The Outsider

3 Wise Years of "The Outsider"

In partnership with

THE SIGNAL:

This is our first article of 2026 — the Year of the Horse.

I started writing this newsletter on the first Wednesday of 2023. I was still a Realtor at KW. The first drafts were sent through good old Command and landed in about 82 inboxes.

The idea came straight from the pages of the MREA- a real estate book. The moment I read about a writing a newsletter, my brain lit up — fireworks. No hesitation. I knew immediately this was it.

Me: the Carrie Bradshaw of Real Estate!

The name arrived just as fast. I was reading The Outsider (L’Étranger) by Camus at the time. An absurd voice of someone who stayed a forever stranger to himself and everyone around him.

Three years later, our readership has grown exponentially. But more importantly, the quality of that readership has deepened. This is not a passive audience. This is an engaged, curious, discerning one. Elite names of business and art tuning in weekly.

Along the way, we created characters.
We told stories.
We learned about each other’s businesses.
We applied what we learned in real estate school — and what we learned by living, by trying and striving.

What started as a “newsletter” became something else entirely.

My business is Real Estate Entertainment.
And my job is to entertain you all the way to success.

My name is Filipa and it means lover of horses.
And if there’s anything I’ve learned, it’s that horses don’t move cautiously. They move with force, instinct, and forward momentum. They carry people across terrain they could never cross alone.

So if this is the Year of the Horse, consider this your invitation to move — boldly, faithfully, and without apology.

Together, we ride.

ARTIFICIAL INTELLIGENCE
🌎 AI in my Business

AI Integration is a big part of my work flow these days. It has become a constant companion, board of advisor, assistant and anything in between. From goal setting, to writing, to organizing, budgeting, troubleshooting, to image and text creation: a lot of the work I share has been a collaboration with Technology as I understand it and afford it.

I have a few projects to share in 2026 with the aid of AI, so hang tight :)

CHARACTER BUILDING
REGINA.

Regina Young is NOT a realtor — she is THE Realtor.

America’s favorite Realtor.

She moves through property the way others move through power. Listings are not square footage to her; they are psychology, timing, leverage, and narrative. She understands that every transaction is emotional before it is financial, and that every deal reveals more about a person than they intend to show.

Regina was born inside the market. She learned early that real estate is not about houses — it’s about decisions under pressure. Who hesitates. Who postures. Who knows their numbers. Who falls in love too fast. Who walks away clean.

As a character, Regina embodies the disciplined instincts of a top-producing agent: database mastery, long memory, impeccable follow-up, and an unshakable sense of value. She knows when to push, when to pause, and when silence closes the deal.

The Dream Catcher System (DCS) is her operating manual.
Nine steps forged from real estate logic and life application: vision, underwriting, action, leverage, patience, and exit. The same principles that turn first-time buyers into investors and chaos into cash flow are repurposed to help people build careers, relationships, and self-trust.

Regina doesn’t sell fantasies. She sells clarity.
She doesn’t promise comfort. She promises movement.

This is real estate as education.
Story as strategy.
Entertainment that leaves you wealthier than it found you.

SCRIPTING, LEARNING SYSTEMS & THE PURSUIT OF YOURSELF

The Dream Catcher System

The Dream Catcher System is an original invention. Based on ideas from Gary Keller, Brain Tracy & Greek Tragedy.
It’s a storytelling system.

I discovered there is no real difference between goal-setting systems, business plans, and scripts written for actors. They are all text-to-action commands. The only difference is that one of them is exponentially more fun.

That realization changed everything.

I became a Method Realtor. I teach complex real estate concepts through entertainment. I don’t rehearse affirmations — I rehearse scenes. I don’t chase goals — I write roles that require me to become the person who achieves them.

I act my way into my goals.
Not as myself, but through characters. Through dialogue. Through narrative.

And it turns out —
the world can’t tell the difference.

CREATIVITY & BUSINESS

The biggest goal for my Business in 2026 is Beauty.

Joan Crawford:
“I think that if I were asked what I always wanted, I would say beauty.”

*Star 86 - THE YEAR OF REGINA

Momentum matters. Systems matter. Repetition matters. Regina was built to operate under those conditions — steady, deliberate, impossible to rush and just as difficult to derail. The Dream Catcher System exists for the same reason: to turn intention into executable movement and imagination into repeatable outcomes.

House.Roc Entertainment, The Outsider, House.Roc Magazine SchoolHouse.Roc, and MeeTV are not separate projects.
They are branches of the same tree — a How to Make It in America unfolding in real time.

Different formats. One system. One trajectory.
Built publicly. Executed privately. Compounding over time.

Nothing to hide.
This work lives across multiple channels. Subscribe to all of them for the complete picture, or follow the ones that speak to you.

This year isn’t about proving anything. About showing up, applying pressure in the right places, and letting time do the rest.

If you’re reading this, the work has already started.
Stay in stride.

Are you tuning in?

Media Leaders on AI: Insights from Disney, ESPN, Forrester Research

The explosion of visual content is almost unbelievable, and creative, marketing, and ad teams are struggling to keep up. Content workflows are slowing down, and teams can't find the right assets quickly enough.

The crucial question is: How can you still win with the influx of content and keep pace with demand?

Find out on Jan 14, 2026, at 10am PT/1pm ET as industry leaders—including Phyllis Davidson, VP Principal Analyst at Forrester Research, and former media executive Oke Okaro as they draw on their deep media research and experience from ESPN, Disney, Reuters, and beyond.

  • The forces reshaping content operations

  • Where current systems are falling short

  • How leading organizations are using multimodal AI to extend their platforms

  • What deeper image and video understanding unlocks for monetization

Get clear insight and actionable perspective from the leaders who built and transformed top media and entertainment organizations.

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