Great ideas don’t scale by accident. They scale because they’re engineered to.

Part I showed you why most books fail before they’re written.

This mini-book shows you how to design one that doesn’t.

If Part I is the diagnosis, Part II is the blueprint.

This is where Category Design meets execution. Most books die because the author never decided what kind of problem they’re solving—or who the book is actually for.

This audiobook gives you the missing framework.

And once you see this lens, you can’t unsee it.

Here are a few key points:

[00:00] - Choosing scalable categories for business books like personal development, personal finance, insights/thinking, leadership, case studies, or relationships. Deciding on an idea-centric or author-centric approach.

[08:17] - Presenting non-obvious solutions to obvious problems can increase shelf life by being surprisingly different, but these solutions may quickly become conventional wisdom.

[17:56] - Titles and subtitles that educate on non-obvious problems people don't realize they have can result in longer-lasting category dominance if the solutions provided are actionable.

[26:16] - Crafting titles that are clear rather than clever, signal the main benefit, and put the right descriptive words in potential readers' mouths to spark word-of-mouth marketing.

[36:14] - Inventing new words or modifying existing ones in titles can name and claim new categories if the book then defines the new term's meaning and differentiates the perspective.

This mini-book is the instruction manual most authors never get.

Because ideas don’t win by being smart.

They win by being understood, repeated, and carried forward.

Arrrrrrr,

Category Pirates

Eddie Yoon

Christopher Lochhead

Arrrrr! 🏴‍☠️ Welcome to a 🔒 founders-only edition 🔒 of Category Pirates. Each week, we share radically different ideas to help you design new and different categories. Founding subscribers can access the entire archive of 200+ mini-books and audiobooks. If you’re not a paid subscriber, hop aboard!

If your career plan makes sense on paper, it’s probably holding you back.

Legendary careers are built through side quests, curiosity, and the courage to follow signal.

That’s how you end up somewhere interesting.

In this episode, we turn the mic toward Bri Clark—the person who recently stepped into the role of Head of Operations for Category Pirates—to share how she thinks, how she works, and why she keeps making herself impossible to ignore.

You may know Bri as the one who:

Turned Shopify into a direct publishing engine for Category Pirates

Kicked off and is supporting this year’s Academy cohort

Helped launch our Founding Subscriber tier

But this conversation isn’t about her work at Category Pirates or all the lifetimes Bri has lived—from paragliding and diving to working remotely across six continents.

It’s about what happens when someone learns to see systems early—and refuses to stay in roles that underuse that ability.

Bri’s career only makes sense once you stop believing in resumes and start understanding how side quests compound.

From wilderness therapy for teenage boys sent to the Utah desert when nothing else worked.

To building and running nonprofit fundraising programs that moved communities and doubled outcomes.

And designing and operating businesses for creators whose work reaches millions.

Across wildly different environments, the same pattern shows up. Bri walks into complexity, spots what’s actually broken, and fixes the system instead of polishing the surface. Not by forcing outcomes. But by designing the conditions where outcomes become inevitable.

That pattern showed up early.

People told Bri she was “good at design.” What they were really responding to was judgment. She could connect identity, ideas, and expression into something coherent—and shape experiences that moved people to act.

That became undeniable inside a nonprofit where she quietly took on far more than her role.

She applied for a promotion for work she was already doing—and didn’t get it.

Instead, she was asked to train the person hired above her and keep running the work.

That was the moment the premise broke. There’s no upside to staying where your leverage is obvious—but unrecognized. The system caught up shortly after, and she was fired.

What Bri could contribute had outpaced what the role was designed to hold.

It exposed a gap between what Bri could see and what the system was built to reward.

And once you see the gap that clearly, you don’t keep pretending it isn’t there.

So Bri stopped trying to fix it from the inside and went all-in on her own business.

Where she rejected the next default moves:

She didn’t cold email.

She didn’t polish a résumé.

She didn’t wait to be discovered.

She told the truth in public.

She published a candid teardown of one of the most well-known photographers’ websites—what wasn’t working, why it mattered, and how it could be better. He reposted it to over a million followers. Leads followed immediately.

Not because she asked, but because she made her value visible.

(Categories don’t get designed by people who stay quiet! 🏴‍☠️)

That moment wasn’t reckless. It was precise. And it revealed a repeatable pattern.

Be a Superconsumer

Say the thing everyone else avoids

Do it with care—and conviction

The response from telling the truth in public made it clear: the fastest way to stand out is to say what everyone else is avoiding.

People weren’t looking for another designer to push pixels or apply a prettier template.

They wanted someone who would sit with the mess, tell them what wasn’t working, and help translate who they actually were into something the world could understand. They didn’t want decoration. They wanted interpretation.

They wanted someone willing to say, “This part doesn’t work. This part does. And here’s why.”

That’s when Bri’s business took shape.

Today, that work lives inside By Breezy—a category-driven web and brand design studio for creators who don’t need another template, but someone willing to think with them and tell the truth.

Bri doesn’t get hired to make things look good.

She gets hired when founders don’t know what they want—or why what they have isn’t working.

That’s why her clients tend to be creators, thinkers, and operators whose work reaches millions and why the work compounds long after the site ships.

That ability—to diagnose, orchestrate, and accelerate outcomes—has been the throughline of Bri’s career long before she ever heard the words Category Design or Lightning Strike.

This episode isn’t about ranting for attention.

It’s about rejecting the default.

When Bri roasts a website—or a broken assumption—she isn’t attacking people. She’s attacking the status quo. She’s naming the invisible problem that keeps smart work from compounding.

Because the real risk isn’t telling the truth—it’s pretending not to see it.

That’s why she’s now helping steer the Pirate Ship.

And why this conversation matters if you’re building a career, a company, or a category that doesn’t fit neatly on paper—but works in the real world.

Here’s how to navigate this conversation:

00:00 – From Native Analogs to AI Wheelchairs: How Category Pirates evolved its operating rhythm to move faster without losing judgment.

02:29 – Paragliding, Risk, and Signal: How Bri’s appetite for risk and side quests shaped how she approaches work, decisions, and momentum.

06:29 – The Push Off the Cliff: Getting fired, getting denied unemployment, and why relief—not panic—was the dominant emotion.

08:01 – Training Your Replacement: The promotion she didn’t get, the six months spent onboarding the hire above her, and the moment the premise broke.

10:22 – Wilderness Therapy in the Utah Desert: What working with teenage boys for 8–12 weeks taught Bri about leadership, discipline, and human systems.

12:46 – The $1M Fundraising Outcome: How “being good at design” was really about orchestrating emotion, flow, and outcomes—not aesthetics.

18:04 – Why Young People Feel Stuck: Bri’s POV on courage, curiosity, social capital, and why degrees without signal leave people frozen.

22:01 – Backed Into a Corner: Running out of runway, hitting the end of savings, and why desperation often precedes clarity.

23:17 – The Website Teardown: Roasting a legendary photographer’s website, why he loved it, and how radical honesty became a Lightning Strike.

26:54 – Making Yourself Undeniable: Why resumes don’t work, why sales calls felt wrong, and how public truth-telling created inbound demand.

29:25 – When Success Creates Burnout: Dozens of leads, record income, and the realization that the wrong clients can kill momentum.

33:26 – The Advisor Trap: Spending $25K on “integrative coaching,” learning the cost of generic advice, and reclaiming personal agency.

37:02 – Rejecting the Sales Call Premise: Why Bri refused manipulative selling, and how “no-sell selling” fit her superpower.

41:05 – Radical Self-Responsibility: Owning the wins, the debt, the mistakes, and why that mindset compounds faster than blame.

48:54 – Ranting as Evangelism: Why roasting isn’t cruelty, it’s missionary work—and how naming invisible problems unlocks outcomes.

52:57 – Web Design as a Trojan Horse: Why the real work isn’t pixels or templates, but helping founders figure out who they are and what they want.

1:00:17 – Raising the Bar While You’re Young: Why reduced expectations are the real enemy—and why 27 is the perfect age to do legendary work.

1:03:26 – From Side Quests to Category Leverage: How following what you can rant about leads to POV, demand, and a career that compounds.

This episode isn’t about web design.

Or operations.

Or even entrepreneurship.

It’s about learning to trust what you see.

About paying attention to the things that bother you, the systems that don’t make sense, and the moments where your contribution outgrows the role you’re in. Bri’s story shows what happens when you stop dismissing those signals—and start building around them.

Not louder.

Not faster.

Just more honestly.

To connect with Bri:

Follow her on LinkedIn

Check out her studio, By Breezy

Arrrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

It takes a ton of courage to tell one of the largest publishing houses on earth:

“No thanks.”

But Paul Millerd did exactly that on a call with Penguin.

He built a different path for himself when writing and publishing The Pathless Path. One with sovereignty instead of gatekeepers. Ownership instead of permission. And pricing designed for value, not for volume.

This Creator Capitalist podcast is about a high-agency career reinvention.

Paul rejected the premise that authors must trade their lifetime rights for a one-time check. The premise that you must shrink your ambition to fit an industry built on scarcity. The premise that “books don’t make money.”

But at the start of his career, Paul followed the default prestige treadmill path.

He went to grad school at MIT, then worked at McKinsey and BCG. But at 32, he was burned out. He had a moment of uncomfortable clarity when none of it felt like his path. That clarity pushed him to write, then to Substack, and eventually to a level of creative agency the default path could never offer.

He stopped letting prestige define his life.

As he told Pirate Eddie, his first real identity shift wasn’t quitting consulting.

It was admitting (publicly) that he had something to say.

He started publishing on Quora and LinkedIn. He shared essays about uncertainty, agency, fear, joy, and the hidden emotional cost of achievement. Every post was another step away from his old identity toward his new one.

Paul wrote because something inside him refused to shut up.

When he finally published The Pathless Path, it became a compass for thousands of people who wanted a life beyond résumés, credentials, and corporate suffering.

Then came the plot twist.

Penguin reached out with a six-figure offer for The Pathless Path, plus a second book.

* $70,000 for The Pathless Path

* $130,000 for a second book

Ninety-nine out of a hundred authors would say yes to this deal.

Paul said no because the deal required:

* Giving up lifetime rights

* Removing the book from print to redesign it

* A royalty structure designed for the publisher, not for Paul

He realized traditional publishing wasn’t offering him a future. It was asking him to sacrifice the one he was already building. And the moment he pushed back and countered with a fair valuation, the room went cold.

The old model couldn’t compute an author with courage.

So, Paul walked.

The $100 Book: Rejecting The Premise, Again

Rejecting the Penguin deal was the spark that led to Paul’s $100 book Lightning Strike.

Paul released a $100 premium hardcover edition—an art object and collector’s piece of the Pathless Path. He sold 250 copies in the first two weeks and has now shipped books to over 22 countries. Just like Taylor Swift reclaimed ownership of her masters, Paul reclaimed ownership of his words. And readers rewarded the courage.

As Eddie told him during the jam:

“FU money isn’t the freedom to walk away. FU skills are the freedom to create outcomes no one else controls.”

Paul has FU skills.

His $100 book is just one proof point of a major category shift.

The future of books belongs to authors who understand pricing, packaging, and category design.

Paul is doing what innovators always do:

* Shrinking the distance between creator and reader

* Designing a book as an experience, not a commodity

* Monetizing with gross margins publishers can’t offer

* Experimenting with bundles, merch, and extension products

* Treating books the way musicians treat albums: constant creation and connection

A $100 book is just the initial momentum to begin building a different book category. This is the same wave pushing us Pirates to sell $100 books with bundled digital assets. It’s the same wave we’re seeing other independent authors ride to control their work and careers.

It’s one of the first steps to becoming a Creator Capitalist.

Here’s how to navigate this conversation:

* 01:23 – Paul’s Pathless Pivot: From McKinsey and BCG to discovering the creative instinct that refused to be quiet.

* 05:00 – Writing Before You’re “A Writer”: How publishing anonymously on Tumblr and Quora became the early writing reps that built his skills and courage.

* 09:35 – The Vulnerability of Publishing on LinkedIn: Why the scariest part wasn’t the writing—it was admitting he cared.

* 20:00 – Rejecting Penguin: The six-figure offer and the six-figure reasons it didn’t make sense.

* 22:56 – Designing the $100 Book: Why Paul treated the edition as an art project, why it worked, and the details of how he created the book.

* 37:07 – Creator Economics vs. Publisher Economics: Understanding margins, shipping, fulfillment, and why independence creates freedom.

* 43:50 – The Power of Superconsumers: Why gifting behavior (buying 5, 10, even 20 copies) is the unlock for author growth.

* 51:57 – Substack, Identity, and the Next Chapter: What Paul is building next and why creator-led publishing is just getting started.

If You’re An Author, Pay Attention

Paul’s story marks a before/after moment for the book category.

* Before: You needed publishers for credibility, distribution, and economics.

* After: You need publishers for… what, exactly?

As an author, you can keep your rights, financial upside, autonomy, and the connection with readers that publishers desperately wish they had. You can own your work. And you can experiment with formats, bundles, pricing, community, and autonomy.

This is the new publishing strategy.

It will be led by authors with courage, clarity, and a category of their own.

Arrrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

Katrina Kirsch

P.S. — Ready to design your category-of-one career?

We recommend starting with the following mini-books:

Ian Roberts spent his life becoming a creative.

He built his career the Native Analog way, spending 25 years teaching painting workshops in Provence, France. He mastered the craft of composition and learned what makes a person come alive when they create. He’s also sold 60,000 copies of his book, Mastering Composition, a subject almost no one else had the courage to claim.

Then, at an age when most people start winding down their careers, Ian pivoted.

* He moved his in-person painting workshops online.

* He built a thriving Mighty Networks community.

* He grew a 200,000-subscriber YouTube channel.

Ian never set out to become an online educator or a creator.

He was trying to protect the one thing he couldn’t give up—painting.

In this conversation with Ian, we explore the questions every creator eventually faces:

* What happens when the thing you create becomes the business that consumes it?

* How do you keep your soul intact when your creativity becomes your income?

* What do you do when your next chapter demands a different version of you?

Ian doesn’t sugarcoat his story. He tells the truth that only someone with decades in the trenches can tell.

You’ll hear how:

* Composition became his category. While the art world obsessed over brushes, color, and technique, Ian claimed the foundational problem no one else would touch: If you don’t understand composition, nothing else works. This insight turned his teaching into a category of one.

* Teaching unlocked his superpowers. Decades of workshops sharpened his ability to simplify the complex, turn philosophy into practice, and speak with a calm authority. He explains the importance of teaching in his career and work.

* YouTube became his ideal channel. Ian didn’t grow by chasing algorithms. He grew because he gave away everything he knew freely, generously, and without holding back. That generosity built a movement of Superconsumers.

* Success created a new dilemma. He built a thriving business that pulled him away from the very thing that made him successful. Ian shares how he’s now unwinding the machine he built so he can return to the studio and find out what the next version of him wants to say.

* In his 70s, he’s redesigning. Ian doesn’t believe in retirement. He believes in Dharma—the calling that owns you, the thing you can’t not do. Painting owns him. And he’s making space for the work only he can create.

This episode is about art. But it’s also about identity, longevity, and the courage to pivot your life when the world thinks otherwise. It’s about how to own your category of one by following your instinct.

And it’s a masterclass in how to build a career around what won’t let you go.

Here’s how to navigate this conversation:

* 00:45 – How a painter accidentally built a digital empire: Why Ian’s workshops in Provence, France, became the start of his online teaching business.

* 04:29 – The composition category: How Ian discovered the foundational problem no one else in the art world was solving and turned it into his niche.

* 10:48 – The YouTube flywheel: Why giving away everything he knew created more demand, more trust, and more freedom.

* 18:15 – Creativity vs. content: Ian shares the tension every creator faces: When does “content” stop being creative and start being a cage?

* 25:10 – The decades that prepared him: Why nothing in life is wasted. Every workshop, every student, and every brush stroke became Intellectual Capital.

* 38:24 – The pivot at 73 years old: Ian’s honest reckoning with time, purpose, and the need to redesign the life he wants next.

* 49:12 – Calling, craft & dharma: Why some work owns you forever, and why that’s a gift, not a burden.

If you’re a creator…

If you’re building a career around what makes you different…

If you’ve ever wondered how to stay true to your craft while scaling your business…

Ian’s story is a call to pay attention to the thing inside you that refuses to quiet down. It shows what happens when you follow the thread of your own curiosity long enough that it becomes the fabric of your life. Most importantly, it’s a wake-up call.

Your work will evolve.

Your interests will shift.

But your calling will keep knocking until you answer it.

Arrrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

Katrina Kirsch

P.S. — Ready to jam on your category idea?

If you’re validating your ideas and want help Languaging your category, upgrade to the Founding Subscription. You’ll get access to Pirate Eddie Bot to pressure-test your POV, as well as the entire Category Pirates library of podcasts, audiobooks, and mini-books.

👉 Upgrade here to start jamming with the Pirate Eddie Bot.

When a business spirals, it rarely happens because demand disappears.

Often, it’s because the economics were rotten long before anyone noticed. Revenue masked it. ROAS disguised it. “Growth” rationalized it.

And everyone inside the company is too siloed, rushed, or optimistic to ask the question that matters:

Is this business creating or destroying value?

The answer is directly connected to the contribution margin. But for most DTC companies, nobody owns that metric.

* Not the CFO, who assumes marketing is handling it.

* Not marketing, who assumes finance is modeling it.

* Not the agencies, who only report ROAS and call it a day.

* Not operations, who assume the margin issues are someone else’s fault.

That unclaimed (and valuable) niche is where Thomas Parrott built his category.

But a year ago, he was planning a different direction.

When Thomas first entered the Category Design Academy, he thought his category was helping U.S. brands expand into Europe. He had decades of experience running DTC operations in the U.K., Europe, Australia, and the U.S. He knew international markets, had operational excellence, and could run launch playbooks.

But there was a deeper pattern Thomas hadn’t named yet—something more specific than expansion, logistics, or operations.

Something he’d practiced his entire career, without realizing it was his leverage.

His breakthrough came halfway through the Academy, during a jam session where everything snapped into place. Thomas described the recurring problem he kept finding inside companies:

Financial misalignment at scale.

Eddie pushed him to say more. Christopher poked at the root cause. And then Thomas said it out loud:

“They want to grow, and I help them grow profitably.”

Thomas’s category wasn’t “U.S. to U.K. expansions.” It was “contribution margin architecture.” His superpower is diagnosing the financial truth that many businesses ignore and fixing it, so growth creates value instead of destroying it.

Once he named it, his sales cycle transformed from 30+ weeks into 30 minutes.

He simply said what he did, with clarity and confidence:

“I fix contribution margin so companies can grow without blowing themselves up.”

Companies leaned forward when Thomas shared his POV, because contribution margin is the number nobody owns but everyone feels.

* It’s the t-shirt that gets returned seven times and loses money by the third.

* It’s the operational lag that eats the margin before the product ever ships.

* It’s the loyalty program that gives away entire orders without anyone noticing.

Thomas has helped companies solve this problem for decades, across QVC, live shopping, Big Book Mail Order, global infomercial launches, and DTC operations on multiple continents.

That history became his unfair advantage, and the patterns became his category.

Contribution margin became the problem only he could frame, name, and claim.

Today, Thomas works with large organizations where misalignment gets expensive fast. He’s hired to diagnose the problem, design the financial architecture, and oversee the team required to fix it (this often includes the super-ding-song consulting firms).

If you want to understand DTC economics or see why so many companies “scale” their way into oblivion, this conversation will change how you think.

You’ll walk away from this episode knowing:

* Why ROAS (Return on Advertising Spend) misleads companies more than it helps them

* How contribution margin reveals the truth about your business

* Why operational excellence is a profit engine disguised as “back office”

* How naming a niche problem can collapse your sales cycle from months to minutes

* Why companies now hire Thomas to run the consulting firms they used to defer to

* How a clear POV can transform your career, your identity, and your outcomes

This conversation is about reframing value through a category design lens. Most importantly, it will inspire you to step into the category you were always meant to lead.

Here’s how to navigate the conversation:

* 00:00-7:53 – From DTC Operator to Margin Growth Architect. Thomas shares how he reframed his expertise into a category that companies instantly understood. He also explains why financial misalignment hits hardest inside public companies with small, messy DTC divisions.

* 09:24 – The Moment the Category Appeared. Why niching down made the problem Thomas solves bigger, more urgent, and more valuable.

* 11:00 – Contribution Margin: The Unclaimed Number. How Eddie and Christopher pressure-tested Thomas’s POV until the category snapped into place.

* 13:36 – The Infomercial Advantage. How decades of seeing real economics up close created Thomas’s instinct for margin architecture.

* 19:23 – ROAS Is the Great Illusion. Why ROAS is a vanity metric that conceals more than it reveals, and how it quietly steers companies off a cliff. Thomas breaks down how he exposes the profit leaks nobody inside the company is tracking.

* 25:46 – The T-Shirt That Changed Everything. The early lesson from Big Book Mail Order that taught Thomas how to analyze contribution margin from the ground up. And the beauty brand that didn’t realize entire batches of orders were being shipped at a loss.

* 45:29 – The Epiphany That Rewrote His Career. How a single conversation, spoken with category clarity, collapsed his sales cycle overnight.

* 56:11 – The View From the Top of the Value Stack. Why Thomas now oversees the global consulting firms that companies once relied on, and what that says about category power.

* 01:07:33 – ROI of the Academy. How Thomas earned back the entire cost of the Academy in half a month. And why category clarity attracts opportunity and eliminates the need for “pipeline stress.”

Thomas didn’t set out to be the Category King of contribution margin. He became it the moment he realized the number nobody owns is the one that matters most. He simply stepped into his superpower to solve that problem for others.

You can connect with Thomas here.

Arrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

Katrina Kirsch

P.S. - If you’ve ever struggled to explain what makes you different…

Or wondered why your expertise doesn’t command the price, respect, or clarity it should, Thomas’s story is a reminder of what happens when you frame, name, and claim the problem. He became valuable by telling the truth about what drives profitable growth.

That’s the power of category design and a compelling POV.

If you’re ready to make the same leap, you can join the waitlist for the next Category Design Academy cohort (starting May 2026) here.

Walk into any boardroom today, and you’ll feel the quiet unease of leaders trying to make sense of artificial intelligence.

Most companies are racing to adopt AI.

But few are asking an important question: Who’s governing it?

If CEOs will soon manage more AI agents than employees, governance becomes the single most important capability a company can build.

Sue Barsamian helps businesses build toward that future.

Sue is one of Silicon Valley’s most respected board members.

She serves on the boards of Box, Five9, Gen Digital (formerly Symantec), and more. Earlier in her career, she worked with Pirate Christopher to pioneer the Lightning Strike strategy that reshaped how technology companies go to market. Today, she’s known as The Velvet Hammer—a leader who delivers extraordinary results while maintaining her humanity.

Sue has spent her career helping leaders turn complexity into clarity.

And an urgent challenge she’s seeing is how we choose to govern AI.

Too many boards treat AI like a quarterly agenda item.

It’s something to monitor, not master.

But when anyone in a company can create a ChatGPT account and spin up an agent that makes decisions, connects systems, and acts autonomously, the old governance model collapses. Oversight alone won’t protect a business.

What’s needed is a new category of literacy where every leader understands not only what AI can do, but how to direct it responsibly.

Governance can no longer be about saying “no.”

It must become the discipline of enabling “how.”

Sue believes the next generation of Category Kings won’t be those who adopt AI first. They’ll be the ones who govern it best.

At Box, for example, every employee is certified on AI. People are building agentic workflows, competing in hackathons, and automating everyday tasks across departments. HR won one of the internal competitions.

That didn’t happen by accident.

The company treats AI fluency the way it once treated financial fluency.

It’s a baseline skill for every role.

Beneath that initiative is a governance process modeled after software development. Every agent or workflow goes through its own lifecycle (proposed, reviewed, validated, and monitored) before it touches production data.

Committees are also evolving at the board level.

Sue says technology and cyber oversight are now discussed alongside audit and compensation. It reflects how strategic AI has become. It’s not a compliance exercise. It’s a system for continuous learning that lets the company innovate without losing control.

Innovation that scales because it’s governed, not in spite of it.

You can’t lead what you don’t understand, and AI is forcing every leader to adapt.

In a future where AI will handle more of the logic, leadership will be an art that requires more judgment, empathy, and connection.

It will be less about commanding tasks and more about compounding relationships.

Sue is an expert at striking a balance between the two.

Her teams call her The Velvet Hammer because she demands excellence, but she delivers it with empathy. The people she has mentored over decades still follow her because she knows that performance and trust are partners. Results without relationships don’t last.

In this conversation, you’ll discover:

How AI is redefining governance as a source of capability, and why it will decide which companies win in the agentic era

The inside story of how Sue’s boards are redesigning oversight for a world where bots outnumber employees, and how it changes what “risk” even means

How boards can evolve to see technology and cyber risk alongside financial risk

Why Lightning Strikes remain the organizing principle of category leaders, and how Sue helped co-create the legendary Lightning Strike strategy

What Sue has learned about leading with trust, rhythm, and responsibility

The companies that thrive in the agentic era won’t be defined by how much AI they deploy, but by how much human judgment they preserve. Boards will need to understand algorithms the way they once understood accounting. And every professional, regardless of title, will have to think like a technologist and act like a teacher.

This conversation is a call to every leader: AI alone won’t make your company legendary.

You must direct it with clarity, courage, and compassion.

(And enable your team to do the same.)

Arrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

Katrina Kirsch

P.S. – Want to unlock the entire jam session with Sue?

Sign up for a Founding Membership. You’ll instantly get access to this conversation, along with 35+ Founder’s posts, the Pirate Eddie Bot (your AI category designer), and the entire Category Pirates archive. It’s the perfect way to plan your category strategy for 2026!

Most companies see AI as a shortcut to efficiency.

Fewer meetings. Fewer people. Fewer problems.

But that’s an Obvious way to use AI.

As the Head Coach of Outside In Leading and former HydraFacial Chief Talent Officer Deb Rodriguez explores the Non-Obvious application of AI:

“If you’re only using AI to remove work, you’re missing the point. The future is about multiplying the people who create the work that matters.”

Deb has spent decades building teams and turning companies into profit centers, like scaling HydraFacial from $40M to a public company worth billions.

Her secret isn’t headcount.

It’s human judgment.

In this conversation with Deb, we explore what it looks like to codify that judgment in a world of AI agents—and how leaders can translate wisdom into systems that reason, coach, and make calls on their behalf.

The result: Wisdom that scales you.

Deb reveals a bigger truth we’ve been writing about for months.

AI isn’t supposed to erase the work—it’s supposed to amplify the people doing it.

But as Deb points out:

We’re deleting the meetings where mentorship happens

Automating the feedback loops where judgment is developed

Delegating decision-making to dashboards and calling it “progress”

Most dangerously, we’re strip-mining the one thing we can’t replicate:

People.

Every business outcome starts with people.

But people don’t scale easily, until now.

Deb’s 555 Framework (5 outcomes, 5 metrics, 5 expectations) codified decades of leadership intuition into something teachable.

She shows us what agentifying your intuition will look like: turning your logic, language, and leadership style into an AI system that can coach, reason, and respond like you.

Not replacing humans with bots.

But mirroring the best parts of human experience so that wisdom compounds.

We jam on how every function (sales, finance, marketing, product, HR) will soon have its own fleet of agents:

Agents that think like your top performers.

Agents that coach your teams in real time.

Agents that reason through complexity using your playbook.

What Deb is doing for HR is what every executive will soon do for their department—turn experience into an exponential asset that compounds long after they log off.

That’s leadership, at scale.

Here’s what you’ll discover:

Why most companies waste AI on time-saving instead of value-creating

The mindset shift from managing people to multiplying people

How to think about cloning your own expertise into an agentic system

Why the next generation of executives will be measured not by the size of their teams but by the power of their agents

How to use Deb’s 555 framework to turn HR from a compliance function into a profit center

If you lead people, build teams, or want to scale your own judgment, this conversation will change the way you think about AI—and how it will impact HR—forever.

Here’s How to Navigate This Conversation

00:00 – The Hidden Cost of “Efficiency”: Most companies aren’t short on tools—they’re short on judgment. You’ll learn why deleting “busy work” often deletes the very friction that builds mastery.

07:42 – The Human Flywheel Inside HydraFacial: How a scrappy skincare company scaled from $40M to a billion-dollar IPO by investing in people first—and what Deb calls “making HR a growth engine, not a police department.”

12:08 – The Myth of the Perfect Org Chart: Why most org charts are designed for control, not creation and how leaders can redesign roles around energy, outcomes, and ownership instead of hierarchy.

19:55 – When People Become the Product: The turning point in HydraFacial’s growth story: how elevating employee experience directly multiplied customer experience, creating what Deb calls the “inside-out revenue loop.”

24:33 – How to Build a Judgment Machine: Deb shares the real difference between data-driven and judgment-driven leadership—and why the best leaders teach people how to think, not what to do.

27:05 – The AI Shift: From Automating to Agentifying: Why Deb believes the leaders of tomorrow won’t just use AI to save time. They’ll use it to scale themselves. Hear her forecast on how AI will evolve from assistant to advisor.

35:40 – The People Multiplier Mindset: What separates managers who use tech to remove people from those who use it to multiply them, and why “wisdom at scale” is the new business moat.

39:25 – Culture as an Operating System: Why the companies that will win the Agentic decade aren’t optimizing workflows—they’re programming culture. Deb unpacks how to make values executable and measurable, like code.

42:55 – The Agentic Decade Ahead: We look forward to consider what happens when every company has a “clone bench” of digital agents trained on its best thinkers and what leaders can do today to prepare.

If you’ve been wondering how to get ahead of the AI hype train without getting flattened by it, start here.

Because in the decade ahead, wisdom will be the exponential resource.

When hundreds of companies were fighting for urban telecom towers, Melissa Andrews walked the other way.

Instead of battling in the obvious market, she and her husband Tom went where almost no one was looking.

The farm.

Together, their first act was turning rooftops into telecom platforms when everyone else just saw buildings. That overlooked idea became a thriving business.

But in 2019 they asked a different question:

Why don’t farmers have the same connectivity as city dwellers?

The answer became Connected Farms.

Instead of fighting hundreds of telcos for urban market share, Melissa carved out a category nobody was paying attention to: agricultural connectivity.

Most people fight to be an “ER” company. Better. Faster. Cheaper.

The ambitious ones try to be the “EST.” Fastest. Smartest. Biggest.

But Melissa? She chose to be different.

Which made her the only.

The only LTE provider in ag. The only ones putting Starlink on tractors. The only team building private networks under almond orchards and dairy sheds.

She didn’t wait for a framework.

Long before she ever heard of Category Design or joined the Academy, she relied on two instincts that everyone can practice:

Curiosity: Keep asking “why” until you uncover a problem nobody else is solving.

Empathy: Listen closely enough to hear the pain underneath the surface request.

You don’t need to marry an engineer. You don’t need to stumble into the “perfect” market. You just need to pay radical attention to what frustrates people and be curious enough to keep pulling on the thread.

That’s the part you can do today.

Those instincts led her to the opportunity. But instincts alone can leave you wondering:

Is this real? Can I repeat it? How do I explain it to others?

That’s when Melissa joined the Academy. Not to learn curiosity or empathy—she already had those. But to get the language, the frameworks, and the confidence to take what she’d discovered and scale it.

“The Academy gave me the frameworks and language to explain what we were already doing differently. That clarity is what turned our instincts into strategy—and strategy into growth.” - Melissa

For Melissa, the Academy wasn’t about theory. It was about practice.

She jammed with peers who poked holes, asked better questions, and forced her POV to get sharper.

Out of those sessions came a phrase that changed everything: Digital Darkness.

Two words that made the invisible pain of farmers instantly obvious.

Two words that turned blank stares into “Oh, I get it.”

That’s what happens when you stop circling around an idea and use Languaging.

And the impact was immediate.

Before, every conversation with a farmer was a long, slow education process. After? The timeline collapsed. Instead of months of explaining, she could move people from problem → solution → customer in a fraction of the time.

Her pipeline didn’t just grow—it accelerated.

What Melissa learned didn’t just apply to Australia and New Zealand.

Or farming.

Or even telecom.

The frameworks she picked up inside the Academy transcend markets.

They work across categories, industries, and geographies.

Because once you can name the problem in a way no one else can, you don’t just win locally.

You win globally.

Super Consumers. Super Agents. Super Advantage.

If you want to win in the AI era, don’t build for the average.

Build for your supers. Then train your AI to think like them.

In this mini-book, we reveal the future of category creation: AI Super Consumer Agents.

The idea is simple but powerful.

Your best customers already know what the future looks like.

Now, AI lets you bottle their instincts—and scale them across your entire company.

Instead of generic chatbots and obvious LLMs giving average answers, you can train narrow, purpose-built agents that pressure test decisions, identify new growth levers, and turn customer obsession into category domination.

This is not about “using AI.”

It’s about creating outcome-driven AI agents trained on the weird, wonderful, wallet-out instincts of your most loyal fans.

Here’s what you’ll get inside:

[00:01:00] – Lose Your Super Consumers, Lose Your Category: When Harley-Davidson hired a non-biker CEO, they didn’t just break tradition—they broke trust. The backlash was proof that supers are the brand. Ignore them and you don’t just lose relevance. You lose the whole damn category.

[00:05:00] – Obvious AI Will Kill You Faster Than Harley’s CEO Did: Feeding generic customer data into AI creates “plausible mediocrity at scale.” If your inputs are average, your outputs will be painfully obvious—drop the price, make the logo bigger, copy the trend. Supers don’t want any of that. They want different, and they’re happy to pay for it.

[00:09:00] – Most CEOs Spend More Time on the Toilet Than With Their Supers: Harvard data shows CEOs spend just 3% of their time with customers—only 0.3% with supers. That’s 11 minutes per week. Meanwhile, founders who are super consumers (like those behind Instacart and ThirdLove) build billion-dollar companies.

[00:15:00] – AI Gives You 24/7 Access to Your Best Customers—If You Train It Right: Most companies still layer insights through agencies, surveys, and sanitized data. But AI changes that. You can now scale the unfiltered voice of your supers—every tangent, metaphor, and passionate rant—and use it to pressure test strategy, price changes, product ideas, and more.

[00:20:00] – Your First Agent Should Be a Wizard of Weird: Before building a chatbot or customer service agent, start with the one that matters: a wizard of weird data. This agent isn’t just smart—it’s trained to think like your highest-value customers and see what others miss.

This isn’t just an AI strategy.

It’s Category Design x AI x Super Consumers—a new playbook for founders, CMOs, and execs who want to build the future, not react to it.

And this is just part one.

In the next mini-book, we’ll show you how to go from capturing existing super insights to uncovering brand new ones with AI—then turning those insights into a full team of agents across every function in your company.

Because when AI thinks like your supers,

You don’t just scale your business. You scale your category advantage.

Arrrrrrr,

Category Pirates 🏴‍☠️

Eddie Yoon

Christopher Lochhead

Katrina Kirsch