Retirement Answers

If you’re planning to retire in 2027, the clock is already ticking on the decisions that matter most. In this episode, I walk through the seven things you need to figure out before the end of 2026, from pinning down what you actually spend to building your cash runway and stress testing your plan against the next market decline. Tune into this episode to find out: (00:00) Why millions in savings d...

In this episode, Jacob explains why many retirees make an innocent financial mistake: not spending enough due to fear. He unpacks how a lifetime of saving and watching balances grow makes the psychological shift to spending difficult, and why the first 5 “go-go” years of retirement are often the most valuable for experiences and health. Jacob discusses real-life retirement spending cycles and how...

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 wi...

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 a...

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 tax...

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...

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 ove...

Have you been contributing to a Roth 401(k) for years and assumed that time counts toward the Roth IRA five-year rule when you roll it over? 👉 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: jacob@rivertreewealth.com Website: https://www.rivertreewealth.com LinkedIn: https:/...

Do you really need to be saving more for retirement? What if it's costing you something you can't get back? Join me in this episode to hear a different perspective on how much you should be saving for retirement. 👉 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: jacob@rivert...

Why haven't you sold that investment that has made you a lot of money? What's stopping you? I'm hearing the question "What should I do with my big winners?" a lot more lately, so I wanted to give you some ideas on how to think about this. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2025 PDF here: https://www.rivertreewealth.com/2025-important-n...

Are you worried that required minimum distributions (RMDs) could force unnecessary taxable income and shrink your hard-earned retirement savings? In this episode of Retirement Answers, Jacob Duke explains when RMDs become a real problem, offers a quick rule of thumb based on how much you hold in tax-deferred accounts, and walks through five ways to reduce future RMDs. 👉 Book a call with me: https...

Have you ever wondered if certain beliefs or rules of thumb about retirement could actually jeopardize your future instead of secure it? In this episode, Jacob breaks down the 4% and why it doesn't make sense in real life. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2025 PDF here: https://www.rivertreewealth.com/2025-important-numbers Email: ja...

You've got the savings, the spreadsheet, maybe even the perfect retirement date circled on your calendar, so what's actually holding you back? In this episode, I get honest about the real reason so many people delay retirement, and it's not the money. I share two personal stories and the mindset shift that can help you finally step forward. 👉 Work With Us: https://www.rivertreewealth.com/get-star...

You've spent decades saving for retirement, but are you about to make the same mistakes thousands of retirees only spot when it's too late? In this episode, I walk through the five biggest regrets I see in my work as a retirement planner, and exactly what you can do right now to avoid them. Tune into this episode to find out: (01:14) Regret #1 – Claiming Social Security too early costs you (01:44)...

You're saving for retirement, but are you saving too much into the wrong accounts? Most retirees don't realize this common issue until it's too late. In this episode, I explain why having all of your retirement savings in pre-tax accounts is major risk and how you can begin to fix things. 👉 Work With Us: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2026 PDF here: http...

Have you ever wondered if chasing “more” could actually make retirement harder instead of better? In this episode of Retirement Answers, Jacob is sharing how “more is not better, better is better” applies to retirement...  More money can create fear, over-optimizing can steal joy, more stuff adds complexity and decision fatigue, and more time without purpose can lead to dissatisfaction. Tune in to...

Some of the biggest retirement mistakes don’t show up until it’s too late to fix them. Today, I’m breaking down 8 costly mistakes I see over and over again and how to avoid them before they impact your income, taxes, and long-term freedom. A few small adjustments here can make a massive difference later. 👉 Work With Us: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 202...

Not sure when to take Social Security? Well, in today's episode, I am sharing 5 reasons you shouldn't take your benefits early and the hidden risks of doing so. 👉 Work With Us: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers Email: jacob@rivertreewealth.com Website: https://www.rivertreewealth.com Link...

If you don't get things right during this important window of time, your retirement likely won't be what you hoped... This 10 year period of time will determine the trajectory of your entire retirement. Prepare correctly and you will enjoy a fulfilling life without worry. Little preparation and poor execution and you will be wishing you could get a do over... Only problem is, you get one shot at r...

Confused by the Roth IRA 5-year rule? Did you know there are two different 5-year rules? Well, it can get quite confusing, so this episode is meant to be your complete guide for everything around the Roth 5-year rules. 👉 Work With Us: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers Email: jacob@rivertr...

Are you sure your retirement plan is optimized for the right things? In this episode, I discuss what the true mark of a successful retirement plan is and why most people's plans will fail, just not in the way they expected. 👉 Work With Us: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2026 PDF here: https://www.rivertreewealth.com/2026-important-numbers Email: jacob@ri...

Is the brokerage account the secret to a fun and tax-efficient retirement? It might be a requirement, but it definitely helps. In fact, the brokerage account is my favorite account type and in this episode, I share 7 benefits that anyone can use to their advantage in retirement. 👉 See If You're a Fit: https://www.rivertreewealth.com/get-started ✅ Get your Important Numbers 2026 PDF here: https:/...

Are you still trying to decide when to take Social Security? Well, in this episode, I am deviating from my normal stance to share 4 reasons you might want to take your benefits ASAP rather than delay. And be sure to listen to the end, because I share why using a traditional break even analysis in your decision making process is not a good idea. 👉 Book a call with me: https://www.rivertreewealth.c...

Are you anxious about an abrupt transition to retirement? In this episode of Retirement Answers, I share the concept of phased retirement, where you can gradually reduce work hours or stress levels instead of stopping work entirely. I explain the financial and emotional benefits, offering practical advice for a smoother, more comfortable path to retirement. 👉 Book a call with me: https://www.rive...

Have you ever wondered if your HSA contributions could cause unexpected issues as you approach retirement? In this episode, I highlight potential risks and mistakes that individuals near or in retirement might encounter with their HSAs.  Specifically around scenarios such as switching into an HSA plan mid-year, transitioning out of an HSA plan mid-year, and moving from an HSA plan to Medicare.  👉...