
Three investing masters reveal unconventional wealth-building strategies that challenge traditional financial advice, from social media trend investing to real estate cash flow tactics to the radical "Die With Zero" philosophy. These proven methods show you how to build wealth while actually living your life instead of just saving for someday.
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Lewis Howes
I have a brand new book called Make Money Easy. And if you're looking to create more financial freedom in your life, you want abundance in your life and you want to stop making money hard in your life, but you want to make it easier, you want to make it flow, you want to feel abundant, then make sure to go to make moneyeasybook.com right now and get yourself a copy. I really think this is going to help you transform your relationship with money and this moment moving forward. We have some big guests and content coming up. Make sure you're following and stay tuned to this episode on the School of Greatness. The School of Greatness is proudly sponsored by Amica Insurance. As Amica says, empathy is our best policy. That's why they'll go above and beyond to tailor your insurance coverage to best fit your needs. Whether you're on the road at home or traveling along life's journey, their friendly and knowledgeable representatives will work with you to ensure you have the right coverage in place. Amica will provide you with peace of mind. Go to amica.com and get a quote today. If you've listened to the School of Greatness podcast for a while, you know how important acceptance is when it comes to personal growth. And you know who else is big on acceptance? Discover. You see, Discover is accepted at 99% of places that take credit cards nationwide. That's a whole lot of places and a whole lot of acceptance, which is great for Discover, but even better for you. Based on the February 2024 Nielsen report. Learn more at. Discover.com Credit Card GoldDealer.com provides one of.
Chris Sacca
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Lewis Howes
Five years making, you know, saving all your money, you invest it and then it's gone essentially overnight. How do you get over that mental and emotional loss and stick it out and kind of keep going?
Chris Sacca
You know, it's a great question. And here, and here's what I tell people. You know, any money that you have invested in risk assets, the stock market is a risk asset. You have to mentally, every time you check your account, reduce it by 70%.
Lewis Howes
Really?
Glenda Baker
Yeah.
Chris Sacca
Because that's your downside. Realistically, just realistically that's your downside. So from the first dollar you put in, you think your account's $100 account and it's a $30 account. You have to be willing to live with that risk account being 70% less. Okay. Realistically that's probably the lowest it's ever going to go in the worst of all worst case scenarios. Now before you sell it, theoretically go lower. Anything is possible in this world. We can disappear tomorrow. Okay, so like anything is possible, but for the most part your absolute like Great Depression style worst of all worst case scenarios, I like to think of it as down 70%. So bucketing money is one of the most important things for an investor to do. So I always talk about the fact that investors only really have two decisions to make. How much of their money they want to have bucketed and in risk assets and how much they want to have bucketed in safety being treasury bills. Right. Or just a Treasury backed cashing helm that's paying you 3, 4, 5% a year. Whatever, you make that decision and that decision changes over the course of your life. So when you're young, you might have 5 or 10% or maybe even 0% in the safe bucket, maybe you have 20%. And when you're old you might have 80 or 90% in that bucket.
Lewis Howes
Right? Right.
Chris Sacca
Everyone tries to overcomplicate wealth management. Everyone thinks, oh, it's really sophisticated. You go to a wealth manager, they'll hand you like an 80 page report. That's your like personal financial plan. You're like, dude, this is so sophisticated. It's all bs. The whole thing is bs. Like it's just a printed out load of crap to make it seem like it's sophisticated and you need all that assistance and help. Like for me, I have money that's safe and I have money in risk assets. That's it. And honestly, for most people, if you don't want to play the game of trying to beat the market, the money in risk assets could just be in AN S&P 500 ETF Exchange Traded Fund that is basically free to buy and cost you like 1/10 of 1% internal management fee every year. It's the world's cheapest way to invest. And you just put money in there every week or every month and you don't think about it. And then you open it up in 40 years and you're super wealthy. Right. Like super wealthy.
Lewis Howes
Right, right. And just keep it simple, Keep it simple.
Chris Sacca
Like I always tell everyone, like if you are just willing to start investing, there will be a moment in your life, more than likely when you wake up one day and you realize that you're making more money from your investment portfolio than you are from your job. I'll never forget the day that happened to me, and I was like, what was that?
Lewis Howes
Like, how old were you?
Chris Sacca
So amazing. I, I, I, I, I was. It was probably 2008, 2009. Ish. Because it was right around the time I wrote my book laughing at Wall street, and I had turned $20,000 into 2 million in three years in my brokerage account. And I was making a lot of money from my job at the time. I was making, like, over $200,000 a year, which back then was a lot of money. I was a sales guy, right. And that for. It just wasn't enough money for the life I wanted to live with my family and the things that I wanted to achieve in my life for other people. I'm like, a very, like, I have a foundation. Like, I have, like, massive dreams of doing some really big things for in the philanthropic world. And I was like, I can't live the life I want to live in the neighborhood I want to live in, do this for my family and achieve that for other people on $200,000 a year or even if I grow it to 300,000. And I didn't really see a way to grow it to, like, meaningfully higher than that. And I think almost every ordinary person, like, substitute those numbers for other numbers. But every ordinary person is likely in the same boat where they're, like, making this much money, and they know that if they really kill it, they can probably get to here, but almost impossible to get above that ceiling. And that's the problem. The problem is what happens is they start thinking, I need to start a business.
Lewis Howes
Okay, that's, that's the worst thing to do. Yes, yes.
Chris Sacca
So, so, so you get in that zone and you think, I got it. I got to start a business. I got to start flipping houses. I got to start doing this, doing that. And it's like, oh, I hate it. That that is the roadmap for almost every single person or interesting about that.
Lewis Howes
Sorry to cut you off there. It's interesting, and I understand it because that's what I did early on. I was like, I need to. At first, I was, like, trying to get a job because I was broke on my sister's couch, and I was like, I just need to make some money. I need to get a job. But I had no money, and I really didn't have Any expenses, living on my sister's couch for a year and a half. Also that I was like, let me go try to figure out how to make money on my own. And I launched my own thing on the side because I didn't have anything. I didn't have any responsibilities, no bills, no kids, no relationship, nothing. And I learned how to make money on my own without working at a. I guess a career or a job. And then I've just been writing that and figuring out how to make more money. But I don't think it is so time consuming. It's so challenging. There's so many ups and downs that. And it's rare to make a lot of money in the first couple years of running a business. There's so many costs that you don't think about that happen that it's just like.
Chris Sacca
It is hard, it's almost impossible. Listen, I. I own businesses, I own restaurants. I like. It is so hard, it's almost impossible.
Lewis Howes
And it's interesting you say that because that's what a lot of people think about. Let me go launch a business or a side hustle or something else when all we could do is just let me put some of my money into investments and let it make money for me without having to work harder.
Chris Sacca
Yeah.
Lewis Howes
Yeah, right?
Chris Sacca
Yes.
Lewis Howes
But it's, it seems so scary of a thing to do for people that have never done it because it's like, I don't know where this is going. Can I get my money out? What if it goes down? Then I've lost my money and then it. People retract, right? They're like, I don't want to do that. I'm just going to keep it safe. And so I understand both sides.
Chris Sacca
This is the biggest life hack. Nothing comes close. Literally nothing comes remotely close to this life hack. Forget about everything else in life and just start investing, period. You're done. And guess what? You don't have to spend any time if you don't want to. You can go do all your hobbies, do all of your stuff. Just start aggressively investing and you do not have to sweat the next 30, 40 years trying to restart yourself, your career, over and over and over again doing side hustles and, you know, lots of starts and stops and a lot of depression. And then what I think I see a lot of. Because, you know, my entire life is analyzing social media now for trends, right? That's what I do for my investing. And it's just a crapload of complaining from this generation, which I get it. I get it. If, if you don't know this life hack, I totally understand the frustration. You can't make enough money to live the life you want to live. And you see absolutely no, like, light at the end of the tunnel in terms of how you can make it happen. That is a really depressing place to be and it's going to cause you to get out and start complaining.
Lewis Howes
And you see other people living this rich life or posting like they have a rich life, whether they have it or not, seeming like they're happy with this lifestyle, you know, taking trips and adventures and flying private or whatever it is.
Chris Sacca
And see, see, that's the issue because everyone keeps talking about the income gap. Like we've heard so much about the income gap the last decade, decade and a half. How are we going to solve the income gap? You're not going to solve the income gap. It's not happening. You can make really small dents in the income gap if you want to, but it's a lost cause. So just stop, okay? Just stuck. Now, the wealth gap, that's a solvable problem. That is 100% a solvable problem.
Lewis Howes
How do we solve it?
Chris Sacca
Getting the entire world to invest. Every single person that you're trying to solve the income gap for, just stop and just focus on the wealth gap instead of trying to figure out how to make that person earn three times more than they're earning. It's not going to happen. Make small change, you know, try to help them still to maximize their career. That should all still happen. But teach them how to invest. It's not even teaching. Just convince them. You see, like I even hate that I just had to say the word teaching. You don't have to learn, you just have to be convinced. You just have to be convinced. And every single person has money to invest, Period. Now, I know people are going to hear me say that and it's going to like result in a stream of angry comments because they're like, this guy is just completely out of touch. And no, I don't have money to invest. Yes, you do. You don't have money to invest because you're thinking about every dollar as a dollar. But like, this is a big part of what I wrote about in my book a long time ago when I turned 20,000 into 2 million in three years. And I'm not saying that people can do that. That was rare. But absolutely, you could turn every dollar to a hundred dollars over a much longer period of time as an investor, just with compounding. And when you realize that once you believe that you'll start to think of every dollar is a hundred dollars, right? And so when you start to think of every dollar in your life as $100, it changes everything. So I don't care who you are, there is a point to which you are not making trade offs. You're not clipping coupons. You might clip $2 coupons, but you're not going to clip a 10 cent coupon. Well, all of a sudden when everything's 100x, you're clipping 10 cent coupons, you're clipping 50 cent coupons. You are, you know, I don't know, you're just doing all kinds of things differently in your life. You know, maybe you're mowing your yard now, maybe you're making your coffee at home instead of going to Starbucks. All the things that weren't quite worth trade trading off are all of a sudden worth making a trade off for. Here's the difference. That money that you save by doing all of those things, right, all goes into your investment account for risk assets, right? And so believe me, when you start thinking of Every dollar is $100 and it will be $100 at some point, you start finding money in your life. I don't care what it is. I don't care. Literally a, you know, there are people on YouTube, they're actually insane with how to find money, right? Doing all these crazy things and you're like, that is just way too much of a hassle to make an extra $3 or $4. But for $300, I'm doing it. And it is $300. Once you understand that by taking that money and investing it in risk assets over the course of a long period of time, that $3 is 300, boom. You're making 300 bucks in the morning, you're making 300 bucks at night. Doing this like you're clipping, like you're doing all the stuff, right?
Lewis Howes
It's like a game that in your mind, oh, how can I turn this $1 into $100? How many $1 can I find and put away into investments today?
Chris Sacca
It's just, it's a mindset change.
Lewis Howes
How long does it take in a risk asset to turn $1 into $100?
Chris Sacca
Listen, it's different. It's different for everyone. It's different for every period of time. I can't predict how the next 30 years is going to go, but I do believe that this is one of the most interesting times to be an investor because of the age of AI that's quickly coming for us. So in one way to think about this is our human labor to some extent is a little will for some period of time might get devalued, right? If, if we're creating a new industry and that industry is the industry of intelligence, historically that's come from us, right? So now there's an industry of intelligence. And if that industry of intelligence is going to devalue human intelligence, then what do we do as humans? We want to invest in the industry of intelligence and we want to invest in, in the way that, that is going to impact the world positively. So this new industry of intelligence that we call AI and automation and robotics and all the stuff that I'm really into right now, that is going to make our entire world incredibly more productive, right? It's going to bring us efficiencies that we just didn't think were possible in our lifetime. Meaning that enterprise industry is going to become way bigger and way more profitable than it ever has. And we can make money off that by simply owning a piece of it. So you just, you, you asked me earlier, you said, what does investing mean? It just means owning a piece of the world. That's all that it means you want to own something more than yourself, you need to invest. Okay? So once we start investing, we start owning a piece of, of that thing that we hate and we like to about, okay? So it's like all of a sudden, you know why guys like me don't complain that much? Because I own all that stuff. So it's benefiting me, but I actually want everybody to own it. I hate that I'm making all this money off of industry. I'm making all this money off of technology advancements. And all of these other people are not just because nobody like taught them or convinced them that that was something that they needed to do.
Lewis Howes
Interesting.
Chris Sacca
And, and why did I know it? Because again, I was privileged to grow up in a neighborhood of really wealthy people that were investors and they were smart and like I had access to all of this. I was really fortunate. Most people were not as fortunate as me. So now I got to spend my entire Life on YouTube trying to spread that word to every person. That's not growing up in a neighborhood with multi million dollar houses. Right. That is growing up in a neighborhood where the culture is not telling you that every single day. Like, hey kid, you gotta invest.
Lewis Howes
It's more on spending versus investing.
Chris Sacca
Exactly.
Lewis Howes
And it's more on how do I look good or how do I get the next thing that's going to make me feel happy and be socially accepted with my peers instead of how can I hopefully live below my means for a while, use that money to invest, and then once I start making more of my investments, the profits there, then I can buy certain things if I want to or just keep reinvesting it.
Chris Sacca
One thing you just said was wrong. You don't need to live below your means to do it. That's the thing. Like, a lot of the things that I was referencing to like, make to find money in your life to start investing with. I don't care if it's five dollars, you can open up account right now with like five bucks. Lot of these things were not living below your means. It's just kind of doing things like clipping coupons is not living below your means. You know, like, like, it's just doing things a little bit differently to find money in your life that you didn't really care about. But now with the mindset change of accumulating these dollars that are actually going to eventually be worth hopefully a hundred dollars each, hey, you fall short and they're only worth 40 or 50. Does it even matter? Does it even matter? The bottom line is these very tiny dollars are going to become very big. And you don't have to do anything but literally just do it and throw it in an account.
Lewis Howes
Yeah.
Chris Sacca
And just let it compound.
Lewis Howes
Chris, I know a lot of your audience that you mentioned before we started is men, you know, that are kind of in your system, in your community, on YouTube and Twitter, who are listening to you. There's a lot of women that watch and listen to the school of greatness. And if there's man or woman in their 20s and 30s, let's say, who hasn't gotten into investing yet, who hasn't taken it seriously, what would be the strategy if someone had an extra 100 to $1,000 a month and they said, I'm going to start going all in in this strategy. And whether it's $100 a month, a thousand, eventually more, if they have more, what should they start doing today to set themselves up for their future success?
Chris Sacca
Yeah, I've been aggressively trying to bring women into the investment world for 20 years, and I'm almost at a point of giving up. I tried so hard. I told you, like when I wrote my book, I exclusively market through mommy bloggers. Right. Because my entire investing methodology is observational investing. And the ironic thing is that women are better positioned, way better positioned than men to excel at this strategy. Like, women are so women Are way deeper into these sectors. Fashion, makeup. Like, okay, like I was just telling you, the world has become digital and social. Right. The best investments come from change. The bigger the change, the bigger the opportunity. Right. How do you detect that change in the world? You detect that change through, you know, reading conversations. What are people thinking? What are they doing? What do they want? What are they buying? Where are they going? Where are they shopping? Where are they eating? Who talks about this stuff more than anyone else? Like, who expresses themselves? Who expresses their feelings about their interest and their. And what they want to own and what they want to do? Women way more than men. Who's listening? Women way more than men. Women actually have all of the insight. Women have all of the alpha. They have it. They are just not convinced that they can monetize it. Right. I've literally, like, almost like most of my biggest traits over the past 20 years have come from female and youth trends.
Lewis Howes
Really? Right?
Chris Sacca
Yes. Most. Why? Because those are the trades where there is the maximum amount of information asymmetry, where the mostly older, wider, wealthier men who control most of capital markets on Wall street, they are slow to pick up on that change. That's happening to like, I always tell the story about Jeffrey Star when he did a YouTube video of elf primer putty makeup. This is like, I don't know, 10 years ago, E L F was a drugstore brand, was the cheapest, junkiest brand of makeup. And he's like, this is just as good as the $60 version. And I went to Walgreens and I just stood there all day and watch moms and kids coming in. And they emptied the shelf of elf cosmetics because of this one product. And that video got like 11 million views on YouTube. And I called the Wall street analyst who covered cosmetics for one of the big three sell side, and I asked the person if they had seen the video. I was like, do you see the Jeffree Star video? And they're like, who's Jeffree Star? They don't even watch YouTube. They don't even. They don't even know who these people are. They are so out of touch. And that ended up being a monster. This. This is when elf was at seven bucks a share, right? It went up to like 160. I'm sure you now it's back down to like 50, 60, 70, whatever. Most of my biggest trades, I think probably females knew about that information long before any men.
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Oh, mints.
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Lewis Howes
Why aren't women in general taking action on the information they see socially, digitally and culturally when they see a trend happening? Why do you think there's a fear or hesitation behind not investing in that trend?
Chris Sacca
Well, I think just the field of finance, which is associated with the field of investing. Historically, there is a misconception that you need to be a finance head or a math head to do this stuff. Historically, the men in society have always been over that. So it's just a massive misconception and it's just. I thought we would have come out of it 20 years ago when I first started talking about this. But like, it takes a long time for people to break out of it. Like, look at what's happened in the workforce with women, right? Like that happened. Like we have now like massively changed. Like who is in these jobs. Like that's happened, but it hasn't happened yet in the investor class. The investor class is still at least the active investor class. People that are thinking and aggressively pursuing investment accounts is still majority of men, right, that are talking about this, thinking about it, connecting dots. And it's crazy to me, man. It's just, it's absolutely crazy to me because when I like most of my insights come from TikTok comments. So first, I don't know, eight years I've been spending three to four hours a night ingesting TikTok comments. That, that, that is most where I get most of my information from. Before TikTok it was Twitter and Instagram and Facebook, right? Going Facebook, going back to the late 2000s.
Lewis Howes
What's the best trade you made in the last four years on TikTok comments that has paid dividends for you?
Chris Sacca
I mean, almost all of my trades these days, I mean, honestly, like most of them come off of TikTok. Like one of them was like the big crocs trade. When crocs started coming back in a really big way, a massive. That was mostly based on TikTok comments. Wall street just thought that crocs was a fad that would come and quickly go away. They've always thought that about crocs. And during the pandemic, especially during the pandemic, there was a huge trend for crocs and it was because of two things. One, they did, they killed it with the nursing community and the healthcare community. But then also they were doing all these big celebrity cola collaborations, right? So they did these celebrity collaborations and all of a sudden it kind of like made crocs cool and it really made crocs cool with like the middle school crowd. And so I was like reading these comments and I was like, dude, like, this is crazy. Like crocs are on fire.
Lewis Howes
How much was it that the stock at that point?
Chris Sacca
I don't even, I don't remember exact numbers, but there were so many things that happened during the pandemic, honestly, because the pandemic was one of the biggest changes that we've ever experienced in like consumer behavior of our lifetime. Like all of a sudden the entire world just spent a year in Their house, right? So like, think about all the change that happened when we all just went home for a year. We started. We cared a lot more about cameras on our computers. Logitech, right? That makes all the cameras. Guess what we bought a lot more of Printers. Interesting. Weird, right? Because all of a sudden we're doing our schoolwork at home. Now we're having to print out something, all kinds of stuff. There were so many things. We started buying camping equipment. One of my biggest trades was Schwinn Bicycle, which was part of a small Canadian publicly traded company. There were lines around every bicycle shop. Remember that?
Lewis Howes
Interesting.
Chris Sacca
Yeah, Remember that? The line. We bought more bicycles during that six month period than like ever. We bought more campers, camper vans. People were going camping, remember? More ATVs, more boats. I was just. Basically all I was doing was I was on, just reading comments on the Internet, just seeing what people were buying, what they were talking about. Right? There was more change than what we've ever experienced in our lifetime. And like people were obviously buying pelotons, right? Shopping at home. Amazon killed it. Shopify killed it. I mean, looking back, it's all obvious stuff, but in the moment, Wall street was really slow, like really slow to pick up on that stuff. I can't even tell you how many phone calls I did with like, literally like, like people that sold ATVs or like Jet skis and, and they're like, we've never experienced anything like this. And I'm like, why is sea doo not going up? Like the company. It's a sea doo, right? Like, that was one of my big trades, really. Just see, like there were a hundred of them. So during the year of the pandemic, I don't know, maybe your audience doesn't know this, but during the year of the pandemic, I turned a four and a half million dollar brokerage account into 35 million. Holy peak. Yeah, so, yeah, just doing that, Just literally doing that. Not doing anything sophisticated. Just like, oh my gosh, people are all buying bicycles. That company, 7X, it went up 7.7X from where it was 7 or 8X. So this is not like trading derivatives or options. Like the actual company itself went up 700% in a very short period of time, as did Peloton, as did so many of these companies that had never experienced that type of growth.
Lewis Howes
When do you know when to sell? So when to get in, when to sell? And if. What if people are like, it just seems like a lot of time to be watching the market every day, making sure I'm getting the maximum out of my trades.
Chris Sacca
So I'll summarize for you what I do. But if you want to go in really deep, my book is very personal. It's very old. It's like 15 years old. Now, Jack Schwager wrote a book called Unknown Market Wizards, where he spent, I think, a decade researching the top retail traders in the world. And I was really fortunate to be one of the five equity traders that trade stocks. To be included in the book, he wrote a 35 page chapter on my methodology. And he really goes in deep to my process.
Lewis Howes
Okay.
Chris Sacca
But at a very high list. But it's called Unknown Market Wizards. And I don't make any money when he sells books. But, but it's. He, he spent two days interviewing me. It was nuts. And he has interviewed every hedge fund manager in the world pretty much for 40 years. And he's seen it all. But if basically what I do is I surface some big change that's happening in the world, it could be a change to consumer behavior, to culture, to technology, politics. It could be a change in the weather. Like, one of my big trades back in the day was a company called Beacon Roofing, because I would monitor every spring the number of people that were searching the word roof repair on Google. And I literally would go, I'd had 10 years of history, and every year it would spike roof repair, right? And one year, the hail storms hit populated areas at such a high degree that the word roof repair was triple anything I'd ever seen before. Well, it takes the insurance industry, I think, like a full month to print the report of insurance claims that Wall street uses to trade companies like Beacon Roofing that are, they're like the largest roofing supply company in the country. But I had access that information within 24, 48 hours of the big hail storms. And the reason why it's hard to assess hail damage is because you could have really big hail storms. But if they don't hit highly populated areas, they don't matter. Right. If they hit a highly populated area and destroy a bunch of roofs that does a bunch of roof damage, that increases sales for the company that makes most of the roofing materials in the United States. Beacon Roofing.
Lewis Howes
Wow.
Chris Sacca
And so, like, that's just one random example of a trade.
Lewis Howes
It sounds like legal insider trading by getting public information.
Chris Sacca
That's exactly what it is.
Lewis Howes
And saying, oh, this looks like it might happen in the next couple weeks or month. Let me get in now.
Chris Sacca
And there's never been easier time to do it. Because now I could just do it from my, from my iPhone on my recliner at 11pm at night, searching comments on TikTok or, you know, that's how I get my alpha. Now back in the day, I used to do what Peter lynch used to do in the 80s, which is like literally stroll the mall and look for what stores people were shopping at and talk to people and talk to people that worked at stores and try to assess what was hot, what was not. Like that was very time consuming. And I still do that a little bit. Like, yeah, yeah, but so first you have to surface the change in the world that's happening. And there's change happening every single day. The next, this next year there are going to be companies that will skyrocket based on their sales going up because of some change that happened. So you have to find the change before the guys on Wall street do. Ladies on Wall street, right. Once you find the change, you have to determine if that change is going to meaningfully impact or what change will meaningfully impact. So this is actually where AI comes in. Pretty cool, right?
Lewis Howes
You could also ask ChatGPT.
Chris Sacca
So I was gonna say like you can find some change that's happening in the world and you could go in, chat GPT and say, hey, this is happening. What publicly traded companies are likely to benefit from this?
Lewis Howes
That's it.
Chris Sacca
And it will actually tell you, I used to spend like four days figuring that information out of myself, myself. Now you could just ask ChatGPT.
Lewis Howes
There's really been, I guess, three different things historically that have allowed people to build a mass sums of wealth. Real estate is one. I guess investing in companies or the stock market is another. Then starting a business would be a third. Correct. But I think it's 80% of businesses fail within the first five years and the other 20% barely are holding on or struggling. It's really rare to succeed in business and it takes a lot of luck and timing, all these different things. But a lot of people, you hear horror stories in the stock market as well as in real estate. For people, they went out and bought their first home and they lost all their money or it took so much time and energy, it just exhausted them that they gave up. They got excited in the stock market, but they got in at the wrong time. Two year downswing, they got scared, they lost most of their money. Business maybe they try to start a business, it failed and they just feel like, God, at every angle I go to try to earn money, I struggle, I spend so much time and I get defeated. What wisdom can you share to someone today on whichever route they want to take on how to emotionally and mentally overcome the obstacles that may come their way?
Chris Sacca
Does it ever feel like you're a marketing professional just speaking into the void? Well, with LinkedIn ads you can know you're reaching the right decision makers. You can even target buyers by job title, industry company seniority skills.
Glenda Baker
Wait, did I say job title yet?
Chris Sacca
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Glenda Baker
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Bill Perkins
Don'T ever put yourself in a position to have to sell. If you never put yourself in a position to have to sell, you're never losing money on real estate. I haven't sold a house in the last 30 years that hasn't sold for more if the person was able to wait and sell it when they wanted to. When you put yourself in a position you over leverage you buy in an area that is transitioning or that is high crime, that is a gamble. Those people, you're going to lose money. But when you put yourself in a position to never ever have to sell, you're always going to make money in real estate. Now I don't know about you, but those people who bought Blockbuster, it doesn't matter how long they wait, they're never getting that money back, are they? And that's the difference between real estate and stock. People say, oh well, you know Glenda, if I had If I put $130,000 in this stock, it would be worth a zillion dollars, correct? But if you put down $6,500 on $130,000 house, you only have $6,500 in it. If you lost it, you only lost $6,500. You didn't lose $135,000. That Blockbuster stock you lost all 135,000. People don't think about it from that perspective. You Talk about appreciation. You bought $150,000 house in 1975. That house is now worth a million dollars. Guess what? You also had a place to live. Okay. Or you had an income generating, generating assets. So that's the thing, is, like the last time I checked, those stocks aren't doing that for you. And all I know is real estate. Like, I. I'm old. I want to see, touch, feel my money. When I want to be able to get my money out, I want to be able to get my money out. I don't want to be at the mercy of the stock market. So while I have stock market investments, that is not where I keep my money. I keep my money in houses where I can see touch and feel it. And the worst case scenario is that you have it rented out and it's renting for less than your payment. Okay? So this is the worst case scenario. Your payment is $2,000 a month, and you're only getting $1,500. That's a $500 savings deposit that you're making per year into that account. And if you keep that house and you sell when the market is high, you're going to make all of the money that you put back in it.
Lewis Howes
Right? Right. What about if someone says, well, what if, you know, I've got to fix all these things and there's all these extra costs and expenses that I have in the house over a few years, and it just. Maybe I chose it wrong, or maybe the realtor. I didn't see these things. The inspector missed something, whatever it is, and I got to pay $20,000 for a new AC, the roof, the. This, the bathroom. And it's like I'm in tens of thousands of dollars more. $100,000 more than I have or want it to be. And now I've got to hold onto this for 20 years to make a profit. You know, how does someone wrap their mind around that and not feeling like they're losing money? They don't have access to that cash, and they have energy invested into a house versus kind of just that money in the bank or in an index fund.
Bill Perkins
Right, exactly. So what happens is it's critical to understand what you're buying. It's critical to do your homework on what you're buying. Not just having a great real estate agent, not just having a great inspector, but getting in the weeds with it. And what I mean by that is driving through the neighborhood, getting lost in the neighborhood. Did you do your own recon in the neighborhood? And that's What I want people to do is don't depend on somebody else to tell you everything. I want you to understand how to do it. And so a lot of times when I'm with buyers, I'll put them in the car and we'll just drive around, get lost, turn off the gps, eat in the restaurants, shop in the grocery stores because, and this is such a simple thing that a lot of people don't think about. If the grocery store has great produce, that means that people are spending money in that grocery store. That means that people are concerned about what they're eating. They're probably going to take care of their house. Nobody ever talks about stuff like that. You probably never thought that if I have good grapes at my grocery store, it probably means that I'm living in a neighborhood that's well kept. If you're concerned about the food that you're eating, what you're putting in your body, probably concerned about how you're taking care of your house, what would you.
Lewis Howes
Say are five things people should look for when finding a great deal or an investment in real estate?
Bill Perkins
The best investment in real estate. Grandma's house. Okay. Something that needs cosmetics, not infrastructure. Infrastructure may not sound sexy, but infrastructure is a wonderful thing to have. Number two, look for an area that is not at the top, but that is growing, that you can kind of see, like, oh, wait a minute, they're doing work here. There's a dumpster in the driveway here. And do that kind of research. Understand, like what direction is the neighborhood going in? Number three, I would probably say when you're looking to invest, make sure that you understand what you're buying. A lot of people don't understand, like, is this house on a two lane street? Is that a problem? Does this back up to the retention pond? Are there mosquitoes? It's Atlanta, Georgia, it's hot as hell, there's all kinds of mosquitoes. Do you understand how much less you're going to take for a house that's on a retention pond? So that's why I always want people to understand exactly what it is that they're buying. I hammer on that a lot. And again, I don't want you to get caught up in your ego. A lot of people buy for vanity.
Lewis Howes
Really? Oh, what do they, what's the ego mean when they invest in ego?
Bill Perkins
Because they want, they want you to drive up, pull in the driveway and.
Lewis Howes
Say, what a nice home.
Bill Perkins
Oh my stars, look at your fancy house. You don't want that literally unless you're living in it. Maybe not. You don't even want to win. You're living in it. Literally. You want to live in the house that works the best for you and your family. Like, do you want to like out here in la, it's a little bit different, but in regular markets, like think about it and I'll talk about Trae Young. I love basketball. Trae young bought a $20 million house out here in LA, signed a contract for $215 million. Praise the Lord and pass the money. Right. Do you know how much the taxes on that house are? $600,000 a year. Okay. Do you know how many houses, investment properties you could buy with $20 million?
Lewis Howes
Wow.
Bill Perkins
So you could have bought a fancy 5 million dollar house in Atlanta, Georgia, which would have been the same as a 20 million dollar house out here, for God's sake. Then you could have bought some investment properties and built generational wealth. Not that his $215 million isn't going to be generational. But ask Evander Holyfield how that works out. That's the thing you look at, look at Evander Holyfield, a fighter who sacrificed his body, his well being, his quality of life, made hundreds of millions of dollars in his career and loses his house to foreclosure. And think about that. So that's when I, when I talk about vanity. Anytime that you're trying to impress somebody else with what you have, I just going to ask you, just, let's just rethink that, just, just for a second.
Lewis Howes
Wow. What about when did you really learn about how to manifest in your life? Was there a time or a season or a decade where you started to think a certain way when it came to either attracting the right clientele as a realtor in terms of attracting the right homes that you wanted to buy and invest in, in terms of business deals that you wanted to do. Was there a season or time that you learned about manifestation?
Bill Perkins
Making mistakes was probably the biggest teacher for me really. Not just making mistakes in my real estate business, but making mistakes in my personal life cost me so much time, really and so much money because, and I think the reason that I'm passionate about it is because like I went out and bought the Mercedes. I made $137,000 on one house. I went out and bought a Mercedes, I went on a shopping spree and within 12 months I was selling my Rolex at a pawn shop.
Lewis Howes
Really?
Bill Perkins
Yes, really. I was selling my car, my Mercedes, I was selling that Mercedes and buy. No, no, no, I didn't sell it first. I didn't sell it at first. At first. Sit down. It was paid off because, you know, I made all that money. What you really don't realize, I went.
Lewis Howes
Down in half after a few months.
Bill Perkins
Well, what you don't realize is that you got to pay taxes on all that money. But anyway, so I buy the car and I realize I have a cash flow issue. So what do I do? I go get a tote. The note at 27%. So you want to talk about. Oh, Glenda, what would you do when I talk to you? I'm just telling you straight from the horse's mouth. I made this mistake. Don't make the same mistake I did. I went out and bought the fancy Rolex. That's why I have the $130 ring from Ross Simons. I mean, it looks fancy, looks nice. It works and matches my outfit today. So that's what I want people to focus on, is like. Is like the mistakes that I made. Don't. Don't do what I did.
Chris Sacca
Learn.
Bill Perkins
Learn from me. And so that, I mean, how do you manifest it? When I sit, when I never will forget? I saw this agent who sucked as a real estate agent, and that guy was making more money than he could count.
Lewis Howes
Really? What was the secret?
Bill Perkins
He was a good talker, but he was investing in pos. Houses. He was investing in these little houses, and he was fixing them up and selling them and fixing them up and renting them. And I remember thinking to myself, somebody that is not as good as I am at real estate is doing a thousand times better than me. And every time I thought about going out and pissing the money away, I thought about that guy and it pissed me off. It made me so mad, it just made me crazy. And every time that I think about doing something that's probably, you know, impulsive or ego driven, and I think that a lot of times you get caught up in being ego driven because it feels good when everybody looks at you and they think that you're successful. But for me, every single day, I focus on what moves me from here to there. And here is freedom for me.
Glenda Baker
Race the rudders. Raise the sails. Race the sails.
Chris Sacca
Captain, an unidentified ship is approaching. Over.
Glenda Baker
Roger, wait. Is that an enterprise sales solution?
Chris Sacca
Reach sales professionals, not professional sailors.
Lewis Howes
With LinkedIn ads, you can target the.
Chris Sacca
Right people by industry, job title, and more. We'll even give you a $100 credit.
Glenda Baker
On your next campaign.
Chris Sacca
Get started today at LinkedIn.com results, terms and conditions apply.
Glenda Baker
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Bill Perkins
Freedom with my children, freedom with my family, Freedom with my little grandchildren. My one and only goal is to be able to do whatever I want to do whenever I want to do it and not have to worry about going up another set of steps, not worrying about what next house I have to sell. And what turns me on is helping people, inspiring them. And so I just say to myself, every single day, my name is Glenda Baker. Only amazing things happen to me. My name is Glenda Baker. I am a woman of action and my name is Glenda Baker. And everybody's going to know my name. And all I want to do is just help people build generational wealth through real estate.
Lewis Howes
Wow, that's beautiful.
Bill Perkins
And inspire them through my mistakes.
Lewis Howes
Sure.
Bill Perkins
Because we don't all need to make the same mistake. Let me have been the guinea pig.
Lewis Howes
What would you say the three most painful mistakes in business that you've made over the last 30 plus years that really taught you an important lesson? Maybe you had to learn it.
Bill Perkins
Yeah.
Lewis Howes
Over and over again.
Bill Perkins
I didn't pay my taxes. That was probably, that was, that was probably the most eye opening, really thing because I, I mean, I grew up with a single mother. Like, I didn't have anybody explained. Like, I didn't even know you, that when you only got paid when you sold a house. I'm in real estate school and the teacher says now when you sell a house, you make this much money and I'm like, like, you don't get paid on Friday.
Lewis Howes
Like, you have to sell to make money.
Bill Perkins
Like, I mean, I didn't know, I didn't know that. And I even tried to get a job as an assistant. Nobody would even hire me because, I mean, I'm barely out of high school, didn't go to college. And so, you know, I didn't understand about paying taxes. I mean, I made $137,000 on that one house, for God's sakes. Like, how much could the taxes be? Right?
Lewis Howes
A lot.
Bill Perkins
A lot. Had no clue. So the biggest financial mistakes in business I have made have been I didn't pay my taxes. I made purchases based on Ego. And I let people that didn't matter influence me to make purchases that I shouldn't have.
Lewis Howes
Really?
Bill Perkins
Yeah.
Glenda Baker
Because you mean people you knew or.
Lewis Howes
People you didn't know?
Bill Perkins
I think it was a little bit of both. People that I knew, and I thought, oh, well, you know, they're doing well and they're putting all of their money in this. Maybe I should do that. Or. I believed all of the. I believed all of the hype, and I think that that was a huge mistake.
Chris Sacca
Just.
Bill Perkins
Just believing all of the hype that wasn't really the truth.
Lewis Howes
Yeah.
Bill Perkins
Not being able to discern well enough.
Lewis Howes
Yeah.
Bill Perkins
But being distracted. Probably one of the biggest money sucks of my life, really. Being distracted.
Lewis Howes
What type of distractions over the last 30 years?
Bill Perkins
All kinds of. All kinds of distractions. But mostly for me, I've been distracted by the shiny penny. I've been distracted by feeling like that I needed to be married to somebody, to be somebody for many. I mean, I can remember it so, like, vividly in my head that I wasn't going to be worth anything unless I was married to somebody really. Some big person, like, you know, like Ted Turner. Like, you know, I'm thinking, like, oh, I should be married to some, like, big shot person. I wouldn't be worth anything without that.
Lewis Howes
Where did that come from?
Bill Perkins
I don't. I don't. You know, I don't know. I think about, like, I think about in my head, I was the only child in my school whose parents were divorced.
Lewis Howes
Really.
Bill Perkins
And I remember, like, seeing Mr. And Mrs. Meyers and Mr. And Mrs. Bourgeois. And I remember seeing them and thinking, you know, they had the two kids, the three kids, the dog, the house with the swimming pool. Like, the mama stayed at home and the daddy took care of everything. And I remember thinking to myself that I was so cheated you didn't have that. That I didn't have that life. And here was my mother. First off, she was old because she was 44 when I was born. So my mom was the oldest mom. She was the only divorced mom, single mom. My dad wasn't really in my life, and so here I am. And then on top of that, I have to have this back surgery, and I'm in a body cast for a year in seventh grade. And just everything, it just. And I've got this big accent, which I don't think I have, but lots of people think I do. But it just. I mean, there was just so many things. And I kept thinking that I was like the odd man out. I was like, I Was different than everybody else. And rather than appreciating that difference, I worked so hard to be like everybody else.
Lewis Howes
People pleasing, trying to fit in, doing whatever. Others.
Bill Perkins
Oh, yeah. Trying to fit in. I mean, I, you know, here was the last kid picked on the playground, and I wanted to fit in so bad. Yeah. And I couldn't ever figure out how to get those pieces of the puzzle together. Back when I was in school. I mean, I graduated from high school in 1984. You didn't call it bullying. Like today you would say, oh, she was bullied as a child. She didn't call it that then we.
Lewis Howes
Didn'T call it then.
Bill Perkins
You didn't call it anything. Tough enough. Yeah, suck it up, buttercup. You know, And I think that for.
Chris Sacca
Me.
Bill Perkins
A lot of the distractions were just trying to be like everybody else, get somebody's attention and prove that I was worthy.
Lewis Howes
I know that feeling. And you felt like you only had worth based on who you were with. It sounded like. Or who you were friends with or who you were dating or who you were married to.
Bill Perkins
Who I was associated with, who I was attached to. Attached to was what defined my worth.
Lewis Howes
Wow.
Bill Perkins
And I think that that was huge. Once I realized that my value was determined by me, was a turning point in my life.
Lewis Howes
When did you learn that?
Bill Perkins
2017.
Lewis Howes
Really?
Bill Perkins
Yeah. Not that long ago.
Lewis Howes
What made you think that and what made you realize and actually start to believe that?
Bill Perkins
I stopped. I struggled with drinking, and I stopped drinking at the end of 2015. And I think that that really started giving me a lot of clarity. I think that alcohol had been. Had disguised a lot of issues that I had. But I think that when I stopped drinking and I was focused on being my best self, that helped. And then I went to a Tony Robbins event, and he talked about just being present and these moments. Just being present and building these moments. And I went with my son. My son was really struggling at that time.
Lewis Howes
How old was he then?
Bill Perkins
He was 16 years old.
Lewis Howes
Wow.
Bill Perkins
And he was really kind of going through a difficult season of his own life. And I took him to the UPW for him.
Lewis Howes
Yeah, right. You got more out of it than he did, probably.
Bill Perkins
And we're there four days, and at the end, and my son's tall, and he puts his arms around me, and my ear is right at his heart, and I can hear his heartbeat. And he leans down and he says, I'm never going to forget these four days with you.
Lewis Howes
Wow.
Bill Perkins
And I remembered in that very second, in that moment, like, here was this Child watching me like you. He deserves it. He deserves your value. He deserves you to be worthy. Wow. And so I said, I left that moment and I said, my life, Skull, is to string together moments of a lifetime just like that one that I could just feel. And everything I do, every single thing I do is built around how I can build a moment in time for my life, my children, and the things that the people that I love.
Lewis Howes
That's beautiful, Glenda. So if someone's in their mid 20s, early 30s, right, they're in this kind of 10 year range, how can they start thinking about this? Maybe they've just said, you know what? I'm just hustling. I'm going after money right now or a career just to make money, that I'm spending it all. I don't really have much in savings yet, but I know I should be investing. But how can they start to think about the formula for their life in terms of maximum enjoyment or fulfillment, these memory dividends, which makes a lot of sense to me without being broke the entire time, right?
Glenda Baker
So for each person in each profession, right? Like there are certain situations where people have pensions, guaranteed jobs, et cetera, and career progression, right. Where their salary is going to be going up and they're also going to have their own health, right? Like, like they're very healthy, not that healthy, et cetera. And what they're trying to do is thinking about, okay, what experiences in the 20 to 25 bucket, or 25 to 35 or whatever, any way you want to break it up, what experiences belong now, okay, that I should be doing now and gifting the memory dividends to my future self.
Lewis Howes
Interesting.
Glenda Baker
Or what things am I doing now that are robbing my future self from stability, you know, and causing worry, right? And so there was a period in my life when I was in my 20s, I was seesawing, right? I was like saving too much. I was borrowing from my poor self to give to my future richer self, which did not make any sense, Right?
Lewis Howes
Right.
Glenda Baker
And then I went from the I'm going to party and going crazy and I'm spending every single nickel I made, right? To creating future instability for myself by not saving. And now. So for each person, their career path, their earnings potential, etcetera, that will be different. But the, the thing is to get off autopilot and be thinking about it, right?
Lewis Howes
And maybe you're fumbling your way through it for a year or two, you're like, okay, I'm not sure what it's going to be, but I'M paying attention to what I want right now in the future.
Glenda Baker
Right. Like, so, you know, people will have other experts, like a financial planner. You know, a lot of times the financial planners are about, let's maximize the money. It'd be like, that's not the ultimate goal. The goal is to maximize fulfillment, and so they will keep you safe and maybe you'll save a certain amount of money. But you're the driver. You are responsible for your own life. And so if you want to be intentional and get the most out of your entire life and each time period you have to think about, okay, is backpacking now through Europe, is this the period to be backpacking through now, or is it 20, 30 years from now? Is this a, A trip or an experience or, or, you know, or charitable thing that I need to be doing now, or is this something that I need to be doing later in my life? Right. Just that thought process by ordering your life properly will help you have a more fulfilling life.
Lewis Howes
Yes. What do you think is the biggest psychological crime someone can make when it comes to their money?
Glenda Baker
I think the biggest psychological crime is people fear running out of money instead of fear of wasting their life. And so, you know, they have this fear of embarrassment of like, I'm going to run out of money and I'm going to be broke or I'm going to do X, Y and Z. Instead of feeling like I am wasting my life. I have for the. We were talking about the 20 to 30 bucket. I'll just, you know, this is it. This is the only period I'll be 20 to 30. There are certain activities, experiences that are meant for this bucket. Right. People marketing services and products to you, you know that they're there.
Chris Sacca
Right.
Glenda Baker
Like, I don't want to do them, like, go have fun. Right. But, but. And you only get one shot, one go around, you know, and so, and they're worried about, you know, in the 30, 40. So I think people worry about embarrassment, what other people think, judgment about their lifestyle or them failing in the future, et cetera, as opposed to worrying about, like, I don't want to waste this ride. And it's not even the ride for the whole life, every single period of your life. So if you're a parent with small children, not wasting that period with teenagers, I know a lot of us would like to waste that period and just be like, get rid of spirit. But that period. And then, you know, eventually you don't have kids in the house anymore, and that's a different period in your life. And there's different activities and different opportunities that go. And I often say, life is like Tetris, right? Like, if you were in heaven, let's assume this heaven, and you're about to come down to earth as a human being. And God's like, here's the bucket of experiences. And when I use experience, I mean choices, right. I mean it in the broadest sense. Hedonistic, charitable, whatever.
Lewis Howes
Yeah.
Glenda Baker
And you're like, oh, the infinite bucket of experiences. I want to go hiking, I want to tennis a thousand times. I want to have sex a jillion times. I want to do all these things. You're throwing them into the experience bucket. I want to start a business, I want to go to school, blah, blah, blah. And it's full. And God goes, great, you can have all those. You just have to get the order right. So life is like Tetris, you know, you remember the game Tetris. So you had to get the shapes, right? Life is that way. Like, if you don't have the experiences at the right time, they run to interfere with each other, or your ability to do them disappears. So you can have all the money in the world. Right. When I was in St. Petersburg, Russia, this is before the war, beautiful city. And one of the things about Europe is, like, things they allow you to do would be completely illegal in the United States. It's not like safety laws or whatever. So you can climb these steps, walk around the churches, and then walk around the balcony. It's beautiful. It's amazing. It's like, wow, I can't believe we still get to do this. And it was like 115 steps. I remember it was an odd number. I think it might have been 111, but. And there were like six or eight tour buses of senior citizens, you know, coming to go see the museum and this church, not a single one climbed those steps. Not a single one. So their trip to St. Petersburg was entirely different than my St. Petersburg trip. Their experience, the information they got to process, the things they got to see was totally different. I'm not saying it wasn't enjoyable, but perhaps in a city that allows you to roam around and do these things and go on cliffs and overlook type of things, and you enjoy it. Perhaps that trip should have been taken much earlier.
Lewis Howes
Wow.
Glenda Baker
And so, you know, that's an example of getting the order right.
Lewis Howes
Yes, getting the order right and making sure you're using your money at the time where you're able to use it the most effectively, right?
Glenda Baker
Yes. It's getting the most out of that. Tool. It's getting the most out of that tool.
Lewis Howes
Right. The tool of money.
Glenda Baker
Your ability to convert your money into meaningful, fulfilling experiences decays over time. So you know, your brain reaches mental maturity around 28. Your body is physical maturity around 33. So if by and large, if you were in the best shape of your life at 33, that is the top, then you're going to plateau and decline. I will never ever, unless, you know, new technology, gene therapy or whatever, but be in better shape than I could have been at 33. Right. It's over.
Lewis Howes
It doesn't mean you can't be in still great shape.
Glenda Baker
No, no, you're still in great shape. But I'm just saying my ability to do certain, like, listen, I can get.
Lewis Howes
I was not playing college football anymore.
Glenda Baker
No, no, no. Last year I was like one in like great shape. I, I got down to like a 9% body fat. My cardio VO2 was over. But my, my lazy 28 year old self will smoke myself in a ring. Really like smoke myself. Right.
Lewis Howes
Like you just doesn't need to warm up.
Glenda Baker
Does not stretching anything. Right. Like and, and so, and then on top of that, if I raise them, I'm sore afterwards. Like my knees hurt.
Lewis Howes
You need to recover for a week.
Chris Sacca
Yeah.
Glenda Baker
Cartilage in the back is kind of, you know, all those things.
Lewis Howes
He's just hopping around, you know, no sleep, able to do whatever.
Glenda Baker
Yeah, he's just that guy so lucky. He just doesn't know how good he has it, you know. And so, you know, I think about these things and you know, sometimes there's very small things. Like I was, I was at a place where my friends were going to go wakeboarding at my 50 50th birthday. I was, you know, I'm generally a lazy guy. I'm laying on the beach, I'm like, I don't want to go. You guys go, whatever. And then I thought about it, I said, when am I ever going to have a chance to go wakeboarding in the future? We're here, we're in the Caribbean. There's a wakeboard boat there. When's the next time there's going to be a wakeboard boat? Maybe, maybe two years from now, three years from now. And I thought about my back. You know, once your cartilage starts going, it just keeps going. I thought this may be the last time I'm able to go wakeboarding and enjoy it and I'm going to switch to another physical activity. So I got my lazy butt off the beach and said, I'M coming. I did a jump, I landed a jump. I was happy, you know, it surfed. And that was the last time I will ever go wakeboarding because of the speed of wakeboarding. And it's. So now I wake surf, which is a lot slower speed, and I can do it later on in my life, but my wakeboarding days are gone forever.
Lewis Howes
Wow.
Glenda Baker
And had I not done it at that time, it would have been years and years before, But I'm wakeboarding. And so I got all the enjoyment, all the memory devons of that trip, hanging out with my friends, et cetera, but that's it. The wakeboarder bill is dead.
Lewis Howes
But now you have that memory dividend that you can tell this story to me and you can think about that story for the rest of your life.
Glenda Baker
Yes. And I can also use it as a teaching tool. Right. So for people who are still, you know, got all their cartilage. All their cartilage.
Lewis Howes
No broken bones.
Glenda Baker
No broken bones or anything like that. Like, hey, you know, the time is coming where whatever activity is, it will be the last time for you.
Lewis Howes
Yes.
Glenda Baker
And you'll be moving on to other activities. Right. So I'm a wake surfer. You know, maybe you're just a boater eventually. Yeah, exactly.
Lewis Howes
Your book has really taken off in the last few years since it come out. Since it came out. It's called die with zero, getting all you can from your money and your life. And I want people to get a few copies of this because I think there's been this misconception of, like, make as much money as you can and save it for as long as you can so that you can enjoy the rest of your life when you retire at 64 or 72 or whatever the retirement age is. Right. This kind of concept. Save, save, save, invest, which I'm a big fan of, saving and investing.
Chris Sacca
Yes.
Lewis Howes
So that it will pay me dividends now and in the future, and so I won't stress or have worry about money. But I think people take it to extreme sometimes. Correct. And they don't enjoy their time and they get the bucket list and the time bucketing backwards.
Glenda Baker
Correct.
Lewis Howes
And so why should we be thinking about die with zero? And the idea of having nothing when you die for some people seems selfish. What about leaving money for my kids or for charities or, you know, am I going to leave my family with nothing? What does that say about me and my legacy? So what is your thoughts around, you know, these 17 questions I just asked around, you know, how we should be thinking about money? For retirement, how we should be thinking about money, for leaving it behind, how we should be thinking about legacy. And how does having money in the bank when you die connect to legacy? What's your thoughts on that?
Glenda Baker
So I'm gonna go first, which is on everybody's mind. And one of the number one questions I get is like, what about the kids? And there's a chapter called what about the kids? And it's about charity and kids. And so the same laws of physics that govern your body govern your kid's body. Okay? So they're gonna grow. Their brains are gonna eventually mature. Trust me, parents, their brains will eventually mature.
Lewis Howes
How many kids do you have?
Glenda Baker
I have two. I have two. 16 and 19. And their bodies will reach physical maturity, and then they will plateau and start to decline. So if your body is unable to convert the money into meaningful experiences as you age. Right. Like your physical ability to either enjoy them or do them goes down. The same is true for your kids. So actually giving a smaller amount to your kids at an earlier age will be more impactful and more fulfilling than waiting to you kick the bucket. And they're 66 or 65 or 60. Right. And two thirds or more of their life has gone by.
Chris Sacca
Right.
Glenda Baker
So what I advocate for is that be intentional. You want to give your life, your kids fulfillment, a fulfilling life and choices. So whatever you're going to give them, you know, some people, like, I'm not giving my kids anything. They got to make it. I had to make it. They had to make it. But whatever you're going to give them, give it to them at the right time. Timing is important. And so I advocate, you know, somewhere between 25 and 33, right. Different. Some kids are very mentally mature, and they can handle money when they're younger. And, and. And you know, it's going to be fine. And some are a little bit later in life.
Chris Sacca
Right.
Glenda Baker
But at a certain point, it's their life. Right. You've done your best to prepare them to navigate the world. They're their own person. If they want to light it on fire, let them light them on fire. If they want to do this, you know, and they're industrious, et cetera, let them do that. But it's their adventure. And so. And that money has the most impact when you give it to them then. And also your legacy, you know, people like, I'm working hard for my kids. You know, they're 60. I'm working hard for your kids. Like, like, well, part of the legacy and the fulfillment from your Kids is spending time with you, moments from you, not you going to work, you with them, memories with them. So in some situations, in a perverse way, you going to work to make more money to give your kids when you die is actually taking away from the fulfillment.
Chris Sacca
Wow.
Glenda Baker
And diminishing your legacy.
Lewis Howes
Interesting, right?
Glenda Baker
So we have to be really intentional and think about what are we trying to do when our kids with kids giving our kids money and you know, six year olds are not kids. You know what I mean? So I, I think one of the most asinine things we do or the most autopilot not living with intention things we do is wait till we die to transfer assets to our kids.
Lewis Howes
Interesting, right?
Glenda Baker
And that's the same thing with charity. Like charity is now, right? People are hurting now, dying, starving, whatever the issue is that speaks to you, it is now, right? So, you know, I give kind of examples as like, imagine the people that donated to, you know, funds for polio said I'm just gonna wait till I die. And then more kids have polio, right? You know, there's people, you know, and I just use that as an example. And even if it's into education, the returns on education or a human being educated right now far exceeds any market return that you can make. So if you are a charitable person and you identify capital that you're not going to use before you die now, right?
Lewis Howes
So how do you think about this in your own life then? With terms of, you know, you have two teenage kids, how do you make sure that you raise kids to not rely on you for money? And you're not getting, giving them too much personally, but you also want to maximize for fulfillment and memories. And you, you know, you have a.
Glenda Baker
So you're going on a sub question is like, do you give your kids money or not?
Chris Sacca
Right?
Glenda Baker
And that there's books on this, like give them, there's books like don't give them anything. And his books, like give them everything.
Lewis Howes
How do you navigate that? Because it's all, you know, you've got so an amazing lifestyle. You've got properties, you've got boats, you got planes, you got, you know, do you put them in the back of the plane coach and you're in first.
Glenda Baker
They take a Greyhound across.
Lewis Howes
Like, how do you do it? Whether psychologically set up for success, but also rich in memories and experiences with you.
Glenda Baker
So by me, quote unquote, making it right, I've made my life easier and therefore their lives are easier and they're in a bubble, right? And as much as I try and, you know, the exposure, I try and get them outside the bubble.
Chris Sacca
Yes.
Glenda Baker
But the main thing I wanted to do is raise strong, independent women who are kind, who can navigate the world. It's the best I can hope for. Right. And as far, you know, the way I look at it is, is that I have an amount that I want to give them.
Chris Sacca
Right.
Glenda Baker
That is for them to do as they please when they're mature enough to get it. So it's not my money, it's in a trust, it's separate. Because if Bill Perkins goes out gambling in some poker game, they're not going to get my. It's not my money. You know what I mean? It's their money. So I don't have to worry about the risk to me, et cetera. They're taking care of, but they don't get to use it. It's not like a 16 year old running around in a Ferrari or something like that. It turns over to them, to their control when they're between 28 and 33. I think mine is between 28 and 30.
Lewis Howes
Yeah. And does it unlock every month a certain amount or is it a lump sum?
Glenda Baker
There's, there's, you know, there's all we're getting into state and, and trust planning, but you know, there's a board that has, for health support, maintenance. They can. And trust, not me. Other people can be like, okay, you're going to grad school, we'll give you a little bit of education, whatever. But all of it unlocks to them at 30.
Lewis Howes
Got it. Okay.
Glenda Baker
Because I've lived my life. So I say to my friends, like me, I live my life, it's their life. Now, if I'm gonna give it to them, if it's a real gift, it's theirs.
Lewis Howes
Right.
Glenda Baker
When they're able to handle it, I'll give it to them. And they're like, well, what if they can't handle it? It's too late. It's not like at 40 it's gonna help them anymore. And their health is declining. Right. So I'm just like, let them have the adventure they want to have with the resources that I'm willing to give them. So I don't tell people, hey, you have to give your kids money or not. I just tell them the when. The when. The when. The when is very, very important.
Lewis Howes
Yeah. And it's your responsibility, I guess, as a parent, to educate, teach, train them to be kind, you know, thoughtful human beings.
Glenda Baker
Exactly.
Lewis Howes
And hopefully they're able to make those decisions by Then. And that's in some way your responsibility as well to oversee that up until 30 or whatever that time is.
Glenda Baker
Well, I mean, it's. It's. At a certain point, your job is done.
Lewis Howes
Right.
Glenda Baker
And the race. They're their own person. They're adults. Right.
Lewis Howes
They're not gonna listen to you anymore.
Glenda Baker
They're not gonna listen anymore anyway.
Chris Sacca
Right.
Glenda Baker
Like, you're on the advisory committee. Yeah, I'm already. I think I'm already on the advisory committee.
Lewis Howes
They call you when they need money.
Glenda Baker
Exactly. On the advisory committee. And. And you hopefully have done a good job, but your job, that part of trying to control your kids is done. You mold through advice from that point on. And so a gift is a gift, and my gift is set and it's done. If I want to.
Lewis Howes
If I.
Glenda Baker
If I come into a windfall and hit the lottery and I feel like, hey, I want to give more to them, I can add to it, but I'm living intentionally. Like, hey, this is when my. They're going to reach peak mental maturity, mental acuity and physical maturity. This is where they're going to hit plateau, et cetera. This is when it's going to have the most impact on their life. Life. Right, Right. It's going to have less impact on their life because they can't even convert it into the experiences they were later on their life. Right. And so it's their adventure. Right. Their adventure to have. I don't want to control people from the grave.
Lewis Howes
Yes.
Glenda Baker
The rules I set forth, you must do this. I'm just like, what kind of human being does that? Like, tries to control another human being with money. Right. I. I want them like, you've done your training, have the adventure you want to have.
Chris Sacca
Right.
Glenda Baker
And so that's how I think about that now. The having the zero part is, you know, one of the 17 questions.
Lewis Howes
Yes.
Chris Sacca
Is.
Glenda Baker
Is if I spend, I have only. The only thing I have is my life energy, and that's the time I have on planet.
Chris Sacca
Right.
Glenda Baker
On this planet, the. The minutes, et cetera. So if I spend that time going to work, let's say I'm just digging holes. I'm digging holes.
Chris Sacca
And they.
Glenda Baker
They gave me this. This thing called money. Could be Chuck E. Cheese, token, could be anything. They give you this thing called money, and then I just hold it and then I die with it. I've essentially wasted my time digging ditches. Right. I've worked for no reward. Right. We can see on his face that that's asinine. Right? Like, no, you don't want to go do something that you normally wouldn't do with all the other activities you can do on this planet, right? Almost infinite choices, right? We don't want to go do that for no reward, right? So we're going to work for something, right? And a lot of us are going to work, you know, some of it, we enjoy it. We enjoy what we're doing, we enjoy teaching people. But that reward, when we slice up the reward part, that is for us to use as a tool in our tool bucket to maximize our fulfillment. Fulfillment. Nobody goes into the hardware store, let me get some hammers and saws, and then throws them away, right? Well, I guess there are some people who buy hammers and saws, put them in the garage and never use them, right? But, but that's the, that's the, that's what happens with a lot of people is they just save, save, save, save. Never use a dime, right? And so I'm trying to stop them from doing that and say, hey, let's think about how we can spend and use all your assets, your wealth, your health and your time, or focusing on your wealth before you die to get maximum fulfillment and the maximum ride.
Lewis Howes
Yes.
Glenda Baker
Right. And so one of the axioms is spend all your money down to zero as close as you can before you die, Right? So you do not waste your life working for no reward.
Lewis Howes
I hope you enjoyed today's episode and it inspired you on your journey towards greatness. Make sure to check out the show notes in the description for a full rundown of today's episode episode with all the important links and if you want weekly exclusive bonus episodes with me personally as well as ad free listening, then make sure to subscribe to our Greatness plus channel exclusively on Apple Podcasts. Share this with a friend on social media and leave us a review on Apple Podcasts as well. Let me know what you enjoyed about this episode in that review. I really love hearing feedback from you and it helps us figure out how we can support and serve you moving forward. And I want to remind you of no one has told you lately that you are loved, you are worthy, and you matter. And now it's time to go out there and do something great. Hey everybody, Ted Danson here to tell you about my podcast with my longtime friend and sometimes co host Woody Harrelson. It's called where everybody knows your name and we're back for another season. I'm so excited to be joined this season by friends like John Mulaney, David Spade, Sarah Silverman, Ed Helms, and many more. You don't want to miss it. Listen to where everybody knows your name with me, Ted Danson and Woody Harrelson. Sometimes, wherever you get your podcasts at.
Glenda Baker
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Podcast Summary: The School of Greatness – Episode: From Broke to Millions: 3 Experts Reveal Their Investing Secrets
Host: Lewis Howes
Guests:
Release Date: June 20, 2025
In this compelling episode of The School of Greatness, host Lewis Howes engages with three seasoned experts—Chris Sacca, Glenda Baker, and Bill Perkins—to uncover their secrets to transforming financial struggles into millions through strategic investing. Skipping the usual advertisements and introductory segments, the conversation dives deep into investment methodologies, mindset shifts, and the emotional resilience required to build substantial wealth.
Understanding Risk and Bucketing Investments
Chris Sacca emphasizes the importance of recognizing and managing risk in investment portfolios. He introduces the concept of "bucketing," where investors divide their assets between riskier investments (like the stock market) and safer options (such as treasury bills).
"Any money that you have invested in risk assets, the stock market is a risk asset. You have to mentally, every time you check your account, reduce it by 70%."
— Chris Sacca [02:13]
Keeping It Simple: The S&P 500 ETF Approach
Sacca advocates for a straightforward investment approach, suggesting that most individuals can achieve significant wealth by consistently investing in low-cost index funds like an S&P 500 ETF. He highlights the power of compounding over time.
"It's the world's cheapest way to invest. And you just put money in there every week or every month and you don't think about it."
— Chris Sacca [03:58]
Mindset Shift: Viewing Every Dollar as a Hundred
A key takeaway from Sacca is the psychological shift required to view each dollar as a hundred-dollar investment, fostering a mentality that prioritizes growth and investment over immediate spending.
"When you start thinking of every dollar is $100 and it will be $100 at some point, you start finding money in your life."
— Chris Sacca [14:53]
Leveraging AI and Social Media for Investment Insights
Sacca discusses the modern tools available for investors, including AI and platforms like TikTok, which he uses to identify emerging market trends before Wall Street catches on.
"You could go in, chat GPT and say, hey, this is happening. What publicly traded companies are likely to benefit from this?"
— Chris Sacca [35:43]
Success Story: Pandemic Investments
Reflecting on his investment journey, Sacca recounts how he turned a $20,000 investment into $2 million within three years by capitalizing on pandemic-induced trends, demonstrating the efficacy of his observational investing strategy.
"During the year of the pandemic, I turned a four and a half million dollar brokerage account into 35 million."
— Chris Sacca [30:01]
Navigating Real Estate Investments
Glenda Baker and Bill Perkins delve into the intricacies of real estate investing, sharing personal experiences and highlighting common pitfalls. They stress the importance of thorough due diligence and understanding the local market dynamics.
"It's critical to understand what you're buying. Not just having a great real estate agent, not just having a great inspector, but getting in the weeds with it."
— Bill Perkins [43:19]
Avoiding Ego-Driven Purchases
Perkins warns against making investment decisions based on ego or the desire to impress others, advocating for practical choices that align with long-term financial stability.
"Anytime that you're trying to impress somebody else with what you have, I just going to ask you, just, let's just rethink that."
— Bill Perkins [45:34]
Learning from Mistakes
Both experts share candid stories of financial missteps, such as Perkins' experience with impulsive luxury purchases that jeopardized his financial stability. They highlight the importance of learning from these mistakes to foster better investment habits.
"I made purchases based on Ego. And I let people that didn't matter influence me to make purchases that I shouldn't have."
— Bill Perkins [53:35]
Building Generational Wealth
Baker discusses strategies for passing wealth to the next generation responsibly, emphasizing the significance of timing and education. She advocates for giving assets to children when they are mature enough to manage them effectively, thereby maximizing their impact.
"Giving a smaller amount to your kids at an earlier age will be more impactful and more fulfilling than waiting to you kick the bucket."
— Glenda Baker [73:16]
Maximizing Fulfillment Through Strategic Spending
Glenda Baker introduces the concept of "memory dividends," encouraging listeners to allocate their resources towards experiences that offer lasting personal fulfillment rather than solely focusing on accumulating wealth.
"Maximize fulfillment, and so they will keep you safe and maybe you'll save a certain amount of money. But you're the driver."
— Glenda Baker [62:28]
Overcoming Psychological Barriers
Baker identifies the fear of wasting life as the biggest psychological obstacle in financial planning. She urges individuals to prioritize meaningful experiences over excessive saving, advocating for a balanced approach that ensures both financial security and personal happiness.
"The biggest psychological crime is people fear running out of money instead of fear of wasting their life."
— Glenda Baker [63:35]
Legacy and Responsible Wealth Transfer
The discussion wraps up with insights on how to responsibly manage and transfer wealth to ensure that it serves as a positive legacy rather than a burden. Baker emphasizes the importance of intentional planning and education to empower the next generation.
"Whatever you're going to give them, you know, some people, like, I'm not giving my kids anything. They got to make it. I had to make it."
— Glenda Baker [76:56]
This episode of The School of Greatness offers a wealth of knowledge from three experts who have navigated the complex terrains of investing and real estate to build substantial wealth. Chris Sacca provides actionable strategies for simplifying investments and leveraging modern tools like AI and social media trends. Glenda Baker and Bill Perkins offer deep insights into real estate investments, emphasizing the importance of due diligence, mindset management, and responsible wealth transfer. Together, they inspire listeners to adopt a balanced approach to wealth-building that prioritizes both financial stability and personal fulfillment.
Key Takeaways:
By implementing these strategies and mindset shifts, listeners can embark on their own journey from financial struggles to achieving millions, unlocking their inner greatness along the way.