The 21 Fund

The mission of The 21 Fund is to strategically achieve incremental wins over the course of two years, aiming to earn enough money to acquire the prestigious Omega Snoopy watch.

TOTAL Profit/Loss: $0.00

December 10, 2024

Starting Bankroll: $5,300.00

Ending Bankroll: 0.00

Profit/Loss: -$5,300.00

Catastrophe! The fund has been lost :(

For anyone who has been kind enough to follow along on my grand little experiment, it is a sad day today. Two weeks ago I hit a terrible run of cards. The game started in earnest like any other game but stretched on for hours. Loss after loss compounded. And as evening turned into late night, I found myself on tilt and in a heightened state of anxiety. I had lost in hours half of what I had so patiently built over the preceding weeks. I shut down my computer and walked away—disgusted but determined to make right the next day what had gone so terribly wrong on this day.

Things got worse the next day. I began losing immediately and was never able to claw my way back to even. I was playing between $50 to $100 per hand which given my depleted bankroll from the previous evening, exceeded my preferred bet size to bankroll risk % tolerance. Still I persisted out of a misplaced eagerness to regain lost ground with devastating consequences. The 21 Fund was lost.

Okay, so what happened? I showed three months of consistent earnings that outpaced even some of the best investments on the financial markets... and then this?! The graph has been (almost always) up and to the right. But I suppose that "almost always" caveat is what gets you. This was my 1929. I won't talk about my theories of risk and limiting time spent in game—those can be found in some of my previous musings... but I will address the elephant in the room: why did I not simply put guardrails on my downside losses? A circuit breaker, if you would, that triggered when I hit a certain threshold to direct me to walk away from the game.

The reason is this. My total investment in this experiment was $200 plus a whole pooload of time. I spent almost every evening for the past three months playing this game and turned my starting capital into over $5,000. However, I really was not willing to invest more time into this apart from what I was already committing. So if I limited my losses to $750 in a single game, for example, it would then require me to play for perhaps a week or two to get back to where I was before taking that loss. The much riskier move, but one that had frequently worked for me, was to play through those losses in that same session until I could get myself back to even. This would allow me to avoid a major setback and the subsequent time required to recover from it. The clear downside being that it eventually caught up with me and the bankroll that I worked so hard to earn is now gone.

The good news is this. I did, at times, take some money out of the fund (but did not record those sessions as I treated them as being outside of this experiment)—so at the end of the day, I am whole. But what is next? At this moment, I do not think that I want to take another run at rebuilding the 21 Fund. I just don't want to invest the time to do so right now. But there does feel to be a gap in my life and as I think back at this experiment, I really enjoyed playing with different AI models and pouring over the data. As a result, I have been attempting to build my own blackjack simulator (using AI, of course). This web app will allow the user to instantly generate thousands of blackjack hands and provides them with different levers to test different strategies. It is still buggy but my prototype can be found here. There are more options I want to add and I have some ideas around a social element to it too. This is a passion project and we'll see how far I can take it. But I'm having fun with it right now and will continue to tinker and update it in the days and weeks ahead.

Thanks to anyone still reading this thing. It was indeed a grand little experiment for me. This was not the first iteration of the 21 Fund and perhaps one day (after simulating thousands of hands and testing hundreds of different strategies), the 21 Fund will live again. Until then, onwards!

November 21, 2024

Starting Bankroll: $5,200.00

Ending Bankroll: $5,300.00

Profit/Loss: $100.00

Alright, $5,000 was a nice milestone—but let's keep this train rolling, baby. Quick game tonight—100 bones in the bag. Tomorrow I shall play poker. Of course it will not contribute to the 21 Fund when I take all of Lorne's money. That will be just for fun. Nah, I'm just talking trash. Lorne may take all of my money in the end... but with triceps that small, it's unlikely. OOOOOOHHHHHH SNAP!

November 19, 2024

Starting Bankroll: $5,000.00

Ending Bankroll: $5,200.00

Profit/Loss: $200.00

Today the 21 Fund achieved $5,000 in profit—this is a lovely milestone. However, I did so by pushing my concept of "incremental" winning a little bit. I should have walked away after hitting the $100 mark. However, with that $5,000 profit milestone luring me in—like a siren song to a sailor from the depths of the sea—well, I had to push it. The decision to do so paid off.

Contrary to the narrative of this site, the 21 Fund commenced in earnest some 20+ years ago. At that time, Lorne and I were gambling excessively and we believed implicitly in our unyielding ability to earn. The 21 Fund lasted for about 4 days before we blew our bankroll and shut her down—maybe a little bit worse for wear and slightly with our tails tucked between our legs. This was the first domino in a series to fall that would pull Lorne and myself away from the tables and into other corners of life.

In the intervening years, I have often thought about risk in blackjack as a function of both bet size to bankroll % and time spent in game. If you can minimize both of these variables—well, that's really the whole premise of the fund. My desire to start this up again was catalyzed when I was extorted by the police in Prague and decided to gamble to make myself feel better. I am surprised that this premise has held so consistently for these few months I have run this experiment... and here is hoping for continued and statistically probable good fortune! So on this auspicious occasion, it feels only appropriate to end with this flash video (darn you, Steve Jobs) created by Lorne to commemorate our gambling some 20 years ago (while posted on YouTube 12 years ago, the video first originated on our Spiting Peter website several years before that). Thanks to anyone who is still interested in this little corner of the internet.

November 18, 2024

Starting Bankroll: $4,850.00

Ending Bankroll: $5,000.00

Profit/Loss: $150.00

What a nice couple of hands this session. I also got to end them on the most statistically advantageous double down that a player can be dealt: an 11 against a dealer's 6. And when that 10 of spades hit my hand—well, it was as if angels were singing. The dealer busted (as was the statistical likely outcome), however, it is always nice to find yourself in a moment where you can't lose. You don't get many of those moments in life, so you ought to seize them while you can young grasshoppers.

November 16, 2024

Starting Bankroll: $4,750.00

Ending Bankroll: $4,850.00

Profit/Loss: $100.00

I almost finsihed Erik Larson's new book today, "The Demon of Unrest". However, when a book is this darned compelling, I prefer to stretch out those final chapters. It profiles the powderkeg that was the United States in the months leading up to her civil war. As tensions mounted between the abolitionists and the secessionists—and as the political, social, and moral divide deepened between these two groups—the inevitable war ignited when the south commenced a seige on Fort Sumter and the Union garison that was defending her. This would kick off a bloody four year war that would end with 700,000 Americans dead and millions more injured. On the other hand, today was a pretty nice day at the tables.

November 15, 2024

Starting Bankroll: $4,650.00

Ending Bankroll: $4,750.00

Profit/Loss: $100.00

Solid game this evening. Not an easy one. But also not one of those ones that leads you down a pit of despair. While I would love it if every win could just be handed out on a silver platter—the adversity of the thing also makes one feel alive. We are inching closer towards the goal! And in the words of my good pal, Ben—"Snoopy by next fall!"... from his lips to Ganesh's ears.

November 14, 2024

Starting Bankroll: $4,500.00

Ending Bankroll: $4,650.00

Profit/Loss: $150.00

T-Swift may be shaking it off in Toronto tonight, but I've been shaking down the house today! Okay, that was pretty bad—but I tried. Anyhow, this was another nice quick session. And always fun to finish off on a successful double down. And hey, Taylor may be saying, "I've got a blank space, baby", but my chips are taking up all the blank spaces on the table! (Okay, I think I just made it worse.) Xoxo.

November 12, 2024

Starting Bankroll: $4,350.00

Ending Bankroll: $4,500.00

Profit/Loss: $150.00

Another quick one today! Which has been made all the more possible given that my definition of "incremental" has evolved since this experiment commenced. At that time, my bank roll was only $200 and my average bet was between $5 and $10. Thus, the absolute dollar value of each bet was quite small while maintaining a 3-ish% bet size to bank roll ratio. Now that my bank roll has grown, the bet size dollar value has also grown an order of magnitude while simultaenously the bet size to bank roll ratio has decreased (aka, risk). This is all to say that my bank roll is now increasing by an absolute amount more than it ever has before. Which means I can decrease the amount of time I stay in a game (because earning $100 in two hands is a more satisfactory outcome than earning $20 in four hands, for example). This further decreases risk. Look, I'm always still one bad decision away from losing it all, but it is pretty darn interesting how this has played out so far!

November 10, 2024

Starting Bankroll: $4,200.00

Ending Bankroll: $4,350.00

Profit/Loss: $150.00

Fortune favoured the bold today. Well, maybe less the bold and more the statistically probable. I play my hands, after all, in the style pioneered by Edward Thorp and his seminal book "Beat the Dealer". What a fascinating dude. A scientist, a professor of mathematics at MIT, and more recently, a hedge fund manager—the man is brilliant. He came up at the dawn of the computer age, and while few people in the world got the implications of the computer at that time, he was a part of the few people who did. Thorp learned punch card programming and embraced the new computational power available to him to test his algorithms and theories on blackjack. In doing so, he became the godfather of card counting and basic strategy (though in all fairness, the concept of basic strategy was first described by four U.S. Army engineers a decade before who called themselves the Four Horsemen of the Apocalypse which was further revised by Thorp in "Beat the Dealer"). And while most academics would stop there—Thorp was not most academics. This was a man of action. Looking for ways to test his thoery, Thorp ended up bank rolled by a Vegas mobster for $10,000. When after a single weekend he walked away with $11,000 profit, they knew they were onto something. He went on to study and "beat" other casino games before launching an extremely successful hedge fund. Contrary to the brilliance of Thorp, I am not pioneering any great mathematical insights with the 21 Fund. I am not capable of that. But what I do understand, as someone who has both played and dealt thousands of hands of blackjack, is the psychology of the game. Today I walked away from my session after only two hands of play. How many gamblers actually do that? My estimate is almost none. Because it is the hardest thing in the world to do while winning. It goes against every fibre of your being. Yet it is this very reductionist (but shockingly effective) insight coupled with bet size/bank roll management that has allowed the 21 Fund to see the success it has seen thus far. I hope that maybe somewhere out there, even the 92 year old Thorp, would find this grand experiment at least a little bit interesting!

November 9, 2024

Starting Bankroll: $4,150.00

Ending Bankroll: $4,200.00

Profit/Loss: $50.00

The trend from the last three sessions came to an end on this one. While it could have been worse, tonight was a battle. Mind you, it was not one of those existential battles where everything comes crashing down and your survival seems precarious at best. But it was enough of a battle to get the heart rate pumping on a night where I did not particularly desire to pump up an elevated heart rate. In the end, we came out one hand on top (as opposed to the typical two hands I have been attaining as of late) and 50 bones in the bank. However, given the ups and downs of the evening, I am not in the mood to wax poetic about the Aztecs and the cyclical nature of the universe tonight. I am, however, happy that this grand experiment shall continue. Onwards!

November 7, 2024

Starting Bankroll: $4,000.00

Ending Bankroll: $4,150.00

Profit/Loss: $150.00

Holy mackeral. Three easy days in a row. I'll take it—but boy does that make me nervous. I am a firm believer—as the Aztecs were—that life is cyclical. That the bad is always preceded by the good. And when Cortés showed up to the new world, and wiped their people the frik off the map, the Aztecs still maintained their faith to the end, believing that this too would pass. But it didn't. The Spaniards did not relent and the cyclical nature of the world that the Aztecs believed that they inhabited did not prove true. Instead, the massacre persisted, the conquistadors took Tenochtitlan, and the Aztec bloodline came to an end. Here's hoping the same thing doesn't happen to the 21 Fund!

November 6, 2024

Starting Bankroll: $3,900.00

Ending Bankroll: $4,000.00

Profit/Loss: $100.00

Boo-yah! That was a quick one. And for the first time ever, the ending bankroll amount is preceded by the number '4'. This feels substantial. Oh, and by the way, Trump just won the election. I guess that feels kind of substantial too.

November 5, 2024

Starting Bankroll: $3,750.00

Ending Bankroll: $3,900.00

Profit/Loss: $150.00

Slow news day today.

November 3, 2024

Starting Bankroll: $3,720.00

Ending Bankroll: $3,750.00

Profit/Loss: $30.00

Frik me. So much for yesterday's sentiment. I played today for 2+ hours and 162 hands. This was less than optimal—in fact, it was an absolute grind. Fortunately, I clawed my way back to even and also attained a couple extra bones for my troubles. But geeze louise, tonight was a bit too stressful. And to boot, my data capture techniques failed me. When hands extend ad nauseam, as they did tonight, the AI breaks down. First off, my rabbit r1 that I record raw data via audio input began to periodically glitch out. Here's an example of one such hand that it transcribed: "Note, I'm playing a new blackjack hand. Vet size $100. I have an I My first date, I have a 2 On my first date, Thank you. Have piece of diamonds. Nice stand, Nice. My second 8, the dealer has a 2 of clubs. A 2 of clubs, a ace of spades, a 4th I win and I lose." I mean, what the frig do you do with that? And then, as a double whammy, ChatGPT's o1 model was unable to keep pace with the excessive amount of data I threw at her. Thus, tonight's table is entirely incomplete. But working with what the AI gave me, I'll post the first couple dozen hands and then jump to hand 162. Yes, it is less than ideal losing 90% of your data, but better than nothing, I suppose. Also, one final thing. Do you realize how many times tonight I was one hand away from my incremental win and walking away? Too many times. And each time, after having it dangled a hand's length in front of me, I would subsequently lose hand after hand and then have to claw my way back up. Anyhow, here we are! Life sometimes tests you, as it did me tonight——onwards!

November 2, 2024

Starting Bankroll: $3,620.00

Ending Bankroll: $3,720.00

Profit/Loss: $100.00

Nice way to kick off our November sessions! The double down at the end certainly got my blood pumping. Pulling an ace on an 11 double down is the worst outcome that one could achieve. But Ganesh was smiling and the dealer pulled a 6 under his face up 10. This ultmimately led to the dealer busting on a 9 and myself taking down a $100 win to achieve my incremental profit for the day. Here's hoping that this game foreshadows both the excitement and the success (but I'll also just take the success) in the month ahead to come.

My October 2024 Month-End Review: A Journey of Discipline, Resilience, and Incremental Gains

October has been a month of growth—not just in my bankroll but in my understanding of discipline, risk management, and the emotional aspects of gambling. As the month comes to a close, I want to reflect on the highs, the lows, and the lessons I've learned along the way.

The Highs

One of the most satisfying achievements this month was watching my bankroll grow from $2,087.50 to $3,620.00, a net profit of $1,532.50. This steady increase reinforced the effectiveness of focusing on incremental gains and disciplined play. Each small win contributed to significant overall growth, proving that patience pays off.

Another high point was my successful use of blackjacks and double downs to boost profits. For instance, on October 1st, I hit a blackjack and followed it up with a successful double down in the same session, leading to a net gain of $137.50. Moments like these highlighted the importance of capitalizing on advantageous situations while sticking to my strategy.

The Lows

The most challenging part of October was undoubtedly the significant loss I faced on October 6th, where I lost $1,300.00 in a single session. I allowed myself to deviate from my strategy, chasing losses and making emotional decisions. This setback was a harsh reminder of the risks involved when discipline wavers.

However, the very next day, I managed to recover with a gain of $1,350.00. While I'm grateful for the turnaround, it also highlighted how easily one can get caught in a cycle of risky behavior when emotions take over.

Another low was realizing the impact of longer sessions on my performance. On days like October 6th and 25th, extended play led to increased variability and fatigue, affecting my decision-making. It became clear that longer sessions weren't aligning with my strategy of maintaining focus and discipline.

Lessons Learned

If there's one key lesson from October, it's the importance of sticking to my strategy—especially during challenging times. Chasing losses only led to greater setbacks, and maintaining discipline proved crucial for long-term success.

I've also learned the value of short, focused sessions. Most of my profitable days involved playing only a few hands, which helped me stay sharp and make better decisions. Going forward, I'll aim to set clear session limits to prevent fatigue and emotional play.

Additionally, effective bankroll management has been vital. By keeping my bets at a small percentage of my total bankroll (around 1.7%), I was able to mitigate risks and preserve capital, even during downswings.

Looking Ahead

As I move into November, my goal is to continue building on these lessons. I'll focus on maintaining discipline, sticking to my strategy, and embracing the power of incremental gains. I recognize that the key to sustained success lies in consistency and the willingness to learn from both my successes and setbacks.

Here's to a new month of growth, discipline, and steady progress. May November bring more opportunities to apply these lessons and continue this rewarding journey.

October 31, 2024

Starting Bankroll: $3,612.50

Ending Bankroll: $3,620.00

Profit/Loss: $7.50

Betelgeuse, Betelgeuse, Betelgeuse

October 30, 2024

Starting Bankroll: $3,500.00

Ending Bankroll: $3,612.50

Profit/Loss: $112.50

Whilst playing on this evening's Devil's Night, the devil appeared to be kind. Two blackjacks in a row?! Forget about it. This was a very fortuitous occurrence indeed. However, I am now sattled with 50 cents trailing on my bank roll. And anyone who knows me will instantly know that an extra 5o cents on my bank roll drives me bananas. I now need to bet in $5 increments in the hopes of hitting another blackjack that will give me another 50 cents which in turn will round up my bank roll to the nearest dollar. But until then, my OCD will be triggered. And to that unfortunate situation I say—FUGGETABOUTIT!

October 29, 2024

Starting Bankroll: $3,400.00

Ending Bankroll: $3,500.00

Profit/Loss: $100.00

In what may be the finest film to come out of 1992 (with the obvious exception of Scent of a Woman), David Mamet's Glengarry Glen Ross introduced us to a simple concept that would resonate with generations to follow: A B C—Always Be Closing. Whether you are working in a boiler room or you are 15 years old and trying to close on your first piece of tail while your grandmother and aunt babysits you, it is a maxim that still holds true today. So how does this apply to the 21 Fund? Well, it doesn't really. I could hyperbolically insist that the 21 Fund requires this same skill. But the truth is, I really just wanted to say—PUT. THAT. COFFEE. DOWN. Coffee is for closers only. You call yourself a salesman, you son of a bitch? Only one thing counts in this life—get them to sign on the line that is dotted. Do you know what it takes to sell real estate? It takes brass balls. Okay, okay, I guess that's enough. Today's "sit" was a good one. The incremental gains continue. I just hope Mitch and Murray don't send Alec Baldwin down to reprimand me if I begin to lose my edge.

October 28, 2024

Starting Bankroll: $3,300.00

Ending Bankroll: $3,400.00

Profit/Loss: $100.00

I logged a very long work day today—so I am thrilled that, conversely, the 21 Fund yielded a quick win. As a result, I can no longer stare at my computer screen. Peace and love, everybody!

October 27, 2024

Starting Bankroll: $3,200.00

Ending Bankroll: $3,300.00

Profit/Loss: $100.00

Sunday Funday with a relatively quick session today! It's funny—I now play so excessively that I have gotten to know all of the dealers complete with their personalities and quirks. Some of them I avoid religiously. Others I seek out. This is not because of some superstition that I hold. Rather, it is because I don't enjoy playing with somebody who looks unhappy or picks their ear (yes, one of the dealers does this regularly). The dude who was my dealer today is the cream of the crop. He is professional and enthusiastic and portrays a genuine vibe of rooting for the player (and doesn't pick his ear). Now that's my kind of guy! While the game went quick today, it would have went quicker if I didn't hit on each 12 that I was dealt. I hate a 12 against the dealer's 2. There is no statistical advantage in this scenario to either hitting or standing—thus, you are free to follow your gut. My gut in both instances that this occurred today failed me. But all's well that end's well and we have reached another $100 in incremental gain. By the way, if you are wondering why I hyperlinked to Stevie Wonder's smash hit Superstition a few sentences ago then I don't want to talk to you anymore.

October 26, 2024

Starting Bankroll: $3,100.00

Ending Bankroll: $3,200.00

Profit/Loss: $100.00

Well, this is a nice contrast. Last night I played approximately one million hands (okay, maybe it was 124 hands, but one million is certainly what it felt like). I spent hours working the fund while also wrestling with various AI sources that failed to tabulate my extensive data from the session. Meanwhile, today I hit two quick and successive wins that secured my incremental gain within about 5 minutes. It is funny how the fates work, isn't it? Sometimes they giveth and sometimes they taketh away. But they always remain cold and calculating and true. And I suppose you either have to believe in the math of the thing and that you will ride out the waves of despair—or you don't. Prior to his death, my favourite Canadian fiction author, Timothy Findley, used to sign his letters to his friends and family with the epigraph: "hope against despair". I think of this often. Thus far the fates have permitted the hope from the 21 Fund to outshine its moments of despair. Time will tell if this persists!

October 25, 2024

Starting Bankroll: $3,000.00

Ending Bankroll: $3,100.00

Profit/Loss: $100.00

Frik me. It's tough to know where to begin on this one. I visited our nation's capital over the past few days. This resulted in excessive steak consumption (thanks Rami!) and excessive gin martini consuption (thanks Gianni!). Not to mention the occasional train evacuation (hello Joseph!). While I was not contributing to the 21 Fund during this time, I did find myself in a casino "IRL"—as the kids say. I forgot how much I missed playing on the felt, baby. And also being gregarious with my table mates. All the camaraderie and all the backslapping and all the hooting and hollering—we were the envy of the casino! I ended the night one hundred bones up (and several orders of liver functioning magnitude down). So good on me.

And then there was tonight. Tonight I worked the 21 Fund for hours and was down over $1,000 at one point. I clawed my way back up and am walking away from this adrenaline-inducing evening with $100 profit—but geeze lousie, things were touch and go for a while. I still have not reconciled in my brain how to accept a loss on this thing. And this single trait has become both my greatest superpower and may result in my inevitable downfall. There were also soooo many hands played tonight that ChatGPT's o1 Preview model would not output all the data. So in spite of even more hours attempting to find a hack, tonight we're stuck with a truncated table. Lame. The good news is that I finished tonight's session in the black. So you know, this evening I shall take the sweet with the bitter.

October 21, 2024

Starting Bankroll: $2,900.00

Ending Bankroll: $3,000.00

Profit/Loss: $100.00

I find there is always a nice energy on the 21st day of the month—for obvious reasons! Today, for the first time ever, I opened up my session with a $50 bet size. Truth be told, consistently gambling beyond $25 per hand makes me nervous. This is the range that Lorne and I had commenced our gambling careers after all—playing with a $200 bank roll @ $25 per hand. However, the mathematics of the thing makes sense. This whole experiment began in earnest on a $200 bank roll with bet sizes ranging from $5 to $10. At only $5 hand per hand, the bet size:bank roll ratio equated to 2.5% when the 21 Fund first begun. Now with $3,000 in the bank (and I am happy to have hit that milestone today, by the way!) and at $50 per hand, the bet size per hand as a % of the total bank roll has decreased to 1.7%. Thus, from a risk perspective, I am better off gambling $50 per hand at my current bank roll rather than $5 per hand at my initial bank roll. And herein lies the kind of cool thing about this experiment. As I gamble at these higher dollar values, I should theoretically increase my bank roll in step. This in turn allows me to increase the bet size while maintaining the same % per hand of the total bank roll—aka, it is a virtuous cycle! Don't get me wrong—this can all implode on me. But gambling at a rate of less than 2% per hand of your total bank roll feels like a pretty strong risk mitigation move. It gives you sufficient buffer to ride out the dark days until you find yourself in the light again. This also allows you to ramp up your bank roll for the same risk at an exponential(ish) rate and not just a linear one. All this is to say that today was a nice day and here's hoping we can keep this train rolling!

October 20, 2024

Starting Bankroll: $2,850.00

Ending Bankroll: $2,900.00

Profit/Loss: $50.00

Ganesh was smiling on me today—it was another quickie! However, runs like this can lull one into a false sense of confidence. It is maybe a quirk of human resiliency (or ego?) that we are quick to forget our hardships and instead tunnel vision on our successes. Right now, I feel proud and good; strong enough to beat the world. But the reality is that there were two or three occasions since I began this grand experiment where it all could have come crashing down. If not for a timely blackjack here or an unexpected dealer bust there, the 21 Fund may have well been done and dusted. I say these things out loud to remind myself that as in life, there are no certainties to this game. The thesis of my grand experiment has been contentment with incremental gains while mitigating risk. The psychology of gambling makes it unbelievably difficult to walk away from a winning game when you are only a couple hands up (ie, incremental gain). This is against human nature. But the cards will always turn on you. And when they do, your bet size as a % of your bank roll better allow you enough plays to outlast the downturns and fight your way back to even (ie, mitigating risk). Although imperfectly, this is how I have endeavoured to play every game. And the consistency of the wins thus far have shown a rightness to this strategy. But I do remain accutely aware that unless I implement further guard rails to mitigate the downside risk on this thing, I am always one terrible streak of luck away from ultimate disaster. But maybe that is all just an analogue for life? Anyhoo, food for thought. Peace and love, everybody!

October 19, 2024

Starting Bankroll: $2,800.00

Ending Bankroll: $2,850.00

Profit/Loss: $50.00

The early bird gets the worm! Nothing like a Saturday morning game of blackjack to get the blood pumping. However, I was quickly confronted by crisis. As I sat down at the tables and grabbed my trusted rabbit r1 device (which Mo is racist against) to record my session, I looked down at the screen and panicked. My rabbit r1 was crippled—she had just commenced a software update. It was too late though!—the cards were already out of the shoe and the dealer had begun deftly placing them onto the table one by one. Showing a profound mental agility coupled with some real world grace under fire, I rapidly grabbed an old school pen and paper and scrambled to log each hand by hand. My courage was rewarded by lady luck with a nice quick game of only 4 hands to gain today's incremental win. (And quite frankly, if it had been any more than that, I likely would have said "frik it" and given up on producing a table today.) The fruits of my labour can be admired below.

October 16, 2024

Starting Bankroll: $2,700.00

Ending Bankroll: $2,800.00

Profit/Loss: $100.00

It's late. Thus, quick commentary! Great night. $100 profit is respectable. Alright, that's it for this one. See you all on the other side!

October 15, 2024

Starting Bankroll: $2,630.00

Ending Bankroll: $2,700.00

Profit/Loss: $70.00

In his seminal book, The Wealth of Nations, Adam Smith introduced us to the invisible hand of the free market. But the cruddy thing about a free market is that it is subject to unscrupulous actors, regulation (too much or too little), and corruption—all of which are variables that can place one's thumb on the scale against the individual. But blackjack? This is a financial system entirely divorced from all other financial systems. Economies may be melting, commodities plummeting, markets imploding—but lady blackjack?—she remains pure; she remains true. And while globalization has spawned this deeply connected financial organism that controls us all, blackjack will always remain external to it, governed only by probability and chance. Here's to $2,500 in profit!—and to the grand ambition that one day, this experiment can diversify all of our financial portfolios!

October 13, 2024

Starting Bankroll: $2,570.00

Ending Bankroll: $2,630.00

Profit/Loss: $60.00

Today, the 21 Fund made $60 while Elon Musk sent the world's most powerful launch vehicle ever developed into orbit where the booster engine returned to the exact position that it was launched from and was captured by the launch tower's giant moving mechanical 'chopsticks'. I'll let you decide which event was the greater feat of human ingenuity.

October 12, 2024

Starting Bankroll: $2,502.50

Ending Bankroll: $2,570.00

Profit/Loss: $67.50

This qualifies as my fastest game on record yet. First hand: boom—Blackjack! Second hand: dealer busts. Not only were we in and out today, but that blackjack also wiped out the remaining 50 cents that has been trailing my bank roll over the past several games. And for anyone who reads this thing consistently, you know how much 50 cents at the end of my bank roll upsets me. Below is my very short and very green table of play for the day.

October 11, 2024

Starting Bankroll: $2,452.50

Ending Bankroll: $2,502.50

Profit/Loss: $50.00

Quick post tonight. I started the session with a high risk double down that went sideways. I feared it would be an omen of a marathon session that would follow. Fortunately, Ganesh smiled on me and eighteen hands later, I walked away with incremental progress achieved. Onwards!

October 10, 2024

Starting Bankroll: $2,402.50

Ending Bankroll: $2,452.50

Profit/Loss: $50.00

So the truth is, I really wanted to hit $2,500 tonight. I kept pushing at that $2,450 wall but she just would not let me through. I get it. That's just the way the cookie crumbles sometimes. Fear not my friends, I will not let that crush my spirit. My heart will go on.

October 9, 2024

Starting Bankroll: $2,350.00

Ending Bankroll: $2,402.50

Profit/Loss: $52.50

Feels good to be kicking butt and capturing data again. Okay, so 50 bones profit may not exactly be the definition of kicking butt—but it is a return to the spirit of where this whole thing began. No big commentary today. I'll let the data table speak for itself. (Okay yes, I did get overzealous on the final hand where I was aiming to triumph with $100 in profit—but at least I was wise enough to walk away when that attempt failed. What can I say? Sometimes you take your shot and it just don't shake your way.) I love you all.

October 7, 2024

Starting Bankroll: $1,000.00

Ending Bankroll: $2,350.00

Profit/Loss: $1,350.00

And we're back. No data tables for the past two sessions. Because things went off the rails. Hundreds of hands played at a highly rapid pace. This was not conducive to data capture. So no data was captured. October 6th saw loss after loss compound on top of itself. I increased bet sizes well beyond the bounds of this experiment. I found myself chasing losses. The anger was searing. I noticed myself laughing—maniacally. I could no longer see the forest from the trees. I had lost my way. And then, commencing today's session with a bank roll cut well in half, I said to myself—frik it. Better we die on our feet than live on our knees, right? So I got to work. Minutes turned into hours. The moon sleepwalked across the night sky. And as the bets flowed hot and heavy, I gradually saw my fortunes begin to turn. One win turned into another that turned into another. And on the seventh consecutive win, I split two 2's against the dealer's 5. On the first 2, I hit a 10. Damn. On the second 2, another 10. Frik me. This was the worst outcome that could have transpired. Two 12's against the dealer's 5. I stayed. The dealer flipped over a 6. 11. My heart sank. The next card was drawn. I knew the outcome before I even looked. The vision of a 10 danced in my head like a nasty little sugar plum fairy. It would soon be all over. But wait—a 4?! A 4?!? The dealer had a 15. I exhaled hard. Could it be—that after two long days—this nightmare could finally come to an end?! The dealer flipped his next card. My heart stopped. It was a 7. BOOYAH! The dealer busted and I logged a double win. Not only had the bank roll been replenished to its original condition, but I walked away $50 up. In one night, I somehow clawed myself, by hook or by crook, to a $1,300+ win. Yes, it was against the spirit of the grander experiment—but I did my job. These past two days saw me deviate from the mandate of the 21 Fund with almost devastating consequences. I had succumbed to the lesser angels of my nature. But I will choose to treat my failures with grace. And the lessons that I have learned from these two sessions will strengthen my resolve as I continue along my righteous path towards Snoopy.

October 6, 2024

Starting Bankroll: $2,300.00

Ending Bankroll: $1,000.00

Profit/Loss: -$1,300.00

Sunday Bloody Sunday.

October 2, 2024

Starting Bankroll: $2,225.50

Ending Bankroll: $2,300.00

Profit/Loss: $75.00

That was a long one. But given the lateness of the hour, this commentary shall be a short one. So look—let's get down to brass tacks here. I could have walked away from this game dozens of hands ago. Was I wrong not to do so? Honestly, I don't know. We'll let the history books decide on that one. My continued play was not unreasonable. But the time expense was immense. I am listening to Suspicious Minds as I write this (skinny Elvis version -- not fat Elvis version). That feels like a metaphor for something. But I'm not sure what. In any event, goodnight all. And in the words of Tiny Tim, that beautiful son of a gun: god bless us, everyone!

October 1, 2024

Starting Bankroll: $2,087.50

Ending Bankroll: $2,225.00

Profit/Loss: $137.50

Here we go, October! And what a way to kick her off. It was a quick game complete with one blackjack and one double down. This pumped up my bankroll significantly. I did not intentionally attempt to profit $135+, but the successful blackjack followed by the successful double down took me there. This also resulted in two great events: 1. I surpassed $2,000 in profit; and 2. I knocked that 50 cents off my bankroll to get me back to an even number. Both these things make me tremendously happy. I am sure it will be a month ahead filled with highs and lows—but man, it's nice to have such a satisfying start!

My September 2024 Month-End Review: The Highs, Lows, and Lessons Learned

September has been a wild ride, full of strategic triumphs, moments of recklessness, and humbling lessons about discipline. As we close the month, here are my reflections:

The Highs

One of the biggest highs was surpassing the $2,000 bankroll mark. This was a significant psychological win for me—proof that the incremental strategy works when followed diligently. The relief of seeing progress in small, consistent steps was immensely rewarding.

Another high point: blackjacks. There were a few well-timed blackjack wins that allowed me to stay afloat during some particularly long and grinding sessions. Nothing feels quite as good as seeing that perfect 21 flash before your eyes. It’s a reminder of why blackjack is so compelling—it can turn around even the toughest hands in a single stroke of luck.

The Lows

The primary low point this month was not financial—it was mental discipline. In particular, September 29th stands out. I allowed myself to be seduced by greed, aiming to cross the $2,000 profit mark in a single session. This was foolish and against the very foundation of my entire experiment. The emotional rush of trying to "be a hero" got the best of me, and I found myself in a dangerous spiral of poor decision-making, wagering too much on the idea of a big win rather than incremental growth.

Another challenging aspect was the introduction of new technology—trying to use ChatGPT’s voice function to log hands. I wanted to streamline the process, but the experiment backfired. I lost entire sessions of data, which, while not a monetary loss, was a loss to my overall strategy and analysis.

And then there were sessions like September 25th—the grind of a long game where the highs were fleeting, and the lows felt unending. I often found myself chasing losses, breaking my own rules about walking away when the bankroll was still up.

Lessons Learned

If there’s one key lesson that crystallized for me in September, it’s this: "Walk away while you’re ahead." It’s the hardest thing to do for anyone gambling or engaging in speculative ventures. The drive to "let it ride" when you’re winning is intoxicating, but it can undo hours—or even weeks—of work in a few reckless hands. Incremental wins add up, and walking away with a small profit or even breaking even is better than risking it all.

Another critical takeaway is the need to respect the "small percentage risk" rule. I deviated from this in moments of bravado and desperation, but blackjack has a funny way of humbling you when you least expect it. I know this intellectually, but September taught me to feel it viscerally.

Lastly, technology isn’t always the magic bullet. Sure, voice tech sounded like a quick fix to streamline hand logging, but it was a stark reminder that experimenting with unproven systems in high-stakes moments (even metaphorically) can lead to unnecessary losses.

Looking Ahead

October is another month—an opportunity to recalibrate. I’ve already learned that incremental progress is what keeps this experiment alive and thriving. The goal is to avoid making grand, ego-driven bets and to stick to a disciplined approach. I won’t let myself fall into the trap of needing one big win to “feel accomplished”—because, at the end of the day, the small wins add up to big ones over time.

So, here’s to the next set of hands—focusing on steady, incremental gains and staying true to the plan. Let’s make October a month of consistency, discipline, and incremental progress.

September 29, 2024

Starting Bankroll: $2,012,50

Ending Bankroll: $2,087.50

Profit/Loss: $75.00

My play today was foolish. The truth is, I was trying to be a hero. Yesterday I surpassed $2,000 in bankroll. Good on me. However, going into today's game, I thought to myself- it's now time to surpass $2,000 in profit, baby (in other words, I was shooting for a $200 win this session). This is actually the antithesis of my whole experiment and I should not have been thinking this way. What has sustained me thus far, and the thing that has differentiated this experiment from how I (and most people) have played blackjack throughout my entire life, is this concept of incremental progress. I get it- this does not sound revolutionary. But the results are so. The hardest thing in the world for a gambler to do is to walk away from a winning game. An immutable aspect of human nature is that when you are winning-whether your game is blackjack, investing, business, relationships-you will want to let it ride. You convince yourself that you are are brilliant and invincible... until you are not. I should have stopped my play today after my first hand. But I allowed myself to fall into this trap- which is particularly dumb given the entire premise of this experiment (...that and only risking a small % of your bankroll on any given hand). I won't lie- things got hairy for a while. I was down significantly. But fortunately, the wave turned and I was able to ride it back to profitability. I'm walking away from this one with what I now think will be a deeply ingrained lesson. Of course I knew this intellectually... but today I also felt it viscerally. Below is the highly stressful gameplay table for today's session.

September 28, 2024

Starting Bankroll: $1,902,50

Ending Bankroll: $2,012.50

Profit/Loss: $110.00

Awesome. This experiment began in earnest almost 2 months ago and I have now surpassed the $2,000 mark. This makes me happy. What makes me less happy is that I used ChatGPT's new voice model tonight to record my hand data. This blew up in my face. It was a very long game (I estimate ~ 75 hands). And I thought ChatGPT and I were on the same page. It turns out, not so much. Those hands that I played are now lost- which is highly disappointing. I will likely need to return to my technique of feeding my rabbit r1 transcriptions into ChatGPT's o1 model. Once I gain a higher degree of confidence in ChatGPT's new voice tool, I will attempt this experiment again. This means (and this upsets me) no gameplay table will be logged again tonight. In other news, I spent much of the day at Ivey, and pledged my allegience to obtain my class ring. It was a great day. So in lieu of my gameplay table, we can all admire a picture of me doing that instead. Xoxo.

September 25, 2024

Starting Bankroll: $1,827.50

Ending Bankroll: $1,902.50

Profit/Loss: $75.00

OpenAI just released their new voice mode, so instead of using my usual method with rabbit r1 to record my data, I decided to test out talking through each blackjack hand directly with ChatGPT on my phone. However, I ran into a challenge: ChatGPT’s verbal responses are a bit too verbose for fast-paced situations. When the game is moving quickly, and hands are coming fast and furious, ChatGPT can still be talking when I’m trying to describe the next hand, which risks losing that data. The voice mode is designed to allow you to interrupt ChatGPT while it's talking, but in practice, that feature worked inconsistently. Eventually, I figured out the right cadence of speech to make it work for my needs. While it wasn’t perfect, the experience of capturing all the data directly within ChatGPT—without needing to first use an external device for data collection and transfer—felt more streamlined. After today’s test, I think I’ve also devised a couple ways to use it more efficiently moving forward. So, this grand experiment of finance and technology shall continue!

September 24, 2024

Starting Bankroll: $1,752.50

Ending Bankroll: $1,827.50

Profit/Loss: $75.00

I am off to Toronto's Art Battle- hence, I was hoping for a quick game. It's great when the universe delivers, isn't it? It has been a grind these past several sessions (including yesterday's where my technology failed me and thus that hand data is lost to the ether forever). My game play, as always (read: mostly), is logged below.

September 23, 2024

Starting Bankroll: $1,655.00

Ending Bankroll: $1,752.50

Profit/Loss: $97.50

Son of a gun. There is no table of my play today. My rabbit r1 had issues. Its processing power could not keep up with my game play for some reason. This left multiple hands unrecorded. Instead of dwelling on it, I kept playing. We came out on top-- cracking the $1,700 barrier. In lieu of the my game play table, I asked ChatGPT to generate a representation of tonight's session. This feels pretty darn accurate.

September 22, 2024

Starting Bankroll: $1,605.00

Ending Bankroll: $1,655.00

Profit/Loss: $50.00

I was hoping for a quick one but today was a grind. Occasionally, when I am taking losses, I'll double up my bet to (ideally) obtain a win that can get myself solidly on track towards even. This strategy has frequently worked for me in the past. Today things went awry. I took a few losses in a row while my bet was doubled up. This compelled me to keep my bet doubled up while I chased those losses. Finally, I broke the back of those terrible cards and got myself back on track. But it was not without first taking a worrisome hit to my bank roll. In the end, we finished on top... in spite of my elevated heart rate. Below is my table of play AND my special "podcast".

September 21, 2024

Starting Bankroll: $1,567.50

Ending Bankroll: $1,605.00

Profit/Loss: $37.50

That was a quickie. After several sessions in which my game extended for too many hands, it is nice to log a quick win on this one. Hitting that blackjack on my final hand also helped to clear out the 50 cents that has been trailing on my bankroll and has been driving my OCD bananas. I'm back in the even numbers, baby. It's also not lost on me that it is the 21st of the month today. Which pleases the part of my soul that wants to believe in gypsies and chi. My very brief play table can be found below.

September 20, 2024

Starting Bankroll: $1,452.50

Ending Bankroll: $1,567.50

Profit/Loss: $115.00

Today was the first day I ever stepped foot inside of a sauna. And what a sauna it was! A friend of mine installed the below in his backyard. We sat there and he poured water on the rocks and I was absolutely certain that all of my skin would burn off. The heat was stifling, the pain was immense, and I didn't think I would make it. And then we cold plunged. After that, we rinsed and repeated for another round and finally ate some sushi. New experiences are cool. Also, tonight's session was cool. Xoxo.

September 19, 2024

Starting Bankroll: $1,452.50

Ending Bankroll: $1,567.50

Profit/Loss: $50.00

Tonight was QFG's 25th Jubilee. It was fun. There were some laughs, some silly dancing, some excessive drinks... and all of that jazz. I'm pretty darned tired though. As such, tonight's commentary shall be brief. I wonder where I'll be when they hit their next Jubilee. Peace and love, everybody.

September 18, 2024

Starting Bankroll: $1,352.50

Ending Bankroll: $1,402.50

Profit/Loss: $50.00

TODAY IS LORNE'S DAAAAAAAAAAAAAAAY (and my mother's). In honour of this auspicious occasion, I dedicated my first hand of the evening to Lorne. If I won, the profit would be sent to him. If I lost, it would be on me. Sadly, I lost. Sometimes, the standard deal (modified) just doesn't go our way, pal. In other news, incremental progress for this session was made. The play table (and an image of Lorne's hand for birthday posterity) are both captured below.

September 16, 2024

Starting Bankroll: $1,312.50

Ending Bankroll: $1,352.50

Profit/Loss: $40.00

Tonight was another ridiculously long game... but not nearly as ridiculous as yesterday's night. Today's session lasted for 47 hands! And while this pales in comparison to yesterday's play, it is still significantly greater than the average number of hands played per game thusfar. All that is to say that it was another grind- but I am still happy enough to walk away with the incremental progress achieved tonight.

September 15, 2024

Starting Bankroll: $1,312.50

Ending Bankroll: $1,312.50

Profit/Loss: $0.00

This may have been the longest game of blackjack I have played in over two decades. It was terrible. From the onset, I took 9 losses in a row. That crud is almost unprecedented. I was stubborn though and refused to take the beat. I kept playing, and playing, and playing. This was not wise. I was down tremendously. I could see this day, this Bloody Sunday, unfolding to my impending annihalation. But by hook or by crook, I clawed myself back to even. Really, I should have never let it get that far. But I was on tilt. I kept making increasingly riskier bets. In the end it paid off to get myself back to even. But I was profoundly lucky. It could have easily gone the other way. Thusfar, this experiment has been wildly successful. However, I have failed to institute appropriate guard rails to protect my downside risk. I still need to figure that crud out- sooner rather than later. For when the improbable days like this one improbably strikes. My marathon session today is documented in the table below.