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Shawn Meaike

👤 Person
623 total appearances

Appearances Over Time

Podcast Appearances

Escaping the Drift with John Gafford
From Adversity to Triumph: Shawn Meaike’s Journey to Building a Billion-Dollar Insurance Empire

So we did it. They agreed to do it. Not everybody's home, but after about six hours, he's like, okay, what do you do? And I said, well, it's easy. All there's 50 guys like me around here. I'm one of the biggest, but there's 50 of us. There's a few individual people that have a property owner. 85 to 90% of the home, the landlords, the property owners don't even live in Connecticut.

Escaping the Drift with John Gafford
From Adversity to Triumph: Shawn Meaike’s Journey to Building a Billion-Dollar Insurance Empire

They've retired and moved to Florida. At the time I was in my 20s and 30s, they're 70 or 80. So I would say, hey, John, listen, let me ask you something, bro, before I rent this to you. What do you think the chances are that you're going to get in a place where you can't pay your rent? And I mean ever, John. You'll say probably never. You're awesome. You're never going to have a problem. Cool.

Escaping the Drift with John Gafford
From Adversity to Triumph: Shawn Meaike’s Journey to Building a Billion-Dollar Insurance Empire

They've retired and moved to Florida. At the time I was in my 20s and 30s, they're 70 or 80. So I would say, hey, John, listen, let me ask you something, bro, before I rent this to you. What do you think the chances are that you're going to get in a place where you can't pay your rent? And I mean ever, John. You'll say probably never. You're awesome. You're never going to have a problem. Cool.

Escaping the Drift with John Gafford
From Adversity to Triumph: Shawn Meaike’s Journey to Building a Billion-Dollar Insurance Empire

They've retired and moved to Florida. At the time I was in my 20s and 30s, they're 70 or 80. So I would say, hey, John, listen, let me ask you something, bro, before I rent this to you. What do you think the chances are that you're going to get in a place where you can't pay your rent? And I mean ever, John. You'll say probably never. You're awesome. You're never going to have a problem. Cool.

Escaping the Drift with John Gafford
From Adversity to Triumph: Shawn Meaike’s Journey to Building a Billion-Dollar Insurance Empire

I go, John, let me explain how this works. Me and my property manager, we live within 10 minutes. So if you don't pay rent, we're going to be so fucking annoying. I mean, like here all the time, knocking on the door. We might walk in because we might think you're unsafe. We might call 911 and think you're unsafe. We might be parked outside. We're going to text. Dude, we're just a pain in the ass.

Escaping the Drift with John Gafford
From Adversity to Triumph: Shawn Meaike’s Journey to Building a Billion-Dollar Insurance Empire

I go, John, let me explain how this works. Me and my property manager, we live within 10 minutes. So if you don't pay rent, we're going to be so fucking annoying. I mean, like here all the time, knocking on the door. We might walk in because we might think you're unsafe. We might call 911 and think you're unsafe. We might be parked outside. We're going to text. Dude, we're just a pain in the ass.

Escaping the Drift with John Gafford
From Adversity to Triumph: Shawn Meaike’s Journey to Building a Billion-Dollar Insurance Empire

I go, John, let me explain how this works. Me and my property manager, we live within 10 minutes. So if you don't pay rent, we're going to be so fucking annoying. I mean, like here all the time, knocking on the door. We might walk in because we might think you're unsafe. We might call 911 and think you're unsafe. We might be parked outside. We're going to text. Dude, we're just a pain in the ass.

Escaping the Drift with John Gafford
From Adversity to Triumph: Shawn Meaike’s Journey to Building a Billion-Dollar Insurance Empire

The rest of these guys, they won't even know. You'll be four months into not paying rent before they send you a fucking letter. Me, I know the family relations people. I know the people at the courthouse here. I know everybody down there. Dude, path of least resistance. If you think it's going to be a problem ever, dude, just rent from them. They won't even screen you out.

Escaping the Drift with John Gafford
From Adversity to Triumph: Shawn Meaike’s Journey to Building a Billion-Dollar Insurance Empire

The rest of these guys, they won't even know. You'll be four months into not paying rent before they send you a fucking letter. Me, I know the family relations people. I know the people at the courthouse here. I know everybody down there. Dude, path of least resistance. If you think it's going to be a problem ever, dude, just rent from them. They won't even screen you out.

Escaping the Drift with John Gafford
From Adversity to Triumph: Shawn Meaike’s Journey to Building a Billion-Dollar Insurance Empire

The rest of these guys, they won't even know. You'll be four months into not paying rent before they send you a fucking letter. Me, I know the family relations people. I know the people at the courthouse here. I know everybody down there. Dude, path of least resistance. If you think it's going to be a problem ever, dude, just rent from them. They won't even screen you out.

Escaping the Drift with John Gafford
From Adversity to Triumph: Shawn Meaike’s Journey to Building a Billion-Dollar Insurance Empire

They'll never even meet you. And people are like, that doesn't work. Dude, it worked all the time. If I wasn't going to pay... And he was like, I don't give a shit at all. And you were like, you do. I'm like, I'd go with him. Why would I not? That doesn't make any kind of sense. So we really worked really, really hard. You understand, my first job at 16.

Escaping the Drift with John Gafford
From Adversity to Triumph: Shawn Meaike’s Journey to Building a Billion-Dollar Insurance Empire

They'll never even meet you. And people are like, that doesn't work. Dude, it worked all the time. If I wasn't going to pay... And he was like, I don't give a shit at all. And you were like, you do. I'm like, I'd go with him. Why would I not? That doesn't make any kind of sense. So we really worked really, really hard. You understand, my first job at 16.

Escaping the Drift with John Gafford
From Adversity to Triumph: Shawn Meaike’s Journey to Building a Billion-Dollar Insurance Empire

They'll never even meet you. And people are like, that doesn't work. Dude, it worked all the time. If I wasn't going to pay... And he was like, I don't give a shit at all. And you were like, you do. I'm like, I'd go with him. Why would I not? That doesn't make any kind of sense. So we really worked really, really hard. You understand, my first job at 16.

Escaping the Drift with John Gafford
From Adversity to Triumph: Shawn Meaike’s Journey to Building a Billion-Dollar Insurance Empire

And if you know that you're going to not pay your rent, you're not going to pick me. Yeah. Because I'm going to annoy you. Yeah. You're going to pick the other dude. And guys would actually call me. This guy named Eddie, he would call me. He'd be like, did you interview so-and-so? I'm like, did you rent to him? Yeah. I would give him their number sometime. I'd be like, dude, this guy is real.

Escaping the Drift with John Gafford
From Adversity to Triumph: Shawn Meaike’s Journey to Building a Billion-Dollar Insurance Empire

And if you know that you're going to not pay your rent, you're not going to pick me. Yeah. Because I'm going to annoy you. Yeah. You're going to pick the other dude. And guys would actually call me. This guy named Eddie, he would call me. He'd be like, did you interview so-and-so? I'm like, did you rent to him? Yeah. I would give him their number sometime. I'd be like, dude, this guy is real.

Escaping the Drift with John Gafford
From Adversity to Triumph: Shawn Meaike’s Journey to Building a Billion-Dollar Insurance Empire

And if you know that you're going to not pay your rent, you're not going to pick me. Yeah. Because I'm going to annoy you. Yeah. You're going to pick the other dude. And guys would actually call me. This guy named Eddie, he would call me. He'd be like, did you interview so-and-so? I'm like, did you rent to him? Yeah. I would give him their number sometime. I'd be like, dude, this guy is real.

Escaping the Drift with John Gafford
From Adversity to Triumph: Shawn Meaike’s Journey to Building a Billion-Dollar Insurance Empire

He'll like you. Call this guy. Call this guy. I'm just telling you, Basin, because I think that the thing for me was my first job at 16, this guy just passed away. Outstanding guy. He was a big mentor of mine, professional baseball player, Yankees, Rangers, Red Sox, and a huge real estate guy in Connecticut. You're talking about in the early 90s. My first job.

Escaping the Drift with John Gafford
From Adversity to Triumph: Shawn Meaike’s Journey to Building a Billion-Dollar Insurance Empire

He'll like you. Call this guy. Call this guy. I'm just telling you, Basin, because I think that the thing for me was my first job at 16, this guy just passed away. Outstanding guy. He was a big mentor of mine, professional baseball player, Yankees, Rangers, Red Sox, and a huge real estate guy in Connecticut. You're talking about in the early 90s. My first job.

Escaping the Drift with John Gafford
From Adversity to Triumph: Shawn Meaike’s Journey to Building a Billion-Dollar Insurance Empire

He'll like you. Call this guy. Call this guy. I'm just telling you, Basin, because I think that the thing for me was my first job at 16, this guy just passed away. Outstanding guy. He was a big mentor of mine, professional baseball player, Yankees, Rangers, Red Sox, and a huge real estate guy in Connecticut. You're talking about in the early 90s. My first job.

Escaping the Drift with John Gafford
From Adversity to Triumph: Shawn Meaike’s Journey to Building a Billion-Dollar Insurance Empire

like outside of McDonald's grocery store job was going to the job site, meeting these guys, taking a truckload of four by fours, going to people's apartments, screwing the four by fours, two of them to their door. If they were delinquent on rent, I mean, I, you can't do it. Shouldn't do it. It's all awful. But, but think about this. I never forget going like, what are we doing?