Structural Stress Test
Most tokenised structures are never tested until someone tests them — a lender, a regulator, an institutional counterparty. Sestina finds where they break first. Ten business days, written findings, one walkthrough call.
The problem
Structural problems rarely announce themselves. They surface during investor due diligence, at a banking application, or when a regulator asks a question that should have had an answer years earlier. By then the options are narrower and the cost is higher.
The structure was never built so that a lender could perfect a security interest in it. Nobody noticed until the lender's counsel asked.
Lawful in its home jurisdiction. The only passporting route requires an authorisation no issuer in the EU has yet obtained.
Marketed as ownership. In substance an unsecured claim against the issuer, discovered during due diligence.
The engagement
A fixed-scope assessment across five layers. Each is tested against what will actually be asked of it — not against a checklist.
What you receive
Your structure mapped in full
Findings ranked by severity
The target structure, with reasoning
A sequenced plan to close the gap
A 60-minute walkthrough call
Turnaround
10 business days
Format
Written report and walkthrough call
Layers
Legal ownership, cash flow rights, custody and control, regulatory position, stress scenarios
Why Sestina
A law firm covers one layer. A tokenomics specialist covers another. Most failures sit between the layers, where neither is looking.
Regulatory position is a design input, not a review step. Token structures designed around legal constraints hold; structures where compliance was added afterwards do not.
Scoped, timeboxed, delivered. Ten business days from complete documentation to written findings.
Client feedback
"Frederik is super knowledgeable and super friendly. He advised on the best approach for our business in a detailed manner by reviewing several jurisdictions and sharing his personal thoughts. I definitely recommend him."
Blockchain structuring
Tech company, Belgium · 2023
"Frederick was a pleasure to work with! He provided me with some valuable insights into how to best optimise my tax structure. I would highly recommend if you're looking for an experienced International Tax Specialist!"
International tax structuring
United Kingdom · 2024
"His answers were clear, structured, and highly relevant. He listens carefully, understands the context quickly, and provides honest, well-thought-out feedback rather than generic recommendations."
Regulatory and strategy advisory
2025
Who we work with
Sestina works with Web3 founders who have raised institutional capital and are navigating the structural decisions that determine whether a project survives regulatory scrutiny, closes its next round, and builds something that lasts. Too sophisticated for generalist advice. Too early for the Big Four.
How it works
01
A 30-minute call to understand your structure and confirm whether the test is the right starting point.
02
Ten business days of structured analysis across the five layers.
03
A written report and a 60-minute walkthrough of what we found and what it means.
04
Where remediation work is needed, we scope it. Where it isn't, you have a clean picture and no further obligation.
Capabilities
The test draws on all of them. Individual engagements are available where a narrower scope fits.
Entity design across BVI, Cayman, Switzerland, Singapore and the UAE.
Mechanism design and distribution within regulatory constraints.
MiCA, CASP licensing, AML and KYC, and multi-jurisdiction mapping.
Revenue design, unit economics, and go-to-market structure.
RWA issuance structuring, custody, transfer restrictions, securities analysis.
Investor narrative and term sheet preparation.
About
Sestina was founded by Frederik, a legal and business advisor who has worked with blockchain and digital asset businesses since 2016 across legal structuring, regulatory compliance, token design and business model. Most engagements begin the same way: a founder who has been told their structure is fine by someone who only examined one part of it.
Get in touch
Thirty minutes on your structure. No pitch, no obligation — we'll tell you whether the test makes sense for where you are.
Or email directly: hello@sestina.io