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From $0 To Millionaire | Investing For Beginners with Dumb Money

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In this episode of the Iced Coffee Hour, Dave Hanson joins friends Graham and Jack to discuss his journey from a ten-year-old aspiring radio DJ to managing over $25 million in investments. After selling his voice-over production company at age 22 for enough capital to move out of his parents' home, Hanson worked corporate roles at Broadcast.com during its acquisition by Yahoo before transitioning into full-time investing. He explains that while he initially relied on high-risk options trading and YOLO moves—such as buying GameStop shares—he eventually learned the importance of risk management through painful losses. A significant portion of his wealth was accumulated via stock options granted when Yahoo joined the S&P 500 in 1999; although these vested over four years, they were underwater for much of that period due to the dot-com bubble crash, teaching him valuable lessons about patience and market volatility. Hanson details his current investment strategy, which involves a "fun money" brokerage account holding approximately $10 million alongside real estate assets in his primary residence, though he avoids additional property management to prevent administrative hassles like tenant repairs and maintenance issues. To navigate stagnant or declining markets without selling shares at a loss, he employs covered calls on volatile stocks like Tesla, Amazon, Apple, Palantir, and Neo. By writing out-of-the-money call options, he generates premium income that offsets potential losses if stock prices drop slightly while capping upside gains if they surge significantly. He also utilizes margin loans strategically to fund speculative trades or pay taxes without liquidating his core holdings, a practice similar to what fellow investor Kevin O'Leary advocates for maintaining full market exposure even during tax obligations. The conversation shifts to the evolving landscape of digital assets and NFTs, where Hanson reflects on giving away 14 "Crypto Dave" NFTs that quickly gained value in the secondary market despite their initial zero cost. He contrasts this with his father's original Disney animation cells from classics like *The Little Mermaid* and *Beauty and the Beast*, which remain unframed in a garage, highlighting the tension between physical art preservation and digital tokenization. Hanson acknowledges the speculative nature of NFTs but sees potential for artists to create one-of-one digital versions backed by real-world services or mentorship opportunities. He also touches on his Bitcoin allocation, currently around two percent of his net worth, noting that while he believes in long-term growth, he maintains discipline against emotional trading and advocates for 24/7 market availability as a potential future improvement to the financial system. Looking toward the future of content creation, Hanson announces plans to pivot the original *Dumb Money* YouTube channel into an incubator platform for new creators rather than continuing his own vlogs indefinitely. The team intends to hire three emerging talent and provide them with production support, editing resources, and a salary structure that could allow them to quit their jobs while building audiences on the network's infrastructure. This initiative aims to solve common learning curves faced by solo YouTubers who struggle with monetization algorithms and content consistency. Hanson emphasizes that this approach offers mentorship opportunities for aspiring creators who lack the capital or experience to launch independently, effectively turning a successful channel into an educational ecosystem where new voices can thrive under established guidance.
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hey there dave here welcome back to the 44th ever episode of the iced coffee hour i'm dave with my two good uh friends here we have graham we have jack and we're ready to talk about iced coffee but how much is the podcast made you you funny you should ask it's made forty eight thousand three hundred and seventy nine dollars and forty six cents wow wow that was good matteo you gotta tell us what that breaks down to that's amazing thank you so much dave yeah well dave thank you so much for coming out here absolutely i'm i love coming to la i don't get to do it that often so uh th this is the first time i've been on an airplane in a year how was it it was actually i'm fully vaccinated now so uh wow that's that's why i'm that's why i'm here that's incredible um but still everyone everyone wearing their masks i i absolutely would be freaked out on a plane even with masks without the vaccination so i was super happy to be vaccinated but everything was fine people were wearing masks everyone was well maintained and yeah we flew to utah to meet with the strad man and that was our first time flying and probably the same about a year and a half and we were surprised i mean they were so stringent on everything i think they were taking taking temperatures as you were like going through like certain things i felt safe like i felt probably more safe on an airplane than i would like going out to a restaurant really yeah i felt nervous it was just because yeah because you're gonna crammed in a small space wouldn't i think that you're you're crammed in a small space but i think getting onto the plane is the riskiest part because actually on the plane they have like good air circulation they they turn the air over inside the plane way more frequently than a restaurant yes i think there's way more liability if if an airline messes up they got a lot writing if a restaurant messes up it's like you can't really prove it's the restaurant you know i don't know anyway if you have 300 passengers on a plane all get covered you know yeah well anyway thank you so much for coming on today could you tell us a little bit about yourself for people who aren't familiar with you i love the dumb money live you you know us from dumb money live right you may know me from dum money live that's just uh basically we started that when we went into lockdown and we started putting our video conference calls that we were just having amongst my two friends chris and jordan talking about stocks what are we doing in the market and it kind of turned into a show but before that we had an original dumb money channel that was all about our startup investing which we again we just decided to start taking cameras with us to meetings business meetings that most people would you know never see but we kind of thought of it as the anti-shark tank where basically we were we're entrepreneurs we're trying to find the next big startup investment and it was hopefully kind of an interesting vlog style format to uh do that give us some click bait here we got to click bait the title how much money are you investing with give us some stats that we could just hit him in the beginning i can tell you that 25 million dollars is where is that where we are now we're more than that okay but at the end of the year we had turned around 10 million into 25 million so that's that's kind of what what we're investing with we're investing our own money we're not a fund we have nothing to sell we had a really hard time with youtube because we didn't have ads running at all and so nobody was able to even find our channel at first and so as soon as we turned the ads on people started finding the channel yeah just you know took took a little uh growing pains to learn that what do you mean by we are investing with 25 million dollars it's me and my two buddies and we have kind of just done this our whole lives we well not our whole lives but once we sold a software company we had some money and instead of going to work for another company we started to start investing in other startups all right so we got to go way back tell us from the beginning how do you start a start where a software company sell it then turn 10 million into 25. we got so many questions here there's so there's too many pieces to the puzzle that are missing right now you just have to subscribe to the channel that's all you really need to know that's so i don't know there's not a it's not an easy one two three started like process age ten so when i started age ten when i was ten years old i wanted to be a radio dj okay and so that's where my kind of fascination with media and that's the whole reason we're on youtube now is i just thought now that i'm kind of retired and working for myself why not have some fun with it and make videos um but that's i i don't do it for a job it's just something fun to do sure um so when i was 10 i wanted to be a dj and that made me want to eventually go to film school i went to film school never actually got to use that in my professional career at all i went to um so i went to nyu graduated lived in la for a year okay um thought i was going to be in the entertainment industry decided that wasn't for me so then i went into uh basically radio production out of my bedroom and i was doing voiceovers and production for stations all over the country i sold that company when i was probably oh god what was that 20 years old and uh 22-ish i went to work for a little little startup company called broadcast.com right after yahoo had acquired it from mark cuban for four billion dollars it was a huge huge thing that put mark cuban uh on the map right uh and so from that point i was working a corporate job at a big startup company and that was really my business school education film school didn't prepare me for the business world but working at yahoo during the heyday of you know before before google was a thing yahoo was the you know the home page of the internet so before that it was aol remember that aim yeah we'd say that you could do the voiceover then well how do you've got mail oh if that doesn't make you want to hit the like button i don't know what will two good questions how much did you sell that voiceover company for 22. that was that was not like a life-changing amount of money it was uh it was not much but it was enough so that i could move out of my parents back house which is where i was living at the time i put foam all up in the closet and i was doing that out of their back house why would they want to buy it did they grow it yeah so we were doing um production for radio stations 40 40 or so stations all around the world i was the voice over uh for power 100 fm and istanbul turkey because they liked american sounding voices and i was cheap i was running ads in the back of radio and records magazine wow which is like a print publication and uh yeah i was trying to give us an example of like what you would say like welcome back to power 106 where hip hop lives well so in dj voice or in in like announcer voice like how you would do it like like 4x96 is serving up hits that's the that's the friendly voice and then you have the uh uh z 100 fm that kind of voice and then you have focus that is so good don't do uh you're putting me on the spot so uh the best mix of the 80s 90s and today the new mix 102.9 i'm dave hanson we got another all request and dedication hour coming right up you know you can start puking like that cool yeah so jack you got to i need a script i can't just freestyle it that's that's the hard part um i yeah hey graham i'm calling in to make a request welcome to 97.1 i don't know i can't do it welcome to smooth jazz oh my god 87 points i i actually got to be a smooth jazz dj for one night when uh we were again i was 18 years old i was in high school and uh the the program director for the radio station that i was working in was moving over to turn this smooth gas station into a top 40 station and the last night before we pulled the plug on smooth jazz they put me on the air from like you know 8 p.m until midnight and i got to you know switch the station over into being a top 40 but i got to do smooth jazz for a night that's really nice i didn't know any of the music i was playing it was great you should have done the intro in that voice welcome back to the 44 back to the 44th ever annual it's amazing i need a script too that is cool all right so yeah so how did you get a job like a corporate job with a film degree well it was a production kind of company it was broadcast.com which was streaming audio stuff onto the internet and later video and uh i started um what was my first job there was i was like a producer who was uh helping coordinate production like just getting getting satellite feeds in and putting them into an encoder and sending it out on the internet and over the course of 10 years in that corporate job that was my education and i basically did 10 different jobs i was a website manager i was a director of marketing i ended up in the marketing department and that you know we did so many cool projects that yahoo never really got credit for things like crash the super bowl that doritos super bowl promo that for years they would they would let people submit their commercials and then if you would get chosen that was originally a yahoo promotion that my team did so interesting so then what evolved after that that got you into investing large sums of money yeah so all during that time i was fascinated with investing and i was investing the small sums of money that i had and learning and that was probably you know the the reason that i feel confident in investing now is because i've made so many mistakes when i was younger so i was i was doing just crazy yolo option trades before yolo was even a thing like because instead of having the capital to actually buy shares of a company i would be like oh well i can control 100 shares at a time if i buy these out of the money options knowing that i'll probably lose all of my investment but is kind of gambling meets um investing but what year was this but first we have to talk about one of my favorite services out there let me guess privacy.com you betcha i love privacy.com i just love it so much it's just so good i know man me too and trust me you guys will feel the same once you start using it too privacy.com is an amazing service that protects your credit cards when you're buying things online so say goodbye to fraudulent charges canceling subscriptions and all of the worries that comes with buying things online here's how it works instead of handing out my credit card to everyone i can link my credit card to one of privacy's virtual cards and then i can pay for things using their card instead of my own and that's not even the best part these privacy cards have massive perks such as being able to pause the card instantly set transaction limits and cancel with the click of a button this protects you from ever having to worry about your card ending up in the wrong hands plus if you go with the privacy pro plan you'll actually get one percent cash back and this is outside of any of the rewards you receive from your real card oh my gosh one percent cash back people are actually making money with this plan the cash back is super nice so do yourself a favor and protect yourself when you're buying things online with privacy.com there are so many perks i literally can't cover them all you will also receive five dollars by clicking the link below or heading to privacy.com ich you really don't want to miss out that is privacy.com ich thank you so much privacy and back to the podcast that was well all through college so that was in the late 90s okay um how much were trades back then it was ridiculous so back before so i i got in on you know using online i used e-trade that was my first online brokerage but i had an old-fashioned broker who was a human being who you would call up and have to make a trade and i think it was like 50 every time wow you wanted to buy or sell a share and so and options were even more so once e-trade came around with their i was at 30 at the time or something that seemed like oh my god i can do 30 trades now and then they got cut in half and 15. now i remember i used scottrade back in the day and i think that was i think it was between seven and twelve dollars per trade either way so it didn't matter how much you wanted to buy either it's like if you wanted to buy one share for 15 well that's going to cost you 12. that is a lot to make up yeah so and that's and that's another reason that options kind of helped with that because you had a better chance of being able to pay the commission on this thing that would have i mean it was it was not a great investment strategy but i want to hear about your options trading and how that's going because uh some of the earlier episodes of this option i love to talk about options i love you know what jack would have been made more money though had he just bought the actual stock instead of the option i wouldn't buy instead of selling call options you were writing call options on uncovered no covered calls i was still totally like making money but i was mostly making it just due to like selling out of the money call options yeah so i was making money on the appreciation and then i would end up losing money most of the time on like the actual options contract yeah that was after my first 20 out of 20 profitable options trades those were 12 true options yeah they were they were very very conservative but uh yeah that's but that's what you need to do to learn and get into it i i love you doing it and that's kind of why we do dumb money is to just get out there and let people start thinking about investing and start thinking about things that they may have never thought about i think that the whole idea that robin hood lets you invest for nothing and it makes it easy in a game i love that yeah i actually kind of agree with you i think so long as people are investing even if they're making mistakes losing even like a few thousand dollars at least they're out here doing it you know well just know your risk tolerance know what you're willing to lose and you should be okay with it if you know that i'm i have set this money aside this is not what i need to pay my rent this is not what i need to pay for my life expenses this is just extra money go for it there's not much of a difference though between robin hood right now in a casino i'm all for the gamification of it i love being able to get a free stock and you go and see the confetti and you go and swipe up to buy a stock and it just like people are clapping for it's fantastic i love it but there there's not much of a difference between that and putting your money on disagree i disagree most of my friends that use robin hood don't do these crazy like short-term out-of-the-money call options they just buy like common stock like they just buy equity it's that's how i see a lot of my friends do it and i know a lot of people use it as a casino but i wouldn't say that it's like comparable and i think you know you can do both you can actually go to a casino and be very conservative in your gambling right you know the odds you can play a game that you have that 51 there's a there's a smart way to do anything and then there's the gambling way to do it and i think you can use robin hood for either and i think that it's fine if you want to have fun sometimes and just make some crazy i i bought gamestop i did and i knew that i was either going to it was going to be a huge winner for me or i would just cut my losses at about you know half and yeah what did you buy gamestop at i have no idea when i bought it in the first the first wave of uh game stops insanity um it must have been like 50 bucks 60 dollars around there okay i do so many things like numbers don't mean anything to it okay but basically i know that i lost about half of what i invested wow okay that was what i was this is my risk capital that i was you know not needing the money and for me it was i don't really remember but it was probably around a hundred thousand dollars and that was just that was the gamble so you bought my shares that i sold and you're comfortable losing a hundred thousand dollars yeah how i i i feel like even for me it's like locking in a loss of 100 grand i immediately think like all the things i could have done with that but are you also thinking of all the things that you can do with the money that you haven't sold and all of your crazy stocks that have appreciated that you're not willing to sell because of uh tax implications no but i feel like losses for me are so much harder than the game like like the gain i know it's kind of like all right it's there i could use it if i need to but a loss especially a realized loss so that to me is like all right that money's gone it's definitely not coming back and i could have bought all these other things instead yeah i could have bought some really nice vacations that's the one thing that it really gets me because i i'm a little bit cheap when it comes to actually spending money on things but i am less cheap when it comes to like the opportunity of making money on something so yeah that would be a really nice 50 000 vacation if you think if you think of it that way but i think of it as a loss that i get to now not have to pay taxes on some of the money that i made in another stock so it's a 50 000 yeah loss okay you're great at separating emotions and investing that's a total skill a total skill yeah and so probably the thing that i learned when i was young was that buying the dip is a thing i would just get freaked out it's going down it's never coming back i can't afford it this is too much i was maybe on margin and forced to sell or just like had paper hands and had to had to lose out on on stocks that had i had i just held on for another you know year even it would have totally turned around i lived through the the dot-com bubble right i was working at yahoo when the stock they gave me all this it was 1999 when i started working there that was the year they were added to the s p 500. and they gave me stock options on the day that i started and that was a day that they were added to the s p so that was a all-time high for them and they kept going up they kept going up within you know a couple months i was a paper millionaire and i never made more than like fifty thousand dollars a year at that point in my life and so that was just insane but i couldn't sell it and uh within the time of the vesting of those options uh i was underwater in those options pretty much for the entire 10 years that i was there they kept giving me more and more so it it worked out what's the lock up here is it a year it was one year of vesting for the initial i think it was a four year vesting but for the initial hit it was a full year before then they started investing monthly quarterly or something yeah so were you able to sell after that year yeah but all those were worthless they were underwater so i had i had to wait for them to give me more options the next year so it's just call options that they buy like on your behalf basically they're basically a bonus or something yeah and then they expired worthless expired and they were actually 10-year call options and they expired worthless 10 years later that's how bad the dot-com bugger was yeah i have no idea yeah that's that sounds like.com bubble was terrible for some of the stocks cisco was a big one cisco was one of the biggest runners uh during the dot-com bubble and even today like 20 years later it still has not recovered to the same price it was back in 2000. i found an old login on my yahoo where you tracked your portfolio at the time and like half the stocks on there were completely out of business like zero is quote even available including yahoo's ticker because they were required so many times uh and then the others like if i had stayed and so i can't remember which which ones but if i had stayed in some like tried and true companies amazon was one of the stocks that i held back then that you know it it was going down down down and i lost money and am how do you lose money in amazon in the 90s like i must be the worst investor ever but it's it's you know you sell without uh waiting are you worried about another bubble today where do you see the warning signs flashing i wish i had that crystal ball i i i'm worried about it but i'm not proactively uh in fear about it so when we had the big crash in march last march yes we're already in march again yeah i know did this crash correspond with the last crash almost no no no no wonder if it's like bitcoin yeah it's gonna be like it's exactly it's an ankle thing very close actually i think the bottom was march 23rd so we'll see march 11th right i don't know i don't know the exact top but no no it was late february i think was the time was it and then it slowly started going down i was on vacation at the time and lost a million dollars wow because i was not paying attention and uh that is a huge lesson but i was able to aggressively get in there and um i basically was shorting the spy and also just shorting it and also buying puts on it yeah and i was able to not only get back to break even but i i doubled my net worth in the past year wow so you were buying puts in as it was as it was falling apart i was a week late so i made a video on my uh my first channel hey there dave here all about how i paused the stock market as it was in free fall i watched that video i watched that video back then i'm gonna check that video out right after you would like it because it does talk about how i used options too that's amazing explain how that works for everybody who is not going to watch that video but first we have to thank our sponsor surfsharkvpn have you ever been searching how 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is down below in the description so thank you so much surf shark for sponsoring this episode and back to the podcast everybody's gonna just watch it we'll just link to it up here it's cool easy no um basically when the stock okay when stock prices are going down if you want to not let and you own that stock and essentially i'm i'm saying the s p because my portfolio was a pretty good representation of the s p i had you know amazon and apple and microsoft and you know all of those tech companies that were going down at the same rate as the s p um that's kind of what my portfolio was doing so i used the s p as a proxy for that and essentially as the market was going down i was buying puts so that that basically gives me the right but not the obligation to buy you're forcing someone else to buy the shares away from you yes when you sell when you buy and you buy a put you're forcing someone else to buy the shares and so it's a hedge yeah if you have to exactly and and but i but i was basically it was a covered hedge because my portfolio was backing it up so i knew that worst case i'd break even and and sit on the sidelines during a recovery but best case it keeps going down and i'm going to profit on it continuing to go down so smart i just so i love that that's so cool so wait so you how much did you make during all of that was you said a million dollars well i lost you but you made a million but i hadn't actually sold anything so i didn't actually take any losses so um i i was able to before the market even started correcting i made a million dollars back so that was an actual made million once the market did correct uh in all it was probably a million and a half in in a month and a half period wow that's incredible but then last week i mean over the last i don't know when this is going to air but remember when the market was going down so bad for like five days in a row that's a million dollars right it's it's it's easy it easy come easy go but you just have to kind of be prepared now is that in the 25 million portfolio no that is just in my portion of that which is about 10. okay and you know together it's it's probably we're we don't all disclose every dollar so i i say that my my main investing portfolio is about 10 million chris is i think is 25 and jordan doesn't disclose his so we're at about 35 of this does jordan not disclose his because it's the lowest or because it's the most it's got to be one or the other that can't tell you either one on that but uh i think it's the moment jordan did well because he was uh one of the co-founders of the software company that we sold and i i came here chris and i came in a little late on that not as co-founders but his founding partners okay it's the most i think i would be too i think as as i've grown my portfolio the less risk i want to take i'm okay taking like thrown 10 grand here and there that i think my 10 would be the equivalent of your 100 where if i were to lose 10 and lock in a loss it is what it is so i think maybe you just have a higher threshold but yeah but i also have a higher demand you know i want to make more money like that's that's my drive yes to to get to the point basically i got to the point where i knew i would not have to work when i hit i think two million dollars and from there i was like okay what do i want to do with my life what what can i do i just want i want to travel i want to have fun i just want to i enjoy the market i enjoy making videos i what do i like and so that's kind of what i have focused is that the point where you decided you're going to do the financial independence route when you hit two i mean i never really thought of it as you know following someone's system but yeah when i when i had two million dollars in cash or in equities i was like yeah that's good i know that worst case scenario i can stretch this out and survive the crazy i'm still just like the same level of worried oh it doesn't matter how much money i have i feel exactly the same in terms of like i'm worried like something's gonna happen i'm not gonna have enough money to pay for it all the time still well i mean what are you invested in now are you are you fully invested in equities no uh i think eight well if we're are we talking gross i think like eight and a half uh real estate four and a half four six stocks uh two something cash and then i don't know 600 grand and just like random yeah 700 and random but 304 gt oh yeah four gt yeah and a 4g team that's a good investment that's i would kind of like that appreciating asset if someone offered me uh how much 350. no it's not worth it to sell for 350 four i would sell it at four yeah i feel like that's i would get a golf i would get the golf version of the 4g i'd spend 450 and get a golf so i've come out 50 grand of my own money by the gulf well i'm gonna have to go out to vegas and see that vehicle so you could buy it you could buy it no no i'm not a car person to me that's that's just not that's never been my thing i literally have every car that i bought it was like they gave me this is a loaner at the dealership and i'm like yeah that's pretty good i'll buy that next time like my i have a range rover velar now and i had that because it was like those are nice those are pretty deluxe great they're not as bad as you would think so that's a four cylinder right you're a cargo yeah so it's a i i could be wrong i mean yeah i believe it's a four-cylinder car so it gets really good gas mileage the lease prices on those cars are really affordable they're not bad and they look so good you could throw up a picture of this and just see if i'm right or not but i liked it so actually the dealership gave me an evoque and i was like oh i don't like those and i was like yeah it's a little squatty in there yeah i didn't really like it but then when i turned it back in i was like what is that it was all shiny and new in the in the lobby so i took that home and i think my lease is almost up so i don't know what to get next tesla tesla model x that's really what i've uh i've always said that that's what i should buy you should i don't drive though like i think yeah the car drives exactly i put 5000 miles on my car this past year that's a decent amount of the lockdown and everything that's a decent amount sure that i play effect i like the model x because of the uh the doors that's really if get one if it was just a little bit bigger they look cool back to the future is my favorite movie i've always wanted a delorean so if i bought a stupid car it would be a uh delorean really yeah andre jick wants a delorean really badly really yeah and it made sense like as soon as he told me the tricked out version with the yes he does okay yeah but as soon as he told me that he wanted a delorean i'm like wait a second that's a great car to get i think part of me wanted a delorean but i'm not going to steal it really quickly yeah okay right now but funny would it be if we all three got them and then drove them just buy his house they've gone up in value a lot lately those cars used to be like eighteen thousand twenty thousand dollars a few years ago they're all now selling for like 30 35 grand do you think it's just all alternative investments right now are just like picking up yeah if you're buying nfts of like random things then yeah there's a lot of alternative investment going on everything like watches pokemon cards like everything is super hard so odd why i don't know i mean hobbies people are picking they have too much time right now they're looking at stuff we've had a lot of free time and some free money got dropped in their bank accounts and i don't know i've never really been a collector of anything either so it's pokemon's never really made sense to me we had on dumb money that thousand dollar fake pokemon oh we should talk about the bible so let me explain this so sebby sends me this video minutes after it happened so you need to watch this immediately and react to it and for for a long live stream like that i'm like let me at least scroll and like see what i'm going to react to and just make sure it's worth it i started watching it and i couldn't react to it because i watched the whole thing because i i couldn't take my eyes off the screen so you bought at the time the most expensive first edition box of unopened pokemon cards ever ever it was right after logan paul bought a 300 000 box we were scrambling because we wanted to open one we knew that the market for these was going to accelerate because they're now famous and now people are going to want these boxes and so we bought one uh and had 2 000 or however 375 thousand dollars yeah um and the guy who actually was on logan paul's show hand delivered it to us he he secured one brought it to us we had uh leonhardt and some pokemon experts standing by ready to uh to look at it and uh then it comes time to open it and it was a resealed box there were fake uh like they were real cards but they were not the cards that were supposed to be in there they were not first edition cards and it was just we we had no idea what to even do now we were not even expecting this live stream to be a big thing at the time live only like 2 000 people simultaneously were watching it was small because it's right it's a smaller channel yeah uh and then within within two days there were you know quarter million views on a video that basically it was a huge failure we had people saying how poor the production was yeah you do a box break without having a camera on the box yeah i'm like dude i was i was buying gear off of amazon the night before just to be able to give you that much quality wouldn't you think though that if you were spending 375 000 on a box you know like a few weeks ahead of time to fly leonhard out there like he was collectibles oh he's low okay he's local all right okay all happened so quick it literally i had collectibles guru uh in dms on twitter uh in one stream and then my amazon cart in in the other and it was all happening within a few days so what was your immediate reaction when he opened up the box and it was like all fake what was your response it was it was just shock i didn't even know what to do like do we pull do we pull the thing off the air is this what do we do but it actually just ended up being the only thing that was good about it i mean nobody would have ever seen our 375 000 pokemon box had it not been fake so i mean we had people saying uh you you staged this whole thing i can tell you this was not at all staged and it was it was shocking and i i didn't even i it was like i was in my own world right i'm also monitoring audio and people's mics are going out and so it was the whole thing was a disaster so you were in shock you weren't feeling like angry or you weren't feeling sad or no no i mean it wasn't my money first of all so that made it uh completely like oh well right sucks to be chris right now but no we hadn't actually transacted the money so it wasn't like we were going to be at a you know boss on this i'm i was actually glad that we didn't you know wait and not open it because yeah it would be more dramatic to uh do a box break for whatever the you know event charity thing is eventually and have it just be already a perfectly sealed box i'm so glad that we actually opened it because that would have been a huge disaster now you didn't pay for it right ahead of time like you had the cash but a suitcase full of cash because that's how you either you either buy it using bitcoin or cash and so we we it's a wire transfer not workers apparently they don't do that in this crazy pokemon are you serious it's either cash or big i think it was all we actually did end up giving him the suitcase of cash like uh that day a week later after he sourced you guys what do you do with that much cash though that's a pain to deal with that much cash uh even getting that much cash was a huge pound how do you do that you they basically give you a clear garbage bag and you're just walking through the parking lot with 375 000 in cash before you can put it in your little suitcase i'll i have some uh b-roll clips that you can i would love to insert into this now to get the cash you didn't have to go in like an airplane or take the cash anywhere you just you just no no a local local bank uh they had security there but it was not like an armed guard or anything it was just like a dude who worked at the bank who said oh yeah if you're parked right there i'll keep an eye on you wow did they question what this is for i don't really recall they must not believe yeah i'm just like i was just so nonchalant well i think we in advance like told them you know because i don't know that they always have that much cash just sitting in the vault so i'm sure that there was like an order in advance so they knew we were coming it wasn't just like hey i want to write a check for 400 thousand dollars and take it out in cash what bank is it it was a wells fargo nasty that's what i so it's it was actually chris's money i would never buy a 400 000 pokemon box but it was his money his bank i always give him a hard time for wells fargo because every time he needs to wire money he physically goes into a branch why because he's an idiot jp morgan yeah i get free wire transfers now chase i use i don't know that's him now that's nice that's funny no i uh i use bank of america and i can do it all on my phone and if you watch any of the original dumb money channel you see like every time we need to wire money for some startup we're investing in there's always like this scene of us driving to the bank so chris can do it while i'm doing it on my phone yeah he's just i had a terrible experience with bank of america two terrible experiences the first one was i wired money from one account to another and i forget what it was but i i think i switched the routing and account number or there was some sort of like a common error that was there the wire was sent but it was never received and it was 150 grand oh try tracing that back and trying to reach somebody at bank of america they have wire hours that close down at like 5 p.m eastern time it takes like three hours just to reach somebody who's in who then is like oh we gotta transfer you over to this person and then it goes to a voicemail imagine waiting on hold for like two hours to go to a voicemail it was terrible eventually the money was reverted back i was so thankful but that was really just a scary experience i had something similar happen with e-trade back when i didn't really know what i was doing and i got into some some kind of a position that i should never have been in some naked call position or something that they ended up like margin calling me and fed calling me on the same day and just emptying my my entire account and i'm like what how how you can't do this where'd everything go you you shouldn't have even let me get into that trade i i am not qualified to make that kind of investment but i can't remember it it worked out in the end i finally got through to someone who yeah understood but yeah so what's the plan with the charity box break are we going to be selling the packs or how does this work i'm not sure exactly the logistics of what we're doing but basically it'll be similar to other charity box breaks we'll be selling packs we'll we'll be giving some to uh people in the dom money community we'll be giving some probably to some creators giving some to creators how do how do creators give and also what constitutes a creator [Laughter] i think you probably both qualify i'll um i'll definitely keep you in mind yeah yeah let us know okay okay now would you do something like an nft associated with that because i feel like you could either do like the raffle thing and you buy into it and you raffle off you would make a lot more money for charity i feel like doing the raffle the bidding system was interesting what logan paul did but those prices were just insane but he had the nft attached to it so what is your thoughts i don't know i i would love to figure out an nft that makes sense it's just so hard to figure out something that makes sense i own a logan paul nft i have no idea if it'll ever be worth anything which what did you buy i bought one of the original uh three three thousand or two thousand that he did for one ether each okay i bought one of those in the aftermarket when they had already depreciated they depreciated that fast yeah what about the uh the original box break one that's the one that i have so he issued that's where he made his five million dollars no no no no no no there there's box break but then he had 44 unique ones 44 unique ones when you received a pack you also got one that's what i'm talking about i don't know what those i i haven't found those in the in the secondary market so at all i haven't seen them but i really shopped i looked them up once and i saw the last one sold for 38 500 which i was shocked yeah i does any of it make sense really do you want to have a uh graham coin maybe i think i think i think there could be a lot of potential i think for an nft kevin mentioned this in one of his videos uh and we mentioned it with uh blau on the podcast last week doing an nft that's valid for like let's say one phone call a month or like one mentorship thing a month or something like that where they have access to me for an hour and that could be resold in the future basically a resellable subscription correct the person who bought it the first time can change the price yes and then you would get a percentage if the transactions correct happen yes so but it would be backed by a service yeah uh in terms of the artwork i see there being some value for certain pieces right now it's a crap shoot i think right now it's like throwing a shot in the dark is is people going to be a household name or is he going to be the people is one of those beeple is because he was the first the first to have these huge six million dollar sales i think that that kind of cemented him his place in history and he will continue to have value i think that that is kind of like owning a picasso right um i think that a bunch of these other random things are going to disappear i also like uh crypto punks because they were the original original yeah and uh so i gave away 14 crypto daves for free and i'm waiting to see if anyone sells them right now someone's offering a hundred dollars for one there's no value oh this this was from your video right yeah so i just just just for fun i thought yeah just to see what the process is i want to show how easy it is to actually anyone can create one of these things and what happens if i just give them away and does anyone want them yeah like within an hour people were claiming them wow um i gave away one every hour for 12 hours and like people were already offering you know they were free and then five minutes later they were 50 and there's someone right now there's an offer for like uh 170 or something so like there's no value there's you can't do anything it's a picture of me pixelated with a stupid hat and glasses that's it i'm trying to get my dad to do an nft so he used to work for disney throughout the 1980s and 1990s as an animator and that's cool so he's done a lot of we actually in this box over here we have a lot of the original animated artwork from like the little mermaid and uh yeah and like beauty and the beast throw that in a nice climate controlled environment this has been sitting in a garage for like 30 years i'll show i'll show you some pieces actually you know what um you know what while we're on the topic let me pull out one piece here so much for staying on track with a nice narrative dude we are just like jumping from topic to topic i'm with it though i i like it yeah what who is who is this isn't that 101 dalmatians yes yeah yeah so he was working on this yeah 101 dalmatians how cool so this is one of the original disney cells i have no idea how much these are worth i'm never going to sell them obviously but he has his entire career basically just sitting in a garage right now and almost none of it is framed but eventually i want to get them all framed but what was that this i want an original though that's so i don't want a token version but no here's the thing i was telling him because he's he's just always done art um i think art in this sort of form it's difficult to sell but if he could create a digital version of his own version of like you know his own animations and sell an nft version of that just a one-of-one i think then it has and maybe i'm biased because like i'm talking about my dad here so obviously i'm gonna be like that bad but i think there's something to be said about buying artwork from real artists and that having value at some point no absolutely and i think a digital version of a one-of-one from an artist that you respect that you like that definitely value and i don't know exactly how you're going to display it i guess all frames in the future will be digital and you can probably pull up whatever you want but you could pull up any art really so the only the only thing is i own this and i can prove it because i have a copy of the blockchain right so i agree i think it's kind of a toss-up right now with evaluations of nfts i know someone who made their own nft like digital artwork they put it up online and sold it for like 400. and they have no following or anything like background and digital like art or like design or anything like they just sold it for 400 and they're like oh that was my first nft more to come wow it doesn't make sense well it's so cool though that people can do that i love anything that just gives more access to people to be able to sell whatever they want to make something and be able to sell it like can you imagine like if i was if i was able to have youtube when i was a kid can you imagine how like cool that would have been yeah to like make videos when you're like i don't know how old you have to be to be on youtube but like 16 when i was i was making mixtapes of me being a dj if i could have like sold those somehow back like and had an audience that would have been super cool yeah even only fans we got we gotta we gotta respect the only fans here but like there are creators making over a million dollars a month yeah on only fans it just goes to show i don't know if right now does people have so much money to spend or if we're finding just new creative ways to make money it's a little of both yeah jack how are you liking only fans it's great actually i'm kidding really a little community [Laughter] what do you do there i bet you would get people that would sign up for you for an only fans you would too like maybe i'd get like five i bet you'd get quite a few what would i do on there like what do you do i don't know i don't know what is that what is money teasing i just made it up this is like shaking money i don't know that's an nft in the making yeah yeah should i make an only fans i mean maybe honestly i would what if i could i produce your content i'm leaving enough of it what would we post i don't know what was the money clips with you and money i don't know basically it's like i'm in a bathtub just like full of hundred dollars yes like that would people would love that dude but it would have to be like pg stuff like i wouldn't be doing anything like crazy like pg maybe pg-13 i don't know yeah we'll see well anyway that's we really derailed your yeah we just found our podcast yeah okay let's go back to investing what's your investing strategy now what do you see in the market that scares you a little bit i'm basically the the last month has scared me a little bit and i don't know if i should be putting the brakes on if i should be you know hedging again if i should just let it ride if i should be doubling down if i i don't know what to do so i really have just kind of taken a step back and not done anything because long term that's probably the right thing to do so what about the market worries you in the last month uh the everyday being read was a big problem that that you know i don't know if it's systemic we're going to actually see this happen you know for two months in a row long term i think we're fine but we have inflationary worries we have you know there's just so many things i'm not a macroeconomics guy i just i just play stocks i almost felt a little easy about the market going down because when the market was going up like a percent every single day i was like how is this possible but to see it just trace back and some stocks go back like 20 30 percent then it made me almost have some faith in the markets like okay maybe people aren't that crazy maybe there is some some logic to this so that's not how i felt yeah and that's great if that continues for a month or you know a few weeks and then we get some some up days what i would just absolutely terrifies me is if we had that happen for five years where you have stagnation or you know just the market on on a downward spiral not not big drops not something that you wake up one day and go oh well we had a 10 drop that that's the end and now it's gonna go back up but if we have you know two percent here up one down two up one down two and that continues for a long time that is what scares me that's why you selling covered calls on your on your shares that's how you make money in like a stagnant market and that's what i've been doing to hedge against like all of my equity holdings during this like last kind of like downturn or whatever downfall whatever you want to call it do things get called away from you frequently when you do that or you no no because everything's been going down so like nobody wants jack stocks but fortunately like i've i've made a little bit of my money back i'm still way down but i would be way more down had i not sold these covered calls in my my shares are you picking stocks that have like a higher uh call price like specifically like uh like a higher premium um i this is just in my robinhood account so i have like a robin hood account which is like my you know fun money my risk higher risk money that i have my td account which is buy and hold then i have vanguard which is index funds my robinhood account it's all just like yeah high premium stock like i have a ton of palantir i have apple which doesn't really have a high premium but it's a little bit more volatile um i have neo stuff like that so yeah i will you know on the calls that i sell i can usually get like 10 of the uh the share cost uh with the premium yeah so the only thing that will really actually hurt me is if you know the stock plummets more than 10 yeah or if the the share price just like skyrockets and i'm you know upside down on the option but i still make it you get out money on the appreciation and ten percent premium as well yeah i i like doing that it it just got so time consuming to monitor it and keep moving those call prices down and you know you want to do it for your shorter you know weekly options instead of like the longer term monthlies and i usually just do monthlies because it's like less to worry about yeah so that's that's the i like about simplifying it if it takes too much mental power it's just like is it even worth it oh i'm not gonna lie like sometimes i i literally just going rob and i click sell i click call i just pick a random date and i like pick like i'm not kidding like and it works like especially considering what recently it works until it doesn't though no but this is i mean this is hedging against my my my holding so it's not like the if anything it's less volatile what i'm doing but i swear like i literally i don't even like compare premiums you know if i can get like five percent in one week versus 12 in two weeks like i don't it doesn't matter to me i'm like i'll take anything honestly that's why we buy stocks too he just goes to the top movers section on robin and he's like i just buy that one yeah all right i'll buy it i think it's my portfolio it's kind of the same way though if you think about i you know i have a lot of amazon and tesla and apple and those that is probably you know half of my portfolio and three concentrated three yeah high highly volatile stocks wow i mean apple is right that apple's my cash and then i i have a bunch of things that i play with right and so that's that just kind of keeps it fun so what's your net worth right now i i haven't even even done that calculation so my fun brokerage account is around 10 million uh my house is that's your fun brokerage account do you have a fun account for 10 jeez i thought that was like everything that's right all right that's my primary that is that's the majority okay um but how is it the fun one though well yes it's the one to keep that's a lot of fun 10 million dollars you don't need that much yeah it was only four when i started so it's been a lot of that's why i call it fun because it's and i'm gonna make i'm not gonna take money out of that and put it into a boring account i'm just gonna keep going see a fun account um yeah and then i have a my real estate is very limited to my house that i live in uh which is i don't know three three and a half did you pay for that outright or do you have a mortgage on that at the time i had a construction loan that uh i you know it was a million dollar construction loan that i kept as a mortgage for about a year and then i just decided to pay it off hmm why decide to pay off the home why wouldn't you see that as a good way to leverage your money you get like three percent on that as a cash out that's true i for me it just felt like i was more in control of all of my money if i didn't have this extra money that i was going to have to pay back at some point right just gave me more clarity and as far as what i have what i can invest i don't know it was it was kind of a weird on paper by math it probably doesn't make sense but i just thought this is the time just to get it off one less thing to think about right so you have 10 million dollars in fund money 4 million in real estate and then what else that's about it what else is there so your fun money they don't have i don't like like a lake house i don't have any exotic cars just like a couple million here a couple million there really simple right okay that makes sense like i i think having to think about money too much is just i i'd rather just not think i want to get like that it's it's it's it's overwhelming for me to think of all the things like just i got emailed today like with six different like oh this this electric account is getting billed today and like making sure i switch that over to like the new you know business account and like property tax like the accountant carol she wanted all the property tax statements i gotta get like eight property tax statements it's horrible making sure all that gets paid and like the insur the insurance i had to renew the insurances and they have to call and get the bank account information i i envy just like one place you have like a house and a stock market account and i basically stayed away from real estate because it just seems like a hassle like i get it that's a good investment it's it's a totally it's just something i haven't explored and i just am not as comfortable with it and so i just haven't done it i've been telling jack about this that uh i feel like when you really want to build your wealth in the very beginning real estate is such a great way to do that if you have the time to do that yeah it's so hands-on it's possible to get like a 50 to 100 return on your money like somewhat safely in the first year by like buying a place under market fixing it up now you have a whole bunch of equity you could rent it out you get the cash flow but as you start growing i feel like it starts making less and less sense just from like the the time aspect of it yeah i was actually looking at like a eight unit apartment building and that just seemed like it would make sense because i could hire someone to do most of the work and i would just basically be able to collect you know paychecks that would or you know collect rent that would pay the mortgage for it but it just even that seems messy because you're always trying to make sure that all the units are filled and it's just why do that when you can just sit back and watch the stock the property manager that i have takes care of like 90 of things but there's still that 10 that i have to do in addition to it and they were sending me emails back and forth today at the toilet do you want to repair it or do you want to just get a new one it's a 100 difference between the two i'm going to get a new one and then the hvac that the ducting is like so some issue with that that now needs to be fixed it's a hassle it's a hassle i don't want to be dealing with it it's enough to have to deal with five air conditioning units in my main house like there's always something that i'm dealing with and i can't even imagine doing that at multiple properties that's why if i had multiple properties they would be small airbnb sized like one two-bedroom kind of condo apartment type things in places that i want to visit but even then airbnb so much easier yep so do you not technically have an income then like how do you have capital to throw into new investments if a lot of your like worth is tied up into like long-term holds or something like that um my i use margin that's i go into margin when i want to make a speculative investment and pull out of margin and get back to uh break even or you know so most of just like the the actual stuff that you own not using margin that is like all buy and hold and then the margin is kind of just like speculative shorter shorter term trades i'll buy on margin knowing that this is this is i don't want to pay interest on this money for the rest of time but i'll buy you know when i was in gamestop i didn't have extra cash sitting on the sidelines so i went into margin to buy some gamestop and that was probably not the best idea but uh yeah that's i i use i use my brokerage account as my income and just pull whenever i need some money i pull some money out and i'm checking i've been debating doing that kevin has been telling me to do that that's what he does he has no cash in his accounts because it's all invested and he just uses margin as like a piggy bank to go and pay for anything yeah i mean it's a you can negotiate your rate down it's it's kind of worthwhile the only difference between that and a mortgage is you don't get that tax deduction off of the mortgage interest which is capped but you do get uh you your more uh your margin interest is deductible so on your on your capital gains right check with a cpa yeah not an attorney what would you do because i got the i got taxes coming up and i got a big tax bill i have the cash to pay the tax bill kevin what he's doing is he's uh basically just getting a larger margin loan against his portfolio to pay his taxes uh i'm debating it because it's like on the one hand it's just peace of mind like okay it's done i don't know anything it is what it is i'm back to square one again or i could borrow it i think if you had something that you wanted to invest in you actually were like i need to have this money to invest in this i would do what he's doing he's fully invested he's fully on margin and when he needs money to pay his tax bill he's going deeper into margin if you don't have that investment in mind that you want to do i would totally just pay it because otherwise you're paying more taxes you're paying interest and you're not putting that money to work for you in whatever because you don't have an investment but assuming i would invest it assuming you would invest it you just have to do the math are you going to beat the margin rate and uh any penalties on delaying on paying your taxes are you just going to pay it well i would be paying it because that's also you right you could just decide not to pay your taxes and pay the penalty no no i don't want to do that yeah i i made that mistake last year by doing the i didn't pay my estimated taxes because i've always i know same so stupid i just figured i'm just going to pay a big lump sum at the end of the year and that'll be fine but it's just i mean in hindsight it would have been better for me just to pay the estimated but i liked having more cash on hand especially when the market was dropping to be able to buy in even more yeah so i now make my estimated payments and i do it based on a percentage of what the previous year was which is such a weird system anyway because you don't know what your previous year was because you're always filing i'm sure you are filing an extension and finally the last i've never filed an extension so you probably don't invest in many startup companies they they're notoriously slow at getting k-1s to you and you can't file your taxes until you have all your k1s and so i end up having to push push my taxes back and so i don't know what i owe and so i'm now making estimated taxes on what i think an estimate of my estimated tax the whole thing is wait a second okay so i've already paid a hundred percent of what i paid last year in taxes so technically then i could file an extension yes and because i've already paid 100 of last year i'd get i think it's 110 there's a safe harbor amount sure just check and check on that but yeah you pay a certain amount based on what you paid last year and then you can file an extension and if you owe more this year than you did last year you're not going to get penalized supposedly not not tax advice changes everything i'm going to do that talk to you yeah i mean that wouldn't that doesn't increase the risks of no okay no i mean i've been audited one time yeah oh that's a fun story what happened um it was actually the uh the small business department sent an auditor to my house um because apparently some 1099 miscellaneous for like a hundred dollars like for some random little thing uh they filed it twice and so i was missing a hundred dollars but they basically needed every bank account statement every inflow outflow you can imagine that my finances are a little bit complicated and this this poor woman had to sit in my dining room for three days poor woman i had to sit in my dining room handing her every document she wanted for three days and um it ended up like there was just all kinds of complications with things that i had depreciated incorrectly and just it was just a mess wow did it work out in the end i bet if they were to audit like anyone who makes over a million dollars a year there's going to be something going on that they can just nitpick at absolutely no way you can keep track a lot of us yeah a lot of it is open to interpretation so then it's you arguing your interpretation of the tax code which is not exactly clear you would you would think yeah actually they the irs was pretty nice about it yes they show up with a giant binder anytime you have a question and then they give you a copy of the thing that they are basing what their finding was based on and then you have and i'll a right to then question that and take it to court if you want i just settled and paid them because again i'd rather pay a little bit more than have to deal with the mental anguish of yeah so i've heard like both horror stories from audits but i've also heard that anybody who's like complying with the irs they're really polite i've never heard a story be like hey they're so rude to me you're missed but it seems like i it if you if you're working with them they're nice it's just yeah i've always tried to be as as like on point as i can because i just i don't want to have to go through it so i've always just tried to like what do you call it cross your t's and dot your eyes and be like precise and everything yeah and you try but i mean you have an auditor looking at your everything you've ever done in the in the year and then they then they opened up the previous year it was just a whole ordeal and they're going to find things that they would have classified differently and some things they found that were in my favor so it's like well we found this it's going to cost you this much more but we also found this that's going to cost you this much less so they kind of so are they basically just going and doing your taxes for you that's what i asked her i said if i didn't want to file my taxes would you come audit me and just do this for me because you're clearly way more qualified than me because i don't know what i'm doing and clearly the cpa i had doing my taxes didn't know what they were doing if you're finding these discrepancies why did why are we going through this process how about you just tell me how much i owe you and i'll just write you a check right i mean that seems like it would be a way easier system right i agree with that that's always been an issue with mine with the irs it's like it's so weird how you have to come up with how much you owe them but of course there's always going to be some error that you could possibly make and then they're just going to go do exactly what you just did but correctly yeah and they supposedly know how much you owe why not just tell us you you're doing the math to figure it out like when you're auditing you know oh this this one's off because we had all these inputs and we are expecting yeah it really shouldn't be that hard i would love what do you think of a flat tax i would love it yeah yeah i would love just how about this how about we just call it a flat 30 that's it everyone pays 30 if you if you make a dollar or you make 100 million dollars thirty percent it would simplify everything yeah same for corporations and it wouldn't have to be thirty percent if you're taxing everyone at that rate and there's no loopholes there's no right if there's no deductions if there's no ways for the the uber rich to like do a fast one and end up paying two percent no everyone pays 30 percent on their income for the year but would it be net but you it couldn't be gross but it's not going to be 30 it would end up being like 8 once you once you factor in that you're basing it on everyone's income like the gross national product of humans and uh like so do you think like think of corporate so you think we would collect more tax revenue doing like a 30 flat tax across the board to collect the same amount and each individual person would have a way lower rate because you're also doing it for individuals corporations uber rich i would love that if you do if you say it like that though do you mean that also eliminates like property tax sales tax hotel tax like oh no it goes to different places like you still need to pay for your local schools and hospitals with your property tax and you just i don't know what california does with all the money they take from you but not anymore i mean yeah how texas doesn't have that and california does but we have bigger property taxes it's just you're gonna have to pay for roads and bridges and hospitals and all of that and i get it pay your fair share make sense you're a bigger house you pay more but um i think there would be a way to simplify everything i would love that i think just a thirty percent we could we could come up with what it is here and then just implement that we should love that yeah i wonder where parking tickets go because i've paid like 350 bucks in parking tickets and that's like three months it goes for maintenance on the scanners that they use to give you a parking ticket that's it i'm sure i'm sure it's not even i don't think they make money from parking tickets it would be impossible money from parking tickets i swear there's no way i have paid so much money in parking tickets in the past five months the thing is they have street sweepers that come through la and i bet that those street sweepers they actually make money on that because they give off they give off parking tickets if you park in the street and every single time i walk up and down the street on like the weird thursday first thursday of the month and like that day they have weirdest parking rules five to ten cars every street have parking tickets and each parking ticket is seventy three dollars it is okay well i can make they make money i guess if the if if the person driving let's say gets 120 a day they're probably collecting a thousand dollars worth of tickets maybe that it's gonna be there's nothing on the street the street sweeping machine has to be maintained the equipment the mailing the thing to you the then court costs if you fight it and the whole thing it it probably is i would admit that they make a lot of money i was trying to look into like the financial statements of of santa monica you should start a youtube channel that like that diet investigation i literally was like trying to find the financial states like where is all this income coming from like what are their expenses like because i was just wondering what is their parking ticket income yeah right and how much of a percentage am i of their parking ticket i went down that rabbit hole looking for where does the toll road money go and is it actually all being used to pay for these roads that when they first started making toll roads back in the 60s or something the whole premise was you're going to have a nickel toll to be able to build this road and then we'll take away the toll but they never did they just keep raising the rate so what happens to that money i couldn't find it the santa monica sales tax is terrible it's over ten percent sales tax ten percent yeah it's nuts las vegas i think is 7.2 what was the best investment you've ever made the best return you've ever gotten and what is the worst return the the most money you've lost these are these are you have to give me like time to research that i would say probably tesla is the best return but i still haven't sold it so i don't know so what's your unrealized gain um like two million dollars but what percentage is that um i don't know 200 percent okay something like that ish these are the questions that a lot of the i'm trying to check this thumbnail yeah i think i got like 1300 it was like 1200 on tesla i i could look it up yeah i don't know that's pretty good like a thousand percent on yeah maybe 400 i have no idea somewhere between 400 i still have some old old microsoft stock that i don't even remember buying that is probably like a 2 000 gain so that wow but that's something that you know i just bought a long time ago and never really looked at it again and it was never near the top of my account because i you know i sort by market value to see what i'm worried about for the day and there was nothing yeah that's the way to do it just buy something and forget about it if do you think you'd be better off today if you just held on to everything you've ever bought or do you think that you were better off selling and actively managing your portfolio that's a good question i think actively managing because had i just bought half those companies went out of business like i found i found that old login on yahoo that showed yeah this company doesn't exist anymore i don't i don't know what would happen to those shares um so yeah and i'm sure i've made terrible trades but in the end i've done better than having just set what's your investing style like are you a value investor are you like a social arbitrage investor social arm oh you are oh yeah absolutely that's very cool that's kind of what i figured out from scanning your videos so it's what it's all and that to me is like the one edge that you have over an investment banker they don't know what's going on you know in the real world where real people are shopping and seeing trends before they make it onto wall street so some of our big trades um that we've talked about on domani are things that are like trends that we spot before they you know caught wall street's attention do you think those investment bankers have like certain quotas that they have to like check off their lists like regarding net income like uh debt-to-income ratio long-term debts to like short-term income stuff like that do they do you think they have to do that so they can't do social arbitrage or do you think that they're just like not in that whole scene i think social arbitrage is probably too hard to explain to the people whose money they're investing so that it would be hard for them to run a fund that does that kind of you know on a whim we've decided to buy these kind of shares because we we thought we had some edge on the market that would just be harder to justify in your prospectus and so it's way easier to say we track the s p 500 we track the what's uh portnoy's buzz thing we track the uh social me mention frequency of what people were talking about 30 days ago so i mean they have a system that's easier to explain in a prospectus and that's that's how that's the reason i don't really invest in those funds other than i love the s p 500 just as a this is where i'm going to put cash that i don't that that's my bank account it's the s p 500 really yeah that's my investment i'm putting that in there being all right this is money i'm locking away and then i have a bank account i can't imagine dumping money into the s p and being like that's my bank account do you know what i did with my uh all my retirement accounts i put them in triple leveraged s p 500 because i figure long term yeah i mean that's a terrible investment i would never tell anyone to do that but that's what i did because this is money that i am not planning to ever need if i if i need my retirement savings something has gone wrong in my life and if i ever hit that point i'll i'll quickly re-uh re-structure what's going on in those accounts but to me it's that's like opportunity money that grows tax-free that if i want to be able to blow it out what better investment historically over the course of 10 20 years what would do better than the s p the only thing i can think i would be a triple lever why don't you just do that throughout your entire portfolio just 100 triple leveraged s p don't touch it i mean that is something that i've given a lot of thought to like would that beat me trying to individually choose things like tesla i wonder if it would why wouldn't you just go and put a million dollars in that and be like that's my fund gonna leave it i'm not gonna touch it i had a half million dollars in that um when the market started crashing and that made me really nervous because a triple leveraged bundle would that go down triple inverse 16. 60 yeah and and the rule of percentages once once it's gone down it takes twice as much to go back up and so that's why for a market crash situation being in a triple leveraged is you know it's it's death you can't you can't recover from it yeah and so that that was uh i was a little late to pull the rip cord on that and get out of it um but it's it has since recovered too yeah i remember i was looking at jason oppenheim's portfolio and he was invested in triple leveraged oil etfs and gosh i can't imagine how much money that's gone up now oh yeah i remember looking back at him like i can't believe you're buying this this is crazy he's like no we're fine i'll do fine oil's got to come back and sure enough i mean he's right but i was thinking like but no it's going to change the whole like people aren't going to travel as much but he's right i mean we're at a time where everything is just going up yes we're going to hit a point where it isn't like that anymore and i that's when i think it's going to be like a rude awakening for a lot of people who are new to investing where you can't just wait a week because it'll get better if i i don't see it happening anytime soon but that's what i'm worried about longer term like when is that point when is that and you're not going to notice it it's going to sneak up on you yeah so i was actually telling jack about this he's never heard of the lost decade yeah so now charlie munger was talking about over the next decade to expect lower returns we're not going to see what we have been over the next 10 years which i agree with him i could see a time where the s p 500 goes up goes down goes up goes down and trades within a range of i don't know 900 points and we're at the same point 10 years from now as we are today i don't think that would be impossible yeah i'd never heard of that um what would you do in that situation sell covered calls and you'd probably yeah you would make that's why you would manage you would manage a sideways market as you know try to make money going down and then appreciate going yeah it would sell puts ideally when it's at the lowest and then sell code calls ideally once it's not gonna be able to time it just right but you know hopefully you would be able to outperform zero which is what it could possibly do for 10 years so the goal would just be with time decay utilizing that to slowly just make the premium money and hopefully my stuff isn't called away from me and hopefully i'm not forced to buy anything by by selling the put yeah that's why i love options i mean that would work and then you're also buying the dips and you're buying it over time so it's gonna average out but yeah what would you do i don't know i hope to never see that situation but i i i feel like that would be so stressful that i would just want to just like not be in the stock market if it's just going sideways i'd be done you just pull everything out if you wanted to and just sit on your money i might do that i don't know just the the stress every day of having to worry oh it's a down day what's my strategy today oh it's an up day is that what you do now i no i try not to think about we we talk on dumb money live uh we we went weekly we went from doing one a week to doing one a day uh and that really had me probably making more trades than i should have and so i'm pulling back and we're only doing three shows a week now maybe two okay um just because you can't make a good trade every day it used to be in our whole social arb thesis you find one really good high conviction social arb trade a year and you might find two or three medium convictions a year you can't find one every week you can't find one every day and so it's it's like weeding through the discord communities finding all these amazing ideas and trying to weed through and find ones that you believe in that's that's kind of the challenge now it's there's so much information so many opportunities so many ideas that you can't invest in them all and you don't want to invest in them all but there's so many good ideas that you kind of want to so it just comes down to like having some discipline and waiting for things that are truly truly high conviction and then having a little bit of fun with small amounts in the things that are medium and low conviction what about bitcoin i think you just started investing in bitcoin didn't you um i've had bitcoin uh i was buying bitcoin at that all-time high back when was that thanksgiving when everyone was 2017. i was buying and then just watching watching it go down i was buying bitcoin i had um a binance account that had some crazy weird coins in it i don't know i basically now i'm all bitcoin and ethereum a 60 40 split i love bitcoin it's going to 100 000 i should probably move more money over into it i just can't mentally put my money in into it i i don't know sure i've been doing so far about five grand a week into bitcoin uh when it dropped the other week i think i may have done like 7 500 but just to balance everything out because i said i believe in it long term i do too yeah and so i feel like i have not had the discipline of taking money out of the stock market and putting it into bitcoin but i should it's so easy just i use coinbase and it's so simple to just transfer money it shows up instantly i think you gotta wait like two three days for it to withdraw the money it's so easy it just shows up like instantaneously you buy it instantly it's so much easier than stocks to have to do that the feast sucks i'm sure there's a cheaper way of doing it but it is what it is it is easy and i like that it's open on the weekends and afterwards like right now if you want to go and buy it i i think the stock market should be open 24 7. it it should i don't know why there's no reason no other than old-timey stock brokers didn't want to work yeah but it 24-7 be but it should be it should always be going up and down a market open somewhere yes around the world why not have our stocks also be available at all times i would love that's a good question i i don't know it could be just too stressful for people like i'm serious though imagine having like millions in the market like doing some like you know more gambling type investments i guess okay yeah it does give you the opportunity to sleep you know that's true i didn't think of that if just like after you know 1 pm here all right nothing's gonna happen till 6 30 in the morning yeah but does bitcoin keep you up at night like no a bit but it's not that bad right like no not no i mean if it dropped 50 i mean it just it is what it is what is your percentage of your net worth allocated to bitcoin two percent two percent i need to get to two percent that's my goal yeah i'm gonna do that uh when you're watching this dave later just go do that the funny thing is i invested one uh a little bit over one i think i had like total investors like 1.3 that's that's grown to two in two months i i could see at some point this ending up at a million dollars a coin at some point maybe like 50 years from now maybe it's it's i think it's either gonna be worthless or like a million bucks it's one or the other and that was my uh investment thesis in gamestop yeah either gonna be worthless or i'm going to quadruple my money so i'm i'm good with being in bitcoin for the long term yeah and i need to get more into it how about this give us some stock tips before we wrap up tell jack what to invest in i don't give stock tips i don't have what are you buying that jack can copy coinage terms or something like that like what's a a rule of thumb stuff like that stuff to live by as an investor yeah um i buy low sell high i i don't have like any it changes every day you just have to be listening looking finding opportunities looking for things that you that you think you know that wall street doesn't know that's that's what it's all about and finding like a correlation to it's uh cold in texas pipes are freezing generators are going to be in demand the electric power grid failed batteries and tesla and things like that um it's it's it's just making those kind of connections when you have something that you see that maybe other people haven't yet connected to a stock trade every time there's a hurricane the roofing companies go up that's now predictable but the first time there was a hurricane and the roofing companies all went up nobody had thought about that i respect your investing philosophy you know what you're good at and you stick to what you know like you don't have a big allocation in bitcoin you paid off your house although maybe it didn't make complete sense maybe you should diversify a little bit you know stocks and you continue to do stocks and you continue to do well so that's good it works how about this what stocks do you like i mean i'll tell you my biggest holdings for me and my risk tolerance it's tesla and amazon and apple those are my but are you buying more of tesla um i wish i had the conviction to keep buying tesla every time it goes down because you see that every time it goes down it does come back up but i just to for me to buy because i don't have any other income it means i have to sell something else and i really like everything that i'm in right now can you margin i could go deeper into margin i'm i'm i'm kind of at that threshold of there's so many good things that i want to be invested in right now that i'm i'm at the point where i've margined about as much as i'm comfortable with i'm at like maybe 20 30 margin right now and i don't like to go that much deeper probably i'm a little too conservative for what i for the returns that i would like but it's it's all a balancing act got it i don't want to be that guy but you could theoretically sell some puts on tesla if you wanted to pick a price that you were comfortable to buy it at and if it didn't hit that price you could get a little bit of income to then buy more tesla shares i i could do that and i've done that and i probably should have been doing that when instead of buying the dip i should have been shorting the puts on the dip i love the the income thing i gotta try that at some point any question you may have if i can't answer i would i got to enable it on schwab i i do that online or it's it's easy it's just like placing an order instead of buy to open you do sell to open it's it's a drop down right interest i really really want you to do options all right you know what i'll pull up my computer we'll we'll i'll do one now okay yeah let's do it well i mean technically it's you know not during market hours right but couldn't i just you can do a market order tomorrow but i don't know if that's something that you can't well can't we just do it now to opening the market open i'm not a huge fan of like you could put a limit order in it's very complicated but i i wouldn't do anything like aftermarket or anything like that i would realistically probably wait you can do a limit or it's not like you're gonna lose a ton of money but just to be what are you talking about like selling puts so if you sell it so if you sell a put you select a price and a date so say your your price that's called a strike price say your strike price for tesla what's tesla right now 7 15 or something like that seven i have no idea i don't really have any tesla so i'm not or what no no sorry i meant uh like uh doing the uh the covered calls you wanna do a cover call covered call is when you have the stock in your account and you're willing to sell it for a certain price let's try a certain date how do you do it on schwab do you do this yes which is under the strategy the options under strategy where your stock etf right now you have to apply yeah yeah you have to five to ten days for processing you could do it on robinhood instantly oh god you're gonna fall in love with it i promise you that graham it's awesome it's like it opens up all these doorways in investing it's like you can hedge your positions with options you can leverage your positions with options you can do so much more with options that you can't do when just buying common stock so like if i wanted to sell this at market right now it's 98.39 i could just hit sell and sell it for 98.39 or i can write a covered call for 98 and then i would be selling at 98 but then i would also be getting this 1.89 and so you're gonna get an extra four thousand dollars because you did this instead of just hitting the sell button and then that's someone say the stock goes up uh to you know 99 someone's going to buy that if they have the option to buy it at 98. if it goes down say it goes down to 97 they're not gonna buy it and now you have four thousand dollars that you just get to use to offset your loss because you have the shares at that and then you know they depreciate your best case scenarios it stays at 98 so you don't lose anything you get to keep the two dollars and that's kind of just like that's the best possible thing if it goes up you're losing out on it going above 98 but you're still getting that extra two dollars and it's cool because you don't have to pick 98 dollars you could pick 105 so that's out of the money that means it's above the you know selling a covered call above the market value so and obviously premiums would be lower because the chances of it hitting that are lower people are paying less to be able to buy it at that price yeah but but if you wanted to sell it at 105. yeah if you ever hit that then you would only be getting and this is not very volatile you'd only be getting an extra 19 cents yeah you get 366 dollars you have to pay commission to do this by the way oh you do it's all 13 they base it on the number of contracts but in this case you're only actually losing money if the stock goes above 105 dollars and what 19 cents because you have 19 cents per yes so if you if you wanted to sell this at 105 if it ever hit 105 you could get an extra 400 for placing the order this way but the downside is if it went to 110 you'd be like i just gave up five dollars in exchange for 19 cents you can do it every single week until this goes up to 105. but obviously if it's a slow creep you could just keep raising that up 106 107. wait and then continually just make money hedging against your own position of shares i might and experiment with that yeah build a robot that did that for you it would make it worthwhile i there's so there's some options that the option chain is just like has an imbalance and you can find like call writer like these secret underground chat rooms or people they're like oh this one's really out of whack and that is where you can actually make money if you have the time and you know for an extra 500 you can spend an hour doing that i use i did that for fun for a while and it was it just got to be too much you know too much mental overhead to deal with it depends on your strategy but you should definitely if you if you have like an extra hour per day to just go dig and try to find those imbalances in oh they're they're paying too much for these premiums and the uh the stock this is this is a stock that you can do what it's called like a buy right where you buy the stock and write the call in the same transaction and you're guaranteed to make money unless it goes to a certain threshold but there's enough premium built in so that you can get out before it hits that threshold there's so many strategies the thing is it's so complicated but so easy it's a whole spectrum it's a whole dark web that you don't want to go on it's great yeah i love it i want to try doing a few and we could do them together just maybe like i'll pick three stocks i'll sell them so out of the money and uh just collect the premium just try it a few times yeah see that's one way to do it you're probably not going to find it very worth your time the way that i love to do it is to pick a stock that's super volatile or say wall street bets is hyping up a stock like palantir or tesla or anything like that you know what they're doing they're buying as many calls as they can on that that's driving up demand thus driving up premiums so you can sell you know covered calls on your shares for these exorbitant premiums i mean you could get like 20 in a month on some of these stocks sometimes 20 that's that's unbelievable i don't recommend it i love it i recommend it but if you know what you're doing or if you're very conservative with it i've told jack it's like what is it picking up pennies in front of a steamroller that is exactly what it is no it's so safe down like that yeah but that's if you're writing naked call options that would be picking up pennies in front of a steamer holder i think so i don't know from my very limited understanding of this that's that's my analogy that i've seen online fair enough all right well is there anything else you want to throw in here um no do we want to talk about the uh dumb money thing yes so how do we just tell me go right in it yep so dumb money the original channel is about to hit a hundred thousand by the time this is on we will have hit a hundred thousand subscribers and we've decided to basically give the channel away to the next generation of creators we want to basically turn it into like a platform for people who don't have a big audience and so we're gonna take submissions and basically hire three people put them give give them a show on the dumb money channel and we're gonna not make content there we're gonna keep doing dumb money live and then make the new the old dumb money channel into something new how do you find these people well we're basically uh kind of auditioning so uh anyone can can make a video tell us about your show idea tell us you know if you have some great idea or if you if you've already done a show or you're currently you know on youtube send us a link and we are going to uh narrow it down and pick three and give them a show how are the three of them all gonna coordinate on one show it's not one show they each get their own show oh i see just so they each supposed to wrap ups and yeah think of it like uh you know nbc has a bunch of shows on it and or cnbc has like fast money and mad money and other kinds of money other kinds of money would be a good name so basically yeah it'll just be and and there'll be a reoccurring show they'll they'll do two episodes a week and you know that'll fill up like a whole are you worried though that the audience is like not gonna like one person but maybe they kind of like another and like the algorithm is all out of whack i think the algorithm is all out of whack on that channel anyway because we basically stopped making videos a year ago wouldn't it be discouraging to somebody who's like making better videos than the other two and then it's like well i just posted a banger but then like these other two knuckleheads they they ruined my algorithm so that by the time i post again like fewer people are watching it depends like if if youtube thinks about what you're looking for you know i the whole thing about the algorithm is they're trying to find what you want to watch right and if you have a playlist that has this type of video in one playlist and another type of video in another playlist doesn't that like i don't know i feel like kevin does live and recorded right and he's i mean people love him so yes that's why that works but i feel like you don't maybe get as penalized if you have organized your content i don't know i think you're you're the expert buzzfeed cut jubilee they all have that but they have a structure but they have different series like they have witnesses i don't know it will essentially be three different series on a single channel and each one will be its own title and its own like they'll be i don't know concrete did that they were they're a great channel and they had such good content but they were originally doing ben mallet videos and they were doing like other documentaries and stuff what ended up happening was that the ben malo was so successful and nobody cared about the other stuff and it hurt the channel to have like a really good ben mala video and then you'd have a documentary that in my opinion was an amazing documentary it just wasn't that audience and the audience that wanted ben did not want the documentary and it was discouraging i think uh for them to create this content because nobody wanted it they just wanted more ben well it's almost like if you think about i come from the startup world if you think about an incubator where it's basically putting money into a bunch of different projects and if one of them takes off that's great we want to launch the career of the next great youtuber it doesn't have to continue to live on money but if they can find an audience there they can they can grow from there that's fair so they can eventually go off and do their own thing whenever they want it's it's basically we're trying to we're trying to incentivize people to do this because we have fun doing it and we basically we're not good at making money doing it we just did it because we loved it but um if we can have people who are like really gung-ho about making these uh making content on youtube and we can give them the platform and we can give them you know production assistants and editors and and basically pay them a 60 000 a year salary to be able to quit their job if if that's like i wouldn't say anyone should just jump into youtube but if you've been wanting to do it but you just haven't been able to because you know you just can't afford to right this is this is that little push i feel like part of me it just just feels like uh if you're gonna do it on your own you would and there are so many weird learning curves that like if you were to throw me into a hundred thousand i would just drown because you're throwing me in a body of water that's just too deep for me to swim but starting out your own channel and like growing that and figuring out like how this works this doesn't work and learning by the time you hit a hundred thousand then you're like you're all prepared like you've been through it well maybe we can help mentor them along the way maybe you could help mentor them i i will help judge how's that that would be great i'll help judge yeah so we we basically have set up an email address you can uh send a link to a youtube video to get a show at dummoney.tv i'll put it in the description and uh they that's how we're basically taking submissions cool link down below in the description so cool anything else all right thanks so much for coming on everybody really yeah i mean we met right it was really nice to meet you and uh that was a great conversation i loved it we're all over the map on this one good luck editing guys let us know what you think of like this sort of style this is one of the few videos where we didn't go in with the structure and we just figured well we're just going to let it flow and have a conversation i'm sure some people like it some people don't but let us know what you think if you think we should continue more of just like the free flow conversations happy to do that if not we'll go back to a more structured approach it's fair i think it's fair call but regardless you should smash one of the buttons there's a thumb up or a thumb down just just a thumbs up button as far as we're concerned that other thumb button doesn't even exist just register the fact that you heard us say this by hitting the thumbs up yes and then leave a comment telling us what you think yes yes sounds great also don't forget to subscribe it's totally free to do and you get a brand new video from us every single sunday if you hit the notification bell you could be the first one to comment on the video and jack responds to like almost all of the comments especially in the first like hour or two so make sure you do that thank you guys so much for watching we have all of the links down below in the description you can get two free stocks too uh worth up to one thousand eight hundred and fifty dollars and uh that's it thank you anything else that's it cool thanks so much see you guys we'll see you next time if i did slow down on the main channel i would double down on the podcast really really what about the second channel uh there's only so much if you could react to the podcast i think is unique so we are in the 45th ever right i i have no idea we we have no idea they are completely unprepared for this yeah we've mismatched a few episodes like we filmed some way ahead of time that we're now posting so welcome to the 44th ever episode of the iced coffee hour my name is dave if you want to say dave from dumb money and so far the podcast is made three seventy nine how's this that's perfect yeah all right go for it your name is graham okay news