Being a seasoned Job Stacker, it’s also incumbent upon me to dispel any notion that job stacking is an entirely easy enterprise. In fact, today, job stacking has become one of the more difficult employment strategies to pull-off effectively (assuming you’re even of the caliber to land two remote positions).

What ensues are five reasons you SHOULD NOT Job Stack. If you want the solutions to these problems — you’ll have to pay me or become a fully fledged Tortuga Member.

The Reasons You SHOULD NOT Job Stack Are:

The Bullshit Jobs Era is Over

You Can’t Handle the Cognitive Load

You Don’t Have Thick Skin

You Don’t Have Grand Ambitions (Business / Art / Exit Plan)

You Have No True Männerbund

1. The Bullshit Jobs Era is Over

It’s the year 2021 and the market is flush with fully remote juicy sinecure positions. The hiring process is fast-paced, managers are eager to create new positions, and having a STEM or adjacent degree has never been better. Covid stimmies are flowing and the market is booming — our beloved corporations are looking to maximize profits for their shareholders. In this funny money environment — the easiest way to do so is to market just how much your vaporware nonsense enterprise specializing in extracting an additional 2 seconds of screen time from dopamine laden teens’ eyeballs is growing.

So they went on a hiring spree…

Now did they actually need 90% of these new positions? Not at all. But for the intelligent among us, this was an incredible opportunity: a surplus of high-paying remote jobs that asked little of us sans an occasional Tableau report or ad-hoc SQL query. The true glory days of job stacking…

The first reason you shouldn’t job stack is that this halcyon era of yore has long since ended. There are many reasons for this: the Fed’s raising of interest rates, the rise of AI, and deeper policy decisions rearing their ugly heads.1

Remote jobs are increasingly rare and there’s more competition than ever for the few that remain.

2

3

These trends on their own are bad enough but the situation get’s much worse when you realize these few remote full-time positions are far from “bullshit”. Even if you’re able to beat the odds and land two of them they will be a far cry from the sinecure’s of 2021.

Over the past three years in particular, layoffs have been massive and the positions that remain are increasingly asked to do more with less staff. In 2021 your particular data analysis department may have had 11 team members to split the work requests that came in. In 2026, that department likely now consists of only four team members to take care of that same workload.

Take it from me; I’ve had my two fully remote positions for over two years now and they keep me busy the entire eight hour day (and occasionally some weekend time as well). Now let me be clear — this is an amazing setup and I make well over $300k now. My wife doesn’t have to work, I was able to help my parents retire, will be able to purchase a nice house with 60% down soon and I’ve gone on some amazing trips — all thanks to job stacking.

So if you aren’t a particularly agentic intelligent guy — job stacking is most likely out of the realm of possibility for you. It ain’t 2021 anymore bucko.

2. You Can’t Handle the Cognitive Load

Here’s the thing: Job Stacking is more about juggling identities than it is about juggling tasks. A simple way to understand this is by thinking about your current role. What would it look like if you doubled the work load? Obviously, it would be a straightforward 2x increase. This isn’t the case with job stacking — it’s more like a 2.5x increase in work load.

Why?

Because we aren’t just doubling the work that needs to be performed; we’re also doubling the identities we’ll need to slip in and out of. Job A will have its own set of team members, applications/software, exigencies, meeting schedules, etc… as will Job B.

You will need to context switch multiple times every day. You will need to manage priorities among the two jobs every day. You will be held accountable by two different bosses every day.

You will need to persistently manage your calendars and block time off to avoid the dreaded double meeting and sometimes this will fail. The true mark of a pro job stacker is how many double meetings he’s survived… the left headphone attached to a meeting in Job A, the right to a meeting for Job B — engaging in the terrifying dance of remaining muted for each as long as possible and listening assiduously for your name to be called. Better make sure when you unmute for Job B you remain muted for Job A… there are many horror stories of stackers getting caught this way. 4

Best of luck to you if one or god forbid both meetings require cameras on (you best be quick on your feet for some improvisational excuses).

3. You Don’t Have Thick Skin

Invariably, if you have 2+ remote jobs you’ll encounter a time or two where you’re unable to deliver on all your workload for one reason or another. This is where you must have thick-skin and be able to stand your ground.

Concerning the matter of getting scolded by your manager(s) this will happen. If you’re going to job stack you must be able to roll with the punches. This can be especially difficult to handle if you’re a highly conscientious person. Should this occur, you’ll need to be a man about it and take responsibility for the mistake (best to have some excuse but suggest you could’ve avoided said excuse and will next time).

Beyond getting scolded there’s the larger importance of being able to stand your ground. In order to job stack effectively you need to protect your time as much as possible. When you block out time on your calendar and a higher-up schedules over it you need to be able to (professionally & politely) stand your ground that, that time is off limits. The moment you budge is the moment your superiors and team members lose any respect for your time. 5

Seriously, don’t be a pussy — you must protect your time.

See point number 2 again for the consequences of the damnable double meeting.

4. You Don’t Have Grand Ambitions (Business / Art / Exit Plan)

For many here at Tortuga we call Job Stacking “The Final Boss” of their professional ambitions. They start as lowly barnacles, work their way through the bootcamp, land their first hybrid tech position, accumulate some skills & connections through their work and Tortuga’s network, then land their first remote position with our staffing firm, finally securing their second and joining the rank of Captain.

Here’s the thing though…

Read more

I got out of the Publishing Industry in 2022.

On spring break in the middle of COVID lockdowns, my wife and I were on a mission to escape from our apartment and decompress in the Balkan spa-and-winery complex of Starosel. Unfortunately, so was half the population of Sofia.

Just imagine us after a year and a half of being cooped up: with a grandmother, a great-grandmother, a grandfather with Alzheimer’s, a pod of feuding aunts (great and small), and, of course, our kids. We distance-learned, we zoom-met, we face-masked, balcony-clapped, hand-sanitized, and mourned — yes — the death of a great-great-grandmother. Picture my wife and me on the other side of all of that, in a pool filled with half the population of Bulgaria’s capital, attempting to swim.1

One fine day, as I stepped out of the scalding water, trying not to sneeze where anyone could hear, I received this email from my literary agent: “We just got informed that our contact at AWA has left … I do have someone else to query over there but I don’t want you to put in more energy if it won’t pay off.”

AWA was supposed to be a cooperative of comic-book artists and writers. I was going to write one of their story ideas set in Russia with a Russian artist I already knew, but two days after the invasion of Ukraine, our contact had “moved away from the project.” I was organizing classes for refugees, and my friend was getting ready to escape the Motherland, but you’d better move away from the project, Jen. Don’t want to offend anyone in Brooklyn.

I wasn’t upset, but I did feel a certain fatigue, a certain disgust. This “online comic co-operative” had never been a real business. The people pretending to run it weren’t serious. Neither was my agent. Now, I cast no aspersions on this woman, who sent me a bouquet after my colostomy. She was being a good person, but she wasn’t trying to make money. Like everyone else in the Industry, she wasn’t actually in the business of selling books.

The Con’s VIP Room

Back in 2019, my agent sold my debut novel2 to Flametree, a small British press with a line of artsy notebooks that wanted to expand into fiction. They offered very little editing and negligible marketing, but this was standard. Of course a manuscript must be “polished” before a publisher will even consider looking at it, and as for marketing: “the real work begins after you finish the novel. Nobody can market your book better than you.”

What the publisher did offer was copyediting, typesetting, cover art and design, printing, and distribution, a thousand bucks in advance, and most importantly, legitimacy.

With Flametree’s logo and ISBN on my book, I was a Published Author. I got a Kirkus review and an audiobook deal (twice the advance for the print edition). At sci-fi conventions, I could now access certain rooms. A closed web forum was no longer closed to me. Some people, if approached through the right channels, would even speak to me.

Capisce?

One such publishing elite was Sheila. She was a big enough name in the Industry that a meeting with her alone justified my tickets to EasterCon. She began our one-on-one brunch with the story of a cover artist her publishing house had once employed, who had said, in public, that he supported George W. Bush.

Well.

They never worked with him again.

Sheila did not look me in the eye and say, “capisce?” but I got the message.

Now, I did not vote for Bush. I was a well-brought-up young man. I went to a liberal arts college. I knew to face the blade of the butter knife inward when setting the table, and I could be heir to a vast network of favor and patronage. To get access to people like Sheila, I just needed to believe the right things, amuse my superiors, and, I thought, perform competently. That was back in the 2010s. How little I knew.

Take it or Leave It

If Sheila had agreed to publish me, would I have made my characters capital-B Black? Invented some Queer aliens? Maybe liquidated some bourgeoisie? I like to think I’m above peer pressure, but in reality, I would have tried to toe the party line. I would have torn myself up inside as the Party grew more demanding and the Line swept leftward. Probably, like most of my cohort, I would have just stopped writing.

You can’t let inspiration shine through you and self-censor at the same time. Many people choose censorship, and I can’t blame them. They live in a country where you can lose your job for writing something that makes the wrong person laugh. Americans brag about going “zero-contact” with crime-thinking family members. I, on the other hand, am lucky to live in Bulgaria, where I am self-employed and married to a woman who knows what Socialism does to people.

It’s a good thing, I suppose, that Sheila didn’t choose me. She had her own problems, and although it was independent at the time, her publishing house was soon purchased by a wholly-owned subsidiary of a Beijing-based media group. My own publisher would go on to become a “strategic partner” of Hachette, one of the Big Five that consolidated the market in the last thirty years. They monetize IPs, exploit backlists, and acquire portfolios of assets. They don’t, you’ll notice, sell books.

The Industry Doesn’t Work

Books, to the Industry, are at best investment instruments, at worst tokens in a financial shell game. Flametree, angling for strategic partners to woo, bought the rights to a sequel before my first book had sold a single copy, and insisted this time on the audio rights, too. They had no intention of producing an audiobook, but they wanted an Excel graph they could point to when Hachette came calling.

I wrote them their sequel.

My agent told me it was better to accept a bad deal than suffer a yearlong gap in my publishing resume, so I performed. I whipped up a novel in the time it took my editor to respond to one of my emails (6 months), and it was better than the first one. But, when the sales numbers came in, wouldn’t you know it? The line between books one and two trended down. Potential acquirers wouldn’t like that.

No more book offers from Flametree. “The numbers just don’t justify it,” said the guys with a two-point trend-line. Those statistical stallions.

My agent pressed the dull point home:

“So … what we’ve come to here is a challenging part in your career… what you really need to do is find your audience, and I would recommend delaying taking out any manuscripts until we’ve successfully done that.”

No, she wasn’t officially firing me. She would just no longer take on my work until … I was back in the graces of the flattening tastemakers.

You Work

My reply was obvious, but it took me six months to muster up the bravery to actually say it. For half a year – one editor-reply-period – I wondered if I should give up.

Instead I asked my question:

“If I do learn how to market and sell my own books to my own audience, what do I need you for?”

My agent’s answer was the standard one: cover art, printing, distribution. Except I know people who make better cover art than anything you see on traditional books. Amazon POD makes it too easy to print and distribute your books. And that’s the kindergarten level. The real elite self-publishers are capable of paying editors, artists, and designers, and signing contracts with printers and book distributors.

It’s been four years since then, and I’ve wandered the wilderness hard.3 Now I’m here to tell you, in the most grizzled way possible, why the Industry is in ruins, and what we have to build instead.

The Great and Powerful Backlist

My agent didn’t mention legitimacy. That would have been gauche, and, by 2022, a little embarrassing. Other people have already written about the Industry’s vicious purity tests, its smothering ideological monoculture, its systemic exclusion of young, white men. That’s all true, but paints too cheery a picture. If the Publishing Industry were merely a gray Marxist yoke across the necks of suffering writers, it might produce some books worth reading.

For the true scope of the desolation, see U.S. v. Bertelsmann SE & CO. KGaA, et al., in which the US Justice Department blocked the merger of Penguin Random House and Simon & Schuster. The court documents show us some of what’s going in Big 5 executives’ minds and on their spreadsheets.

Markus Dohle, then-CEO of Penguin Random House, testified that, “Publishers are ‘angel investors’ that ‘invest every year in thousands of ideas and dreams, and only a few make it to the top.’”4 That sounds reasonable, even poetic, until you remember that there is a whole industry of angel investors, and Dohle isn’t part of it. Real angel investors take equity stakes. 21st century Big 5 executives latch onto the accumulated capital of a century of work, and they suck it dry.

They don’t say so, of course. In the words of Madeline McIntosh, the other former-CEO of Penguin Random House: “The fact that we [Penguin Random House] have the largest and richest backlist in the industry is what gives us the latitude to take risks with new acquisitions every day.”5

Penguin Random House published George Orwell, Roald Dahl and P.G. Wodehouse, authors who are all still famous and all – as of this piece – still dead. That means the publisher doesn’t have to send anyone a cut of the profit. Those old books are much better assets than the works of an untested, unpredictable (and un-dead?) living author. If Dahl’s wicked sense of humor offends the current crop of readers, why, there’s always censorship.

So, You Want to Be an Orwell

Where did that backlist come from, Madeline? Dahl, Orwell, and Wodehouse were at one point dumb kids who couldn’t write. They learned how, yes, because of deep desires burning in their bosoms, but why novels? Why didn’t Dahl write intelligence reports, Orwell op-eds, and Wodehouse newspaper columns? They thought someone might buy their books.

But if you are a new Dahl or Orwell today, and you want someone to buy your books …

They won’t.

“Books below [expected sales over 25,000 units or advances over $150,000] received ‘only a contact in the publicity department, smaller book tours (if any), and limited media engagement.’” (p. 34-35)

So don’t quit your day job, kid. You won’t get any marketing or editing unless you have a six-figure advance, and you won’t get a six-figure advance, because the Big 5 actively fix prices (p. 14-15). It’s easy to collude when there are only five of you.

This was all still in 2022. In 2023, Simon & Schuster was sold by Paramount to private equity firm KKR for $1.62 billion. “Sorry, boys,” says Paramount, “the numbers just don’t justify keeping you.”

What Seed Corn?

Remember that time wise old Stephen King rose up and issued this fiery, scathing rebuke?

It’s all in the facial expression and tone of voice. You had to be there.6

In other words, the traditional publishing industry is a hollow shell. The Five Biggies can squeeze their big-name authors living and dead, and they don’t need anybody else.

Let’s say it takes seven years for a writer to train up to the point where he’s good enough to write a best-selling novel. Let’s also say that people don’t train for seven years unless they have some incentive to do so. Industry executives have removed that incentive. Now, as the 20th century’s last crop of big names die, there is nobody left to write anything.

What new books have you enjoyed in the last ten years? Did you find them easily?

I didn’t.

The authors we grew up on have lost their minds, sold their souls, or given up on writing at all. Because why should they write?

Publishers don’t sell their books.

These are the numbers for store sales of physical books published by the top ten Anglosphere publishers in 2022. Yes, third largest category is fewer than 12 books sold, but that’s not the worst part. If we lump this embarrassing figure in with the largest category, we find that 56.1% of new books in the core of traditional publishing’s competence (paper books in brick-and-mortar stores) sell fewer than a thousand copies. For comparison, a thousand copies is half the average print run in the Czech Republic. A thousand copies is essentially none at all.

And here are revenues from book sales. That trendline since 2008 doesn’t look so good. Not something I’d put on my resume, if I’d done that. The picture gets worse if you compare 2024 to 1992. 1992 saw A Fire Upon the Deep and Snow Crash, while 2024 gave us the stultifying The Mercy of Gods as well as Womb City, which apparently has “gender-expansive feminist rage.”

Just copy-pasting that last quote depressed me, but there’s good news. We no longer have to face the choice between toeing the party line and starving out in the cold. You think the Party has food and heat for you? The Industry doesn’t sell books, it can’t sell books. It’s in ruins. You might as well learn to like the great outdoors, because now, that’s where everyone lives.

The Outer Darkness

We’re in good company. Just in the past two years I’ve had the privilege of reading new books that work, whose authors held out against witch hunts, dopamine addiction, and the utter lack of any financial incentive. John C. Wright emerged from the contempt Tor gave him to write series after series of big-idea adventures that don’t just refrain from punishing, but actively celebrate the male reader. Travis J.I. Corcoran indulges my Randian fantasies of just floating away from the oppressive managerial state, and Karl K. Gallagher gives the Censor a good drubbing for me. Theft of Fire is actually hot. And that’s just in scifi. To really get me in trouble, ask me about my taste in contemporary literary fiction.7

Since my own exit, I’ve self-published books that would never have stood a chance in trad-pub, about such things as Christian terrorists, Pagan cults, and a disastrous pet-napping heist run out of the kitchen of an inter-species UN. I kickstarted a comic about an “Anglo” boy who teams up with a Haitian shaman to free his people in a post-apocalyptic future.8 My collaborators on that project come from three different countries and we agree about nothing politically, but that’s not what matters. What matters is that the story works, the art is beautiful, and our project was 200% funded in less than a day, at $20,000.

The Lost Reader

Good for me, but where can you buy those books? You have to sift through Royal Road or, God help you, Kindle Unlimited to find them. The Kickstarter is closed, and you can’t even buy that Haitian shaman comic.

There used to be a time when you could go to a library, run your fingers down the line of plastic-encased book spines, snag the one with a rocket ship sticker, and open it with a better-than-even chance of liking what was inside. Now, you spend hours every week reading book reviews, hitting up your friends for recommendations, trying to prompt around an AI’s political guardrails so it will tell you whether the latest BookTok craze is actually agitprop9 or just very badly written.

What readers need is a filter between them and the great mass of writing. They need someone with the taste to discriminate between good and bad, and the authority to apply it. This trust is in high demand, but currently unmet: an opportunity.

The writers I recommended above are all independent, but I’ve heard of them because they’ve built structures around themselves like little publishing houses. Devon Eriksen created an LLC to hire specialists for editing, art, audio, and distribution. Karl Gallagher and his wife started a family company. They actually sell books.

Back to Work

In a way, the marketers were right. The real work does begin after the book is finished. The question is, who is working for whom? And for what? You made this story and readers need this story, but somebody has to build the bridge between them.

1. First, take your writing seriously. Would you write a manuscript and then file it away in a cabinet in your house? That’s a hobby. Would you write a manuscript and fire it through a cannon directly into the brains of all your neighbors? That’s a profession. You love your reader and you know what’s good for them, which is to read your books.

   Books that you have to write. Every day. Finish that novel and start the next one. Then stop, keep some energy aside for the necessary work of paying invoices, interviewing marketers, and carrying heavy boxes back and forth from the post office. Twenty percent of your work should support the other eighty percent.

2. Find the overlap between what you like doing and what makes money. Too much of the first and you’re back in hobby territory again, designing one alien lifeform or alternate-history language after another, to the interest of nobody. Too much of the other, and you’ll teach yourself to hate your art and you’ll burn out. You got to do both.

3. Get good.10 Fall upon every information source like a starving corsair and steal every piece of good advice you can find. After that, Thomas Umstattd’s AI tools are multifarious and well worth the $10 price of subscription. Go to the “AI Thomas” tool and ask “what are all the steps I need to go through from finished manuscript to printed book in the purchaser’s hands?” Then just do it.

4. Finally, once you’ve got yourself figured out, find people you can trust and work with them. Both of those are important, too: trust and work. Potential readers trust you when they agree to add their emails to your mailing list.11 Fans trust you when they open your next book. Your cover-artist trusts you not to fire him when you find out who he voted for. All of you share in the belief that the next book you write will be worth spending time on.

It’s sad that the publishers aren’t publishing and the editors aren’t editing. Sad, but no longer important. We’re still reading. We’re still writing. That’s why we’re lucky.

They made us walk the plank, but it turns out their ship was sinking. And constructed mostly of spreadsheets and loud opinions. We don’t have to put up with that nonsense any more. We can build something real here, as we swim with half the population of the world.

Welcome to All Hands on Deck—a special podcast for Tortuga Society members and Tortuga Media paychads.

These are recordings of Tortuga’s biweekly standup calls, in which our guys convene to update the group on progress with job stacking and assorted ventures, theorycraft business ideas, and shoot the shit on issues of the day.

Most episodes will be available to paid subscribers — our spicer discussions will be exclusive to full Tortuga Society Members.

Topics Include:

• Quarter 1 Newsletter and Substack Growth

• Ports of Tortuga Initiative Launch

• Website Overhaul Project

• 's Professional Update & Additional Contributions

• ’s Novel and Publishing Update

• 's Training and Project Work

• 's Rental House Progress

• Discussion on Leveraging Repair Skills

• 's Electronics Investigation and the Chips Act

• Test Tutoring as a Business Opportunity

• Discussion on HBD and Intelligence Selection

• Genetics, Environment, and Social Ramifications

• The Prerequisite for HBD Debate

• Continuity of Differences and Taxonomy

• Identity and the Term "Latino"

• European DNA in American Indians and Cultural Tracking

• Validation of Older Anthropological Ideas

• Eugenics and Societal Development

• Update on Claude Document and Philosophy Cafe

• Overview of the Qualia Bootstrapping Problem

• The Qualia Bootstrapping Problem and Epistemological Conflict

• Proposed Solution via Expectation Maximization Algorithm

• Criterion for Synchronization and Experience of Imminence

• Challenges and Bias in Resolving the Problem

• Converging Formal Models and Phenomenological Experience

• Ports of Tortuga Survey is below the PayWall!

Read more

Hello Tortugans, and a good morning to those passing through our shores today.

Today, we bring to you our second official newsletter; you can check out our previous one here.

This winter has been full of challenges, and our crew is excited to melt away our old troubles and seek some greener vistas in the upcoming months.

As usual, we will we share all the wins we’ve been accumulating, and also share some of our plans that are soon to come to fruition.

The Captain’s Log

This section provides General Updates and an Overall Summary.

I was the first landlubber to jump aboard and join The Tortuga Society nearly two years ago… We had a litany of naysayers & doubters, we were called scammers, we were told our little fantasy group of raiders would never amount to anything.

How we’ve proven them wrong mates!

Nearly two years — it’s hard for your humble Captain to believe. We’ve come so far and where are those same scallywags now? Our crew has filled their coffers with stacks of cash, we’ve successfully placed our bilge rats in high paying roles, four of these pitiless Bucs have written & published novels on our site, and our Pirate hideaway now boasts over 180 members.

It’s been an incredible privilege & honor to serve as your captain you Scurvy Dog Hornswogglin' Scoundrels!

On a personal note: Your playboy wench enjoying Captain is now a married man & a father — how the times have changed lads.

-Theon Ultima

Crew Victories

This section is dedicated to Recent Tortuga Member Wins.

Have a win to share? Post it in our Telegram chat, or message one of the Captains or Admins to be featured.

Captain Codebeard

• Released a recipe app: “My app can import recipes from anything! Snap a picture, and boom — you have a searchable recipe.”

• Officially began job-stacking this past quarter!

• Started yet another job; this time as data science contractor.

Wonder

• Secured a job that pays 50% more using Tortuga’s professional resources.

Council Victories

This section is dedicated to Recent Tortuga Admin Wins.

Want to contribute to larger organizational efforts? Have specific questions about internal progress or highlights? Send us a message, or post a comment or question on this post.

• We welcomed 17 new members into our society since our last newsletter.

• We gained 150+ new subscribers to Tortuga Media in, including many paid subscribers, putting us close to the coveted 1K mark.

• We have successfully hosted many talented individuals as a part of our “Special Guest Stand-Up Calls”.

  • These include , , , and

  • We’re have quite a few openings for upcoming special guests, so if you’re interested chatting with the guys, please get in touch.

• We recently formed a brand new Tortuga Privy Council that will be closely supporting the admin team in its endeavors moving forward. The individuals chosen have demonstrate great loyalty and enthusiasm toward Tortuga’s endeavors. They include:

  • and : Head of Tortuga’s publishing and creative writing efforts

  • and : Head of Tortuga’s technology stack and technical learning materials

  • : Tortuga’s marketing lead

  • : Tortuga’s chief business and academic advisor

• We are now hosting many of our published authors’ works on our website. Please check out these excellent novels and support their ongoing creative work.

Great Posts From The Crew

Below are listed some of the best essays & podcasts from Tortuga members over the past several weeks.

The Proper Attitude for Prose Stylists –

Krug argues that the MFA workshop culture of agonizing over every word has quietly strangled English prose, and that the right model for a serious writer isn't the painstaking craftsman but the improvisational musician — someone who has internalized the instrument so deeply that thought and expression become one. A rich, inspiring manifesto for writers who actually want to write.

Costco’s Secret Weapon –

Professor Axelrod makes the sharp and underappreciated case that Costco's true competitive advantage over Walmart isn't the hot dogs or the membership loyalty loop — it's that the membership model functions as an anti-theft mechanism, quietly shielding them from the retail "shrinkage" epidemic that has gutted their competitors in an era of decriminalized shoplifting. Funny, sharp, and more politically observant than a piece about bulk toilet paper has any right to be.

You Should Be Shooting More Karens, Anon –

Bingo Bobbins brings spicy and salacious interpretation to the events that transpired in Minneapolis leading to Rene Good’s timely end.

The 1911 Project –

Tom Swift diagnoses the modern West as intellectually post-Classic: drowning in data but incapable of the serious, standards-driven debate that animated the Victorian educated class. He proposes a “Great Restoration” anchored in classical formation, honest epistemic standards across the ideological spectrum, and the pursuit of two civilizational frontiers — the deep ocean and space — as the engines that will drive the next heroic age.

Mayor Mamdani’s Zoomette Art Hoe Wife Found Liking Nick Fuentes Clips on Instagram –

A short, sharp piece of gonzo gossip reporting on NYC Mayor Zohran Mamdani's wife Rama Duwaji, whose anonymous Instagram account was allegedly caught deep in a Nick Fuentes like-spree. Ringleader delivers the scoop with maximum irreverence and minimum restraint — and yes, Fuentes did respond on Signal."

I’m Going to Have Sex With My Bitcoin –

CSW goes full cryptorotica in this deranged and surprisingly coherent love letter to Bitcoin — tracing the full arc of western sexual liberation from boomers to furries to AI, before arriving at his inevitable conclusion: that BTC, scarce, volatile, ungovernable, and immune to sweet talk, is the perfect postmodern lover. Diamond hands as foreplay; the blockchain as wedding vows.

Debunking Alex Nowrasteh’s Research on Immigrant Assimilation –

Simon L takes a scalpel to the Cato Institute's widely-cited claim that immigrants politically assimilate by the 2nd or 4th generation, exposing a fatal methodological flaw

Five Things to Do Before You Buy the Ring –

Noah Revoy makes the sharp observation that modern courtship unfolds almost entirely inside comfort — restaurants, couches, climate-controlled rooms — meaning couples often marry a version of each other that only exists when everything is going well. His antidote: five deliberately stressful pre-engagement tests designed to strip away the courtship mask and reveal actual character before you put a ring on it.

Fiddler’s Green (Chapter 1) –

Nemesis Fiction has begun serializing The 13th grades’ novel, Fiddler’s Green. The book begins with common Western tropes, but those who have read the first chapter will have realized that the Old West of the novel is not the Old West we are familiar with. Texas is an independent nation, at war in Mexico, and Colorado is in another country. An alternate history.

How to Read the Bible –

Top Shelf Theology serves Catholic catechesis with a Cape Cod in hand, arguing that biblical literalism and smug New Atheism are two sides of the same dim coin, while walking through the rich symbolic numerology embedded in scripture — sevens mean covenant, sixes mean failure, forties mean suffering — and wrapping it all up with a surprisingly illuminating tangent on why soldiers rubbed olive oil on themselves before battle, which is exactly why we anoint kings and priests today.

What a French Nobleman Learned From a Tribe of Cannibals (That We Still Haven’t) –

Aion Armstrong takes Montaigne's 1580s essay "On the Cannibals" apart stitch by stitch, asking whether the philosopher was making a genuine case that European "civilization" was more barbaric than the Tupi cannibals of Brazil — or just running the most elaborate Renaissance shitpost in history.

Of Wizards and Walrus-Men –

Daniel M. Bensen delivers a punchy February book roundup from Bulgaria, dispensing with Games People Play (true but stale), praising the first three volumes of Bakker's Second Apocalypse while diagnosing the series as the purest specimen of Gen X nihilism — great at tearing things down, useless at building anything back up.

Butterfly Effect –

joined host to discuss the Solar counterpoint to their previous discussions’ Lunar Donnie Darko — exploring the theme of the limits of Male Agency.

Friends of Tortuga

Below are listed some of the best reads from friends and allies of Tortuga over the past several weeks.

Your Gym Should be a Temple – by

A Short History of the Gender Wars – by

Stranger In a Strangeland – by

Conservative breeding revolution: not happening - by

The Cathedral & the Ceiling: Coordination Technologies & Conservative Art - by

Molested by Elite Human Capital in Mexico City – by The Calipers

Upcoming Horizons

This section provides a glimpse of our Short-Term Roadmap.

The Tortuga Society has grown and transformed a lot since our initial days! To that end, we are finally planning to expand into the real world this year. The digital world is enticing, but our job is to make both the internet and the physical world a fun place to occupy.

1. We are officially launching The Ports of Tortuga.

   The Ports of Tortuga is an initiative designed to foster local connections and meetups among Tortuga Society members.

   That’s right – we will be hosting our first in person meetups this year. Our privy council is working hard to coordinate with select crew members to kickoff some great in-person activities. (Tortuga members can find the survey behind the paywall at the end of this article)

2. We are in the midst of planning an official Tortuga Publishing platform.

   Tortuga Publishing is here to identify once-in-a-generation literary talent and help them level up both their skills and their sales

   Tortuga has a desire to move beyond just simply featuring great works. We want to be a place where talented guys can get the help they need to launch the creative side of their lives.

You’ll hear more about both of these efforts in the upcoming months.

Closing Notes From Tortuga’s Leaders

Damn it feels good to be a Tortugan — we’ve got so much on the horizon mates. If you’re not a full member yet what’re you waiting for? Reach out to me a Theonultima@tortugasociety.biz if you have any questions.

Pluribus Inservimus!

— Theon & Rajeev

Ports of Tortuga Survey For Full Members!

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Welcome to All Hands on Deck—a special podcast for Tortuga Society members and Tortuga Media paychads.

These are recordings of Tortuga’s biweekly standup calls, in which our guys convene to update the group on progress with job stacking and assorted ventures, theorycraft business ideas, and shoot the shit on issues of the day.

Most episodes will be available to paid subscribers — our spicer discussions will be exclusive to full Tortuga Society Members.

Topics Include:

• Introduction and Announcement of Ports of Tortuga — Tortuga’s distributed local get together infrastructure

• ’s Writing and Publishing Update

• ’s Staffing and Personal Focus

• ’s Marketing and Website Development

• Tortuga Stand-up Call Schedule Change (First call of the week alternates Tuesday 8pm est then Monday 6:30pm est.)

• First Writer Workshop Call Announcement - lead by

• Discussion on Current Events (The Straits and US Politics)

• ’s Gaming Projects

• Tortugan Engagement with Platforms

• Substack Engagement Preferences

• Future Strategy for Tortuga Platforms

• Appreciation for Special Guest Calls

• Value of Call Archives

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Welcome to All Hands on Deck—a special podcast for Tortuga Society members and Tortuga Media paychads.

These are recordings of Tortuga’s biweekly standup calls, in which our guys convene to update the group on progress with job stacking and assorted ventures, theorycraft business ideas, and shoot the shit on issues of the day.

Most episodes will be available to paid subscribers — our spicer discussions will be exclusive to full Tortuga Society Members.

Topics Include:

• Introduction and Announcement of Ports of Tortuga — Tortuga’s distributed local get together infrastructure

• Tortuga Media Updates and Q1 Newsletter

• Contextualizing the Mercor Security Breach

• Competitive Job Landscape and Contract Strategy

• Identified Culprits and Leadership Meeting Status

• Opportunity for Quality Candidates and Future Hiring

• Discussion on Video Games and Anti-Woke Revolution

• Discussion on Four Corners Nationalism and Balkanization

• Discussion on Pan-European Nationalism and Regional Identity

• Concerns about Tourism, Crime, and Demographic Issues in Barcelona

• Debate on European Unity and Geopolitical Strategy

• Assessment of European Leadership and Political Realignment

• Comparison of Social and Demographic Situations in Europe and the US

• Discussion on Europe as an Open-Air Museum and American Investment

• Migration and Cultural Dynamics in Spain

Read more

If you do want to DIY, I respect that. Just understand what you’re signing up for: resume writing is basically marketing, but the product is you, and the customer has the attention span of a goldfish. That said, this guide is going to help you build a resume that gets read, makes sense quickly, and gets you interviews.

What the hell is a resume, anyway?

First, let’s start with the opposite: a resume is not a diary of everything you’ve ever done.

Nobody cares that you are super smart, and aced college while completing a sub-1 hour Minecraft speed run during class (all while having a 9-inch dick). Well, actually, we care and applaud you: but, sadly, HR McKaren does not.

Alright, so what is a resume, then? It’s a one to two page document designed to answer three questions, quickly:

1. Can you do the job?

2. Have you done similar work before, or close enough?

3. Do you look like someone worth spending 30 minutes interviewing?

That’s it. Your goal is not to impress the applicant tracking system with buzzwords and vibes. Your goal is to make a real person say “okay, I get it” in under ten seconds.

How do you get the largest number of people to that point? There is a simple flow that works best, and continues to work for the hundreds of clients I serve.

The flow that reliably wins

Are you ready?

Here’s how the content should be organized so that is reads clean and builds a compelling “yes”, to even the most intransigent girlboss.

1. Clean layout: this make the page scannable

2. Strong top third of page one: this makes the information land instantly

3. Bullets that show value: not ones that show you’re good at tasks

4. Proof and specificity: detailed numbers, scope, outcomes

5. Skills that match the job posting: not personality traits nor fancy adjectives

That’s what we’ll cover. Afterward, I’ll briefly spend some words on:

6. Debugging: how to identify and fix the stuff that silently ruins resumes)

7. Examples and further resources

Let’s dive in!

1. Write for the human eye first and foremost

One of the biggest shortcomings I see on resumes I get, whether from society members or from the outside, is that people are not crafting their resume with the human eye in mind. You pack in all the buzz words, optimize your keywords, what have you, but if you forget to ask the simple question “Does this look good?” you’re severely hindering your success rate.

As automated as the job application process is nowadays, ultimately a person is going to end up looking at your resume, and probably just for a few seconds at that, before sorting it into one of several groups. You need the important points to pop immediately and be easy to read and digest. This is not just about sentence flow. It’s the literal design and layout.

Too often I see people:

• Include photos: never!

• Use “fun” colors: not actually fun!

• Try to cram what should be a comfortable two pager into one page because “a resume should be one page” (two pages are completely acceptable)

You must internalize that the way to standing out is not by displaying originality. Standing out means being clean, clear, and immediately readable. Thus,

Keep it clean, professional, and simple:

• Use a professional font. Times New Roman and Helvetica are safe. Plenty of other clean fonts work too. Just do not get creative with novelty fonts (sorry Wingdings), or weak fonts like Calibri.

• Make section headers obvious. Bold headers like Education, Work Experience, and Skills. Add a strong divider line under each header so the document is easy to scan.

• Left align almost everything. People read left to right. At most, center your name and contact info at the top. Otherwise, keep it left aligned.

• Design for scanning. Put yourself in the hiring manager’s position. If it takes effort to find your company names, titles, dates, or top accomplishments, you’re losing.

2. The top third of page usually makes or breaks you

What to include up top

• Name + location + phone + email + LinkedIn

• A short summary; optional, but useful if you’re pivoting roles)

• A skills line that matches the job

Summary guidance

• Keep it 2 to 3 lines.

• Mention your role identity, scope, and a real strength area.

Example:

Operations coordinator with experience supporting cross functional teams, improving workflows, and maintaining clean reporting in fast moving environments. Known for reducing confusion through clear process ownership and consistent follow through.

Use language that sounds like results, not job descriptions

Aesthetics alone will not be enough to win you that interview. The language you use has to be active and clear. Flaccid or clunky language, too many buzzwords, poorly written bullets, and trying to sound overly eloquent are all things that weaken your resume. You want confident, direct writing that shows impact.

Start every bullet with an active verb that shows ownership

• Strong options: Led, built, improved, launched, streamlined, resolved, negotiated, delivered, increased, reduced, trained, implemented, coordinated, analyzed, designed, optimized.

• Weak options to avoid: Responsible for, helped with, assisted, worked on, was involved in.

• Keep tense consistent.

◦ Current job: present tense (manage, lead, coordinate)
◦ Past jobs: past tense (managed, led, coordinated)

Attach a purpose or outcome. If a bullet ends and the reader still wonders “so what?” rewrite it.

3. Write bullets that demonstrate value

Most people write about their duties. Being a workhorse is not a virtue. Being someone that moves the needle actually means something.

Use this structure: Verb + what you did + how you did it + result

Examples:

• Reduced invoice processing time by 30% by rebuilding the tracker and clarifying owner handoffs across teams.

• Trained five new hires on onboarding workflows, cutting ramp up time from four weeks to two.

• Managed scheduling and communication for a 12 person team across rotating shifts.

• Built Excel dashboards using pivot tables and lookups to track KPIs and flag exceptions.

Quick rules to incorporate

• One idea per bullet. If you have three commas and two “and”s, you’re probably cramming.

• Cut filler words. If you can delete a phrase without changing meaning, delete it.

• Avoid internal jargon. If your bullet only makes sense to your current company, rewrite it in plain language.

4. Use numbers when they help

Quantifying your work makes it believable fast. You do not need insane stats. Use what you actually know and keep it relevant.

Good things to quantify:

• Volume: calls per day, tickets per week, accounts managed, reports built

• Time: hours saved, turnaround time, deadlines hit

• Money: budget managed, revenue influenced, costs reduced

• Quality: error reduction, compliance rate, fewer escalations

• People: team size, trainees, stakeholders supported

If you are not sure of an exact number, do not make it up. Use honest scope language:

• Handled 30 to 50 customer requests daily during peak periods.

• Supported a team of roughly ten with scheduling, reporting, and coordination.

Alright, at this point, save you internalized the basics? At this point, I expect that you can do a first pass of edits and vastly improve your resume.

Once you finish that, proceed below: now we need to work on the most important part: how not to fuckup your resume in a hundred small ways.

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Watch my daddy in bed a-dyin’
Watched his hair been turnin’ grey, yeah
He’s been workin’ and slavin’ his life away
I know he’s been workin’ so hard

We gotta get out of this place
If it’s the last thing we ever do
We gotta get out of this place
‘Cause girl, there’s a better life for me and you
- We Gotta Get Out Of This Place, The Animals

It was only a few minutes after my last article on taxes before people started asking me what to for situations where they had multiple income sources. This is common enough really - you might have a rental house from which you derive some landlord income, you might have a side business, you might have a consulting gig from time to time, you might just drive for Uber on the weekends (this doesn’t generally net you much anymore but for a while people used to pull in some spending cash this way if you were in the right city). Of course, the Tortuga crowd has traditionally emphasized job stacking - which if you’ve got the energy and agency to do so, can certainly put you ahead on the income bracket for a while, and could let you bootstrap your way into one of the other options like building a real estate portfolio or dividend income or the like. (Really though: if you’re going to do that, you should plan to only do it for a finite period of time and typically for a particular goal like buying your house or building your investment portfolio to a certain target value or clearing your debts or whatever - or perhaps for a certain duration - it’s awfully easy to burn out otherwise if you make it your lifestyle for a long time frame.)

Or, hell, a business built on vending machines or a laundromat, who am I to judge? I know people who have made a solid income stream out of both of those - not my cup of tea, but they seem to find it workable, and as I’ve been told endlessly: “beats hanging drywall!” (yeah, I bet!)

There’s also a section on how to maximize the multiple-income-stream lifestyle paired with the stay-at-home spouse for those of you looking to do the trad homemaker sort of life. It may be aspirational - it may be a good thing to plan to “move into” as you start to build a family - the concept of being an “Etsy mom” instead of a part time RN or substitute teacher is perhaps attractive to some, but the thought of also just focusing on running the family and the household (or maybe the volunteer and charity efforts, depending on your inclinations and income level) is probably something that appeals to many.

And - at special request - I’m taking a look at how a couple of high profile people managed to use the Traditional IRA and Roth IRA systems to each grow an absolutely huge tax free savings: Mitt Romney and Peter Thiel.

So… when you start complicating things with multiple streams of income… what’s different?

Tax planning becomes more complex with multiple income sources because your total combined income determines your overall tax bracket, potential underwithholding or overwithholding, and eligibility for certain deductions or credits. The IRS treats all income as part of your adjusted gross income (AGI), but each type has unique rules for reporting, taxation, deductions, and payments. Under current 2026 laws (including permanent extensions from the 2017 TCJA and the One Big Beautiful Bill Act, or BBB), key brackets are progressive (10% to 37%), with the top rate kicking in over $626,350 for single filers or $751,600 for married filing jointly. Long-term capital gains rates are 0%, 15%, or 20% based on income thresholds. Standard deductions are $15,750 (single), $31,500 (married filing jointly), or $23,625 (head of household). State taxes may (usually do) add layers, but this focuses on federal tax implications. Use this document as a baseline and also consult with a tax professional - especially if you have to deal with state taxes.

You’ll report everything on Form 1040, attaching schedules as needed (e.g., Schedule C for 1099 business income, Schedule E for rentals). Common pitfalls include underpaying estimated taxes (leading to penalties) or missing deductions. Strategies like adjusting Form W-4 withholdings, making quarterly payments, and maximizing retirement contributions can help. Use the IRS Tax Withholding Estimator for personalization.

There are some key tax planning differences with multiple income sources. The sort of obvious one involves combined income pushing you up into another tax bracket, because income from all sources adds up, which often kicks you into a higher bracket where more of your earnings are taxed at elevated rates (e.g., from 22% to 24%). Cold consolation that only the portion above the threshold is taxed higher. (This is easy to fall prey to if you’re running pass-through entities like S-corps or LLCs with S-elections - a recent Tortuga all-hands call had Theon Ultima lamenting exactly that “problem”.) Next major one is going to be withholding vs estimated payments: W-2 jobs automatically withhold taxes, but this assumes it’s your only income - so, multiple sources often lead to underwithholding since there’s an assumption of default deduction. Non-W-2 income (e.g., 1099 or rentals) requires you to handle payments yourself via quarterly estimates (due April 15, June 15, Sept. 15, Jan. 15 - do not miss these dates, the IRS is unfriendly about this) to cover at least 90% of your liability or 100%-110% of last year’s tax (higher if AGI >$150,000). And don’t forget self-employment tax: which applies to 1099 income (15.3% on net earnings: 12.4% Social Security up to $176,100 wage base, 2.9% Medicare unlimited, plus 0.9% additional Medicare on earnings over $200,000 single/$250,000 joint). Deduct half as an above-the-line adjustment. You’ll definitely want to watch for deductions and offsets: business expenses (Schedule C), rental costs/depreciation (Schedule E), and losses can reduce taxable income. Passive activity rules limit rental losses to passive income unless you qualify as a real estate professional (750+ hours in real estate, which is not actually all that crazy hard to qualify for). Up to $25,000 in rental losses can offset other income if AGI <$150,000 and you actively participate. Beware of the “edge case” additional taxes like Net Investment Income Tax (NIIT, 3.8%) on rentals/investments if your modified AGI >$200,000 single/$250,000 joint - also, there’s additional Medicare tax on high wages/self-employment (and annoyingly, you really don’t get anything in return for that, other than the privilege of helping keep Medicare going).

Let’s also look at the important optimization strategies, which may not surprise you but certainly bear a look to make sure you can take advantage of them if you can. Certainly contribute to retirement (e.g., traditional 401(k) up to $24,500, or SEP-IRA for self-employed up to $70,000 total) to lower AGI. Use HSAs (up to $4,150 single/$8,300 family) for tax-free medical savings. Bunch deductions (e.g., charitable giving) to itemize over the standard deduction. Harvest capital losses to offset gains (and also up to $3,000 per year against ordinary income, which can roll over if you have a lot of losses). Consider QBI deduction (20% on qualified 1099/pass-through income, subject to limits).

The common categories you’ll (tend to) hit:

OK - first requested scenario. Let’s say you have a standard W-2 (paycheck) job - and also landlord income. This is a pretty common thing, which will still cause you heartburn come tax season if you don’t do it right (but also, it’s pretty easy to get it right - because it tends to be pretty predictable!) Just plan for it ahead of time.

Rental income is taxed as ordinary income, added to your W-2 wages, and follows the same brackets. It’s generally passive, so losses are limited to other passive income (carry forward excess), but if you materially participate and AGI <$100,000-$150,000 (phaseout), up to $25,000 can offset W-2 income. There’s no self-employment tax on pure rentals, but NIIT may apply.

As far as planning ahead for this: Track all your expenses (repairs, insurance, property taxes—SALT cap $40,000 under BBB) - a Google Sheet or Excel document is fine, hell, you can just keep all the receipts in a shoebox and give them to your accountant if you don’t mind paying them to unwind it all, but it’s a little silly because this is easy enough to classify yourself. Use depreciation (e.g., 27.5 years for residential) or bonus depreciation for improvements. If short-term (e.g., Airbnb average less than 8 days), it may qualify as active business income, allowing losses to offset W-2 and QBI deduction. Adjust W-4 to withhold more from paycheck for rental income, or pay estimates. Convert to/from personal use carefully—special proration rules apply.

Second requested scenario - for people moonlighting, especially for the Tortuga crowd - honestly, I should have written this the moment I walked in the door there, because several people I have talked to here seem to be getting spanked by the IRS courtesy of holding multiple jobs - but this section is specifically if you have both a conventional W-2 job and 1099 income. Classically this was a paycheck job and a side moonlighting “consulting” gig for a few extra hours or some expert witness work or something (or something you do during the summer while school’s not in session) - these days it can be more aggressive job stacking, some people are holding down several jobs at once and … damn, do you guys ever sleep? Anyway, it’s applicable with multiple 1099s as well.

This mix combines withheld W-2 taxes with self-managed 1099 obligations. Your total income sets brackets, and 1099 adds SE tax, but you get deductions W-2 workers don’t.

My basic tips: Report 1099 on Schedule C; deduct expenses (e.g., supplies, 50% meals through 2025). Claim QBI (20%) if eligible - there’s no phaseouts for most below $182,100 if filing single/$364,200 joint. Use W-4 Step 4(c) to withhold extra from W-2 for SE tax, or pay quarterly (which is essential to avoid penalties, you’re probably going to need to watch for this and make sure you adjust if your earnings are sort of uneven). If your 1099 job is a side gig, track mileage (67 cents/mile in 2026) and home office expenses. Self-employed health insurance is 100% deductible - and that can be a sizable chunk of change these days. Solo 401(k) or SEP-IRA can shelter more than a standard 401(k) - I’ve talked elsewhere about how to use these for disproportionate benefit.

The extremely related (third) scenario for the Tortuga crowd - or even just the classically overworked sort - is when you have two or three jobs - and thus have multiple W-2s.

All W-2 income is combined on Form 1040; each employer withholds independently, often leading to underwithholding since they don’t “see” your other jobs - if you work “evenly” for these other jobs, this will nearly always happen. This can bump you into higher brackets or trigger additional Medicare tax.

As far as planning for this: use W-4 Step 2 checkbox for multiple jobs - it applies higher withholding rates. Or add extra in Step 4(c). If over $176,100 total wages, claim excess Social Security withheld as a credit. No SE tax, but monitor for NIIT if investments involved. Bunch 401(k) contributions across jobs (total limit $24,500).

In all cases, consult a tax pro if your income is over $100,000 - (if you’re successfully job stacking knowledge worker jobs this may be pretty easy) or complex (e.g., multi-state - pretty common for the remote worker). Early planning avoids surprises… start with last year’s return as a baseline, but also if you know that things are going to be a hairball, start before tax season causes everyone to become short on time and patience.

Now, you’re in a little bit different of a situation if the alternate income stream you’re talking about is a pension from your first job (and you’re supplementing it in your second career) - it’s kind of a nice problem to have, mind you, but it’s a bit rare these days. Still, people started poking me about it (it often seems to be the case if you had a government job for a while and retired but still want to work, if so - more power to you). So let’s talk about that, too.

Tax planning for a salary (W-2 income) combined with pension income involves treating both as ordinary income that aggregates to determine your overall tax bracket and liability. Pensions are generally taxable (fully or partially, depending on any after-tax contributions), reported on Form 1099-R, and added to your W-2 wages on Form 1040. This can push you into higher brackets, increase the taxability of Social Security benefits if you’re receiving them, and require proactive withholding adjustments to avoid penalties. Under 2026 rules, including inflation adjustments and provisions from the Big Beautiful Bill (I will never be able to say this with a straight face), key thresholds like standard deductions and a new senior deduction may help offset some impact.

There are some key tax planning differences. Combined income and brackets is of course a major one: both salary and the taxable portion of your pension count as ordinary income, summed for AGI. This total determines your bracket (e.g., 10%-37%), with only the excess over each threshold taxed at the higher rate. For example, if your salary is $60,000 and pension adds $30,000 taxable, your $90,000 total might shift from the 12% to 22% bracket (threshold ~$47,150 single in 2026).

Taxation of pension is going to be one to put careful eyes on. It’s fully taxable if employer-funded with no after-tax contributions; partially nontaxable if you have a cost basis (recover via Simplified Method for most qualified plans - divide basis by expected payments based on age/life expectancy tables). No self-employment tax applies, unlike 1099 income.

Withholding and payments - salary has automatic withholding via W-4, but pensions use optional withholding on Form W-4P (treated like wages unless you elect none). If underwithheld across sources (e.g., owing >$1,000 or <90% of liability), pay quarterly estimates to avoid penalties - pretty much like anything else with the IRS.

As far as additional taxes, high combined income (> $200,000 single/$250,000 joint) may trigger 0.9% additional Medicare tax on wages/pensions or 3.8% NIIT on nonqualified pensions. Also, there’s potential social security impact: if you are receiving social security disbursements alongside, pensions increase “provisional income” (AGI + nontaxable interest + half of social security), potentially taxing up to 85% of benefits if over $25,000 single/$32,000 joint. If that applies to you, there are some senior-specific rules: if you’re 65+ by end of 2025, claim a new BBB-based deduction of up to $6,000 (individual) or $12,000 (joint) above the standard deduction - there’s no itemizing needed, but phases out starting at $75,000 MAGI single/$150,000 joint. Also, standard deduction rises to $16,100 single/$32,200 joint/$24,150 head of household, plus existing extra for 65+ (~$1,950 single/$3,900 joint). RMDs required if 73+ (or 75+ if born 1960+); failure incurs 25% excise tax. (Be careful about that!)

The optimization strategies are going to be similar to what I usually tell you, but there’s some pension-specific material - and I’ll be the first to say there may be other fancy maneuvers beyond what you see here, pensions aren’t my area of expertise, but this should get you in the right ballpark at least. Certainly start by adjusting witholdings: update W-4 for salary to withhold extra, or W-4P for pension to cover the gap - use IRS Tax Withholding Estimator. As ever, retirement contributions are a great way to finesse your tax bill: if still working, max salary deferrals (e.g., 401(k) up to $24,500 + $8,000 catch-up if 50+, or more if 60-63) to lower AGI and offset pension tax. Deductions and credits are always ideal if you can take them: bunch itemized deductions (e.g., SALT up to $40,000 cap under BBB) if exceeding standard; claim senior deduction if eligible. Public safety officers exclude up to $3,000 for health premiums, so you should definitely do that if it applies. And to the extent that you can, there’s going to be some useful things to do with timing and planning. In the broad camp of timing and rollovers, you may want to delay your pension start if possible (yes, I realize this sounds unintuitive, but your payout is likely to be higher if you can do so); rollover lump sums to IRA to defer tax (20% withholding if not direct). For early pensions (<59½), avoid 10% penalty with exceptions like age 55+ separation. And to the extent that you can do multi-year planning for your financial needs - and I realize this isn’t always in the cards, but if you can - forecast RMDs, SS, and salary to stay in lower brackets; consider Roth conversions if your pension is traditional.

If income is high or involves SS/RMDs, consult a tax advisor… rules can vary by pension type (qualified vs. nonqualified).

But for Tortugans in particular - and other folks who might have occasion to draw multiple paychecks at the same time - the employment scenario that will generally frustrate you the most when dealing with the IRS is multiple conventional W-2 jobs, because the system isn’t generally set up to handle it and the assumption is that you haven’t got more than one (so the defaults and withholdings are going to be very much off-base, leaving you having to do a lot of recalculation).

The best ways to mitigate taxes with multiple W-2 jobs focus on two main goals: (1) fixing inaccurate withholding to avoid surprises/penalties, and (2) reducing your actual taxable income through pre-tax accounts and deductions. Multiple employers mean each withholds taxes independently (often assuming you’re their only job - well, it’s ordinarily a pretty safe assumption), which frequently leads to under-withholding overall. You file one Form 1040 combining all W-2s, so total income determines your brackets, but you can still optimize aggressively. Here’s a prioritized list of the most effective, legal strategies (based on 2026 rules):

First, fix your withholding with updated W-4 forms (this is almost certainly going to be your biggest cash-flow fix). Each employer doesn’t know about your other jobs, so you often end up under-withheld and owing money (plus potential underpayment penalties) or over-withheld and giving the IRS that infamous interest-free loan. Use the free IRS Tax Withholding Estimator tool at IRS.gov (enter your paystubs from all jobs). It tells you exactly how to fill out your W-4s. Then, submit a new Form W-4 to each employer. Step 2 (multiple jobs and/or spouse works) - unsurprisingly, use the Multiple Jobs Worksheet, check the box if you have exactly two similar-paying jobs, or add extra withholding (usually on your highest-paying job via Step 4(c)). Check withholding again mid-year or after any pay change. This doesn’t reduce your tax bill - it just prevents surprises and penalties - and the IRS will be happy to hand those out otherwise.

As usual, I’ll give you the recommendation to maximize pre-tax retirement contributions across all jobs. This directly lowers your W-2 taxable wages right away (and builds wealth, which is what you are actually after, as much as we’re sort of in the game of mitigating taxes - this is all actually so you can build your wealth, after all).

There’s the 401(k)/403(b): the 2026 employee deferral limit is $24,500 total across all plans (plus $8,000 catch-up if 50+, or higher $11,250 catch-up if age 60–63). You can split contributions between jobs if needed. Now, there’s a huge advantage of multiple jobs: Employer matches are calculated separately per plan. Max out matches from every employer for free money (not limited by your $24,500). Overall annual additions limit per plan is $72,000 (your deferral + employer match + any after-tax). Also, you may have access to the 457(b) plans (governmental or certain nonprofit jobs): These have a separate $24,500 limit - so this is a perfect double-dip if you have one. If a plan allows after-tax (non-Roth) contributions, consider a “mega backdoor Roth” for even more tax-free growth. Prioritize getting full matches everywhere, then fill your deferral limit.

Max an HSA (if you’re eligible - this is triple tax-advantaged) - if any job offers a high-deductible health plan (HDHP), the 2026 limits are roughly $4,400–$4,450 self-only or $8,750–$8,950 family (+$1,000 catch-up if 55+). Contributions are pre-tax (or deductible), growth is tax-free, and qualified medical withdrawals are tax-free. It’s probably the best “hack” available to W-2 employees. You usually can’t pair this with an FSA on the same plan.

There are some other quick wins to look for if you can. FSA (Flexible Spending Account) lets you use pre-tax dollars for medical or dependent-care expenses if offered by any employer (use-it-or-lose-it rules apply). Social Security over-withholding: If your combined wages exceed the 2026 wage base (~$184,500), the excess Social Security tax withheld gets refunded automatically on your return. Itemized deductions or credits: Bunch charitable donations (or use a donor-advised fund), mortgage interest, etc., if they beat the standard deduction. Claim all available credits (child tax credit, education credits, etc.). Above-the-line deductions: Student loan interest, etc.

Less quick but still very useful… let’s call them advanced options (for higher combined income) would include topics that you have probably already heard me talk about, but I’m going to mention again because you should certainly consider all three of these: tax-loss harvesting in brokerage accounts, real estate strategies (e.g., short-term rentals with cost segregation or having a spouse qualify as a “real estate professional” to generate passive losses that offset W-2 wages), and you should almost assuredly look to do backdoor Roth IRA contributions. All of these can create bigger reductions but often need a CPA or tax attorney.

As a general rule, you probably want to start with the IRS Withholding Estimator + new W-4s today, then max every pre-tax account available (401(k) deferrals, matches, HSA). This combo usually saves the most money and hassle for people with multiple W-2s. Run the numbers mid-year, and strongly consider a tax professional or good software - especially with recent tax law changes (like the Big Beautiful Bill impacts) and/or if your total income is high. State taxes, local rules, and your exact situation can vary. This is general information, and will generally also benefit from some personalized advice - especially because state tax situations and pension intricacies may be complicating (and you will probably want to be able to make and work against a multi-year plan… at least as much as you can, what with the likelihood of legislators jacking around the tax code again).

The other thing that will frequently throw you off is realized investment gains. If you trade the stock market - I suppose I should say if you successfully trade the stock market, and most particularly if you do so on a short-term-capital-gains basis, you tend to generate income that wildly distorts your tax results for the year. While I will be the first to say this this is a nice problem to have, (hey! you made money! don’t complain!) it can still leave you at very least wincing when April rolls around and you have to write out a big check to the IRS (one hopes you have done proper withholding before then). It is difficult to give any one particular recommendation on this front, but you can certainly engage in tax loss harvesting (selling losses to counterbalance gains) and you can often to a certain extent be judicious about when you book your gains so as to push those into a next quarter or next year - but that’s of course not always possible, the market may not wait for you. It may be feasible for you to hedge a particular stock price (if you think it won’t hold) - a collared transaction can be used specifically to give you time to divest at a certain price point and effectively remove volatility from a stock that otherwise might heavily oscillate; famously, Mark Cuban wisely put an enormous stock collar on his Yahoo shares after selling Broadcast.com and was able to retain billions of value even when Yahoo stock … didn’t retain that value.

Some hopeful Tortugans asked me to comment on the value of job stacking when combined with marriage - so that your wife can focus on being a homemaker (raising the kids, and otherwise being trad). Sure, ok - it’s … actually, pretty much right there in black-and-white: deductions are higher if you’re married; there are additional child credits, and you can also fund your spouse’s IRA contributions.

Married filing jointly (MFJ) is almost always the best status here. It creates a “marriage bonus” for single-income households because deductions, brackets, and many credit limits are roughly doubled without doubling your taxable income.

There is a much higher standard deduction. In 2025: $31,500 for MFJ (vs. $15,750 if single). For 2026, $32,200 for MFJ. This alone can wipe out a big chunk of one spouse’s earnings from taxes. If you’re 65+ or blind, you get extra amounts on top. There are also wider tax brackets, by which I mean income is taxed at lower rates. MFJ brackets are approximately double those for singles, so more of your household income stays in the lower brackets. 2025 MFJ brackets (taxable income after deductions): 10%: $0 – $23,850, 12%: $23,851 – $96,950, 22%: $96,951 – $206,700, and so on (higher brackets also roughly doubled). A single filer with $100k income would hit the 22% bracket much sooner than a MFJ couple with the same household income. Then, you can also do spousal IRA contributions. The working spouse can fund an IRA (Traditional or Roth) for the stay-at-home spouse up to the full annual limit, using the working spouse’s earned income. The 2025 limit: $7,000 per person ($8,000 if age 50+), the 2026 limit is: $7,500 ($8,600 if 50+). Your total combined contributions can’t exceed the working spouse’s compensation (so you can’t do this all off savings, for instance). This is a huge way to build retirement savings (and potentially take a deduction) for the non-working spouse. You must file jointly to qualify. And of course, since you’re in theory doing this for pronatal reasons: Child Tax Credit (CTC) + other family credits (if you have kids). Up to $2,200 per qualifying child under age 17. Up to ~$1,700 of that can be refundable (Additional Child Tax Credit) if you owe little or no tax. Phase-out starts at $400,000 modified AGI for MFJ (exactly double the single threshold of $200,000). You also get better phase-out ranges for the Earned Income Tax Credit (EITC) and other credits when filing jointly.

Don’t forget, of course, the Health Savings Account (HSA) (if you have a qualifying high-deductible health plan): Family contribution limit is higher (~$8,550 in 2025). Triple tax-free: deductible, growth tax-free, and medical withdrawals tax-free. Great for kids’ medical/dental costs. Orthodontics especially add up - although the Invisalign ones are a lot less brutal (at least to wear, and seemingly a little less harsh on the pocketbook) than braces used to be!

Itemized deductions are generally a winner - well, only if they exceed the $31,500 standard deduction - but it does seem like this is not hard to do these days. The one that usually gets you there-or-close is mortgage interest on your home. Also, state & local taxes (SALT) - cap temporarily raised to $40,000 for MFJ in 2025 in some updates. Don’t overlook charitable donations (cash or goods). And you never want to face these, but to the extent that you have them (they do come up) you can deduct unreimbursed medical/dental expenses (only the amount over 7.5% of AGI).

In the annoyingly-similar-name camp we have what are referred to as Above-the-Line Deductions (which reduce AGI even if you take the standard deduction) - so even if you’re not itemizing deductions, these are worth paying attention to… effectively they’re “the even more generally applicable version” of the same thing: Student loan interest (up to $2,500), Traditional IRA/spousal IRA contributions, HSA contributions, Self-employed health insurance deduction (if applicable).

There’s some education-related benefits - (when kids reach college age or if you’re retraining or otherwise taking classes) - American Opportunity Credit (up to $2,500) or Lifetime Learning Credit. Also the 529 plan contributions (growth is tax-free; many states offer extra deductions).

Then there’s some other sort of family-friendly ones that I am going to mention which may be applicable to you. There’s still a bunch of energy-efficient home improvements, solar, or EV credits (some at a state level, some at a federal level). If self-employed or you have a family business: Deduct legitimate business expenses; pay kids under 18 (wages often payroll-tax-free and deductible for you). Child & Dependent Care Credit or Dependent Care FSA - though this is limited if one parent stays home full-time with no work-related care expenses - but if for instance one parent is full time and the other has part time work, you may get a lot of mileage out of it.

Pro tip: max out your pre-tax accounts (401(k), IRA, HSA) first … this lowers your AGI and can help you qualify for more credits or avoid phase-outs. Bunch charitable donations or medical expenses into one year if you’re close to itemizing.Marriage with a stay-at-home spouse and kids usually saves thousands compared to filing single (or even married filing separately). The exact savings depend heavily on your income, number of kids, state of residence, and whether you own a home or have high medical/education costs. Use free IRS tools, TurboTax/H&R Block estimators, or see a tax professional for a precise calculation - especially since rules can have certain sticky points (e.g., qualifying child tests, MAGI calculations). Check IRS Publication 501 or the instructions for Form 1040 for full details.

And then for those of you who have been reading through this article patiently with daydreams of moonshot tax-free growth, yes, you’ve made it to the guide to being Peter Thiel or Mitt Romney:

Let me start with the quick disclaimer - you’re probably not going to be able to replicate either of these. Not because you can’t do the basic maneuver that Thiel did, which is “put a big chunk of founding stock into your Roth IRA” - but because it requires you to then found Paypal and take it through to IPO, and then follow that on by investing in early stage Facebook and see it through to one of the world’s most valuable companies. Friends, if you can do those, the key part is not the Roth IRA - you’d be a billionaire either way! (It’s also nice, sure.)

Peter Thiel leveraged explosive growth in a Roth IRA by using it to hold massive stakes in high-potential, early-stage private companies - primarily his own startup, PayPal, and then later investments like Facebook - where the shares were acquired at extremely low valuations inside the tax-advantaged account. All subsequent appreciation and gains grew tax-free (and remain tax-free on qualified withdrawals after age 59½), turning a small initial contribution into billions without ever paying capital gains taxes on the windfall.

Based on ProPublica’s 2021 investigation (and the IRS guidelines), here’s the key steps on how he did it.

In 1999, Thiel opened a Roth IRA and contributed around $1,700–$2,000 (within the annual limits at the time; his income that year was about $73,000, qualifying him).
He used a self-directed Roth IRA (which allows alternative investments like private company stock, unlike standard brokerage IRAs limited to public securities).

Then, during PayPal’s formation (then called Confinity) - or maybe during early merger phase, I’m not actually clear, Thiel purchased 1.7 million shares through the Roth IRA at a par/founders’ price of just $0.001 per share (a tenth of a penny).

Total cost inside the IRA: $1,700.

This gave the Roth IRA a huge ownership stake in the company right from the start.

Sounds easy enough - he started small, he risked basically a year of his Roth savings (by buying highly illiquid founding shares of Paypal) - and it paid off big.

Well, it turned out that PayPal grew rapidly. When eBay acquired it in 2002 for $1.5 billion, Thiel’s shares (held in the Roth) were worth about $55.5 million—a massive multiplier.

Because the shares were inside the Roth IRA, none of that ~3,200x+ gain was taxed as capital gains. The entire value stayed sheltered.

That’s an excellent start. But what really made Peter Thiel’s name was basically doing this again - from an angel investor / venture capital perspective. You see, Thiel rolled the proceeds into other high-growth private investments. A notable one was an early stake in Facebook (reportedly around $500,000 invested via the Roth).

As Facebook (and other ventures) skyrocketed, the account continued compounding without taxes dragging down returns.

By the end of 2019, the Roth IRA reached $5 billion (up from under $2,000 in 1999), with jumps like $3 billion+ in just a few years from private equity-style gains.

He reportedly made no further contributions after 1999 - basically all growth came from internal investments and appreciation. The power of reinvesting and compounding tax-free is pretty phenomenal, especially when you got in on Facebook, Yelp, SpaceX, Spotify, Palantir, and AirBNB (let’s be fair though - a very disproportionate amount of those gains are from his early investment in Facebook stock).

So, why did this work so well? Well … apart from the outrageous luck factor of hitting the startup lottery twice in a row with Paypal and then Facebook, which is not to be overlooked … there’s some important planning factors here. The first major leverage point is of course the Roth IRA rules: contributions are after-tax, but qualified growth and withdrawals are 100% tax-free - no capital gains, dividends, or distributions taxed if rules followed. Furthermore, doing this in a Roth self-directed structure allowed buying illiquid, pre-IPO/private shares unavailable in regular IRAs.

Combine this with the exceedingly favorable share price available to him: as a founder (well, co-founder), Thiel could buy huge blocks of shares at rock-bottom founders’ prices or valuations that public investors couldn’t access; similarly, when it came time for him to invest in Facebook, the price point he was able to buy in at was far more attractive than what future investors would be able to participate at.

Now, in a taxable account, he’d have paid long-term capital gains (15–20%+) on sales or realizations; in the Roth, zero tax on the billions in appreciation. The lack of tax drag on compounding has been tremendously advantageous over the years. ProPublica dubbed it “Lord of the Roths” and highlighted how this turned a middle-class savings tool into a ultra-wealthy tax shelter, leading to complaints about how this was costing the government potentially billions in lost revenue (which seems like “you did what you were supposed to do but you did it too well!”) by following these rules. I haven’t heard if the proposed wealth taxes target IRAs that are too big, but I suppose I wouldn’t be surprised.

Important caveats (aka, You Probably Can’t Replicate This Exactly) - as noted, this strategy relied on being an insider at hyper-successful startups (first PayPal and then the eBay exit; followed by the even more spectacular return on an early investment in Facebook). Average investors, to put it mildly, lack access to founders’ shares at $0.001 or equivalent.

Self-directed IRAs can hold private stock, but:

1. Valuations must be arm’s-length/fair market (there’s significant IRS scrutiny on self-dealing).

2. Prohibited transactions (e.g., self-dealing with disqualified persons) can disqualify the IRA.

3. Annual contribution limits still apply (~$7,000 in 2025/2026, plus catch-up), so scale comes from growth, not big deposits.

Thiel’s case sparked debate about Roth IRA “abuse” and calls for reforms (e.g., limiting mega-IRAs), but as of 2026, the core mechanics remain legal for those with the right opportunities.In short: Thiel didn’t “hack” the system illegally… he maximally exploited the Roth’s tax-free compounding by loading it with asymmetric, high-upside private equity bets that exploded in value. It’s a masterclass in placing your highest-conviction, highest-growth assets inside the most tax-efficient wrapper possible.

If you’re planning to try to do this: the “disqualified persons” bit is going to potentially be a bugaboo.

A disqualified person for a Roth IRA (or actually any IRA) is an individual or entity closely related to the account owner - such as a spouse, lineal descendant (child/grandchild), ascendant (parent/grandparent), or their spouses - who is prohibited from engaging in transactions with the IRA to prevent self-dealing. Prohibited transactions include buying, selling, or leasing property, or receiving personal benefits from IRA assets. So, for instance, investing in your own company is generally not permitted. OK wise guy, so wait… then how did Thiel do it? Well, for entities, the IRS guidelines are: a corporation, partnership, trust, or estate in which the IRA owner has a 50% or greater interest; for Confinity (nee Paypal) our case study Peter Thiel had a couple partners (Max Levchin and Luke Nosek) - and thus Thiel had an only a minority interest of the company to put into his IRA. But still a very significant chunk, as it turned out.

To be fair… you’re probably not going to be able to replicate Mitt Romney’s strategy either, because you’re probably not going to be in a lead position at a powerful private equity firm. But it’s still instructive to know.

Mitt Romney grew a substantial portion of his wealth in a tax-advantaged retirement account… specifically, a large traditional IRA (not a Roth IRA)… through aggressive use of private equity investments during his time at Bain Capital. Unlike Peter Thiel’s Roth IRA (which allows completely tax-free growth and withdrawals), Romney’s was a pre-tax (traditional) IRA, meaning contributions were tax-deductible, growth was tax-deferred, and withdrawals are taxed as ordinary income. However, the massive appreciation inside the account effectively sheltered enormous gains from immediate taxation, allowing the wealth to compound without annual capital gains taxes.This strategy drew significant attention during his 2012 presidential campaign, when financial disclosures revealed his IRA was valued between $20 million and $102 million (with estimates often cited around $100 million+). More recent analyses (as of the early 2020s) suggest it could be in the range of $25 million to $125 million or even higher, though exact current figures aren’t publicly updated. The key was not exceeding contribution limits illegally but leveraging insider access to high-upside, low-initial-valuation private investments.

As far as the key component of how it worked… well, the one you’re going to have the hardest part with is that Romney co-founded and led Bain Capital from 1984 to 1999 (with some involvement extending later). Bain allowed certain partners and employees (including Romney) to co-invest in the firm’s deals via their retirement accounts, often using a SEP-IRA (Simplified Employee Pension IRA, which permitted higher annual contributions - up to around $30,000 per year during that era - funded by the employer).

So critically, this gave him (and others) access to extremely low-valuation stakes in private deals. This was a pretty sweetheart arrangement. Bain structured investments with multiple share classes. Employees could use their IRAs to buy “Class A” or similar preferred shares (or partnership interests) at very low valuations - sometimes nominal, almost near-zero - because they represented high-risk, future-oriented upside (e.g., carried interest-like profits or profits interests in portfolio companies).

These were often valued using methods like “liquidation value” or future income projections, which experts noted could be significantly below what later proved to be fair market value. When Bain’s deals succeeded (e.g., leveraged buyouts that generated massive returns), these stakes exploded in value inside the IRA.

Naturally, being an IRA, this resulted in tax-free compounding. No capital gains taxes were due on the appreciation while inside the IRA. The entire growth compounded tax-deferred until withdrawal (now required via Required Minimum Distributions since Romney is over age 73). There was also no contribution limit bypass needed -annual limits were followed, but there is no cap on how much an IRA can grow internally through investments. A small initial amount (or modest annual max contributions) could balloon if the underlying assets multiplied dramatically (just as we saw for Thiel).

I should also mention offshore and blocker structures: some Bain funds used offshore entities (e.g., in the Caymans) to help retirement accounts avoid unrelated business income tax (UBIT) that might otherwise apply to leveraged investments - though Romney has stated this provided him no personal tax reduction. It likely wouldn’t have mattered for him, given that this was in his IRA.

By comparison to Peter Thiel’s approach: Thiel used a Roth IRA for similar private equity bets (e.g., ultra-cheap PayPal founders’ shares), achieving true tax-free status on billions in growth. Romney’s traditional IRA deferred taxes but doesn’t eliminate them - distributions are taxed at ordinary income rates (up to ~37%). If Romney had used or converted to a Roth, the wealth would have been even more tax-efficient. (If you’re asking “Why didn’t he? Surely Romney was smart enough and well-advised enough by tax professionals” the answer is that the Roth wasn’t introduced until 1998.) His setup was still extraordinarily advantageous for someone with access to elite private deals unavailable to most investors.

Why this isn’t replicable for most people? Well, pretty sure you know that answer if you’ve read this far. It requires you to be an insider - heck, basically a founding insider - at a top private equity firm to access those low-valuation opportunities. Bain Capital was absolutely top shelf. Further, self-directed IRAs can hold private equity today, but valuations must be arm’s-length and fair market (IRS scrutiny on self-dealing is high). And prohibited transaction rules prevent conflicts (e.g., you can’t invest in your own company in ways that benefit you personally).

Again, this sparked debates and GAO reports on “mega-IRAs,” leading to calls for reforms (e.g., balance caps), but the core rules allowing unlimited internal growth remain.

In essence, Romney maximized tax-deferred compounding by placing asymmetric, high-growth private investments inside his IRA - legal, eyebrow-raising, but reliant on his position at Bain. It’s a prime example of how retirement accounts can become powerful wealth-building tools for those with exceptional investment access, though his wasn’t fully “tax-free” like a Roth. For personalized strategies, consult a tax professional, as rules evolve. Though to be fair, if you’re in a position to pull this off - you probably have already worked it out with your tax professional.

All of that being said… if you are actually going to try and replicate Thiel’s maneuver, you need several co-founders (like Paypal had) - you can’t do this if you own too big a piece of the firm yourself (or with your spouse or your family). I will say - it’s not a bad idea to do it (but I have never done it, or perhaps I should say, I have not yet done it; yes, I have worked out a good blueprint - if I get enough interest, I’ll do an article on how to do that for paid subscribers - or you can ask me about it in Tortuga chat). Romney’s is … easier to do, but it still requires a position of exceptional privilege from which to cleverly stuff your IRA (or potentially Roth IRA) with very strategically undervalued assets. I suspect you could probably do this pretty readily if you didn’t mind the appearance of grift, or if you were in Congress with certain access to privileged information (eg the famous Pelosi Stock Trading record) - but I should advise you against making decisions that will get the IRS or the SEC after you. You want to be able to enjoy your prosperity happily, after all.

Professor Axelrod

Let's see how long it takes to do this again

Welcome to All Hands on Deck—a special podcast for Tortuga Society members and Tortuga Media paychads.

These are recordings of Tortuga’s biweekly standup calls, in which our guys convene to update the group on progress with job stacking and assorted ventures, theorycraft business ideas, and shoot the shit on issues of the day.

Most…

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This week we were joined by who shared his fascinating views on social systems, institutional design, and technological governance; and, importantly, a unique fair to his ideas.

The Calipers

human agronomy, homoerotic terror, hyperreality temples

Welcome to All Hands on Deck—a special podcast for Tortuga Society members and Tortuga Media paychads.

These are recordings of Tortuga’s biweekly standup calls, in which our guys convene to update the group on progress with job stacking and assorted ventures, theorycraft business ideas, and shoot the shit on issues of the day.

Most episodes will be available to paid subscribers — our spicer discussions will be exclusive to full Tortuga Society Members.

Topics Include:

• How did choose his name?

• The Shift from Confirmation Bias to Falsification

• Challenges in Cultivating Empirical Rigor

• Travel as a Productive Tool for Worldview Transformation

• Negotiating Across Different Cultural Contexts

• The Network State Model and Transcending Local Prejudices

• The Mercurian Archetype and Building Mobile Capital

• The Need for Institutional Alternatives and Trustless Systems

• Thinking About Systemic Dysfunction: The Problem of Portable Tap Water

• The Experiential Shift in Worldview

• China's Position in the World Economy

• The Role of Resentment in Former Ethnonationalist Views

• The Struggle Between Appalonian Romanticism and Mercurian Reality

• Tortuga as a Found Family Network State

• Biology, Temperament, and the Limits of Travel

• The Evolution of Ethics and the Question of Usefulness

• The Ethics of LooksMaxxing and Agency

• The Legitimacy of "LooksMaxxing" and Success

• Decoupling of Sex and Reproduction

• Technology and Leveling the Playing Fiel

• The Evolution of Differentiators

• Market Principles as a Guide to Value

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Texans do it because it’s in their blood. Californians do it because they’ve totally committed to the bit of civilizational suicide. New Englanders do it because once a century they rediscover the sensation of being infuriatingly annoying & moralizing at the rest of us.

But there is exactly one region in the continental United States that could plausibly make a real case for separation without sounding like a diabetic county commissioner, and that region is the Four Corners.

Yes, I am completely serious.

The Four Corners has several immediate advantages as the nucleus of a new nation. First, it already possesses the only thing most nationalist projects conspicuously lack, which is an actual conciousness. There is a psychic coherence to that part of the country that anyone with a functioning nervous system can detect within about twenty minutes of being there. The air itself operates under a different constitutional order. The light is harsher, the distances immense and the land looks older than the regime currently squatting atop it.

A proper nationalism can’t begin from abstractions. It has to begin from somewhere that visibly, even viscerally exists.

And the Four Corners exists in a way most of America does not in the current year.

A lot of the modern United States feels like it was assembled by airport consultants and regional hospital administrators (not surprising given the immensity of the tertiary & quaternary economy). The Four Corners still feels geologic. It has cliffs, mesas, red deserts, mountain forests, canyons, rivers, and enough sublime intimidation to cure the bugman of several modern beliefs in a single afternoon. A people formed under those conditions will inevitably differ from a people formed in suburban slurry between a Costco and an arterial road called Heritage Parkway.

The Makeup of the Four Cornerian

The Four Corners is also —in a deep and meaningful sense— a nation of settlers already. Not so much settlers in the old grade-school pageant sense; I mean newcomers in the more elemental sense: people who went there because they had the gumption to leave their homes and seek out a new land (one arrayed with breathtaking sunsets). They were willing to leave behind the lame assurances of home & gamble on vastness, dryness, altitude, and ultimately uncertainty. Whatever else one says about them, that is not the profile of the passive American consumer.

Four Cornerians consciously chose this path — far from simply drifting into it. That critical choice already implies the beginnings of a national type. Remember, all of your dear Tortugan leaders hail from this sacred region: , , and .

One could imagine the usual objections here from low-imagination patriots. “But these are Americans.” Fine. They are Americans in the same way that the colonists were Englishmen up until the point where they concluded they had become something else and that the old arrangement no longer served them. Political identities are not sacred relics. They are contingent bargains. And the American bargain increasingly looks like one in which every distinctive and beautiful place in the country is treated as a warehouse for either extraction or demographic flooding, depending on whether the people ruining it wear fleece vests or construction boots.

This is merely vandalism.

The Four Corners Must Protect it’s Natural Wonders

The liberal wing of the regime insists on mass immigration as a sort of secular sacrament, heedless of whether the receiving landscape can bear the pressure. The right, being right-wing in the stupid American sense rather than the intelligent one, often replies by treating the land itself as a consumable object whose sole moral function is to be drilled, scraped, bulldozed, and monetized by whichever lizard-brained local notable can say “jobs” with the most patriotism in his voice.

So there you have it: one faction that cannot stop importing endless population into fragile terrain, and another that cannot stop imagining every canyon, forest, and watershed as an undeveloped spreadsheet.

Between them, they produce the same result — the Four Corners should reject both

A Four Corners state would have every reason to take conservation seriously as a matter of national continuity.

That land is the nation. Not a backdrop to it. Not a resource adjunct. Not a tourism brochure.

The nation would derive much of its legitimacy from stewarding one of the most visually overwhelming & ecologically delicate landscapes on the continent. If you ruin the land, you ruin the premise.

That alone would put it morally above the current United States, which has perfected the art of building massive parking lots and ugly superstructures.

Reclamation of the Colorado River

The Colorado River.

Any serious discussion of Four Corners sovereignty must immediately become hydraulic.

Control the upper reaches and you stop being a picturesque provincial curiosity. Sourced water reclamation is destiny far more than demographics is. After all, Water in the American Southwest is not some secondary policy concern for bean-counting technocrats. Whoever meaningfully shapes the terms of access to that river will possess leverage over agriculture, development, energy, and regional growth across enormous swaths of the interior West.

People overemphasize the power of aircraft carriers and financial global currency. Often, however, real power is often much simpler: It is chokepoints; It is terrain.; It is who gets to turn the valve.

A Four Corners republic would not need to posture as some global empire it would simply need to understand that possession of a vital watershed in an arid century confers bargaining power far beyond what its population would suggest. Nevada & Southern California, everybody downstream would suddenly discover an intense interest in the opinions of a nation they had formerly regarded as nothing more than scenic beauty.

The 21st century has made one thing embarrassingly clear: states that command indispensable flows do well for themselves. Oil did this for the Gulf. Shipping lanes do it for tiny maritime powers. The Colorado could do a more modest version of the same for our nascent desert polity.

There is also a cultural case.

The Distinct Culture of the Four Corners

A Four Corners nationalism would be one of the only regional nationalisms in America not built on nostalgia for a world gone by. It would not need to summon the ghosts of 1776 every time it wanted to justify itself. It could simply say: we are here now, our land is real, the pressures upon it are real, the failures of Washington are unbearable, and we are more likely to preserve what is valuable than a distant managerial empire split between ideological evangelists and appetitive morons.

It could also cultivate a national myth that isn’t embarrassing. Most political myths in modern America are either too cringe to inspire anyone or too stupid to survive contact with someone above 120IQ. Four Corners Nationalism, by contrast, has decent raw material.

It can speak in the language of the frontier. It can elevate the settler instinct without becoming a parody of the Old West. It can honor risk, self-command, and a form of civic dignity that the rest of America surrendered a long time ago in exchange for convenience & grievance theatre.

It also helps that the region is difficult.

Difficulty is underrated by liberals, feared by conservatives, and indispensable to nationhood.

A people that lives in a place not everyone can handle or have the wherewithal to venture too is far more likely to remain recognizably itself. This is why mountain peoples and desert peoples so often retain stronger characters than the soft inhabitants of rich plains and managerial coasts. The environment imposes terms upon it’s population — a crucible that filters out the weak and ultimately produces limits, and limits are the precondition for overcoming.

The United States increasingly has nothing to overcome because it increasingly recognizes no limits.

Everything must expand. Every market must be opened. Every labor pool must be widened. Every suburb must metastasize. Every local inheritance must be dissolved into national homogeneity or international interchangeability. Americans speak constantly of freedom while living under a regime of relentless flattening. The result is a country where one can drive for hours and learn almost nothing.

The Four Corners need not accept this fate.

It can choose to become the Switzerland of red rock severity. Or the Israel of the West that got it’s killing over with a century ago. Or perhaps something nobler than either. A hard, sparse, beautiful republic of plateaus and canyons whose central political doctrine is simply that not every magnificent piece of land on earth should be handed over to developers, bureaucrats, industrial lobbies, and migration absolutists until it looks like every other failed success story of the modern world.

Would such a nation have problems? Of course. Every nation does. It would need water discipline, border discipline, serious land-use doctrine, and an elite that did not instinctively hate either beauty or power. It would need to resist becoming a playground for rich eco-boomers, a tax dodge for libertarian failsons, or a mystical art colony for women named Sage.

The Bleaching Must Continue Unabated

The grandest project of the Four Corners nation will be the ethnogenesis of a new people.

This cannot happen through sterile civic nationalism or the brittle purity spirals of yesterday’s white nationalism. It will happen through the deliberate continuation of the very process that has already been at work in the Americas for five centuries: bleaching.

The Four Corners does not labor under the crushing statistical burden of a large, permanently alienated Black population. Here, Blacks remain a relatively small share of the demographic map: scattered, contained, and far less central to the daily life of our nation than they are in the old industrial cities or the Deep South.

That single fact removes the most intractable obstacle that has warped every other American conversation about race. Without that overwhelming variable, the path to ethnogenesis becomes realistic, achievable, even likely in a single generation.

Our core population engine is Latin American; especially the Mexican, Central American, and South American streams that already dominate the borderlands and the high desert. These are not distant, unassimilable blocs. They arrive already steeped in the same race realism that built Latin America: mejorar la raza. Marry lighter. Breed lighter. Rise higher. Walk into any prosperous Hispanic neighborhood in the Four Corners and you will see the living proof: proud families who carry the flags of their ancestral republics yet measure success by how closely their children approximate the European phenotype. The most ambitious among them already seek out native-stock Four Corners men as husbands for their daughters, and the most successful sons arrive at ranch weddings with wives who look like they stepped straight out of Castile.

Four Corners nationalism embraces this reality as national policy. Castizo Futurism will be the official aesthetic & reproductive strategy of the state. Religious conversion, cultural immersion, and two generations of strategic miscegenation will fold these populations into the European core of the West exactly as it happened in colonial Mexico, in the Spanish borderlands, and in the early American Southwest. The result will not be a uniform blond monoculture, but a high-trust, high-agency civilization whose median face is several shades lighter, several points higher in civilizational capability, and fiercely loyal to the red-rock republic above all.

To those still clinging to yesterday’s continental white-nationalist frame: relax (srsly). The Anglo-Teutonic interior of the Four Corners: our mountain valleys & high-plains farm belts; they already maintain replacement-plus fertility among religious conservatives. Those corn-fed lineages will supply the demographic ballast that keeps the national phenotype anchored. Coastal transplants and desert-city cosmopolitans can chase their exotic preferences if they wish; the sheer gravitational pull of Four Corners numbers and Four Corners culture will bleach their progeny back toward the European mean. Therefore the Four Corners state shall celebrate mejorar la raza as patriotic sacrament. Tax credits for native-stock men who marry and raise children with high-quality women of assimilable Latin stock. Public art, festivals, and schooling that honor the man who bleaches his line as a founder of the new people. Churches that bless these unions as the literal fulfillment of the Four Corners covenant. Two generations of this policy and the new nation will be born; recognizably Western, unmistakably improved, and unapologetically Four Cornerian .The Bleaching must Continue Unabated — for it will be the birth of empire in the high desert.

Four Corners Nationalsim Now!

But… at least it would be work in service of something visible; And that is more than one can say for the current arrangement.

People hear the word “secession” and imagine war. I hear it and think: perhaps, at long last, someone has looked at a map and a watershed and a stretch of ravishing country and concluded that it ought to really belong first to those willing to take responsibility for it.

The Four Corners already has the land, atmosphere and highly selected population. A latent mythos is developing, as this land sits atop one of the great strategic assets of the American interior. All that remains is the final, almost theological step by which a region ceases to think of itself as an afterthought in somebody else’s country and begins to act like a place worthy of rule.

I see no reason it should remain American forever.

Indeed, I suspect that the single most American thing the Four Corners should do: is leave.

Welcome to All Hands on Deck—a special podcast for Tortuga Society members and Tortuga Media paychads.

These are recordings of Tortuga’s biweekly standup calls, in which our guys convene to update the group on progress with job stacking and assorted ventures, theorycraft business ideas, and shoot the shit on issues of the day.

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Bend Dexter

Home of the foremost writer and thinker of Padukgrad.

By Krug

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This week we were joined by Tortuga’s Staffing CEO and to share some exciting developments for our staffing venture.

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Bend Dexter

Home of the foremost writer and thinker of Padukgrad.

By Krug

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Welcome to All Hands on Deck—a special podcast for Tortuga Society members and Tortuga Media paychads.

These are recordings of Tortuga’s biweekly standup calls, in which our guys convene to update the group on progress with job stacking and assorted ventures, theorycraft business ideas, and shoot the shit on issues of the day.

Most…

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This isn’t an exposé or a conspiracy theory. It’s an attempt to describe what power looks like once it slips free of ordinary limits.

Stanley Kubrick did not make Eyes Wide Shut to suggest that the powerful secretly dress in ceremonial robes or worship gods in hidden chambers. What he depicts instead is the emergence of a distinct moral sphere produced by extreme power, one in which exemption from ordinary consequence is assumed. In Kubrick’s rendering, the masked ceremony at the centre of the film is not erotic pageantry. It represents a domain in which ordinary rules no longer apply, identity becomes fluid, and consequences do not return to those at the top of the hierarchy. Eyes Wide Shut does not advance a conspiracy thesis. It identifies a recurring structural pattern in which power bends social reality until it answers only to itself.

Kubrick maintained distance from this logic in his own life. He withdrew from Hollywood, declined publicity tours, and avoided celebrity social circles. This withdrawal was not motivated by fear of elites as individuals, but by an understanding that proximity to concentrated power alters the conditions of perception. Such proximity reshapes what can be seen, what can be articulated, and what can be risked. Kubrick’s warning is therefore not moralistic, but diagnostic. Power constitutes a distinct order of being, and effective power tends to operate through concealment rather than visibility.

This is the correct way to approach the Jeffrey Epstein saga.

People often ask why Epstein behaved as he did, as though some secret code or private pathology must explain it. Such explanations are unnecessary. Extreme wealth alone is sufficient to reshape how an individual experiences the world. When a person possesses more money than could be spent across multiple lifetimes, money ceases to function as a form of scarcity and instead becomes an ambient condition through which reality is mediated. Constraints that regulate most human behaviour, including risk, exposure, accountability, and social sanction, lose their regulating force. At this stage, behaviour is no longer moderated by consequence but by access, namely access to people, places, narrative control, and institutional protection. In this way, unlimited resources translate directly into expanded latitude of action.

Antidote To Magical Thinking

Not "Learning" - But "Unlearning"

By Sirius White

At this point, the occult frame becomes not merely metaphorical but structurally precise. The term occult refers to that which is hidden, set apart, or removed from ordinary social visibility. Epstein’s world required neither incantations nor deities in order to function as occult. It operated as a closed system governed by enclosure, initiation, and exemption. Those within this environment were not simply participants in wrongdoing. They crossed experiential thresholds that rendered silence more adaptive than exposure. In anthropological terms, this constitutes ritual, understood as a patterned transformation of status within a sealed social space. This structure aligns closely with the classical Hermetic systems, which organise power around separation, restricted access, and the containment of knowledge within bounded domains.

Many dominant narratives fail here. They assume that when wrongdoing becomes visible, individuals will refuse to participate. This misreads both incentive structures and human psychology. Journalist Michael Tracey has explored this failure in relation to Epstein and the broader dynamics by which narratives form around powerful figures. Across his commentary, he has shown how much of what circulates as “Epstein mythology” emerges less from evidentiary rigor than from institutional incentives: sensationalism rewarded, inconvenient facts sidelined, reputations protected. Journalists, politicians, and commentators rationalise their engagement according to career incentives and audience capture rather than sustained scrutiny

At a deeper level, this exposes a more general pattern. Individuals and institutions routinely accept money, access, or proximity to powerful figures even when they privately recognise impropriety. This is not naïveté. It is rationalisation under pressure. Participants tell themselves the resources will be used for good, that responsibility is diffuse, that refusal would only pass the opportunity to someone else. These are not moral failures so much as adaptations to a warped incentive field. Concentrated power generates pressures that shape behaviour across entire networks, extending well beyond any inner circle.

Once enough participants internalise these pressures, silence stops appearing exceptional and stabilises as the normal operating condition.

This is how an occult structure maintains itself: not through witchcraft, but through the distributed consent of those who benefit, fear exclusion, or calculate quietly that participation is safer than opposition. It is a social contract of geometric asymmetry, where the few at the centre extract protection, privilege, or exemption, while the many on the margins tolerate the arrangement because confrontation feels too costly, too risky, or simply pointless.

This pattern is not novel. Secret societies and esoteric organisations have operated according to similar principles for centuries. From the Eleusinian Mysteries to medieval guild structures and later fraternal orders such as Freemasonry, the underlying architecture remains consistent. These systems are characterised by graded initiation, selective disclosure, enforced silence, and the implicit or explicit promise that membership confers insulation from ordinary social rules. Knowledge is never disclosed in its entirety at once. Identity is reshaped incrementally, and each threshold crossed increases the cost of withdrawal, rendering compliance progressively more rational than refusal.

What matters in these systems is not belief, but structure. Initiation binds through experience rather than ideology. Oaths formalise silence, but shame and status do most of the work. Over time, secrecy becomes less a rule than a reflex. These organisations survived not because they were omnipotent, but because they made themselves indispensable to those inside and opaque to those outside. The cost of exposure was always higher than the reward.

Epstein’s world does not resemble a cult because it borrowed from ancient traditions. It resembles them because it obeyed the same underlying laws. Initiation, insulation, silence, and asymmetry are how power learns to endure.

Over time, such structures do more than organise people. They organise space. Secrecy requires geography. Initiation requires thresholds that can be crossed but not easily reversed. Enduring esoteric orders converge on the same principle: separation must become material. A bounded location becomes necessary, one in which normative rules shift upon entry and ordinary oversight loses its reach.

The island that constituted Epstein’s domain is symbolically significant for precisely this reason. An island materialises separation. Alternative rules prevail. Exit is constrained. Jurisdiction weakens. Once space is removed from shared governance, activity within it is regulated by internal logic rather than external accountability. This mirrors the historical function of temples, which operated as liminal zones set apart from everyday life.

Once space is set apart in this way, symbolism accumulates whether anyone intends it or not. Separation generates meaning. An enclosed place becomes charged simply by being unreachable. This is how temples, underworlds, and initiation chambers have always emerged. Not because myths were consciously invented, but because power, once insulated, begins to express itself symbolically.

Across ancient cultures, the sacred was rarely placed at the centre of communal life. It was pushed underground, into caves, crypts, inner chambers, or remote sanctuaries. The underworld was not imagined as evil. It was anterior, older than law, older than speech, older than permission. Entry marked a threshold. Ordinary identity loosened. Something irreversible was understood to occur. These were not places for casual visitation. They altered those who entered them, or refused to let them return unchanged.

That structure persists long after belief fades.

An island reproduces the same conditions. Time behaves differently. Memory shifts. The outside world grows abstract. What happens inside becomes self-contained. Silence becomes easier than explanation. Staying feels safer than leaving.

The abyss here is not a literal void beneath the earth, but a structural condition. It opens wherever accountability weakens. It is the gap between action and consequence. Within that gap, acts become possible that would be unthinkable under ordinary visibility. The abyss does not require belief. Neglect is enough.

This is why rumour and myth gather around places like Epstein’s island. Observers sense something has fallen outside the shared moral order. They reach for older language because modern categories fail. Crime feels procedural. Corruption feels insufficient. Neither captures how reality itself bends once it leaves common oversight.

The so-called temple structure on the island belongs here, not as evidence of belief, but as the crystallisation of atmosphere. Architecture does not need ritual to work ritually. Enclosure, elevation, symmetry, separation. These forms condition behaviour before a word is spoken. They announce exception. They signal that judgement does not flow outward.

Historically, the inner chamber was always the most protected space. Not because it housed gods, but because it housed exemption. Modern power reproduces this instinctively. It builds inward, not upward. It conceals rather than declares. It prefers depth to spectacle.

Once power is sufficiently insulated from consequence, it no longer needs mythology. Endurance alone confers sacral weight.

Kubrick understood this. Power does not simply corrupt behaviour. It reorganises reality. And real power hides, because visibility is the first constraint it ever accepts.

This was never really about sex. Sex was a medium, a way of testing boundaries and enforcing silence. It was never simply about money. Money was the solvent that dissolved limits and made consequences negotiable. It was never only about blackmail. Blackmail was leverage.

The power was the point.

The ability to act without consequence. To survive exposure. To exist beyond the shared moral field. Epstein was not an aberration so much as a demonstration of what power becomes when it is allowed to seal itself off from accountability, and of how easily the modern world learns to tolerate that seal, so long as it remains out of sight.

And now, much of this no longer sits out of sight. Files surface. Images circulate. Names recur. Connections repeat themselves often enough to stop looking accidental. What depended on distance is forced into proximity. It becomes clear how many were tied into the same web, through money, silence, favour, deference, or the decision to look away.

This is what exposure does. It doesn’t just reveal facts. It changes the field. The spell only works while it remains unexamined. Once the structure is dragged into the open, its power drains quickly. What felt vast and inevitable begins to look narrow and fragile. What once appeared sacral starts to resemble stagecraft.

This is the fate of all occult power when it is properly seen. The mystery collapses. The initiation loses its force.

Magic depends on distance, silence, and awe. Take those away and it has nothing left to work with. What remains is not revelation, but banality.

Systems of protection that only ever functioned because they were allowed to.

Power hates this moment. Because once it is exposed, it no longer feels inevitable. And once inevitability is gone, the structure that sustained it begins, quietly, to fail.

What comes next is never pretty. The emperor has no clothes, and once that’s obvious, the instinct is to blame, deflect, and fragment. But what’s really exposed is not individual guilt so much as structural sameness. The elites are not exceptions to the system. They are its repeatable parts. And once that pattern is visible, the protection it relied on weakens. Exposure rarely ends cleanly, and it rarely ends where it begins.

There is an old phrase, often attributed to the Illuminati, that is usually misunderstood. It was never a celebration of freedom. It was a description of what power looks like once it slips free of constraint.

Nothing is true. Everything is permitted.

This week we were joined by to talk about Islamic immigration dynamics, the realities of 'Islamism' often not covered and the reactionary forces behind Islam.

Welcome to All Hands on Deck—a special podcast for Tortuga Society members and Tortuga Media paychads.

These are recordings of Tortuga’s biweekly standup calls, in which our guys convene to update the group on progress with job stacking and assorted ventures, theorycraft business ideas, and shoot the shit on issues of the day.

Most episodes will be available to paid subscribers — our spicer discussions will be exclusive to full Tortuga Society Members.

Topics Include:

• Assimilation Differences in European Regions

• Discussion on Waves of Islamic Immigration

• European Models of Integration

• Integration Strategy in the UK vs. France

• Historical French Migration and Implicit Racial Bias

• The Misallocation of Human Capital

• Political Understanding of Immigration Waves

• Loss of Paternalism and Integration Failure

• Cultural Superiority and Technical Ideas

• Critique of Blank Slate Theory and Importance of Institutions

• Immigration Selection and Cultural Compatibility

• Strategies for Managing Less Compatible Groups

• Cultural Dominance and Parallel Societies

• Discussion on Cuban Migration and Criminality

• Assimilation and Naming Conventions

• Naming Conventions in the US and Asia

• Future of Islam in European Politics

• Muslim Political Strategy and Coordination

• Traditional vs. Fundamentalist Islam

• Crisis of Confidence in the Islamic World

• Modern Fundamentalist Islam and Traditional Practices

• Fundamentalist vs. Traditional Culture in Migration

• Critique of Muslim Migration Analysis and Proposed Work Camps

• Feasibility and Implications of Work Camp Proposal

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This week we were joined by and explored the limits of digital organization when it comes to tribe.

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