Workless AI 2026 · Limitless AIOS internal review

The Day.

Hotel Regent, Porto Montenegro · Thursday 30 July 2026 · organised by Jannis · sponsors: Hostinger, Glaido, ClickUp, Gamma, Higgsfield

Every session captured, reconstructed from 18 Plaud recordings, the official schedule, and 55 slide photos - Matthew's 45 plus 10 of Michael's captures (attributed by capture time AND visual verification; where the same slide was captured more than once, one photo is kept), correlated against his own conference notes. All spoken numbers are unverified conference claims.

Value-based pricing

Nate Herk

Price at ~10% of projected year-one value, agree ONE KPI baseline before building, never discount - slice scope. The backstage formula for the held install price and the Liberty pilot baseline.

"Rot" sells the retainer

Mark Kashef

An OS starts obsoleting the minute it is built - someone must be the plumber, and "plumbing is the most profitable thing in AI". The cleanest retainer justification yet.

Context is the moat

Chris Cunningham, ClickUp

A ~$4bn company's strategic bet: models are interchangeable, whoever owns the context of work wins. Third-party proof of the AIOS thesis.

Change the asset class

Ethan Monkhouse

Service firms exit at ~2.7-3x profit unless accumulated intelligence becomes a transferable, defensible technology asset. Confirms the skills-as-IP exit thesis.

Deterministic ROI

Bohdan and Adam + Riccardo

Skills validated 20-50 times, retainers as a slice of measured savings, and deterministic workflows so daily tasks cost nothing in inference - the quality and cost bar for Liberty.

9:30

Opening

Jannis (organiser) Not recorded

Jannis opened the day and set the frame. Not recorded.

9:45

Lessons from the front lines of AI adoption

Liam Ottley Confirmed - schedule + slides

Recording started 10:13; the morning ran about 25 minutes late and the 10:45 break absorbed it.

The Morningside AI founder walked five common AI-adoption mistakes drawn from three recent "AI Makeover" clients, and pitched his fix: an "AI workspace" where non-technical staff build their own tools with a coding agent. Attendees were handed a starter workspace zip - the same shape as a Limitless AIOS install.

Key takeaways

Apply to Limitless

Competitive intelligence first: the biggest audience-holder in the space now sells a near-identical install. Sharpen differentiation (retainer relationship, adviser vertical, five-layer depth, the course) and weigh the intensive-week delivery format. His handout zip is in the KB resources folder.

Slides captured (5)

"Inside the fourth business - The ledger": every session logged, agents message each other overnight
"Inside the fourth business - The ledger": every session logged, agents message each other overnight Confirmed
"Dorsey mode: the company becomes an intelligence" - hub-and-spoke, everyone pushes in, everyone queries out
"Dorsey mode: the company becomes an intelligence" - hub-and-spoke, everyone pushes in, everyone queries out Consistent
"Three layers you can buy. One you can't." - Data / Workspace / Surface pyramid, Builders orbit
"Three layers you can buy. One you can't." - Data / Workspace / Surface pyramid, Builders orbit Confirmed
"Where this actually stands" - permissions unsolved, works under ~30-50 people, practitioners scarce
"Where this actually stands" - permissions unsolved, works under ~30-50 people, practitioners scarce Confirmed
"Why this is such a big deal" - the everyone-can-build wave framing
"Why this is such a big deal" - the everyone-can-build wave framing Confirmed Michael's photo
10:15

Mastering agentic workflows

Mark Kashef Confirmed - schedule

The deck itself never names the speaker; the name rests on the schedule slot. The debrief filed this as the "AIOS framework / rot" talk.

A layered AI-operating-system architecture and how it scales from 5 to 1,000 people: identity at the centre, then substrate, rules, hooks (the only deterministic layer), skills and connections. The commercial core was "rot": an OS starts becoming obsolete the minute it is built, which is the argument for the retainer.

Key takeaways

Apply to Limitless

The sharpest retainer justification heard yet: adopt the rot/plumber framing in sales copy and the course, consider a rot-register in the client template, and fold hooks-as-compliance into the Liberty pilot narrative (POPIA).

Slides captured (9)

Slide 02: "Most companies are missing the operating layer"
Slide 02: "Most companies are missing the operating layer" Confirmed
Slide 04: "Each layer changes at a different pace" - stable core to volatile surface
Slide 04: "Each layer changes at a different pace" - stable core to volatile surface Confirmed
Slide 07: "Identity sets direction and limits" - identity.md, hard refusals
Slide 07: "Identity sets direction and limits" - identity.md, hard refusals Confirmed
Slide 08: "One identity file, multiple layers" - Claude, Codex and Gemini read the same identity
Slide 08: "One identity file, multiple layers" - Claude, Codex and Gemini read the same identity Confirmed
Slide 15: "AI roles need a job, limits, and an owner"
Slide 15: "AI roles need a job, limits, and an owner" Confirmed
Slide 19: "Each layer needs its own review trigger" - the ROT.md maintenance schedule
Slide 19: "Each layer needs its own review trigger" - the ROT.md maintenance schedule Confirmed
Slide 23: "A CFO workflow uses all six layers"
Slide 23: "A CFO workflow uses all six layers" Confirmed
Slide 28: "Northline keeps one shared foundation" - company-os/ file tree for a 5-person business
Slide 28: "Northline keeps one shared foundation" - company-os/ file tree for a 5-person business Confirmed
Slide 37: "Relay separates standards from execution" - 50-person structure, hooks, CI checks
Slide 37: "Relay separates standards from execution" - 50-person structure, hooks, CI checks Confirmed
11:00

ClickUp takes the stage

Chris Cunningham (co-founder, ClickUp) Confirmed - schedule

The ClickUp co-founder's growth playbook: audience beats product, scrappy acquisition, and the strategic bet that context is the moat. ClickUp is a ~$4bn company; the talk ranged from the "Jira Sucks" ad to AEO and employee-generated content.

Key takeaways

Apply to Limitless

The context-moat quote is third-party proof of the AIOS thesis from a $4bn company - use it in decks and the course. Rule of three is a cheap filter for /social-post. AEO goes in the marketing-hire backlog. Chris messaged Matthew on LinkedIn the next morning - warm follow-up.

Slides captured (4)

"We didn't buy distribution. We borrowed it." - going upstream to the people users listen to
"We didn't buy distribution. We borrowed it." - going upstream to the people users listen to Consistent
"Context is the Moat" - the strategic bet in three words
"Context is the Moat" - the strategic bet in three words Confirmed Michael's photo
Brain2 features - multi-model routing, persistent memory, MCP connections
Brain2 features - multi-model routing, persistent memory, MCP connections Confirmed Michael's photo
"Nobody follows an agency" - EGC, people follow people
"Nobody follows an agency" - EGC, people follow people Confirmed Michael's photo
11:30

AI workshops to company brain

Riccardo Belli Contarini Confirmed - schedule + slides

His name is printed in the deck footer - the strongest slide confirmation of the day.

An EU founder building "company brains" for mid-market firms: why chat-first assistants break past ~30 users, and the three-part architecture that replaces them - document brain, text-to-SQL business intelligence over an enterprise ontology, and deterministic scheduled workflows that cost nothing in inference.

Key takeaways

Apply to Limitless

Direct architecture input for Liberty: push routine adviser workflows into deterministic code and keep inference for judgement, or Copilot usage-billing eats the royalty maths. The ~30-user ceiling is honest positioning for the SMB install sweet spot.

Slides captured (7)

"The company brain, in three parts" - brain / BI (text-to-SQL) / deterministic workflows. Deck footer: RICCARDO
"The company brain, in three parts" - brain / BI (text-to-SQL) / deterministic workflows. Deck footer: RICCARDO Confirmed
"The Brain" - email, Slack, Microsoft 365, ERP and CRM in one place, always current
"The Brain" - email, Slack, Microsoft 365, ERP and CRM in one place, always current Confirmed
"Business intelligence" - any messy export becomes one SQL table; no hallucinated numbers
"Business intelligence" - any messy export becomes one SQL table; no hallucinated numbers Confirmed
"Every mid-market has a team that does only this" - manual ERP-to-Excel pain
"Every mid-market has a team that does only this" - manual ERP-to-Excel pain Confirmed
"Workflows" - AI writes them once as code: deterministic, cron, zero tokens at runtime
"Workflows" - AI writes them once as code: deterministic, cron, zero tokens at runtime Confirmed
"How do I connect all those single brains?" - workspace per department, C-level queries all
"How do I connect all those single brains?" - workspace per department, C-level queries all Confirmed
"This is how you build a company brain that holds" - millions of documents, sellable to mid-market
"This is how you build a company brain that holds" - millions of documents, sellable to mid-market Confirmed
11:45

Making companies AI-first

Bohdan and Adam Confirmed - schedule + slides

Two operators who productised agency delivery into installable skill bundles ("plugins"): process capture beats engineering, a skill is inputs + rules + tests, and the retainer is a slice of the measured saving.

Key takeaways

Apply to Limitless

Steal the ROI-slicing retainer language for the Blueprint and proposals, and the 20-50-trial validation bar for regulated-client skills (Liberty adviser skills especially). The constraint framework is worth ten minutes with Michael.

Slides captured (5)

Slide 05: "We sell plugins" - a plugin is a bundle of skills; Interview / Extract the SOP / Build the skill
Slide 05: "We sell plugins" - a plugin is a bundle of skills; Interview / Extract the SOP / Build the skill Confirmed
Slide 06: "Eight people. Two weeks. One quote." - trade-business quoting, 60-80 hrs/week on admin
Slide 06: "Eight people. Two weeks. One quote." - trade-business quoting, 60-80 hrs/week on admin Confirmed
Slide 07: "What a skill actually is" - inputs / rules / outputs / evals; "run it twenty times, same answer, or we don't hand it over"
Slide 07: "What a skill actually is" - inputs / rules / outputs / evals; "run it twenty times, same answer, or we don't hand it over" Confirmed
Slide 08: "Why everyone wins" - hours freed, quotes out fast, retainer as a slice of upside
Slide 08: "Why everyone wins" - hours freed, quotes out fast, retainer as a slice of upside Confirmed
Slide 10: "Four weeks ago, we started from zero" - plugins run 80% of delivery
Slide 10: "Four weeks ago, we started from zero" - plugins run 80% of delivery Confirmed
12:00

What Big Companies Buy, and How to Build It

Ethan Monkhouse Confirmed - schedule + slides

Why service businesses exit at roughly 2.7-3x annual profit, and how to break the ceiling: change the asset class, not the multiple. Package accumulated data and intelligence into a proprietary technology asset that is transferable and defensible.

Key takeaways

Apply to Limitless

Near-verbatim confirmation of the skills-as-IP exit thesis. Fold the transferable/defensible framing into the Liberty term-sheet thinking: the pilot's data and machine-learned intelligence must be priced, not given.

Slides captured (5)

"Change the category" - service business (profit x multiple) vs technology asset (recurring revenue x multiple)
"Change the category" - service business (profit x multiple) vs technology asset (recurring revenue x multiple) Confirmed
"The product may already exist" - and the INSTALL THE SKILL box: a skill that reads your AIOS and finds licensable IP
"The product may already exist" - and the INSTALL THE SKILL box: a skill that reads your AIOS and finds licensable IP Confirmed
"Make it easy to buy" - a buyer pays more when they need to assume less
"Make it easy to buy" - a buyer pays more when they need to assume less Confirmed
"Change what they are buying" - service delivery to repeatable system to owned technology to transferable asset
"Change what they are buying" - service delivery to repeatable system to owned technology to transferable asset Confirmed
"Get the skill file + connect" - the exit-opportunities skill QR + his handles
"Get the skill file + connect" - the exit-opportunities skill QR + his handles Confirmed Michael's photo
12:15

AI won't replace you, it will expand you

Akil Wade Confirmed - schedule + slides

Akil is the AfricAI organiser Matthew knows from Cape Town; his slide shows the deck live at africai.co/tivat.

A closing morning session on authentic AI-driven content at scale: a content factory trained on his own scripts, a sponsor-recovery play built on showing brands their finished sponsorship before they pay, and a daily one-document "sweep".

Key takeaways

Apply to Limitless

The sweep is the AIOS morning brief - independent proof the daily brief is the killer everyday use case. The show-the-finished-thing play validates leaning harder on /site-revamp and /demo-video recon demos.

Slides captured (1)

"How to Live in the Age of AI" at africai.co/tivat - section 03 Agent Swarms: "Many workers. One human intention."
"How to Live in the Age of AI" at africai.co/tivat - section 03 Agent Swarms: "Many workers. One human intention." Confirmed
14:00

How Hostinger runs without Hostinger in the room

Hostinger team Confirmed - schedule

A Hostinger PM's walkthrough of their internal AI stack: Dex, a Slack-native company agent with context, memory and per-employee dashboards, and Lumos, plain-English text-to-SQL - plus the two things that failed. No slides captured.

Key takeaways

Apply to Limitless

A 1,000-person company independently converging on the AIOS shape - first-class sales ammo. Their two failures ARE the human-in-the-loop pitch: "not our opinion, Hostinger's scar tissue." The competitor-sweep pattern fits the adviser vertical as an installable skill.

No slides captured for this session.

14:30

Building Glaido in public

Dave, Jannis, Jack and Nate (Glaido) Confirmed - schedule

Plaud misheard the product as "Lighto". The recording spans the next slot too - Jack Roberts' 14:45 talk "The AI automation playbook for agencies" is likely blended into its tail rather than separately captured.

The team behind Glaido, a faster, private, EU-hosted dictation tool (a Wispr Flow competitor and conference sponsor), on product-building lessons: component-level design systems, agentic SDLC, feature-creep discipline, waitlist pre-validation and compliance as a moat.

Key takeaways

Apply to Limitless

Worth a trial against Wispr Flow given "Talk, Don't Type" is an AIOS principle - and a privacy-first EU tool may be an easier compliance story for tier-1 financial clients. The compliance-as-moat language is reusable for Liberty/POPIA.

Slides captured (1)

"What you need before enterprise will buy" - SOC 2, GDPR, ISO 27001
"What you need before enterprise will buy" - SOC 2, GDPR, ISO 27001 Confirmed Michael's photo
15:00

Scaling client acquisition with AI

Serdar and Emil Confirmed - schedule + slides

Two co-founders of a done-for-you Instagram acquisition agency for high-ticket offers: a full-funnel machine with exactly two human touchpoints - recording content and taking the sales call. They shared a skills pack with attendees (check if received).

Key takeaways

Apply to Limitless

Trial-testing and boost-only-proven-organic are directly usable for /ad-studio and the Deej/Meta play. Speed-to-lead physics is evidence for the 5-min response agent once DFE deliverability clears. The "you were here" close is ready-made for the Blueprint funnel.

Slides captured (10)

"The Content Factory, end to end" - recording is the only human step, two hours a month
"The Content Factory, end to end" - recording is the only human step, two hours a month Confirmed
"What the machine does" - research, script, edit, publish as trial reels; Attract-Capture-Qualify-Confirm-Close footer
"What the machine does" - research, script, edit, publish as trial reels; Attract-Capture-Qualify-Confirm-Close footer Confirmed
"Every video gets 3 hooks" - trial reels tested on strangers, only winners reach the real audience
"Every video gets 3 hooks" - trial reels tested on strangers, only winners reach the real audience Confirmed
"The setter that never sleeps" - AI DM setter, speed to lead under 2 minutes, always on
"The setter that never sleeps" - AI DM setter, speed to lead under 2 minutes, always on Confirmed
"A real human-like conversation, not an automation flow" - qualifies, handles objections, books calls
"A real human-like conversation, not an automation flow" - qualifies, handles objections, books calls Confirmed
"Where AI hands over to a human" - the 24h window, every conversation saved, the DM Tracker CRM
"Where AI hands over to a human" - the 24h window, every conversation saved, the DM Tracker CRM Confirmed
"From content to closed" - the full funnel on one slide
"From content to closed" - the full funnel on one slide Confirmed Michael's photo
"It all goes down in the DMs"
"It all goes down in the DMs" Confirmed Michael's photo
"We don't stop at booked" - the 91% show-up confirmation ladder
"We don't stop at booked" - the 91% show-up confirmation ladder Confirmed Michael's photo
"Story sequence generator" - their Stories automation tool UI, Serdar on stage
"Story sequence generator" - their Stories automation tool UI, Serdar on stage Confirmed Michael's photo
15:45

100k subs in 100 days with Claude

Samin Yasar Confirmed - schedule + slides

Samin messaged Matthew on Skool the same day - warm follow-up owed.

How he reached 100k YouTube subscribers in ~100 days (UNVERIFIED) and turned attention into clients without outbound: a three-level system that starts with pure consistency and keeps AI strictly in the organising seat.

Key takeaways

Apply to Limitless

The operating manual for the skill-sharing series: weekly cadence, ten weeks, no quality judgement, Matthew's personal profile as the primary channel. The ramble-then-AI flow is literally the existing Wispr workflow pointed at content.

Slides captured (1)

"Then use a story or analogy" - script structure Hook / Set up / 3 Points / CTA (slide 105 of 176)
"Then use a story or analogy" - script structure Hook / Set up / 3 Points / CTA (slide 105 of 176) Confirmed
16:00

Extra profit from your existing content

Lauren Tickner and Dave Ebbelaar Confirmed - schedule

A live hot-seat: Lauren coaching Dave Ebbelaar (data-science YouTuber, ~EUR 1m/yr, UNVERIFIED) on decoupling bookings from weekly video performance. No slides captured.

The mid-funnel machine: a monthly live "training" (never say webinar) with one evergreen opt-in page and a rotating backend, a thank-you page that books sales calls BEFORE the event, AI-mined sales transcripts for real buying language, and LinkedIn's Services marketplace for passive inbound.

Key takeaways

Apply to Limitless

Upgrade the Blueprint funnel confirmation page from "thanks" to pitch + booking CTA; the monthly-training machine is the launch engine for the £497 course and the Deej community play; mining the Ryan/Globex closed-won transcripts is nearly free. Lauren offered a webinar-builder skill ("just find me").

No slides captured for this session.

16:30

Still relevant next year

Nate Herk Confirmed - schedule + slides

His pricing masterclass handout is in the KB resources folder.

The most commercially relevant talk of the day: how AI consultants should diagnose the real constraint, agree one objective KPI before building, and price on value - roughly 10% of projected annualised year-one value, so the client sees a 10x ROI path.

Key takeaways

Apply to Limitless

Feed the KPI-baseline discipline straight into the Liberty pilot design (baseline every adviser pre-install; that proof prices the national royalty). The two discovery questions and the scope-slice rule go verbatim into the Blueprint call script and sales deck. The 10% maths justifies the held install price.

Slides captured (7)

Bio slide: Goldman analyst, sold his agency at $100k/mo, 880k YouTube (claims UNVERIFIED)
Bio slide: Goldman analyst, sold his agency at $100k/mo, 880k YouTube (claims UNVERIFIED) Confirmed
Discovery question 1: "If you had 10x the business tomorrow, what would break FIRST?"
Discovery question 1: "If you had 10x the business tomorrow, what would break FIRST?" Confirmed
"Choosing ONE number to move."
"Choosing ONE number to move." Confirmed
"Productivity is actually moving the needle, not being busy all day."
"Productivity is actually moving the needle, not being busy all day." Confirmed
"A trackable and objective metric."
"A trackable and objective metric." Confirmed
Discovery question 2: "In a perfect world, what does the solution look like for your business?"
Discovery question 2: "In a perfect world, what does the solution look like for your business?" Confirmed
The value maths: $40/hour x 10 hours = $400; x 52 weeks = $20,800
The value maths: $40/hour x 10 hours = $400; x 52 weeks = $20,800 Confirmed
17:00

Special announcement

- Not recorded

Closing announcement. Not recorded. The day continued with dinner at sea (18:00-21:00, boat from Port Pine, Tivat); the evening conversations are documented separately and privately.

Speaker resources collected

Held in the knowledge base (research/workless-ai-2026/resources/). Third-party files - reference only.

AIOS-Workspace.zip

Liam Ottley

His starter AI-workspace handout: context files, plans, a ledger and a /document command. Competitive intel - a stripped-down version of the Limitless install; read for what he includes and omits.

exit-opportunities-aios.zip

Ethan Monkhouse

A complete Claude skill: valuation framework, readiness checklist, buyer-and-deal paths, opportunity scorecard. A candidate to run against Limitless itself.

How to Price AI Solutions: The Complete Masterclass (docx)

Nate Herk

His value-based pricing masterclass - the companion document to the strongest talk of the day.