Memecoins? Portfolio Strategy & Cycle Analysis with OSF (Rekt Guy NFT Founder)

0:00I would never advise anyone to mimic my portfolio weights because I tend to be very risk on and pretty aggressive with stuff GM good morning welcome to milk Road radio the easiest path to get smarter about crypto I'm Jay Hamilton and I believe that onchain is the next online today we are joined by OSF the infamous Twitter the founder of wrecked guy nft collection former trafy Trader Barclay angel investor and a very successful crypto Trader and fellow podcaster and content producer in this spacee in today's episode we discuss osf's portfolio breakdown and his strategy for this bull cycle his bullish case for meme coins which led him to

0:49swap all of his soul into whiff this week where we're at in this cycle and how much longer he thinks it will be and his exit strategy which is is full of alpha so you're going to want to listen to the end to hear that without further Ado let's hear from OSF GM oie welcome to milroad radio hey man' thanks thanks a lot for having me can you give us a brief background on yourself and your entry into crypto yeah absolutely so I started my career in traditional Finance I worked as a Trader at an investment Bank traded high yield credit and distressed credit and I did that for

1:28about 10 years so I spent some time in London sometime in New York trading and towards the end of my career I guess I kind of discovered crypto like I'd known about crypto for a long time heard about it in 2013 tried to buy some eth in 2017 and I couldn't set up a coinbase wallet but I was always very crypto skeptic I think when you come from a traditional Finance background you're taught to appraise valuations methodically so whether it's through you know a model or fundamental analysis there are always different factors that end up feeding to what something should be valued at and then you have Bitcoin and crypto and all

2:05these valuations came out of nothing there was nothing to really like pin those valuations on so I was very crypto skeptic and bearish for a long on crypto for a long time just like I think most trfi people still are but then you had this whole inflation narrative start to pick up in in early 2021 and I kind of just got my head around Bitcoin being digital gold and I could understand its use case as an inflation trade and so yeah bought some Bitcoin in 21 and my friend and I at the time we were looking at buying Collectibles art watches and that kind of stuff because those are

2:38also assets that perform very well in inflationary environments and that's when we came across digital art nfts and we like oh wow this could be like the ultimate inflation trade because you have the Bitcoin crypto angle to it and then you have the collectible angle to it and we just felt like it was the kind of asset that could really take off and so I got deep into nfts and in you know around February March 2021 and after that I just kind of fell in love with the market like having traded traditional Finance for a while it was a much more exciting thing to trade because it was way more

3:11volatile massive price moves the the nency was very exciting you know no one really knew where things should trade or what the valuation should be and everyone was kind of new to the game so just found the nency of it very exciting where no one really knew what they were doing and there was a lot of opportunity I think to to get and trade it so yeah by the end of that year I ended up quitting my job to go full-time into crypto and nfts and we really started out really just collecting and trading stuff but I also used to make a lot of digital art when I was younger so I

3:43tried my hand at drawing a few things towards the end of that year and I kind of just took off as well and yeah since then we've just gotten really stuck into the whole crypto world and everything from Trading to running a couple of own projects to Angel Investing and stuff we've really been involved and it's been super exciting I definitely wouldn't wouldn't change anything so I'm can give a little bit more color to here you have you the founder of wrecked guy which is one of the most well-known nft collections if anybody out there I'm sure if you whether not you hold the W guy I'm sure you've seen it it's it's

4:14great art it's dope art kind of very much x copy like Vibes to it you also are are building out the whole wrecked brand which I think everybody in crypto loves the term wrecked although we're all trying not to get wrecked but we all probably recognize we we will in many anyways that's part of being here mostly today we're going to talk about markets and what your thoughts are just before we do can you maybe just give us an overview of your portfolio now and where you're at just so we can kind of frame our reference there's so many tokens in the space and so many people who are

4:47more invested in fungible versus more invested in nfts just curious what's your current portfolio sort of overview look like yeah that's a really good question now I would never advise any one to mimic my portfolio weights because I tend to be very like Risk on and pretty aggressive with stuff and my style of portfolio Management in crypto but also trading back when I was at the bank has always been to take large positions large concentrated bets in a few tickers rather than diversification and my belief is diversification is great but then you might as well just buy the S&P 500 or just buy a crypto index you're not

5:28really like getting any alha right it's just beta if you if you have something Diversified and to really get the alpha and outperform you have to try and pick a few winners and so it's a it's certainly a riskier strategy and in something like crypto where everything can go up quite a lot it may just be easy to hold Bitcoin because you're getting you know still phenomenal Returns versus traditional financial markets but the fun of it is trying to pick the winners and you know try and get big in them so as it stands I would say more than half of my portfolio is in meme coins now that's not because I

5:59think that's the way you should be structured it's because I bought a lot of mem coins towards the end of last year and early this year and because of how much they've moved they've now become a large part of my portfolio and I'm just trying to manage that lower and get it back to to a normal level but at the moment that's what it is and really it's across it's actually across three or four meme coins one of them is with Dog of hat one of them is MOG which is a meme coin on eth and then there's a couple other smaller ones that I have

6:29Epic Duck on salana and hack Moon which is on on blast on eth and then the rest of my portfolio is just Ethan Soul so really I just have my eth Sol barbell and then a bunch of mem coins in the middle and that's pretty much it and in the last cycle would it have been what would it just curious would it have been I'm guessing the meme coins would have been replaced by nfts was it mostly nfts in the last cycle and then eth and Bitcoin maybe because you weren't in Soul yet it was I've never actually owned a lot of Bitcoin so it was

7:01predominantly eth it was eth and nfts and I found that to be a good balance and you know this year you have soul which is in the mix now as well so yeah I like the idea of Ethan soul but yeah similar kind of idea like nfts rep replaced by meme coins as the higher risk higher reward parts of the market okay I wasn't going to ask this question till later in the show but since we're you now establish that 50% of your portfolio is in meme coins and you posted earlier this week on Twitter that you sold all of your soul for whiff is that true it's true yeah so I did tell a

7:36little bit of a lie earlier when actually the other 50% is just eth now not not Ethan Soul previously was Ethan soul but yeah I've owned whiff for a long time I was quite lucky to get early to it like I bought it in December wow and that was the first thing I really did meaningfully in salana I'd missed the whole salana train last year and not for not for lack of understanding it or wanting to take the risk I just I think I picked the wrong things at that time and didn't really appreciate how much of a narrative it could really become so salana was taking off and bonk on salana

8:09started taking off and I was like well you know if this thing's really going to take off surely there's room for another another coin and I just picked whiff really because it seemed to be the one that I liked the most and that was the funniest that had the most behind it and I never really expected it to get to where it is now I was like you know maybe this coin could go up two or 3x whatever I think it was like a $25 million market cap at the time um God yeah I know it's insane what is it three four billion now four billion now yeah

8:35it's four billion crazy right absolutely crazy I was pretty lucky because my style is always to like just go big into something and this is not to say I'm a genius like I've lost so much money going big into like random meme coins and nfts and stuff and they just go to zero right so but when you get one right obviously it can go pretty big but you know if like I had I kind of had moments of time where like I sold my whole position then I bought the whole thing back again I was really not sure what to do because I was so scarred from round

9:02tripping stuff in the bare Market that I wanted to take profits and not you know have something to show for it but at the same time I just felt like it was going higher and I think you know after a few weeks it just became clear that you know this is the chosen one and so I kind of had a couple of days where I sold the whole thing bought it back in like the same day and the next day it was up 50% or 100% I was like man if I didn't buy it back I would be hating myself right now honestly it feels like I've cheated

9:28death there but to to an extent but it be you know it became clear it became it was kind of like the chosen one and so I just held most of the position you know I rode a lot of it up and then once it hit a billion dollars plus and got a few exchange listings I took off about 75% of the position and then I kept the rest of it as like a a moon bag as we call it so I had that position for a while and you know then I you know notic like whiff sold off quite a lot in in in the

9:53last couple of weeks and salana felt weak and on the other hand you had Pepe and other coins doing pretty well and so I just felt like you know I'm bullish on memes and I think it's the casino of this cycle I don't think we've seen the end of it yet and on that basis I just felt like there would be another move higher for whiff whether it would have been today or tomorrow or next week or in a month I wasn't really sure but I just felt like there was going to be another big move higher for whiff because I just didn't see the mem coin

10:22cycle dying so yeah just put all my soul back into whiff and so far it's been a good trade you know we'll see how it pans out but you know something like that where it's like you know it's not necessarily that I'm bullish specifically on with although I am but it's just I just think meme coins are going to have another run and you they've shown signs of it and it felt like to me I could have more exposure to it crypto will go up more than 100x in both users and value over the next decade if you're listening to this right now you're extremely early and have an

10:50incredible opportunity to capitalize at milk Road our mission is to make you smarter about crypto that's why we're doing today's podcast and why we send you a daily newsletter from free but if you're ready to level up as an investor then let me tell you about milk Road Pro we crafted this resource for investors who are already smart enough about crypto and are looking for more actionable insights on how to invest successfully in one of the fastest growing Industries on Earth every week we break down the latest trends dive into tokenomics of popular and upand cominging tokens and get into the nitty-gritty of market analysis all to

11:21help you invest smarter plus we have a private Discord Community for pro members it's like your backstage pass to the milk road crew exclusive insights Hot Tips and live amas with our team now if you're looking to level up as an investor then click the link in the show notes below and sign up to Pro today don't let this bull market opportunity slip through your fingers just going to comment on sort of double click on your point earlier of not everybody should follow your strategy here and the main reason is you're quite active and most people are not capable of being that active for a few reasons one mentally it

11:57is so draining and stressful exhausting as you said like buying and selling your whole bag in and out like that like most people can't handle that and that's okay if you're listening and you can't that's okay and also you need to you unless you're like us and you're full-time in this space which most people are not yet right I hope over the next decade we will get to the point where yeah billions of people will be working on chain but we're not there yet and so if you're not act that active then it's really hard to keep up on all this stuff and to make these quick decisions okay I

12:31want to go back to your two two questions and these kind of go together is I want to understand a little bit more about why you're bullish on mem coins although it might be as simple as I I think it is and then I want to understand your statement of you don't think this cycle is over so let's zoom out where do you think we are at in this cycle yeah so why am I bu on Meme coins something that's really struggled this year and people have that people have become wise too is this idea of VC coins right so you know many of these tokens

13:02and Technologies and whether they're l1s l2s gaming tokens whatever they are the these guys will raise money from VCS at very low valuations they'll then come to Market at multiples of the valuations that which they raised that and they have a very low circulating Supply versus their fully diluted valuation and for the first couple of months whatever it is 3 months 6 months it's usually a six Monon Cliff it's all fine fine it trades okay but you know after 6 months these VC tokens start to unlock right and these guys are up 50x 100x on their initial Investments so they're just selling and that's why you see some of

13:41these coins with just you know what feels like Perpetual sell pressure because something might go down 50% post post the VC unlock and then it might drop down another 50% over the next two weeks and the average retail investor might be like you know what's going on why is this just keep going lower and lower but if VC is up 100x and then it drops 50% they're still up 50x right so they're just going to keep selling and even if it drops another 50% they s 25 they still they have they're so far in the in in the green in the profit that they will just continue to sell until they're

14:14out of their position they taking out all the proes they can take then move on to the next one so I think a lot of those coins are are technically challenged and very doomed really from the outset and a lot of retail investors don't understand this and this is the thing you know you speak up meme coins and people like well that's just a joke it's not real technology it's not real crypto look at this you know amazing Tech that this L2 has done which is fine because you know from a fundamental standpoint you may have a point there but trading and investing is not all

14:44about fundamentals you have to also have an appreciation for the technicals and you can have the best coin in the world but if someone owns a large chunk of the supply and they're up 100x they're going to be selling and they will keep selling until they're out and it's difficult for you as a retail investor to fight that so mcoins don't really have that Dynamic right because most of them are fair launches and yes at the beginning maybe some people snipe the supply and you get some whales at the beginning but you know eventually that Supply ticks over and they're out there's never more coins to vest and people generally aren't up

15:16100x straight away on the me coins that happens over time so from a technical standpoint the supply management and the tokenomics of a meme coins are actually a lot better than VC coins and that's not the case for every single meme coin some you know like in anything you have Bad actors and that can happen on mem coins but you know for the most part the coins that do well have much more stronger much stronger tokenomics than the VC coins and then the other thing is you don't they're not predicated on someone going out there to complete a road map you're not predicated on this L2 launching this main net on this date

15:50making sure there's no bugs in it making sure they get this much tvl and compare this tvl to that tvl there's nothing like that it's just is it a good meme is it funny and will people congregate it around it as a community if so that it can do really well and there's no real limit to how well it can do because there's no comparables I mean we're comparing to what like Doge in 2021 which got to 100 billion $80 billion market cap there's no cash flows or anything to to pull a value from it's like I mean Bitcoin is the original meme coin I'm just describing all the

16:19characteristics of Bitcoin so from all those standpoint and for getting all of that they're just fun it's a lot of fun to trade them it's fun to find things that are funny and get involved and the telegram chats and the WhatsApp groups and you know the discords they're all hilarious and I think people have fun doing it and it caters more to younger audience which are probably the larger users of crypto right now so they have a lot going for them and I just think the number one attraction of crypto is to make money which is a derivative of derives from gambling to a to an extent

16:51and that's kind of what mean coins are it's kind of like a little Casino It's the main crypto casino right now so yeah I just think all those things mean that they will do well and generally speaking when sector does well it doesn't mean you can have tons of meme coins which ones do you pick there's hundreds of thousands of them now but it does mean that you may have a select few that are at the top the three best the five best that can kind of lead the market and do well kind of like how we saw crypto punks and B8 lead nfts in 2021 and so

17:19that's basically what I think about memec coins that's not to say they will last forever and this will last forever because they it won't you know look at nfts right nfts were killing it in 2021 and was going up so much right and then people were like this is going to change the world and you know next thing you know two years later three years later you just nfts have have dropped like 90 99% across the board and we could see the same thing with me coins we could it's just about identifying When the tide turns but for now I think you want to be invested I don't want to say the

17:47word invest you want to be gambling if you're gambling you want to be gambling where the biggest and hottest casino is and right now that's mem coins okay so follow-up question I did not expect to talk so much about m coins on the episode but I love this what's where do you think we are at in the cycle and what is your exit plan yeah that's a really good question I've really been asking myself this a lot over the last few days and weeks and I think two or three weeks ago I probably would have said that we are closer to the end than the beginning so we're over halfway

18:20through the cycle I kind of felt maybe like 70% you know 70 80% we had some big moves I still felt like there'd be another one more big move and then maybe things would change but I think my views on that have changed in the last two weeks because we've had some major developments right we've had complete 180 in the US political arena for crypto right complete 180 you've had the eth ETF suddenly surprisingly get approved with no comment commentary from the SEC which you know was like a political Act of God basically someone was like hey you guys are approving this and now you have Donald Trump going out there saying

18:55he's going to save save all the bitcoiners from you know Warren and her goons and he's going to make the US a crypto Hub and all this kind of stuff to 50 million crypto holders in the US I mean that's complete 180 from him and crypto's a you know crypto is a massive thing right now it's I think I read somewhere that one in three people care about crypto when voting in in the US elections like it's a big topic right now and so you know I think Trump is probably heading the polls and so for Biden and the Democrats to you know to counteract this they kind of also kind

19:27of have to be on board too and you did see some signs of that you know they did say they weren't going to veto The fit21 Proposal that went through a couple of weeks ago so that for me is a massive thing because number one you have an eth ETF approved which we didn't think was going to happen which is huge it basically says e is a commodity not security and it paves the way for that same logic to apply to many other alt coins which were all were all at risk of being classed as Securities by the SEC and number two you now have the US

19:55changing its stance on from trying to like destroy crypto actually supporting it and so I think those two things will give it another life and I think will make this cycle longer than I thought it would and therefore I think we're actually probably maybe only halfway through I think we have a lot more of it to come and yeah the last two weeks of developments really just changed my view it just I feel like we should be way higher for what's happened and maybe we need to muddle through and the market needs to digest the news a little bit more but yeah it was you know I think

20:23we're I think I would say we're halfway through now based on that and when you say halfway through do you mean in time or do you mean in growth of market cap yeah that's a good question you know I've never really thought about it from what am I answering for the halfway through in time or price I think probably both I think I think you know I think Bitcoin can get to May well actually I think no I would say time but not price I think prices can go higher I think Bitcoin could get to 250k I think ether get to like 10K so from a price

20:53standpoint that's you know maybe 30% 30% of the way through coins I think could move a lot higher time standpoint I think probably halfway I I think my guess is like maybe Trump wins the elections Market rallies crypto rallies goes really high then inflation starts spiking again because of whatever he's going to be doing and trying to push for lower rates and you know some at some point next year second half of next year things start to feel not as rosy anymore and that's when you know we start heading lower again so what's your exit plan it's tough to figure out the exit plan I think what you need to do

21:29whether you want to exit or not depends on two things well you have to decide why you want to exit something do you want to exit it because you're trying to time the top of the market or do you want to exit something because you have personal financial goals and you've made enough money and you want to take those chips off the table to to secure that and the two things are not necessarily the same right like for example if I'm like I want to make enough money money to quit my day job and if I've now made that money I should be taking that off

21:53the table to achieve that goal because man if things fell from now and I missed that goal I be really bummed about that so but if my goal is I want to just time the top then you know you have to try and do that so for me like personally like I think I think I've returns wise I think I've gotten pretty lucky on some things I've done well so I'm at a point now where I've taken some chips off the table twice this year meaningfully and starting to trim some positions again now like I think as things go higher just take a little bit off I think

22:20there's no need to try and sometimes you feel like you just going to sell the whole thing and that's a mistake I think the idea is you know prices move up 10 % 20% 30% 50% take a little bit off same again take a little bit off and just chip away at it that way I think I still have some skill in the game if things go a lot higher and and I'm you know I've underestimated it and if things go lower then I've you know take some cash some stuff out but for me I'm definitely not in like adding risk mode and I'm definitely in like selling on strength

22:50mode I would say but in very small amounts to try and last myself you know a Year's worth of selling or something like that basically and when you take chips off the table what do you do with that do you just hold it in cash for me the definition of taking chips off the table is very I have is very strict I assign myself very strict definitions because you never know what can happen in crypto right so for me taking chips to the table is actually selling it for Stables sending it to gemini or coinbase or Kraken or whatever and converting it into Fiat oh wow

23:25really do take it out okay yeah with the cash in my bank account with the amount for taxes set aside in another bank account right because that's the only way you can really truly be risk-free because still holding money in Stables what happens if you get hacked one day or you know your account gets compromised or whatever or you know usdc lost its Peg last year right so like it wasn't trading at one it was trading at like 90 Cent so there's always risks there and yeah of course people will say there's risk to Banks bank accounts and stuff but I mean look at the end of the

23:55day you can pay your bills in with Fiat right you can't pay your bills with with crypto at least not yet so taking chips to the table means that and I think I will continue to do that and then maybe after I get certain point I'll have some Stables because you want some easy liquidity to have to you know buy crashes and big dips and whatnot but I'm very very prudent about managing my risk managing my tax because I think I've seen people firsthand screw this up and make a ton of money on paper but then have nothing to show for it at the end of the day because they've messed up one

24:28of steps and I think at the end of the day if you're here making money trying to make a difference to your life you need that money in your bank at some stage right and so I'm very cognizant of doing that it's fantastic advice this is you are a true crypto ggen but also an incredibly conservative thoughtful person this is a a rare combination in the space especially for somebody who's the founder of the wrecked guy brand having not met you before I imagined you imagined you to be much more DJ as you appear on Twitter to be honest it's wonderful to hear this balance you're

25:02much much more wise in your old I guess you came from the trafi world so you got yeah Obie thanks so much for joining the show today thanks for sharing your wisdom with us we will throw a link to your Twitter uh to your nft collection to all the things we discussed in the show notes for anybody who wants to follow you highly recommend you guys follow OSF on Twitter because he's putting out the good stuff on the daily wish you all the best of luck in in your mcoin journey this cycle and thanks again for joining us thanks for having me in case you missed it in today's news

25:37PayPal has launched their stable coin py USD on Solana this is big news to see them moving their stable coin onto the salana chain they are already on the ethereum Chain I think they saw tether made 4.5 billion in net profit in q1 2024 meanwhile PayPal recorded a profit of just 888 million in q1 2024 no doubt the light bulbs are going off in the heads of the guys over at PayPal saying hey we got to jump further into this game also Black Rock Spot Bitcoin ETF has surpassed grayscales ibit has finally flipped gbtc ibit is now the largest spot Bitcoin ETF in the United States as of

26:32Wednesday morning over 20 billion worth of bitcoin whereas gptc holds about 19.7 billion also in news today a US judge has ordered the SEC to pay 1.8 million in Damages for overreach against crypto company debt box the best quote I saw here was that even when crypto wins we all still pay that's it for today today's episode of milk Road radio have yourself a wicked awesome day thank you for listening to milk Road radio the easiest path to get smarter about crypto if you like this episode share it and hit subscribe or follow so you don't miss out on the next one there's also a link in the description to our free 5

27:15minute daily newsletter where we simplify crypto for you while making you laugh and if you're willing to step up your crypto investing game then we'll leave a link to milk Road Pro as well your number one resource to help you invest successfully in crypto one final note this podcast is for educational purposes only nothing we say is financial advice crypto is risky so you should never invest more than you're willing to lose thank you friends and we'll see you in the next one