About
About
The same pattern. Every sector. Every stage.
Founder-side due diligence, for the founder, before the market runs its own version on you.
Over fifteen years across regulated sectors in the UK and Europe, in three different seats.
I have advised founders from pre-seed through Series A on positioning, market expansion, and investor readiness. In fintech, that has meant working with a founder building across insurance distribution to identify which single segment held genuine willingness to pay, rather than building horizontally across all of them.
I have also sat inside the company rather than beside it. As interim COO for a Web3 startup, a launch pulled more than 10,000 users in 48 hours, and the harder questions arrived immediately after it, what the contracts actually committed us to, and whether the operational structure could carry what we had just built.
I have sat on the funding side. Nine years on a strategic board evaluating grant applications against a cancer research charity's £10M annual innovation investment, deciding which health technologies were backed and which were not.
I have sat on the buying side. Negotiating smart city technology with government procurement departments, local councils, and London boroughs, where the real decision runs through people the founder never meets. I have unlocked seven-figure deployments that had already stalled, and taken a SaaS platform from concept to recurring revenue inside twelve months.
Six years as an Institute of Directors Digital Ambassador, hosting a digital leadership series with CIOs from Boots UK and NFU Mutual, has kept me close to how large regulated organisations actually make technology decisions.
The pattern repeated from all three seats. Smart founders. Strong products. Good execution. Yet something fundamental about the market, the buyer, or the route to adoption had never been tested. It felt like fact because nothing had challenged it yet.
The same pattern. Every sector. Every stage.
Founder-side due diligence, for the founder, before the market runs its own version on you.
Over fifteen years across regulated sectors in the UK and Europe, in three different seats.
I have advised founders from pre-seed through Series A on positioning, market expansion, and investor readiness. In fintech, that has meant working with a founder building across insurance distribution to identify which single segment held genuine willingness to pay, rather than building horizontally across all of them.
I have also sat inside the company rather than beside it. As interim COO for a Web3 startup, a launch pulled more than 10,000 users in 48 hours, and the harder questions arrived immediately after it, what the contracts actually committed us to, and whether the operational structure could carry what we had just built.
I have sat on the funding side. Nine years on a strategic board evaluating grant applications against a cancer research charity's £10M annual innovation investment, deciding which health technologies were backed and which were not.
I have sat on the buying side. Negotiating smart city technology with government procurement departments, local councils, and London boroughs, where the real decision runs through people the founder never meets. I have unlocked seven-figure deployments that had already stalled, and taken a SaaS platform from concept to recurring revenue inside twelve months.
Six years as an Institute of Directors Digital Ambassador, hosting a digital leadership series with CIOs from Boots UK and NFU Mutual, has kept me close to how large regulated organisations actually make technology decisions.
The pattern repeated from all three seats. Smart founders. Strong products. Good execution. Yet something fundamental about the market, the buyer, or the route to adoption had never been tested. It felt like fact because nothing had challenged it yet.
Three moments that made the pattern impossible to ignore
Three moments that made the pattern impossible to ignore
In healthcare AI, clinical teams loved the product. Pilots succeeded. Founders read that as market validation. But the clinicians validating the product rarely held the budget, and the people who did rarely saw the product. Clinical enthusiasm and commercial validation were never the same thing, and nobody had tested which one they actually had.
In enterprise partnerships for an AI diagnostics platform, deals didn’t fail on the technology. They broke on assumptions nobody had recognised until negotiations were already underway, data governance, clinical liability, who actually owned the regulatory risk.
In stalled seven-figure enterprise deployments, each one looked different on the surface and failed for the same reason underneath. An assumption about the buying process, or who actually decided, that had never been challenged until changing course had already become expensive.
Different sectors. Same debt.
In healthcare AI, clinical teams loved the product. Pilots succeeded. Founders read that as market validation. But the clinicians validating the product rarely held the budget, and the people who did rarely saw the product. Clinical enthusiasm and commercial validation were never the same thing, and nobody had tested which one they actually had.
In enterprise partnerships for an AI diagnostics platform, deals didn’t fail on the technology. They broke on assumptions nobody had recognised until negotiations were already underway, data governance, clinical liability, who actually owned the regulatory risk.
In stalled seven-figure enterprise deployments, each one looked different on the surface and failed for the same reason underneath. An assumption about the buying process, or who actually decided, that had never been challenged until changing course had already become expensive.
Different sectors. Same debt.
Why the smartest founders carry the most of it
Why the smartest founders carry the most of it
Confirmation bias means the conversation most likely to prove you wrong is the one that never gets scheduled. Commitment bias means the more capital and time already spent, the harder it becomes to ask whether the original assumption still holds. In regulated markets, founders often carry real domain expertise, banking, insurance, hospitals. That expertise builds conviction, and conviction is exactly what stops anyone testing it.
The research points in the same direction. MIT’s Project NANDA found that 95% of enterprise generative AI pilots deliver no measurable return. Gartner predicts more than 40% of agentic AI projects will be cancelled before 2027. Different studies. Same conclusion. Most failures aren't caused by model capability. They're caused by organisations committing to assumptions that were never properly tested.
Confirmation bias means the conversation most likely to prove you wrong is the one that never gets scheduled. Commitment bias means the more capital and time already spent, the harder it becomes to ask whether the original assumption still holds. In regulated markets, founders often carry real domain expertise, banking, insurance, hospitals. That expertise builds conviction, and conviction is exactly what stops anyone testing it.
The research points in the same direction. MIT’s Project NANDA found that 95% of enterprise generative AI pilots deliver no measurable return. Gartner predicts more than 40% of agentic AI projects will be cancelled before 2027. Different studies. Same conclusion. Most failures aren't caused by model capability. They're caused by organisations committing to assumptions that were never properly tested.
Why I built this
Why I built this
Investors run diligence before they commit capital. Boards scrutinise strategy once problems surface. Customers expose bad assumptions once you’re already in market. None of that exists to help a founder before the commitment is made. I built Assumption Crucible® in 2026 to close that gap.
Assumption Crucible® maps Assumption Debt® across twelve categories sitting under six pressure points, market, buyer, system, company, offer, and delivery, and tests the load-bearing ones through structured conversations with the people who hold real evidence, not opinions. The output is a written
Two ways in. The four week Engagement, for post-seed founders facing a major commitment. The Event Audit, for anyone facing a specific event, a board meeting, a raise, a stalled deal, a regulatory deadline, at any stage from pre-seed through Series A, deducted in full if you proceed to the Engagement.
Your name never appears anywhere. No case studies, no testimonials, no public attribution, ever, without your explicit sign off. If you want an NDA signed before we speak, send it over.
Investors run diligence before they commit capital. Boards scrutinise strategy once problems surface. Customers expose bad assumptions once you’re already in market. None of that exists to help a founder before the commitment is made. I built Assumption Crucible® in 2026 to close that gap.
Assumption Crucible® maps Assumption Debt® across twelve categories sitting under six pressure points, market, buyer, system, company, offer, and delivery, and tests the load-bearing ones through structured conversations with the people who hold real evidence, not opinions. The output is a written
Two ways in. The four week Engagement, for post-seed founders facing a major commitment. The Event Audit, for anyone facing a specific event, a board meeting, a raise, a stalled deal, a regulatory deadline, at any stage from pre-seed through Series A, deducted in full if you proceed to the Engagement.
Your name never appears anywhere. No case studies, no testimonials, no public attribution, ever, without your explicit sign off. If you want an NDA signed before we speak, send it over.
Why regulated markets specifically
Why regulated markets specifically
The detail shifts by sector, regulatory posture and procurement in fintech, clinical validation and deployment complexity in healthtech, broker enthusiasm against underwriting authority in insurtech, data sovereignty in legaltech, procurement frameworks in defence and govtech. The failure mode underneath doesn’t change.
The detail shifts by sector, regulatory posture and procurement in fintech, clinical validation and deployment complexity in healthtech, broker enthusiasm against underwriting authority in insurtech, data sovereignty in legaltech, procurement frameworks in defence and govtech. The failure mode underneath doesn’t change.
How I work
How I work
Not consultancy. Not coaching. Not advisory. I work with a small number of founders at a time, because this depends on understanding how you think, not just what you’ve built, and that can’t be delivered at scale. Every relationship starts with a thirty minute qualification call. If the method won’t create real value, we say so and stop there. No proposal, no process, no obligation.
The goal is simple. Find out which of your assumptions deserve to survive, before the market decides for you.
Not consultancy. Not coaching. Not advisory. I work with a small number of founders at a time, because this depends on understanding how you think, not just what you’ve built, and that can’t be delivered at scale. Every relationship starts with a thirty minute qualification call. If the method won’t create real value, we say so and stop there. No proposal, no process, no obligation.
The goal is simple. Find out which of your assumptions deserve to survive, before the market decides for you.
Start a qualification call
Start a qualification call
Not ready for that yet? The What If tool shows you your own exposure in two minutes.
Not ready for that yet? The What If tool shows you your own exposure in two minutes.