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Jamie Dimon Drafts Tom Brady...
Uber Bets $1.25B This Time Is Different

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Hey there Folks!
In today’s edition, we’ve got Jamie Dimon deploying Tom Brady to get money from NFL athletes, Uber deciding it’s ready to get hurt again, and Rivian convincing someone other than LIV Golf to send them a check.
Let’s get started…
-“Bro, I just signed a $40M deal.”
“Nice. What’s your plan?”
“…what plan?”
If you’ve spent more than 10 minutes watching ESPN, you’ve heard the stat a million times. Within 2-5 years of retiring, 60% of NBA players and 78% of NFL players go broke (must be the CTE). At this point it might as well be printed on rookie jerseys.
And every time you hear it, same question: How do you make $100M… and end up broke? You’re pulling $20M a year and never think, “maybe I stash $5M somewhere safe and just… leave it alone?” Apparently not.
Well, Jamie Dimon has decided to fix this catastrophe… and shockingly, he’s not doing it out of the kindness of his heart.
It’s called the “Athlete Council,” and instead of tossing a bunch of Harvard grads in quarter zips at the problem, they went and recruited actual legends.
You’ve got Dwyane Wade leading the charge, with Tom Brady (obviously), Sue Bird, Alex Morgan, Megan Rapinoe, A’ja Wilson, and Jalen Brunson now wearing Financial Advisor hats.
According to JPMorgan, they’ve built a full-blown system to help athletes not fumble the bag.
Which feels long overdue… because the current system seems to be: get rich fast, spend faster, trust the wrong people, then act surprised when it all disappears and your circle evaporates with it.
Something tells me a JPMorgan exec went down a late-night YouTube rabbit hole of former stars talking about losing everything and said, “yeah… there’s a business here.”
So now they’re rolling out an “Athlete Center of Excellence”… plus a content hub with guides, checklists, and step-by-step playbooks for everything from NIL deals to building a legit advisory team (which, totally coincidentally, probably points you right back to Daddy Dimon’s guys).
The NIL era changed everything. Now you’ve got 18-year-olds pulling six figures before they can legally rent a car… which means the timeline for bad decisions just got moved up by about 5 years.
So JPMorgan’s trying to get in early… like before the first big check hits and Uncle Leroy pitches his “can’t-miss” investment.
But let’s not kid ourselves… this goes way further than saving athletes from themselves.
This is about locking in a very specific, very lucrative client base.
Because on top of getting paid BIGLY money, today’s athletes are building brands, buying equity, launching businesses, and stacking generational wealth.
And if you’re the bank that gets them early… you’re probably also the bank managing that $100M later.
-By some miracle, Rivian has somehow convinced someone other than LIV Golf’s owners to wire money to their profitless abyss…
Well folks, after 6 long years of FOMO… Uber has officially decided it’s time to get back into the robotaxi business… except this time instead of Waymo, it’s Rivian riding shotgun and a $1.25 billion commitment to give shareholders some hope that this time will be different.
So what are they actually building?
According to the doctored up press release: “up to 50,000 robotaxis based on Rivian’s R2… rolling out across 25 cities globally.”
With San Francisco and Miami getting the first test run in 2028 (which ironically, is still before Rivian expects to be breaking even).
And like every deal that sounds this exciting… the fine print is the only thing that matters.
Uber’s kicking things off with a $300 million investment, which essentially buys them early access to Rivian’s upcoming R2 SUV.
From there, Uber (and its fleet partners) are expected to grab at least 10,000 units, with the option to scale to 50,000 depending on whether Rivian actually hits its milestones… which historically has been more of a suggestion than a guarantee.
And naturally, these robotaxis will live exclusively on Uber’s platform… because as Don Draper once famously said “that’s what the money’s for.”
Now, if this sounds familiar… that’s because Uber has been here before.
Back in 2018-2020, they dumped around $1.8 billion into self-driving… before a fatal incident involving one of their test vehicles forced a full stop.
From there, things unraveled pretty quickly. Testing paused… and eventually, Uber exited the autonomous space altogether.
Now they’re back, this go around hoping they can make it work.
To be fair, Rivian has been busy building out its “this time it’s legit” resume.
They’ve got a $5.8 billion Volkswagen deal, an in-house autonomy stack, a custom chip (RAP1), and enough AI buzzwords layered in to make the whole thing sound convincing.
Plus, they’re taking a YUGE swing on vertical integration… designing the vehicle, software, and computer stack all under one roof… which sounds great until you remember that also means they’re responsible for everything if it goes sideways.
Meanwhile, Uber has been assembling a roster of partners on their end. The list includes Lucid, Zoox, Stellantis, Nvidia… and pretty much every name throwing darts at the entire EV/autonomy ecosystem hoping one of them hits.
Essentially, everyone except Tesla who in their own right is good at making claims… not so good at backing them up.
But hey, maybe Uber’s “partner with everyone” strategy will eventually pay off. But I wouldn’t count on it anytime soon.
The Team at Bullseye Trades
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