What does a winning investment strategy look like? To help show you, I invited my good friend and Fig Tree Cayman investor to join me in this episode. Michael O’Connor brings years of investing experience to help you structure, grow, and protect your wealth. 

Meet Michael O’Connor

·  Michael O’Connor works with a diverse client base and is known for taking a holistic approach to financial problem-solving while designing clear, practical strategies tailored to each person’s goals.

·  As a trusted investment advisor with the Fig Tree Office in Grand Cayman, Michael attracts clients from all over who seek out his tailored strategies to help grow and protect their wealth. His guidance evolves with each client’s changing financial needs and long-term vision.

Building Stable Investment Strategies (00:00:01 – 00:04:51)

·  Michael outlines his core approach of taking conviction-based positions and staying ready to buy when valuations are attractive. 

·  He also highlights Fig Tree’s growth model—up 16% year to date—which blends equities, fixed income, and alternatives tailored to each client’s goals and risk level.

Beyond Investments: Problem-Solving for the Global Elite (00:04:51 – 00:11:58)

·  Michael shares how true wealth management extends beyond markets. He explains the complexities of international tax planning, family business transitions, and multi-jurisdictional structures. 

Investing in Today's Macro Environment (00:14:08 – 00:27:00)

·  Michael shares his guiding philosophy in an inflation-driven, stimulus-heavy environment: "Own things," and avoid excess cash. 

·  He discusses the role of duration management in fixed income and how technical indicators help shape equity exposure.

Life Insurance and Holistic Risk Management (00:32:18 – 00:35:05)

·  His last piece of advice is for families, especially high-earning ones, to have life insurance and basic estate planning.

·  People often delay these financial decisions, but it's important for long-term family security.

 “This year, the winners have been pre-earnings, pre-revenue companies. Investing isn’t easy. It’s about holding conviction and buying when the opportunity arises, again and again.” – Michael O’Connor

Resources

Connect with Michael O’Connor on LinkedIn and explore Fig Tree Group to discover tailored investment strategies.