From Less Than Zero to Financial Badass Hero

My name is Jack Li. I’m the creator and principal author Badass vs. Dumbass.

In my wealth-building journey, I’ve probably lost more money with my ingenious investment schemes than others have ever made. If you add up those losses, I’ve lost count, maybe down 7 digits.  No pain, no gain, right!?  

Let’s start with the stock market.  I had a front-row seat on Black Monday in 1987, then the Dotcom bubble crash 2000-2002, the Financial Crisis 2007-2008, and of course the recent 2020 Covid crash. But there’s so much more…

I’ve invested in just about everything: mutual funds, stocks via a stockbroker and online, ETFs, options, futures, daytrading, online gambling, professional sports betting, Forex, mortgages, hotels, residential and commercial real estate, syndicated real estate, real estate development, private equity, corporate loans and bonds, cryptocurrency, and so on. On several occasions, I even hired so-called “professionals” to trade for me.

Being exceptionally good at math, If I thought I could find an advantage, I went for it – balls to the wall, motherfucker!   I might have made enough mistakes for several lifetimes. When I look back, I was a fucking dumbass of epic proportions.  Perhaps even a cautionary tale befitting an upcoming Netflix series! Netflix execs, please call 🙂

At one point, I had to take on 2 simultaneous full-time jobs to pay back some credit card loans I took out to fund one of those amazing get-rich-fast investment ideas.   Yes, 9-5, followed by 5 pm to 1 am.   We’re talking GOOD TIMES here, folks!  

There is simply nothing like the feeling of Less than Zero.    Check Robert Downey Jr.’s movie of the same name to see another version of hell.   “Beatings will continue until morale improves” might have been my motto.  Yes, I learned the hard way – the hardest of ways. 

My firsthand experience in the world of money and finances is enough for several lifetimes … I’m lucky to have survived the lean years fully intact (yup, just double-checked – all limbs and digits present).   Can anything beat learning how hot a stove is other than by touching it yourself … DOH!     Since the good old bad days of my early 20s to early 30s, I was on this personal rollercoaster investing labyrinth that took me nowhere fast.  

Now, to be fair, some of those investments were terrible, while others were simply a waste of time, and some were borderline genius.  But of course, no one knows in advance which is which, do they? After living through this, it was the real-world experience in all these areas that led me to discover what worked and what did not.

So, I finally came to my senses (I think I did anyway).   I changed everything about how I invested.   I was a voracious learner and I doubled down on improving my knowledge and focused on what mattered.  I continued to read everything money-related available at the library (something I still do).   I learned about the best and most optimal ways of investing, for ME.    I realized that what works for some doesn’t always work for all.    To be a master, one has to know oneself.    Otherwise, financial ruin is not far behind.  

Better investment decisions have been made along the way, as I constantly refined and honed my strategies.   Now, years later, I am now FIRE and enjoy the fruits of years of stubborn, consistent strategic investing.   If a former major financial dumbass like me can do it, trust me, ANYONE can.   

I retired early in 2015 from a career in IT management.   Working for The Man just isn’t as much fun as it used to be.  Who am I kidding?  It’s fucking horrible for most of us.   At times, it was just a total soul-devouring, time-sucking grind, a means to an end. Yes, you can meet some great people along the way, and if you’re lucky, some who become real friends.  That, I concede is a plus. 

I would have rather devoted my time to reading, biking, long drives in the country, playing my very large music collection, playing tennis, tinkering in my garage and workshop, or just enjoying life by spending more fun time with my family and friends.  All that good shit takes TIME.   The time that was spent elsewhere, dammit.   I would encourage most people to retire early – it’s totally worth it.  Now, if you absolutely love your job/career, stick with it.   Whatever works for you, dude.   You do you 😉  

To be frank, since 2015, I have dipped my toe back into “work”, but you decide if you want to call it that.    From 2016 to 2019, I became a part-time science and math teacher, giving lessons to about 500 elementary school classes during that period.  I had always wondered if I went into the wrong profession when I was young, as teaching was always in the back of my mind.  I jumped at the chance when an opportunity arose.   It paid VERY little.   We’re talking lunch money here compared to my usual rate.  BUT, it was usually a lot of fun.   Having fun with kids is a joy.  I made the lessons engaging and a ridiculously good time for the students, so they all loved it.  

Then in 2019, a very good friend who I worked with on and off over the years brought me an IT management contract that I couldn’t refuse.   The short-term nature of the work, the excellent hourly rate, and the chance to spend time with my close buddy at work – those reasons brought me back.  I felt like Michael Corleone from Godfather III when he said, “Just when I thought I was out, they pull me back in!”  

As I was already FIRE, the question I posed to myself was “Well, you can never really have too much Fuck You Money, can you?”   That contract renewed and renewed, and renewed until finally, it ended in 2023.   The FU money was invested and FAT FIRE was upon me – all good.  

Now I am really retired – I will not go back under any circumstances.  Now I spend 100% of my time on things I love to do, like chilling in my tricked-out man cave, and writing for this site!

If it isn’t already obvious, the Sifu character here is based loosely on me.   Sifu means teacher or master in Chinese.  With my extensive experience in the trenches, I believe that my earned wisdom is worthy of passing on to others.   

The supporting character, Ronin, is an amalgam of my stupid self in the early days, and my young adult son.  I hope my son does not make 10% percent of the disastrous financial mistakes that I endured.   0% would be ideal.   That is one of the main reasons for this site – the information here is for him as much as it is for you.  

Please buckle up and enjoy the ride.

P.S. Please forgive the street language. I blame my foul mouth on Richard Pryor – IYKYK.

E-mail: BadassVsDumbass At Gmail Dot Com

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