Life – The Ups and Downs


When it comes to life, change is a constant and there will always be good times and bad times. For anyone with any experience in the Game of Speculation, you’re well aware that markets are volatile and resemble something like that of a sine wave.

Ups and downs.

Peaks and valleys.

Life is really no different from speculating — It’s a case study on human behavior and psychology.

Which is why during the tough times, I take solace in the following quote, which has comforted me on countless occasions:


“There is neither happiness nor unhappiness in this world; there is only the comparison of one state with another. Only someone who has experienced the depths of despair is capable of feeling ultimate bliss. It is necessary to have wished for death in order to know how good it is to live.” -Edmond Dantes, The Count of Monte Cristo


Really, without the “bad” how would we even be able to distinguish and determine what “good” even is? So, right now, as I try my best to navigate myself out of a very sticky situation (which has really forced my hand), I’m not going to lament and dwell on the fact that I’m going to be walking away losing hundreds of thousands of dollars.

Yes, it hurts a lot…

But it is what it is…

I mean, just earlier this year, I was celebrating a major accomplishment with you readers when my mining stocks portfolio eclipsed $1 million in profits, and I essentially (more or less) declared “victory”, giving hints (perhaps not direct enough, in hindsight) that I was just about ready to call it a day as an aggressive speculator:

“Since I’ve made my gains, I think understandably so, my focus has to shift to wealth preservation mode much more so than trying to find the next major hyper-alpha-insane gains generation leads.”

Anyway, even while that awesome milestone was playing itself out, in the back of my mind, I was already bracing myself for the coming storm (which I kind of knew was already lurking behind the scenes, due to serious issues pertaining to my out-of-state turnkey turkey rental properties popping up in late 2017).

Granted, I had no idea the severity of the storm, and yes, I probably grossly underestimated the final damage it would ultimately wreak on my finances.

Even now, as I’m writing this, the most recent onslaught of financial devastation that I’ve had to endure isn’t necessarily fully resolved just yet, so I am still somewhat in limbo, patiently waiting for a complete resolution before I can finally move on with my life.

Straight up — It’s been very tough and trying times for me personally, which is why I’m so thankful and grateful to the hardcore readers of this blog who have supported me through thick and thin. Words can’t express what your kindness means to me… It really is giving me the strength I need to persevere and carry on the fight.

I do realize that this blog has altered “off course” this year, and under better circumstances, of course I would prefer to be focusing more of my time, effort, and writing on the “next great investment/speculation idea”, “more success stories”, and so on and so forth.

But you know what, although the Dark Days really suck, they are indeed part of the early FI journey/story and omitting these real life details would be entirely misleading. As mentioned in the beginning of this post, life has its ups and downs and nobody goes through the game smooth-sailing the entire way through.

That’s just not reality.

So why sugarcoat things?

Funny enough, I spoke to a friend recently about my investment disasters, and he had this to say (I’m paraphrasing):

“Everybody goes through shit. Most people just prefer not to share the juicy details b/c it makes them look bad. It’s easier to just sweep things under the rug and not let the whole world know what’s really going on.

And dude, you’re blogging on a public domain!

You’re only damaging your own image and name by talking about your failures.

People don’t want the truth. They want happy fairytales. That’s what sells. That’s how you become popular. That’s how you make $$$ on the web.

I’m sure someone out there respects what you’re doing, but for sure it isn’t the conventional way of doing things.”

I bring the above quote up because it makes me think about certain things…

Years back, I used to be a lot more “conservative” as a blogger. I used to watch the things that I said and oftentimes I refrained from using profanity. I guess I tried to be more careful with my approach to writing because I didn’t want to rock the boat or stir up the hornet’s nest with anyone.

But as time passed, I sort of realized that the “real conversations” that I was having with more and more investors behind the scenes resembled something entirely different from how I was writing and structuring my posts — There was so much more RAW emotion in those private chats!

In “real life”, especially when we’re talking about high-stakes endeavors like investing/speculating, people are extremely: passionate, animated, determined, committed, obsessed even…

So for me, it was very much trying to figure out a way to not only convey the message that I was trying to get across, but also figuring out a way to keep intact the RAW emotion element of things.

As such, that partially explains why I like to “ramble” so much… Yes, with profanity-laced diatribes unedited and all.

Anyway, when you link all that up with the highs and lows of investing, well, again, it’s going to be very emotional, particularly if you want the real authentic experience.

And I really don’t want to take that away from readers. I don’t want to revert to my old school more conservative ways where I was watering down everything; that’s bullshit and not the true story!

Yes, the highs are awesome and making money puts you in a state of mind that is beyond euphoric…

Private conversation from late 2017.

And losing money really sucks…

Private conversation from earlier this year…

The above text (from a close friend) is actually a lot more “mild” than some of the stuff I regularly get from friends/family…

Then there’s the above, which sums things up succinctly…


This last group chat above was both sad/funny… and reeked of despair.

Something like that…

You get the idea.

I want this blog to capture and encompass all the RAW emotion that makes life exactly what it is… What makes us human.

I’m never gonna have all the right answers.

I’ve made too many mistakes to count and i will keep making them throughout the course of my life.

We are imperfect creatures, after all.

So, I want to share with you all: the good, bad, and ugly.

And you can see that even during the grueling hardships, when all hope seems lost and life is indeed a living hell, well, we can still overcome all obstacles!

Yes, I may bitch and complain a lot, and during the lowest of lows my confidence will be shattered and I will feel like throwing in the towel, but I won’t ever give up!

Hopefully, despite all the negativity and “doom and gloom” floating on here at times, there’s someone else out there who can resonate with what I’m going through and perhaps they can find strength and the motivation to keep going too!

Misery loves company, but together we are stronger!


Once the storm has cleared, yes, I really would like to resume back to the ol’ regular scheduled program!

Until that moment arrives, I hope you all can bear with me as I try and navigate out of my own personal financial nightmare situation.


Here’s that quote again:


“There is neither happiness nor unhappiness in this world; there is only the comparison of one state with another. Only someone who has experienced the depths of despair is capable of feeling ultimate bliss. It is necessary to have wished for death in order to know how good it is to live.” -Edmond Dantes, The Count of Monte Cristo


All things considered, really, it feels damn good to be alive!


Thank you all for sticking by me, in the good times and bad.


Fight On!

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2 years ago

Jay, I admire your blog. Yes, it has changed course to some extend – content wise. But most importantly you stayed the course: authentic and true to your values.
I do appreciate your writings alot. Even if they are depressing at the moment – but that is ok!!! As you say: that is part of life!
I will keep reading every article and am sure we will hear about plenty success stories in the future. Also looking forward to your masterplan on how to win it all back… 😉
Keep it up!!!

Jan Deman
Jan Deman
2 years ago

Jay, How can you be a wise and good person if you have never been in the shit? Life is stumbling and always right back. Being a righteous person is daring to share your misery with some people and not be a hypocrite. Keep believing in yourself, you will stand upright again. Keep it up! JPC

2 years ago

Hey Jay, these kind of things are normal for big players… It’s all a good experience even if at the moment is just shitty.

I’m a bit older than you and probably I had more shitty times than you, so whenever for a prolonged period of time things are going well, I prepare myself for the next storm because I know is coming.

It is not a six sense, it is just how life works.

2 years ago

Jay, I’m a longtime reader and fan of your blog. I wanted to let you know that I appreciate you sharing your experiences, the good and the bad. Honesty that’s public facing.. I think that’s hard to come by in the online/investing world. So just wanted to say that it’s refreshing and here’s hoping this down stretch for you is over soon.

Nick B
Nick B
2 years ago

Jay. Love the blog and it’s actually one of few I actually read anymore. Interested to hear your experiences good or bad. I FIRE’d a few years ago now and started a unprofitable side business. I’m now over extended into the venture and will likely take a bigger loss than I can absorb. Worse case I have to get another job, at the end of the day, a few year mini-retirement between jobs is not all that bad. I can’t complain either, overall I’m super lucky and I’m working on becoming more Stoic by the day. Looking forward to hearing… Read more »

2 years ago

Jay I know it is hard right now but soon this will be behind you. Nothing stays forever and this will be a thing of the past. I love your blog and read every single piece of post that you have written, pretty inspiring. No matter how hard we try sometimes we can’t control shit hitting the fan. We all live through this and get something valuable – wisdom.. hang in there partner and keep us informed about the SHitcago progress. We like it in good/bad/ugly RAW fashion. No sugarcoating as it is unreal..

2 years ago

Jay, keep rollin’ ….
Everyone needs to go through a deeeeeep valley once in a while.
You have been a major inspiration. Keep on being one through the highs and the lows!!