a general piece of advice, it’s good to at least have a couple people in-house who are involved in social media, because social media so embodies the voice of the customer that, as a business, there is tremendous benefit to staying close to that voice.

What are some of the biggest mistakes you’ve seen companies make with social media marketing?
I think one is acting before they listen. There’s this wealth of conversation that’s taking place on Facebook and on Twitter every day — if not about your brand, certainly about your products, your industry and your competitors. So, to act without doing your homework and researching is really missing out on a big opportunity to get a pulse on what the market is saying. The second major challenge that I see is oftentimes businesses will create a social media presence via a Facebook page or Twitter page and then — especially when things get busy, and you’re a small business, and there’s all these other things you have to worry about — they forget about it. And there’s not the continual, consistent maintenance on these pages. And what you end up with is these ghost towns on social media sites…and it’s a turnoff for customers.

What advice would you give businesses, or even bloggers and media companies, about responding to angry commenters or dissatisfied customers?
It’s important to understand the reason why they’re angry. If it’s a legitimate complaint, there’s also the view that having one negative review actually increases the overall engagement of a page because it increases credibility. Response is key; tone is key. I think that the fact that someone is upset and expressing that to the brand is a great sign, because it gives the brand a second chance to win that person over.

Are there brands that are doing social media particularly well?
There are a lot of brands that are doing it well. Farmers Insurance, for example, they have a very successful, engaging corporate Facebook page with over 130,000 fans. In addition, they have 15,000 agents, about a third of which have their own Facebook pages, representing their community. And they’ve been really innovative both in terms of catering [to customers] at the corporate brand level and empowering each agent to represent the brand with their own unique and authentic voice within social media within all the brand’s regulatory guidelines.

On Facebook, what is the more powerful marketing tool: brand pages or ads?
I think you have to have both. We found a higher conversion on ads when you have a brand page. Obviously, if you have created a brand page and it’s not good, it’s not engaging, even though you have someone click through, they’re not going to stay on there and take the desired action. Step one is to listen first; learn about the communities. Step two is to build your presence proactively, and step three is to drive traffic and engagement to your presence through ads and other campaigns.

At the AF Expo you’re going to talk about the “7 Habits of Successful Facebook Marketers.” Can you give us a sneak peek?
I’ll give you a preview of three of them. The first one is to get targeted and get local. Using this whole new world of insights that we have from social networking sites, companies have an opportunity to make their messages to customers much more targeted, and there’s all sorts of things that arise from that, including higher conversion rates, more engagement, more sharing, etc. Two is to embrace content. We’ve known for a long time that content is king, and it couldn’t be more true today with social media. You can’t just create a Facebook page or Twitter and walk away. The whole point of social media is continuity and continual engagement.

And then the third one I’ll preview is that it’s still early. So, keep working and have fun with it. There’s a number of really fun and interesting campaigns that, if you were to do it again, it wouldn’t be innovative again because someone had already done it. But — like when Farmers Insurance sponsored Farmville, and Farmville players on Facebook could put a Farmers virtual airship over their farm, and it would provide virtual crop protection — that was a great way to achieve brand engagement with an audience that spent a lot of time on Facebook.

With this new industry changing and developing so rapidly, where do you see social network marketing going in the coming months?
This is a really exciting time for social media. 2010 was all about social media strategy. For the first time we saw CMOs and CFOs, across a number of different industries, from small business to Fortune 500, truly start to prioritize social media, get educated and start talking about it at the executive level. 2011 is all about social media execution. And we’re seeing budgets being created and teams being formed. Roles like Social Media Manager and Social Media Director that just didn’t exist 18 months ago now are some of the fastest growing roles within those companies.

If someone was interested in getting one of these new jobs, what are some things employers are looking for?
It’s understanding the different use cases but also being able to creatively brainstorm new applications and get results. Results don’t have to be for a big brand. You have to start somewhere. So, try running some type of campaign of your own or create business pages — something that you can use to show growth and engagement. That all speaks volumes.

Clara Shih details the “7 Habits of Successful Facebook Marketers” at the AF Expo held from June 28-29.

NEXT >> So What Do You Do, Justin Osofsky, Head of Media Partnerships for Facebook?

Amanda Ernst is a freelance writer living in New York. She also manages business development and social media marketing for B5 Media, the publisher of five women’s lifestyle sites.

If print and digital have to learn to work together, Brandon Holley is one of the few people equipped to lead the way. After working for years atop the mastheads of marquee titles from Time Out to Elle Girl (which she helped envision and launch) and, perhaps most infamously, Jane, Holley found herself unemployed. Like many print castoffs, she found opportunity with a digital company, Yahoo, which used her expertise to help drive millions of readers (over 24 million in October 2010, according to Comscore) to their women’s channel, Shine.

But despite her success at a digital brand, this fall Holley returned to the fold of the media company that had tossed her out in 2007, Conde Nast, replacing Kim France at the helm of shopping magazine Lucky. Now, she’s looking to combine her knowledge and experience to expand Lucky‘s website and digital reach. “I didn’t ever think that I wanted to come back to print,” Holley says. “But what Lucky offers is so cool when you think about what print and digital can do together. It made me think, ‘Oh, here is a good way for me to use both sides of my brain.'”

Name: Brandon Holley
Position: Editor-in-chief, Lucky magazine
Birthday: November 27, 1966
Hometown: Great Falls, Virginia
Education: BA from Barnard College
Resume: Started writing articles for Paper magazine, then got her start at “one of those insecurity driven women’s magazines” before moving to fashion trade pub Sportswear International, where she became executive editor “waaaay too early.” Left to work for Cyndi Stivers for the launch of Time Out, then moved over to GQ. Led the launch of Elle Girl at Hachette Filipacchi. Took over for founding editor Jane Pratt at Jane, which folded in 2007. Helped launch Yahoo’s Shine before joining Lucky in September 2010.
Marital Status: Married
Media idol: Byron Dobell, former editor of Esquire. “He was amazing. I met with him when he was inducted into the ASME Hall of Fame and had lunch with him.”
Favorite TV show: 30 Rock
Guilty Pleasure: Knitting
Last Book Read: Winter’s Tale
Twitter handle: @brandonholley5 “I don’t do anything. I follow people. I do not do anything.”

How did you find yourself back at Conde Nast after the last magazine you ran there was shuttered?
Online was pretty exciting and thrilling…Spending three years launching one of the biggest women’s sites in the world now –- it’s pretty big -– and really learning what women in that community were doing, seemed to translate really nicely to that core thing that Lucky does. So it sounded exciting when I hadn’t expected it could be like that.

As a loyal and longtime Lucky reader, I’ve always felt that Lucky‘s website and digital presence has been lacking. How are you planning to update and improve it?
Any magazine has got to be thinking about the digital side. That doesn’t mean that magazines will go away. Magazines have to be around otherwise it’s just a sea of digital brands. The print is what separates us. The opportunities for Lucky digitally are huge, huge, huge — but only with the print as the jewel in the crown. Otherwise we’re just another women’s site, and there are plenty of them out there. But print separates us from the crowd.

How are you going to bring your experiences at Shine to Lucky?
Shine was focused on community and women sharing and [blogging]. So as soon as I got here, I started planning for the Lucky Style Collective, which is a collection of bloggers who will create content for the magazine, whose businesses we will help to develop. They’ll come to editorial meetings. If you look at the fashion bloggers, they’re the Lucky reader. She’s mixing vintage with Marc Jacobs with something from H&M. It’s a very modern way of dressing and that whole street style thing is incredibly Lucky. We recently did this Fashion and Beauty Blog conference that was pretty cool. And now we’re doing this Lucky Style Collective to bring all these great blogger voices into not only our digital platform, but also the print magazine.

What type of criteria or tools are you using to find these fashion bloggers?
Well we just had brunch with some of the top fashion bloggers on Tumblr. So it’s basically what I’ve always done, right? I’ve always had dinners with readers. When I was at a teen magazine, I always took a lot of time to meet with teens who were writing for their high school newspapers. Basically I just go meet with fashion bloggers. If we like each other, we roll them into the Collective. It’s just about getting more and more voices. I think it’s really exciting; women writing about fashion instead of just editors [writing about it] is very exciting to me.

What, if anything, do you think has changed on the print side of magazines since the last time you were there?
I think there’s a lot of openness to experiment, both from the corporate side and from the staff side. I remember three years ago, there was a little bit of resistance to embrace online, and now almost every editor at Lucky is tweeting, has a blog and wants to write online. There’s no firewall between print and digital anymore. It’s a completely porous relationship, which is great. And also, corporately, if I can come up with an idea and it makes sense, there’s a lot of willingness to try it out.

Do you think there’s a future for magazines? How do you think combining digital and print factor into that future?
It depends on the magazine, right? There’s something about fashion and print that has not been rendered properly online. I don’t know, maybe if you’re a weekly news magazine or an events magazine, it’s a different thing. But if you’re about incredibly good writing or incredibly good photography or in fashion — The New Yorker is an example of a magazine that just makes sense in print. But, if you’re talking about a classifieds type of magazine, that should probably go online. So I don’t think all magazines will be fine. But, because of the photography and the layout and the design, magazines are something that people won’t let go of. But that doesn’t mean they can stay the same. They also have to have a digital expression.

What has been the reaction to you coming in to Lucky and replacing Kim France?
I heard a lot from the readers, and they love the magazine. That’s the most important thing. I’ve been talking to a lot of readers; I’ve been talking to a lot of women. They love this magazine. So it’s my job just to bring my take to it. It’s not about scrapping it. It’s a really great magazine and women really do love it. And I’m going to bring my angle.

What advice do you have for someone who wants to get into fashion writing for print?
Start a blog and put it on as many platforms as you can. If you’re really young and you can do it, get an internship. Do everything you can do. Just do it; just get in there and start. Now anybody can be a publisher, so just start publishing your work. I know everyone’s heard that. But once you start — you’re on foursquare and you’re on Twitter and Facebook and Tumblr and you’re making sure you’re hitting multiplatforms — and you know to work Google Analytics, you can grow your readership. YOU can grow your readership; you don’t have to depend on someone else just to distribute your content. You’re your own distributor. You just have to learn to work the many platforms that are available. And learn how to use Google Analytics because that will tell you how you’re doing and how you can grow it, what your readers are doing and what they want more of.

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Amanda Ernst is a freelance writer living in New York. She also manages business development and social media marketing for B5 media, the publisher of three women’s lifestyle sites.