It’s surprisingly hard to know what something is really worth until someone actually tries to buy it—and that problem is front and center in private funds. Don and Tom unpack why private equity, private real estate, and other “alternative” investments often look calm and stable on paper, only to suffer brutal price drops once they finally trade in public markets. From a Wall Street Journal example of a private real estate fund losing roughly 40% overnight, to Morningstar’s troubling enthusiasm for expensive, speculative new ETFs, the episode reinforces a core principle: prices discovered by real markets beat internal estimates every time. Along the way, listeners call in with real-world retirement questions, inherited IRA rules, portfolio simplification strategies, and a healthy dose of holiday banter.

0:04 What something is “worth” versus what someone will actually pay

1:06 Defining private funds and why valuation is murky

2:27 Private fund pricing versus real market pricing

3:56 BlueRock fund haircut: paper value meets reality

4:24 Market pricing, efficiency, and the wisdom of crowds

5:42 The myth of private investments being “less volatile”

6:27 Real estate as the perfect valuation example

7:39 Listener call: inherited IRA and annuity distribution rules

12:42 Holiday humor, crypto annuity joke, and Kentucky bourbon

16:01 Moving assets from Edward Jones, loads, and simplification

19:41 DIY portfolios versus advisor value

21:08 Morningstar’s “Best and Worst New ETFs” critique

22:21 Why most new ETFs exist (and why you don’t need them)

24:43 Shockingly high ETF expense ratios

26:27 Leveraged crypto ETFs and financial absurdity

27:37 Seasonal podcast plug and ratings gripe

28:44 Listener call: Boeing retirement and rollover planning

34:40 Holiday reflections, gratitude, and comfort over riches

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