The 1 Piece Of Advice My Friend Gave Me Before Interviewing Kevin O’Leary

I was getting ready to sit down with Kevin O’Leary for an interview.

We were in one of the back rooms, behind the set of Shark Tank. I grabbed a water bottle from the long table filled with fruits and small sandwiches and trays of candies.

Over and over again, a piece of advice from one of my closest friends, Dr. Matthew Jones, played in my head.

Kevin entered the room, looked around like he hadn’t had a break in hours, and said, “Where do you want me to sit?”

It was straight down to business.

We got him set up with a lavaliere mic, got our two cameras in position, and I took a seat opposite of him.

He looked me dead in the eyes and said, “Go.”

I was incredibly nervous.

The morning prior, I had woken up to an email that said, “Kevin will be filming tomorrow at Sony Studios. He has a 20 minute gap for lunch. Can you swing it?”

In less than a day, my business partner Drew Reggie and I rented camera equipment, plotted out the interview, and showed up to Sony Studios hoping for the best.

After almost a year of following up with a handful of different contacts, and with 24 hours notice, I had finally gotten the OK to interview one of my business idols in person.

The moment the cameras started rolling and our interview began, the same advice played in my head.

“A genuine connection will go a long way.”

I reminded myself that there was a time when he was just like me — young, hungry to learn, and willing to leap outside the comfort zone if it meant growing and learning in the process.

Instead of sitting there feeling like I had something to prove, I tried to just be me.

And the more I approached our conversation from a genuine place, person to person, no need to impress, the easier it flowed. For several moments throughout the interview, it felt like we were just trading stories.

At the twenty minute mark, he stopped and said, “Looks like I’m getting called back to set. It was great chatting.”

We shook hands, and I said, “I really appreciate you taking the time.”

It definitely wasn’t my best performance, but I walked away from that experience having learned a very valuable lesson.

A genuine connection goes a long way.

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