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The Short Term Show with Derek Tellier
Derek Tellier shares his journey from a 20-year corporate career in the Harley-Davidson industry to achieving financial freedom through real estate investing. After a major life shift in 2016, he took the leap into real estate, starting with refinancing his home and moving to investment properties. Derek now owns seven properties, four of which are short-term rentals.
Avery: Hey guys, I would like to welcome Derek Tellier to the show. Derek is retired from his corporate job and shifted into short-term rental investing. He is here to tell us his story today. Derek, how are you?
Derek: I’m wonderful, Avery. Thank you so much for having me on. I’m excited to be here.
Avery: Very excited to have you! So first off, can you tell us just a little bit about yourself, your work history before you got into real estate investing, and how many doors you have now? How you’ve gotten there?
Derek: Sure. Well, to start kind of towards the beginning, I spent over 20 years working in a—I don’t like to use the word ‘corporate’ because I was kind of in the middle of things—but I worked in the Harley-Davidson industry. I started out as a technician working on motorcycles and worked my way up into management and then eventually got to a position where I was actually a service director over service departments for a small group of dealerships.
But it was a W2 job, and I was just in that mindset—you go to school, you get a job, you build your way up, you make some decent money, and then you retire when you’re 65. It was probably around 2016 that I took a whole life shift.
It started with my health—my diet and exercise—and really got me to clear my mind. Then I got introduced to real estate, to BiggerPockets, and all the usual things like ‘Rich Dad Poor Dad.’ It was like, “Wow, what have I been doing?” But I still had a hard time wrapping my head around it. It was so different from anything I had been taught.
You know, they don’t teach you this in school. Both my parents worked and retired when they were 65, so it was hard for me to wrap my head around. I finally broke through and started with refinancing my primary home. A good friend of mine told me he was getting into real estate, and one of the first things he said was, “Well, if you ever get a deal or something, let me know, I’d like to partner up.”
My first deal was off the MLS. It was a full-on BRRRR deal—buy, rehab, refinance, rent, repeat. I bought it way below market value and went way over budget on the rehab, but it worked out. I refinanced, got the cushion I needed, and bought the next one in June 2019. Since then, I’ve gone from one primary residence and one investment property to seven total properties. I’m house-hacking one of them, four are short-term rentals, and three are long-term rentals.
It came really fast through an absolute mindset shift in what I saw as possible.
