From Italy to Ireland to Canada: A Real-Time Relocation Shift

Notes from the trenches of the sovereign architect.

One of the promises I made at Borderless Living was that I’d chronicle, honestly and in real-time, the process of moving myself, my wife, our kids, our dogs, our assets, and our generational wealth out of the United States—without having a nervous breakdown.

Initially, that path started with a clean narrative arc: acquire Italian citizenship via jus sanguinis, move to the EU, enjoy Aperol and constitutional rights. Done and dusted.

Then Meloni came to power—and rewrote the script.

Suddenly, our “Plan A” was toast. But as I’ve said many times here: if you’re building a sovereign architecture, one path is never enough. You need 19. Some are backups. Some are traps you set for the system. Some are fire escapes.

We had contingencies: Ireland. Canada. And at the time, Ireland seemed the more attractive choice—for lifestyle, law, and Europe’s long-term strategic value.

That was before I started reading Ireland’s tax code.

Ireland Hates Generational Wealth

While we’re not “Succession” rich, we are rich enough to need legal armor. There are trust structures, managed portfolios, attorneys, fund administrators—the usual architecture built to protect wealth across generations.

And then the question hit: How will Ireland view this income?

Short answer: not favorably.

Ireland treats U.S. trust vehicles with skepticism bordering on hostility. If my reading is correct—and I’m now consulting firms like Matheson and Arthur Cox to verify—Ireland’s default posture is: screw your tax avoidance, pay me. Taxation on undistributed gains. Capital gains without realization. Confiscatory rates. Little recourse.

My kids were crushed. They loved the idea of Ireland. But when I explained they’d likely be paying taxes on money they never received, and might end up begging in Temple Bar with a tin cup, their loyalty quickly transferred to Canada.

Canada: The Polite Confiscator

Canada isn’t perfect. But it’s measurably less hostile.

While I’m still waiting to speak with Blakes and Green and Spiegel to verify the details, my early read is that Canada taxes actual income—not unrealized gains. Its approach to trusts is more structured. The “21-year rule” exists, but with planning, it’s manageable. That makes it a potential landing zone—though still one lined with legal tripwires.

This pivot also reminded me just how good America is at one thing: finance.

The U.S. Is a Financial Hyperpower

As I started comparing systems, it hit me: the U.S. doesn’t dominate because of military might or Apple stock—it dominates because it invented modern capital plumbing.

Take something as simple as a 30-year fixed-rate mortgage. In America, it’s a right of passage. In Canada and Ireland? It doesn’t exist.

Why? Because those countries don’t have the mortgage-backed securities infrastructure to enable it. The U.S. built Fannie, Freddie, Ginnie. It created secondary markets for debt. It turned mortgages into investment products—and that enabled a middle class.

We nearly nuked the global economy doing it (thanks Lehman), but the machine itself is a marvel.

🚨 Quick Note Before We Go Further
If you’ve made it this far, you’re not casually curious—you’re building your own sovereign architecture.

Starting July 5, the price for Borderless Living is going up:
Monthly: $50
Annual: $480

Right now, it’s still $30/month or $300/year.
And to make this easier:

🎆 I’m running a Fourth of July Sale — 20% off all annual subscriptions through July 4.

Since March, we’ve released 15 paid-only pieces—including country briefs, political risk analyses, and sovereignty planning guides. That’s over $3,000 worth of strategic research delivered for just $300/year. Starting July 5, we’re increasing the price to reflect the depth, speed, and growing demand for this work.

Americans Need to Shut Up About Taxes

Here’s the other thing that hit me in this research sprint: Americans have no idea how good we have it on taxes.

If the U.S. ever proposed a flat 33% tax on unrealized capital gains and undistributed trust income? The entire country would riot. People would be building guillotines in front of the Treasury.

But that’s the norm in a lot of the world—including places we romanticize as "civilized."

Yes, in Minnesota I pay high taxes. But I also get functioning roads, schools, hospitals, and clean governance. The ROI on taxes is solid. And even with that? U.S. tax policy still favors investment, innovation, and family wealth protection far more than the OECD average.

Immigration Law Is a Nightmare

Meanwhile, immigration law makes tax law look like a coloring book.

I’ve spoken to top firms in Ireland and Canada. They’ve all been professional, kind, helpful—and uniformly clear: this is a long, expensive, paperwork-filled pain in the ass. I wasn’t shocked about this, which is why I’ve engaged legal counsel in the first place. And given all the years I worked in government, I’m no stranger to bureaucratic nonsense. Even so, it’s still jarring to consider the actual cost of making this happen and the planning timeframes. It’s almost a year to make this happen, hence why I knew I had to get serious now (given my departure of just before the mid-terms.)

It’s almost comical: the ten countries Americans most want to move to—France, Japan, Germany, Australia, etc.—are also the ten most difficult to legally enter. Japan? Basically, a closed temple.

The most common path remains: “just show up and figure it out.” That works—until it doesn’t. And when it doesn’t, your entire life can collapse on procedural grounds.

It gave me a new appreciation for illegal immigration. I mean, if you’re broke, fleeing oppression, and desperate, sneaking in makes perfect sense. It’s certainly a lot easier than 200 team hours and $30,000-$ 50,000 to sort out a lawful path. (Chuckle.)

Me, I kinda thrive on all that compliance bullshit. Most people, however, can’t stand it. To me it’s like a game. To most people, it’s like eating broccoli. Now, of course, I don’t recommend you just illegally immigrate, but for those who do it (or don’t do things like file proper paperwork, pay taxes, etc.) I can understand the frustration, surrender, and sheer “I give up” feeling that comes with it all.

What Borderless Living Is Really For

All of this has clarified the real job of Borderless Living.

This isn’t a Substack for backpackers or crypto bros looking to pay zero taxes in Paraguay. It’s a framework for high-agency individuals navigating geopolitical and financial complexity.

Borderless Living is for the financially fluent but not “fuck-you” rich—people with $1M to $10M in assets, professional lives, and something real to protect. You’re not flying private, but you also can’t afford to get this wrong. A mistake at best means a fine, at worst, means prison.

The stakes are existential. One misstep—one overlooked tax clause, one mistimed move—and your entire wealth architecture collapses inside a generation. That’s not fear-mongering. That’s math.

And while Borderless can’t be your sovereign wealth manager, your lawyer, or your accountant, I can help cut through the myriad of problems and layers to help reader figure out what to do next, whom to talk to next, and begin to put together a plan of how to make it all work.

The Sovereign Architect’s Real Job

So here’s the game as I see it:

🧩 You must select jurisdictions based not just on lifestyle, but legal compatibility with your wealth structure.

🕰 You must think not just about the next 6 months, but about how today’s move impacts your tax, residency, and citizenship status 19 years from now.

♟ You must treat each decision like 3D chess—played across borders, currencies, and timelines.

I’m not just chronicling theory—I’m walking the same path you are. And if you’re sitting in that 2–10M band, trying to move smartly across borders, the window to get this right is narrow.

That’s what Borderless Living is here for.

Prices are going up after July 5—because the work is getting deeper, the value is getting sharper, and the stakes for all of us are rising.

Join now, lock in the current rate, and build the life they said you couldn’t.

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🧭 What’s Coming Next at Borderless Living

In the coming weeks, I’ll be releasing:

• The Canada Wealth Migration Brief — breaking down the real implications of the 21-year rule, provincial tax cliffs, and how CRA treats trusts.

• Jurisdictional Compatibility Matrix (v1.0) — a visual framework ranking top migration destinations by compatibility with U.S.-based trust and wealth structures.

• The Sovereign Architect’s Toolkit — the exact questions to ask lawyers, wealth managers, and immigration consultants before you pay a dime.

• How to Build a “Shadow” Family Office Without Being UHNW — leveraging off-the-shelf providers to replicate family office capabilities on a practical budget.

This is actionable, strategic intelligence—the kind you’d usually pay $20K+ to a boutique firm or family office to even scratch the surface.

If you want access to that, and everything we’ve got coming next—now’s the time.

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🔄 Other Key Changes Coming After July 5

We’re raising prices—but not just because we’re doing more work.
We’re evolving Borderless Living into a deeper, more structured ecosystem for serious Sovereign Architects.

Here’s what’s changing starting July 5:

💬 Discord Access = Paid Subscribers Only

The BL community Discord is going private. We will not be giving free subscribers access to the Discord after July 5. If you want access to the private forums, updates, and real-time discussion—become a paid member.

🧠 Monthly Strategic Briefings + AMA

Every month, I’ll host a live strategic briefing and Q&A session in Discord.
We’ll cover market shifts, country updates, legal strategies, and take your direct questions. The next briefing will be Saturday, July 12, 2025. The announcement will be made in the Discord.

📚 More Premium Content

Starting in July, paid subscribers will get:

• 2 Country Briefs per month (minimum)

• 2 Sovereignty Guides per month
  No fluff. No filler. Real, vetted intelligence you can act on.

Each one of our briefs is worth $1000+ or more if you went to someone who was a professional and asked them for the insights. Some of our briefs, like the political risk analysis, would be impossible to get except from a private intelligence firm.

👥 Expanded Support for Paid Members

I’ve brought on additional staff to help with research, admin, and support.
This means faster answers, better resources, and a smoother experience for every paying subscriber.

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👑 Introducing: The Sovereign Architect Tier

We’re retiring the “Foundation” tier.
Meet the Sovereign Architect Tier—for those ready to build parallel infrastructure with purpose.

At this level, you’ll receive:

• Full access to Borderless Living

• Full access to The Long Memo

• 1:1 private discussions with me, monthly

• Priority input on new content, guides, and projects

Let’s be blunt:
For the cost of four hours with a mediocre international tax lawyer, I’ll point you in the right direction—without billable hour games.

⚠️ Capped at 20 members to maintain quality and access.

🛡 This is not a newsletter. This is strategic command and control for sovereign actors.

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📅 Monthly/Annual Prices go up after July 5
🎆 20% off annual plans until July 4

Join now. Lock in the current rate.
Start building the life they said you couldn’t.

As always…

Stay safe.
Stay sovereign.
Stay Borderless.

And thanks for reading.

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🚨 UPDATE (7/1/2025 – 3:22PM CDT)

In response to the substantial demand for the Sovereign Architect tier, here’s the updated approach—and a new incentive for existing paid subscribers.

💳 Already a paid member (monthly or annual)?

If you're thinking about upgrading to the Sovereign Architect tier, I’ll credit 100% of what you’ve already paid toward the $2,000 upgrade.

How it works:

• Email or DM me at editor@thelongmemo.com with the email tied to your Substack account.

• I’ll look up your payment history and generate a custom invoice via Stripe.

• Once paid, I’ll manually comp your Sovereign Architect access on Substack—this unlocks all benefits and ensures nothing you’ve paid is wasted.

• Going forward, your SA subscription will renew automatically on the anniversary.

This approach also avoids unnecessary platform fees—and keeps things simple.

🧾 Bonus: Family Access Included

As a Sovereign Architect, you’ll also receive comped full access to Borderless Living for any immediate family members you'd like to include—spouse, partner, adult children, etc.

Anyone you want involved in the planning, the calls, or the execution? They’re in. No extra charge.

How’s that for a deal? 😄

You keep your credit. You get premium access. And your whole household can join the conversation.

Let me know if you want to move forward.