STRATEGIC SCALE PODCAST

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 ...

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...

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...

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...

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...

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...

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...

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...

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...

This week’s been all about operationalizing what we’ve been building behind the scenes…

From team shifts and campaign revamps…

…to locking in high-leverage partnerships and content systems.

Let’s Get 2 It!

Strategic Planning & Ops

• Kicked off the week with our monthly strategic planning call w
...

Here’s what happened inside the business this week…

The real numbers, systems, breakthroughs, and breakdowns on the path to building a billion-dollar portfolio.

My #1 Rule for Negotiation (That Most Ignore)

This week, I was finalizing a deal with a new portfolio partner.

As we wrapped terms, it ...

If Week 1 of this newsletter was the high…

And Week 2 was the “I almost quit” moment…

Week 3 was the full entrepreneurial rollercoaster in real-time.

From backend breakdowns to big breakthroughs, here’s what happened this week in the journey toward my first billion.

Monday – Maestro Mode + Strat...