In Part 1 I explained the strategy, allocations, and overall performance of my alternative portfolio. Here in Part 2, I go deeper into the individual investments — including real estate, GP stakes, litigation finance, music royalties, private equity, search funds and more— along with income, distributions, lessons learned, and future plans. And I also discuss cash management, taxes and what I'm looking at going forward.

Several previous years had unusually strong, across-the-board performance. This year my alternative portfolio behaved more typically, with a mix of cycles across it's diversified holdings. The up-cycle and uncorrelated strategies performed well. And despite real-estate being in a down-cycle (and many similar deals imploding) income was good and illustrated the strengths of vintage year investing and sticking with conservatively structured deals. Here's an in-depth look at my

Real estate's long-term track record is excellent (comparable to stocks in raw returns and often superior on an after-tax basis). So why do I see so many real-estate investors end up with massive holes in their portfolios which they never recover from … and then conclude that “real estate investing doesn’t work”? This Part II does a deep-dive into a real-world example of an egregiously aggressive deal that imploded. It also explains the warning signs that were visible from da

Real estate's long-term track record is excellent — comparable to stocks in raw returns and superior on an after-tax basis. So why do I see so many real-estate investors ending up with massive holes in their portfolio that they never recover from … and concluding that “real estate investing doesn’t work”? This article examines the unintuitive and devastating mathematics of large losses, and how to mitigate that crucially important, but under-appreciated, risk.