About this episode
If you’re sitting on large investment gains in a brokerage account and wondering whether it’s worth taking the tax hit, this episode is for you. I walk through a clear framework I use with clients to help them decide when—and if—it makes sense to realize those gains. I also explain several strategies that can potentially reduce or even eliminate the taxes you might owe, including how to take advantage of the 0% long-term capital gains tax bracket, gifting appreciated assets, and tax-loss harvesting. Whether you're approaching retirement or just looking to be more intentional with your investments, these tools can help you make more informed decisions. Toward the end, I also point to a related video where I explain how a separately managed account may benefit high-income investors with significant brokerage assets. Questions answered: 1. When does it make sense to realize investment gains in a taxable brokerage account—and when should you hold off? 2. What strategies can help reduce or eliminate the taxes owed on long-term capital gains? Submit your request to join James: On the Ready For Retirement podcast: Apply Here On a Retirement Makeover episode: Apply Here Timestamps: 0:00 - When not to sell 2:40 - Understand risks on both sides 5:54 - Tax strategies 8:55 - Gifting stocks to charities 11:14 - Gifting to family 12:44 - Understanding step-up in basis 14:18 - Capital losses offset capital gains 15:11 - Wrap-up Create Your Custom Strategy ⬇️ Get Started Here. Join the new Root Collective HERE!