How Real Estate & AI Tech Are Creating Millionaires: Lessons from Gary Lipsky & Douglas James

What this episode is about

The discussion centers on the intersection of real estate investment and artificial intelligence technology, highlighting how these fields can generate wealth, with Gary Lipsky sharing insights from his successful ventures in building a real estate portfolio through Break of Day Capital. Key points include the importance of strategic investments, tax benefits, and the broader impact of real estate on various business sectors, suggesting its relevance for a wide audience, regardless of their personal investment focus.

Key takeaways

• In real estate, control is power: build wealth by creating value, not just waiting for market magic.
• From dinner deliveries to multifamily investments, entrepreneurship isn't a straight line—it's a winding adventure with surprises!
• Investing passively means buying time—your money works while you reclaim your freedom for life's real joys.
• Aiming for a 'too-good-to-be-true' IRR? Remember: if it sounds like a unicorn, it's probably a horse in disguise.
• Success in real estate isn't just about metrics; it's the people: partner with pros, and market turbulence won't sink your ship.

Who speaks in this episode?

• Dan (Guest) · 14 min speaking
• Gary Lipsky (Guest) · 28 min speaking
• Douglas James (Guest) · 28 min speaking

What is discussed, and when

1. 0:00 – 5:00: Break of Day Capital, Gary Lipsky, Dan (Money Mondays host), Southern California
2. 5:00 – 10:00: Best-in-Class, Invest Smart: Spotting Red Flags in Real Estate Syndication, Real Estate Investor Podcast, Bigger Pockets
3. 15:00 – 20:00: State Farm
4. 20:00 – 25:00: Douglas James, Break of Day Capital, Gary Lipsky, LeadFi
5. 25:00 – 30:00: LeadFi
6. 30:00 – 35:00: Artificial Intelligence
7. 35:00 – 40:00: Artificial Intelligence, AI Company
8. 40:00 – 45:00: RIP Medical, Douglas James, LeadFi, Pencils of Promise
9. 45:00 – 47:15: Douglas James, LeadFi

Notable quotes from "How Real Estate & AI Tech Are Creating Millionaires: Lessons from Gary Lipsky & Douglas James"

• Investments, strategic investments, tax benefit investments, and all things related to real estate. It's called Break of Day Capital, and his name is Gary Lipsky. Now, as we go…

  about Gary Lipsky · at 0:26

• Actually, I wrote Bestin-Class, which is a best-selling book on asset management. and Invest Smart: Spoting Red Flags in Real Estate Syndication. So, they'll teach you how to invest that money. But Bigger.

  about Best-in-Class · at 7:42

• Yeah. obviously go to our website, breakofdayc capital.com. You'll find our my two books, Invest Smart, and, best-in-class. you can get to our podcast there. You can get on.

  about Break of Day Capital · at 20:13

• A chef. As you're accumulating income, you got to start to consider what to invest into. You guys have heard my theory about 40 20 40% low risk, 40% medium risk, 20% high risk.…

  about Dan (Money Mondays host) · at 21:09

• For you. It might be for someone in your past, present, and future. So, without further ado, Mr. Douglas James, give the quick two-minute bio so we get straight to the money.

  about Douglas James · at 23:24

• Likelihood if you stayed in that game, you'd be very wealthy today, right? So, we look at things today like crypto, AI, right? Those are very intriguing technologies to me. I've been in crypto since 2016 and AI and blockchain are also.

  about Artificial Intelligence · at 33:54

• Having to get seen for all these wounds and there's no financial support. So, RIP Medical, every $1 we raise eradicates like $10 in debt for them.

  about RIP Medical · at 43:06

• One with the blue check. I think the I think the handle is the Douglas James. And then the website to LeadFi is leadfi.ai.

  about LeadFi · at 46:03

Who and what is mentioned in this episode?

People

• Douglas James — Person · Main guest (segment 2) · 4 mentions · first at 22:47
  He describes building LeadFi, a credit/financial-data enrichment platform for lead qualification, and discusses investing themes (crypto, AI) and charitable giving.
• Gary Lipsky — Person · Main guest (segment 1) · 2 mentions · first at 0:34
  He explains how Break of Day Capital structures real estate syndications/funds, what returns to expect, and how he approaches philanthropy and legacy planning.
• Dan (Money Mondays host) — Person · Host · 2 mentions · first at 1:13
  He frames the show’s three pillars (make, invest, give), interviews both guests, and prompts practical explanations and legacy/charity perspectives.

Books & papers

• Best-in-Class — Book · Referenced resource (authored by guest) · 2 mentions · first at 7:42
  Gary Lipsky cites it as his best-selling book focused on asset management, positioned as education for investors/operators.
• Invest Smart: Spotting Red Flags in Real Estate Syndication — Book · Referenced resource (authored by guest) · 1 mention · first at 7:52
  Gary Lipsky recommends it as a guide for evaluating syndications and doing due diligence, aligning with the episode’s investor-education theme.
  Actually, I wrote Bestin-Class, which is a best-selling book on asset management. and Invest Smart: Spoting Red Flags in Real Estate Syndication. So, they'll teach you how to invest that money. But Bigger Pockets is another great site that.

Companies & orgs

• LeadFi — Company · Core company discussed (segment 2) · 4 mentions · first at 22:47
  Douglas James presents LeadFi as a platform that enriches leads with credit/financial attributes via API to improve qualification, sales efficiency, and ad targeting.
• Break of Day Capital — Company · Core company discussed (segment 1) · 2 mentions · first at 0:31
  It is Gary Lipsky’s real estate investment firm used to explain syndications, funds, LP expectations, IRR targets, and operational value creation.
• RIP Medical — Company · Referenced charity supported by guest · 2 mentions · first at 42:20
  Douglas James highlights RIP Medical’s mission to eradicate veterans’ medical debt and explains the leverage of donations to debt relief.
• Pencils of Promise — Company · Referenced charity supported by guest · 1 mention · first at 41:57
  Douglas James cites it as an organization he supports that builds schools; he mentions contributing a percentage of revenue and building multiple schools.
  Of organizations that I'm a part of today which I believe you know of at least one of them is pencils of promise who build schools with kids from Mexico one school's like 25k I think we built nine schools so far I continuously.
• AI Company — Company · Referenced investment/affiliation (unnamed) · 1 mention · first at 35:49
  Douglas James says he is an LP in an AI company led by Howard Gets, describing AI-enabled business transformation and an AI trading algorithm.
  Gets. So, you know Howard, he spoke at Garrett White's mansion. So, Howard has been the CEO of a AI company for 33 years. and we have a team of 20 PhDs and what we do is we AI…
• Bigger Pockets — Company · Referenced education/community resource · 1 mention · first at 7:54
  Gary Lipsky points listeners to Bigger Pockets as a place to learn and get advice when starting in real estate.
  Spoting Red Flags in Real Estate Syndication. So, they'll teach you how to invest that money. But Bigger Pockets is another great site that you can go on and get advice from. but definitely get into a mentorship group too because being.
• Door Dash — Company · Referenced comparison company · 1 mention · first at 1:20
  Gary Lipsky compares his college-era restaurant delivery service to DoorDash to convey early entrepreneurial experience.
  Appreciate it. been an entrepreneur since I was a young kid. had a restaurant delivery service like a Door Dash and a Postmates in college cuz we saw that they were doing it in Boston where we were living. And so, we started one in.
• Postmates — Company · Referenced comparison company · 1 mention · first at 1:22
  Gary Lipsky compares his early delivery venture to Postmates, reinforcing his entrepreneurial background.
  Since I was a young kid. had a restaurant delivery service like a Door Dash and a Postmates in college cuz we saw that they were doing it in Boston where we were living. And so, we started one in New York City. co-produced three.
• State Farm — Company · Referenced grant provider · 1 mention · first at 17:21
  Gary Lipsky notes receiving grants from State Farm for his earlier nonprofit/youth-focused efforts.
  But we, we got grants from State Farm, the Lakers, a lot of local, organizations.

Concepts & topics

• Artificial Intelligence — Concept · Core topic (segment 2) · 3 mentions · first at 33:58
  Douglas James highlights AI as a disruptive investment theme and describes AI-enabled business transformation and AI-driven trading systems.
• E6 — Concept · Career milestone referenced by guest · 1 mention · first at 24:47
  Douglas James uses achieving E6 quickly as evidence of high performance and leadership in the Navy, motivating his later entrepreneurial transition.
  Realized I didn't want to be you know in the military for 20 30 years actually I made E6 in 5 years. So E6 is like a high level supervisory position, active duty. It takes the average person 12 years to hit that. I did it in 5 years.

Places & events

• Southern California — Place · Location of prior business impact · 1 mention · first at 1:46
  Gary Lipsky references serving 9,000 at-risk youth throughout Southern California via a prior after-school/outdoor leadership company.
  Leadership development company where we were serving 9,000 atrisisk youth throughout Southern California.

Media & podcasts

• Real Estate Investor Podcast — Media · Referenced podcast (guest’s show) · 1 mention · first at 7:35
  Gary Lipsky mentions hosting it as a free educational channel for learning real estate investing.
  Airbnbs or stuff like that or maybe some fix and flips. There's a ton of free education out there. I actually have a podcast, Real Estate Investor Podcast, where I have a lot of people on. but there's some great books out there.

Full transcript with timestamps

0:05 Ladies and gentlemen, welcome to a special edition of the Money Mondays podcast where we cover three core topics. How to make money, how to invest money, how to give it away to charity. Our next guest has accumulated a ton of real estate. He's been overseeing a real estate empire, if you will, helping investors deploy capital into safe investments, strategic investments, tax benefit investments, and all things related to real estate. It's called Break of Day Capital, and his name is Gary Lipsky. Now, as we go through this, I want you to consider maybe you're not a real estate investor or maybe you're going to do it in the future. But there's people in your life from your past, present, and future that may be very interested in real estate or may need real estate in their life. That's why these podcasts are important. Not all episodes will be for you. There might be someone that owns a chain of

0:55 restaurants, maybe someone owns a clothing line, or maybe someone like this with Gary that is deeply involved in the real estate space. Don't just listen for yourself. These podcasts are designed are for people in your life from your past, present, and future. So, without further ado, Gary, if you can give us a quick two-minute bio so we can get straight to the money.

1:13 Yeah, thanks for having me, Dan. Appreciate it. Um, been an entrepreneur since I was a young kid. Um, uh, had a restaurant delivery service like a Door Dash and a and a Postmates in college cuz we saw that they were doing it in Boston where we were we were living. And so, we started one in uh, in New York City. um co-produced three lowbudget independent uh films in my 20s. Um then it's it's funny. I I've kind of had three different lives. I started an afterchool outdoor red and leadership development company where we were serving 9,000 atrisisk youth throughout Southern California.

1:48 Um and then I had been investing in real estate for a while and got into it full-time when I sold that company

1:55 uh in uh at the end of 2016 and been uh doing real estate uh full-time ever since. and and and built up a a a great team and and quite a bit of portfolio.

2:07 So, at first it was your own capital, just focused on buying some things for yourself.

2:11 What did you like at first? What was your first things you were interested in? Well, I love the um it was a great way to build wealth um where I had control when I invested in the stock market or other things. I I felt like there was a lack of control and where I can look at a property, see the value that I can create and and get the results without relying on outside factors. And so that's what I really loved about it. And then it was just a matter of scaling up over time and pooling resources from bringing in other investors. So, when did you decide to go from I'm doing this for Gary in my family to you know what, I'm going to have some friends or acquaintances or strangers be able to co-invest with me?

2:54 Yeah. So, it was a 2017 I was really studying all facets of real estate and what is confusing when you start there's just so many ways to make money in real estate and you really have to focus like anything in life. And so I I honed in on multif family because of the scalability of it. And I thought, hey, I had to start building up my own resume doing eight units, 12 units, 14 units. And then um I I became a part of a mentorship program where they're like partner with others and scale bigger. And so uh I did that and we we bought a 42 unit for $1.65 million. Um, and we raised a million dollars on that deal. So, that was the first time we kind of opened it up for others. Um, and and then from there we just started doing doing more deals.

3:46 But, uh, heck, it was it was super hard raising money in the beginning and learning how to communicate that because it's less about selling and and more about sharing an opportunity and just gaining confidence in that in that skill set. So someone that's out there that's a doctor, lawyer, accountant, billy of a business and they have some extra capital, why do they invest in something like Break a Day Capital versus just going and trying to do real estate on their own?

4:14 Yeah, it's uh it's it's hands-off. It's passive income. So what you're trying to buy is time and freedom. And if you're if you're investing in it yourself, potentially you can make more money, but the problem is it's a whole another business and you don't have that expertise. We have a team of experts that do this full-time. We invest in our own deals. My whole team invests in the deals. And so, uh, you get that, you get also economies of scale. So, we're able to leverage, uh, teams and and resources because we have such a w huge pool of money to buy these bigger properties, which are actually easier to manage versus a smaller property. So, if someone is considering investing into a fund or into a syndication deal, what's a ballpark that they should be considering to look for? Is it 8%, is it 12%, 10%, 15? Like, what should they be considering? Like, what is a good deal?

5:09 Yeah. Um, every deal you see on paper looks fantastic. And so, you really got to uh do your own due diligence on the team that you're going to invest in. But I think a reasonable deal typically what we're shooting for is like a 15% irr. Um

5:26 what's IRRa? So it's uh it takes into account uh time value of money uh internal rate of return where you also might hear a AAR which is annual average return which will be slightly higher but it doesn't take in when you're getting the money. So if you get all your money at the end of the deal it's not nearly as good as if you're getting it uh along the way. Um, but if if a deal is promising 25, 30, 40, if it sounds too good, it usually is. So, go with an experienced operator that can uh will will underpromise and overperform and will know how to navigate through rough times because like any business, there's there's ups and down cycles. And so you need to make sure you know the person that you're investing with knows how to to to make a a a bad deal good or a good deal great.

6:17 So let's say I'm an LP and I say, "Okay, break day capital. Here's $250,000. How long am I locked up or what is like just give us the main idea of what the process looks like if I want to wire money."

6:27 Yeah. So typically uh you're going to be invested in a deal three to five years, but it's not liquid. Um, so you've got to factor that it's going to be in there for five years. You know, o overestimate because if you need that money uh and it's and it's in something that's not really liquid, you're you're not going to be able to get that money out. Now, certainly there are mechanisms that they're creating these days uh to do that, but it's still not a very um um uh fine-tuned system yet to like to trade like uh shares of of real estate like that. But uh so yeah, factor in fivey year whole time typically and in the um in the investment summary it'll tell you because some deals might go seven years even 10 years particularly if it's an os fund a a um an opportunity zone.

7:18 So let's say it's I have the same 250,000 but I want to go do it myself. Yeah. How how do I start? What do I research? What do I figure out to go try and take my own shot at glory?

7:28 Yeah. And there's plenty of people doing it. Um, a lot of people start with like Airbnbs or stuff like that or maybe some fix and flips. There's a ton of free education out there. I actually have a podcast, Real Estate Investor Podcast, where I have a lot of people on. Um, but there's some great books out there. Actually, I wrote uh Bestin-Class, which is a best-selling book on on asset management. Um, and uh, Invest Smart: Spoting Red Flags in Real Estate Syndication. So, they'll teach you how to invest uh, that money. But Bigger Pockets is another great um um site that you can go on and and uh get advice from. Um but definitely get into a mentorship group too because being around likeminded individuals really creates momentum in your business. Um and you could share um struggles, share needs and and and and really kind of rocket fuel your your growth. So

8:21 how do people find deals? Are they just going on Zillow? Are they just looking it up? Are they going to groups, going to events, talking to friends? Like where does the deal come from?

8:31 Yeah. So, it all depends what scale you're at. So, we're buying large multif family, 150 units or more. So, it's all broker deals. Um whether it's on market, offmarket, that's another story. But if you if it's a single family home, u may maybe it is uh Zillow. um definitely broker relationships or or real estate agents developing those relationships so they they know your criteria and when they have a deal that may fit it, they'll reach out to you which is a great way. Um and then there's also people that um if they're doing it on uh on a pretty decent scale but smaller properties, they'll do uh direct to seller deals. Um so maybe they're sending out yellow letters or they're calling they have a team that calls people. So depending upon where you're at, there's lots of different ways to get deals. Um, so that depends on on what type of what uh what type of asset you're looking for and and the size of

9:28 it. So let's just use an example of 150 unit multif family and let's say you're buying it for $30 million for example. Is that a syndication for one deal or do people invest into the fund and that's that fun units as part of the fund? Yeah. So we do it in a in a both ways. So someone can invest in just a a single asset or they can invest in a fund where they get um uh diversification because it's over multiple deals. And so the diversification I think is is a better way to go because if if for one reason one deal doesn't perform as well your your your risk is spread out. A lot of investors, at least a lot of investors that we encounter, really prefer that single asset. They feel like they could pick a winner. Um, so I I don't know, every deal that we do, we feel like it's going to be a winner. It's really hard.

10:23 It's like your babies, you Yeah. You don't have one, you know, one deal that you think is going to do better than the other until you actually sell it. So, uh, you know, we we we give a lot of different options for our investors based on what what they're looking for, what what, uh, what their criteria is, what their need is. Um, are they looking for more cash flow? Are they looking for more appreciation, tax benefits? So, we we give a lot of optionalities.

10:49 All right. So, let's walk through a 150 unit complex, $30 million is the example number. I'm the investor. like I'm gonna put in 250,000 out of your raise for that group for that 150 units. What does that look like? Like walk me through the main concept of that in a syndication deal of one deal.

11:06 Yeah. So once we take over a property, we're going to improve operations. So we're going to we're going to um try to lower expenses if it makes sense. Uh certainly try to uh increase income um by raising rents, fixing it up. So, we'll uh update the landscaping, maybe paint, maybe add a dog park, add some amenities. Um, and also maybe add some income streams that they might have. So, maybe uh preferred parking by their um by their apartment and and maybe we're only getting $25, but when you multiply that over 25 units over 12 months,

11:41 it increases it. Or or privacy patio walls, like little things to like add it. an apartment we bought at the end of 2023. We um added a uh a water conservation plan. We changed out the toilets that were using 3.5 gallons uh per flush. Now they're using8 gallons and we changed out the shower heads and the faucets.

12:03 We're saving over $150,000 per year. Wow. Because of that, um because it's a it's a big property. And so when you divide it by the cap rate, we we created $3 million of value for that property. Wow.

12:15 Yeah. Um, and so our investors are going to get cash flow throughout the deal. Um, probably starts around the the sixth or seventh month. So, as we start doing the renovations and increasing the uh the NOI, they'll get cash flow. They'll get tax benefits because they'll they'll see that on their on their K1, they uh they get they own a piece of that property. So, um so let's say they they invest 100,000 right now. Uh depreciation is back up to 100%. So they might get anywhere from 80 to $100,000 loss on their K1 that they can use against passive gains. And if they can't use it now, then they can carry it forward to another year where whether we sell the property or they have gains from uh stocks or or whatever it may be. Um and uh we give them monthly updates because we want to keep the uh investor informed on on how we're performing to what we projected. Um we have semiannual calls and then um uh ultimately when we find

13:14 the right time in the market cycle to sell then then we sell and our investors get 100% back of their money first. Uh they get a pref. So typically it's like a 7% pref on a yearly basis and then uh then we do a waterfall split after that.

13:31 So 150 units, $30 million. Five to seven years has gone by. Now the place is worth $40 million. How do you know when to sell or hold on to it or just make this one of your properties you just keep forever?

13:43 Yeah. Um we we like the um time value of money. So the longer we hold a property, we're not creating much value because like once we've maxed it out, then it's kind of, you know, skimming along. So we we do like to sell our properties. Um and so we're looking at the market where the the the cap rate is. So if we bought it these days in our market it might be a six cap but we know a couple years ago it was a four or a sub four. So when that starts getting to that market we you know to that cap rate we know times are pretty frothy. And so it might be time to sell because how much lower is it really going to get? And so we're looking to see the market dynamics.

14:28 We're understanding market cycles. Um, and that that's really important because we certainly know a lot of people that didn't sell 2021, 2022 and held on and now that property lost a ton of value. So, selling at the right time is is super important. And we've sold deals within two years because we just took advantage of the market and we weren't going to get greedy.

14:53 So, you said something six cap. What is a six cap? Yeah. So, um, that's based on your income. So let's say you had a million dollars of income and the cap uh rate is 6%. So you divide the million by 6% and that's the value of your property. So

15:10 whereas a single family home it's it's it's um based on what someone is kind of willing to pay and and for commercial real estate it's based on your NOI what someone is willing to pay.

15:24 All right. So from you on a personal perspective, you've got all this real estate action going on. Are there other things that you like? Do you ever invest in the stock market? Do you ever angel invest? Do you like Bitcoin? Are there other things you consider about investing in or you're so passion about real estate that you just keep doubling, tripling, quadrupling down? almost all my money is in real estate and and we we've kind of we've done posts on it as well because I'm I'm investing in my own deals, but I do have a very small piece of Bitcoin. I was like, you know, who who knows where it's going to go, so let me I want a piece of that action. Uh a good friend of mine who was super sharp. Um uh I invested in his um uh marijuana company as well. Um, and I have a couple little things, some some stuff that are just super super stable because I need to have a certain amount of liquidity, but

16:15 I wanted to make uh earn some money for me because uh on all the on the loans and everything that I'm signed on, they they need to make sure that I have

16:23 um a certain amount of liquidity because if things go uh get tougher that I could help cover some of that.

16:29 All right. So, what about on the charity side of life? Why do you think it's important for there to be a charity component in your household as a family?

16:37 Oh, absolutely. We have to be giving back. Um actually this past weekend, uh my two daughters and I with um 15 other people went down to Mexico and built a home.

16:47 Oh, yeah. For a young uh woman and her and her two kids. It was a great experience and it was what was so cool about it was I got to do it with my daughters and have an adventure with them and really teach them about philanthropy as well. Um, and my my previous business, you know, working with 9,000 atrisisk youth. We started a nonprofit. Um, as well, probably over 20 years ago. Uh, it's since now to fund because we were we were kind of operating that sub $100,000 budget, which was really hard to do.

17:21 Um, but we, you know, we got grants from State Farm, the Lakers, a lot of local, uh organizations. Um, but you know, I've done very well and want to give back and um, you know, that that's super important to to me and my family.

17:35 So, let's say someone's considering what to bring to their household and they're like, I want to show my family a charity or do I ask them what do they care about? Do I ask the kids, do they like animal conservation or do they care about water or homelessness or breast cancer? Like, what do you what are your thoughts about how to figure out what charities to support?

17:55 Yeah. and you know um certainly I've I've supported some of my friends uh charities as well but it's important for you to have your own thing as well and and and discussing with your kids and letting them empowering them is is is pretty awesome um during the holidays u my brother and his kids they all come up with their individual charities and um we make a donation to them instead of giving them a gift because they get plenty of gifts you know

18:21 so um yeah it's it's anytime you can get your kids involved and really teach them about giving back at a at a young age is is is is awesome.

18:33 So, there's only one question I ask on every single episode and I've never gotten the same answer.

18:37 All right. Okay. So, you accumulate billions of dollars of real estate over the rest of your lifetime, but sadly at some point you pass away. What percentage of your net worth do you leave to those children? Yeah, it'll it would be uh very little. It's I want them to have a home uh to cover their medical um and for them to have money to uh uh export entrepreneurship, you know, for them to start a business, but it's not going to be where they

19:14 here's $80 million. Yeah. It's just not it it never works because that money over generation to generation dissolves so fast. It's in it's uh the statistics are insane how quickly the the money goes away. And and not only that, they're uh typically less inspired um not happy um looking for ways to fulfill themsel um and struggling. And so um giving um so much money to your to your children is is proven to be very uh unsuccessful but getting them teaching about uh them about money at a very early age allows them prepares them for that ultimate um um when they're getting that money. So if you're not doing it now and all of a sudden they get a ton of money, they're just not going to be prepared. So, you've really got to start them at a young age.

20:08 So, talk to everyone about your books and your podcast. Walk us through the actual names of they want to go research it.

20:13 Yeah. Um, obviously go to our our website, breakofdayc capital.com. You'll find our uh my two books, Invest Smart, uh, and, uh, best-in-class. Um, you can get to our podcast there. You can get on our email list um, and our social media. So, that's the best way to go. Breakupdaycap.com.

20:31 Can they find you anywhere on social media or find me everywhere? uh Instagram, uh LinkedIn, Facebook. Um you could look for my name, Gary Lipsky, or my company, Breakup Day Capital.

20:42 All right, guys. I'm actually going to have Gary on multiple times throughout the year because I like the very very detailed answers. A lot of times people do like esoteric answers or they take 19 minutes trying to answer the question. He gets very straightforward to the point to it. And since we live nearby, I'm going to have him back here. But the point of this is you got to understand for yourself, you might be earning capital in your core business. Again, you could be a doctor, a lawyer, maybe you are a real estate agent or accountant, whatever, personal trainer, a chef. As you're accumulating income, you got to start to consider what to invest into. You guys have heard my theory about 40 40 20 40% low risk, 40% medium risk, 20% high risk. In that middle category, when I talk about that medium is where you're trying to make between 10 and 30% for the year, I talk about real estate mostly. Real estate is

21:28 the way. And I try to bring people like this that can actually explain it in detail. So do a lot of research. Check on things that you are interested in. As you're making money from your core job, if you can take some of that money, 10 grand, 20 grand, 50 grand, 100 grand, and and even bigger, God willing, fantastic. Start to look at things that you could be investing into. But learn from experts. There's a lot of people that just talk on social media. A lot of people that just talk on podcast and YouTube. You got to find people like Gary that actually deployed a lot of capital, actually own a ton of units, actually been through the game and and been through the evolution of time because there's a lot of change that happened in this game and you've got to listen to people that really know what they're doing like Gary. So, I appreciate you guys. Make sure to have a discussion with your friends, family,

22:10 and followers about money. We'll see you guys next Monday on the moneymunddays.com. Ladies and gentlemen, welcome to the Money Mondays podcast where we cover three core topics. How to make money, how to invest money, how to give away to charity. This gentleman has done all those things and a cherry on top. So, what I want to talk to him about is these core topics, but also why he's doing his tech company that is enabling a lot of powerful companies and a lot of marketers out there and a lot of course creators, people that are in different industries to get better leads through his company called LeadFi. I will have him explain all the details and the general concept about that company, but also he's lived multiple lives. He's been in multiple different industries.

22:56 He's built up wealth. He's built up a family. So, we're going to talk through all different aspects of those things. Now, this is important. Each time I bring a guest to you, sometimes they might be in real estate. They might own nightclubs. They might be a celebrity or an athlete or everyone in between. The topics aren't always just for you. It might be people in your life from your past, present, and future that you might be able to tell some little tidbits of things that you hear on episodes like today. So, as you're listening, keep in mind for yourself, it might not just be for you. It might be for someone in your past, present, and future. So, without further ado, Mr. Douglas James, give the quick two-minute bio so we get straight to the money.

23:32 Yeah, brother. Thanks for having me, man. Um, yeah, so I started off, you know, from New Orleans, Louisiana. Uh, join the Navy when I was 19 years old. Um, I basically got in the military because, uh, back home it was like, uh, be homeless, um, go to college or join the military. That was like my three options. So, um, and I graduated

23:57 I graduated with like a 1.3 GPA, right? So, I was not a good student at all. I I could not sit in class and take instruction. Again, we're entrepreneurs, business owners, we want to be in control, right? So, um, and I didn't want to be homeless and disown my family and, you know, I was, you know, kind of like a I had a really rough upbringing. You know, I I grew up in a home where there was, um, emotional, physical, verbal abuse. My dad, you know, abused drugs, alcohol. I see and had had to endure things a lot you know kids should never endure and um and you know it got to the point where uh my family came to me it's like you got to join the military this is like your only option so I end up joining the military uh became a hospital corman um went off to do amazing things travel all over the world build schools for kids and uh realized I didn't want to be you know in the military for 20 30 years actually I

24:48 made E6 um in 5 years. So E6 is like a high level supervisory position, active duty. It takes the average person 12 years to hit that. I did it in 5 years. And it got to the point where like I wasn't really being challenged in the military. You know, everything to me is like a video game. Like when I was a kid, I could play any video game at the most difficult level. I could play Halo Legendary and beat it, right? Um so I know how to gify and look at everything including business like games. So if there's a result you're trying to get, you just reverse engineer with how to get there and you can figure out how to do it. So I got bored with the military.

25:22 You know, I could have been an officer, but um that point I decided to pro, you know, uh pursue entrepreneurial endeavors. So I found digital marketing. I started a local lead generation agency. So we helped over 50 different types of small businesses generate leads through Facebook ads. And within six months, I was making my annual salary in the military on the monthly basis. Um, and I was still serving active duty and I had my agency for four years. Um, and then naturally, you make money. People were like, "How are you making money?"

25:54 Uh, veterans active duty were coming to me. I remember a master chief. He was in for 25 years. He's like, "Bro, I've been in for 25 years. I'm getting out next month. Um, and I'm 45 years old. I don't want to sit in a classroom full of 19 year olds." So he's like, "Will you teach me what you do?" I said, "Sure." So I went home, created the worst video course you've probably ever seen. Uploaded to Dropbox, he gave me 900 bucks for it. The next weekend, he landed a client, paying them a,000 bucks a month. And that was my first realization. Wow. People are willing to pay you for what you know, right? So got into coaching, consulting, um, helped over 15,000 veterans transition from active duty to entrepreneurship. Um, we did over nine figures in revenue. I spent 30 million on ads to scale that business over about a seven or eight year period. Started off slow and then scaled up. We had our biggest years 2020

26:45 through 2024. And then kind of, you know, if you're spending any amount of money on ads, you want to be profitable, right? Obviously, you spend $1, you're trying to make two, three, four, five bucks out. So, I was getting to the point where um I was probably losing about a million a month for six or seven months straight about a year and a half ago. And it a lot of the issues we were facing with our paid traffic was, you know, leads are qualified. People lie on applications. Sales team says the leads are broke, but the marketing team always says, "Hey, the leads are qualified. They put that they make this on their application."

27:21 So, I couldn't just I I basically went through every endeavor you can possibly think of to try to get certainty around our lead quality and I couldn't find it. And um it wasn't until a year and a half ago I I and then me and my wife were going through some challenges and everything and in our marriage and I was just really deep in trying to fix the business. I I was on the hook for payroll. There was months um there was a couple months I couldn't make payroll and you know people in an organization I had over 100 employees and you know they sign up and if they're not bought into the vision it's really hard to artic they don't understand the ups and downs in business right and uh the way I look at business is there's green candles and red candles like if you invest in stocks or crypto right you can't have green candles all the time there's going to be red candle times same thing with your

28:10 relationships and your marriage there's going to be t times of lull and business is no same and I was going through that and uh I remember not being able to make payroll and it was really tough and I I look at it like I have 100 employees in my company but um it's not 100 people it's 100 families so if I don't feed them or pay them they can't feed their family so it was like a really tough time man so I just remember like literally we're getting into the story a little bit and you know I'll wrap up here in a second get back to you but like I just remember I was literally rock bottom you you know, I had lost eight figures um in my marketing. Um I was partnered with the wrong salespeople at the time and then uh you know, me and my wife were going through some very big challenges as well. I wasn't seeing my kids often and I just remember being in my office and I literally just fell to my knees, threw my hands up and gave my

29:03 life to Christ. And ever since that minute, man, I got to tell you, everything 180. The very next day, one of my good friends introduced me to my now business partner, which we now have LeadFi together for about 14 15 months and and marriage is great. Everything's on the up and up. So, I I owe everything to Christ and my friend's family for getting me through that time. So, short bio about me.

29:26 So, what is LeadFi? So leadfy is a technology platform that we developed and uh basically what happens is you know if you send traffic to a website or a funnel right you're collecting name email phone number right generally and uh we're we're actually able to take that name email phone um and return through API crucial financial data to your CRM about that contact. Say it's John Smith. He just signed up for your webinar. he's interested in your product or service. We're able to basically do a full credit report pull with Experian, Equifax, TransUnion just from name, email, phone. Now, that sounds crazy, right? Cuz if anyone, if you're in mortgage or real estate or if you, you know, underwrite, you know, you need address, date of birth, social security. We don't need any of that data because we created patent technology that's able to take the name, email, phone, identify exactly who that

30:24 individual is, acquire the sensitive data, then we have a 15-year relationship with the bureaus, and then we just directly salt pull real time, and then we get a full credit report. Now, from there, uh, we're not able to we can deliver the full credit report to our clients. Um, but since we're doing it for pre-screening purposes, it's what banks do to send us pre-approved credit cards in the mail all the time. I got one just earlier this week when I to check the mail. Um, it doesn't require a checkbox consent. So, we get the name, email, phone, we pull the information, and then we deliver the exact credit score, how much money they can spend on the credit cards right now in their wallet, their debt to income ratio, their um their annual income, and then we have underwriting. So for people if you're trying to figure out you know how much money can you raise for this individual we can actually deliver a

31:15 pre-approval for additional business funding as well through the API and then we just basically take the data deliver it to you and now you can optimize your sales process your sales team and your supercharger your targeting on meta and Google if you want to get in front of high credit score individuals.

31:31 So who is your clients like who is lead for? Leifi is for anyone that sells really high ticket online. That's who we've worked really well with or really any business that generates traffic. So, I mean, we're in the social media game, right? Like, if you're not on your phone, you know, 90% of all sales start with a video. So, you got to know, you got to understand that all the traffic's coming through your phone, right? So, we work with business owners that uh typically sell high ticket products and services. They could be coaches, info products. We work with stem cell clinics, dental clinics, people that offer funding. Um, we're in the mortgage space as well. So, right now we have over 200 brands that are all from either, you know, the low six figures all the way up to nine figures. Um, some clients are, you know, generating maybe a few hundred leads a month to a few thousand leads a day. So, um, and they

32:26 do the credit checks, uh, instantly and they're able to identify like who's financially fit right out the gate. All right. So, on the investing side of your world, how do you decide what to invest into when you have so much access to real estate, stock market, cryptocurrency, angel investing? There's you have access to so many humans, especially because you have got hundreds of clients. How do you pick and choose what you invest your own capital into?

32:47 Yeah. Um, just by partnering people that are a lot smarter than me, right? It's the easy answer. I really love disruptive technology and stuff that's super innovative that's uh going to take over and take off in the next 5 or 10 plus years, right? So, um I remember reading a book called uh diffusion of innovation. If you want something you want to read something before you go to bed and get like just put to sleep, read that book cuz the language is super heavy. But um the diffusion of innovation talks about how every time there's a new technology it's going to become massly adopted and it goes through the phases of early investors to early majority late majority lagards right so um I always remember that book and whenever I see technology and I go back to like the internet right when the internet came out in 99 there was newspaper clipping saying that the internet was a fad you'll never

33:39 you know order groceries date people I mean look at us now you're going to put this video up and it's going to stream on the internet, right? So, um, so you look at things like the internet and if people if you bought like do sites in the early 2000s, late 90s, I mean, high likelihood if you stayed in that game, you'd be very wealthy today, right? So, we look at things today like crypto, AI, right? Those are very intriguing technologies to me. I've been in crypto since uh 2016 and uh and AI and blockchain are also technologies that I'm also invested in.

34:13 So anything that is early where there's not many people talking about it and is is good for me because I know if a lot of people are talking about it the general public that's not that means it's already diffused amongst general population right so for me right now the biggest things that I'm invested in obviously I'm holding big cap cryptos Bitcoin Ethereum XRP those kinds of things um but let's talk about crypto for a second because I think that's Very interesting. Right? So, you got these big cap tokens right now. They're starting to take off, right? Daily they're going up maybe 5%, 6%, right?

34:51 Which is great. We're in a bull market. Everyone sees XRP taking off. They see Ethereum taking off. But guess what they don't see? They don't see the ecosystems underneath those coins that are still at rock bottom prices, right? And once that liquidity fills up those big caps, guess where it's going to flow? it's going to flow right down to the small caps that support those projects. So, right now, I'm scooping up as much of XLM I can. Eland, I'm a huge X XRP uh believer that always do your own research. Don't take my financial advice, right? But this is how you need to be thinking. You don't want to look where everyone's looking. You want to look where no one's looking, right? But understand how these things work. AI.

35:37 So, I found um I'm also an LP in another company um with a gentleman named Howard Gets. So, you know Howard, he spoke at at Garrett White's uh mansion. So, um Howard has been the CEO of a AI company for 33 years. Um and we have a team of 20 PhDs and what we do is we AI enable businesses. We take, you know, old school businesses that might be doing, you know, low eight figures and we help them get to a nine or even 10 figure exit. Um and we come in and like this is not chatbt zapier integrations. This is like real stuff. So like one of the uh highlight products that we've developed is a trading algorithm that trades commodity futures. And uh it's literally thousands of AIs that talk to each other to figure out the the next best trade.

36:25 And we actually created a patent. So if you're a trader, if you're familiar with trading, um let's say you you know trade gold, right? and uh you make I don't know a hundred bucks by by long by shorting gold. Well, you would take that money, a human has to take that money and put it into another trade, right? Well, we created a patent called real-time curve hopping where the AI takes the investment and puts it right into the next investment without a human involved.

36:52 And we own that. We own that patent. So our our trading algorithm is able to get um 33% a year conservatively with a half% draw down. So you never experience 10 20 30% draw downs like you would in S&P or even you know volatile crypto markets. So those are the things that I'm super interested in that I'm investing in today. I also hold some real estate. There's some some guys I know that you know have big real estate syndications and funds that you know have a good chunk of cash in that when they appreciate I'll get my money back 20% and 20% plus

37:26 one or 2% ownership of the fund as well. So what about investing into yourself coaches courses masterminds mentors walk us through why some people out there should be investing more into themselves.

37:38 100%. And that's actually probably the most important one. You know, if I could go back, um, I spend at least six figures a year just investing in myself, masterminds, hosting dinners, bringing people together that are smarter than me so I can learn from them and make deals happen, right? So, um, it, you know, obviously if there's somewhere you want to be, you have to go to places that where people are doing it, right? And get around smarter individuals. Like we I spoke at Thank you so much last night. you had elevator nights and I spoke there and um you know my ever since I met you I've just kind of modeled your uh kind of like your strategy on how you bring people together you host a dinners you always have a reason to when you go to a new city you have your group chat and you know who's there like bro you know hey we're having a dinner right so I'm actually doing the same thing thanks

38:28 to you and my strategy is like just follow you all over the country you're bringing amazing people right so um you have to have mentors. You have to have people that you look up to that are uh where you want to be, right? Um and I think that it's really important too that you always have to keep it what's in mind for other people, right? Um my one of my good friends, uh Joe Polish, I think you know, right? Um he wrote a book called What's in It for Them? And the whole premise of the book is giving value before receiving. It's like you have to treat people like ATM machines, right? You can't make a withdraw before you without making a deposit. So I kind of look at the same thing as as relationships as well. And uh so investing into yourself um through your personal education and I'm not talking about you 100% if you want to you know go to college get a degree be a nurse be a pilot be a doctor we need those things

39:22 but in our our our savvy u uh progressive world with social media and internet marketing and and this create creator economy. There's so many ways that you can learn from home and you know on YouTube and find people like yourself or other people that are movers and shakers that are bringing people together that are doing big things to learn from. So that's that's why I really like what you do here the panel you bring everyone together and able to share strategically in 60 seconds. So yeah. So on the charity side, why you think it's important for people to have some type of charity that they do with their household, whether that's their kids family friends etc.

40:05 That's uh it's so important. So I'll tell you the here's part of my story of why I got into business. Um I I did want to have a family, right? I wanted to live life eventually on my own terms, right? But um it was it was back in early 2015. and I went on a deployment to Papa New Guinea, Fiji in the Philippines.

40:26 And uh we were literally building schools for kids. Nice. And it was some of the most like amazing work even to this day that I've personally ever done. And I just remember on our last day in the Philippines, we had just built these, you know, uh four um wall structures with a roof. I mean, they had they they were like in little tiki huts and like it was just completely third world. And we built them basketball courts. um uh soccer fields like the whole nine and I just remember on the last day um I was walking there with the CBS and I'm a corman right so I'm supporting CB so if they put a thumb you know a nail through their thumb I'm the guy that helped them right but I just remember walking up there with boxes of literature crayons and all the stuff and we had to walk up this like steep steep hill so you don't see the site until you get up there right so I just remember going up there right when I get to the top man we see

41:17 literally like hundreds of kids hundreds hundreds of kids and they just came running up to us and just saying, "Thank you. Thank you, USA. USA." Grabbing my leg, dude. It was like I get goosebumps thinking about it cuz it was like, "Oh my gosh, the impact we're making for these kids, right?" So, it was at that moment I and I had just put on E6. Like I said, I made it in 5 years. It takes the average person 12 years. And I'm like, I think I did all I could do in the military. And I want to figure out a way to make money so that I can not only give with my time because I'm limited to my time but if I had more money I can create bigger impact right so a couple of organizations that I'm a part of today um which I believe you know of at least one of them is uh pencils of promise who build schools with kids from Mexico

42:01 one school's like 25k I think we built nine schools so far I I continuously give a percentage of my my uh revenue to that organization since um since Cole Cole Hatter was the when I went to Thrive Make money matter in uh 2016 in San Diego. That's when I first learned about the

42:20 So um and then uh RIP Medical who they help military veterans eradicate military medical debt. So

42:28 I'm a huge believer in that because I I served in the military. Um I deployed and I saw the the hidden wounds of from combat PTSD and all the things. And these guys, you know, they get out the military and they don't have the medical care and they don't know how to get rated properly. When you when you're going getting out the military, you have to go see multiple doctors and let them scan you and analyze and you have to ask certain questions. You have to complain about certain things. And if you don't, you won't get the rating and the money and the the medical that you're you're, you know, that you should be getting for serving your country, right? So, a lot of them get out the military and they're having to get seen for all these wounds and there's no financial support. So, you know, RIP Medical, every $1 we raise eradicates like $10 in debt for them.

43:16 So, um you know, and just overall, you know, seeing this work that I do through these charities and we do plan on having our own foundation that we're actually working on right now. I just started a

43:29 501c3. I always get the number messed up. Nonprofit. Um, but uh, yeah, it's it's it's actually a Christianbased here

43:39 in in California. And we're working with a lot of Christian entrepreneurs, military veterans as well. We're just starting, but there's a lot of great work that we're going to be doing with that as well. And that's going to be really the legacy I want to leave for my kids, the story that they're going to tell about me when I'm gone and the things that I did here. So,

43:55 so there's only one question that I ask on every single episode, and I've never gotten the same answer. over two years. Douglas James, you build up LeadFi to become a billion dollar company. You invest in other deals and all of a sudden you've got billions of dollars net worth. But unfortunately, at some point, you pass away. What percentage of that net worth do you leave to those children?

44:20 The children that I help, your children, to my children, or other people's children?

44:25 That's a good question. That's why I ask it every single time. God dang. You know, I guess I have to walk myself through this thought because I want my kids to know the value of money. I want them to know how hard it is and the work and the commitment and the blood, sweat, and tears that goes into creating like something like that. At the peak of my coaching consulting company, it was like the highest of the high, but it was also the highest stress environment I've ever been in in my life. um military being deployed, right? And I that's a good question, you know, and I would definitely leave them something. I would definitely leave them something, but I feel like a majority of that money would need to go to some type of goodwill to support the organizations, charities, and the things that I've been a part of that I was building. So, I probably wouldn't even leave it to them in their personal name.

45:31 I would probably keep it in a trust and to a nonprofit that they would eventually become the secretary or president of, right, strategically for tax reasons. That would be a great way, right? Um, but I I would want that money to continue to support the mission and the vision that I had left when I was gone. And my goal is for our kids to be a part of that as well. So, that's my answer. So, where can people find you on social media where can they check out LeadFi and the things that you're working on?

45:59 Yeah, go go go to Instagram. Just type in Douglas James. I should be the first one with the blue check. Um, you know, I think the I think the handle is the Douglas James. And then the website to LeadFi is uh leadfi.ai. Go check it out. Schedule a call. We'd love to help you out if it makes sense.

46:18 Guys, you're listening to the Money Mondays where we cover those three core topics. But it's very important for you to have discussions with your friends, family, and followers about money. We grew up thinking it's rude to talk about money. I think that's absurd. It's ridiculous. We have to have a discussion about money. Money is not the root of all evil. Money can help you with your family, your friends, your bills, travel, medical, and all the things that take to run your household, your life, and the people in your circle and beyond. You can do a lot of great things with money when you have the open discussion about it. and you don't want to have people go get the wrong salary or take the wrong loan or get the wrong debt or get the wrong this this and this because you just didn't talk about it.

46:53 So, learn about it. Thank you for listening to Money Mondays where it's you can learn bits and pieces week after week in these 30 to 40minute episodes, but research the things that you care about. Get as well knowledge you can about money and we will see you guys next Monday on moneymunddays.com.

Questions about this episode

Who speaks in "How Real Estate & AI Tech Are Creating Millionaires: Lessons from Gary Lipsky & Douglas James"?

Dan (Guest), Gary Lipsky (Guest), Douglas James (Guest).

What is "How Real Estate & AI Tech Are Creating Millionaires: Lessons from Gary Lipsky & Douglas James" about?

The discussion centers on the intersection of real estate investment and artificial intelligence technology, highlighting how these fields can generate wealth, with Gary Lipsky sharing insights from his successful ventures in building a real estate portfolio through Break of Day Capital. Key points include the importance of strategic investments, tax benefits, and the broader impact of real…

What is mentioned in this The Money Mondays Podcast episode?

18 people, works and ideas are mentioned, including Douglas James, LeadFi, Break of Day Capital, Gary Lipsky, Dan (Money Mondays host), Artificial Intelligence. Each one on this page links to its own page with every episode that mentions it.

How long is "How Real Estate & AI Tech Are Creating Millionaires: Lessons from Gary Lipsky & Douglas James"?

The episode runs 47 min; the transcript is about 9,171 words in 92 timestamped sections.

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