Good morning!

It’s been a bit since the last newsletter, but I found our new rhythm.

I just had one of those moments where everything clicked. I found this agent, Juan, who, instead of cold calling during COVID, grabbed a GoPro and started driving Uber around Tampa Bay to create content. Talk about zigging when others zag.

In today's newsletter:

• How a "naturally boring" agent built a YouTube empire ($85M/year)

• The local newsletter making $320K in a small town

• Fresh YouTube ideas that are crushing it right now (even non real estate)

• Rapid fire for your consumption: fresh insights from Shopify's CEO, Diary of a CEO's thumbnail evolution, and why Perplexity Pro might be your new Google

Fun fact: Juan reads 20-30 publications every morning to stay sharp. And here I was feeling accomplished with my morning coffee.

Let's dive in.

— Andrew

P.S. First time here? This newsletter is where we break down what's actually working in modern marketing, minus the fluff. Would love to hear your thoughts on today's stories!

Playbook

Juan Alcala had a decision to make.

91 days had passed since the pandemic started, and he still hadn’t made a single dollar. His wife looked at him and said exactly what he needed to hear: "You have a license. You need to get your behind to work."

But instead of cold calling or door knocking, Juan did something different.

He grabbed his GoPro, signed up to drive Uber, and spent the next three months exploring Tampa Bay, stopping at every interesting spot to film content.

Today, that decision has turned into a media empire with:

• 285 self-scheduled buyer/seller consultations per year

• 17.6K YouTube subscribers

• A 9-person production team

• Operations across two states

• $36K foreclosures that became million dollar listings

And here's the cherry on top: He did it all while being "naturally boring" (his words, not mine).

The Failed Teacher Who Found His Calling

Juan's journey didn't start in real estate. He originally went to school to be a teacher but left because he “Was never going to make any money there."

After pivoting to the beer industry, where he got his first taste of marketing by wining and dining brewery executives, Juan got his real estate license in 2012.

His first sale? A $36,000 turnkey foreclosure in Detroit that netted him $800 after splits.

"I was reading Buffett at the time," Juan recalls, "and he was like 'Hey, whenever people are running away it's a time to get in.' I was so ignorant, I was like 'that sounds like a great idea!'"

That "ignorance" would later prove to be his superpower.

A Pivot That Changed Everything

By 2018, Juan had built enough of a business in Michigan to attempt semi-retirement in Florida.

Then COVID hit. Michigan deemed real estate non-essential, and Juan's income dried up completely.

That's when he made the decision that would change everything: Instead of fighting the old game, he'd create a new one.

Juan’s $85M/YR YouTube Formula

Juan's content strategy breaks down into three tiers of exponential returns:

1. Reality Check Content

   • 50-75x normal views (80k-200k views)

   • Example: "What They're NOT Telling You About Moving to Florida"

   • Keys: Raw honesty, pattern interrupts, hidden truths

2. Cost Analysis Content

   • 15-25x normal views (30k-50k views)

   • Example: "The Real Cost of Living in Tampa"

   • Keys: Specific numbers, real examples, clear comparisons

3. Area/Neighborhood Deep Dives

   • 10x normal views (20k-40k views)

   • Example: "Living in Clearwater Beach Florida"

   • Keys: Personal experience, local insights, lifestyle focus

For Juan, every piece of content has to answer a specific search intent. Most agents create content they want to make, but he creates content people are already searching for.

His video planning process starts with three questions:

1. What are people actually searching for about Tampa?

2. What misconceptions need to be corrected?

3. What information would I want if I were moving here?

Be willing to answer them, and you got yourself an audience of possible leads that know you’re the best at tackling their questions.

The Anti-Marketing Marketing

While most agents focus on pushing out content, Juan follows a different philosophy.

"YouTube doesn't push videos," he explains. "YouTube pulls videos for the viewer."

This means:

• No generic "how to buy a home" real estate content

• No basic property tours

• No market update spam

• No spamming other platforms to drive to YouTube

Instead, he focuses on being the unofficial guide to Tampa Bay life, answering the questions people are actually searching for.

"I literally jumped in an Uber for three months. What I would do is I would get to a new place, I would Google it on my phone, and I would literally jump out with my GoPro.”

This way, Juan was able to familiarize himself with the things that actually make his area desirable. He doesn’t market a picture-perfect landscape, he just offers an honest look.

The Content Machine

But how exactly is he able to fully implement this strategy? 

The answer is simple — He’s not alone. Juan's operation now includes:

• 4 agents across two states

• 9-person production team

• Copywriter for content planning

• Regular content planning sessions

But it's not just about the team size. Juan has built a systematic approach to content creation that keeps the machine running smoothly. FYI, His morning routine starts with reading 20-30 different publications to stay current on market trends and content ideas.

Most agents try to wing it with content, but Juan built a machine that can consistently produce what his audience wants.

The key? Actually working on his packaging. Every piece of content goes through the process of thumbnail design, hook crafting, and story structuring before it ever sees the light of day.

The Hook Evolution

Let’s focus on those intimidating hooks for once: Juan’s journey to mastering YouTube hooks didn’t happen overnight, and he’s aware of this.

His early videos started with very basic introductions: "Hey guys, today we're talking about Tampa versus Orlando."

The results? Decent, but not spectacular. 

Everything changed when he discovered a fundamental truth. You have about 30 seconds to convince someone their next 15 minutes belong to you.

“Top performers know the path: Get them to watch, keep them watching, make the offer. Everything else is noise."

Juan’s hook structure evolved into a three-part formula:

• Pattern Interrupt: Start with an unexpected statement

• Curiosity Gap: Hint at valuable information that’s being withheld

• Credibility Marker: Establish why viewers should trust you

That’s why his most successful hooks now follow a dream-to-nightmare-to-solution pattern:

1. Paint the Florida dream (sundrenched beaches, perfect lifestyle)

2. Introduce the hidden reality (what most people don't see coming)

3. Promise the roadmap (how to navigate the challenges)

The Numbers Behind Authentic Content

The results speak for themselves:

• 285 Zoom calls scheduled by prospects (not by him)

• 17.6K subscribers and growing

• 75% higher retention than industry average

• Content performing up to 75x above baseline

But perhaps most importantly, Juan hasn’t been forced to do any prospecting-based business in five years since he built an attraction marketing machine.

Of course, none of this happened overnight. Juan has a specific approach to YouTube, and it’s the whole reason behind his success.

By focusing on searchable, evergreen content, each video keeps on generating leads months and even years after being published.

Want some ideas? Here’s the content that actually pulls:

Short-Term Ambitious, Long-Term Lazy

If there’s anything that stood out while talking to Juan, it’s got to be the philosophy he lives by.

"My whole goal in life is to be short-term ambitious so I can be long-term lazy.", Juan says.

By that, he means putting in the hard work upfront to create content that continues to grow indefinitely. While other agents are constantly chasing their next lead, Juan created a search-driven, evergreen content library that acts as a 24/7 lead generation machine. 

In order to achieve that, he has to make sure every single video is able to pull the viewer in — and he also happens to have a system for this.

Professional marketers understand something that most agents don't: You want to work at the top of the funnel, not the bottom. When you build the right content machine, the leads come to you.

The Lesson for Every Agent

The biggest lesson I learned from Juan isn't about YouTube tactics or content strategies.

It's about having the courage to play a completely different game.

"When you understand that you don't have to chase the bottom of the funnel, but can focus on the top — that's when everything changes in real estate marketing."

Because real estate isn't about following the crowd. While others chase immediate leads, Juan built a content empire.

While others focused on pushing content to their audience, Juan mastered the art of pulling viewers in

It’s all about taking that leap — or, in Juan’s case, grabbing that GoPro.

Want to dive deeper into Juan's content strategy? Watch the full conversation to get his complete playbook.