So i'm seeing a lot of people in this subreddit recently asking "when bear market", "when crash" and the like. These are either 2017 veterans that are feeling the uncomfortable familiarity or new people that read enough to understand that at some point, the music stops.
After I made a shit ton of money in 2014, and then lost almost all in 2015 I vowed to make sure that would never happen. In 2017/2018 I did a lot better this way, though clearly not perfect. There are basically three strategies you can employ to make sure that at the end of all the coming mania, you're left holding bags, bags of Tesla Roadster 2 car keys that is.
1: The anxious noob: "Just sell the top bro"
Based on your favoured TA, fundamental analysis, youtube video or astrological sign, you pick a price for your current assets, and you sell when it hits that price.
- Clear and transparent
- Potentially genius
- Out of everything you can do, this will fuck with your emotions like nothing else
- Seems simple, until ETH actually hits your 15K price target and you just read someone say it'll hit 50K next week.
- High risk of overshooting your target and not hitting, or undershooting and leaving 300% gains on the table.
- Astrology is generally not very reliable 
This strategy is the noob approach where you think "if only I get out at the right time", you wont, and even if you do, you'll FOMO back in and lose it again. The foresight you need to pick the right price borders on magic, and the massive balls of steel you need to execute this strategy would make Deep_Fucking_Value blush. This approach will most likely burn you big time and I recommend against it.
2: HODL supreme: "Where we're going we don't need fiat"
You pick your bags, and when the market goes up you slowly unload part of your bags to take profit, making sure to always keep at least 50-90% of your bags in crypto.
- You get actual tangible profits to satisfy your greed
- You're never truly out, so it's easier on your emotions
- You can pick some prices and slowly sell your bags when you're comfortable
- Your bags get smaller and smaller as the market rises, potentially passing on very large gains at the top because you sold some earlier.
- Requires fairly active investment, makes it easy to say "well actually lets up the price target 50% before I sell some"
- When the bear comes (and it will) your bag rides all the way down again, which hurts
This strategy is all in all quite solid, and best if you have a longer time horizon (5+ years) if you plan on staying in this market multiple cycles this will pay off big time. It's easier on your emotions because you'll never be the guy/girl/nb that had all their money vaporize, but also not the person that sold btc at $3,50 and now cries themselves to sleep. The profit-taking is an amazing remedy for your emotions because you can't complain when you have actual $$$ in your hands. You won't get the "full gains" of a cycle, but truth is, you never will, because timing the market is a meme.
3: The sophisticated investor: "If traditional finance is building their tools in crypto, might as well use them"
In this case you buy your bags of crypto in a different way. You use assets that can be hedged, have a downside cap or take care of it yourself. Assets such as Invictus Capitals C10 and IBA buy crypto (the top 10 and BTC respectively) but have a hedging element that makes sure your losses are capped (40% max and 10% per month). These kinds of assets give up some potential profits to pay for the hedge. Alternatively, you manage derivatives such as put options on platforms such as FTX to hedge your downside yourself.
- Sleep like a baby because you can only lose so much
- You can ride out the full bull and bear market without lifting a finger
- No need for timing anything or picking your own price targets
- Depending on what you buy exactly you can keep the vast majority of profits of a bullrun
- These assets inevitably cut down slightly on your profits, if BTC goes up 100%, your asset might rise 90-95% to pay for the hedge.
- Less choice, you can buy any shitcoin on finance or uniswap, but there is not always something available to properly hedge it.
This strategy is really great for set and forget, it allows you to just hold through a market cycle, and from beginning to end you might capture 60% of the profits, instead of the 15% that you would just normal HODLing. For example, BTC went from 600 --> 19K --> 3K in the last cycle. Utilizing proper hedging might leave you with the equivalent profits of BTC at 12K. The easiest way to do this is to look for assets that automate this for you. I currently only know of Invictus Capital with C10 and IBA that represent the top 10 and BTC respectively, i'd love to hear of any other similar assets you might know.
Putting it into practice
My portfolio is about 60% these hedging assets and 40% alts and smaller coins that currently can't be hedged. I have set stretch goals for my portfolio where I have to sell X% to enforce I take profits on the way up, and I keep a close watch on crypto chatter and the market to make sure that when I think we're in another heated bubble moment, 100% of my portfolio is in hedged assets. When friends or family ask for advice I advise them to put 100% in hedged assets because they don't spend 2 hours per day reading about crypto (if only it was 2 hours). Your strategy can differ, be a combination or be whatever you want, but I advise you to pick option 2 or 3 and putting the majority/part of your portfolio in there for you own sanity and mental health.
TL:DR; Making money is easy in a market like this, keeping that money is a lot harder.
Disclosure: I am 100% in crypto, financially and professionally and have been for years, thank you for coming to my TED talk