Editor’s Note (I’m the editor): What started as a fun exercise, turned into a way deeper newsletter than I expected.
In case you missed it, Jaxson Dart’s season ending knee injury was unfortunately good news for me.

I was certainly in a mental pretzel on Monday Night as one man’s pain (and an entire fanbases too) led to me winning a year’s salary from $100.
I’ve already paid $20,000 in taxes. Fun fact - if you win a bet of 300-1 odds or more and the payout is $5,000+, the sportsbook auto-withholds 24%.
These are lotto rules and it is to prevent those from spending $ that they may not have due to future taxes.
I also donated $5,000 in honor of Magnus Wright to Rachel’s Gift, a charity that helps parents with the loss of their infants.

Today’s newsletter was requested by a reader. He messaged me saying he’d be very interested to know how someone who comes into a large sum of $ overnight plans to use it.
It’s still social media
$80,000 win - $20,000 taxes, -$5,000 donation = $55,000
We are currently at $55,000 remaining.
I’ve written before about how I personally love to gamble. It’s created a lot of positive memories for me and my friends.
I don’t gamble thinking I’m going to win. But I also know that people do and it’s important to not avoid talking about the risks and dangers.
I’m practicing bankroll management and I’ve set aside $5,000 to continue gambling with.
Still, no one also talks about the losses.
Since the big win on Monday night, I’ve lost about $2,800 gambling across CFB and NFL.
In my opinion, it’s important to share these things because there’s stories like this.

If you go through and read about this gentleman’s story. After winning over 6 figures, he gave it all back and more.
He had a real addiction and became suicidal.
Thankfully he found recovery and is using his platform in a great way.
I highly encourage those who are addicted to sports gambling to seek out help.
Total remaining: $50,000
Can’t a man dream
You just won $80,000, surely your mind starts racing to what you can finally buy with all that money.
That’s the point of winning big!
When I was in college, I had a couple friends visiting from out of town.
Before we left for a brunch on a Saturday morning, we discussed what 5 leg parlay could turn our $33 into $1,000.
After we each locked in our picks, we headed to Max’s. Still the greatest french toast I’ve ever eaten. And still unsure how that place didn’t make it in Austin, TX.
Anyways, at that brunch, we discussed what we would do if we won the bet.
We’d rent the penthouse at the 4 seasons for the night!
After quickly checking that price, that would still be out of our combined price range (5 bets of $33/ea for a total of $5,000)
Well, if we won, we’d figure it out anyways.
And as I mentioned above, we have some positive gambling memories, this being one of them.
I can still recite to you what happened that entire day, how each bet won.
We had LSU -6.5. They won 35-28 on this play.

$1,000 to a college kid is honestly the equivalent of $80,000 to a married man with a new daughter.
It will make your year.
The difference though is how that money gets spent.
New clothes, an incredible night out on 6th street and a steak dinner with room to spare.
When you have dependents, you don’t get to dream as much.
But what if I could dream
Life is about having fun right?
So, let’s say I could spend the $60K post tax money.
Here’s what I’d do:
For my wedding, I got a Rolex. My grandfather had a Rolex that appreciated in value (that he probably won gambling). When he passed, my grandmother decided she’d sell it and for our weddings, cut up the Rolex $ into 4 smaller Rolexes (there’s 4 grandsons).
I never realized how much gambling was integrated into my (and my families) life until I was interviewed for the Creator Spotlight.
The best convo I’ve had on Snapback’s history and future
Anyways, the jeweler suggested I get this Rolex Submariner.
He said it’d appreciate in value over time better than anything else in the price range.

I wore it on my wedding day but I never wear it.
I hate jewelry, I don’t even wear my wedding ring.
But I also hate the watch and learned that you should buy what you like not just what will be worth more in the future.
I’ve come to realize I much prefer the Datejust. I think they’re cleaner and more stylish.
I’d probably spend the $10K and never wear it again though.

I’d probably try and add another Lamar Jackson card to my collection.
I have 2 NTA RPAs in 9s but no PSA 10s.
Those are probably $100K cards though so I’d have to find something in the $50K range.

Lamar Jackson is the greatest player, athlete, QB in the history of the sport.
I love him so much. In a future newsletter, I’ll write about why my goal is to never meet him.
Maybe I’d buy a piece of a Bitcoin.
As you saw, I put maybe or I think in front of everything because truthfully, I don’t know because I didn’t have a chance to dream.
How I’m Actually Spending the $50,000
If this reads as a man bogged down with bills, well yeah.
Having a kid is fucking expensive.
I feel tremendous empathy for families who have to consider their financials when it comes to having a kid.
Becoming a father to Rory has truly been the greatest thing to ever happen to me and it is not even close.
So much so, that I’ve found myself over the past 24 hours thinking a lot about the sacrifices of time with her for work.
I’d say last night was the first time ever where I really pondered if it was all worth it.
The hate comments online. The long travel. The risk of running your own business. And all that to miss time with Rory.
By this afternoon, I’ll be back locked in on work more than I ever have been before.
The momentum is palpable. The energy is infectious. I won’t let a stomach bug and long travels drag me down for too long but I think it is also okay to feel for a little.
I’m sorry to ruin all the fun by telling you where that $50,000 is going.
A nanny so I can work more.
Rent so I can put a head over our heads.
Savings for Rory’s college fund (if that’ll even be a thing in 17 years)
Amazon, baby toys, baby clothes.
It’s all for the girls and I wouldn’t have it any either way.
Apologies if you thought this newsletter was going to be fun, but it was written from a place of inspiration.
Inspiration of where the money is really going and where my headspace is at.
I’ll always be transparent here and so thus, that’s what you got.
If you don't want to miss a newsletter, subscribe here





