Trading Crypto to the Moon Episode 7: Interview with JesseOlson

6 min readDec 31, 2021


Greetings Alunauts,

In this episode of Trading Crypto to the Moon, we had the honor to interview @JesseOlson, a seasoned crypto and options trader and technician. Jesse is super active on Twitter, posting and sharing market insights several times a day to his 38,000+ followers.

Trading Crypto to the Moon Episode 7: Interview with JesseOlson

Read on to learn more about Jesse’s epic trades, how he decides when to exit the market, top indicators, and tips for traders starting out in this market. If you haven’t done so already, follow Jesse on Twitter for regular charts and breakdowns of his crypto and stock option trades.

On to the interview….

  1. Please introduce yourself and tell us more about you. Where are you from? What do you do for a living? What do you like to do in your spare time? What are your hobbies?

Hey everyone at Aluna.Social. ! I’m on Twitter as myself @jesseolson & I currently live in SoCal. Recently married & I enjoy outdoor adventures, chess, golf, football, & I am obsessed with charts, lol. I’ve been self-employed most of my working life & 16+plus years in Real Estate.

2. Awesome. How long have you been trading?

For 10 years I thought I could do well & would enjoy trading but I was always too busy building my business to dive in. Fast forward to April 2020, I dove in and have been obsessed with charts ever since. Starting out in options trading and moved over to crypto a little over a year ago. Countless hours put in every day so I don’t just throw the word obsessed around.

3. What was your most epic trade or investment ever?

I’ve had a lot of good ones, some bad, but the ones that stick out the most are TSLA short from $880 to $650, Bitcoin long at $32.3K coming out of correction. Bitcoin long at $43.4K coming out of correction & the ETH short I’m still in. These ones were/are top gainers & I spent a good amount of time setting up the trade before taking them.

4. Nice, it looks like you mostly trade crypto, or other assets as well?

Yes, mostly Bitcoin but I’ve also traded Etherum & several option trades. I do prefer crypto because options expire.

5. How much of your investment portfolio is allocated to crypto vs other assets (in terms of %)?

I would say 95%.

6. Can you tell us about your trading strategy or trading plan?

Sure, I am mostly a short to mid term swing trader, but also hold spot bitcoin for the long term. My trades include using leverage on crypto similar to options.

7. Do you use indicators, and if so which ones?

I mostly use RSI as a Leading indicator. I am most proud of coming up with a way to use RSI divergence that I have never seen used by someone else before. I continue to backtest this method on crypto & options trading. I keep MACD indicator on my chart to confirm a trend is still in place but it’s a lagging indicator.

8. Sounds interesting, do you mind sharing more about this “unique way of using RSI divergence”?

No problem! There are several bullish & bearish divergences out there like “hidden” as an example but I only focus on one bearish/bullish divergence. Divergence just means as RSI peaks (circled) are going lower while Price peaks (circled) continue to go higher. The part that I have never seen before is that the slope or angle of the divergence trendline drawn on RSI is very similar to where price could be in the future (dotted line). I posted these below charts in July, the first chart shows the bullish divergence and I drew out the dotted line. The second chart shows price came back to test the dotted line & beyond. This has been one of my biggest discoveries for helping to identify a trend reversal AND give a solid target to aim for. I personally use divergence on the daily chart even though I’ve seen it work on lower time frames, the reason why is that lower time frames give “false signals/fake outs”. The daily chart price can remain diverged with RSI for days, weeks, or months similar to the bearish divergence of early 2021 chart shown below.

9. That's awesome, thanks for that! Which time frames do you usually trade?

I make business decisions based on the 8 HR chart or higher time frames like the daily chart but I like to look at charts ranging from 1 HR all the way to monthly candles.

10. How much do you generally risk per trade and how do you decide on the position size?

Depends where I decide to put the stop loss and/or how much research I have put into the trade. I am more aggressive right now but my plan in the near future is not to be as aggressive.

11. Do you have any specific financial targets/goals this year, or this bull market?

The main goal is to “nail the top”of this bull market so that I can pay off my parent’s home.

12. Do you have an exit strategy for the bull market? Do you plan to scale out, and if so, into which cryptos/assets and how?

Multiple strategies deployed but for spot, I plan to hold unless there is a clear blow-off top which hasn’t happened yet, then buy back in once I feel the bottom is in. Whereas my swing trades I take profit once there is a sell signal which for me is a breakdown of a trend line I feel is important, wait for the next set-up, and then do it again.

13. How high do you see BTC and ETH reaching this bull market?

The high so far is $69K for BTC & $4870 on ETH. Until price makes a higher high, then those are the highs. If they both make higher highs, then I could see BTC reaching $100K+ & ETH $5K+. If an asset goes into Euphoria stage, then the price can go much higher than one might think.

14. What advice would you give to new traders?

New traders, I would take it slow vs jumping headfirst into options trading like I did. You’ll save yourself money in the beginning by doing so. You can see what I do for free on Twitter as I post a lot of charts & you could even start paper trading on

15. Any last tips, alpha, words of wisdom for our fellow crypto traders? :-)

Leverage & options trading is for “experts only”. If you are asking people where/what/when to buy/sell, then are you an expert? One last thought, I think the hardest part to master are the emotions. (FOMO, GREED, & FEAR) Thank you!

A big thank you to Jesse for this interview! We appreciate you sharing your trading insights with Aluna.Social and our community.

Liked what you read? Check out our previous Trading Crypto to the Moon Episodes below:

Episode 6 with Wulf

Episode 5 with Cryptopathic

Episode 4 with Gorankit

Episode 3 with Astolatt

Episode 2 with Magnus

Episode 1 with Paranoid

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