I listen to Howard Stern. As a successful 30-something-something entrepreneurial female, I’m not the typical Stern target fan (although there are many white collar white chicks out there who are big fans). I have been fascinated by Howard over many milestones. When he got drunk on the air and called up and berated then-wife Alison (or at least that’s how I remembered it as a kid, before my mom shut the radio off), when Howard left WCCC in Hartford, when Howard went national and I got to hear him again in CT, when I finally got to see the show’s ridiculously mutly crew on ET and, finally, now at Sirius.

Each morning when I can catch the show in my car, I flip around from NPR to BBC to music to whatever but I always go back to Howard. I could never really explain why I liked Howard, except for basic entertainment value, until today.

Today, Howard proved to me why he is the King of All Media. His guests were the Counting Crows. Lead Singer Adam Duritz did most of the Crows’ interview and, when he first started talking, I thought the whole interview was going to be one big headache. The guy couldn’t answer a straight question. He was dressed in a bunny suit and was more intent on giving Howard flip answers and jokey comments that went nowhere. I was happy to only visualize his pink ridiculousness versus really seeing it. I thought, “Give me a break Adam. Don’t try so hard. Just shut up and sing.”

And then, it changed. Howard isn’t a practical, tidy interviewer like Ed Bradley or Terry Gross but he is incredibly astute to chemistry. Adam wasn’t giving Howard what he wanted. He was dodging, skimming and sliding. I was expecting Howard to give up at any minute. Well, I was hoping he would give up. Nope. Howard persevered and I suddenly started paying more attention to Howard’s strategy instead of Adam.

I think there’s a lot we can learn from Howard when it comes to having an intriguing conversation. How many times have you talked with a client or colleague and walked away thinking it was a total waste of time? Or, maybe it felt like you got the basics covered but something was missing. It was good but not great. Howard knows how to get great - it’s his thing.

I never thought I’d say this but here’s how I will apply Howard’s interview tactics in my biz:

1) Get out of the ditch. As soon as Howard could tell that Adam was going to be a tricky interview, he started treating the discussion like a 2-wheel drive sedan stuck in a ditch. He gave it just enough gas to inch it forward but not too much to dig a bigger ditch. There are delicate ways to get information out of people. People want to tell you things - good, bad and ugly. It’s all in how you shimmy the rear end.

2) Move on. If your interviewee or counterpart is stubborn, ask them something else. When Howard could’ve gotten frustrated with Adam’s avoidance of questions, he threw a different zinger at him. The result was Howard slowly picking at Adam, wearing him down from all angles until Adam finally started having a real conversation. This is because Adam finally caught on that he was beginning to sound like a jackass. But, and here is the genius of Howard, it wasn’t Howard making him look like a jackass. Adam was doing the work all himself. To correct it, he intuitively began to open up to Howard. When he did, he showed his intelligence and genuine nature. Suddenly, he was connecting with Howard which meant he was now connecting with Howard’s fans.

3) Start with the finish line. Howard’s goal with interviewing Adam and the Counting Crows (well, mostly Adam) was to entertain his fans. Nothing new, of course. That’s his goal every day. But, the important thing to remember is that he never lost sight of the goal throughout the interview. The session transformed from bunny-suited rock guy spouting glib weirdness to a bunch of guys hanging out. The whole interview actually flipped: it went from stiff and forced to an unexpected good time. You can’t structure that. Howard worked hard at making sure the interview ended in its best form and he did it by reading the interactions of his interviewee, not by just jamming questions down his throat and hoping for good responses.

By the time the Crows started to play, I wanted them to hang in the studio all day. And then it just got better. They played two songs - Round Here and a new one, Washington Square. Then, Howard asked the band if they ever just messed around in the studio and played whatever when they hung out. Adam mentioned that they did a good version of the Grateful Dead’s “A Friend of the Devil.” So, they played it. I, like Howard, can’t stand the Grateful Dead but we both had to give them props for an awesome version. The conversation continued and, before I knew it, they were playing Springsteen’s Thunder Road. Where else could you get this out of a band? It just doesn’t exist.

I feel like Howard is at his best right now because he’s on Sirius and he doesn’t even realize why. I’ll tell him: he has brought community to entertainment. Everything that’s burgeoning in the realm of techie community, from sharing vids to me writing this post for anyone to stumble on, wants what Howard delivers. Once again, Howard’s ahead. Love or hate the King of All Media, we can all learn from him.

As a side note, if big business continues to block the Sirius-XM merger, they are not just sticking it to Howard and satellite radio. They are sticking it to all of us - at least for now. Communities that build online and in new formats like satellite radio are inevitable. The big pockets can’t hold it back forever.

Predicting what 2008 will bring is tricky business. It’s an election year, housing is moving on from sellers-market denial, credit card debt continues to eat away at our economic stability, the U.S. dollar has seen better days, old media continues to fight the once-good fight while new media prepares for all-out infiltration and conglomerate air time is continually consumed by the Writer’s Guild strike and Britney Smears instead of our troops.

Armageddon? Not yet. As far as I can tell, turmoil breeds panic for the timid and intrigue for everyone else. The business climate, depending on the business, is at once volatile and filled with opportunity. I see the upcoming two years as less of an end to a decade than a precursor to the incredible shifts that will take place beginning in 2010. Virtual living and working will cause person-to-person business to make room for better online practices and philosophies. To be truly successful in the Web 2.whatever, businesses must synergize online and offline activities. Your business’ relationships, revenue and mojo depend on it. Enough about the decade, let’s just focus on 2008 for now.

Below are WallFly’s top three predictions for the upcoming year. I have to admit they are a mix of prediction and hope. Maybe I should have called them “Business-Fulfilling Prophecies” instead?

Recession Schmession

Smart companies will improve relationships, not business plans.

I’m not suggesting you avoid streamlining. We’re all making measured decisions with our cash flow. Just last week I considered not sending out a business mailer for the holiday season. Instead I opted to spend less money at Panera and wait until the new year to hit Staples.

Move your numbers around all you want but if you’re not taking time out to do the following, you are losing ground with clients: a) connecting with your clients on a regular basis (phone, mail, email or events) to increase opportunity for more interaction b) learning when, why and how your current clients interact with you, and applying that knowledge to improving your value and c) feeding your positioning with a menu of competitive activity, impending growth and your customer’s changing climate.

We all know that getting a client takes double the effort versus convincing a happy client to stay, so why do companies continue to neglect clients in the off-season of interaction? Think about your best personal relationships and what makes them tick. Making someone happy in a relationship 90% of the time requires improving their life every day (i.e., taking out the garbage) versus buying an expensive gift one day out of the year (i.e., buying an iPhone). Next time you consider dumping all of your marketing dollars into a big trade show, think about the low-budget things you can do to reach out to clients throughout the year: start a monthly newsletter, make quality control phone calls, talk about how other clients benefit from you, make in-person annual visits or even send out a short quarterly email that shares info on upcoming developments.

Ecomm Grows Up

Utility will emerge from 80 gazillion social media apps.

I’ve seen some pretty useless Facebook applications - from starting a virtual snowball fight to getting hugged by a zombie. How do these strides in web development improve your business? They won’t. But they will change the way users interact with the web and that’s what you need notice. Once users start expecting things from the online world, they want it from everyone - a streamlined user experience, content that takes into account context and a site that understands the concept of easy.

The massive amount of activity taking place among developers for Facebook and now Google’s universal app platform will both increase the size of our kids’ behinds as they play less soccer (or play more virtual soccer) and generate technologies that users will want to see everywhere. If you have a website, start paying attention to the activities happening online. You don’t have to apply them all but you have to understand how it will affect your clients. I’ve advised some clients to skip blogging because it didn’t make sense for them. It’s not about jumping on the latest, new technology - it’s about understanding how all new technology is driving the way we do business.

Marketing Gets Stuck

New media will drive marketing. The stories that stick, win.

I was wondering when some smart marketing guy would take Chris Anderson’s Long Tail and extend it by applying it to branding. The smart marketing guy is Mohammed Iqbal and the essay is The Elongating Tail of Brand Communication, as found on ChangeThis.

One-hit wonders are not only increasingly rare in this climate of targeted success, aiming for them is the same as denying the tastes of various music fans. We are a culture of choice and highly personal demand. One size does not fit all and this philosophy applies to both your products or service and your brand position.

I recently discovered this in my research for finding a market for a Connecticut coworking space, Group88, that I will help manage in 2008. Some of the area professionals liked the idea of getting out of their home-based office to meet with other folks while others had no need for networking at all (I think there’s always a need for networking but I’m partial to the practice). You can’t be all things to all people so don’t even try. You can, however, choose the primary values of your positioning that appeals to your variety of customers. Using new media channels to test an idea and then kill it or expand it will yield higher results than picking one thing and crossing your fingers that it will stick. Don’t egg your basket - add crates and buckets and other things to put all your eggs into.

Back in “the day” when I was young-er and living in NYC, I was lucky enough to be a part of a group of friends that became like family to me. We were all in our mid to late 20s, making our way together through first career mishaps, crazy bosses, jackass men and a city that wouldn’t let us quit. We’ve all since split and moved to California, Ireland, New Jersey, Staten Island and Connecticut but there was one night in Port Chester, NY that we’ll never forget.

Somehow we fell into partying with this group of guys who were relentless at promoting themselves. This was the early days of mass email and these guys latched on - building lists of people that they could email write-ups about their weekend adventures and announcements about upcoming gatherings. At the time, retro ’70s was huge in NYC so these guys decided to have a Boogie Nights party. For me and my girls, it was like a message from the glittery gods of platform shoes and feathered hair.

We spent HOURS. We shopped out our costumes at Salvation Armies and cheap discount stores, we bought loud make-up and talked endlessly about what look each of us could carry off. The highlight of our make-ready was studying the blue eyeshadow of William H. Macy’s wife in Boogie Nights as she got jiggy with a guy who was not William H. Macy. We actually paused the scene so we could replicate the look. When the pause ended, we rewinded and paused again.

When felt boogied up enough, we jumped on a train out of the city to Port Chester where we anxiously talked about what everyone else would be dressed as or who would be there and how awesome the night ahead was sure to be. It seemed like days since we started getting ready. The time had come to shake it down.

Arriving at the train station, the host picked us up and provided many compliments on our presentation and effort. We didn’t seem to notice that he was sans Boogie Nights apparel. We were dying to jump right into the festivities. Walking into the house, I was pretty sure I could feel my wispy feathered do go limp as we entered into nothing. No balloons. No streamers. No people. Well, there were some people but they were all huddled in a side room watching a football game. Not one of them in polyester or blue eyeshadow.

They didn’t stay in that room long. We had arrived and we were ready to party. It took a while but we got that group off their butts and made a heck of a boogie out of that night. We have the pictures to prove it.

I think the best marketers and business strategists can take a page out of the Boogie Nights’ book. These days, so much effort is spent mapping and measuring and mulling over promotional strategies that will garner X, Y, Z penetration and deliver A, B, C results. We spend more time trying to control the outcome of a product or company than actively living in the goodtimes and pitfalls that happen every day. When you live in the moment, you are agile and aware. You can recognize opportunities that you may have missed by looking at tomorrow.

If my pals and I knew that we’d show up to a blah party that night in Port Chester, we would’ve done something else. But we didn’t. Instead we spent too much money on ourselves, too much paste on our face and too much time giving each other belly laughs. The result wasn’t showing up to a disappointing party. We were the party and, today, friends for life.