Growing up, one of my favorite shows to watch was Larry King Live on CNN. He had amazing guests and always seem to ask the kinds of questions that I would like to ask if I was the host.
Because it was live, there was a kinetic energy. You never knew what was going to happen.
Also, Larry never asked a question that made his guests feel uncomfortable. This meant that both the guests and the audience could relax and enjoy the conversation.
While I am someone who likes to set goals, never in a million years did I dream that I would ever be interviewed by Larry King.
Here’s how it happened. My friend Dr. Mark Goulston became a mentor of mine after hearing me as a storytelling keynote speaker in Los Angeles to a group of media, entertainment, and technology entrepreneurs.
When he told me he had breakfast every morning with Larry King and a group of Larry’s friends, I was impressed and wanted to know more. One of the other breakfast buddies was Cal Fussman.
Mark suggested that Cal and I get to know each other because we both worked in the magazine business. Cal was a esteemed journalist for Esquire magazine for many years, interviewing famous people such as Gorbachev. I, on the other hand, sold advertising for magazines.
In the magazine heyday, advertising salespeople were “not allowed” to talk to journalists. There was a “Church and State” separation. When Cal and I were having lunch, we joked about the two of us breaking down that wall like Gorbachev and Reagan.
As my friendship with Cal evolved, I showed him how storytelling could become a sales tool for him to sell himself as a speaker. He invited me to join him as he co-hosted a TV show called Breakfast with Larry… with none other than Larry King!
You can imagine my surprise and delight. One of the mantras I say to myself is “wonderful things are happening for me from sources expected and unexpected.” This was certainly an example of that.
On the day of the interview, I was told to arrive at the deli in Beverly Hills where we would literally have breakfast with Larry King. We would then get into his car and be taken to Larry’s TV studio where we would do the interview.
As part of my preparation, I read that Larry King did not like small talk, so I wanted to make sure I knew as much about Larry and his career as possible. Vanity Fair did an amazing excerpt of his biography about how he got his big break interviewing Frank Sinatra when he was a radio host in Miami. Apparently, Jackie Gleason had been a guest on Larry King’s radio show and asked Larry this wonderful question: “What’s impossible in your business?”
Larry replied that it was impossible to interview Frank Sinatra because his son had recently been kidnapped. The media was implying it was due to his connections to the mob, which made Sinatra furious, so he refused to do any interviews. Gleason said he had to fill in for Sinatra as a favor once when Sinatra had laryngitis, and Sinatra and said, “I owe you one.” Jackie decided to call in his favor with Sinatra and ask him to have Larry King interview him.
Ironically, Sinatra was so comfortable with Larry he brought up the fact that his son had been kidnapped and even invited Larry to bring a date to hear him sing the next night at a private club.
Larry was very excited because he knew whoever he brought, she would be very impressed.
They had a great seat and Sinatra even acknowledged the interview from the stage and predicted that Larry King would be famous someday.
On the way home with his date, she asked Larry to stop and buy some coffee for them to have the next morning. Unfortunately, Larry did not have any cash and this was before the days of a lot of credit cards and ATMs. He knew if he said he didn’t have cash, the whole evening mood would be ruined.
So he walked in the store and came out a few minutes later. She said, “Where’s the coffee?” He responded, “They couldn’t change a $100 bill.”
When I read that story, I laughed out loud. I knew I was going to bring that up in my conversation with Larry.
On the way from breakfast in the car with Larry and Cal, I asked Larry about that story. He smiled and said, “Yes. That was a great night.”
Then when we were on camera, Larry asked me what made a good story. I knew that he would be comfortable talking about that story so I said, “Let’s go through your story about your big break and show why it is a great story.”
The exposition is that you’re in Miami as an up-and-coming DJ on radio, and you got your big break by Jackie Gleason calling in a big favor.
The problem was Sinatra wasn’t going to do any interviews.
The solution is you got him to do an interview, and he then invited you and a date to hear him sing. But the problems escalated again when you didn’t have money to even get coffee after you showed your date a great time.
The resolution of that story is what you said to her when you came out of the store. They couldn’t break $100 bill. That’s what makes the story so memorable. What makes all stories wonderful is a powerful resolution.
From that point on the interview, just went better and better and Larry could not have been nicer or warmer.
Let’s all learn to stay open to wonderful things happening to us, even if we’re not dreaming about them as a possibility.
Remember the key to having meaningful conversations with people is to prepare so that you can talk about something that’s meaningful to them.