Welcome back to The Rewind Report, where we turn pop culture obsessions into profit strategies. This week we're diving into why most side hustles die in Season 1 like everyone in Squid Game—and how the survivors completely change the game by Season 3.

What's Inside This Issue

• 🧠 THE REWIND RUNDOWN

  • Why Your Side Hustle Needs to Survive Its Squid Game

• 💰 QUICK WIN OF THE WEEK

  • The Netflix Problem Every Wealth Builder Faces

• 🏢 MARKET SPOTLIGHT

  • Why Dallas Multifamily Is the Boring Investment That Actually Works

• 🛠️ TOOL STACK DEEP DIVE

  • The Micro Revolution Nobody Talks About

• 🧠 MINDSET CHECK

  • Why Perfection Kills More Dreams Than Fear

  • The Takeaway

🧠 THE REWIND RUNDOWN

Why Your Side Hustle Needs to Survive Its Squid Game

I spent two years in real estate making exactly $0. Not because I wasn't working—I was grinding myself into the ground. I was the contestant who got eliminated in Round 1 because I thought I could outsmart the game instead of just playing it.

Here's the thing that still makes me cringe: I was talking to people who honestly didn't seem as smart as me, but they were way more successful with real estate than I was.

That's when the real torture started—not just the cold calling (though I literally got sick to my stomach thinking about dialing), but the deeper question: Am I actually gonna make it? Do I have the stuff to get this done?

It was like going 0-for-30 in baseball. You start questioning whether you've lost it entirely.

The cold calling was brutal, but not for the reason you'd think. I don't mind talking to people.

It's the monotony of dialing, the people yelling at you, and wanting to yell back when they're rude—which doesn't exactly work for your profit margins or blood pressure.

It reminded me of my Hollywood production assistant days, where you think you're going to work on films but you're really just a glorified gopher getting donuts and running paperwork across the studio. The soul-crushing part is knowing you're not worth much.

Then my mentor hit me with reality: "Stop trying to make everything perfect. Get the deal in, then use that money to hire other people to make the system you actually want."

That's when I discovered the Squid Game secret to side hustle survival. The contestants who make it to the final rounds aren't the ones who work hardest—they're the ones who understand the game has changed.

My game-changer? Semi-automation. AI finds the leads, humans dial them for $4-5/hour. Now I check metrics instead of making calls. If something doesn't sell within a week, it's not gonna sell ever. Simple. Effective. No more stomach knots.

Your side hustle's Season 3 is when automation takes over the mundane so you can focus on strategy. Most people get eliminated because they're still playing by Season 1 rules—perfection over progress, manual over automated, working IN the business instead of ON it.

Your move: 1) Identify your most soul-crushing repetitive task and find an AI tool to automate it. 2) Ask AI to challenge your assumptions about what you "have to" do manually. The players who survive aren't the smartest—they're the ones who adapt fastest.

Speaking of adaptation, here's the automation shift that's quietly revolutionizing how smart money finds opportunities...

💰 QUICK WIN OF THE WEEK

The Netflix Problem Every Wealth Builder Faces

You know that feeling when Netflix serves up the perfect show you didn't even know you wanted? You weren't searching for it, but there it was—Squid Game, Peaky Blinders, Bridgerton, Baby Reindeer, Strangers Things, One Piece, whatever your latest obsession. The algorithm did the hunting for you.

Most wealth builders are still stuck in the Blockbuster era.

They're out there cold calling everyone, networking at every event, manually hunting for opportunities like it's 1999. Meanwhile, the smart money has flipped the script entirely. Instead of chasing opportunities, they've built systems where opportunities find them.

Think about how TikTok shopping works. You're not browsing for a $47 gadget that organizes your junk drawer, but suddenly you're watching a 30-second video thinking, "Holy shit, I need that." The algorithm figured out what you wanted before you did.

That's exactly what successful real estate investors and online entrepreneurs are doing now. They're not making 100 cold calls a day—they're using AI to identify motivated sellers, automated email sequences to nurture leads, and content systems that attract qualified prospects.

I learned this the hard way during my $0 years. I was manually dialing through lists like some kind of telemarketing masochist, when I should have been building systems that work while I sleep.

The Netflix approach to wealth building: Stop searching, start serving. Create content that solves problems. Build automated lead magnets. Let AI handle the initial qualification. Position yourself where your ideal opportunities scroll past you, not the other way around.

Worth exploring: What if you spent this week setting up one automated system instead of manually chasing ten prospects? Pick one repetitive task—lead generation, initial outreach, or follow-up—and automate it. Your future self will thank you when qualified opportunities start appearing in your inbox instead of you hunting them down.

The best opportunities rarely come from desperate searching. They come from smart positioning.

And when it comes to smart positioning, some of the best opportunities are hiding in plain sight in the most boring places...

🏢 MARKET SPOTLIGHT

Why Dallas Multifamily Is the Boring Investment That Actually Works

While everyone's chasing the sexy markets, Dallas is quietly crushing it. 103,983 multifamily units financed since January 2024—more than any other market in the country, according to CRED iQ data.

No Instagram-worthy beaches. No tech bros driving up prices. Just solid fundamentals doing what solid fundamentals do: making money.

Here's why Dallas keeps winning while flashier markets struggle:

Population growth that actually matters. People aren't moving to Dallas for the lifestyle—they're moving for jobs, affordable housing, and opportunity. That's sustainable demand, not speculative hype.

Rental rates people can afford. Unlike coastal markets where a one-bedroom costs $4,000, Dallas keeps rents reasonable enough that people can actually pay them. Revolutionary concept, I know.

Business-friendly policies. No rent control. Reasonable regulations. A state government that doesn't actively hate landlords. Sometimes boring is beautiful.

I've seen too many investors get seduced by markets with "potential" and "growth stories." Meanwhile, Dallas investors are collecting checks from properties that cash flow from day one.

The fundamentals are almost embarrassingly simple: growing job market, reasonable construction costs, and a population that needs places to live. It's not going to make you sound cool at real estate meetups, but it will make you money.

The lesson? Sometimes the best investments are the ones that make you yawn. While everyone else is hunting for the next Austin or Miami, Dallas is sitting there delivering 7-8% returns like clockwork.

Worth considering: What if the market everyone's ignoring is the one actually worth your money?

This same principle applies to the tools successful entrepreneurs are using while everyone else chases the latest AI hype...

🛠️ TOOL STACK DEEP DIVE

The Micro Revolution Nobody Talks About

While everyone's arguing about which general AI is best, smart money is investing in specialized AI tools that cost more but deliver exponentially higher ROI.

Here's the counterintuitive truth: The most expensive AI tools are often the cheapest per result.

Take BatchRank AI for real estate lead scoring. It costs more than a ChatGPT subscription, but it saves me 15 hours a week and increases my conversion rate by 40%. That $97/month pays for itself in the first qualified lead it identifies.

Most specialized AI tools are built on ChatGPT's API, but they've done the hard work for you—custom training, perfect prompts, industry-specific optimization. You're paying for expertise, not just access.

The micro AI advantage:

• Lead scoring tools that know your market better than you do

• Email automation that writes like you, not like a robot

• Price optimization that adjusts based on 1,000+ market variables

• Document analysis that finds details human eyes miss

I learned this the hard way. Spent months trying to prompt ChatGPT for real estate analysis. Cost me nothing per month, cost me everything in time and missed opportunities.

Then I switched to purpose-built tools. Higher monthly cost, but they transformed my entire business in weeks, not months.

The lesson? Stop thinking about cost per month. Start thinking about value per result.

Worth exploring: What specific problem costs you the most time each week? Search for AI tools built specifically for that problem. The subscription might sting, but the ROI will shock you.

Sometimes paying more upfront means earning exponentially more long-term.

But here's the thing that trips up even smart tool buyers—the mindset trap that kills more businesses than bad software ever could...

🧠 MINDSET CHECK

Why Perfection Kills More Dreams Than Fear

I made exactly $0 in real estate for two years. Not because I was scared. Not because I didn't work hard. Because I was trying to make everything perfect before I started.

Perfection is the enemy of progress—and profit.

Here's what perfection looked like for me: Researching every possible lead source for months. Building the "perfect" spreadsheet system.

Waiting until I understood every market nuance before making my first call.

Meanwhile, other investors—who honestly didn't seem as smart as me—were closing deals and making money.

The breakthrough came when my mentor hit me with reality: "Stop trying to make everything perfect. Get the deal in, then use that money to hire other people to make the system you actually want."

The perfectionist trap works like this: You convince yourself that preparation equals progress. You study instead of execute. You plan instead of profit. You research instead of risk.

Fear gets all the credit for killing dreams, but perfection is the silent assassin. At least fear is honest—you know you're scared. Perfection disguises itself as productivity while slowly strangling your momentum.

The cure? Embrace "good enough" execution over "perfect" preparation.

My first deal was messy. My follow-up system was basic. My market analysis was probably wrong. But it worked, and working beats perfect every single time.

Your move: Pick one business idea you've been "perfecting" for months. Give yourself 48 hours to launch an imperfect version. Done is better than perfect, and profit beats planning.

Sometimes the smartest thing you can do is start before you're ready.

The Takeaway

The smartest money isn't chasing perfection or the sexiest opportunities. It's building boring systems that work while focusing on markets that actually deliver. Sometimes the best strategy is the one that makes you yawn—but pays you while you sleep.

I'll create an in-depth guide or video for whichever topic gets the most votes. Important: Use the exact subject line format above or your vote won't count (think hanging chads, but for newsletters).

Can't pick just one? Forward this to someone who needs to see that money can work while they sleep—they'll thank you when their side hustle hits Season 3.

📤 Forward this to someone who needs to see that money can work while they sleep.

Can't pick just one? Forward this to someone who needs to see that money can work while they sleep—they'll thank you when their side hustle hits Season 3.