Independent Strategic Advisory
Senior counsel for the moments that decide outcomes.
Independent analysis of corporate structures, markets and emerging risks — built for decision-makers operating in complex environments where objective insight and asymmetric thinking provide decisive advantage.
Strategic Intelligence
Objective insight, free of institutional conflict.
Obsidian Strategic Advisory provides institutional-grade M&A and transaction advisory to corporate boards, private equity sponsors and family offices navigating high-stakes capital deployment and cross-border transactions.
Independent deal structuring, counterparty assessment and transaction risk analysis — delivered at the principal level, free from institutional or broking conflict, and focused squarely on high-value, transformative outcomes.
Core Areas of Expertise
High-Level Corporate Advisory
Senior strategic counsel to boards, founders and investors navigating pivotal corporate moments.
This includes restructuring environments, activist situations, strategic transactions and complex corporate positioning where the right strategic architecture can materially shift outcomes.
Private Equity & Strategic Acquisitions
Identification and execution of disruptive, value-liberating acquisitions where assets are mispriced, misunderstood or structurally constrained.
Focused on opportunities where strategic insight and disciplined negotiation can unlock disproportionate value.
Cross-Border & Regulatory Strategy
Transaction advisory at the intersection of law, finance and geopolitics — across EMEA and Asia Pacific.
Deep experience navigating FIRB-sensitive inbound investment, multi-jurisdiction regulatory frameworks and concurrent counterparty, adviser and regulator dynamics.
Strategic Intelligence
Independent analysis of corporate structures, markets and emerging risks for decision-makers operating in complex environments.
Asymmetric risk/reward assessment that surfaces high-conviction perspectives unavailable through conventional channels.
The Principal
An accomplished, internationally experienced Corporate M&A lawyer and institutional equities adviser — a project leader across the elite tier of global law and finance, with a distinguished career at Clifford Chance, White & Case and Reed Smith across London, Sydney and Dubai.
As an equities adviser, Simon was a regular commentator for CNBC, Bloomberg Television, Sky Business and ABC Lateline, and was widely quoted in the AFR, Sydney Morning Herald and The Australian on M&A, capital markets and geopolitical risk.
Through Obsidian Strategic Advisory, he now applies the full weight of that institutional and high-net-worth experience to high-value, strategic and transformative transactions — with direct partner-level and board engagement throughout.
Institutional Equities Adviser
Shaw Stockbroking · Wilson HTM- Institutional-grade equity research, market intelligence and investment strategy for high-net-worth and institutional clients.
- Regular on-air commentator for CNBC, Bloomberg Television, Sky Business and ABC Lateline — covering the GFC, monetary policy, FIRB and geopolitical risk.
- Extensively quoted in the AFR, Sydney Morning Herald and The Australian on M&A, capital markets and company specific developments.
- Advisory on events of national and international significance, including the Rio Tinto / Chinalco FIRB rejection, the Stern Hu detention and the Japanese Nuclear Reactor meltdown.
Special Counsel
White & Case LLP- Marquee M&A, leveraged buyout and restructuring mandates for global financial institutions and strategic acquirers.
- FIRB-sensitive inbound investment transactions, including high-profile resource-sector acquisitions and cross-border joint ventures.
- Operated at the intersection of law, finance and geopolitics, with regulatory navigation across multiple concurrent jurisdictions.
Senior Corporate Lawyer
Reed Smith LLP- Major cross-border M&A, private equity and joint venture transactions across EMEA and Asia Pacific.
- Led complex, multi-jurisdiction deal teams — managing counterparty counsel, financial advisers, regulators and senior stakeholders.
- High-value advisory to ASX 200, FTSE 100 and NYSE-listed clients, sovereign wealth funds and global private equity sponsors.
Corporate Lawyer — Senior Associate
Clifford Chance LLP- Progressed to partnership consideration at one of the world's pre-eminent global law firms.
- M&A, equity capital markets and corporate governance advisory for blue-chip institutions, listed corporates and private equity funds.
- Deep expertise in transaction structuring, due diligence management and deal negotiation across the full acquisition lifecycle.
Rio Tinto / Chinalco
Advisory through the FIRB rejection of one of the most scrutinised inbound investment proposals in Australian history.
The Stern Hu Detention
Commentary and analysis on a matter at the intersection of commerce, sovereignty and geopolitical risk.
The Global Financial Crisis
Advised and traded through the defining capital-markets dislocation of the era.
Japanese Nuclear Reactor Meltdown
Market intelligence and strategy through a globally significant supply and risk event.
Featured across CNBC, Bloomberg Television, Sky Business and ABC Lateline, and quoted in the AFR, Sydney Morning Herald and The Australian.
A career built executing the world's most demanding transactions, for the world's most demanding firms — grounded in an elite set of educational experiences from the world's best universities.
Contact
Begin a confidential conversation.
For board-level advisory, strategic transactions or an exploratory discussion, reach out directly. All enquiries are handled in strict confidence.