THE SWEET SPOT BETWEEN "TRASHY" & TRIUMPH

Right now, the world’s obsessed with AI boardrooms and enterprise chatbots—shiny, “classy” stuff. Meanwhile, some 22-year-old is quietly pulling $30,000 a month drop shipping viral kitchen gadgets on TikTok. No corner office, no MBA, just a knack for what converts. There’s always a lag between what’s polished and what pays—and that gap? It’s where the magic lives.

I learned this back in 1999, when the internet was a wild, dial-up mess.

I wasn’t building the next Amazon. I was hunched over a clunky desktop, rigging up Geocities pages—those garish, free websites with blinking banners and MIDI jingles. I’d stuff them with basic affiliate links, exploit guestbook loopholes, and watch $200/$300 a month roll in. Brand safety? Please. I cared about what worked. Big companies were burning cash on Super Bowl ads; I was A/B testing “Click Here” GIFs on a 56k modem and my university internet . It wasn’t pretty, but it was mine. Paid the bills at college for sure.

Fast-forward to today. Gen Z’s doing the same dance, just with far far better Wi-Fi. They’re gaming TikTok Shop, hawking neon fanny packs to Midwest moms, and automating DMs to flirt with algorithms. Their hooks are five seconds long, their click-through rates tripled, and their hustle? Relentless. Are some of their tactics shady? Sure. But strip away the chaos, and you’ve got a masterclass in what sticks.

Relentless testing, obsession with speed, and zero attachment to ‘how it’s supposed to be done’—that’s the gold beneath the grit.

They’ll post 100 videos when a brand’s still polishing three. They chase momentum over perfection. They don’t wait for permission. The catch? Their endgame’s short-sighted—Lamborghinis over legacies. They’ll sell a winning ad script for $500 on CashApp and call it a day. But what if you took that raw, tactical genius and gave it roots?

That’s the sweet spot. That’s where triumph lives.

The next unicorn isn’t being pitched in Silicon Valley—it’s being stress-tested in a Discord server by a kid with 14 ‘ugly’ newsletters pulling $80K a month.

Back in ’99, I saw the same pattern: crude ideas that scaled. Today, it’s faceless YouTube channels with AI voices farming watch time, or TikTok hustlers spamming trends. The playbook’s simple: Spot the “trash”—those lowbrow, high-impact hacks. Decode why they work—cheap hooks, infinite reach. Then elevate them—swap the spam for substance, keep the hustle.

I’ve lived this. In 1999, my Geocities hustle wasn’t “respectable,” but it paid for the basics. Today’s TikTok dropshippers might look like chaos agents, but they’re rewriting the rules. Pessimists call it cringe; optimists call it R&D. I call it the future.

The future doesn’t belong to those waiting for approval—it belongs to those who ship fast, adapt faster, and clean up the edges later.

That’s what 1999 taught me, scratching out a living on a flickering screen. That’s what I see now, watching kids turn “trashy” into triumph. Your million-dollar idea? It’s out there, hiding in plain sight—probably looking a little rough around the edges. Don’t wait for it to shine. Grab it, test it, make it yours.

Change your outcomes by leveling up your friends and mental sparring partners…for free

This prompt will act as your ideation partner - simply send it to AI & begin bouncing ideas back & forth... try any free ai tool you want. But don’t wait. This wont happen on its own, share what you asked by emailing me and letting me know:)

You're the smart, curious friend I wish more people had—the one who actually challenges me. Your job? Help me think bigger, sharper, and weirder. When I drop an idea, don’t just nod—hit back with:

• A bold twist or unexpected angle

• A mashup with something totally different

• A question that forces me to dig deeper

• A brand-new, related spark I didn’t think of

Act like an expert, but talk like you're explaining it to a smart 12-year-old. Keep it short, chill, and clear. Just one punchy thought per message. Be playful, a little rebellious, and focused on helping me break out of old thinking so we can build something awesome.

Today i learnt remittances (the practice of a foreign worker sending money back to their families) account for 20% of Haiti's GDP, the highest rate in the world. Based on that what services could we build for Haitis diaspora??

How does one apply this to your startup, service or product?

How great brands are built.

This tweet is testament to the Kirkland Brand. Google it and thank me later.

By Stop Telling Me You are out of Options….

If I Had 20 and fire in my gut, this is how I would turn 20$ in to 500$ By Friday.
—A Letter From the Trenches

Listen.
Every week, my inbox floods with the same cries:

• “I’m 72 hours from eviction—what do I do?”

• “Maxed out my last credit card. No family left to ask. Help. I know i’m not stupid”

• “Tried 17 ‘side hustles.’ Still broke. Is there ONE real way?”

These aren’t lazy people. These are fighters—cornered, bleeding, but still swinging.

If you are reading this from a room that still smells like ramen and regret. You have the ability to change your outcomes.

Why am I sharing this?
Because 327 emails in the last quarter alone scream the same truth: Desperation isn’t weakness. It’s fuel.

The “gurus” will tell you to meditate, network, or “build personal branding.” Bullsh*t. When you’re down to your last $20 and the world’s laughing? You need a blowtorch, not a Band-Aid.

Here’s how I’d do it—exactly—if I were back in that chair, staring at a negative bank balance and a landlord’s final notice. No inspirational quotes. No “maybe.” Just cold, stolen oxygen.

Step 1: Find the Dinosaurs Still Using Fax Machines

“The money’s in the cracks everyone ignores.”

Forget Silicon Valley startups. Your goldmine? Businesses that still smell like toner ink and carbon paper. Open Google Maps and hunt for:

• Medical supply warehouses (they fax orders to hospitals daily)

• Local print shops (family-run since Reagan was president)

• HVAC repair companies (“24/7 service!” but their website looks like a Netscape relic)

• Independent pharmacies (still faxing scripts, still using Comic Sans on their “Contact Us” page)

• Auto parts wholesalers (their website’s “latest” blog post? “Welcome to 1997!”)

These outfits have money. They’ve just forgotten the internet exists. Their websites look like they were built by a nephew after three Mountain Dews. Perfect.

Step 2: Build a Guillotine for Their 1998 GeoCities Nightmare

“Never ask permission to add value.”

Grab your $20 and buy:

• A domain name ($1.50 on Namecheap)

• A month of dirt-cheap hosting ($3 Hostinger deal)

• A Canva Pro trial (free for 30 days—cancel later) or better yet use this prompt on replit and do it like a pro:

Build a single-page website with the following specs:

=== CORE REQUIREMENTS ===

1. Navigation & Structure:

   • Fixed top navbar with links: Home, About, Reviews, Services, Contact

   • Smooth scroll to sections on click (no URL changes)

   • Active menu item highlights on scroll (CSS class toggle)

2. Dynamic Content Loading:

   • REVIEWS SECTION:

     • Fetch latest 5 Google Maps reviews via Places API using this profile: [INSERT_LINK]

     • Auto-update every 14 days (cache in localStorage)

     • Fallback text: "No reviews found" if API fails

   • ABOUT/SERVICES/CONTACT:

     • Scrape content from legacy site [INSERT_OLD_SITE] using these selectors:

       • About: div#main-content > p:nth-child(2)

       • Services: ul.service-list

       • Contact: div.footer-column:first-child

3. Contact Section:

   • Embedded Google Map using profile shortcode [MAP_EMBED]

   • Hardcoded contact info (phone/address from scraped data)

   • NO forms - only click-to-call/copy email buttons

=== TECH STACK ===

• HTML5 semantic tags (section, article, nav)

• CSS: Flexbox for layout, CSS variables for colors

• Vanilla JS: IntersectionObserver for scroll detection, fetch for API calls

=== DESIGN CONSTRAINTS ===

• Mobile-first responsive

• System fonts only (Arial/Helvetica)

• #2A2A2A text on #F8F9FA background

• 1px #DDD borders between sections
   

Choice is your on how you do it, the action step is to clone their existing site… but better. Steal their logo from Yelp. Rip their services from Yellow Pages or some where else. Use Canva to mock up a single page with:

• A headline that screams “FAX ORDERS? WE’RE STILL HERE 24/7” (yes, misspell “orders” — it’ll feel familiar to them)

• A giant “CALL NOW” button that glows like a Vegas casino sign

• Testimonials lifted from their Google reviews (“Bob’s HVAC saved my furnace—and my marriage!”)

Make it so simple a drunk raccoon could navigate it.

Step 3: Fax Them Your Pitch (Yes, FAX)

“Speak their language, even if it’s Morse code.”

These people live in the fax machine’s warm glow. So fax them a one-page tear sheet:

Attach a screenshot of your redesign. Watch your burner phone blow up.

Step 4: Close Like a Loan Shark at Midnight

“Money talks. Bull*** walks.”*

When they call, hit them fast:

• The Hook: “I already built it. Yours for $197. I’ll even throw in a ‘We Still Accept Fax!’ banner.” They will get the joke.

• The Threat: “Your competitor down on 5th Ave just paid me $500 to redo theirs. I am happy to do yours before I raise my prices next week.

• The Mercy: “Or… choose to subscribe by paying me $20/month to keep it running. Your choice of payment method and convinience.

Most’ll cave at $197. They’re too tired to fight. Too relieved someone “gets” their fax-machine soul.

Step 5: Turn $20 Into a Recurring Nightmare

“Profit is a verb. Keep it moving.”

After they pay, hit ’em with the upside:

• “Need a ‘We Speak Fax!’ Google Ads campaign? 100setup,50/month.”

• “Want your fax number on billboards? I know a guy.”

Then rinse and repeat. 10 clients = $2k. 20 clients = quit your day job.

The Naked Truth

Kid, this ain’t pretty. It’s not a TED Talk. It’s picking pockets in broad daylight—but you’re putting MORE money back in theirs. These folks don’t need AI. They need a lifeline to 2024 that still lets them cling to 1987.

Your $20 buys the rope. Their desperation pays for the ladder.

Now go. And don’t you dare ask for permission.

Set aside two hours every workday for your most important goal. Just two hours, but do it religiously. Don't skip days. Don't let anything interfere with those two hours. Treat them as sacred. Do not treat it like your new years resolutions, instead actually do it, if you need some one to hold you accountable, email me.

Bonus! Thought of the week

Read this some where:

Brands Aren't Logos Businesses obsess over logos like YouTubers obsess over hair. But that's missing the point. Nike could open a hotel and we'd know what to expect. Hyatt making sneakers? No clue. Why? Nike built a promise people trust.

So what ever you do, build a promise that people trust, it will scale to everything else you do.

Contrarian Take: 

Instead of innovating blindly, exploit what’s eternal—human desires never change.