Building Around Legacy Positions and 351 Exchanges

Making smarter investment decisions isn't about finding the perfect investment—it's about understanding how taxes, fees, and risk impact your outcomes over time.

In this episode of the White Coat Investor podcast, we break down several real-world scenarios that high-income professionals face. We start by discussing whether it makes sense to sell a legacy investment in order to move into a lower-cost option, and how to weigh fees against potential tax consequences.

We also cover how to choose which tax lots to sell in a taxable account, a key strategy that can significantly reduce your tax burden if used correctly.

Additional topics include tax strategies for 1099 physicians, whether MYGAs can serve as a bond alternative, and how organizations like HOAs should approach investing reserve funds.

If you're a physician, dentist, or high-income earner looking to make more thoughtful, tax-aware investment decisions, this episode provides practical frameworks you can apply immediately.

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The White Coat Investor Podcast launched in January 2017, and since then, millions have downloaded it. Join your fellow physicians and other high income professionals and subscribe today! Host, Dr. Jim Dahle, is a practicing emergency physician and founder of The White Coat Investor blog. Like the blog, The White Coat Investor Podcast is dedicated to educating medical students, residents, physicians, dentists, and similar high-income professionals about personal finance and building wealth, so they can ultimately be their own financial advisor-or at least know enough to not get ripped off by a financial advisor. We tackle the hard topics like the best ways to pay off student loans, how to create your own personal financial plan, retirement planning, how to save money, investing in real estate, side hustles, and how everyone can be a millionaire by living WCI principles.

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