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.

Understand that online marketing is both science and art. Here are some specific points of interest for all businesses, whether you are high e-commerce or a brick-and-mortar that needs online presence:

Start Conversations
What type of email is opened the most – newsletters, promotions, ads? None of the above. Emails with the highest open rate are transactional. Confirming sign-ups, receipts for purchase and delivering passwords are considered transactional. While you have these eyeballs at the ready, why not promote something and get them engaged further?

No Dumping
Once you start a conversation, keep it going. If you are going to send people to your website from a direct mail piece or advertising, make sure they find themselves on a landing page or can easily continue the conversation you started. Don’t make them work for something that should be instantly gratifying. If you want to capture their information before they can get what you promised, get their name and email. Later on you can build more information on them.

Connect With Opt-ins Only
The more you send out emails that get hard-bounced, get put on black lists or avoid protocol (such as neglecting to put your company name in the “from” line or not using a dedicated URL in a campaign delivered by a sales management platform), the more you will be seen as less legit by search engines.

Some great resources for email and web marketing include:

Tamara Gielen – I met Tamara at a conference in Miami - she has great info on the latest in email and marketing trends on her blog, Be Relevant! at: http://www.b2bemailmarketing.com

TheEmailWars.com – eROI is a company that is focused on email marketing and this blog is the better of their four. It showcases best and worst examples of email campaigns and creatives.

Jakob Nielsen – the king of online usability, has a great article on “writing articles not blogs”: http://www.useit.com/alertbox/articles-not-blogs.html

Bazaarblog – Produced by a marketing firm, this blog has some great info on word-of-mouth strategies, ecommerce strategies and marketing.

Borough Clock Fund II reached its $200,000 goal!

The July 29th Games on the Green event, to benefit restoration of the Stonington Borough Clock and Tower in Stonington, Conn., was a huge success for both fundraising and fun raising.

It was really exciting to be a part of an event that brought together volunteer efforts from the community at large, from residents and local restaurants to businesses outside the immediate community like Enfield, Conn. cabinet maker Rome Polaski, Big Y, Jonathan Edwards Winery and the Lebanon Lions Club.

The day’s highlights included cool kids’ games that were the envy of all the adults like potato sack races and tug of war, a nailbiting croquet tournament, tons of belly-filling treats, fabulous raffle prizes such as Front of the Line passes for Borough hotspots and an olde tyme seranade by local barbershop troupe, the SeaNotes. We had expected about 15 SeaNotes and 24 showed up for the event! The media didn’t disappoint as well and included The New London Day, the Westerly Sun and Fox 61 News at 10:00. We were only on Fox for a millisecond which is a bit disappointing considering co-chair Kate Love gave a great interview but, hey, I’m just happy I was able to entice them enough to show up!

The biggest hiccups of the day included rocks in the bubble machine and a round of croquet that ran quite a bit longer than the players would have liked (next year we’ll do lightening rounds). Other than that, the whole event was just as the event committee had hoped - a fun, relaxing Sunday afternoon filled with friendly competition and a step back in time to the casual gatherings that draws a community together at the town green.

Heading into the event, the committee had raised $197,000. During our event, we had a crowd of both day long participants and passersby that reached about 150 people, but those folks helped raise over $2,000! One of the biggest compliments we received was from an anonymous donor who was unable to stay for the festivities but offered to provide the remaining funds needed to help us reach our goal. This donor hoped that by closing the gap on the final monies required through this event that it would encourage more celebrations of this kind in the future. It worked. We’re already gearing up for next year’s event.

Thank you anonymous donor and all the folks that helped us celebrate on Sunday. Your support has saved a treasured Connecticut landmark and has sparked a tradition - old-fashioned fun that breathes new life into community spirit!