My Crypto Investing Principles in 2024 – What I’ve Learned and Changed in 7+ years

I’ve been actively investing in the crypto space now since 2017 and I’ve made some good moves and quite a few bad as well. Here are the investing principles that I’ve developed over the past few years that tend to work well for me.

I’d love to hear if any of these resonate with you or if you completely disagree.

Cobie’s advice: https://x.com/crypto_bobby/status/1485609015648399362?s=20

Follow me on Twitter: https://twitter.com/crypto_bobby

Listen to the audio version:
iTunes: https://podcasts.apple.com/us/podcast/the-psychology-of-crypto/id1721602290
Spotify: https://open.spotify.com/show/7tpl33Lit1CZrgeT4RSAJM?si=e87d98ba00c443e0

Looking for a job in blockchain? Get started with Proof of Talent, a blockchain and cryptocurrency focused recruiting firm – https://proofoftalent.co

** This is not financial advice and these are simply my own opinions, as such, this should not be treated as explicit financial, trading or otherwise investment advice. This is not explicit advice to buy these cryptos, do you own research.**

Hey everybody what’s going on it is Crypt Bobby and today I want to talk about my crypto investing principles and this is something that it is not like written on my wall as the Ten Commandments are written in a journal somewhere but looking back on the past few years that I’ve been in

This space these are some of the things that I’ve either generally stuck to and have worked well for me or alternatively I have learned along the way way through trial error mostly mistakes and so this is something that hey it might not work well for you or

Some of these points you might you know very much disagree with probably even the first one you might but figured I would share them because these are things that have helped me over time to become more successful investing in the space not blow up frankly do pretty well

Financially and so figured I would share them would love your thoughts too like if if you agree or disagree with any of these things it’d be super helpful to understand but these are generally the things that are I would consider kind of like my guiding principles in the crypto

Space so like I said in the intro I don’t necessarily have these like written down anywhere crazy this is just kind of my My overall thoughts as to what has worked well for me and I’ll explain why I think this way as well as why it might work for some other people

As well in the first point and I think this is especially prevalent when you look at some of the things that have happened recently for one if anybody’s keeping track of the crazy move on trb I’ll put a chart on the screen uh from yesterday on New Year’s Eve Happy New

Year’s everybody uh by the way if you’re watching this on January 1st or sometime soon thereafter but one of the things that personally for me just does not work well partly because I’m in the United States although they are decentralized alternatives but um one of the things that just does not work well

For me is is leverage and so I typically try to avoid leverage both long and short in crypto but I’ll talk about why I think that is but especially on the short side so I don’t trade on Leverage really at all like every once in a while

I’ve taken a tiny tiny percentage of my portfolio and I’ll punt it on something you know levered long and every single time that I’ve done that I’ve done that especially the past and this is something I’ve kind of learned from experience it causes me way more stress

It causes me way more just tension than it’s worth I could be up or down and I really I could be down significant amounts of money on a spot crypto bag but I’m totally fine with it I’m totally totally comfortable with it because at the end of the day the units are still

The same if you have 10 Bitcoin and Bitcoin drops 10% at the end of the day you still have 10 Bitcoin So eventually if that price moves back up which it likely will you’ll be fine however if you go into a 10 Bitcoin long and then you are the

Price drops 10% and now you have nine Bitcoin that for whatever reason just gives me so much stress and anxiety and it just doesn’t bode well for me so I personally avoid leverage in pretty much all these circumstances I’m not I’m not a good leverage Trader I’m

Not somebody who likes to go crazy with things and in the grand scheme of things the way and I’ll talk a little bit more about kind of like how I I structure generally like my my eye for investing in the crypto space but this is an

Industry where things move five 10 20 50 100 I’ve hit 200 X’s before do you really need leverage on an asset if you think that it can go 10 20 50x like that is a huge multiple in and of itself and those things that tend to go 50x

Potentially also have 50% 70% pullbacks even in Bull markets so if you do use leverage on those assets you can really hurt yourself in the long run and basically wipe yourself out so for me just holding spot bags is perfectly reasonable and fine and it’s just something that that works well for me

Now on the flip side on Leverage shorting I think shorting in crypto is stupid that’s that’s my personal opinion I’m sure some people can do it quite well obviously there are certain times in which shorting in the crypto space has worked out phenomenally well for some people however I think in an

Industry that is as volatile as this and again going to that trb example that can throw up on the chart whatever manipulation that was whatever whatever happened there I have no clue all I know is shorts got absolutely blown out and so for me what whatever the asset is it is simply

Not worth the the risk you know the risk reward of of shorting is just not worth it in any way shape or form I have no interest in touching it again for assets that can go up 50x you’re going to go and you’re going to you know put yourself in a huge risk

Financially to maybe capture 10 20 50% downside no return I don’t know that’s just for me it is not something I’m interested in doing I think for most people it is not the best move and I also think like one of the big things that I feel like we see very often is

People miss out on upside moves in crypto and they get mad and then they try to short it all the way up take soul for example recently salana mov from whatever it was 10 20 bucks all the way up to1 $120 people were shorting it that whole

Way up because they were just mad that they missed it in a lot of respect and they got blown out the entire way versus if they just either did nothing or alternatively if they bought it on the way up but for me again I think avoiding

Leverage in any way shape or form is really important because I think the the rewards of this industry are good enough if you are simply unlevered that it is not necessary and then to that point on Leverage I just think shorting is you know if you want to go lever long fine

Whatever still think you don’t need to do that but I just think the risk risk reward of shorting is horrific in the crypto industry the second principle that I somewhat follow I would say and this is not really intentional it’s just kind of how I’ve learned that my mind

Works best and that I am most comfortable and again like you might think that these are the dumbest things in the world this is just what works for me and this is kind of from my lens and my personal opinion and and just kind of like how I am most comfortable investing

In this space and that second principle is Big concentrated bet and this is something that I’ve learned over time too this is not something that like when I really started kind of quote unquote investing in the space in 2017 which is when I’ve I’ve actually put

More money into it I was not this way I probably had 10 plus you know if you guys used to watch the the YouTube channel and I would publish my portfolio like I would have five six seven 8 10 plus bags sometimes and that is not how

I like to structure things anymore I am very much more on like big concentrated bets and the reason for that is because I would rather Focus my energy and my attention on a few specific places versus spreading that out too thin I think that a there is a ton of uh

Advantage in this space if you really understand what’s happening on a specific coin or multiple multiple assets um you know it could be two three like whatever your attention fan is but I think if you are like really inep on something in particular it doesn’t

Matter what it is but if you’re inep on that it could be you know some type of coin it could be an nft like whatever it is if you understand the Catalyst if you understand all the developments if you’re in deep in Discord or just keeping track of things I think that

There is a lot of alpha there still at this point in time and so having those concentrated bets I think kind of gives you that um that strength and I think with that to when I say like big concentrated bets it’s about like high conviction for me if I am in 10 assets

If I’m in 10 cryptocurrencies it is very likely that I don’t have high conviction in all of them and for me I need conviction to be able to hold on the plus side and on the minus side of moves because they both happen all the time like for me one of

The best plays I ever had was was thorchain and Rune and I bought that initially at like 10 cents or so give or take and the the moves and the swings on that that that I was able to hold that through were pretty wild basically going

From 10 cents to a dollar to like 30 35 going back up to a dollar you know there were moves and then from a dollar basically straight to 20 bucks back down to $3 back up to $15 and I was able to hold through pretty much all of that because I had

Like a really strong degree in of conviction in what the project was doing the economics behind the coin and just like the the contacts that I had with people within that space and so I had a ton of conviction and so I was able to hold that big concentrated bet versus if

It was just like the ninth biggest coin that I held and I saw it going down 50% I didn’t really care about it but I had a friend maybe who told me about it and I just kind of bought a little bit I probably would have puked that bag the

First second that hit minus 50% cuz I just didn’t care as much about it and so for me I like to have these like bigger bets and that might be one two three probably three max where I’m just in it and I I know what’s happening and I know

Even if it goes down which it probably will because this is crypto even if it goes down for a bit I’m comfortable holding it because I have some type of thesis on it you know in the medium to long term and that tends to work well

For me I think another thing too of why I like like the big concentrated bets is because going to the the subject of the 50 the 100 X’s if you hit 100x that’s awesome but if you put $100 into it that’s probably not going to change your

Life if you put a I I don’t know what a you know a large or big bet is for you but if you put a substantial bet on that 100x hey that might be a $10,000 bet that then turns into a million dollar that’s pretty pretty damn lifechanging

For basically everybody in the world and so whether $110,000 is a big bet for you or not um I think like sizing appropriately and sizing big for specific opportunities like I would rather I would rather size and go in kind of with with strength into these bets versus just peppering around a

Bunch of little small bets because if one of them does really really outperform that’s awesome but on the flip side like am I going to take full advantage of it and that’s something that I want to try and do and just kind of have that conviction in doing so this

Is something that we’re probably talking about a little bit less right now as things seem pretty damn positive I myself am I would say very positive going to 2024 I think most people are um which somewhat is a little bit scary but hey that’s for another day

However one thing I think is is really really important in the crypto spaces is simply to survive and that could be on the run up that could be on the run down whatever it is I think you just need to stay in the game and I’ll talk a little

Bit more about that kind of Posta but I think staying in the game is wildly important because if you blow up if you go bust if you go to zero if you go to negative whatever it might be if you do not survive you are not going to be able

To take advantage of the 1050 100 X’s that are available in this space so I think like for me that’s that’s a huge thing to try and do on a consistent basis is to put yourself in a position to survive and so that could be from a hardware wallet security perspective

That could be from an exchange perspective like whatever whatever that might mean for you I think is just something like always we’ve seen all the blowups we’ve seen FTX and we’ve seen all this type of crazy things happen you’ve seen three arrows and and like all of the the industry kind of turmoil

That’s happened same thing happened in 2017 or post 2017 2018 2019 for a lot of different companies and individuals and and so I think that you know while things are looking good this might be a little bit less prevalent however it’s still the mindset that that I try to

Have going into things and I think that is important to try to do and to that point and again this is like maybe a little bit less prevalent right now because I think people are are very much paying attention and are very much interested the same could not be for

2023 for I think a lot of people um however this is something that I think is is probably like the most important thing in crypto and it is to really never lose interest and to to always pay attention and it’s a lesson that I learned the hard way frankly in between

2013 and 2017 and there is a a video clip that I’ll I’ll try and link to I I think I have it somewhere I can put it in here but Kobe who I’m sure everybody knows uh said on the all in podcast he really like summed it up perfectly because he’s

Much more eloquent than I am and he talked about staying in the game staying interested and my kind of learning from this was in 2013 like December 2013 I started mining Dogecoin within the first like two weeks of it being in existence I had basically zero

Disposable income I was still I think a year out of college I was making like practically zero money after rent in Washington DC uh so I didn’t really have much money to be investing in the space I also again didn’t have a ton of like real real

Conviction and I was messing around with Dogecoin with a little bit of Bitcoin and I did that for about three months I had fun I was mining it I was uh you mining Bitcoin on like the little USB Asic miners when they first came out that were pretty fun to mess around with

It was like 01 Bitcoin a day which didn’t seem like anything at the time but now is is frankly a pretty good amount of money and I lost interest pretty quickly uh after a few months and I had a friend that kind of got me back into the space in

Like early to to Mid 2017 however I missed that 2014 that mid 2014 really to 2017 window and if I was involved in that there was a ton of wealth generation that happened in that space if you invested in the ethereum Ico if you did anything along those

Lines you are now wildly wildly wealthy and I thought to myself and I basically I didn’t get like super mad at myself but I lost interest and that was 100% my fault and so when I got back in in 2017 I started making the Crypt Bobby videos

In August of 2017 uh just to kind of like air my thoughts and things like that I said to myself you know no matter what happens I’m not doing that again I’m not losing out on those opportunities again and basically the exact same thing happened in 2017 there

Was a crazy sick runup it was super super insane um and then 2018 happened and crypto basically nuked and went sideways for two years until 2020 and I stayed in and I stayed interested and because I stayed interested as well as I was employed at that point in time

I worked at air swap so I was of in the defi ecosystem really really early on because of that I found something like run at 10 cents that’s now at know five six bucks went all the way up to 20 bucks I found all these different def

Projects that I was able to invest in and frankly like that changed my life and and kind of my trajectory and things which has been pretty awesome and so that’s has has shaped me very much and so even post FTX blowup post uh three arrows all the negative things that have

Happened in this space I have kind of vowed every day basically to never lose interest and to always pay attention because is you never know when those big opportunities are going to arise and a lot of times the best opportunities frankly are during the bare markets you think about

All the things that happen and when you’re in a bull market and something’s up 100x you’re like oh man if I had only invested in that when it was 10 cents and now it’s a bajillion dollars or whatever it is like if you pay attention you have those opportunities you can

Dollar cost average you don’t have to do anything crazy but those opportunities are really there for you if you don’t lose interest and I think that is such a kind of guiding principle for me and I I learned it frankly the hard way because I probably missed out on like

Generational wealth from not investing from 2014 to 2017 so investing in what you know in the crypto space I think is important and I’ll caveat this by saying I think nobody knows Jack most of the time in their crypto space some people know a lot more than others obviously

There’s some giga brains online that are basically Geniuses I myself am not one of those people whoever I would say I know more than some in certain areas and because of that I choose to invest in those areas and sometimes that pays off really well and sometimes it hasn’t like

Right now I still really like defi that is the area that that I know that is the area that I am most interested in I find just like the most fascinating to me I’m not great with layer ones I’m not great with nfts I’ll like punt a little bit

Here or there maybe in some of them but like it’s just not it’s not what I really know I’m not a incredible technologist that can understand some of the you know nuances between salana and then ethereum and then Celestia and Ian layer and all those types of things like

I I can maybe understand it at a super high level but it’s not like what I know at the core and so for me I try to stay true to like the things that I either either know a little bit about or um actually like keep track of it and study

And I think that that is for me a really good way to approach things because the crypto space is challenging enough in and of itself and so trying to put your money in areas where you feel like maybe you have a a specific Edge and for me I

Think that like that is defi to me that’s like the area that I’ve worked in professionally that I have spent the most time studying whether it is just you materials Discord coins you know everything around that like that’s that’s what is most interesting to me

And so that is where I choose to to do things and that might be very different for you like some people are are just sick with meme coins I’m terrible I I I always mess up meme coins some people are are great sniping new launches or

Are really good with nfts and kind of understanding the culture around nfts and like what’s going to do well some people are you know just want to invest in Bitcoin dollar cost average or ethereum or you know whatever it is I think trying to figure out what you know

Best and what you’re most comfortable with is a is a good thing and for me that’s that’s one of the principles that I try to follow for the most part although if I’m being honest with myself and honest with you there are many times that I can stray from that because I

Have a friend that’s like hey this is the the hot new thing and so I might put a little bit of money into it and just have no idea what’s happening and so it is I’m not always perfect with this I’ll I’ll say that sometimes there’ll be some

Hot new thing and I’ll be okay maybe this like trend is cool and and somebody else is talking about it and I’ll try and do it and then I’ll probably inevitably lose money because I just don’t have the conviction in it or don’t know anything about it and you know

Every time you learn something but that’s that’s just kind of the game here so the last principle and this is something that I’ve learned a little bit to seen from experience is when you cash out cash out and what I mean by that is if let’s say we are all in a fortunate

Position or you are in a fortunate position in 20124 where the coins go up a lot and you have an opportunity to take some profit and you might be sitting there also thinking to yourself I am just going to be you know long Bitcoin or long ethereum forever and

That’s that’s great you know it’s great cuz you don’t have to pay taxes if you never sell so so more power to you but on the flip side if you are somebody that makes life-changing money and you want to cash out when you cash out cash

Out and when I say that I’m talking about like keeping money in the crypto ecosystem and this is something that I think a lot of people unfortunately learned the hard way in 2022 2021 but there were countless people that made a ton of money in the last cycle and

They’re like like all right made a ton of money made millions of dollars I’m going to just I’m going to go into a safe crypto investment I’m going to put my money into us and I’m going to sit it and anchor and I’m going to make 20% so yes I just

Made 100x on this coin I made you know a million dollars I made 10 million bucks I’m going to just throw it all in us and I’m going to make 20% a year and that’s going to be sick or I’m going to put it

In FTX because FTX pays 7% or 6% on us on us D or usdc or usdt and I’m going to make a little bit of interest there or maybe I’m going to LP like a usdc or usdt pool on some random ass like third uh Unis swap uh competitor on a L2

Somewhere instead of doing that you’ve already made the 100x you’ve already made the 50x the marginal benefit of making that extra 6% or that 20% or whatever it might be is probably not worth it take the money put it in a bank account put it in a

Savings account put it in treasuries put it in wherever but probably don’t leave it like within the crypto ecosystem and it’s going to be tempting and I’m probably going to be tempted by this too because you think about the opportunity cost and how much money you can make in

A you know in some random interest earning Thing versus what you can make in a treasury bill or in a savings account but the risk of potentially blowing up in maybe maybe Terror was something that a lot of people are talking about blowing up but in in fact

Like there were a ton of people that were super bullish on it and had a ton of money in it but then even FTX like FTX Genesis blockfi all these places were deemed to be in a lot of cases like very safe like I think most people were pretty comfortable keeping millions of

Dollars of usdc or US Dollars whatever it is earn earning a percentage yield in those places after that they made money and so if you are so lucky as to make a ton of money in crypto been there and have seen this happen and have experienced it if you do get the

Opportunity to make a lot of money when you cash out move it to a place that is outside of the crypto ecosystem you can always take that money and move it back in and that’s something that for me I kind of had to understand and get

Comfortable with like I love crypto I I don’t like being I am much more uncomfortable being under exposed to crypto than I am being Overexposed to crypto so in the last cycle I was like I don’t want to cash out I don’t want to move anything here like what what about

The upside what about if I cash it out then I’m never going to be able to get back in if you take money out you can eventually put it back in quickly slowly whatever it is there’s going to be opportunities to do so so just kind of

Move that that flight to safety versus putting it in something risky within the space for extra yield so that you can actually survive and so these are Again The Guiding principles for me I don’t I’m not perfect at following them this is something that I kind of sat down the

Other day and was thinking about this video like what do I do what do I actually follow what do I believe in in this space that’s going of helped me to be successful um or alternatively that I’ve had to learn the hard way that I’ve been very unsuccessful and it’s doing

This kind of new principle for me is has helped to improve my abilities within the space and I hope this was helpful for you if again like if you agree or disagree strongly with any of these I would love to hear from you you know in the YouTube comments or on Twitter from

The podcast any of that again I hope you’re enjoying some of these videos it’s fun to be back and talk about some of these things that I enjoy talking about and until next time thanks so much crypto Bobby signing out have a good one peace