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Issue #10: Creating The Side Hustle Flywheel

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Hey there, entrepreneurial adventurers and side hustle enthusiasts!

Welcome to Issue #10 of My New Meta!

MILESTONE ALERT: We've hit double digits, baby! According to completely made-up statistics, 99% of newsletters die before their 10th issue. (Usually from chronic dad-joke fatigue)

We're officially in the 1% club! (...of newsletter survival, not wealth. Still working on that part.)

⚠️ FAIR WARNING: This issue is tweet-heavy. If you're not into X/Twitter drama, you might want to skip this one. (Looking at you, LinkedIn purists 😉)

Today's Big Idea: Forget waiting for that "perfect" business idea. It's like waiting for your soulmate while refusing to date.

Instead, let's talk about building a portfolio of connected side hustles:

  • Start with your network (hello, Twitter!)

  • Build distribution (hey there, newsletter!)

  • Add ventures that play nice together

  • Watch them help each other grow

The best part? You can start RIGHT NOW. (Yes, even during your boring Zoom meeting)

Let's dive in...

First time reading? Sign up here.

Side Note: Embracing the "Pedestrian" Path

Remember when I said franchising was too "basic" for an aspiring newsletter mogul?

Well, plot twist: I'm OFFICIALLY BASIC! 🎉

That's right - like a tech bro finally admitting that maybe Crocs are comfortable, I've embraced the franchise life.

Congratulations Congrats GIF

Giphy

And you know what? Turns out being basic can be beautiful.

We've closed on a consumer tech-adjacent distribution venture that's about to teach me some humbling lessons about putting pride aside for profit. (Full details dropping next week!)

Think of it as a side hustle within a side hustle - we're getting inception-level here, folks.

Because sometimes the best moves in business aren't about reinventing the wheel.

They're about swallowing your pride and riding a wheel someone else already perfected.

Building a Life of Connected Side Hustles: The Birth Of Our HoldCo

When I was ejected from the corporate mothership six months ago, I spent a lot of time reflecting on what I really wanted my life to look like. I kept coming back to this fundamental truth I'd tweeted about:

A tweet about life

Flipping the Digital Leverage Script

First discovering what modern leverage was in Update #2: From Naval to LandLogic, I then discovered Dickie Bush's framework for digital leverage. Here's what's fascinating - while most creators follow his pillars in order (Build → Sell → Distribute → Network), I'm actually working backward.

4 pillars of digital

Here's where I flipped the script:

Step 1: Started with NETWORKING Because in today's digital age? Attention is essentially free.

LinkedIn and Twitter became my playground. No fancy strategies - just me, sharing my journey and connecting with other corporate escape artists.

Step 2: Starting building the DISTRIBUTION through My New Meta (and another new product coming next week). This newsletter isn't just content - it's a value exchange:

  • I share my failures (there are many 😅)

  • You pay with your attention

  • We both get smarter

Welcome to the new digital economy, where attention is the real currency.

Step 3: Only NOW, moving to BUILD and SELL. Here's the genius part (if I do say so myself):

Every product we launch already has an engaged community that has watched its development from day one.

It's like having beta testers, focus groups, and a cheerleading squad all rolled into one.

Think of it as the entrepreneurial version of the Spice Girls:

  • Each piece brings its own flavour

  • Together, we're making sweet business music

  • And yes, I'm obviously Ginger Spice

The Future Is Already Here

Then Akram Khan dropped a tweet that made my brain explode 🤯

His list wasn't just predicting trends. It was revealing the DNA of modern business:

  • One-person armies

  • Powered by free tools

  • Building global audiences

  • From literally anywhere

  • All connected through digital communities

The future of business

But here's where it gets wild...

This perfectly fits into Dickie's leverage framework like a missing puzzle piece.

Think of it this way:

  • Dickie gives us the "how" (build, sell, distribute, network)

  • Akram shows us the "what" (the actual building blocks)

It's like having both the Konami Code AND the strategy guide:

  • One tells you the right moves

  • The other shows you where to use them

  • And yes, I'm dating myself with that reference 🎮

When you combine these frameworks with my earlier revelation about work and life being two sides of the same coin...

BOOM! 💥

You get something magical:

A blueprint for building not just a business but a lifestyle where work and passion are inseparable.

(And isn't that the whole point?)

The Real Estate Wake-Up Call

Let me tell you what 30 years in real estate taught me:

ONE BIG LESSON: Diversification isn't just about spreading risk. It's about creating opportunities.

But here's the thing...

I was doing the exact opposite:

  • One job

  • One industry

  • One asset class

You know, like putting all your eggs in one basket. Then, building a shrine to that basket. Then, betting your life savings on that basket.

(Yeah, not my smartest move.) 🤦‍♂️

Did this traditional approach work in the old economy? Sure.

But the digital age? It's a whole different game.

It's like showing up to a Fortnite battle with Canadian Tire money (Yes, U.S. folks, this retailer had its own currency). You might look rich, but you're playing the wrong game.

The Holding Company Revelation

And then... I discovered Andrew Wilkinson's Tiny.com 🔍

Here was a guy who turned diversification into an art form:

  • Buy cool businesses

  • Help them grow

  • Repeat

But wait... what if we flipped the script?

Instead of just acquiring businesses, what if we BUILT them?

Picture this: A holding company that CREATES tiny, interconnected ventures.

Think "The Breakfast Club" but make it business:

  • The Rebel (our media ventures defying traditional rules)

  • The Brain (our real estate advisory, the proven expert)

  • The Princess (Undisclosed franchise, the shiny new revenue generator)

  • The Athlete (our newsletter production, doing the heavy lifting)

  • The Basket Case (that's me, trying to manage it all)

Somehow, like those misfit teens in detention, these different ventures:

  • Share resources

  • Cross-pollinate ideas

  • Make each other stronger

  • Create something bigger than themselves

And the best part? They all grow up together.

(Someone queue "Don't You Forget About Me" 🎵)

Putting It All Together

This led to the reimagining of LandLogic Development Corporation (LDC) as our own version of a modern holding company. Think of it as a startup studio meets a holding company but with a twist. Every venture we launch:

  • Starts with an audience-first approach (thank you, Dickie)

  • Utilizes digital leverage and minimal resources (thanks, Akram)

  • Solves problems I genuinely enjoy tackling (as per my tweet below)

  • Connects with and strengthens our other ventures

The beauty of this structure isn't just in its diversity - it's in its synergy. Each venture feeds into and strengthens the others, creating what Naval Ravikant calls "specific knowledge" across multiple domains. We're not just building separate businesses; we're building an ecosystem where success in one area creates opportunities in others.

Where It All Lands

Building something that looks like a business Picasso:

  • Nothing quite where you'd expect it

  • Traditional folks tilting their heads in confusion

  • But somehow, it all works

It's not a holding company. It's a laboratory for the future of work. (With me as the slightly caffeinated mad scientist 🧪)

**And yes, I don’t get very many Likes 😔 

The future of work isn't about following the old playbook. It's about writing your own story. (Even if that story makes your MBA professor cry)

And we're just getting started...

Because the future?

It belongs to the people who can:

  • See connections others miss

  • Build bridges between opportunities

  • Create their own rules

  • And aren't afraid to be different

⬇️⬇️⬇️⬇️⬇️⬇️ The Real Side Hustle Sauce ⬇️⬇️⬇️⬇️⬇️⬇️

All you side hustlers, listen up. See this ad below ⬇️. This is your money-printing machine.

Warning Inside Out GIF by Disney Pixar

Gif by disneypixar on Giphy

Start writing and start earning $$$$$$.

You click this link, and the newsletter makes $1.50.

You might think, ‘I ain’t writing a thing for a buck fifty

Well, my friends, when you have an email that goes out to thousands of people and 15% of those fine folks click the link…bingo, side hustle!! Join me at BeeHiiv; there is a free version, no excuse.

The Ad:

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CURATE & COMMENT

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🧑‍💻 From The Wasteland of Reddit

Check out this post for some simple side hustle inspiration: I made $117 this week selling plants.

🎥 Podcast Of The Week

It’s almost the holiday season; it's time to make some extra dough. Try Etsy.

Side Hustles: You don't need 12 hours a week, startup costs, and an MBA to start one.

You need an audience, a product/service to launch and basic marketing.

In this new weekly series, we will go from Chucky being a ”side hustle curious” to monetizing his overly specific niche.

Week 4: The Wrap Up

SCENE: A month later. Greg's home office wall now features a framed vintage bowling ball. As the video call connects, we see Chucky in what appears to be a small but professional-looking workspace, surrounded by vintage bowling balls, photography equipment, and a whiteboard filled with content ideas.

(New here? Catch up on Chucky's entrepreneurial saga! Check out Issue #7: RIP My New Meta, Issue #8: The GOAT JOAT,and Issue #9: The N00b's Guide to Not Getting Pwned to follow his journey from confused side hustler to niche market maven. Each issue builds on the last, so you'll want the full story!)

Greg: Well, well, well... look who's gone full pro! That's quite the setup you've got there, Chuck.

Chucky: (grinning) Remember when I thought I was just going to flip bowling balls? Man, was I wrong! The last month has been insane. Want to hear the numbers?

Greg: Hit me with it! Our readers are dying to know if this actually worked.

man with his fingers stuck in bowling ball

Chucky: (pulling up a spreadsheet) In 30 days:

  • Launched "The 5-Pin Chronicle" newsletter: 147 subscribers

  • Created "The Vintage Keeper's Guide": 23 sales at $37 each

  • Authentication services: 12 balls verified at $50 each

  • Restoration consulting: 5 clients at $75/hour

  • Total revenue: $1,751

Greg: (whistling) Not bad for a month's work! What was the biggest surprise?

Chucky: That the real money isn't in the bowling balls - it's in the knowledge! These collectors don't just want products; they want expertise, stories, and community. Remember how anxious I was about "selling" to the community?

Greg: (laughing) Our undercover bowling ball anthropologist!

Chucky: Exactly! By following your community validation framework (below), I discovered what they actually needed. Now, I'm not selling TO them; I'm selling FOR them. I'm helping preserve their passion!

Greg: Break it down for our readers, Chuck. What were the key steps?

Chucky:

  1. I found my niche using Andrew's framework Issue #7: RIP My New Meta 

  2. Validated the community using the 6 steps Issue #8: The GOAT JOAT 

  3. Discovered hidden opportunities through observation Issue #9: The N00b's Guide to Not Getting Pwned 

  4. Built trust by sharing knowledge first

  5. Created solutions to actual problems

  6. Let the community guide my product development

Greg: And the biggest lesson learned?

Chucky: (picking up a bowling ball) Success isn't about what YOU want to sell. It's about what your community needs. Oh, and get this - three industry veterans just asked me to co-author a book about the golden age of 5-pin bowling!

Greg: (beaming) Chuck, you've graduated from Entrepreneur-in-Training to Community Champion! Any final advice for our readers?

Chucky: Yeah... don't skip the research phase! I almost jumped in trying to sell bowling balls on Facebook Marketplace. Instead, I followed the frameworks, did the work, and found a real business opportunity. Now, I get to make money doing something I love, helping people I respect.

Greg: And that, folks, is how it's done! But hey, this isn't goodbye - Chuck has agreed to pop in occasionally to share updates and insights from his journey.

Chucky: (holding up a particularly rare bowling ball) Absolutely! This community helped me find my path. The least I can do is help others find theirs.

Lessons from Chucky's Journey:

  1. Follow frameworks - they exist for a reason

  2. Trust the validation process

  3. Listen more than you sell

  4. Build value before monetizing

  5. Let your community guide you

  6. Focus on solving real problems

Your Turn:

  • What community are you part of that might need your expertise?

  • What problems could you solve for them?

  • Hit reply with your ideas - maybe you'll be our next success story!

THAT’S A WRAP

If any of these stories resonated with you (or if you've also discovered a forgotten side hustle buried in your past), hit reply and let me know. I'm genuinely curious how many other corporate warriors have hidden chapters in their entrepreneurial journey that they've temporarily misplaced.

How did we do this week?

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Stay weird, stay curious, and keep building.

Greg "All Charged UP" Mills

Note: Some of the links in the newsletter are affiliate links. I believe in transparency and honesty, so if you want to know more, visit Full Partner Disclosure for details.

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