Manager misalignment and strategic drift from their stated promises over time.
The risk of getting lost in the complexity of a strategy, potentially overlooking fundamental flaws in the manager or team.
Underwriting challenges in complex, esoteric asset classes like insurance, which can be internally controversial.
Finding truly uncorrelated assets that meet their high bar for post-tax returns.
Opportunities Identified
The insurance market (specifically the Lloyd's market) is seen as a rare opportunity for relatively uncorrelated, liquid-ish returns in the current hard pricing environment.
Investing in cryptocurrency as a long-duration venture bet on a new technology platform (Web 3.0), analogous to the early internet.