Jake Castillo
@jakecastilloooo
Founder of Cal AI
154 Following 7.7K Followers
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The Cal AI story is closer to 5,000 words per chapter.
I've spent 6 weeks turning what we built into single-paragraph posts. There's another 50,000 words I haven't gotten to yet.
Launching a weekly newsletter for the long version: The Operator's Notebook.
Free. 5-minute read. Subscribe here:
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This launch video has so many layers to it 😂
Before Cal AI, I would’ve driven 20 minutes across town to let someone “pick my brain” for a free lunch.
Now I do the math.
One hour of my time is worth $1,000 in consulting.
Unless that lunch costs more than $1,000, I’m losing money
Free lunch is only free when your time is worth nothing.
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A book made me think about Cal AI for a week.
Tomorrow, and Tomorrow, and Tomorrow is about two friends who build a video game together and become famous in their twenties.
But really, it’s about the bond you form when you build something that actually works.
Cal AI might be our last big win.
It might be the first of many.
But it will always be the first.
Some things money can buy.
That feeling isn't one of them.
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The Cal AI/MFP deal closed back in December.
But we didn’t announce it publicly until March.
For months, I had to keep the biggest news of my life entirely to myself.
That was one of the hardest stretches of the entire journey.
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Hormozi just announced his first marketing workshop.
Most people see one announcement but it's really just the third step in a 9-month play.
Step 1 - Last August: Free virtual training. Millions showed up.
Step 2 - Same weekend: $29 book. $106M in revenue.
Step 3 - This week: Workshop announced.
Each step buys attention for the next.
Most founders jump straight to step 3
Attention compounds. Monetization waits its turn.
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One of the hardest pricing calls we got right at Cal AI:
Launching without a free trial.
Standard B2C advice says reduce friction. Let users try first. Prove the value later.
We did the opposite.
Hard paywall from day one.
The lesson: free trials aren’t always a conversion tool. Sometimes they’re a crutch for weak messaging.
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Hardest day of the 18 months was Thanksgiving 2024.
We’d spent the whole week building toward a viral promo.
We thought it was going to be a game changer.
Thanksgiving Day, it dropped.
Nothing.
No spike.
No conversion boost.
No significant movement on the charts.
At the time, it felt like a disaster.
Looking back, it was probably a good sign.
If every bet works, your bets are too small.
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Last Thanksgiving, I was upstairs grinding through due diligence.
Everyone else was downstairs.
Games. Movies. Dinner.
No one complained.
Every hour or so, someone came up and asked if I needed food or water.
Then they went back downstairs.
That was most of the last 18 months.
Me working.
Everyone else putting up with it.
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Drake dropped Iceman this week.
Half the internet hates it. Half can't stop posting about it.
That's the win.
Attention is the asset. Whether they love you or hate you matters less than whether they're talking.
The most valuable skill in 2026 is the ability to put yourself in the conversation.
Everything else is downstream.
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Cal AI’s first $1,000 of revenue felt like everything.
Shortly after, we set a new goal: $10,000/month.
I thought that would mean we’d made it.
Blake gave me a wake-up call:
“No time to celebrate. Now it’s a race against time.”
He was right.
Early traction doesn’t mean you won.
It means the clock started.
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The slow yes is the wrong yes.
If I can't tell within 20 seconds whether a creator will convert, the answer is no.
Every time I went back and forth, asked the team, and said yes anyway, it was almost always a mistake.
Influencer evaluation isn’t a spreadsheet.
It’s taste.
I can’t perfectly explain what makes a creator great.
But I know it when I see it.
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Comedy creators have the biggest audiences and some of the worst ROI.
The audience is broad, passive, and algorithm-dependent.
No cult following. No deep trust. No “I want to be like this person.”
Influencer ROI comes from belief, not reach.
Comedy sells attention, not conversion.
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I thought I had bad attention to detail.
Turns out, I just didn’t care enough.
In consulting, my peers would redo my work and find things I missed.
Then Cal AI came along.
For the first time, I was working on something I actually cared about.
Suddenly, I caught everything.
My brain didn’t change.
The work did.
Most people don’t have an effort problem.
They have an ownership problem.
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One hiring requirement we had at Cal AI:
First-principles thinking.
We didn’t need people who made simple problems sound complex.
We needed people who could make complex problems simple.
Strip away the noise.
Find the core constraint.
Solve that.
In startups, the simplest solution is usually the right one.
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Cal AI's stack is almost 100% built with in-house tools.
No serious off-the-shelf tools. If we needed something, we built it.
Every dollar of dependency was a dollar of slowdown.
Every "we'll wait for X to ship Y" was a chunk of a quarter we couldn't get back.
No one was working as hard as us.
No one needed to. We just couldn't afford to wait.
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One of the worst creator deals we lost money on: UFC fighters.
The math seemed obvious. They cut weight. Track macros. Live by the calorie. Right?
Wrong.
Their audience drinks beer and eats pizza watching them fight.
The fighter tracks calories. The fan tracks the fight.
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First business I ran was hydrogen water bottles.
Best month: $10,000 in revenue.
Killed by my own risk aversion.
Competitors were spending $50, $60 CPMs to scale fast.
I was at $20 because I needed the math to make sense.
They scaled. I didn't.
Speed is a price you pay before you find out if it works.
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I'm getting married on June 16 in Lisbon, Portugal.
Everyone at the wedding has been on the journey from day one.
Mom. Brother. Mollie. The Cal AI team. The friends who believed before there was anything to believe in.
The wedding wouldn't have been possible without Cal AI.
Neither would I
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@LifeOfPhat Learned everything from @blakeandersonw
