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The art of interviewing

October 17, 2013 @ 9:43am

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Back in 2001, I was working for my friend Jason Calacanis at his company Rising Tide Studios as CTO. The dotcom crash was hitting our magazine and conferences business pretty hard. It was tough to put out a monthly magazine with two-page spreads showing hot NYC startups when they were rapidly vanishing. With them gone, who would advertise in your magazine and sponsor your events — or even show up at your events?

So Jason switched gears. (That's what we called "pivoting" back in the day.) He stopped doing the thousand attendee $1,000 ticket events and he did more focused little summits with 100 CEOs discussing trends and markets that were still being invested in like security, healthcare and wireless. His 100-CEO events were the inspiration for my Meet The Makers events in 2002, partly because I liked the model of qualified free attendees drawing paying sponsors and partly because of my ego. I felt like I was at least as smart as Jason and if he could interview a bunch of people on stage for a living, then so could I.

But my events would feature the people actually doing the work, CTOs, not the people taking the credit for all the hard work, CEOs. Again, in my head it was a direct response to Jason's events. I even partnered with Jason on the events, which was a smart move. If I'd done them on my own, I would have surely lost money. Splitting the revenue in half with Jason, I actually made money in a brutal year where major conference businesses were dropping like flies.

I did three Meet The Makers events in NYC and SF in 2002 and in 2003 after my son was born I did nearly a dozen more online interviews. I love interviewing people and I appreciate great interviewers like Alec Baldwin and Howard Stern.

Recently, when I was figuring out what to do after Ceros, I considered starting Meet The Makers up again. I felt like I could start with online interviews this time and work my way up to live events. It seemed like a good way to help move Ceros forward from the outside, again avoiding Shared Command.

When I mentioned this to a bunch of people who had seen MTM, the first reaction from all of them was that they enjoyed my interviews, that I was a good interviewer. That felt great.

But I have to say that I no longer have that same conceit that I'm a better interviewer than Jason. After seeing him on stage at the LAUNCH Festival in March and at LAUNCH Mobile in September, he has clearly taken his interviewing game to the next level. He doesn't seem to have a list of questions in hand. He listens to answers and asks smart follow up questions. And he knows when to end an interview — which is crucial.

I guess doing nearly 400 startup interview shows is great practice.

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