Essays and conversations.
Written for operators and investors who want signal.
This is where the longer thinking lives. Essays on growth, pricing, AI, and the commercial side of building software. Board memos on the calls a board has to make. Podcast episodes that take select essays and unpack them for the ear. Published when there is something to say, not on a calendar.
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Investor note · June 2026
When the Code Stops Being the Moat, Diligence Has to Find Where It Went
Bain vibecoding replicas of acquisition targets in diligence is not a toy but a repricing instrument, and once a clone takes a weekend the moat was never the code but the position around it.
Essay · June 2026
The supervision cost of AI adoption
AI adoption does not remove the work but converts doing into reviewing, and the unbudgeted supervision load is a structural drag on the very margin AI is supposed to expand.
Investor note · June 2026
Sell, Do Not Transform. The New Private Equity Answer When the C-Suite Cannot Change Fast Enough
Private equity's reflex for a weak software asset is to fund the transformation and hold, but the binding input is the C-suite's rate of change, the one variable a data room does not show.
Operator note · June 2026
Token Budget Versus Headcount. The New Planning Trade-Off Every CFO Will Run in 2027.
Next year's operating plan carries a token budget beside headcount. Treated as a planning lever, not procurement, it lets leadership trade a person against a block of compute, function by function.
Field note · June 2026
What I Learned Building an AI-Native Company With a Small Team
A field note from building an AI-native company with a small team: agents make production nearly free, judgment does not get cheaper, and the binding constraint moves from production to judgment.
Essay · June 2026
The SaaSpocalypse Mispricing. Why the Rebound Will Be Bifurcated.
The post-SaaSpocalypse rebound is not a return to the old curve. It is the market starting to sort the old curve from the new one, and the recovery will be bifurcated.
Operator note · June 2026
The Delegation Trap. Why You Cannot Appoint Your Way Into Being AI-Native.
Naming a Chief AI Officer feels like leadership, and with AI it is the trap, because the judgment AI forces comes from doing the work and cannot be handed to an appointee.
Investor note · May 2026
AI roadmap theatre: why most B2B software AI strategies will not move the growth curve
Most software boards treat an AI roadmap as an AI strategy, but the first two years of disclosed shipping show the feature inventory has not moved revenue, retention, margin, or category position.
Investor note · May 2026
Software multiples in the agentic era
The SaaS multiple framework assumed durable recurring revenue, low cost to serve, and 80-point gross margins, and agentic AI tests all three at once, splitting the category into three cohorts that should be priced separately.
Field note · May 2026
The difference between using AI and operating AI-natively
A field note drawing the line between using AI through licences and features and operating AI-natively by rebuilding workflow, hiring, pricing, product, and capital around the model.
Operator note · May 2026
Why product, go-to-market and pricing must be rebuilt together
AI transitions fail when product, go-to-market and pricing are run as sequential workstreams rather than one integrated reset, because AI changes value capture first and value capture is a pricing variable.
Investor note · May 2026
The workflow obsolescence risk
The AI risk most software boards still misprice is not feature-level competition but workflow-level disintermediation, where AI removes the workflow a product currently monetises.
Field note · May 2026
What six people can now attempt
A field note from building AI-native, arguing that lower marginal cost of code widens the scope of problems a small team will rationally attempt, not just its speed.
Operator note · May 2026
Your first AI hire may be the wrong one
The reflex when a board asks about AI is to hire someone with AI in their title, but in most B2B software companies the first constraint is the operating model, not model capability or engineering bandwidth.
Podcast · 45 min · May 2026
The $2 Trillion Wipeout: Debating the AI-Native Structural Reset
Two AI hosts debate the second growth curve thesis from the essay. Why the February 2026 repricing was structural, not cyclical, and what the operating reset looks like for CEOs and boards.
Memo · May 2026
Five questions every software board should ask in 2026
Five board-level questions that re-anchor the AI conversation from the product roadmap onto the business model, each answered with operating evidence.
Investor note · May 2026
Five AI questions to ask in software diligence
An investor-grade reframe of the board memo questions, tuned to underwriting choices across workflow disintermediation, switching cost, pricing survival, margin, and go-to-market exposure.
Investor note · May 2026
The AI roadmap is not the moat
A reframe of what counts as defensible in AI-native software, arguing investors should diligence the moat layer of data, integration, and switching cost rather than the roadmap layer.
Investor note · May 2026
Where AI creates margin expansion and where it destroys it
The specific configurations that raise software gross margin under AI economics, set against the ones that destroy it, and how each lands inside the contract envelope.
Essay · May 2026
AI-native is not a product strategy. It is an operating model.
Treating AI as a product strategy puts it inside the roadmap. Treating it as an operating model puts it inside how the company decides, allocates capital, prices, and builds.
Essay · May 2026
The Board Memo Every B2B Software CEO Needs to Write in 2026
The board memo only the CEO can write: five questions about what AI does to this specific software company, from the workflow it monetises to the pricing that carries it.
Essay · May 2026
The SaaS company after SaaS
The next decade is not a feature cycle for SaaS but the construction of a different kind of company, built on AI economics rather than seat economics, on top of SaaS.
Essay · May 2026
The second growth curve
The first growth curve of B2B software, from on-premise to SaaS, is ending. The second, from SaaS to AI-native, has begun. A business-model reset, not a feature cycle.
Memo · May 2026
The SaaS-to-AI-native transition risk
A board-language view of the SaaS-to-AI-native transition risk across product, go-to-market, pricing, services, and capital, with one diagnostic per line.
Memo · May 2026
Your 2026 growth plan is modelled on a buyer that no longer exists
Most software growth plans for 2026 still assume the prior go-to-market motion, pricing, and unit economics while the product becomes an AI product.
Essay · May 2026
AI is a business model reset, not a feature roadmap
Most B2B software CEOs are answering what AI features ship this quarter. The board question is what AI is doing to the business model that ships them.
Essay · May 2026
AI redesigns the C-suite before it redesigns the workforce
AI is being framed for CEOs as a workforce question. It is first a leadership-architecture question, and the C-suite operating model is being rewired before the workforce is.
Essay · May 2026
Pricing is the first AI-native lever
In the shift from SaaS to AI-native, pricing is the first lever to reset, because it is the only one that translates AI margin economics into recurring revenue structure.
Essay · May 2026
When the go-to-market playbook stops working
Go-to-market signals lead product signals when a software business hits its growth ceiling, and boards usually see the break twelve months late because the dashboards smooth it.
Memo · May 2026
Why AI is not yet showing up in the growth plan
Why AI does not appear in the growth numbers, and what would change that.
Operator note · May 2026
A CEO's 90-day AI-native reset agenda
Most AI programmes in B2B software fail in the third to sixth month when the feature backlog catches up with the operating model and nothing moves on the P&L. This is the operator's ninety-day sequence.
Operator note · May 2026
Do not delegate AI strategy to the product roadmap
A CEO who delegates AI strategy to the CPO has chosen the smallest version of the AI question, because product roadmaps optimise inside the business model while the AI question is about the business model itself.
Operator note · May 2026
How to tell whether your AI strategy is theatre
Most software companies have an AI strategy on paper and few have one in the operating model. This is a ten-minute self-audit against five operating tells; three or more, and the strategy is theatre.