Dr. Chirag Chaudhari’s investing origin story is one that resonates with nearly every high-income professional. He bought a home during residency, lived in it for three years, and when he sold it, the profit exceeded his entire residency salary. That single transaction planted a seed. Over the next decade, every time a bonus check arrived and the family had enough for a down payment, they bought another property – condos, townhomes, small rental homes. Within 12 years, they had five or six properties generating cash flow.

But the classic landlord grind eventually wore thin. Chaudhari found himself wanting the wealth-building benefits of real estate without the active management burden. That tension – loving the asset class but hating the time commitment – is the exact inflection point where many physicians pivot toward passive investing through syndications. Rather than going it alone, Chaudhari accelerated the learning curve by joining masterminds, hiring coaches, and compressing five years of education into roughly one year. Friends and colleagues noticed what he was doing, asked questions, and eventually wanted in. What started as informal conversations turned into a structured capital aggregation model.

What You’ll Learn

  1. How an ER physician built a portfolio of 25 syndications across multifamily, land, short-term rentals, oil and gas, and energy while still practicing medicine full time
  2. Why Dr. Chaudhari calls traditional retirement accounts “money jail” and the specific mechanics of taking a 401k loan to invest in syndications without early disbursement penalties
  3. The three ways physicians can offset active W-2 income: the short-term rental tax loophole, real estate professional status through a spouse, and energy investments subsidized by federal credits
  4. How pooling physician capital into a single SPV allows the group to negotiate most favored nation status, higher pref rates, bigger profit splits, and advisory board seats
  5. Why a three-to-four-month due diligence process that includes criminal background checks and independent market analysis protects investor capital at scale
  6. The reason land syndications with no leverage and three-to-five-X equity multiples have become a favorite low-risk play in the current cycle
  7. Why data center infrastructure, alternative energy, and AI-adjacent land may be the next major opportunity for passive investors over the next five to ten years
  8. How the barbell investing mindset – spreading minimums across many deals instead of concentrating in one – creates a safer overall portfolio even if a couple of investments go to zero

Memorable Moments

  1. When discussing the weight of responsibility that comes with deploying other people’s capital, Chaudhari offered a perspective that reframes how investors should think about their money:

“We don’t think of it as money that we’re taking from investors. That is their hopes and dreams. What they do with that at the end of that deal is going to be college education for children. It’s going to be the best anniversary vacation ever. Those things are earmarked for a very specific purpose. And we take all of that very, very seriously.” – Dr. Chirag Chaudhari

  1. On the non-negotiable standard for transparency with operators:

“If ever anything would stop us from working with someone, it’s ‘I don’t know if I can answer that,’ then we’re done. There’s always an answer. We don’t have to like the answer, but there always has to be an answer. And if there’s any lack of transparency – giant red flag.” – Dr. Chirag Chaudhari

On the importance of having a seat at the table when large amounts of capital are at stake:

“If you’re not in the room, you’re sort of on the menu. And so we love to be in the room.” – Dr. Chirag Chaudhari

On the relationship between emergency medicine and investor advocacy:

“In emergency medicine, you’re always trying to advocate for the patient and get the best thing that you can for them. I think that does correlate really well to advocating for your investors.” – Dr. Chirag Chaudhari

Resources & Links Mentioned

Disclosure: Some links below may be affiliate links. We may earn a commission at no cost to you. As an Amazon Associate I earn from qualifying purchases.

  1. The Syndication Doctor (Dr. Chirag Chaudhari’s website)
  2. The Syndication Doctor email – thesyndicationdoctor@gmail.com
  3. Antifragile by Nassim Nicholas Taleb
  4. Truly Passive Income Passive Investor Toolkit
  5. Nomad Capital (Neil Henderson and Clint Harris’s investment firm)

Timestamps

[00:00] – Introduction to Dr. Chirag Chaudhari

[02:18] – From residency home sale to real estate

[04:45] – Active vs. passive ownership for doctors

[07:30] – ER skills that transfer to investing

[10:15] – Building a physician investor community

[13:42] – Due diligence and vetting sponsors

[16:50] – Money jail and rethinking retirement

[20:05] – Depreciation strategies for physicians

[23:30] – Negotiating terms as a capital aggregator

[26:45] – Advisory board positions explained

[29:10] – AI, data centers, and future asset classes

[32:00] – Best resource advice and closing thoughts

About the Guest

Dr. Chirag Chaudhari is a board-certified emergency medicine physician with 24 years of attending experience, currently practicing at a hospital outside Baltimore, Maryland. He is the founder of The Syndication Doctor, a platform that helps physicians and high-net-worth individuals invest passively in real estate and alternative assets. As both a general partner and limited partner in over 20 syndication deals, he has built a physician investor community that aggregates capital to negotiate preferred terms across multifamily, land, short-term rentals, oil and gas, and energy investments.

Website: https://thesyndicationdoctor.com

Email: thesyndicationdoctor@gmail.com

Call to Action

Ready to start building passive income outside of your retirement accounts? Download the free Passive Investor Toolkit at https://trulypassiveincome.com/toolkit/ – it is the same resource we recommend to physicians, executives, and high-income professionals who are evaluating their first syndication investment.

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Transcript
Speaker A:

And so you know what I tell people in the market and love the market and are like, there's nothing wrong with the market.

Speaker A:

I think it's fine.

Speaker A:

It's a good place to put your money.

Speaker A:

It's safe.

Speaker A:

And if you look over historical numbers, you're going to do 8% a year typically.

Speaker A:

Right.

Speaker A:

For over the long term, these syndications, if you get into good ones, are in their 20s.

Speaker A:

Right.

Speaker A:

The opportunity to sort of amplify returns is really concentrated in some of these opportunities.

Speaker A:

For example, we do some land ones which are great.

Speaker A:

There's no leverage, we buy in in cash.

Speaker A:

There's really no downside risk outside of time to sort of rezone and then resell that land.

Speaker A:

There's not a lot of advantage.

Speaker A:

You know, you're not going to get depreciation.

Speaker A:

You're buying dirt.

Speaker A:

Dirt's not depreciating.

Speaker A:

You're not, you know, there's not a whole lot of tax advantages, but you make 3-5x, you know, multiples on your, on your initial capital outlay.

Speaker B:

Welcome to Truly Passive Income.

Speaker B:

I'm Neal Henderson.

Speaker C:

And I'm Clint Harris.

Speaker C:

And today we are interviewing Dr. Chirag Choudhury.

Speaker C:

He's an emergency medicine physician who built a diversified investment platform spanning short term rentals, multifamily land syndications, oil and gas, pref equity and more.

Speaker C:

As both a GP and an LP in over 20 deals, he applies clinical decision making, systems thinking and risk management from the ER to capital allocation.

Speaker C:

He's helping physicians move beyond money jail retirement plans and into thoughtful cross asset investing that creates cash flow, tax efficiency and long term wealth for their families.

Speaker C:

Super excited to have you here sir.

Speaker C:

How are you today?

Speaker A:

Doing great and thank you so much both Neil and Clint for having me.

Speaker A:

Really appreciate it.

Speaker C:

Absolutely.

Speaker C:

We're excited to jump in.

Speaker C:

I, I've said this on the podcast many times but, and I've said to you before we started recording, but I always really look forward to these interviews where we have white coat professional that has that the mentality, especially in the ER of being able to triage and look at things through a system and a process and move them through where they need to go and make that jump to also having the business and financial acumen side of things.

Speaker C:

And a lot of times you can see those same skill sets applied in a methodical way that really helps get results.

Speaker C:

And so I love these conversations and I'm excited about it today.

Speaker C:

Why don't you give us a little bit of background about where you are in terms of Your medical background, how you made the transition into real estate and then we'll quickly try to start moving to some of the assets you've invested in.

Speaker A:

Sure, yeah, no, sounds good.

Speaker A:

So yeah, I've been what we call in medicine PGY, sort of, you know, 24, which means I'm a postgraduate year.

Speaker A:

24.

Speaker A:

So I finished residency 24 years ago, been attending for, for that period of time and it's been great and love emergency medicine.

Speaker A:

Would do emergency medicine all over again if I had the choice.

Speaker A:

It's been, and it is a tremendous career.

Speaker A:

Still practicing do about a shift a week in the ER now and so.

Speaker A:

But it's great.

Speaker A:

It's, you know, wouldn't change that for a thing.

Speaker A:

Always have had sort of interest in real estate when it came to sort of selling our first home.

Speaker A:

We bought a home in residency.

Speaker A:

That was our first sort of purchase and, and that was three years that we sort of lived in that home, welcomed our children in there and then sold it when we moved to a little bit, you know, further south from where we were, but made more on the sale of that home than I did in three years of residency.

Speaker A:

And so, you know, if that wasn't a sign that real estate was, you know, a wealth creating vehicle, I don't know what was.

Speaker A:

And so it was a period of time before we could get back into it.

Speaker A:

But then, you know, anytime I get a bonus and we had enough saved up for a down payment, we bought a home.

Speaker A:

And so, you know, within 10, 12 years we had five, six homes, small, you know, condos, townhomes, but that was sort of the retirement plan.

Speaker A:

Just live off that cash flow and.

Speaker A:

And then in later years, you know, really started thinking more thoughtfully about, you know, not wanting to sort of be a landlord, not wanting to do the active work and you know, gosh, if I could only get some of the benefits that I've seen in real estate, but sort of not have to do a lot of the work and get passive income from it and so sort of tilted that way a little bit, which I think really resonates with a lot of sort of high income earners that love what they do, love their profession, yet want some additional, you know, passive streams of income on the side.

Speaker C:

I love that.

Speaker C:

Yeah, at the end of the day you're still trading time for money and eventually when you get to a point where you don't want to get up and get out of bed, that's not the day you worry about that.

Speaker C:

Right.

Speaker C:

You got to build that off ramp For a life that you still have capital that's getting up out of bed and going to work, even when you decide that you don't want to.

Speaker C:

You.

Speaker C:

There's a lot of similarities about your pathway of, of, you know, identifying real estate.

Speaker C:

You had that light bulb moment.

Speaker C:

You saw the numbers from your.

Speaker C:

Your first property that got you into real estate.

Speaker C:

And then you get to the point, especially having kids in your career, you're like, you know what my time is actually worth more than anything else?

Speaker C:

How do I make a shift where I continue to invest in real estate, but without investing as much of my time and becoming an accidental landlord?

Speaker C:

And a lot of times that's where we see people make the transition to become a limited partner or general partner.

Speaker C:

And you're looking at syndication, where it's a group of people pooling capital together to execute a business plan larger than what any individual could probably do on their own.

Speaker C:

One thing that's interesting about you is that you've invested both as a GP and an lp, and a lot of times what we see with physicians is that you have to have three things to have success in real estate investing.

Speaker C:

It's time, it's experience, and it's money.

Speaker C:

What you guys traditionally do not have a lot of is time.

Speaker C:

Without time, you can't get experience.

Speaker C:

Now you were building experience through your.

Speaker C:

Your individual investments, but it's really hard to take that to the next level.

Speaker C:

So the natural transition we see is a lot of times people start exploring and investing as a limited partner, but you've done it as a limited partner and as a general partner, which oftentimes requires more of a time investment.

Speaker C:

So I'm curious to know what capacity you did that in.

Speaker C:

Was it pooling other physicians together to raise capital?

Speaker C:

Was it actually executing a business plan?

Speaker C:

What does that look for you as you've delved into the world of alternative investments?

Speaker A:

Yeah, so I think really great question.

Speaker A:

You're spot on.

Speaker A:

I think, you know, that that sort of key element there is time.

Speaker A:

Right?

Speaker A:

And.

Speaker A:

And what do you do with that time?

Speaker A:

And I know I've had a strong interest in, you know, the sphere of real estate.

Speaker A:

And so I went deep.

Speaker A:

I did multiple courses, joined multiple masterminds, got mentors, got coaches that could sort of, you know, be able to amplify the speed of what I was able to do and shrink what would have taken me five years into, you know, one year.

Speaker A:

And so I think from being able to do that, you know, it was really helpful in my journey and then really started to Learn about how to vet a sponsor, how to vet a deal.

Speaker A:

You know, what is it sort of that downside risk that I need to be thoughtful about and aware of.

Speaker A:

And then I had friends, you know, just sort of seeing what I was doing, saying, hey, you know, what are you, what are you investing in?

Speaker A:

Why do you think that's good?

Speaker A:

And so we talk it through and, you know, they trusted me.

Speaker A:

They knew I was putting my funds into it.

Speaker A:

And they're like, all right, fine, we're going to come in too.

Speaker A:

I was like, great, you know, we'll all do well.

Speaker A:

And that started growing.

Speaker A:

And then folks were, you know, I, I said, look, if we're going to, you know, if there's enough interest here where we're putting in significant amounts of capital, there's no reason we shouldn't all go in together, right?

Speaker A:

And we can get, you know, better terms and power in numbers.

Speaker A:

We can get, you know, whether it be a higher profit split or a higher pref rate or whatever it is by us doing it together collectively, that would be, you know, beneficial to all of us as investors when we come in.

Speaker A:

And so that's sort of what we started doing.

Speaker A:

And it's been, it's been great.

Speaker A:

It's been a lot of time and sort of developing those relationships.

Speaker A:

But, you know, it, it's paid off in the end.

Speaker B:

I'm curious, working in the white coat community, what sort of advice you have for other white coat professionals who may be looking at real estate around balancing pursuing active ownership of real estate versus keeping the main thing.

Speaker B:

The main thing, you know, I mean, time is, is your most precious resource.

Speaker B:

And we often see it with people, it's like, oh, you see somebody doing really well in short term rentals or long term rentals, whatever, and see, so I'm going to buy the, I'm going to buy one.

Speaker B:

Whereas, you know, maybe you might have been better off trying to go the LP route, you know, versus direct ownership.

Speaker B:

Do you ever have sort of advice that you give for medical professionals on that front?

Speaker A:

Yeah, you know, I think, you know, direct ownership is a great way for wealth creation.

Speaker A:

It's a long play, right?

Speaker A:

It's not something that you're gonna see very quickly.

Speaker A:

It's something you're gonna be vested in for a good period of time.

Speaker A:

And then you scale using 10, 31 and other vehicles to help you sort of grow, you know, sort of push off taxes as long as you can.

Speaker A:

And there's a lot of advantage to active ownership.

Speaker A:

We have a, you know, active portfolio.

Speaker A:

We have short term rentals that we do.

Speaker A:

And, and I, and I do think that should be a piece of everyone's portfolio if they have the time and the interest to do it.

Speaker A:

The key being the time and the interest.

Speaker A:

Because it's a large amount of time, it's a large amount of interest to sort of be able to do those things thoughtfully.

Speaker A:

For those that don't have the time or interest, I think passive is 100% the way to go.

Speaker A:

You get very much of the similar benefits in a much concentrated, shortened time frame for most of these deals.

Speaker A:

As long as you know, you're thoughtful about who you're investing with, you've done your homework and your due diligence and all of those things are critically important because you don't want to put your hard earned dollars at risk ever.

Speaker A:

Right?

Speaker C:

Yeah.

Speaker C:

Neil mentions all the time he calls that money.

Speaker C:

It's, it's a representation of your store of life energy, right.

Speaker C:

That's a representation of time that you likely spent away from people you love doing things you probably want to would not have been choosing to do of everything you could do in your life right then if you weren't getting paid for it.

Speaker C:

So you've got to protect that.

Speaker C:

Right.

Speaker C:

It's a representation of time that you've given up.

Speaker C:

I have a question for you that I'm now, in retrospect, I'm surprised I haven't asked this before, but as an ER physician, do you think across the, the community of physicians, dentists, surgeons, EPs, cardiologists, whatever it may be.

Speaker C:

I'm just thinking about this from your standpoint.

Speaker C:

Do you think that it's, it's easier or better for some physicians to, to lean into this and learn and get involved more so than others?

Speaker C:

Like it seems to me as an ER doctor, a lot of what you're dealing with is you're triaging problems that are coming through and you're getting those people through to where they need to go to get healing.

Speaker C:

And it's, every day is going to be different and it's fast paced and it's moving, but then the continued ongoing care and complexity sometimes is getting passed off to other people.

Speaker C:

Do you think that that is it pretty much across the board that hey, you're a physician, you're, you're working on RVUs, you're working for a hospital system, you have to practice some defensive medicine sometimes because sometimes things are administratively heavy.

Speaker C:

It's the same challenge for everybody.

Speaker C:

Figure it out.

Speaker C:

Or do you feel like because of your profession that it's given you opportunity to pursue that.

Speaker C:

And that is something that maybe was attracted to the other people in your community where they saw what you were doing and they were kind of able to come together with you and that there's power of community there.

Speaker C:

Or do you think it's pretty much across the board for all physicians?

Speaker C:

I'm asking just from your perspective as a doctor.

Speaker A:

Yeah.

Speaker A:

So I think that's a really unique question.

Speaker A:

I will say sort of in our masterminds and in our groups, there are physicians from all over the house of medicines.

Speaker A:

We've got cardiothoracic surgeons, we've got nephrologists and pathologists and obgyns, and you name it, they're psychiatrists.

Speaker A:

Right.

Speaker A:

They're in our group.

Speaker A:

And we will capital raise together.

Speaker A:

So I think there's interest with no matter sort of what part of the house of medicine you belong to.

Speaker A:

And we've got attorneys and dentists and economists.

Speaker A:

And so there's other sort of other specialties out there.

Speaker A:

I'll say the one thing that's unique about emergency medicine is we don't have the benefit of ever calling somebody to just say, hello, right.

Speaker A:

We're calling a cardiac thoracic surgeon.

Speaker A:

It's to give them work, right.

Speaker A:

And we're like, hey, I got a patient, I've got.

Speaker A:

And so you're, you know, they say real estate's about location, location, location.

Speaker A:

And it is to an extent, will not disagree, but I think more important than that, it's about relationship, relationship, relationship.

Speaker A:

Right.

Speaker A:

We are in the business of relationships, of being able to speak to one another.

Speaker A:

And I think in emergency medicine you're always trying to advocate for the patient and get the best thing that you can for them.

Speaker A:

And you're making these calls to, you know, all sorts of different specialties and advocating for the patient.

Speaker A:

And then so I think that does correlate really well to advocating for your investors.

Speaker A:

I think there's no difference.

Speaker A:

I think everything we do, just like in medicine, as in real estate, it's a risk benefit discussion, you know, and we're, we're, if anything, on the risk averse side.

Speaker A:

We're not taking risks.

Speaker A:

We're not sort of being flagrant.

Speaker A:

And you know, this isn't sort of private equity and, you know, angel investing and some of the other things that you get into where that risk reward is really high.

Speaker A:

We don't want that.

Speaker A:

You know, that's not what we're looking for.

Speaker A:

We're not looking to increase risk.

Speaker A:

We're Looking to decrease risk and, and build that wealth over a long time.

Speaker A:

So I think, I think that gives us kind of a unique perspective.

Speaker C:

Yeah, completely.

Speaker C:

I want to dig into the relationship side even a little bit more.

Speaker C:

So Neil and I are partners with Nomad Capital.

Speaker C:

Our strategy is we buy old vacant big box buildings like Kmarts and grocery stores that have been empty for years and we use our construction team to convert those into climate controlled storage.

Speaker C:

It's not rocket surgery, right, to obviously

Speaker B:

mix your metaphors there a little bit.

Speaker C:

Well, on purpose.

Speaker C:

Right.

Speaker C:

I'm not, I'm being a little bit flippant, like it's not, it's not the hardest thing in the world.

Speaker C:

We take a big box, we chop it up into a bunch of little boxes and that's it.

Speaker C:

But it does require a level of investor education.

Speaker C:

And a lot of times we want to put, everybody should, especially the investor, should be putting in the effort up front to build the relationship.

Speaker C:

I know you talk about betting on the jockey and not the horse, and that's very much what it is.

Speaker C:

Who are you going into business with?

Speaker C:

What does the project look like?

Speaker C:

What does the offer memorandum look like?

Speaker C:

What's the projections, what's the track record, everything else associated with that.

Speaker C:

And because of that, going through that educational process and explaining to people what our strategy is, our recapitalization and everything else, I've really come to value the power of community.

Speaker C:

When underwriting deals, when looking at operators, one group with a hundred set of eyes on something is going to bring up questions, challenges, objections to navigate that 100 people individually likely are not going to come up with.

Speaker C:

There may be, there's going to be one or two people that collectively are going to ask those questions.

Speaker C:

But when you bring everybody together, I really believe in the power of community because we have the ability to do that in a better way than the world has ever seen.

Speaker C:

But also it's going to allow you to get down to the root of what the offering is, who the operator is, and if it fits and aligns with your goals.

Speaker C:

So honestly, this is kind of a moment for you to try to, to brag about the community that you put together.

Speaker C:

What are some of the benefits that you see from the community aspect of being able to kind of chew on these situations together and put your heads together on that?

Speaker A:

Yeah, no, I think you're spot on.

Speaker A:

I think when you have a community of sort of like minded investors like that, you know, there's going to be a breadth of experience in that community.

Speaker A:

There's going to be people who are coming in and it's their first opportunity ever and their first deal and they sort of don't know enough, but they are hungry for education.

Speaker A:

And then there's going to be others that are very sophisticated investors that, you know, want to sort of understand to a very high level.

Speaker A:

And anytime we go into these opportunities, our due diligence with any particular partner is anywhere from three to four months.

Speaker A:

And you know, we're, we know the deal as well as, if not better than them.

Speaker A:

We do market analysis that maybe they haven't even done.

Speaker A:

We're doing criminal background checks on everyone we work with.

Speaker A:

And you know, because we're not, we're not giving 50,000 or $100,000 investment, we're giving 5 to $10 million at a time.

Speaker A:

And so when it's that amount of capital, you know, we, we don't think of it as money that we're taking from investors.

Speaker A:

Right.

Speaker A:

That is their hopes and dreams.

Speaker A:

And what they do with that, you know, at the end of that deal is going to be college education for children.

Speaker A:

It's going to be the best anniversary vacation ever.

Speaker A:

Like those, those things are earmarked for a very specific purpose.

Speaker A:

And we take all of that very, very seriously.

Speaker A:

And so our due diligence is sometimes off putting, if I'm being honest, to, to the folks we work with, because of how proing we get.

Speaker A:

Because it's important.

Speaker A:

We need to understand the ins, the outs and you know, backwards and forwards.

Speaker A:

Because, because it's a lot of capital we're bringing in and transparency is so critical.

Speaker A:

If ever anything would stop us from working some great with someone, it's.

Speaker A:

I don't know if I can answer that, then we're done, right?

Speaker A:

There's always an answer.

Speaker A:

We don't have to like the answer, but there always has to be an answer.

Speaker A:

And if there's any lack of transparency, you know, giant red flag.

Speaker B:

Yeah, absolutely.

Speaker B:

I'm curious how you, you know, I have conversations all the time with, I literally had dinner last night with a guy who's very much a Warren Buffett investor.

Speaker B:

You know, he is in the stock market.

Speaker B:

He's really, he's, he's got, he's dabbled in real estate a little bit, but he really has no interest in, in investing in alternative assets.

Speaker B:

And I wonder if you have any sort of personal battle plan for how you diversify into more traditional equities.

Speaker B:

And you know, when you decide, all right, I'm going to turn up the volume a little bit on alternative Assets, it's been, the stock market's been on a tear the last two years and you know, if you're invested in multifamily, it's been the opposite of been on a tear.

Speaker B:

And I'm curious how you, how you balance that risk reward for those different sort of different asset classes that you're, you're involved in right now.

Speaker A:

Yeah, and I think, I think that's great.

Speaker A:

I would, I would say my recommendation would be to be in all of them.

Speaker A:

Right.

Speaker A:

And so the more asset classes you're in, sort of the less the volatility, the less tied you are to any particular, particular market cycle.

Speaker A:

And they're non correlated assets.

Speaker A:

So one particular asset class is going to be sort of functioning irrespective of what others may be doing.

Speaker A:

And there's always sort of micro economic changes that are going to affect one asset class over another.

Speaker A:

But it sort of doesn't bother you if you're in enough of them.

Speaker A:

So as an LP, I'm in 25 syndications, my wife and I.

Speaker A:

And so you name the asset class, we're in it.

Speaker A:

And so that part of it is great because you know, even if a couple of those go to zero, which they will undoubtedly the other ones are going to do so well that, that one that went to zero or two that go to zero are not really material consequence.

Speaker A:

And so you know what I tell people that are sort of in the market and love the market and are like, there's nothing wrong with the market.

Speaker A:

I think it's fine.

Speaker A:

I think, you know, it's a good place to put your money.

Speaker A:

It's safe, you know, and if you look over, you know, historical numbers, you're going to do 8% a year typically.

Speaker A:

Right.

Speaker A:

For, for over the long term, these syndications, if you get into good ones, are, are in their 20s, right.

Speaker A:

The opportunity to sort of amplify returns is really concentrated in some of these opportunities.

Speaker A:

For example, we do some land ones, for example, which are great.

Speaker A:

There's no leverage.

Speaker A:

We buy in, in cash.

Speaker A:

There's sit, there's really no downside risk outside of time to sort of rezone and then resell that land.

Speaker A:

There's not a lot of advantage.

Speaker A:

You know, you're not going to get depreciation, you're buying dirt, dirt's not depreciating.

Speaker A:

You're not, you know, there's not a whole lot of tax advantages, but you make 3-5x, you know, multiples on your, on your initial capital outlay.

Speaker A:

And so in three to Five years, which is, which is great.

Speaker B:

I'm a big fan of Nicholas Nassim Taliban, wrote the book Antifragile.

Speaker B:

Highly recommend a lot of his writings and he talks about barbell investing and with the whole idea of sort of like you're putting a large amount of your money into sort of safer investments, you know, and I think with him it's, it's literally he's doing like risk, you know, like bonds and things like that.

Speaker B:

But then there's a small bucket that is going into, in his case, venture capital, like, and this is much more ventral capital thinking where you know, like you said, there's a good chance a lot of those are gonna go to zero, but then there's the other ones that are gonna go to 2,000%, you know, and, and sounds like what you're talking about is a similar sort of mindset is like just not on a, you know, you're probably not gonna get a 2,000% return on a, on a multifamily syndication.

Speaker B:

But you know, and you may get some to go to zero, but you may get some that, you know, give you a 4x equity multiple, you know, and so you can, you know, and you're, you've got the benefit of being diversified across a multitude of operators, asset classes and probably geographies that, you know, you're not, you're not all in on multifamily, you're not all in on self storage, you're not all in on office or whatever.

Speaker B:

Is that kind of the, the mindset, the game that you're playing?

Speaker A:

Yeah, absolutely.

Speaker A:

And I think, you know, most of our clients are physicians, but we have, you know, we have all sorts of high net worth individuals that will invest, you know, with us.

Speaker A:

But yeah, a lot of times we'll get a deal.

Speaker A:

And I'm super excited and I know it's going to be a great deal.

Speaker A:

And they're like, how much should I put in?

Speaker A:

You know, should I go above the minimum?

Speaker A:

Should I, should I wait for another opportunity?

Speaker A:

I was like, look, I'm, I'm a huge believer in not putting all your eggs in any one basket.

Speaker A:

So, you know, you want to leave opportunity to be able to get into multiple different deals.

Speaker A:

I'm truthful about how well I think a deal is going to do.

Speaker A:

And the important thing is knowing their circumstance and what's important to them.

Speaker A:

You know, do they need a tax break, do they need a tax break off of passive income or do they need it off their active physician income?

Speaker A:,:Speaker A:

But I would say, you know, do the minimum in as many of these as you can.

Speaker A:

You may not hit higher returns, but you're going to overall have a much

Speaker C:

safer portfolio and you'll get smarter along the way.

Speaker C:

You get better, no doubt about that.

Speaker C:

You'll be more well rounded.

Speaker C:

I'm glad you brought that up.

Speaker C:

About tax benefits, you've got a couple things in your biography that, that frankly are veteran moves but kind of on other ends of the spectrum.

Speaker C:

So this is a little bit of a two parter.

Speaker C:

I want to get to the discussion about energy.

Speaker C:

And I know you're a short term rental guy.

Speaker C:

I had 14 of my own, just got rid of four of them.

Speaker C:

I've got 10 left and own a property management company that manages mine and another 75.

Speaker C:

Neil's had multiple short term rentals as well.

Speaker C:

Bonus depreciation's a real thing.

Speaker C:

I'd love to get into that conversation, but before we do, the other end of the spectrum is that you also talk about money jail with traditional retirement accounts.

Speaker C:

So for busy high earning income professionals who maybe are maxing out their 401k but feeling stuck, what does that conversation look like?

Speaker C:

Because these people are not looking for depreciation.

Speaker C:

If they are, let me ask it a different way.

Speaker C:

Are you talking about using retirement accounts as an investment vehicle like SDIRAs or EQRP accounts and things like that or are you just talking about educating and giving people another avenue or maybe another bucket outside of that?

Speaker A:

Yes, a little bit of both, honestly.

Speaker A:

And so yeah, I think our traditional retirement vehicles, when you're with an employer with whether it be a 403B or 457 or 401K, that's the money jail, right?

Speaker A:

You're sort of I'm going to save because I'm putting in all these pre tax dollars into this vehicle of which you have, hey, choose one of these, you know, six things you want to park your funds into.

Speaker A:

It's very limited asset classes, very limited places that you can store that and you got to hold it there till you're 65.

Speaker A:

You can't enjoy it in advance unless you want to pay penalties.

Speaker A:

And you know, so that, that locks it up, right?

Speaker A:

I don't, I want to enjoy it now, not 65.

Speaker A:

And so I actually stopped contributing into retirement a number of years ago which again you have to be in A place, I'm not advocating that for everyone.

Speaker A:

You have to be in a place where that makes sense for you to do so.

Speaker A:

I get a company match, I'm not going to give away free money.

Speaker A:

And so, you know, 4% match or whatever your employer gives you, please, you know, don't turn that down.

Speaker A:

But that's all I do.

Speaker A:

I can do so much better now with post tax dollars, with what I'm doing than I ever will with pre tax dollars than that Delta doesn't make a difference.

Speaker A:

And so for me it's about educating that there's other ways to be able to earn returns on that cash without having to wait until you're 65.

Speaker A:

And there are other folks that where do I get the capital for these investments?

Speaker A:

I haven't saved enough.

Speaker A:

And you can take a loan from your 401 or 403, you're allowed up to a 50k loan.

Speaker A:

You're essentially taking a loan from yourself.

Speaker A:

It's not an early disbursement, it's just a loan.

Speaker A:

And you have a five year limit.

Speaker A:

Typically with most of these plans that you have to repay that.

Speaker A:

Luckily most of the deals are three to five year deals and so you'll be able to repay that comfortably theoretically, assuming the deal goes well.

Speaker A:

But it's a great way to take money out of money, jail, a little bit of it at least and invest that in something else that's going to do much better than what you would inside of the market.

Speaker C:

On the other end of the spectrum is aggressively investing for depreciation like against.

Speaker C:

It's for, for short term rentals.

Speaker C:

I spent for several years, my strategy was buying small multifamily properties with bad long term tenants in place and converting them into Airbnbs.

Speaker C:

Now Neil and I live on a little island called Carolina beach right off the coast of Wilmington.

Speaker C:

It's a beach town, so it's obviously very good for that.

Speaker C:

But one thing we can't control is the amount of other people that are also going to do the same thing.

Speaker C:st, you know, I had there was:Speaker C:

And then eventually over the next few years, especially coast post Covid, that ballooned up to 3,600.

Speaker C:

And what you can't control with short term rentals, unless there's a moratorium or you have to have a registry and some towns are like that.

Speaker C:

What you can't control is how many other people are doing it and it's a review based system.

Speaker C:

So the longer you do it, the more success you're going to have.

Speaker C:

But the real reason why some people are continuing to rush in while a lot of people are rushing out is because they're playing by different rules to the game.

Speaker C:

It's at this point more high earning income individuals are purchasing properties just to do the cost segregation study and pull the bonus depreciation out from day one.

Speaker C:

And a lot of those people tend to be physicians, high earning income individuals, they got to get the rep status one way or the other or their hundred hours of training.

Speaker C:

There's some rules that you need to follow, but a lot of times it may not be people investing for cash flow anymore.

Speaker C:

It may be people investing for being able to strip out.

Speaker C:

I've got a quadplex of mine that's on the market right now that has between 180 and 200,000 of, of depreciation that could be taken from day one.

Speaker C:a couple years and then turn:Speaker C:

Is that a strategy that you guys are employing in your community more and more just because you have so many high income earning active investors?

Speaker A:

Yeah.

Speaker A:

So I think, I think, yes, definitely.

Speaker A:

I think more people are talking about it, more people are learning about it.

Speaker A:

To your point, I think it, it appeals to a small sort of, you know, segmented population that are willing to put that time and effort in because it's not an easy task.

Speaker A:

And there are certain rules that you definitely have to do and follow to be able to claim that bonus depreciation, get that off of your active income.

Speaker A::Speaker A:

I was like, well, you can do the short term rental taxable poll and do the work and get it that way.

Speaker A:

You can get real estate professional status, but you're not going to do that being a full time physician unless you have a spouse that you know can claim those hours and is actually doing that work or you have energy investments, you know, that are sort of, for lack of better term, subsidized by the federal government to, to invest in and they will give you credits off of your active income for that.

Speaker A:

But that's really the only three ways I know of at least that that physicians are able to offset that.

Speaker C:

Yeah, I think that's the best way.

Speaker C:

I think energy is probably the, the least laborious way to do it.

Speaker C:

That's, it's a great way to look.

Speaker C:

But I'm curious about this too with your community.

Speaker C:

And now you guys are, you're, at this point you're a capital aggregator.

Speaker C:

Like you are allocating large amounts of capital on benefit of a, of an entire group.

Speaker C:

And whether meaning to or not, you're a fund of funds or a COGP partner, you are a capital aggregator with a group of ultra high net worth or high net worth individuals that collectively are basically like a fractional family office.

Speaker C:

And because of that, you should be able to get preferred terms, not a preferred return, preferred terms.

Speaker C:

And negotiating something for yourself that is outside of what a typical operator is going to offer.

Speaker C:

You bring it to them, be like, hey, we can fund this whole deal or a large portion of this deal and you can weaponize that.

Speaker C:

You can get better terms, less fees.

Speaker C:

You can get what's called most favored nation status where you're getting paid first or prep equity.

Speaker C:

And you can also go after the depreciation.

Speaker C:

The depreciation doesn't have to be pro rata.

Speaker C:

You can say, hey, we want to negotiate for a bigger chunk of this or that.

Speaker C:

Are you guys finding yourselves in a position where you're having more of those conversations about negotiating and creating custom offerings and maybe even taking the lion's share of the depreciation off of a project for your investors?

Speaker C:

Because you're going to get a benefit off of it in a way that people investing with the self directed IRA are not going to.

Speaker C:

So a lot of times there's depreciation that can be moved around to who it's going to benefit the most.

Speaker C:

Are you finding yourself starting to have more of those conversations about customized offerings?

Speaker A:

Yeah, absolutely.

Speaker A:

And it's, it's interesting because I think to each sponsor, something else is going to be important.

Speaker A:

And being able to come in where we are the sole capital allocator is a position we love to be in.

Speaker A:

We're not always, and I understand, you know, folks have, you know, again, relationships with others that they've had for a long time, but we like to be exceptional partners with anyone we join forces with and in development and doing, you know, we've done ground up and you know, the saying goes, if you're not, if you're not in the room, you're sort of on the menu, right?

Speaker A:

And so we love to be in the room.

Speaker A:

We love to have, you know, whether it be an advisory board position.

Speaker A:

But you know, and maybe not.

Speaker A:

It's, maybe it doesn't get to decision making authority.

Speaker A:

But if we're the sole capital allocators, you know, we, we come up with a way that we're able to advocate again for all of our investors in that our voice matters.

Speaker A:

We think that's so important.

Speaker A:

We're not the experts, you know, full deference to expertise.

Speaker A:

We know they're the experts in, in running that asset.

Speaker A:

But, but we have some business intelligence, we have some thoughts about, you know, sort of EQ and how to handle our investors and what's important to them and messaging and you know, again, transparency.

Speaker A:

So as much as possible, we like to have, you know, be able to have a voice in their ear.

Speaker B:

You mentioned the term advisory board.

Speaker B:

I'm curious what exactly you mean by that and what it looks like on your end.

Speaker A:

Yeah, so we're, we're on a couple of different advisory boards, especially on those opportunities where we've brought the majority or a significant amount of capital and that, you know, some of those are funds.

Speaker A:

And so if there's a decision that needs to be made to purchase the next asset, we're actually involved in that decision.

Speaker A:

We look at the underwriting, we look at, you know, some of the numbers and say yay.

Speaker A:

Or we have concerns.

Speaker A:

And it, it gives us a little bit more insight to the operations as opposed to just being blind sort of limited partners, which we are.

Speaker A:

To your point, we're a fund of funds.

Speaker A:

We're an SPB that's coming in with, you know, a large amount of capital.

Speaker A:

But you know, we like to sort of be able to have some insight where that goes.

Speaker A:

Which the majority of the time as an lp, you have no decision making authority.

Speaker A:

And so we like to be able to have some of that to advocate.

Speaker A:

And so we do that through advisory board positions.

Speaker B:

Got it.

Speaker C:

This is not something that I asked most people.

Speaker C:

In fact, I don't remember the last time I did ask this.

Speaker C:

But you're very, very well rounded in terms of the different types of assets that you look at, the different types of operators that talk to.

Speaker C:shooting up at the end of, of:Speaker C:

You got office and multifamily kind of taking it on the chin, but slowly on the way back.

Speaker C:

But there's some, you know, discrepancy about where it's going to settle and when it's going to settle.

Speaker C:

But with your well rounded background, is there anything, any asset class that you're excited about over the next few years, over the next five to 10 years that you think think people should be looking at, or is it really pigeonholed because you're dealing with a very select group of investors that are looking for very specific things?

Speaker A:

I think it's pigeonholed to an extent, but I think most people want to be able to put their dollars where they're going to be able to get maximum benefit and maximum return for the most part of folks we talk to.

Speaker A:

You know, the recommendation is always not to like the tax tail, wag the dog, right.

Speaker A:

Which some of the people get into in the short term rental space and using the.

Speaker A:

The tax loophole because they're doing it for tax reasons, they're not doing it for investment in cash flow, like you said.

Speaker A:

And so we are very mindful about making sure that's not the sole motivation for people.

Speaker A:

But I think in terms of asset classes, I think the jury's out a little bit on AI and what's going to happen there.

Speaker A:

But I think there's no stopping that train.

Speaker A:

It's been super impressive.

Speaker A:

And I think the growth of data centers and alternative energy that's going to feed those data centers, because they're huge energy consumers, I think is a great place to be looking for the next three to five years.

Speaker A:

I think land that's going to house those data centers, I think, you know, sort of infrastructure that's going to supply them, whether it be chips and manufacturing.

Speaker A:

I think a lot of that is likely to boom over the next few years.

Speaker B:

It's such an interesting way to look at it.

Speaker B:

And it reminds me of the analogy of, you know, when they talk about the gold rush, the people who really made money on the gold rush were the people who supplied the infrastructure to look for the gold, the Levi Strausses, the people who were making the pans and the infrastructure to handle that.

Speaker B:

The problem Clint and I have actually we moved to a data center conference to see about was that something we wanted to look into, building a data center.

Speaker B:

And the challenge that they're facing is that the amount of infrastructure and money that you have to put into the data center is massive.

Speaker B:

And that by the time that data center is built, a lot of times it's obsolete.

Speaker B:

And so that's why we very quickly were like, yeah, probably not for us, but what you're talking about is looking for the infrastructure around it that's feeding that beast.

Speaker B:

That is probably not going to go away anytime soon, but maybe don't be directly involved in that business, but look for the opportunity around the edges.

Speaker A:

Yeah, yeah, I think so.

Speaker A:

I think that's spot on.

Speaker A:

I think a lot of that is going to help because you've got, again, you have experts that are going to be doing this in a very well thought out way.

Speaker A:

Right.

Speaker A:

And so I think anything that we can do to support that sort of industry is going to be a real boon to investors.

Speaker C:

Completely agree with that.

Speaker C:

Listen, for the sake of time, yours and the listeners, we'll start wrapping it up here.

Speaker C:

I want to say this is a great conversation.

Speaker C:

I certainly enjoy it.

Speaker C:

I could have kept it going up for a lot longer.

Speaker C:

I know that one.

Speaker C:

There is one question I'll ask you that we used to ask everybody, like, what's your favorite book?

Speaker C:

Or something like that, but we'd love to try to get a little bit better of a response if the answer is not a book, but the question is within your group, and maybe you have an educational resource that is a better fit for this.

Speaker C:

But when people come to you, they recognize what you're doing, they recognize what you're built, they recognize that they want to learn and be a part of it and get involved somewhere.

Speaker C:

Is there a recommendation that you have for a book, a resource, a podcast or educational source that you find yourself recommending to friends and colleagues more than any other?

Speaker A:

You know, that's hard to say.

Speaker A:

I can't say that I do.

Speaker A:

I think it depends on where they're coming from.

Speaker A:

And there's, there's such a vast amount of information, you know, at our fingertips these days that, you know, I'll give them topics and sometimes certain books, depending on what they're looking for, you know, to look into.

Speaker A:

But I think it really depends on what their need is.

Speaker A:

And we try to offer, you know, education on various asset classes and, and things like that.

Speaker A:

But, but you're right, it becomes a one to one as opposed to a one to many.

Speaker A:

Right.

Speaker A:

And you're, you're having these individual conversations with people.

Speaker A:

But, but I think everybody has unique sort of needs and interests and, and it almost has to be that way.

Speaker A:

And I know, you know, everyone's got limited time and, and, and things like that, but I think there's folks out there that make the time that, you know, want to have those conversations that appreciate that, and if you can pay it forwards, if your knowledge or your experience is able to help somebody else, then, you know, why not share that?

Speaker A:

That's, that's the biggest gift you can give them.

Speaker C:

That's actually exactly the answer that you would expect from an ER physician whose job it is to individually diagnose and triage people based upon their condition and get them to the healer that they need.

Speaker C:

So that actually is a great answer from you.

Speaker C:

So I completely understand that.

Speaker C:

All right, sir, listen, if any of our listeners want to connect with you for find out more about you, your group, continue to learn along with you, what would be the best way for them to connect and do that.

Speaker A:

Yeah, I would love to again have conversations with anybody.

Speaker A:

That's real estate.

Speaker A:

Curious if you will, but.

Speaker A:

Yeah, the syndication doctor.com is my website and if you want to email the syndicationdoctormail.com Excellent.

Speaker C:

Well, thank you so much, sir.

Speaker C:

We really appreciate your time.

Speaker C:

We'll put all of that information in the show notes.

Speaker C:

We look forward to sharing that.

Speaker C:

And again, can't tell you how much we appreciate your willingness to come on, share what you're up to and educate ourselves and the listeners.

Speaker C:

So thank you very much.

Speaker A:

Yeah, I think thank you both for doing what you're doing for all of your listeners.

Speaker A:

I know it's providing them exceptional value.

Speaker A:

So thanks for having me.

Speaker A:

Really appreciate it.

Speaker C:

Appreciate the kind words.

Speaker C:

Listen, we're, we're all in real estate, but we're really all in the relationship business and we know that.

Speaker C:

So thanks for your time.

Speaker B:

Thank you so much for listening and watching the Truly Passive Income podcast.

Speaker B:

If you liked the show, if you think it would be useful for someone else, the greatest compliment that you could give us would be to share the episode.

Speaker B:

Leave a comment down below or leave us an honest review.

Speaker B:

If you have any questions, don't hesitate to let us know down below.

Speaker B:

And remember, with Truly Passive Income comes freedom of time, place, and the freedom to pursue your higher purpose.