Justin Caballero

Building the #1 home remodeling company in Florida. Ole Miss alum.

[Guillermo Flor @guilleflorvs]

Sequoia's thesis that the next $1T company will sell work, not software, is the most important reframe in AI right now.

The argument: if you sell a copilot, you're competing with every new model release. But if you sell the outcome — books closed, contracts reviewed, claims handled — every AI improvement makes your margins better, not your product obsolete.

The key insight most people miss: for every $1 spent on software, ~$6 is spent on services.

The entire SaaS playbook was about capturing the software dollar. The AI playbook is about capturing the services dollar — at software margins.

Not "AI for accountants." The AI accounting firm.
Not "AI for lawyers." The AI law firm.

The companies that figure this out won't look like SaaS companies. They'll look like services firms rebuilt on software infrastructure.

That's a fundamentally different company to build, fund, and scale. And most founders are still building copilots.

[Justin Caballero @JustinCab]

@MichaelBorkey Legendary!!!

[Dave Portnoy @stoolpresidente]

Congrats to Ole Miss. Great game. Makes you wonder why Lane thinks you can’t win big at Ole Miss.

[Keith Carter @KeithCarterOM]

Let’s go! No one better @CoachGolding! Excited for the next few weeks and for the future of @OleMissFB. Players and staff ready to go win a natty! #CFP

[Barstool Sports @barstoolsports]

“I think it’s my number one campus I’ve been to” -@stoolpresidente on Ole Miss

@BarstoolPickEm presented by @Draftkings #DKPartner

[Justin Caballero @JustinCab]

@hey_madni What was brutal about these?

[Justin Caballero @JustinCab]

@elonmusk I’m O

[Inky Johnson @inkyjohnson]

Be grateful for the problems

[Hasbulla @Hasbulla]

Gm💎⛓️

@Lane_Kiffin and @OleMissFB want me to come to a game?

Who would come with me?

[Elon Musk @elonmusk]

My pronouns are Prosecute/Fauci

[Justin Caballero @JustinCab]

@MichaelBorkey Wouldn’t it be financially irresponsible to NOT pay Kiffin more in order to keep him in Oxford. There has to be a very quantifiable ROI. He’s already top 10 paid and the gap to the top 3 is just a few million per year. Surely increased revenue offsets an investment of that size!

[Elon Musk @elonmusk]

Entering Twitter HQ – let that sink in!

[Elon Musk @elonmusk]

@wholemars Yeah, but I didn’t leak it to NYT. They must have got it through friends of friends.

I heard from multiple people at TED that Gates still had half billion short against Tesla, which is why I asked him, so it’s not exactly top secret.

[Whole Mars Catalog @wholemars]

So apparently Bill Gates hit up @elonmusk to discuss “philanthropy on climate change” but Elon asked if he still had a half billion dollar short position on $TSLA.

Bill said he hasn’t closed it out, so Elon told him to get lost. No idea if this is true lol

[Lane Kiffin @Lane_Kiffin]

⁦@YogaWorks⁩ ❤️

[Justin Caballero @JustinCab]

Focused on continuous growth and expansion in all facets of my life and business. There are always opportunities.

[Justin Caballero @JustinCab]

Setting the intention to not let any negative external forces impact my internal well being. Wishing the same for all of you in this time of uncertainty and change right now!

[Joey Burrow @JoeyB]

Considering retirement after I was informed the football will be slipping out of my tiny hands. Please keep me in your thoughts.

[Justin Caballero @JustinCab]

@garyvee what text messaging are you using?

[Justin Caballero @JustinCab]

Most people will choose unhappiness over uncertainty