Managing Concentrated Stock in Retirement episode artwork

EPISODE · Apr 9, 2026 · 1H 6M

Managing Concentrated Stock in Retirement

from Making Retirement Make Sense · host Dana Anspach CFP®, RMA®, CJ Miller CFP®, RMA®, CPWA®

The emotional attachment to a company that helped you build your wealth can make it difficult to make rational decisions about when to sell. This episode breaks down the data showing why only a small fraction of stocks create long-term wealth and how you can use strategies to transition out of a concentrated position while maintaining your financial security.Chapters:00:00 Retirement Landmine Intro00:44 How Much Is Too Much03:33 Intel Crash Cautionary Tale05:03 Biases And Stock Odds21:40 Planning Tools And Exit Strategies36:34 Exchange Fund Basics37:30 Capacity And Diversification Limits39:13 Lockups And Tax Reality41:03 Collars For Downside Protection46:02 Direct Indexing Tax Harvesting49:09 Tracking Error And Wash Sales51:30 Beware Shiny Tax Products55:22 Opportunity Zones Reality Check56:23 Leverage And Margin Loan Risks01:05:33 Wrap Up Key TakeawaysLinks & resources from this episode:- Hendrik Bessembinder study: https://papers.ssrn.com/sol3/papers.cfm?abstract_id=3537838- Visit our website: https://makingretirementmakesense.comFind the full audio show wherever you get your podcasts: - Apple — https://podcasts.apple.com/us/podcast/making-retirement-make-sense/id1865029561- Spotify — https://open.spotify.com/show/2eOvIUMulgZUzUTGpzYrtsLIKE & SUBSCRIBE for new videos every week: https://www.youtube.com/@MakingRetirementMakeSenseFollow Making Retirement Make Sense on all social platforms:- Facebook: https://www.facebook.com/profile.php?id=61580093698229- LinkedIn: https://www.linkedin.com/company/MakingRetirementMakeSense/- X: https://x.com/MRMSPodcastDisclosureThis channel contains general educational information only. Nothing contained herein should be construed as a solicitation to buy or sell any security or as an offer to provide investment advice.

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