1387: Investors Are More Eligible, Timing the Market & Cash On Cash
7 Dec 2025 · 35 min
Jason Hartman discusses whether owning property makes you more attractive to date, then tackles timing the market versus buying now. The panel weighs cash-on-cash returns against interest rates and short-term rental income, and defends a buy-and-hold strategy even when buying near a market peak.
Chapters
My goal is maybe get into real estate, also help my friends do what I've been able to do and spend more time with my family.
Welcome to the Creating wealth show with Jason Hartman. You're about to learn a new slant on investing, some exciting techniques and fresh new approaches to the world's most historically proven asset class that will enable you to create more wealth and freedom than you ever thought possible. Jason is a genuine, self made multimillionaire who's actually been there and done it.
He's.
He's a successful investor, lender, developer and entrepreneur who's owned properties in 11 states, had hundreds of tenants, and been involved in thousands of real estate transactions. This program will help you follow in Jason's footsteps on the road to your financial independence Day. You really can do it. And now here's your host, Jason Hartman with the complete solution for real estate investors.
Welcome to episode number 1387. 1387. And thank you so much for joining me today. Wow. It has been absolutely crazy life lately. So think about where I've been and what I've done. It's just been absolutely like head spinning. Does your life get like that sometimes? I'm sure it does, but probably in a different way than my own. So a few weeks ago, I was in Kansas City and I learned how to throw an axe because there's this place you go for dinner where you do ax throwing. And I was actually pretty good at it. If you happen to be friends with me on Facebook, you might have seen it. Or if you happen to, I believe it's on the JasonHardtman.com Facebook page or commercial page too. So even if you're not friends with me, you can go see it there and you can see me throw the axe. And I swear it was the first cut. I did not do another video of this. The employee there held the phone, held the camera, and I threw the axe. It hit the bullseye right away from like 20ft away. Nice firm throw right in the bullseye. And then he went over to the side and got me from a different angle. And I did it again. I couldn't believe it. Hey, beginner's luck. Maybe, maybe not, I don't know. But it was pretty good. All I did before that was he just showed me how to throw it a couple times and I did it like three times. And then we videotaped and there it was. So I went from freezing cold Kansas City where it was 20 degrees, and then I came back home. I was here for a couple of days. I went on an Eight day Caribbean cruise. It was a business cruise. It was not a pleasure cruise. Hey, it sounds like a lyrics to a Queen song. Isn't that like a Queen song that says life ain't no pleasure cruise or something like that? Yeah. Anyway, so I did that. I came home for 19 hours. Then I flew to Aspen, Colorado. I got a little sick, which was a real bummer. I guess my body did not like the temperature change. I came back, I was here for just a couple of days and then I went to Sarasota for one of my mastermind group meetings. Not my own mastermind group, another one that I'm a member of. And that was great. And then I spent the weekend in Tampa after that. Got to see Naresha's new baby and. Well, I guess it's not. It's only half Naresha's, right? It's half his wife's. As if the baby is property. But yeah, I got to see their new baby, I should say. Then I came home last night and here I am. Oh, I'm tired. It's a little tuckered out. Anyway, hey, we got some great stuff for you today. First off. Well, what should we do first?
First, first, first.
Let's go.
Go first.
Well, let's talk about romance because we have a very romantical day coming up and that is Valentine's Day. It's on Friday. And what does this have to do with real estate? Can we tie the two together? Well, probably, if you're a. If you're a real estate investor or a homeowner, and those are different things, by the way, you're going to be considered a more eligible mate. So that's for sure. So, you know, in the old days it was like all about property. And I tell you, human nature hasn't changed too much since the old days, has it? Because everybody still likes property. And this is, you know, maybe it's a little bit skews to more women are more attracted to successful men, but hey, nowadays, you know, it's more modern world, right? So that equation goes both ways. You know, if you're single and you're a guy and you're looking for a female, I can't make any assumptions, by the way. You know, I was looking at a house over the weekend in Tampa and the realtor's showing me the house and she says his and her closets. And I go.
You can't say that anymore. You can't say things like that. That is a discriminatory remark, you know, could be hers and hers or his and his, you never know, could be whatever, right? So you got to be careful with these assumptions, right? It's just all baked into the language. And you know me, I'm not big into political correctness. But hey, some things are just right and wrong, right? Anyway, people with resources are more desirable mates, right? So buy some more properties. You'll be a more desirable mate even if you're already taken. Right? Because your mate will still desire you more. Right. If you're more successful. But what about love, right? What are the best cities for dating in the good old US Of A? Well, this is a real estate article. It was published by apartmentlist.com and Rentonomics. And according to them, which I take all of this stuff with a grain of salt, but it's kind of, I don't know, kind of. I think some of it's pretty accurate. Some of it. I would take issue with having lived in many cities and bend almost every city, you know, and being technically single, you know, from a marriage perspective at least all my life. I don't know. I'm not so sure. So you tell me what you think and go to jasonartman.com ask and tell us if you agree or disagree with this stuff and ask any questions about it. But the top 10 best cities for dating in the good old US of A. I'll go from the bottom up. Many of these have been our markets. We've been in in these markets over the years. We've sold many properties in some of these markets to clients who have done very well, maybe certainly on the money scene, maybe on the dating scene, too. Number 10, Grand Rapids, Michigan. That's a market we've definitely done some business in. Chattanooga, Tennessee. Number nine, Houston. Number eight. We've done lots of business in Houston. Hundreds of transactions over the years. Denver, Colorado. We used to recommend the Mile High City, but hey, it just got a mile too expensive for us. Wow. Can you imagine our clients that purchased from us in Denver back in like 2007-2008-2009-1011, 12. Probably. Probably. 2012 was the last business we did in Denver. They made a fortune. You guys made a fortune. Congratulations. Aren't you glad we met? That was a very profitable meeting, meeting us. Right. Discovering my podcast made you a lot of money. Share it with your friends and family and they'll be happy you did okay. Pittsburgh, Pennsylvania. I used to live there when I was a little kid. Number six, Knoxville, Tennessee. Number five. So Bridgeport, Connecticut. Number four. Way too expensive. We wouldn't do that market. Raleigh, North Carolina, We've done some business there. Long time ago in a galaxy far, far away. Again, another market that got. But our investors that are already there, they made a ton of money. Richmond, Virginia. Number two. Provo, Utah. Number one. Number one. Probably the big Mormon community. Really, really helping with that, I bet. Worst cities for dating. Now, this is not for investing, but for dating. Okay, so North Port, Florida, the worst. Deltona, Florida. We've done lots of business there. That wasn't so good. Lakeland, We've done business there, too. New Haven, Connecticut. Have not done anything there. Buffalo, New. Nothing there. Syracuse, New York. Harrisburg, Pennsylvania. Worcester, Massachusetts. Spokane, Washington. I'm surprised that's not a little better for dating. Maybe it's just raining too much. Birmingham, Alabama. We've done a lot of business there. Not good for dating. So if you're single, you know, feel free to invest in those cities, but do not move there because you will be lonely, lonely, lonely. And you don't want to be lonely. That's no fun. Okay, so then they divided this up. Male versus female. In other words, where were men most satisfied with their dating lives? Versus where were women most satisfied with their dating lives? And I won't read you all of them because it'll take too long. You know, we gotta go both sides of the list twice, Right. But we'll put a link to this article in the show notes. How's that? And you can look at the charts and read the narrative and all that stuff. But the number one best. Well, I'm gonna do the top. The top four for. Well, the top. I don't know. Maybe I should do the top six. I don't. There's too many. Okay, I'm just gonna say it. Number one, best city in the US for men. For dating. Which actually really quite surprises me. I lived there and I. I don't agree. I don't agree. San Diego. San Diego, California. The Socialist Republic. Number one for women. This one I guess I can see. Columbus, Ohio. Yeah, Columbus, Ohio. Women said they were most satisfied in Columbus. Men said they were most satisfied in San Diego. Number two for both genders. Denver for men. Houston for women. Yeah, I could see that. Number three, Houston for men. Now, that's interesting, because Houston, both genders were pretty happy with their dating life. See, that's an affordable area. No one's under too much stress. Yeah. Okay. Go to the Galleria Mall. You know, it's. It's nice there. For women. Boston, Massachusetts. Boston. They're parking the car. And Harvard Yard. Okay. Virginia beach for men. Atlanta, Georgia for women. Okay. St. Louis for men. Denver for women. Denver coming in at number five for the women. Number two for the men. Up on the list there and then Miami for men. Cleveland for women. Washington D.C. for men. And also Washington, D.C. for women. On par. Wow, those two, that's like a tie. Boston for men, where it was way up on the list for women. A little much lower for men. Philadelphia for women. Charlotte for men.
Charlotte, North Carolina.
We've done lots and lots of business there. Minneapolis for women. Milwaukee for men. Charlotte for women. Interesting. Anyway, this is a little hard to understand without seeing it. Then they've also got best cities for dating based on education level. You don't want to date stupid people, that's for sure. Best cities for dating from the full data set with all of the male, female satisfaction, the education level, et cetera, et cetera. So just kind of interesting tells about the methodology. We'll put a link in the show notes to that one. Hey, let's take a quick break here. I want to play for you a little discussion segment we had at one of our live conferences. And then I am going to come back with more, more to come right after this.
Carrie, one of the things I know and feel free to just answer any frequently asked questions from the stage that you're getting from clients, but a couple.
Of them that you brought up and.
Take what you want. You know, investors trying to time the market. You always get people saying, well, I'm just going to wait till the next crash and then I'm going to buy everything.
This does not work, just so you know. But people try it. It's just sort of an irresistible tendency. I think we all have as humans. We want a deal, right? So waiting for better returns or investing now, I mean, obviously the returns five, eight years ago were much better than they are today. Prices are higher and it takes a while for those rents to catch up.
Speak to.
Well, yeah, so I mean, five years ago they were probably double the returns you're getting now, but a year ago they were less than you're getting today. So it is a cycle. It goes up, it goes down. You just need to know which market to be in and which market is good for your investments. Right now we have three great markets, four great markets are here today that are all performing well today that you'll get into today or in 2020 when they close. I know you're probably saying you're prone, but why wait? You know what? Get in now because the longer you wait, the longer you're going to see a return on anything. I mean, why wait?
So that's a good point. So one of the things I always see that people fail to calculate is let's just say you could time the market and say you could do it beautifully. You'd wait three years and then the recession finally comes. And the recession will come. It'll definitely come. It's always a cycle. But the thing investors don't see is that they lose the returns during that period. They're waiting. That's what they almost never calculate. You know, we talk about how you can't hear the dogs that don't bark, and that's one that definitely doesn't bark. Granted, you could have that investment in something else, but pretty much everything is influenced by the recession.
Right?
And when that cycle does come and when that cycle does hit, things will go well until they don't.
Okay.
And people rarely calculate the returns they're losing. Oh, Coco, this is really good. That's definitely a thing that conversation clients have, right?
Yeah, exactly. And I'm going to take Tyler's deal. Interest rates, do I get it locked in a rate now? Do I go later? Nine months ago, he was locked in at a 6% rate and Joe's refinancing for him and he's going to get an extra 50 to 75amonth now in cash flow. So again, he didn't wait, he went for it. He got the property. And now nine months later, he's doing 20% better on his returns.
So, Kerry, in that newsletter, that should have been in your packet, right? If you look at the high five indicators on the front of it, and I don't remember the exact number, but I think it is the median mortgage payment right on the front page. And it shows that. I think month over month that mortgage payment went down by $26 just because of the change in interest rates. So isn't that interesting? I mean, a $26 a month savings in the course of one month. Okay, so there's obviously a lot of factors that go into that. But Jim, do you have any thoughts on the timing the market? I mean, you talked about it broadly, but this idea that people can do.
It.
I think that you're always timing the market what works now, because I've had so many people that they went to six classes. Thanks for inviting me. I'm just about to pull the trigger on my first investment property. You have friends like that? Sure, more than six.
They've been going to seminars for their whole life.
And they can tell us more about the strategies than I can but they haven't pulled the trigger. So I think there was a unique time where it was maybe 2007 where it was just you shouldn't be buying that was there. But timing the market. I think you have to look at fundamentals. If there's fixed interest rates, there's cash flow. I've always worked in growth markets. Bakersfield was a very big growth market when I was there in the late 90s and early 2000s. I think you have to follow the trends of the markets you're going into individually and look at what is cash flow today. Warren Buffett talks about intrinsic value. What's the intrinsic value you're getting in at a good price per square footage? Are you getting in an area where the affordability index is healthy? There's things to look at when you look at that now that's what I look at and people say oh, it's not good. Well if you're comparing it to 2010, that was a very unique time. 2009, very unique time. The returns are still really strong where I look at it. Timing the market is saying can I get into for now my eyes can I get into a new construction property for a double digit cash on cash return today at a good building cost per square footage? And the answer is yes. So timing the market is you can't base it off of what was available. Oh I wish eight years ago. But does it work today? Is it sound today? And when you take that part of it out of it, I think that you can see that. So I kind of focus on the now because otherwise if I'm going remember that deal I did in 2009 that was that then you kind of.
You'll never do it. There will never be a crush it.
Right.
You crush everything else.
But you know when the fundamentals are completely out of whack and you're forced to be a speculator rather than an investor, that's when you shouldn't be doing it.
Yeah.
And again that that grow rich with the property cycles things, you know the invest. They will be saying like when I was in Bakersfield in 2005, so these were houses that I bought for 50 and it was selling for 185,000. But they were only renting for 950.
So they're only running for a 0.5 RV ratio.
That's terrible.
And these were houses from the 1940s. So they were, you know, they had higher maintenance and repairs. So when you look at it didn't make sense. I Mean, it was very.
By the way, you just made me think of something that I think is really relevant to what you do. Because you have long term buy and hold rentals that make sense with good RV ratios, but you also have short term rentals that are largely marketed on Airbnb.
Yeah.
And interesting tie into our conversation this morning. When you look at the bits and bytes, think about how just one company, of course there are others, but Airbnb is the flagship, made so many properties so much more valuable because it opened up whole new market of properties that would not qualify as legitimate smart rental properties before. And it made them work on a cash flow basis because when you rent a smaller slice of that property out, in other words, night by night or weekend by weekend, or week by week, whatever, you can charge a higher premium. So the bits and bytes of Airbnb took something that was the same atoms. They didn't change. The properties were already there. Right. They already existed in the marketplace, but just the way it was delivered, in small slices rather than monthly slices or annual slices. In other words, a monthly rental or an annual lease, if you could lease that property for a couple of nights, you could charge a premium for that like a hotel does. Right. And so the bits and bytes, the information economy, change the value of a whole slew of properties. Yeah, it's pretty incredible.
Well, and I think as an investor, you have to be open to that, because if you get something stuck in your old ways, you're not going to grow. I think that you always have to be keeping your eyes open as an investor, because things have changed from what I was doing 22 years ago or you were doing. It's a little different for different things. There was no such thing as this short term for the most part, but I stay open to that. So everything that I've done for growth wise, even the fact of working with investors like yourself, post meltdown, when we got approached, I was like, I do my own deals. And then started working with Jason and the gang and then looked at the short term rentals, then new construction. So I'm always trying to. I think you want to have your core, but you want to be able to branch off of that core and be open to these things that are coming down the line. Not shiny pennies, but things that have fundamental sound principles that are working and it'd be silly to ignore them.
Yeah. And you know, that's a fair statement because we need to see the Airbnb economy go through a recession. Hasn't happened yet. Okay. So, you know the short term rental industry has been around really since the early 70s. You know, it's been there, but it's there in a much bigger way now. So it is. It's not something to do with all of your portfolio. It's to do with maybe 20% of your portfolio.
Yeah. Which is what we talked about. That's where I think that.
Okay, good, good. So, Naresh, I want to ask you about some common misconceptions about local markets. Metrics to consider on the pro forma. Before the break, we asked everybody what metrics they like the best. How about you?
Yeah, well, I think most people said cash on cash. I will get cash on cash return, but also rent to value ratio. Obviously the 1% rule. One thing that I wanted to add about timing the market, my one regret is that I didn't get in sooner. So as I said earlier, I got in about two and a half years ago. I've known Jason for seven years. I should have gotten in the moment. I met Jason in 2012. But I was one of those people who was thinking, oh, there's going to be. I would read the mainstream news and I would think there's going to be some kind of recession. There's going to be a double dip. And so I just waited and I waited and I waited and it wasn't until talk to Jason a little bit more. Then I said, you know what, it's time to jump in. There are still some values in this market and if I don't jump in now, then I'm never going to jump in. And talking to some of you guys over the past couple of days, I heard some of you, you said that you just found Jason a few weeks ago or a couple of months ago and you're looking to buy your first property, but you're also waiting for that next recession. And we know it's going to come, but it's just, when is it going to come? Is it going to come next year? Is it going to come in five years? We have no idea. So again, my recommendation, just like the other panelists have said, is if you find a good deal, go ahead and jump in. Don't just blindly buy anything, but just go ahead and jump in. And the team here, my investment counselor, when I got started with Sarah. Sarah, the investment counselors, the property managers, the lenders, Jason and his company have all those contacts and they help guide you through that process. So there's really nothing for you to be fearful about.
I hope you enjoyed that discussion. And I have a listener question From Archie. And Archie, I believe you have sent some questions to us before through jasonhartman.com Ask and what is on Archie's mind is a common concern and it is a good concern, but it represents only part of the equation. So here's what Archie said in a nutshell. He says, I'm concerned with investing in a housing market top. I believe there is more of a probability that prices will decline rather than increase in the short term. Not sure what short term is, but okay, I understand that inflation is the upside of the 30 year fixed rate mortgage. Single family, 3 bedroom, 2 bath, 1% RV, rent to value ratio below cost to construction, linear market investment. How do you weather the storm with this investment strategy? In a deleveraging deflationary scenario, how did this strategy do if you bought in 2006? Are there any other downside risk that I'm unaware of with this investment strategy, like opportunity cost? Would it be better to save your liquidity for an illiquid market? Bottom. Okay, great question. Here's the thing you gotta understand. You can't talk about a housing market top. Because the question is where, where, where, where? You know, I sound like a broken record talking about this stuff, but look, if you're thinking of investing in New York or the Socialist Republic of California or Washington state or the Oregon coast or, you know, South Florida or any of those expensive northeastern markets, this is a valid, valid concern, Archie. If you're in some of those markets. But if you're in these boring linear markets in the Southeast, the Midwest, some, not all of what people call the smile states, okay? In other words, if you're looking at a map of the US and you put a smile on it, that kind of crescent shape of that smile, most of those markets are pretty good. Not all of them, okay? Be careful because you don't want the edge of the smile on either side, okay? That's where you might get hurt. Especially on the west coast side of that smile. That's gonna, that's gonna hurt you. But most of that is gonna be pretty solid because remember, you're not investing for capital appreciation. Even if it depreciates. Who cares? Really? Who cares? You're not selling anyway. I mean, of course we would all rather have our properties appreciate in value, obviously, but it's not a big deal. It's not why we're investing. We are yield oriented investors. Look, in the bond market, for example, you can buy bonds and hold them for the yield, okay? Or you can trade bonds and try to make capital gains on those bonds. You can buy a dividend paying stock and you can hold it for the yield, the dividend it pays, or you can buy a non dividend paying stock and just try these very simplistic, very bad strategy of buy low, sell high. We're investing in a multi dimensional asset class. We are investing for yield. We are buying prudent, low cost properties, properties that have universal need, that are below the median price in any given market almost always. And these properties are just in demand. Now you asked a very good question here, Archie. How did this strategy do if you bought in 2006? Great question, great question. Okay, here's why that's such a great question. First off, you have to realize that the Great Recession that came right after 2006 was the worst economy in a lifetime. The worst economy in seven decades. It was an anomaly. Of course we're going to have other recessions. Of course we're going to have other market crashes. Obviously there is a cycle, there is a business cycle, there is an economic cycle, there is a recessionary cycle. We will have another recession. Hey, if Trump isn't reelected, the party's probably going to end pretty quickly after that, okay? If we get a delusional old man socialist like Bernie Sanders who, hey, listen, he probably means well, but he's just delusional, okay? You know, Elizabeth Warren, Hey, I kind of like some of Elizabeth Warren's stuff. You know, I like how she attacks the banksters and the Wall street crooks and all of that stuff. But you know, her plan's gonna be a disaster, okay? And then you got the Donald, right? And I mean, he just keeps saying things that like, offend everybody. And it's, it's sort of funny. It's very entertaining, actually. But you know, why does he have the. Why does he have to offend everybody? Seriously? Because, you know, if you just look at purely his presidency, at the very least how he's handling the economy, God, give the guy some credit. I know the media won't, but I mean, this is the biggest economic expansion in history, okay? You had huge expansions under Reagan, the largest peacetime expansion in the history of the country under Reagan, and then you had it again under Clinton. Now, Clinton was a little bit different, okay? Even though I did not like Slick Willy, Bill Clinton, he's a, he's a total crook. I gotta give him some credit. Like, try and don't be so partisan all the time, people, okay? That's what I'm trying to say. Like, give people some credit where it's due, right? Clinton where's it due? Look, it didn't really jive with his beliefs, okay? But he, to a reasonable extent, didn't mess the economy up. He didn't screw it up. He didn't interfere very much as like, Obama did. Obama interfered way too much, okay? Clinton sort of just was a little bit laissez faire about the economy, which I love. I was totally in agreement with that. And also he had the extreme good fortune of presiding over an economy that was just ramping up in a huge way. Globalization. And that put downward pressure on prices, so consumer goods got a lot cheaper. Now, it took a while for all the Americans to lose their jobs because of this, right? But that eventually happened as these terrible trade deals that Clinton presided over took effect. And as Ross Perot said, that giant sucking sound. But the other thing that Clinton was so fortunate, and I know this is going to sound silly, but the fax machine. The fax machine, yes, the facsimile machine. That was a big deal. I don't know if you really remember how that sped up the velocity of money, the velocity of commerce. We had fax machines before Clinton, but under Clinton, they really caught on, okay? And you saw the result of the humble fax machine in the economy. Now you're probably thinking, Jason, you didn't even mention the Internet, the information superhighway. Well, obviously that was way bigger than the fax machine, but I wanted to give you the preamble to it, and that was the fax machine. Do you remember how slow commerce was before fax machines? And how it just totally sped up with the good old humble fax machine? And then, of course, that Internet thingy, majig. Well, that was a pretty big deal. And Clinton, he was in the right place at the right time. I mean, that just obviously changed the world so dramatically. And we're still reaping the incredible, incredible profits of the Internet age. This world of frictionless e commerce that, you know, remember, one of the things economists talk about a lot is the velocity of money. The velocity of money is a big deal because when you have more velocity, more trade, you increase the size and speed of the economy. So that velocity, just making things simply move faster makes people more prosperous. Doesn't have to be that everything else is right. Just increase velocity and you'll increase the size and scope of the economy. And the Internet gave us this world of largely frictionless global e commerce, which was just obviously incredible. I don't have to overdo it on that. So, Archie, back to your question. Just buy good properties in these good linear, solid markets and keep them and stop trying to time the market. At the very worst you're going to lose the opportunity cost because if you have to wait three years to try and time a market bottom or five years or seven years, who knows when you'll see the bottom. And trust me, when you're there, you won't know you're there. That's the other problem. And when you're at the peak, you won't know you're at the peak. We don't know we're at the peak. Now. I certainly don't believe we're at the peak in any of these linear boring markets. Now if you're telling me about cyclical markets like la, San Francisco, New York, Miami and many others, you know I'm going to say don't touch them with a ten foot pole. But I wouldn't touch those anyway because they don't make any sense. They don't get a 1% rent to value ratio or even close. So you're going to lose. I mean if you go to Jason hartman.com properties right now and you look at the performas on our website and you find a property performer, that all in is going to generate a conservative return for you of say 22% annually, 25% annually. Okay? You wait three years, you're going to miss 75% return on investment. Okay? Now say the prices do go down by 20%. Okay? You're going to lose more by waiting. The likelihood is you are. I mean, what are you going to do with your money till you wait? Stick it in the stock market. Well, it's easy to argue that the stock market is at a top, right? That's much easier than arguing that linear real estate markets are at their peak. So you're going to put it in the stock market and lose your principal there. You know, this is, this is not a winning strategy. Timing the market is generally for anybody just simply not a winning strategy. So buy good properties, hold onto them. It's the most historically proven asset class in the entire world. Just don't buy in the crazy cyclical markets. And if you're really concerned about a market crash, don't buy in the hybrid markets either. Get the really, really conservative bread and butter properties in the linear markets and you should be in good shape. And you can find those@jason hartman.com and we gotta wrap it up for today. Archie, thank you for the questions. Other people go to jason hartman.com ask tell me why I'm right or wrong or ask your questions, make your comments, share an article, share a link, whatever. We'd love to see it. We'd be happy to talk about it on the show too. And until tomorrow, happy investing.
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