Meet The 2026 Category Design Academy Graduates [Part 1]
Get to know the legendary pirates who just finished Cohort 3.0.
Arrrrr! đ´ââ ď¸ Welcome to a Wednesday Founder Post 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, The Pirate Eddie Bot, copies of our Big Books, and audiobooks. If youâre not a paid subscriber, hop aboard!
Dear Friend, Subscriber, and Category Pirate,
A new wave of pirates just walked the plank into category design legend.
Cohort 3.0 of the Academy graduated on April 1st, 2026, and to call this group âimpressiveâ would be the kind of lazy, comparison-game language weâd kick out of a workshop. These pirates spent five months getting uncomfortable on purpose. They reframed their businesses. They raised their prices. They walked away from clients who werenât ready. They built brands, books, board strategies, diagnostic tools, and entire new advisory practices. And along the way, they jammed with each other in a way that turned a cohort into a crew.
A quick note before we get to the spotlights:
This post is Part 1 of 2. We have more graduates than we can fit into a single sub-stack post without burying everyone, so weâre splitting it up. Part 2 will follow with profiles of the rest of the crew. If youâre a Cohort 3.0 grad and you donât see yourself here yet, youâre up next.
Weâve also said this before, and it bears repeating: the Academy isnât a course where you watch some videos and get a certificate. Itâs a five-month commitment to thinking about your thinking, getting feedback you didnât ask for, and choosing painfully different over painfully the same. Every pirate below made that choice.
Without further ado, here are some of the Category Design Academy 3.0 graduates:
Meet Mike Harker
Mikeâs Category: Category-First Brand and Product Studios for Agencies That Refuse to Be Commodities
Mike runs ThoughtLab, a digital agency heâs been building for 26 years. He came into Cohort 3.0 with a hunch and left with a hammer.
The hunch: most agencies (and most of their clients) are pretty and dumb. They show beautiful renderings, they talk like everyone else, and if you covered the logos on their proposals, you couldnât tell them apart. The hammer: a complete rebrand of ThoughtLab from âbrand-first digital agencyâ to âcategory-first brand + product studio,â with vertical sub-brands (like Archipod for the architecture, engineering, and construction industry) for niches that warrant their own positioning.
Mikeâs reframe came in two parts. First, he stopped describing himself as a digital agency and started describing himself as a category-first brand plus product studio. Second, he started telling clients the truth that nobody else was telling them, that being forgettable is the real consequence of being a commodity.
Mikeâs Academy Wins
Made the top 2 of 3 finalists on a $1.3 million RFP for Lutheran Hour Ministries, competing against two faith-based agencies as the non-faith-based outsider
Reframed a 26-year-old digital agency into a category-first brand and product studio, with sub-brands for specific niches
Repositioned proposals so that, in his words, âthey literally canât compare usâ
âItâs the first time in my entire history of 26 years Iâve felt that clear that they canât compare us. And Iâm having fun doing it.â
The Painfully Different Method
Mikeâs category superpower is telling clients what their friends and competitors wonât. His point of view, refined over months of jamming with the crew, lands on a simple choice: painfully the same, or painfully different. Pick one.
He frames it through three moves. Niche down hard, because there is a real difference between competing against millions of digital agencies and competing against two. Lead with category, not brand, because branding without a point of view is just a nicer paint job on a commodity. Make yourself uncomparable, because the goal isnât to win the bake-off, itâs to refuse to enter one.
You can learn more about Mike and his work here.
Meet Markham Rollins
Markhamâs Category: Retirement Drift, the Problem Nobody Admits They Have
Markham came into Cohort 3.0 with something most graduates donât have, a YouTube channel with over 1.5 million views and a real audience already calling his category by name in his comments. What he didnât have was the full architecture, the book, the lightning strike, the integrated offer.
He left with a plan to build it.
Markham and his partner Jody run Retirement Transformed, a multi-format business helping people in their 50s, 60s, and 70s solve the problem nobody wants to admit they have. Theyâre bored. Theyâre lonely. Theyâre lost. They have all the money. They did everything they were told to do. And now theyâre staring at 30 more years of life with no script for what to do with them.
That problem has a name. Retirement Drift. Markham Framed, Named, and Claimed it. And his audience is already uses it back to him in the comments of his YouTube videos.
Markhamâs Academy Wins
Validated his pricing reframe from $895 to $1,495 for the eight-week masterclass after running it through the Academyâs pricing pressure-test
Confirmed the architecture for a full integrated offer: the book, the course, the community, the AI bot, all under the Retirement Drift banner
Started planning a 2026 lightning strike for a Retirement Drift book, modeled on the Category Pirates Creator Capitalist launch
âWeâre solving a problem that people donât really know they have, and they definitely donât want to admit they have it. They donât want to say theyâre bored. They donât want to say that theyâre lost. They donât want to say theyâre lonely. But itâs a serious problem.â
The Drift Method
Markhamâs approach is to refuse the comfortable euphemisms that the retirement industry has trained everyone to use. Nobody wants to say âIâm drifting.â Nobody wants to say âI made it and Iâm miserable now.â Markham makes the conversation safe by giving the problem a name thatâs accurate but not shameful.
His three-move sequence: Name the drift, because the unnamed version is the dangerous one. Build the routine, because 28 out of 35 of his masterclass alumni said the morning routine was the single biggest unlock. Expand the seven pillars, because retirement isnât a financial event, itâs seven different transitions happening at once (physical wellness, mental wellness, relationships, vision, passion, purpose, and one more depending on the person).
You can learn more about Markham, Jody, and Retirement Transformed here.
Meet John Wilson
Johnâs Category: Scale Signals for Companies Drowning in Insights
John came into the Academy with one of the cleanest reframes of the entire cohort. He spent decades watching companies pay six and seven figures for âconsumer insightsâ that didnât actually predict anything. The deck would land on the CEOâs desk. Everyone would nod. Nothing would change. The insights were directionally true and directionally useless.
Johnâs POV is that companies arenât suffering from a lack of insights. Theyâre suffering from too many. Every PowerPoint, every dashboard, every customer interview produces a new âinsightâ and the executive team has no way to tell which ones predict scale and which ones predict nothing.
So John reframed the entire category. Stop calling them insights. Start calling them scale signals.
A scale signal is an insight that predicts. An insight that doesnât predict is just an opinion with a confidence interval. By renaming the category, John gives executives a sharper way to triage whatâs on their desk. Most of what theyâre looking at isnât a scale signal. And the few signals that actually are signals deserve disproportionate attention.
Johnâs Academy Wins
Coined and locked in âscale signalsâ as his category language, replacing âconsumer insightsâ and âmarket researchâ with a sharper, more accountable frame
Pressure-tested the language with multiple clients during the cohort and watched it land every single time
Started building IC around how to spot a scale signal versus a directional insight you can safely ignore
âInsights are everywhere. Scale signals are rare. The whole industry is calling everything an insight, and thatâs the problem.â
The Scale Signal Method
Johnâs superpower is filtering noise from signal in companies that are addicted to noise. Most consumer insights teams are funded to produce insights, which means they produce them whether the insights are predictive or not. Johnâs frame forces a different question, can this insight predict scale, or is it just true?
His three-move sequence:
Define the scale event the company is trying to cause.
Inventory every âinsightâ against that scale event.
Remove the insights that donât predict and double the budget on the ones that do.
Most of what gets killed is the stuff the company has been celebrating. Most of what gets doubled is something the team had been ignoring.
You can learn more about John and his work here.
Meet Nick Kringas
Nickâs Category: AI Business Development for Lawyers
Nick has lived through more pivots than most people have had jobs. His parents owned a restaurant that closed when the GM plant shut down. He helped them open another one. He left to start an SEO agency. He moved that agency from offline-to-online clients, then from defense to plaintiff law, and now heâs pivoting again, from SEO to AI.
The pattern is the pattern. Nick is the pivot guy. So when he came into the Academy, the question wasnât whether he had a category. It was which one to claim.
He claimed two.
The first is âare you AI invisible?â, which is his current companyâs category. SEO is dying. AI is replacing search. Law firms still need leads, and the firms that figure out AI-driven business development first will dominate. Nick is teaching them how. The frame is sharp because it sidesteps the entire SEO conversation by declaring SEO over and replacing it with a new acronym lawyers can latch onto.
The second is The Pivot Problem, which is the bigger category heâs been living for 20 years without naming. Founders facing contraction, transitions, dying markets, dead categories. They know they need to pivot. They donât know how. Nick does, because heâs done it five times.
Nickâs Academy Wins
Coined âare you AI invisible?â as the replacement category for SEO in legal marketing, and started using it in client conversations immediately
Identified âThe Pivot Problemâ as the through-line of his entire career, opening up a much bigger advisory category beyond his current legal work
Reframed his agencyâs positioning from âSEO for lawyersâ to âAI is the co-founder of your business,â which moves the conversation from defense to offense
âMost people just kind of sit there for too long and it gets worse and worse. The minute you know itâs time to pivot, itâs already too late.â
The Pivot Method
Nickâs frame is that there are good pivots and there are panic pivots, and the difference is timing. Good pivots happen when you start to question your commitment to the category, which is the earliest signal. Panic pivots happen when you have three months of cash left, which is far too late.
His three-move sequence: Diagnose the category, not the company. Most founders blame their company when the real problem is the category theyâre stuck in. Replace the language before you replace the offer. SEO becomes AIBD. Search becomes prompt. Insights become scale signals. Move while you still have runway. The pivot done from strength looks nothing like the pivot done from desperation.
You can learn more about Nick and his work here.
Meet Eddie Geller
Eddieâs Category: Profit Leak Diagnostics for High-Performing Teams
Eddie Geller runs SKOR, and when he came into the Academy, he was selling what he called a âteam assessment platform.â Eddie called it a lame pitch himself. The Academy made him kill it.
What Eddie discovered through six months of jams was that nobody buys a team assessment. CEOs buy outcomes. So Eddie reframed his entire offer around a much sharper villain: profit leaks in your teams. Not engagement. Not culture. Not soft stuff. Hard money, leaking out of the bottom line because of team dysfunction that nobody can see.
He launched the Profit Leak Calculator at getskor.com, a free 10-question diagnostic that takes a CEO three minutes and shows them, in dollars, what their team dysfunction is costing them every year. The category positioning is built on Eddieâs seven muscles of high-performing teams framework, and the visceral reaction has been undeniable. People take the diagnostic. They get the score. And they reorder how they think about their teams.
Eddieâs Academy Wins
Reframed his value prop from âteam assessmentâ to âprofit leaks in your teams,â with a tagline, visual identity, and conference strategy all built around the new positioning
Launched the Profit Leak Calculator at getskor.com, a free diagnostic that converts CEO interest into qualified pipeline
Built and refined the âseven muscles of high-performing teamsâ framework as the spine of his methodology
Booked two conferences in six weeks to evangelize the new category
âEverythingâs about profit leaks. Our visual is about the leak. Our positioning is about the profit leak. Our tagline is profit leak.â
The Hidden Profit Method
Eddieâs superpower is showing CEOs the money sitting on the floor that they canât see. Most engagement surveys produce a fifty-page deck nobody reads. Eddie produces a number. A real, actual dollar figure. And the dollar figure is always bigger than the CEO expected.
His three-move sequence: Quantify the dysfunction (because CEOs will believe a number before they believe a feeling). Connect behavior to bottom line (so the conversation moves from HRâs office to the CFOâs office). Diagnose by muscle, not by mood (because his seven-muscle framework gives the team a map for what to fix first).
You can take Eddieâs Profit Leak Calculator at getskor.com and learn more about his work here.
Meet Mary Kathryn Johnson
Maryâs Category: Uncompetitionable for Women Reinventing Themselves at 40+
Mary came into the Academy with puzzle pieces scattered across decades. A podcast. A coined word. A career that had already defied the rules. What she didnât have was a frame that pulled them together.
She left with one. Uncompetitionable.
Her category is for women between 40 and 60-plus who are reinventing, reentering, or finally realizing they donât need permission to stop fitting into anyone elseâs framework. Mary calls this group out by name and refuses to soften it. Sheâs the CEO Mischief Maker. Her audience is people who are done shrinking.
Maryâs Academy Wins
Coined and locked in the category language (âuncompetitionable,â âunmissableâ) that sheâd been using sporadically for years and finally made the spine of her work
Drafted a manifesto and started a Substack to flood the zone with content for women reinventing themselves
Started writing a book with the manifesto as its foundation
âI donât really give a what anybody else thinks. Weâre done. Weâre embracing who we are. We donât need permission.â
The Mischief Maker Method
Maryâs approach is to refuse the comparison game on behalf of her audience. Frame, name, and claim. Thatâs the Academyâs three-move drill, and Mary applies it to women whose own resumes were written by someone elseâs playbook. She helps them rewrite those resumes in their own voice.
She also brings a Christopher-and-Eddie split to her own thinking, which is an interesting tell. The creative side is loud, irreverent, refuses to play small. The systematic side is quiet, organized, knows what outcome itâs chasing. Mary built her offer to honor both. Thatâs why it works.
âFrame, name, and claim something effectively. Words matter.â
You can learn more about Mary and her work here.
Meet Jill Consor Beck
Jillâs Category: AI-Era Time and Team Design for Executives
Jill spent Cohort 3.0 doing two things at once. Caring for her mom. And quietly rebuilding the way she charges, pitches, and positions herself.
When you ask Jill about her wins, sheâll tell you they werenât grand. We disagree. The mind shift she described, where she stopped pricing her work by time and started pricing it by outcome, is the single hardest reframe most freelancers and consultants ever make. Most never do it. Jill did.
Her category is now sharpening into something much bigger than time management. Itâs executive coaching at the moment AI is forcing every leader to rethink how their team should actually work together. If youâre an executive telling your team to âuse AI moreâ while also forcing them to live in Slack, Jillâs the one who tells you, in language youâll nod along to, that youâre undermining yourself.
Jillâs Academy Wins
Reframed her pricing model from time-based to outcome-based, and started saying no to clients who wouldnât pay for the value she was creating
Coined the âSavvy Tossâ with Pirate Christopherâs help in a jam, used it on sales calls, and turned it into a Substack post
Pitched her AI-and-teamwork POV to executives at RSA Conference and got real traction
âI learned to charge more. And if they donât want to pay, well, then it.â
The Collective Time Method
Jillâs superpower is naming the trap that knowledge workers and their bosses are walking into. AI is making existing knowledge and existing execution closer to free every day. Most executives are responding by doubling down on the wrong thing, asking their teams to do more of what AI now does, and burning them out in the process.
Jillâs POV: Donât optimize for your time. Optimize for collective time. The executives who only save their own time at the expense of their teams will lose their teams. The ones who design systems that save everyoneâs time, including the teamâs, will be the ones still standing in five years.
You can learn more about Jill and her work here.
Meet Donald Hawthorne
Donâs Category: Naming the Drift Before It Becomes Disaster
Don walked into the Academy with decades of turnaround experience and walked out with something rarer than experience. He had a category.
The villain Don is hunting is Executive OmertĂ , his own term, an internal corporate code of silence that lets executives feel something is wrong at 3am and decide by 9am to not bring it up. It masquerades as professionalism. It costs companies billions. And Don is one of the few advisors who has lived through enough turnarounds to recognize it before it metastasizes.
His POV is sharp: there are people who lie with lies. There are people who lie with the truth. And there are people who lie with silence. The third group is the most expensive. And itâs the one nobody is willing to call out, until Don walks in.
Donâs Academy Wins
Coined and refined âExecutive OmertĂ â and âlying with silenceâ as the category language for the problem he solves
Took category design into his real-world board work, including a parish school board thatâs now reorganizing its strategic direction around the principle of being different, not better
Pressure-tested his point of view with multiple investor and CEO supers, refining the language each time
âIt masks itself as professionalism, being a team player. The reality is, you should just talk about whatâs really going on.â
The See What You Canât Smell Method
Donâs superpower is what he calls being nose blind to your own stinky bets. Most executives canât smell their own farts, to use the same metaphor Don used in our jam. The Strategy Mirror is his diagnostic to expose the bets that stink before they cost a company nine figures.
His three-move sequence: Diagnose the drift early. Most consultants get called in once the company is on bridge financing, which is too late. Bring the team into the room and force the silent conversation. The one nobody wanted to have in front of the CEO. Force a fund-or-kill decision in 90 days, because letting bad bets drift is the most expensive thing a board can do.
You can learn more about Don and his work here.
Meet Ankit âKitâ Chandra
Kitâs Category: Category Design for Early-Stage Operators (and the Salespersonâs POV on Building Markets)
Kitâs path through Cohort 3.0 is the one that proves the Academy works for people who arenât trying to be solo consultants forever. He came in as a sales guy with an advisory side hustle. Heâs leaving as someone about to step into a senior operating role at a venture firm building agentic AI companies.
In between, he made some money.
Kit went from zero to $45,000 in advisory revenue in four to five months, mostly by teaching category design principles to early-stage founders. He got in front of a VC firm. He started using category design framing to differentiate himself in job interviews, where most sales candidates show up sounding the same.
His next chapter is taking everything he learned about Superconsumers, non-obvious problem framing, and category design and applying it across a portfolio of agentic AI companies competing in a space where everyone is calling themselves âAI nativeâ and nobody is saying anything different.
Kitâs Academy Wins
Built a category design advisory practice from scratch, generating $45,000 in 4-5 months
Got in front of a venture firm doing both fund and operate work, and is moving into a senior GTM role
Started using category design as a hiring differentiator, asking hiring managers questions about Superconsumers and category that no other sales candidates ask
âCategory design owns me at this point.â
The Salespersonâs POV Method
Kitâs wedge is that heâs coming at executive operating from a salespersonâs lens, which is rarer than people think. Most CEOs come from sales, but most category design advisors come from marketing or strategy. Kit bridges the gap.
His three lenses for analyzing a market: Whatâs the problem design thatâs commonly accepted? Who are the Superconsumers and what is their most extreme problem? Whereâs the weird data that nobodyâs looking at? When he applies that to a category like agentic AI for revenue cycle management, he refuses to let his clients say âAI agentsâ like everyone else. He pushes them to niche down to a specific use case where they can dominate, then expand from there.
You can learn more about Kit and his work here.
As our third cohort of Category Design Academy graduates moves on to owning their categoriesâŚ
We want to thank these daring Pirates and everyone who embarked on this journey with us.
To everyone in Cohort 3.0, including the pirates whose profiles will land in Part 2: thank you. You showed up week after week, asked the questions you didnât want to ask in front of your peers, and let us push you to places that probably felt scary in the moment.
What we want for each of you, the same thing we wanted for the 2024 graduates, is for you to keep going. Category design isnât a phase. Itâs a practice. The Academy is the on-ramp to the rest of your life, not the destination.
Cohort 4.0 kicks off May 4th. Applications are closed and the cohort is capped. If you wanted in and missed it, keep reading.
To everyone else reading this who has ever wondered what category design can do for you and your work, these graduates are the answer.
Stay tuned for Part 2.
Arrrrrrr,
Category Pirates
P.S. Want to do this work yourself?
Cohort 4.0 is closed and starts Monday. But every grad above will tell you the same thing. The real work doesnât happen in the workshop. It happens between the workshops. At your desk. At midnight. When the doubt creeps in and you have to pressure-test your own POV without anyone there to catch you.
The Pirate Eddie Bot is your in-between.
Trained on every mini-book, every framework, every jam, every piece of category design IC weâve ever published. Ask it about your villain. Ask it to tear apart your tagline. Ask it to help you find the FROTO in your offer. Ask it the questions Don asked, the questions Mike asked, the questions Eddie Geller asked. It will do for you what it did for them.
The Pirate Eddie Bot lives behind the Founding subscriber door. Become a Founding subscriber here and start jamming today.
If youâd rather do the work in a cohort, the waitlist for Academy 5.0 is open. Add your name here and weâll be in touch when applications open.
WOW! My face with the signature pink!
Thank you Christopher, Eddie, Bri, and all my fellow Category Pirates for cheering, holding the bucket when I got sea-sick, and allowing me to stumble alongside you as a crew member on this amazing pirate ship! Here's to the many years ahead charting new category courses together!
LFG!
(with a tankard of rum)