I never actually put my investing history down on paper before, so this should be interesting, and it should help me get my point across a lot better if I do as well.
I joined the Marine Corps when I was 17 and shipped off to boot camp at 18.
I was still really young at the time, so I didn’t give investing much thought. This was in the year 2001, and the “The Dot-com Bubble in the United States” was still inflating I believe, and folks were investing in anything and everything with a .com attached to it.
At the time I could care less what was going on out in the real world. I was focusing on all my Marine Corps training, and video games when I had the time to play them. The games I was playing at the time were Grand Theft Auto 3, Metal Gear Solid 2: Sons of Liberty, and Max Payne on my Sony PlayStation 2.
During this time period I already had a pretty lucrative investment already making gains, and for that story we have to go back a ways, way back in time in fact, to the mid to late 1990’s, a time when my mother had given my stepfather the money I inherited after my father’s death to invest in a custodial account, that I would later take full control over when I reached the age of 18 or older.
The amount if I recall correctly was $2,500, and the company my stepfather chose to invest it in for me was Harley Davidson. Fast forward now to 2005, I just got out of the Marine Corps after a 4-year enlistment with an honorable discharge, and my custodial account was finally fully transferred over to me.
The amount I earned from my original $2,500 investment was now roughly $10,000.
Okay, so now let me explain to you what my first biggest investment opportunity failure was. A regret I still carry with me to this day, and one that I hope you won’t make in your own life going forward:
From 2002 to 2005, age 18 to 22, I had the opportunity to enroll in the military version of the Thrift Savings Plan, due to this beauty right here:
“The National Defense Authorization Act for Fiscal Year 2001 extended participation in the TSP, which was originally only for Federal civilian employees, to members of the uniformed services, and members began enrolling on October 9, 2001.”
Source: https://militarypay.defense.gov/Benefits/Thrift-Savings-Plan/
Although no matched contributions were given at the time, this still could have served as an extremely lucrative investment opportunity long-term. I could have designated a percentage of my pay to automatically go into the Charlie Fund, or C Fund as it is properly called, pre-taxed if I chose the traditional option over the Roth mind you, which essentially mirrors the Standard and Poor’s 500 index fund, which from January of 2002 to November of 2023, assuming you reinvested all dividends, is up roughly 500%, or 9% per year.
What makes this regret hurt even more is that in 2006, I went back into the Corps after realizing that the civilian world was just not for me. After two combat deployments to Iraq, and one in Afghanistan, I decided that it was time for me to get out once again.
The year was now 2010, and I had managed to save and invest a large portion of my pay in that second enlistment, seeing as though I was involved in one war after another for the majority of it, and didn’t really have much else to do with it.
All said and done, I’d say my little bag at the time was worth around $150,000, so I felt pretty comfortable trying to make it in the real world this time around. (This figure was after factoring in the roughly $40,000 that my mother gave me to manage for her.)
After many painful years of longing to go back in after my first couple of years out, the reality of the situation was a hard pill for me to swallow indeed. I was too old, and too broken for the Marine Corps, and they definitely did not need me.
It hurt, and still hurts, but it is a life lesson learned, and now serves as advice for myself.
This leads me to yet another of my biggest investment opportunity failures in life:
Not staying in the military, and failing to enroll in the Thrift Savings Plan when I was in.
If I would have stayed in, sure, I probably would have died in Afghanistan on one of my many deployments eventually, but if I survived, I would have a full pension under my belt right now, along with health, dental, and vision benefits for life.
The second part to this last regret, was that during this second enlistment, I still didn’t freaking take advantage of the Thrift Savings Plan!
Don’t be dumb like me, if you’re in or go into the military, try to stay in, because it will set you up for the rest of your life, and if you got or get in at 18, you could retire at 38, which if you’re young, you probably think is so old, but trust me… it ain’t.
Informational: After December 2018, the military converted over to the blended retirement system, which automatically enrolls you into the Thrift Savings Plan, but the difference is, now the military will match your contributions up to 5% just like the civilian version, and most traditional 401K retirement plans.
I won’t bore you with the day to day of what happened when I got out, but I will set this up so you get an understanding as to where I messed up as it pertains to my money situation over the years after I got out.
Now that I was out, I had a lot more bills to pay, because I no longer had a free barracks room to live in, or a chow hall card to eat as much as I wanted to each day.
I filed for unemployment, but almost immediately I started chipping away at my savings, because let’s face it, unemployment isn’t much compared to what I was making in the military, but I was still doing fairly well, so I felt very comfortable at the time.
Of course, I didn’t want a real job, I wanted to live off my investments and start my own business.
So I did, but the business I started was a very race to the bottom style of business, and it was very crowded at the time, and it still is in fact.
I thought I was going to be the top dog and bring in all the customers, which definitely wasn’t the case. I did alright, but for all the years I operated my business, all the way up to the beginning of 2023 in fact, I was always just taking one step forward, and two steps backwards the entire time.
The pandemic really put a hurting on my business, as it did for so many others, and afterwards I didn’t really see a point to operating the majority of what my business did.
I had a YouTube channel for my business that was pulling in roughly $75 to $150 every month. Totally passive income by the way, but YouTube decided that my videos were no longer advertiser friendly, and shutdown my Google AdSense income stream.
So, me being me, either taking one extreme side or the other, I decided after a few days of contemplation, that they didn’t deserve to show my videos and make money for themselves while I made nothing… so I nuked the whole channel. I deleted it, and that was the very last part of my business to be officially sunsetted, and I was finally free of it, along with all the responsibility that came along with it.
This leads me to yet another of my biggest investment opportunity failures in life:
After reviewing the financials of my business each year to see if it was even worth the time and effort to keep going, I ignored the obvious, which was that it wasn’t working.
I didn’t see any worthwhile growth, but kept throwing money at it instead, and managed to go further and further into debt just to keep it going. I should have taken a step back, and decided then and there, that it was time to hang it up, and go get a real job… but I didn’t.
Now that my business venture story has been told, let’s get back to my investing exploits.
The year is 2012, and Facebook is about to kick off their initial public offering, and I was planning on jumping in as soon as they went public.
Oh wait, I’d like to mention here that I had an opportunity to buy and invest in Bitcoin in the 2010 to 2011 timeframe, but pretty much laughed at the guy suggesting it. I ran in these types of circles on the internet, and I was very exposed to Bitcoin in the early days, but never pulled the trigger on a purchase.
I’m sure you can imagine how I feel about turning down that suggestion huh.
Okay, so back to my Facebook investment:
Back in 2012, when Facebook went public, I Purchased 1,000 shares at around $38 per share, and planned on holding them for the long-term, so I didn’t care much about the instant drop that occurred immediately after their initial public offering, which so many people joined in on via a class action lawsuit.
Although, I did learn an investment lesson during all this, which was to buy in via blocks of share purchases, meaning what I should have done was purchased 250 shares apiece over a 4-week period. This way I would have covered myself in case of a huge decline in price, but keep in mind, that this investing tactic could work against you as well if the stock price increases. So darned if you do, darned if you don’t.
This is the part of my life where I was just doing whatever, and my business was only losing money for the most part, so fast forward a way to 2014 and I already started to sell blocks of my Facebook investment just to live off, which was dumb, because what I should have done was got a freaking real job.
If I secured a real job, and left my Facebook investment alone, it would have been worth roughly $341,000 as of writing this, a mind-boggling 797% return on my original investment!
This leads me to yet another of my biggest investment opportunity failures in life:
I learned never to live off my investments, and to always work a real job for income. Whenever I research and fall in love with a new company to invest in, I usually dollar-cost average into them these days, and now I just add to my positions each pay day and watch them grow.
I’ll sell when I retire… and only then!
Let’s rewind a bit to 2013, a very tough year for me, because it was the year I lost my dear mother.
I inherited the $40,000 she gave me to manage for her, plus the gains it made via our joint investments together. This actually led me to make dumber decisions, because I no longer had to worry about blowing her portion of the invested monies.
I started throwing more money at my business, thinking it would solve all my problems and put me on top… it didn’t. I wound up blowing money that would have been better off left in investments while working a real job to pay my bills, and to dollar-cost average more money into my favorite investments.
Fast forward now all the way to March of 2020, and I finally got myself somewhat of a real job. It took me 10 years to finally make this decision, a decision that should have been made a long time ago.
I was working as a car salesman, not the best of jobs, but a job nonetheless, so it is what it is. I worked at the dealership until December 2020, because I had had enough of that crap and left. Then I started getting heavy into gig work, which I will go into more detail about below.
In case you were curious, from 2015 to 2020 I was still running my business, and for a while I was making really good coin selling custom variants of the products my business specialized in. The problem with anything custom though is turnaround times, and the availability of products and materials.
I did some odd jobs during this timeframe as well, and was managing to get by, but was depleting my assets and racking up liabilities like a mad man in the process.
I did the whole Uber, DoorDash, Grubhub, and Postmates thing like I’m sure so many of you did, especially once the pandemic kicked off in early 2020.
What I realized doing these gig jobs though was that it was really beating up my car. I was working really long hours, and in the end, the math didn’t add up… so I quit all of these gig jobs in 2021.
At this point, around March of 2021, my net worth was roughly -$50,000. So, I went from having a net worth of a little over $150,000 at the beginning of 2010, and after all those years, years where the stock market and other asset classes did extremely well mind you, to having a net worth of around negative $50,000… how sad is that?
After thoroughly analyzing my finances, I decided then and there that it was time to get a big boy job once again, a job that had a pathway to retirement, and a retirement investment fund option to boot.
I applied for a county job, and a federal job. I wound up being turned down for the county job but managed to snag the federal job… which was actually a much better score by the way.
This leads me to yet another of my biggest investment opportunity failures in life:
As I was watching my finances dwindle down into negative territory, it was at this point I should have started looking for a real job. I should not have waited over 10 years after getting out of the United States Marine Corps to apply for a real job. If I started working something sooner, I could have lived off the income I was earning from my job and left all my investments alone in order to grow and prosper.
Fast forward to August of 2021, and now I am officially working for the United States federal government once again. I finally had a real job again, and it felt great!
Some of the best perks about my new job was the ability to buy back my military time, which added the 8 years I did in the Corps to my total years at my new agency, which will greatly benefit my retirement pay… assuming I live long enough to retire and collect it.
Also, I finally got to redeem myself, because now I had access to the Thrift Savings Plan once again, and this time I most definitely did the 5% contribute slash match option right from the get-go. I started off in the 2045 Lifecycle Fund, which I quickly changed to my favorite of all the funds, the Charlie Fund (C Fund) of course, and was contributing 100% of my bi-weekly pay allocation to it.
I later changed my tactic in 2023 when I realized the market seemed way overheated, by contributing 50% to the Charlie Fund, and 50% to the Gulf Fund (G Fund), which is essentially an index that emulates the gains of United States Treasury securities.
I plan on keeping this mixture until 2030, as one of my many ongoing finance related experiments. Whichever fund achieves the most gains by January 1, 2030 wins, and then I will transfer all of my funds to that fund, and all future contributions will go to the winning fund as well, until I turn 60 and cash out.
Fast forward to today, and I unfortunately still have some debt left over from my failed business venture, which is roughly around $27,000, so I am not able to dollar-cost average much into my favorite investments yet, but I am throwing a lot of money at this debt soon and hope to have it all gone by 2025.
I also managed to fill up a small bag of speculative investments over these last 2 years or so, which if things go well, these high-risk investments could put me back in the black once again.
This leads me to hopefully my biggest investment opportunity success in life:
Finally, some positivity for a change, because the way forward looks bright from here on out.
Now that I am 40 years old and learned all kinds of painful investment lessons over the many years of my life, the road ahead looks so positive for me and my financial situation.
I just want everyone to know who actually made it this far in my way too long life retrospection, that it is never too late to get back on track. All you have to do is want it, and the road to success shall appear.
Now, it’s time for you to man up like I am, and start walking up that road.
I’ll see you at the top!