Category: Debt
Air Date: 06.10.2021

Becoming Debt Free With Dr. Jeff Anzalone

Today we are paid a visit from an amazing guest with so much value to offer all of you! Dr. Jeff Anzalone discusses how to become debt free.

Dr. Jeff Anzalone is the brains behind Debt-Free Doctor, a service that helps doctors and healthcare professionals to create passive income while still working in the medical space. Dr. Anzalone is a full-time periodontist as well as an author, and we get to hear all about his journey after medical school and how he found his way first into passive investing and then subsequently into active deals! His main goal in his real estate work is to show people how they can stop trading their time for money, and increase their income dramatically. One of his main points in our conversation is around the importance of mindset and how we have to get away from an outlook based on scarcity before we can experience success. We also talk about his best advice for finding and locking down deals, questions to ask deal sponsors, and why he is so dedicated to helping others reach a better financial life! Tune in to get it all!


Key Points From This Episode:

  • The beginning of Dr. Anzalone’s career and how this pushed him to pursue passive income.
  • Lessons that Dr. Anzalone learned around debt and income from the get-go. 
  • How a negative and worried attitude can impact your work and personal life.
  • The steps that Dr. Anzalone took to address and change his scarcity mindset. 
  • Dr. Anzalone’s skiing injury and how it influenced his attitude towards providing for his family.
  • The first asset classes that Dr. Anzalone pursued and the early seminars he attended.
  • Dr. Anzalone’s motivation behind starting his Debt-Free Doctor business!
  • The transition that Dr. Anzalone made from passive to active investments.  
  • Reason doctors should be seriously considering new revenue streams as a failsafe. 
  • Tips and tricks for a healthy process of finding and securing deals!
  • The most important question that investors should be asking of their deal sponsors. 
  • Proudest moments along the way for Dr. Anzalone: the enjoyment of his helpful work. 
  • Dr. Anzalone’s best book recommendation for all of our listeners!
  • The key to success for Dr. Anzalone: dealing well with and learning from failures.



“There is more than enough to go around, that is one of the main lessons that I learned.” — Dr. Jeff Anzalone [0:09:03]

“I needed to have other income streams coming in, that aren’t relying on my hands, and I didn’t know where to start.” — Dr. Jeff Anzalone [0:14:43]

“You’re really never going to know what to do unless you start to educate yourself.” — Dr. Jeff Anzalone [0:22:10]


Links Mentioned in Today’s Episode:

Kent Ritter

Dr. Jeff Anzalone

Debt-Free Doctor

A Doctor’s Guide: How To Create Passive Income With Real Estate

Dr. Jeff Anzalone Email


Dave Ramsey

The Passive Income Physician

Thomas Black8

Die With Zero


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Contact me at

My operating partner, Birge and Held Asset Management have a twelve-year track record creating sustainable wealth for over 2000 investors through high-quality multifamily investments.

Thanks for listening!

—Full Transcript Below—

JA: You become more noticeable if you have some sort of fear or anxiety thoughts that pop into your head about certain situations, and you can address some as they come up and just don’t constantly harp on it. But I think, especially when I started my website, and started connecting with other people, then through them connecting with other people, and then — almost like a whole new world opened up.” 


[00:00:28] KR: Welcome to Ritter on Real Estate, the show about how to passively invest like a pro. On each episode, I interview real estate experts who give their top investing advice, strategies and tools, and I break down the insights and the practical steps to avoid the pitfalls and make better investments. I want to help you passively invest like a pro. This is Ritter on Real Estate, and I’m your host, Kent Ritter. 


[00:00:52] KR: Hello, fellow investors. Welcome to Ritter on Real Estate, where we teach you how to passively invest like a pro. Today, my guest is Dr. Jeffrey Anzalone. Jeff is a full-time practicing periodontist in the great state of Louisiana. He’s an author and the founder of His focus is on helping doctors and other high-income professionals create passive income from real estate, so they could stop trading their time for money. 

Jeff, thanks for being on the show today.

[00:01:19] JA: Thanks for having me. I’m looking forward to it.

[00:01:21] KR: Yeah, absolutely. Why don’t you tell us a little bit about your story and how you came to be where you are today?

[00:01:29] JA: Sure. Couple of weeks before I finished my training at LSU, I was supposed to a group practice here in a small-town Louisiana. I was relying on that group to teach me about the business, because when you go to demo school, or medical school, or law school or whatever, you learn your trade, you don’t know how to run a business, you don’t learn anything about money either. Unfortunately, two weeks before I finished, they pulled the deal out from under me, and I had a two-month-old, about $300,000 of student loan debt. But the worst part about it was, I had no clue what to do, where to start. Because you start about a year before you finish your training to start networking with people or if you’re going to buy a practice, go in with somebody, because it takes about that long to do it. That threw us in a bit of a frenzy.

Luckily, a guy out of the blue was also a demo specialist. He had gone through sort of the same ordeal, it happened to him too. He took me under his wings, he helped me network with other dentist in the area, start the business, rent from him, could use his stuff, could use his equipment, which was great. I don’t have to take out anymore loans. But also at that point, when I did have the job, we had bought our house and we’re just paying interest only on it. I had a ton of debt, and I actually had to just go back to what I was doing in high school and college, mow yards probably — the only [inaudible 00:03:11] to the US, that was mowing yards on the side, but you got to do what you got to do to make ends meet for the family.

At that time, we were pretty big Dave Ramsey followers, so I just followed his baby steps to start tackling a lot of the different student loan debt we had, and then cleared that up, eventually cleared up the mortgage. That took about seven, seven and half years to do. Finally, bought the building that I’m in now, and moved on and opened mowing and practice.

[00:03:45] KR: Awesome! That’s a tough situation. It’s kind of a punch in the gut, but you’re able to come back and ultimately thrive. What did it teach you?

[00:03:54] JA: It took a lot to get out of what it did to me. I went from having — when you’re in school, knowing that you’re going to get out, making a decent income, decent six-figure income, you don’t really worry too much about your bills or debt. Then when you have all that taken away from you just like that, actually, I went from I guess more of an abundance type mindset to one of scarcity and fear to see everything, that. “Hey! Everything can just be pulled out from under you. It really took me a long time to get rid of that scarcity/fear type mindset, which occasionally, it will pop its head up again. But that was probably one of the hardest things to do, to get over. I really didn’t know it had happened, that’s why I started learning about it. Then I looked back at what had happened over my career, I said, “You know what? This really sounds like me.” That was one of the biggest factors.

[00:04:54] KR: Yeah. No, I think that’s a great lesson, like mindset is everything, right? Through that lens, you view the world and it affects the decisions you make and the opportunities in front of you. Whether you view them as opportunities, or as difficulties. You end up in this scarcity mindset, this fear mindset. You said it took you a while to kind of realize that. But what was the impact in your life, your business, of that when I call negative mindset?

[00:05:23] JA: If I could sum it up in one word, it would be worry. Always worrying about the next day, the next patient, where we’re going to have enough to live on. It’s kind of funny for a few years at that time. I was writing down, sort of journaling every day. I came across that journal not that long ago, and it’s just funny looking back at what I was 10, 12 years ago what I was going through and just kind of laugh at it. Looking at it now, going, “Hey! That’s silly that I was even worried about that” or this and that. I do know that people do recommend that you journal, so I do think that — I don’t do it anymore, but I do think that that could help. Especially if you’re going through issues or if you have kids that are going through issues, actively writing it down to get through some of that. 

[00:06:11] KR: Yeah. I think journaling is a great technique, and I’m sure that was pretty powerful for you to be able to look back and see that change in mind. Because it’s probably not as a parent day to day, but when you are able to look back several years and kind of see that comparison, I’m sure that’s pretty shocking.

[00:06:31] JA: Yeah, for sure. Once you realized that more than likely, things happen for a reason. I’m glad all this happened, because I wouldn’t be in this position that I’m in now. I’m really thankful for that.

[00:06:48] KR: You went through this period of scarcity, you continue to educate yourself and learn, you recaptured your abundance mindset it sounds like. But the idea of worry as you mentioned is kind of sticking with you. How did you cure that? How did you cure that worry? What did you put into place?

[00:07:09] JA: Well, I don’t think you ever cure worry. It’s you become more noticeable if you have some sort of fear, or anxiety, thoughts that pop into your head about certain situations. You can address some as they come up and just don’t constantly harp on it. But I think once — especially when I started my website, and started with other people, and then through them connecting with other people, and then — almost like a whole new world opened up that was out there. I’m real thankful for the Internet, and these Zoom calls and where you can connect with people. Because as a solo practitioner, I come here, I do my little thing and I go home. It’s a real small world, no pun intended. You can look at that or really anything, any type of thing in your life. If you get some sort of — we’re talking about real estate, take real estate for example. 

You may want to be trying to do investing, on your own. But once you get out there, go to meetings, go to conventions, join masterminds and you just know and you start meeting people and you’re like, “Man, the possibilities are unbelievable.” My local real estate mentor, he’s a billionaire with a B. I went and talk with him a couple of years ago. I got home and I told my wife, “I learned more in two and a half hours with him than I did probably in two years of college.” He just completely opened my mind to the possibilities out there. But if you’re in that fear, scarcity mindset, then there’s only one pie. You have your pie and you can’t let anybody have any piece of your pie. You want to hoard everything versus abundance, where there’s a pie shop in the back, cranking pies out for whoever wants it. There’s more than enough to go around. That’s one of the main lessons that I learned.

[00:09:09] KR: That’s a fantastic lesson and it seems like it’s had tremendous impact on your life, in your level of success since then. So you mentioned, you found this work of like-minded people, you start kind of building that abundance mindset by realizing that there’s like this whole new world out there like you said. I imagine a lot of that was getting into different types of real estate investments and understanding passive income based on what you’re doing now. Tell us a little bit about how that experience evolved into this idea that you needed to develop additional streams of income.

[00:09:47] JA: Well, I think it all started when I was — someone else asked me this question on a podcast that I really had to think about it. I think it all started back years ago when we were skiing in Beaver Creek, Colorado when I was going down a run and a kid cut in front of me. I swerved, and I feel and injured my risk. I guess you never think about getting sick or injured until you get sick or injured. I’ve got two teenagers and I think they are invincible.

[00:10:22] KR: Yeah, of course.

[00:10:24] JA: That got me thinking, “Well, if I did become temporarily or permanently disabled, how would I take care of my family, because I’m the sole provider for the family for the most part.” That got me thinking, I need to have other income streams coming in that aren’t relying on my hands. I didn’t know where to start. I started — I’m an avid reader so I started reading books, networking with people, listening to podcast. Then I noticed that one of the common characteristics of millionaires was about 90% of them had real estate in their portfolio. The average millionaire had I think three to nine streams of income. The only real estate at that time in my portfolio was our primary residence and I only had one stream of income coming in.

That’s what got me started going down the road. It wasn’t like an overnight deal as you know. It took years and years. But that actually got the ball rolling down the hill. 

[00:11:28] KR: Got you. Now it makes a ton of sense. What type of real estate are you investing in?

[00:11:34] JA: I think it’s really important especially if you’re married to develop goals because they’re going to guide you down the path. I knew that I wanted other streams of income, but I didn’t want to get another job. We wanted to spend as much time with our kids before they move out. I didn’t want to work extra weekends. I see some of these dental offices open on Saturdays and Sundays, I’m like, “That’s why you go to dental school to not work on weekends.” 

[00:12:04] KR: I think my dentist just only open like four days a week maybe. 

[00:12:08] JA: Yeah. To each his own, I guess. But I knew I didn’t want to do that. I didn’t want to work extra hours. I knew after learning about single-family homes, and friends that are active investors, I knew I did not want to be a landlord and deal with these sheriffs calling you at two in the morning, somebody broken into one of your tenants car, or plumbing issue, or — my anesthesia nurse, she’s an active investor and over a couple of months ago, somebody called her one in the morning, hot water heater busted, so she was walking around in six inches of water in her — I don’t want any of that.

Luckily, during that process, I was able to find out there was other options, passive investing. It was at a seminar in Dallas that I learned about all these different things, node investing and mobile home parks, apartment syndications, which — that’s what I was sort of attracted to. Then from there, developed a little more goals. Like I said, I have two teenagers. I want something that’s lower risk, which is going to have a little bit lower return, but more conservative, something that’s cash flowing that has a track record. That led me more to value-add class B, B class apartments. We’re looking at some other investments, other types of investments this year. But that’s why it’s important setting goals, because those are going to guide you as you start looking at different things down the right path.

[00:13:44] KR: Yeah, absolutely. You set out, you created Tell us a little bit about that website.

[00:13:56] JA: I realized as a doctor, we have like this big S on our shirt we walk around with, not for Superman, but for stupid because we get pitch stuff all the time. I just hear story after story, people and myself included getting screwed out of a deal. Once I started learning this process and started becoming a little bit more successful with it. I wanted just to share my experience. The only thing that I knew how to do was literally push the power button on the computer, and get on the Internet, and check my email and go to websites. That was it. I had to teach myself how to resource online, how to start a blog. It was nothing more than what I was doing and then what I was learning. 

I would learn something about cap rate, then I said, “Well, I think people should know about that” and I’d write an article on it. The more that I did, the more people I had coming to the site, and then I started hearing from them. They would ask me questions, “Hey! What do you think about this? What is this?” Then that would give me — it just started growing from there. Now, I think we average 30,000 to 40,000 visitors a month on the site. It’s gotten fairly popular.

[00:15:23] KR: That’s great. I think that’s your abundance mentality and practice. You’re not just hoarding these lessons you’ve learned, but you’re actively seeking to give back. I think that’s amazing. I think you’re giving back, and teaching people and helping people avoid bad mistakes, which is a very kindred spirit. I mean, that’s exactly what this show is about as well, is how do we make those good investing decisions. That’s awesome.

You’ve gotten to that point, you’ve educated yourself, you’re passively investing. Now, you reached a certain point where you moved from passive to actually actively investing, right? Tell us a little bit about that transition.

[00:16:02] JA: It’s actually a funny story. About a year and half ago, I’m reading a book, I believe it was called The Passive Income Physician by Dr. Tom Black I had it like laying down on the stand next to me. I get an email from a Thomas Black, MD. at the same. I asked my wife, I said, “This is weird. What if this guy is stalking me on —” I don’t know if you could stalk people on Amazon or how that worked. It was strange the coincidence. But again, I don’t believe on coincidences. He just said he found my website, he really liked a lot of the messages, the education I was putting out. He was one of the partners in the Napali Capital, and about 80% to 85% of their I investors were physicians, doctors, dentists, chiropractors and just wanted to meet. But he was only outside of Dallas, only just four or four and a half hours away.

I started meeting with them every quarter, face-to-face, even during the 2020 shut down, gave me something to do because I couldn’t treat patients. But I went through that process for a year, meeting with them, walking property with them. I want to get more involved, really getting to know them and their family. Then I eventually invested with the them. After I invested with them, kept meeting a little bit more and then they asked me to join their group is a type of partner to where I’m pretty much doing what I’m doing now, educating people in investor relation. I thought that was pretty cool, and I was honored that they would ask me. Because I had already had invested with three other syndicators at the time. As you know, the more people you invest with, the more differences you can tell between each group.

[00:17:59] KR: Absolutely.

[00:18:01] JA: And if you just invest with one group, well, you’re going to probably end — they’re great if you have good returns, but that’s because you haven’t invested with anybody else. I was able to look at these four different groups, and the pros and cons. I just really liked everything that they were doing. They always put their investors first. Good group of ethical, moral guys. I couldn’t say the same thing about the other people because I didn’t really know them as well, but I could see the differences. That was the transition from going from a limited partner to a general partner last year.

[00:18:38] KR: Got you. Very cool. That’s an amazing path of education, and finding abundance and beginning to spread the wealth and then now actively moving to have partnership and your own deals. That’s really impressive story. For your peers out there who are not investing, or not creating other streams of income. This is coming from my background prior to real estate. I was in healthcare and I just know that doctors tend to listen to other doctors. Tell them why they should be investing in something to create other streams of income.

[00:19:14] JA: A great example is what happened last year with when pretty much the whole world shut down with the pandemic in 2020. You would think that pretty much any physician or anybody in healthcare that had anything to do with treating patients in general, especially with COVID patients would be really busy. But what happened was, and this is coming from my academy. I don’t know the exact word, but the Academy of Emergency Medicine Physicians, basically ER doctors. What had happened was, so many hospitals lost s much money and had to cut back, then a lot of these people now that had spots that were in the residency and had jobs lined up, well now they don’t. A lot of these people now that had spots that were in a residency and that had jobs lined up. Well now, they don’t, a lot of them. They’re like, “Well, I’m just well-trained person, I can’t get hired.”

It’s like, you never know what’s around the corner is what I’m trying to say. You never know in the next pandemic, or the next 9/11 that’s going to happen, or whatever, or you’re injured, anything. You don’t know. It’s more of an insurance policy from that aspect. But the other aspect is, and I like options. I don’t want to be told I have to work for 40 years and put all my money in a 401(k) and then I can enjoy myself when I’m 70. Well, what if you want to enjoy yourself in your 30s and 40s? Well, if you have extra income streams, you can do that. But if you don’t, then you have to do what everybody else does. I didn’t know the difference, so my job is to not telling people what to do, I’m just telling them there are different ways out there.

Being from Louisiana, to skin a cat or skin whatever and let them choose. But at least they have the option, kind of like, you know if you smoke, more than likely and then choose Lisa how the option like you know the slow more likely you’re going to get lung cancer. Well, you know the pros and cons and if you want to keep doing it, great. If not, so be it.

[00:21:21] KR: Yeah. I mean, well said. I think it’s about just taking a proactive approach. Taking a proactive approach and understanding that, like you said, you’ve got to create that insurance policy, you’ve got to create that fallback plan, that plan B. Because as you said, you never know what the future is going to hold, so you have to create options for yourself. I think that’s very well said.

I’m curious, someone who obviously — as you were looking at sponsors, as you were vetting deals, as you still are, obviously you’ve got a full-time job, you’re running a practice, you’ve got kids, a family. Tell us a little bit about your process for finding deals, vetting deals, vetting sponsors. How can someone who is extremely busy manage to do that?

[00:22:06] JA: I think it really starts with education, and you’ll really never going to know what to do unless you start to educate yourself. People are used to or probably at some point have found maybe a financial advisor or they found an accountant. Think about what process that they went through, hopefully they interviewed several. Just start asking around about other real estate investors who they’ve invested with and you’ll start hearing the same names come up of who to invest with and who to avoid. You want to look at their track record, how many deals have they closed, how many deals have they exited. You can go find as much background information as you can. A lot of it can come from their websites.

But again, asking other people about them, but you want make sure that they align with your — going back to goals, make sure that they align with your goals or they’re high risk, new construction if that’s what you like or lower risk but lower returns, more consistent projects. Well, that that type of person line up with you. What do they do for you as far as tax sell. Being a high-income earner, you’re going to have high taxes. Do they help with that?

Great thing about the group that I joined is, they actually acquired their entire accounting firm, brought them in house. So now they’re able to provide tax reduction strategies for all the investors. I think that’s a great thing, because as you know, that’s one of the reasons that a lot of us get into real estate. Those are some of the way that I recommend that people look at and evaluate.

[00:23:57] KR: Great. I appreciate the insight. As we move toward the end of the show. I want to move into our keys to success round. There’s a few questions I’d love to ask you. Firs one is, what is the one question that every investor should ask their deal sponsor?

[00:24:13] JA: I would ask them, have they ever lost money in a deal and just see what they have to say. If they haven’t lost money in a deal, maybe have they ever had a deal that didn’t perform as well as projected. If so, what did they learn from that. 

[00:24:30] KR: What are you looking for when you ask that question? What are you trying to vet out?

[00:24:35] JA: I guess you could kind of probably tell by the way that they answer it. I mean, you can sense when somebody is maybe not telling the whole truth so to speak. I want to hear just what they have to say. Do they have confidence in their voice? Are they sincere about it? Because as you know, if you do this long enough, you’re at some point going to lose and I lost early on in one of my deals. It was a crowdfunding deal I’m on. 

[00:25:01] KR: You and me both. 

[00:25:05] JA: I probably have you beat on their mouth, but yeah, that’s why I steer clear of crowdfunding.

[00:25:10] KA: Yeah, you may. Luckily, mine was kind of tail in the water, but yeah, I had very similar experience. I think that’s an amazing question and I like how you started with the sponsor, and vetting the sponsor out first, kind of understanding. I mean I think that gets to integrity, how do they answer it, do they tell the whole truth and all those things are critical. What are you most proud of in your career?

[00:25:32] JA: I would say — and you always hear this, if you find something that you love it won’t feel like work, and I’ve always said, “Yeah, whatever.” But it really is true. I mean, if you go to my site, I don’t sell anything, I don’t do anything like that. I just enjoy doing it and I spend upwards of 20 hours a week on it. Own the website, YouTube videos and everything else that goes along with it, these types of podcasts. I never get tired of it. I think I’m most proud of finding a real estate and having this niche. Maybe that’s the reason that God put me to dental school is because I can relate to these people that come to me and email me on a daily basis about passive income or real estate help. 

[00:26:22] KR: Yeah, absolutely. What books should everyone read?

[00:26:25] JA: It’s actually laying here on my desk. I just finished it not that long ago. I kid my wife because I told her that she was probably the co-author. It’s Die with Zero, Bill Perkins. I don’t have many books that really, really impact me like the way that this book did. But he really puts money, and life, and health in perspective, about how you should enjoy it while you can, while you’re healthy. Because if you don’t and you’re in your 70s and 80s, you’re not going to more than likely be able to enjoy it. It gives a lot of good examples. He was, I believe a hedge fund guy from Austin I believe, but great book.

[00:27:14] KR: Yeah, that’s a great lesson. I know you brought it up before about the typical mindset of building your 401(k), then retiring in 40 years and enjoying life at that point. But if you don’t have your health when you’re in your 70s, there’s not a lot you’ll be able to enjoy.

[00:27:32] JA: Yeah. I mean, because a lot of times people say, “Well, I want to save all this money and when I retire, when I’m 70, I want to travel.” But think about it, if you get to that point, you’re like, “I don’t feel like traveling. I don’t want to deal with airport people, and airplanes and sleepless nights that these — I mean, enjoy it now while you can and while you still enjoy it is his main thing.

[00:27:55] KR: Mm-hmm. That’s a great lesson. Lastly, what is your number one key to success?

[00:27:59] JA: I’d say and I heard this the other day that I actually reiterated it to my kids. Somebody on a podcast that interview the girl, I don’t remember her name, but she started — she’s a billionaire who started SPANX, the clothing company. I don’t remember her name. But she said, growing up, her dad always asked her and her brother — I’ve never heard of this before. He said, “Hey, kids! Tell dad what you failed at this week.” Because what do parents do now, they don’t want their kids to fail at anything. They want everybody to get a trophy, which is the stupidest thing I’ve ever heard of. But there’s a winner and there’s a loser, and you’re going to have successes and you’re going to have failure. I guess, don’t be afraid to fail.

[00:28:44] KR: Yeah, that’s awesome.

[00:28:46] JA: Looking back on my life, I am where I am today because of my failures, not because of my successes.

[00:28:52] KR: Yeah, you often learn more from the failures, right?

[00:28:55] JA: Absolutely.

[00:28:56] KR: Great, Jeff. I appreciate you being on the show. We talked a little bit about the website, maybe reiterate for folks, if folks wanted to get a hold of you, how can they get in contact?

[00:29:06] JA: A couple of ways. Actually, I put together a passive income guide if they go to They can download that or if they have any specific questions, 

[00:29:24] KR: Awesome. We’ll make sure it’s all on the show notes for folks. 

[00:29:26] JA: Perfect.

[00:29:27] KR: Jeff, thanks for coming on and sharing your story, and your knowledge and your unique perspective. Have a good rest of the day.

[00:29:33] JA: Yeah, you too. Thanks for having me on.

[00:29:35] KR: Absolutely.


[00:29:37] KR: Thanks for listening to another great episode of Ritter on Real Estate. Hit the subscribe button to make sure you don’t miss out on the content that will make you a better investor. Also, visit for articles, videos, and tools curated just for passive investors. Until next time, this is Kent Ritter with Ritter on Real Estate. Now, go out and invest like a pro.