Kevin O'Leary

speaker

672 appearances 1 recordings 1 series first heard Jul 2026 last heard 30 Jul

Kevin O'Leary’s voice in public audio — every appearance, attributed to the second.

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recordings per month · last 12 months

Recordings per month over the last 12 months — 1 in all, peaking in Jul 2026 with 1.

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He was difficult.

He was ornery.

He had a woman working beside him back then named Heidi Rosen who would smooth things out afterwards, you know, and...

We would have contentious meetings in the old headquarters, brutal.

And he would just, you know, be brutal.

And some of my staff would be crying when it was over.

And then Heidi would call me on the way back to SFO and say, look, we're going to pay you the $12 million for the update or whatever it is.

But she wouldn't even apologize for Steve.

We were past that.

I didn't need to.

There was no text back then.

He would email me at 3 in the morning Boston time and expect an answer within five minutes.

And I would give it to him because he was such a huge client.

I'd wake up for that.

That was him being on signal.

And so I've kind of adopted that too.

You've got to understand you will get stuff coming at you all day that doesn't matter.

And because you push it aside, people get pissed.

I know.

They feel they're not important.

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