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The Short-Term Shop

Identify Your Goals with Steve Rozenberg

Identify Your Goals with Steve Rozenberg

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Identify Your Goals with Steve Rozenberg

Steve Rosenberg shares his journey from being an airline pilot to a real estate investor after the 9/11 events that dramatically changed his life. He emphasizes how he had to start from scratch, learning real estate through books and personal trial and error, and how he developed strong negotiation and communication skills that helped him succeed.

Avery: Hey everybody, welcome back to the show! Today we have Steve Rosenberg on. You’ve probably heard him in a number of different places; he’s on Bigger Pockets, sometimes he’s got his own podcast, the High Stakes Podcast. He’s a really cool guy who does a lot of different things, and I’m really excited to introduce him to you. How’s it going, Steve?

Steve: It’s going good! Good to see you again.

Avery: Good to see you too! It’s been about two years since I’ve seen you in person, right?

Steve: Yeah, it’s been a minute!

Avery: So, Steve, why don’t you introduce yourself to our audience and tell us a little bit about yourself?

Steve: My name’s Steve Rosenberg. I’ve been involved in real estate for about 20 years. I hate to say that because it kind of starts to date myself, but in all honesty, I never wanted to be in real estate. I never thought this would be my plan or my goal. Maybe like a lot of people listening, it was a secondary or tertiary goal of what they’re doing. For me, I just wanted to have a regular job and career, and that job for me was being an airline pilot.

Something happened in history that changed the direction of my life. It changed the history of everything, and that was 9/11. 9/11 was obviously a pivotal point in history. For me, two days after 9/11 is when my world changed because that’s when I got a furlough notice from the safe and secure airline job that I always thought I’d have. I was 25 years old and the second-youngest person working for this airline.

I was going to retire number two. Everyone’s like, “You’re done, you’ve got it, you’re good.” And I’m thinking, “Yeah, I’m good.” But then, about three years later or so, 9/11 hit. I got a furlough notice, and they said, “You know what, Steve, that safe and secure job you thought you had was never safe and never secure.” I was out on the street with 50,000 other pilots.

Oh my goodness, so to say that you get punched in the face is an understatement. 9/11 had just happened, and now I’m basically going to be out of a job. The only skill set I had was flying an airplane, which suddenly wasn’t that useful anymore.

Avery: So you saw this trend happening, and it was like, “Prepare for the worst,” in a span of 48 hours.

Steve: Yeah, exactly! I went from the best job in the world on Friday to wondering, “What am I going to do with my life?” on Monday. My whole life seemed useless now, and it was really humbling.

I started looking at what successful people did. This was back in 2001, and there was no YouTube or Facebook, so I had to go to this big building with books—called the library! I got a library card, started reading books, and I read a book a week on real estate because it seemed like everyone that was wealthy somehow tied back to real estate. I learned how to flip, wholesale, and do rentals.

I started taking action, and I got my butt kicked a lot. I got ripped off, lied to, cheated, but I kept getting back up because I didn’t have a choice. There was no social media or people to turn to back then; I had to figure it out myself.

I lost money, but I eventually started winning. I learned from my mistakes, and I realized the best skill I had was learning how to negotiate and communicate. That’s when things really started to turn around for me. I got very focused and dialed in on what I needed to do.

Avery Carl

Avery Carl

Avery Carl was named one of Wall Street Journal’s Top 100 and Newsweek’s Top 500 agents in 2020. She and her team at The Short Term Shop focus exclusively on Vacation Rental and Short Term Rental Clients, having closed well over 1 billion dollars in real estate sales. Avery has sold over $300 million in Short Term/Vacation Rentals since 2017. An investor herself, with a portfolio of over 100 Doors, Avery specializes in connecting investors with short term rentals with the highest ROI potential, and then training them to manage their short term rental from their smart phone from anywhere in the world.

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