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[#017] My First Billion: The Week You Don't See Coming my first billion Feb 21, 2026

There's a version of this journey that looks like big announcements every week.

New launches. Massive wins. Clean, linear progress.

This wasn't that week.

And honestly, I think this week was more important because of it.

We kicked off Monday with me making a call I didn't expect to make…

I resc...

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[#016] My First Billion: Recalibration Season my first billion Feb 13, 2026

If I had to describe this week in one word, it would be:

Recalibration.

Monday started with my monthly CEO Update, the internal letter I send to our team at Strategic Scale Institute monthly.

Jim Collins once said:

“Building a visionary company requires 1% vision and 99% alignment. When you have...

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[#015] My First Billion: The Cost of Bad Momentum my first billion Feb 06, 2026

This week wasn’t about pushing harder.

It was about stopping long enough to fix the right problem.

Last month, I paused all ads and cancelled all virtual events we had planned.

Not because demand is low, but because quality was off.

We’ve been great at generating leads.
The data made it clear we ...

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[#014] My First Billion: After the Win Comes the Work my first billion Jan 30, 2026

By the time you’re reading this, we’ve just wrapped the first iteration of the Strategic Scale Summit.

Despite weather warnings, travel concerns, and all the usual friction that comes with something new…

It was well attended, high quality, and exactly what it needed to be.

 

Monday, my business ...

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[013] - My First Billion: Raising the Floor my first billion Jan 22, 2026

By the time you’re reading this, I’ll be in the middle of Strategic Scale Summit.

People are flying in. The room is set.
The work is underway.

But the real work for me happened before the event.

Last week, we wrapped up one of our 3-day virtual bootcamps and to be blunt, it bombed.

Not in a dr...

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[#012] My First Billion: 13 Years In my first billion Jan 15, 2026

Today marks 13 years since I officially filed the paperwork for my first company.

January 16, 2013.

I remember it clearly.

I was driving a 1994 Chevy Lumina.
We didn’t want to pay for parking, so my wife pulled up to the curb.

I ran inside, filed the paperwork, and ran back out.

I had just enoug...

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[#011] My First Billion: Alignment Beats Effort my first billion Jan 12, 2026

This week wasn’t loud.

It was clarifying.

Rewiring the Way I Think About Scale

I’ve still been reading How to Make a Few Billion Dollars by Brad Jacobs.

Early in the book, he talks about rearranging your brain, specifically how certain cognitive distortions quietly limit scale long before strate...

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[#010] My First Billion: When the Business Gets Boring (In a Good Way) my first billion Jan 02, 2026

It’s January 2nd, A new year.

I got back in the office on Saturday after being fully unplugged in Panama with my family for a week.

No work. No dashboards. No meetings.

That part matters.

And when I returned, there wasn’t a pile of things waiting on me.

No fires.
No backlog.
No sense of “I need...

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[#009] My First Billion: Strategically Absent my first billion Dec 28, 2025

By the time you’re reading this, I’ll be out of the country with my family for Christmas.

No meetings.
No content days.
No dashboards.

About five or six years ago, we started a tradition of bringing in Christmas in a different country each year.

This year, we’re in Panama.

I remember the first tim...

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[#008] My First Billion: When Signal Replaces Effort my first billion Dec 19, 2025

This week felt full, but not heavy.

There were workouts, CFO conversations, tax strategy execution, sales leadership syncs, content planning, client delivery, ad management, hiring decisions, and prep for vacation and what’s coming next.

A few years ago, a week like this would’ve felt chaotic. Now...

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[#007] My First Billion: Outgrowing Toxic Momentum my first billion Dec 15, 2025

This week started with something “small” that will matter more than most people realize.

Based on team feedback, I decided we’re changing our CEO Update from weekly to monthly.

Not because there’s less happening, if anything, there’s more, but because the company has reached a point where signal m...

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[#006] My First Billion: Disappointment, Detours & Destiny my first billion Dec 08, 2025

This week was filled with pivots, fresh wins, and some powerful reminders about growth, leadership, and alignment.

Let’s break it down

MONDAY & TUESDAY: Field Trip, Frustration & Flow

I started the week driving down to Jekyll Island for a two-day overnight field trip with my 11-year-old, Royal (a...

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