Can Capital Gains Push Me Into a Higher Tax Bracket?

The first five years after you stop working can make or break your retirement—not because of how much you saved, but because of how you start spending it. Listen in as Jacob breaks down the big shifts that hit early retirees: your investments now need to fund income (and sequence-of-return risk matters), you need a clear income plan with a five-year runway, and this may be the best tax-planning window you’ll ever get before Social Security and RMDs show up. He also explains why spending is often higher than expected early on and why flexibility matters. Finally, he warns against making permanent moves—investment, lifestyle, or relationship decisions—based on temporary market conditions or the emotional adjustment of retirement. 👉 Work With Us: https://www.rivertreewealth.com/get-started

So you have a large HSA in retirement, but what can you really do with it? HSAs are perhaps the most tax-advantaged account out of them all... Better than IRAs and Roth IRAs because an HSA is triple-tax advantaged. You get to deduct contributions from your income, the account grows tax-free, and you can take money from the account tax-free for qualified medical expenses. But in retirement, there are a few other things that you can use an HSA for and that's what I cover in this episode. 👉 Work With Us: https://www.rivertreewealth.com/get-started

What if you could pull $100,000 from your portfolio this year to live on, but only $30,000 or $40,000 of it actually counted as taxable income? It sounds too good to be true, but for a lot of retirees, it's completely possible. In this episode, I break down a strategy called income stacking, how to pull from cash, brokerage, IRA, and Roth accounts in the right combination, and why paying $0 in taxes isn't always the smartest move.

Have you been telling yourself you’ll “just work one more year” to make retirement feel safer? In this episode, Jacob Duke explains that the tradeoff isn’t just financial. Jacob walks through five overlooked costs of working one more year an he encourages listeners to build a real plan to determine whether retiring sooner is already possible and to weigh what they’re giving up by delaying. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers Email: [email protected] Website: https://www.rivertreewealth.com LinkedIn: https://www.linkedin.com/in/jacobduke Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast. DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only. 00:00 The Lie We Tell Ourselves 00:31 Hidden Tradeoffs 01:39 Your Healthy Years 03:14 Ease Into Retirement 04:33 Savings Matters Less 06:09 Missing The Tax Valley 09:25 Stop Moving Goalposts 12:35 What Are You Saying "No" To? 14:58 Build a Real Plan 16:50 Wrap Up

How much cash should you have set aside as you enter the early years of retirement so you can weather market downturns without constant worry? In this episode of Retirement Answers, Jacob Duke explains Rivertree’s bucket strategy: keep two years of portfolio-withdrawal needs in cash (money market) and three years in short-duration fixed income to create a five-year runway, while avoiding being overly conservative and losing purchasing power to inflation. He also walks through how to take withdrawals in practice—generally pulling from what has gone up the most or down the least—and how to proactively replenish cash and bond buckets after strong market periods or following a decline. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers Email: [email protected] Website: https://www.rivertreewealth.com LinkedIn: https://www.linkedin.com/in/jacobduke Jacob Duke, CFP, MBA is the founder of Rivertree Wealth and the host of the Retirement Answers podcast. DISCLAIMER: This should not be taken as tax, legal, or investment advice. All content is for educational purposes only. 00:00 Big Question 00:47 Why Cash Matters 01:35 Bucket One 03:33 Bucket Two 05:37 Avoid Getting Too Conservative 07:42 Allocation Based on Needs 09:38 How to Withdraw in Practice 12:04 Income From Dividends Interest 13:00 Replenishing The Buckets 17:01 Closing