White Coat Investor Podcast

WCI #465: How to Make Smarter Investment Decisions (Taxes, Fees, Risk)

Apr 2, 2026
Eric Wright, an emergency physician who founded 1099 Tax Doctor to help high-earning clinicians with tax strategy. They discuss weighing taxes, fees, and risk when replacing legacy investments. Short talks cover choosing tax lots, S-corps and cash balance plans for 1099 earners, MYGAs as bond alternatives, and how HOAs should invest reserve funds.
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INSIGHT

How To Handle Legacy Investments

  • Legacy investments live in taxable accounts and shouldn't exist in tax-protected accounts because swaps there have no tax consequences.
  • Build around legacy holdings (e.g., add small-/mid-cap funds) instead of selling and triggering big capital gains.
ADVICE

Alternatives To Selling Appreciated Shares

  • Consider alternatives to selling appreciated taxable holdings: sell later, harvest losses, gift to low-tax relatives, or donate appreciated shares to a DAF.
  • Donating appreciated shares avoids capital gains and yields a full charitable deduction.
ADVICE

Use A 351 Exchange To Deconcentrate Stocks

  • Use a Section 351 exchange to swap a diversified basket of appreciated individual stocks for ETF shares to defer capital gains.
  • This can reduce concentrated-position risk and let you build around the new ETF without triggering immediate tax.
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