Managing concentrated winners (take half rule)

Cullen discusses options for outsized single-stock gains, the 'take half off' rule, and 351 exchange ETFs.

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#685: You're not an investor. You're a saver.

That's the first of 10 principles Cullen Roche shares in this conversation about building what he calls "the perfect portfolio."

Roche, the founder and chief investment officer of Discipline Funds, argues that when you buy stocks on the secondary market, you're not actually funding companies or making investments in the traditional economic sense. You're just swapping your cash for someone else's stock position – reallocating your savings.

This reframe matters because it changes your entire approach. Instead of trying to beat the market, you focus on the boring, prudent work of allocating your savings across different time horizons.

We walk through all ten of Roche's principles. He explains why you are your portfolio's worst enemy – not just because fear makes you panic-sell during crashes, but because FOMO during bull markets leads you to chase performance at exactly the wrong time.

He breaks down why diversification is the only free lunch in investing, why costs matter more than you think, and why real returns are the only ones that count after you strip out inflation, taxes, and fees.

Roche introduces some concrete strategies most people have never heard of.

The 351 exchange lets you swap concentrated stock positions into diversified ETFs without triggering immediate capital gains taxes.

The "defined duration" approach matches specific pools of money to specific future expenses—like pairing a six-month treasury bill with next year's bathroom remodel.

He also tackles the hardest allocation question: what to do with money earmarked for three to ten years from now. That awkward middle timeframe sits between "keep it in cash" and "put it in stocks," and Roche explains why traditional approaches like sixty-forty portfolios don't always work.

The conversation covers everything from why long-term bonds make terrible matches for long-term goals to why thinking in time horizons beats thinking in investment styles.

Timestamps:

Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths.  (00:00) Principle 1: you're a saver, not an investor

(04:48) Real wealth comes from direct business ownership

(06:43) Principle 2: you are your portfolio's worst enemy

(09:58) FOMO during bull markets vs fear during crashes

(12:43) Principle 3: beating the market is hard

(15:18) The 5 percent "fun money" allocation debate

(16:18) What to do when your position explodes

(17:18) The 351 exchange tax strategy explained

(20:28) Should you rebalance concentrated stock positions

(22:18) Principle 4: diversification is the only free lunch

(31:03) Gold and stock market both high simultaneously

(35:43) When diversification becomes diworsification

(40:03) Principle 5: the cost matters hypothesis