Listen to Dr. Jeff Anzalone discuss how he went in pursuit of finding a way to create multiple streams of income. He created a blog called debtfreedr.com to help educate other doctors and other high-income earners leverage the lessons he's learned along the way. Jeff's learned that there are a vast number of high-income earners out there that are extremely smart in their field but have neglected to focus on their financial investments, which has negatively impacted their net worth. Jeff is looking to educate and get the word out, specifically that there is a way to take back control of your finances!
Table of Contents:
- Where To Listen To The Podcast
- A Doctor With Multiple Streams of Income
- Mindset Shift
- Managing Your Streams of Income
- The Passive Investor Circle
- Consistency Is King
- How to Reach Dr. Jeff Anzalone
- Join This Multifamily Conference In 2021
A Doctor With Multiple Streams of Income

Darin: Jeff Anzalone lives with his wife and two teenage children in Louisiana. Jeff is a periodontist doctor who went looking for a way to create multiple streams of income and created a blog called debtfreedr.com to help other doctors and other high-income earners learn from his experience. He's learned that there are many high-income earners that are extremely smart people in their fields, yet have not focused on their financial investments, and their net worth has suffered accordingly. He's out there working to get the word out and help others.
How do I know Jeff? This is going to be a little bit of a test interview here. Because all the other interviews thus far, I think, we're in the low 30s in terms of episodes have been people that I knew well in the industry or that somebody that I know well has put me in touch with. This will be the first time that Jeff reached out to me. He had listened to some of the episodes, reached out to me. I thought it was a really interesting opportunity to talk to somebody in the medical space.
Jeff is a doctor, and I'm really interested to hear his take on how he got involved with real estate being in the physician field. With that again, Jeff I appreciate you coming on the show. Can you just start out by sharing how many properties and how many units you're currently invested in?
Jeff: I'm not exactly sure about the unit numbers, but currently, where my wife and I are in six separate real estate syndications at this time.
Darin: Fantastic. As a passive investor.
Jeff: Correct, as a passive investor.
An Accident That Started It All
Darin: You are a doctor. What type of doctor are you? Where are you located?
Jeff: I'm a periodontist located in the northeast part of Louisiana. I have my own practice, started it about 16 years ago.
Darin: Fantastic. You started the practice 16 years ago. When did you get involved in real estate investing?
Jeff: I got involved actually by accident about five or six years ago. We were snow skiing out in Colorado. When I got off the ski lift, I had to avoid a kid that cut in front of me. I fell. When I fell, I caught myself. Then, I was injured. Luckily, nothing major, but I had a minor injury to my wrist. If I don't have my hands and wrists, it's hard to do work. That got me thinking about what I would do if I was either temporarily or permanently injured because, at that time, we were only relying on my income coming in from my practice, the active income. I think that's started leading me to look for other income sources which eventually led me to real estate.
Darin: That says a lot because there's a ton of people out there that work in corporate America. We're groomed to think that that's the safest place to be. But what happens if there's an injury and you can't work anymore, right? You went and actually formed your own practice. Then you became your own business owner. That's one step further where you think you have complete control, but again, if you get injured, then what do you have to rely on to support your family? That got the kind of the gears rolling in your head. From that point on, where'd you go from there?
Different Streams of Income in Real Estate
Jeff: Well, I love to read. So, I started reading what other people were doing. It seemed like everybody was doing this real estate stuff. But at that time, the only real estate I knew about was we just owned our home. That was it. In my mind, I thought you had to actually own the property. I've got a lot of friends that are in town here that own real estate or they work for their dad that owns it. I started going to lunch with them and looking at actually some single family homes. That's when I realized that it was going to be a lot of work, but I was willing to do it.
Then, I went to a meeting in Dallas. There was a dentist that put on this big workshop that he was teaching other dentists how to get into real estate. Again, I thought it was going to be all about active investing, but it actually opened my eyes to all the other different ways you can invest in real estate besides being an active investor. Whether that would be being a passive investor in syndication, whether doing notes, there are all kinds of different things that I had no clue about.
But, again, it had me open my eyes to see that I could continue to work into my practice doing what I knew how to do best. But on the side, diversifying real estate starts building up passive income. Then, I didn't have to be a landlord because I really didn't want to do it because that was going to be taking my wife and me. Taking me away from what I wanted to do more, and that spent more time with the kids while they're still living with us now.
Books That Helped Dr. Jeff
Darin: That makes sense. What books did you read to start educating yourself?
Jeff: I'm going to have to turn around and look and see. I've got all my books over here, but I know one of them was Multiple Streams Of Income. I read that. I've probably read 40 to 50 books since then. A couple of the Grant Cardone books. The 10X Rule, The One Thing, focusing on your one thing because I'm all over the place sometimes.
Darin: That makes sense. You hear that you need to bring on multiple streams of income, but if you're in corporate America or if you're a business owner, you think that you're covered. Like, why do I need to bring on multiple streams of income even if Warren Buffett talks about it and other very well-known people until you really immerse yourself with other people that are doing that and then you see the advantages of it. Five years ago, you started looking. When did you invest in your first passive opportunity?
Jeff: Well, at that time, crowdfunding, online crowdfunding, started becoming popular. The big player at that time was realty shares. I started doing a few little debt deals with them. They worked out pretty well. Did that for probably a year, a year and a half.
Then, I decided to really go big into an equity deal with them. It was an apartment complex in Oklahoma, $50,000 minimum. Then, looking back, this just goes to show me how little I knew about real estate because I was relying on them to tell me, or I was putting my trust in them to invest in the real estate.
Getting Involved With Real Estate
Jeff: The way that I would invest was I would look at the pictures. Which one looked the best? What returns were the best? Then, that was it. I had no clue about the sponsor, what the business plan was. I mean nothing. Unfortunately, every investor lost all their money.
Darin: Are you kidding me?
Jeff: No. Then, realty shares basically went under. And another company has brought it over. I wrote an article about it on my blog. That was probably one of the most popular articles because people said, "Well, most people don't ever talk about their failures. They always talk about their successes." Looking back, that would have been a really good time for me to quit because just getting into it, you lose 50k, and that's a hard pill to swallow.
I knew that there were a lot of people building wealth and streams of income with real estate. That was kind of the turning point for me to start my blog to start teaching people what I learned about getting out of debt, student loan debt. But then learning what I was learning and then making this mistake and then start by really learning how to invest in real estate with all the different terms and everything that goes on to it. It was almost like a little diary.
I would read something and, oh yes, that would be good. Then, I'd write an article about it. Then, I just kept going on and on. I think it's just gotten popular from there.
Darin: Fantastic. I got involved with syndications and buying real estate both passively and also as a general partner only three years ago.
Winning the Streams of Income by Losing It Initially
Darin: In all my travels and all my discussions with people, you are the first person that I've heard that has lost money on a deal.
Jeff: I won the prize.
Darin: You win the prize. Every other person. I know people that are invested in 20, 30, 40 deals and I've asked them that question. Have you lost on any of these deals? Everybody has told me they have not lost their capital on any of the deals. They've had deals where they didn't meet their proforma with the business plan, or they were forecasted to have a cash flow of 8% and maybe they didn't achieve that. Maybe, it was 4% or maybe they didn't receive any cash flow for a while, but when they sold the deal, they made up for it and came out positive.
That is the first time I've ever heard of somebody actually losing money on a deal. That was the first deal that you lost money, and you still came back and went to go after deal number two. Why was that? Why did you come back?
Jeff: I guess just Louisiana people sometimes are not knowledgeable.
Darin: Oh, I don't know about that. You had read enough books. You had met with other people that we're investing in real estate. I have to imagine you had faith that just because one deal went bad doesn't mean that all deals are going to go bad.
Jeff: I think reading a lot about wealthy people and millionaires. And I think it was through basically the average millionaire had like anywhere from three to nine different streams, and over 90% of them built their wealth with real estate. It's not something that hadn't been done before.
The Debt-Free Doctor & His Streams of Income
Jeff: I've failed so many times in different areas of my life that I realized that there are two things you can do. When you fail, you can either learn from it or you can quit.
I was like, "Well, I wanted to learn from it. And I took probably 18 months off from doing any type of real estate investing after that just to really dive deep and learn and network with people and man up. I went to all kinds of meetings, and meetups, and groups, and conventions. You start hearing about what different people are investing in like syndications.
Then, you start hearing about who people are investing with. Like with anything, you hear the more popular people, the people that others can trust. Then, I decided to bite the bullet and start investing and just tried it out. That worked out pretty well and did another one and then another one. The more that you do, the more you learn, the more you get comfortable with it. As I was going through those motions, I was documenting it on my blog. Then people can follow the journey a little bit, working on treating patients.
Darin: Talk about the blog talk. As you started to invest, you started a blog and a website. What was the goal for that? Who's it geared towards? What's the name of it?
Jeff: It's debtfreedr.com. The first goal was just to talk about my journey of getting out of about $300,000 of student loan debt. And some of the financial mistakes that we had made, and just some basic investing advice. That really was the starting point of it, but then, the more that I got into real estate, the more I started to switch over and talk more about that.
Mindset Shift

Jeff: Talk more about the wealth mentality, the mindset that you have to have because most of these real estate conventions and seminars that I was going to, the majority of them started off with telling others, "Hey, it starts with a mindset shift."
Darin: What does that mean to you, a mindset shift?
Jeff: I kept hearing it. Maybe, it was like when I lost all that money and failed, but then, I had a shift. I could quit, or I could keep going. And I knew the goal that I wanted. I know other people have done it. Then I just went for it. I just kept going. So I never quit.
Jeff: I think growing up, you hear about the poor versus the wealthy mentality or the mindset. A lot of us, myself included, grow up hearing from our parents. We can't afford this that costs too much. What do you think, we're made out of money? It's funny that now that I have kids, I've caught myself saying the same things. What do you think money grows on trees. You hear that your whole life. I naturally had acquired this scarcity mentality like there was only so much money to go around. It trickled over when I started my practice.
Darin: What do you mean by that?
Jeff: It's like a scarcity mentality. There are only so many patients that were in my area. I was just focused on one little way to get them, but then once I started doing online marketing and advertising, I just realized there are people all over. It just opens your eyes. Growing up hearing that and getting that scarcity mentality and then starting to read about, hey, there's a difference.
The Abundance Mindset With Streams of Income
Jeff: There's something called an abundance mentality where it's a glass half full or half empty sort of deal. Once you realize that money is not scarce, look at the government, they print it all the time. It's all over.
It's just a different way of thinking. I think whenever you accomplish something in life that you never think that you could do and then you accomplish it. It's kind of like, "Okay. Well, let's move on." Now, it just opens your eyes to doing something different.
For me, with having kids, I think it's really important for parents that are listening to this that words are very powerful. What you're speaking to your kids or to your spouse and your kids can hear, that's something that can stick with them for a long time. Just be really careful of the words that you're saying that you make sure that you speak, always encourage them. These different principles that we're talking about today, that can make or break your kids' financial future.
Darin: How many kids do you have?
Jeff: I have two. I have two teenagers.
Darin: Two teenagers. Look, being a doctor is very esteemed. There's a lot of people that look at that as being like, "Holy cow. This guy, he went through so much schooling to get this, to build it, to graduate, and then to start building a practice." You've had the practice for 16 years. You're raising your children up as a doctor. Now, you learn this real estate investing side. What are you teaching your kids? Are you focusing on the multiple streams of income and talking to them about that and the abundance mindset or become a doctor or a lawyer or some other esteemed position?
Talking Streams of Income With the Kids
Jeff: It's funny you ask that. Recently, one of the things that I pray about every night is to help my wife and I find ways to stay connected with our kids especially in junior high and high school. You know, because once you get in with the wrong crowd, that can really destroy a lot. I've seen a lot of people destroy their lives just from that one little thing.
I want to stay connected with them. The cool thing with my youngest son who's 13, he's really into learning about investing and finances. He took it upon himself to want to read Rich Dad Poor Dad.
He's reading it now. We play the CASHFLOW for Kids game. That's been a great way that we can have conversations about finances. He asked me the other night. So he said, "Dad, how do I avoid paying taxes?" I said, "Son, you got to get a job first." But he's all into it. His brother is totally different. And his brother will probably work for him one day, but you never know.
His brother likes other things, but it's cool to see that. Of course, staying in school and making good grades is good. I recommend that but I used to think that was the only way to be successful in life which I know now it's not true at all. When I say successful, I mean from a wealth standpoint not from other things.
But now that you read about all these people with high school education. They have gone on to build these real estate empires or they're very wealthy, and a lot of it is common sense, financial common sense. But I just encourage them to pursue what they like.
Common Sense Is Key in Achieving Streams of Income
Jeff: Don't do anything just for the money and follow what they like. Then, they like it, the money will come at some point.
Darin: Right. I think you mentioned common sense. I think there's another component to it. It's not just real estate related. It's any kind of other venture. For you, you had to start your own practice. It's actually taking action. You can read all the books you want, but if you didn't actually make the investment, you never would have learned.
Unfortunately, you had a really tough lesson in your first investment, but it didn't scare you off. You continued to learn from that and then started to invest in other deals. Have those other deals performed well for you?
Jeff: Yes. They've all performed well. Now, during the pandemic in 2020, the only difference was in two of them. Instead of them paying monthly distributions, they went quarterly which didn’t really matter to me because I don't really need the distributions now because I'm still working. That's what I stress to people. If you find a good sponsor to work with, they'll invest in areas of growth, and people. Then they can pay their rent and things like that.
When pandemics and problems happen which problems are going to happen, you'll be in a stronger investment versus maybe some of the other people that don't have as good of an experience.
Darin: Right. I took a look at your blog. It seems like it's geared towards trying to introduce and educate other doctors on how they can become debt-free and how they can invest in real estate. Talk a little bit about that and the focus of that.
Creating Streams of Income With Debtfreedr.com
Jeff: Well, it started off mainly focused on doctors, but it's really pretty much any high-income earner. I get a lot of engineers and even accountants and attorneys. And I even let some attorneys in. That's kind of the running joke with them. They'll email me, "Hey, I'm an attorney, but can I join your passive investor circles?" Like, "Yes. I guess as long as you don't sue me."
We're talking about common sense earlier. It's amazing the conversations, and I'm probably on the phone 40 to 50 doctors or more or some sort of high-income earner or more a month. It's amazing to me these people that are in their 50s and their 60s and they're successful. They've made a great six-figure income their entire life and they're broke.
It's mind-boggling to me. It has nothing to do with smarts. That's the thing. These guys are smart. Orthopedic surgeons, neurosurgeons, I mean smart people. Well, I talked to one guy two weeks ago in my mid-40s, I think in Pittsburgh, focused on getting out of debt like $300,000 of debt. He did that. And he was in a group practice. Then, he decided he wanted to go on his own. He started his own practice after he paid off his debt. Then, he started not doing really well. Now, he's trying to get back. I think he joined another group. He had $25,000 to his name.
Three kids, he's married. He wanted to get into real estate. Then, I started asking him questions. He couldn't really tell me what his income was the last two years working on his own. I said, "Well, what about your tax returns?" He said, "Well, I hadn't filed taxes in two years." It's just like, "Dude, you're freaking going to have the IRS coming after you."
Knowing Where Your Money Is
Jeff: It's story after story. I'm talking about just basic financial common sense. Then, these people tell me that they just turn all their money over to these financial advisors. They don't know what their advisors are doing. They're making a ton of money. They're just giving it away. I'm like, "Well, what are you in? What do they have you in? What are you paying?" I don't know. And I don't understand all that.
I'm like, "When you do that, you're giving that control away to somebody. You can really get taken advantage of. I'm not saying that advisors are bad, but you should know where your money is and what it's doing and what the fees that you're paying and what the goals and strategies are." It's just like, "I don’t want to know." To me, it's just mind-boggling. I'm just trying to bring awareness to the blog about that. That was how it started. Then, again, it's shifted more to teaching the real estate part of it too.
Darin: That's a great, great point, giving control away. You're talking a lot about the people that you've touched, which is doctors and high-income earners that have reached out to you, but I think that a lot of people fall into that camp. It doesn't have to be people that just gave it away to financial advisors, but a lot of people in corporate America, when they sign up, they sign up for their 401(k). They have a few options.
When they're signing their employment forms, they select an option. They just forget about it. One thing that I've learned from being around a lot of people in the real estate world is you need to take control of your investments and not just hand it over.
Managing Your Streams of Income

Darin: That hand over could be to a financial advisor. In my case, I'm 50 now, but first, 47 years, I put my money into ETFs, into stocks, into different 401(k) plans, different companies. I just put it there. I always taught that it was just going to grow. But it's being irresponsible.
I fell into that camp and that I was making really good money. I was putting money aside, but you have to take responsibility for those assets that you've put over there and understand it and spend the time to understand what investments you're getting into and who's managing your money.
Jeff: That's 100% true. There are several people that I talked to that I'll ask them what are you doing with their investments or whatever. It's just like, "I send them a check every month. I have no idea what they're doing, but the statements look like I'm making money. I'm not worried about it." That's their answer.
I heard a guy once tell me, "When you start a business, start a practice. Never delegate the marketing or your checkbook." I've always learned that. I always kept that in the back of my head because at least in our field embezzlement and fraud are huge. I think one out of every either four or five doctors get embezzled. They have their own practice. It's pretty high.
Darin: That is high. You talk about getting debt-free. Do you believe in completely getting debt-free or do you believe in good debt versus bad debt?
Jeff: When I got out of training, I was a big Dave Ramsey disciple. I followed his 7 Baby Steps. That was all that I knew then. I think personal finance is just that. It's personal.
Bad Credit vs Good Credit
Jeff: What's right for me may not be right for you or somebody else. Some people say, "Never pay off your house," because you can use that equity and use that money and make more money somewhere else instead of just doing that. Some people say, "Pay off your house." It's just a great feeling. Again, I don't think there's a right or wrong answer. It's what's best for you. What makes you sleep better at night?
Darin: Right. I would say there's a piece of that I agree with. But then there's also a piece that I would say that look if you're going to use debt to buy non-productive assets, you're going to use debt to buy furniture and other stuff that are depreciating assets, it makes no financial sense to me. But using debt to buy real estate and leveraging real estate, you can get a much lower cost of funds by leveraging a loan.
Then, the equity owners, their returns will be increased by having that leverage. I think that it makes sense to use debt when you're buying cash-flowing assets like cash-flowing multifamily properties or other cash-flowing real estate assets.
Jeff: Yes. I agree with that. Again, I didn't know anything about that the first 10 to 12 years of practice. I was just focused on what I was learning. All debt is bad. Get out of debt. We did that, but now that I've learned different ways like you talk about real estate, as long as you're doing it, doing it smartly and doing it to where it's again, like you said, cash-flowing properties, that's different than going out and buying a BMW or a boat or something like that on credit.
Tax Benefits of Real Estate
Darin: Right. Another thing that you talked about on your blog and you're educating other doctors and the high-income earners are the tax benefits of real estate. Talk about that. What do you teach in that regard?
Jeff: Well, the main thing that I want to teach them, a lot of them think if I invest in real estate, well, then that's going to lower my income tax with my practice. As you know, unless you've filed for real estate professional status, that's not the case, but I do want to tell them that I do like to educate them on all the different ways. You can get tax benefits from investing in property. Most of the time, that'll offset your passive income.
You got to think about how much money you have to save in the stock market or a mutual fund or whatever to take that money out. Then, you pay taxes on it. You have to invest a lot of money to get back the money, a high enough amount. For instance, a financial planner, they'll tell us you need 10, 12, $15 million to retire. You need to be with me for 40 years. We're going to work this plan out. They get us from day one. You're stuck. Okay, well, then, I got to work till I'm 65, and I'm with this guy. Then, that's it.
People getting out with more and more debt three, four, $500,000 of debt or more. Then, every year now, our salaries are either plateauing or decreasing because of insurance reimbursements and cost inflation. Now, with the way the government's going, we don't know what it's going to do to our field medicine if they're going to make it more socialized or what. We don't know.
Options & Streams of Income
Jeff: With all those uncertainties, trying to save up 10 to 12 million bucks is pretty daunting versus looking at it a different way and investing for now replacing your monthly expenses with passive income. If you could do that and get tax-free income now to replace your income, well, that's financial independence. You may need a million and a half, $2 million in passive syndications or something that's going to produce passive income versus 10 or 12 million bucks. That's a big difference. That's a lot more doable for somebody making 200 grand a year than the other way.
What I like are options. It gives you options now that if you get burned out and you want to do something else or you want to work part-time or whatever you can versus, well you got to work till you're 65 and that's it.
Darin: Right. You talked about mindset before. That's a mindset shift. I went through that same thing once I got surrounded by a bunch of other real estate investors. They educated me and said, "Darin, instead of having to build up that big nest egg…" That's how we're educated through school, through college in the corporate world, is you have to build up this massive nest egg. Then, when you retire, you're going to pull from it.
But then, I had a lot of other people tell me, "You don't need to look at it that way. You can look at investing your money into cash-flowing assets. Then, you take that passive income, that cash flow that is distributed to you. As long as your lifestyle is below that cash flow, it doesn't matter how big your nest egg is." Then, as you get gains, you roll that into additional cash-flowing assets.
Grow Your Stream of Income Passively
Darin: And so, your passive income continues to increase. You can increase your lifestyle from that standpoint. That's, in my mind, has turned to be the goal, is how to continue to grow that monthly passive income versus having this huge nest egg target. The other thing somebody told me which I know for myself, it holds true, was that look, you spend 20, 30, 40 years building up that nest egg. I don't care what the number is whether it's one million, 5 million, 10, 12, at that point, you're not going to want to pull it down. It's going to feel bad seeing that number go down versus investing in cash-flowing assets that provide a return and then you're living off that cash flow.
Jeff: You can't tell me if you work for 40 years and all you do is save, save, invest, invest when you get to be 65 or whatever, you're just going to quit working and just start sucking the money off of there. To me, there's just no way that you can just automatically make that shift because it's been so ingrained in you.
I see it all the time from people like my dad's age. They're, "Why would I want to work in my whole life to get to the point where we don't want to travel because we've put off traveling. We don't want to do anything." I had a 76-year-old eye doctor that I treated two weeks ago. I treated him three years ago initially. I hadn't seen him in three years. He was 73 and now, he's 76. I saw him again. And I asked him, "Hey, are you still practicing?" He looked at me and said, "What else is there to do?"
The Passive Investor Circle

Jeff: I'm thinking, "God, I'd never want to get to that point where I have nothing else to do, but just this one thing." It's got to be just miserable. I encourage my kids. I'm trying to expose them to different parts of the country in the world and show them that there are other things in life to do besides just one thing. You only live once. That's got to be a miserable way to look at it to live. Again, that comes down to your mindset. A lot of times, what you've been taught you have to do versus again what we're teaching our kids. Just be cognizant of that.
Darin: Absolutely. Now, with the blog, you're getting people to reach out to you. You're building up a database of different people. What are you doing with that database of people that have reached out to you? I forget what you called it, the inner circle.
Jeff: Well, when I first started with the blog, the only email addresses that I would get are people that wanted to sign up to get the articles. That's it. As it started to grow, people would reach out to me and go, "Hey, Jeff, we're interested in maybe investing. We want to know a little bit more instead of just reading your articles about who you're investing with or can you teach us a little more."
I started with the passive investor circle. It's free. I know that's several people charge for. They always ask me, "Well what do you charge?" I said, "Well, you could pay me what you want, but I'm not going to charge you because I enjoy doing it."
Connecting With People and Creating the Circle
Jeff: That's for people that want to know a little bit more about what's involved with passively investing. Then, whenever I invest in something throughout the year, I'll put that deal out to people. If they want to invest in it with me, they can. If not, well at least they know some of the different investments that we're investing in.
Darin: How does that work? You have a doctor that signs up for that. Then you get a deal. You reach out to them, let them know you've got this deal. Are you guys forming an LLC and all investing together under that LLC? Or are you just introducing them to the sponsors? How is that taking place?
Jeff: Well, I was doing that up until last year. I had a group, Napali Capital, reach out to me, Dr. Tom Black. He's an ER doctor. He emailed me and said, "I saw your blog. I like the education that you're putting out. I just want to connect with you. Would you be interested in maybe educating our investors and maybe other people who may want to invest?"
I emailed him back. I said, "Are you the Tom Black that wrote The Passive Income Physician that I'm reading right now?" He was like, "Yes." I was like, "Are you stalking me on Amazon?" That was kind of a big joke that we had that it was just such a coincidence. I started connecting with them last year. Their company is just outside of Dallas. It's only a four-hour drive. I started meeting with them quarterly and got to really know them, got to tour a property with them. It was good because before, I was really just investing with two other sponsor groups.
Growing Network and Streams of Income
Jeff: But now, I could compare all three with their strengths and weaknesses. I really connected with them, maybe a lot of it because they really dealt a lot with other doctors. They cater to them. And they know what they're going through, their struggles and weaknesses, and that sort of thing.
Just a few months ago, they asked me to come on board to partner with their group to pretty much do what I'm still doing. Basically educating and sort of like relationships, investor relations having phone calls.
I love it because I'm able to see behind the scenes what you know as a general partner, everything that's involved with underwriting properties. They're underwriting 70 to 80 a month, and maybe acquiring four to five a year. These people that are treating patients and working, thinking that they're going to do that themselves on the side, it's now seeing what's involved. There's no way in my mind that you could do that to make it right with investors. There's a lot that goes to it.
Darin: Yes. There's a lot more involved than what you see just all of a sudden getting a PowerPoint saying, "Here's the deal." It's funny too with multifamily mentorship groups, I've talked to people where people reached out and said, "Darin, I want to get involved. I want to become a sponsor, but these multifamily mentorship groups charge a lot of money. I would join if they would guarantee me a deal."
I'm like, "Then don't join because you're still going to have to go out there and hustle." But it gives you the opportunity to meet a lot of people in the industry quickly. It probably shortens the time frame on getting from zero to one.
It Takes Time to Build Network and Streams of Income
Darin: Now, where do most of your relationships come from? Is it coming from in-state or is it coming from all over the country? Help me understand your presence with the blog and where your relationships are coming from?
Jeff: Well, I’ll take a step back, you got to realize when I started the blog, literally, the only thing that I knew how to do was get on the internet, and that's it. I had to teach myself. There are so many resources for free online that you could do, but I taught myself how to start a blog which wasn't hard.
Then, I took a course, I think, for 500 bucks which for the first probably four or five months, I was writing articles, but nobody was reading them. It's like, "What's the point?" Once I took that course and a lot of it just clicked with me about how to almost like finding the needles in the haystack. Because maybe take passive income, for instance. Well, if I try to write an article that ranks number one on the first page of Google on passive income, that's probably next to impossible because so many other huge websites are also competing.
You have to figure out, in the passive income, there's all these different keywords, phrases, and everything, but you got to find one where there's low competition. Then, once you rank with that up high, well then you can start ranking for other things. That was kind of the gist that they taught us on that course. I caught on pretty well. So I was able to rank number one after just a few weeks. I remember going to a convention and telling people that. They were just like, "We've been blogging for four or five years."
Consistency Is King

Jeff: We haven't even gotten on page one of Google. Again, once you start talking to them, they just don't really have a lot of good habits. They're not consistent with it. You just got to do that to be successful in life.
A pastor that I just recently heard that said, let's see, "Successful people do things consistently that most people do occasionally." I thought that was a great line. That goes with anything from athletics, to education, to building wealth, but if you get these habits and you do them consistently, then that's the difference between success or not. I just did that. It just really started to grow and take off. Now, that's able to get people from all over the country. I got people from India and the UK. The traffic that's taken off.
Darin: A few things that you said along your journey, look, you're a doctor. You built your own practice. And you could have just gone and worked for another practice. That was a risk. You've had a successful practice for 16 years. Then, you decided to take control of your financial assets. You invested in a deal. Then you got burned. You lost capital, but it didn't scare you off. And you continued to educate yourself.
When you did that, you realized, "Look, even though that first deal went bad, the wealthy 90% of millionaires are created with real estate. I'm going to continue down this path and continue to educate myself." You started to invest in these other syndications. They've performed well. Then, you wanted to start a blog and educate people. You didn't know how to do it. And you didn't know how to do it. You went and figured it out.
Have Faith in Yourself
Darin: Then, you paid for a course to help you. You thought through like, "Okay. Well, I'm writing a blog, but nobody's reading it. How can I get people to read it?" You took different action steps to change your situation which there's a lot of people out there that want to change their situation, but they either are unwilling or they're afraid to take the chance and learn and take action. I applaud you for making those efforts.
Jeff: Probably once a month, I'll have a call with somebody that they know as much or more about real estate than I do. They can spit off cap rates, you name it. I'm like, "Man, how many units are you invested in?" None. What do you mean? Well, I don't know. I think I'm over-analyzing everything. So I said, "How long have you been doing this?" I don't know, two, three, four years. And I said, "Look, you're going to call me in 10 years. I'm going to be beyond retirement. You're going to still be having this conversation. I'm still analyzing everything."
Sometimes, you have to put faith in yourself that you know what you're doing. I'm not talking about investing a million dollars. Do something small just to prove that you know what you're doing. You're going to fail, but then that's how you learn.
As long as you're progressing and not just completely going bankrupt, you're progressing, and you're doing it smartly. That's the only way to learn like when you learn to crawl. You didn't go from crawling to sprinting. You would walk a few steps. You'd fall. You'd figure it out. That's just life. Have some faith in yourself and put trust in yourself and go for it.
Streams of Income Includes Challenges
Darin: That's a great point. I've had people on here that have owned over 3000 units, 4000 units. When I met them, they were already successful. I thought they were always successful. But everybody starts with no investment properties. Everybody starts the same, with no experience, with zero units.
When I've had these interviews with them, I've asked them like, "Did you go to hero status right away?" Almost everyone shares a stumbling block, a failure, a painful investment. But just like yourself, they continued to learn and educate themselves and press on.
It doesn't mean that you have to lose your capital to have a failure. You don't have to have that happen. As I said, you're the first one that I've talked to that has actually lost their capital, but you may end up getting into a deal that doesn't perform as well as you thought. Then, you're going to say to yourself, "Well, what can I do differently next time?" Maybe, it's I'm going to invest in a different area or a different class of asset or a different sponsor, but whatever the case may be, to your point, that guy that's 10 years from now, he probably still will not have invested.
Jeff: Yup. That's true.
Darin: Jeff, what do you like to do outside of business?
Jeff: I'm a big reader. I like to work out, play a lot of tennis with my kids, basketball, a lot of sports. We travel a good bit. I love my Fridays off to really work on the blog and connect with people and educate people. To me, that's a lot of fun.
Next Big Stretch
Darin: What's the next big stretch goal for you?
Jeff: Well, hopefully, at some point, we'll get to start really getting out and meeting again. I like to meet face to face, do some talks instead of doing everything via Zoom or doing it virtually. I would really like to bring together several people that can really educate a lot of people at once whether it's from a tax standpoint, real estate standpoint, an attorney standpoint because as you know, you get into real estate. Well, there are tax benefits. You need some legal advice sometimes if you want to set up an LLC.
There are huge tax benefits, I'm not an accountant, that people could get. I'm sure there are different ways. Actually, for instance, I talked with an ophthalmologist that was in his fellowship last week. His wife was in real estate. She had been in real estate for a while. I was like, "Man, you are perfectly set up to eventually file real estate professional status." He really didn't know much about it. I said, "Man, that's going to save y'all hundreds of thousands of dollars in several years in taxes."
Just one phone call, I saved him no telling what, just from giving him that knowledge. There's so much that we can learn from other people. Why keep it to ourselves? I don't want anybody to take care of me. And I don’t want the government to take care of me. I want to do everything for myself, but I think the world would be a lot better place if we would all stick together and help each other. So I think that we can do that, just share what we know and continue to learn.
Passion to Help Others
Darin: That's huge. It sounds like that's something that's in your heart that you just have a passion for helping others and sharing with others. One idea is have you considered starting a meetup group in your area?
Jeff: I did, until everything kind of shut down last year. But I did talk with some people that did attend the meetup group. I'm in such a small area that there wasn't a whole lot of popularity. I may have to go to a larger city to do that, but, yes, that's definitely an opportunity to do that.
Darin: Fantastic. If somebody is listening here and wants to reach out to you, what's the best way for them to reach out to you?
Jeff: A couple of ways. They could go to the website. It's debtfreedr.com. If they want to download it, I put together a free passive income guide. They can go to debtfreedr.com/freeguide to download that. Also, they could email me, jeff@debtfreedr.com.
Darin: Fantastic. Well, Jeff, I really appreciate you coming on and sharing with others. I think it's important to hear from other people that aren't just syndicators who are doing thousands and thousands of units, but hearing the experiences of people that had a curiosity to learn how to take control of their finances and how to get involved in real estate from a passive side and now you're turning around and taking the education that you've learned and you're sharing it with others which is fantastic. I appreciate you coming on. Until next week, signing off.
How to Reach Dr. Jeff Anzalone
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