#140 He Built a Real Estate Portfolio on Autopilot | Chirag Chaudhari
He Built a Real Estate Portfolio on Autopilot (Chirag Chaudhari) reveals how a full-time physician scaled into real estate and built passive income without sacrificing his career. In this episode, Chirag breaks down his journey from small rental properties to large syndications, how he transitioned from active to passive investing, and why letting your money work for you is the key to long-term wealth. He also shares insights on due diligence, avoiding common investor mistakes, evaluating operators, leveraging AI for smarter decisions, and how compounding capital can dramatically accelerate financial freedom.
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Show Transcription:
As we’re learning, as we’re sort of doing our growth and getting educated, it’s doing that in a thoughtful way and sort of knowing the downside risks of anything that you’re getting involved in and knowing that everything has risks. The biggest aha moment was having the learning payoff and sort of getting into some of these opportunities and having a deal go full cycle and sort of gaining the benefits of the work you put in and the homework and some of that due diligence. While it’s important to do your due diligence and learn and if you want to do it at a level where you’re going to feel especially safe to do it at, yes, take courses, find a mentor, find a coach, all those things are invaluable. If they’ve done well, if they’re experts at their craft, they’re not going to necessarily brag about it, but it’s very clear in their track record just how well they’ve done, how serious they are and we get painfully into due diligence.
Tony Javier (00:49):
Welcome to the Real Estate Masters Podcast where we bring you the top real estate investors in the country. If you also want to be in the top 1%, you are in the right place. Listening to podcasts like this is exactly what helped me to scale my real estate investing business to seven figures, flip over a thousand houses and more importantly, step out of the operations of my business over a decade ago so I could start and grow other businesses. So get ready to learn from the best and start building a business that works for you and not the other way around. Enjoy.
Noah Kesslin (01:22):
Shrag, thank you so much for taking the time. I know you’re doing a ton of syndications in this space, but I am curious to kind of take a step backwards and kind of see how you got in real estate in the first place.
Chirag Chaudhari (01:33):
Yeah, no, sounds good. So yeah, I’m an emergency medicine doc out in Maryland by training. And so my wife and I were a little bit risk averse when it came to putting all of our retirement savings just into the typical 401k, 403Bs that now sort of refer to as money jail where it’s locked up and you don’t get to enjoy it until you’re almost too old to enjoy it in a lot of ways. And so what we did was anytime we had some spare cash lying around, we put it down as a down payment on a home. And so every few years it was something small, a townhome, a condo, but we’d save up enough to where we could buy sort of another home and that was going to be, in addition to the retirement plan, sort of live off some of that cash flow. And we got a healthy sort of active portfolio going after a decade or
Noah Kesslin (02:16):
So. Awesome. And then what was your life like before getting into investing?
Chirag Chaudhari (02:21):
Yeah, so really I went straight through. I didn’t take time off for a lot of things. Kind of did high school, college, went straight into medical school and sort of gap years weren’t in vogue at the time. And so for med school, went straight into residency and so became an attending and did my emergency medicine residency out in Baltimore, University of Maryland and I’ve sort of stayed put ever since in one of their community hospitals. So not super exciting from that standpoint, but waited a really, really long time before I had disposable income to speak of because the training and the education is a little bit absurd and long and so you sort of pay that back for a long time.
Noah Kesslin (02:58):
Yeah, for sure. And then for the people listening, what does your business look like today? What does the investing portion look like today?
Chirag Chaudhari (03:05):
Yeah. So today definitely still have a little bit of an active portfolio and enjoy that. And again, the properties that we’ve sort of had, they’ve been paid off over a decade plus now by folks that live there by our tenants, which is great. We had a ton of equity in them. And so we 1031 a couple of the properties actually from long-term rentals into short-term rentals down in Florida. And so we’re doing a couple of Airbnbs down there and those have been really great. Each one of them has probably 10X the cashflow that it was doing as a long-term rental, which is great. And again, it’s with that same initial sort of down payment. We haven’t put a whole lot more in there. I think as you talk about the ability to grow your wealth through real estate and it really just kind of compounds the longer you’re sort of in the game so to speak. And then we said, look, we have a lot of active portfolios. It is time. There is considerable sort of management. And even if you have property managers, you’ve got to manage the managers. And so we said, look, let’s step back and get a little bit more passive. And probably since 21, we’ve been doing a ton of passive real estate and syndications and lots of different asset classes so that we’re appropriately diversified. But yeah, that’s been great. It’s sort of let us be sort of hands off.
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Noah Kesslin (04:58):
What was the main problem that you were trying to solve professionally or personally when getting into real estate?
Chirag Chaudhari (05:07):
I think as most professionals, we get in sort of the habit of trading hours for dollars and we’re like, “Ah, we’ve got this vacation. I’m just going to pull an extra shift or I’ll put in some extra hours. I’ll grab some overtime and we’ll be able to cover it. ” And so much of the time we’re creating extra time or taking away extra time from ourselves so that we can sort of make that purchase or have that nice dinner, whatever it was. And I sort of wanted to do that passively and have my money work for me as opposed to me work for my money because hopefully folks are at a place where they’ve made some and they’re able to have that sort of work for them. And so passively being able to do things as long as you vet them appropriately, not saying it’s a magic bullet or anything, but you’ve got to put a little bit of work, but the amount of effort, the amount of work is very asymmetric to your returns to where very little work can yield pretty amazing returns comparable to active real estate,
Noah Kesslin (05:59):
For sure. Why do you think so many people overlook that piece and not put extra cash into something like real estate?
Chirag Chaudhari (06:08):
Yeah. I think a lot of times people hear stories and they hear stories of, “Oh yeah, I had a friend who invested in something and they lost it all and it happens. 100% it happens. It’s happened to me. ” And so I think it’s as we’re learning, as we’re sort of doing our growth and getting educated, it’s doing that in a thoughtful way and sort of knowing the downside risks of anything that you’re getting involved in and knowing that everything has risk. Nothing’s risk-free, the stock market’s not risk-free. It changes dramatically day by day for those that follow it closely. And so I think it’s sort of anxiety, hearing stories and maybe not wanting to learn as much as you could or not having the time or the bandwidth to really dig into any one particular topic and learn it sort of soup to nuts.
Noah Kesslin (06:55):
What’s been the biggest aha moment that you’ve had since getting into real estate and what’s been the biggest lesson since getting into real estate?
Chirag Chaudhari (07:05):
I think the biggest aha moment was having the learning payoff and sort of getting into some of these opportunities and having a deal go full cycle and sort of gaining the benefits of the work you put in and the homework and some of that due diligence. I think that was you know it’s working and that it happens frequently. And my wife and I are just to sort of set the stage, we’re in 25 of these syndications as just investors, as limited partners. And so every month, every couple of months there’s checks coming in and we’re doing nothing for those checks. We’re just sort of waiting patiently, which is great. So I think that’s the aha moment of saying, “Hey, we really sort of didn’t work for this money.” Our money’s kind of working for us, which is great. And then I miss the second part of your question. I’m sorry.
Noah Kesslin (07:57):
No, it’s just the aha moment and then the biggest thing that you’ve come to realize that you didn’t really know before getting into real estate.
Chirag Chaudhari (08:09):
Yeah. I think honestly, I didn’t have an appreciation initially for sort of the fact that my initial commitment would compound so quickly and I didn’t have to do a whole lot more. Yes, there’s time involved, especially on the active side, but as far as capital goes, once you deploy that capital, it continues to grow and it grows exponentially and far faster than it would in the typical market, if you would, or in the stock market, or if you’ve got bonds or anything else that the potential to grow that much quicker is there in real estate and sort of different real estate asset classes.
Noah Kesslin (08:43):
Yeah. Well, what do you think the most common misconception is about what you do in real estate?
Chirag Chaudhari (08:51):
Yeah, I think it’s the fact that you need to know everything about it before you sort of go in. I think while it’s important to do your due diligence and learn and if you want to do it at a level where you’re going to feel especially safe to do it at, yes, take courses, find a mentor, find a coach, all those things are invaluable. But being a physician, I work with a lot of other physicians that love what they do. They do not want to take time away from their patients. They do not want to take time away from their practice because they love it and they instead want to find somebody that they trust that has done the work that they know is doing the due diligence and they just want to invest alongside those folks. And so that’s another way to do it is just to find folks that are doing it, look at their track record, make sure they’re educated, they know what they’re talking about and do the same thing they are. Tiger 21 is sort of how they invest. It’s the ultra, ultra wealthy, if you will, of the world. And you look at their asset classes that they’re investing in and the full almost 25% is real estate investments. And so I think it’s just copying what they’re investing in, copying what others are doing is a great way to go.
Noah Kesslin (10:01):
Yeah, 100%. Well, one question I have for you, speaking of marketing, where are you finding most of your syndications right now?
Chirag Chaudhari (10:09):
So a lot of times what we’ve done is we’ve been able to sort of bring large amounts of capital to sponsors. And so we’re at a point now where really great sponsors are actually reaching out to us and asking us to partner with them because they know we’re able to bring in several million dollars per deal. And so that deal flow has been tremendous. I’m also a part of several different masterminds. And so we meet people through those communities, sort of abundance-minded folks that are like- minded and want to put together really nice opportunities for our colleagues, our friends, our family members. And so it’s been a really great way to connect with partners.
Noah Kesslin (10:48):
Yeah. And then of course being in the doctor space, I’m sure there’s a lot of people with money to invest. Where are you finding most of your investors? Where are you finding them?
Chirag Chaudhari (11:01):
I think most of the time, honestly, it’s just friends of family and colleagues. We tend to partner with a lot of other physicians and they will sometimes reach out and hear about our deals. They’ll get in, they’ll get some of the returns and they’ll say, “Hey, I want to bring some friends.” And we’re like, “Great.” And so that’s sort of how it started, very grassroots. And I was doing this and people were like, “Hey, what are you investing in? ” And I’d tell them who and what deals and they would jump in too. And I said, once we got 10, 15, 20 of us together, I was like, “We can probably get better terms.” And so then we would go to the sponsors and say, “Hey, look, we’ll invest two million, three million, four million, whatever it is. Can you get us nicer terms as a result?” And so a lot of times we’re able to get much better terms for all of us collectively, power in numbers, so to speak, and better returns, which it’s been great.
Noah Kesslin (11:50):
I love that. What mistakes do you often see investors make in the syndication space that you think could be really easily avoided?
Chirag Chaudhari (12:00):
Yeah, I think it’s phone a friend, I would say. If you’re looking at a deal and the numbers look great and everyone has fancy pitch decks and they’re throwing them into AI and making them look all sorts of sizzle stats here and there and a lot of them are real, but a lot of them are sort of, you got to look past the numbers a little bit. You got to vet the operator and you vet the deal. And so really important we always say bet on the jockey, not the horse. And if you’ve got a good operator, they can take a bad deal and still make it do okay. Whereas if it’s a poor operator, even a deal, a really great deal in a poor operator’s hand sometimes doesn’t go well. And so it’s real important. We do our own due diligence. We set up our own sort of risk sensitivity tables and things like that and always looking at downside. The upside’s great, but we want to make sure that we take into account sort of worst case scenario. And I think a lot of times people don’t look at that. They sort of give it surface value interpretation and say, “These numbers look great. It goes along with my investment thesis. I’m going to go in. ” But I would say just have somebody else look at it and help you see the blind spots maybe that you’re not seeing.
Noah Kesslin (13:09):
Yeah, for sure. What do you think separates top operators from everyone else in your experience?
Chirag Chaudhari (13:16):
Honestly, so much of it is track record. We always say past performance doesn’t dictate future performance, but so much of it is track record. I think if they’ve done well, if they’re experts at their craft, they’re not going to necessarily brag about it, but it’s very clear in their track record just how well they’ve done, how serious they are and we get painfully into due diligence. The people we work with, they said, “We’ve never been asked this many questions. No investor ever gets into this level of detail, but we’re bringing in, again, anywhere from Forda, we brought in 23 million into one deal. And so sometimes these are large sums of money and we do criminal background checks on them and the analysis is deep. And so I think it’s really honing in on the fact that they’re willing to share. If there’s any hint of not being transparent or not wanting to answer a particular question, that’s a giant red flag for us and not somebody we would work with.
Noah Kesslin (14:13):
Yeah. What’s the biggest challenge you’re seeing in real estate in general right now?
Chirag Chaudhari (14:20):
I think it’s investor sentiment, honestly. I think people are a little bit spooked just given, especially multifamily, let’s say it’s had a rough couple of years with the interest rates spikes that happened. A lot of deals that penciled a few years ago no longer pencil and people are getting rate caps and purchasing those, but a lot of deals are stressed and are distressed and are selling for much lower than what they should be selling for. And I think those investors are probably not going to do well overall. And so they’re reluctant to maybe jump into something else. And as Warren Buffet famously says, be greedy when others are fearful. And so it really is a really great time for people to sort of get in the market and do that work. But I think you’ve got to overcome some of that investor sentiment and just being fearful to know that we’re in sort of a trajectory where we’re going to be seeing some really tremendous growth.
Noah Kesslin (15:23):
Yeah. You mentioned AI earlier. How do you see technology, AI specifically affecting the real estate market and how do you think it’s going to move and shape the next five years?
Chirag Chaudhari (15:38):
Yeah, I think it’s great for a lot of reasons. And I think some of the expectations need to be tempered because we can’t trust everything that it’s sort of putting out there. But I think in terms of from the investor side, looking at material and looking at some of these private placement memorandums, these PPMs can be hundreds of pages sometimes and it’s all in legalese. So I think to interpret that and put it into AI and say,” Hey, give me a list of 10 questions to ask. What are the red flags in this document? “Same thing with pitch decks and things like that. I think for investors, it can digest that very quickly and give you very good fundamental questions to ask, especially if you’re just learning. It’s a great way to learn and AI can obviously teach if there’s anything that’s of question, putting that in is great. Underwriting is phenomenal. It’s really good at doing market analysis and looking at areas and analyzing sort of risk points to underwriting. Always need a human eye to go over it, but it can at least focus you on the things to look at. So in that sense, it’s made light of some of that work.
Noah Kesslin (16:49):
Yeah, 100%. The word success to me is very interesting. I feel like a lot of people define it differently. They look at it differently, they measure it differently. How do you define the word success in your life? How do you measure it and how do you strive for it every day?
Chirag Chaudhari (17:06):
I think I subscribe to a little bit of the 1% better every day and sort of always motivating to do the next thing. There’s a quote that I really like, which is action delayed is greatness betrayed. And so I think so many people get stuck in sort of analysis paralysis and they pause and they’re like, ” Next year I’m going to do this. Do it now. Why wait? Why are we waiting for next month? Why are we waiting for next quarter? If it can be done, do it. If you think it’s going to increase your trajectory of what you’re doing, there’s no reason to pause, just do it, honestly. And if you’re going to fail, fail fast, brush yourself off, get up, you’re going to learn from that tremendously and you move on. But again, I strongly believe in phoning a friend and having a network of people around you that are going to support you in all of your efforts. It’s funny. I was at a conference just a week ago, a real estate conference, best ever conference in Salt Lake City and it was great. They’ve got booths and people to talk to and there was a self-publishing booth and they’re like, “Ah, you ever want to write a book?” I was like, “Yeah, that could be neat.” They’re like, “Yeah, we’ll get you set up. You’ll be a bestselling author in 18 months.” I was like, “That sounds amazing. Sign me up.” And so I don’t know the first thing about writing a book, but I’m going to be writing a book. And again, it’s one of those just do. It’s something that I don’t know that it defines success because I have a book. It’s just success to me is always growing, always learning, being a perpetual student and that fills my cup and brings me tremendous joy.
Noah Kesslin (18:39):
I love that. I love that. Well, let’s say you were going to start from scratch. The properties that you have, the business syndications, everything goes away. You get to keep all the knowledge that you’ve learned over the years. If you were going to try and get back to where you are now, what would you focus on first?
Chirag Chaudhari (19:00):
It’s a really good question. Yeah, I think given everything that I’ve done and learned, I would say honestly, I would probably focus on doing more of the passive because it’s a quicker wealth builder than the active real estate. And so as long as you do it intelligently, there’s ways to do it non-intelligently, but there are opportunities out there that can rapidly multiply capital very quickly if that’s what folks are looking for depending some people want to go a little bit safer and just have more of a long stretch and then active makes sense. But I think most of the folks that I talk to now are looking for sort of shortholds, rapid multiples of their equity and passive I think is probably a quicker path to getting there.
Noah Kesslin (19:47):
Yeah, I love that. Who has been the biggest influence for you in this space?
Chirag Chaudhari (19:52):
Honestly, it’s been some of the masterminds that I’ve been in and those have been great. I belong to a couple of different physician masterminds and I took a course Zero to Freedom is the name of the course and that’s put on by Kenji and Leiti and that’s more on the active real estate side, but it taught me how to 1031 my long-term rentals into Airbnbs. It taught me how to go from sort of being a limited partner to the general partner side of things and helping to actually put on these opportunities for other investors and negotiate better terms from sponsors. And then Raise Masters is another one, which is with Hunter Thompson’s group to sort of learn the art of putting together these deals and syndications and talking to SEC attorneys and CPAs about some of the intricacies involved. I would say probably those are probably what grew me the quickest and the fastest.
Noah Kesslin (20:45):
Yeah. Awesome. Awesome. If someone is interested in syndications, maybe they have extra money laying around that they want to invest or they’re just interested in it in general, where can someone reach out to you? Where can they find you? If someone’s interested in working with you, where can they go?
Chirag Chaudhari (21:02):
Yeah, so my website is thesyndicationdoctor.com and my email, if that’s easier, is thesyndicationdoctor@gmail.com.
Noah Kesslin (21:11):
Awesome. Awesome. I love it. Well, I really appreciate you coming on with us today and being here and taking the time. Any final advice for any investor or just person in general that’s looking to grow their wealth?
Chirag Chaudhari (21:27):
Yeah, I think honestly, I think there’s so many folks out there trying to do similar things. I would say just find somebody who has your best interest at heart and wants to help you grow and they’ll point you in directions of books and conferences and mentors and people that are going to help you grow because definitely don’t do it on your own. Don’t try to learn by yourself. There’s a whole army of folks out there that’ll help you, but congratulations on starting that journey.
Noah Kesslin (21:55):
Awesome. Awesome. I love it. Thank you so much again for taking the time and we’ll see you next time, guys.
Chirag Chaudhari (22:01):
Thanks for having me. Yes, Sir.



