Best Jacob Duke Podcasts (2025)

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Why Starting Over Hurts 37:56

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3d ago37:56

37:56

If you've ever gotten well into a project—maybe a DIY renovation—and then realized that you've taken the wrong approach, you probably know that it's very tempting to just stay the course. Starting all over again would be so painful, even if starting over is clearly the best option. Or maybe you've taken a wrong turn on a hike and only noticed it a …

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Can Capital Gains Push Me Into a Higher Tax Bracket? 13:31

7d ago13:31

13:31

The interaction between capital gains and normal income is often misunderstood, so in this episode, I share how capital gains affect your other income and how "income stacking" works. I also share some unintentional drawbacks of capital gains that you have to watch out for. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ Get yo…

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Teamwork That Works: What Great Teams Have in Common 42:53

17d ago42:53

42:53

What makes an effective team? Talent? Skill? Discipline? In this episode of Choiceology with Katy Milkman, we're looking at some of the more surprising ingredients of successful teams, according to science. Teams where the whole is greater than the sum of its parts. You'll hear the story of the Kon-Tiki expedition—a harrowing journey across the Pac…

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Retiring Early? Use the Rule of 55 To Unlock Retirement Freedom 11:04

23d ago11:04

11:04

Trying to retire before 60? Creating income for yourself can be tough and can cause penalties if you aren't careful... That's where the Rule of 55 can be helpful and allow you to take money from your employer retirement plan without early distribution penalties, if you satisfy all of the rules. In this episode, I share what the Rule of 55 is, why i…

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Are You Over-Saving For Retirement? Here's How You Could Be Sabotaging Yourself 22:14

1M ago22:14

22:14

Is it possible to "over-save" for retirement? I'd argue it is possible and most people don't realize what it's costing them. So, in this episode, I'm sharing how over-saving happens, why it's such a problem, and what you can do to avoid this risk. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ If you want the Important Numbers…

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When It Feels Like Everyone's Watching 36:34

1M ago36:34

36:34

We've all been there. Maybe you fumbled a line in a presentation. Or tripped on a shoelace. Or suffered a bad hair day. It can feel like the whole world is watching you—and judging you—in those embarrassing moments. But are people paying as much attention to you as you think? In this episode of Choiceology with Katy Milkman, we explore why we tend …

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How To Create Tax-Free Income In Retirement WITHOUT A Roth IRA 23:38

1M ago23:38

23:38

Do you really need a Roth IRA in retirement? Personally, I don't think so if you create a good income plan, so in today's episode, I share how a couple with $1.2m can generate tax-free income in retirement without any money in Roth IRAs. Other episodes or videos mentioned: Social Security Tax Video: https://youtu.be/fvrpISbRVak?si=g1qdLsCw-H9LMmYz …

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These 5 Tax Mistakes Will Waste Your Retirement Savings 27:43

1M ago27:43

27:43

Tax planning might be the most consequential part of your retirement plan... If you plan well, you could save yourself hundreds of thousands of dollars over your lifetime. If you don't plan at all, you could give up a huge amount of your hard earned savings. In this episode, I share 5 of the most common tax planning mistakes that I see as a retirem…

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How a Single Source of Information Can Seem Like Several 28:36

2M ago28:36

28:36

You've probably been in situations where multiple friends recommend the same product. It must be great, if everyone is talking about it, right? But then you find out that those friends had all just seen the same product on a popular TV show. What seemed like independent recommendations really came from a single source. In this episode of Choiceolog…

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Retirement Tax Planning: What It Is (Actually) + Why It Matters 23:59

2M ago23:59

23:59

Tax planning in retirement is about so much more than Roth conversions... In this episode, I share the components of a real tax plan and why it is crucial to understand this as you build your retirement plan. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ If you want the Important Numbers 2025 PDF, send me an email! Submit you…

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Coming Soon: A New Season of Choiceology 1:35

2M ago1:35

1:35

It's a new season of Choiceology, an original podcast from Charles Schwab. New episodes arrive every two weeks, so please follow us in your favorite podcasting app. Important Disclosures The comments, views, and opinions expressed in the podcast are those of the speakers and do not necessarily represent the views of Charles Schwab. Data contained h…

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The Widow's Tax Trap: What Is It & How To Avoid It 18:29

2M ago18:29

18:29

There is a tax trap waiting on retired couples, but most don't know about it until it's too late. In this episode, I share what the Widow's Tax Trap is and how you can avoid this big retirement risk. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ If you want the Important Numbers 2025 PDF, send me an email! Submit your questio…

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8 Important (But Little-Known) Rules To Know Before You Retire 18:51

3M ago18:51

18:51

There are so many little details and rules to know about as you head into retirement and today I'm sharing 8 rules that I think everyone should know about before entering retirement. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ If you want the Important Numbers 2025 PDF, send me an email! Submit your question to have it answ…

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5 Things to STOP Doing Before You Retire (And What To Do Instead) 16:02

3M ago16:02

16:02

Getting close to retirement? Here are 5 things you should stop doing before you get started. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ If you want the Important Numbers 2025 PDF, send me an email! Submit your question to have it answered on the podcast: https://www.rivertreewealth.com/questions Email: jacob@rivertreewealt…

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18 Signs You Are Better Prepared for Retirement Than Most People 27:27

3M ago27:27

27:27

Wondering if you are behind on your retirement plan? You are probably more prepared than you think and these 18 signs are good indicators! 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ If you want the Important Numbers 2025 PDF, send me an email! Submit your question to have it answered on the podcast: https://www.rivertreewe…

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Retire NOW If You Answer YES to These 5 Questions 16:21

4M ago16:21

16:21

Knowing the best time to retire is tough to figure out because of all the details involved, but if you can answer 'YES' to these 5 questions, it might be time to start thinking about it! 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ If you want the Important Numbers 2025 PDF, send me an email! Submit your question to have it …

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Why This Account Changes Everything in Retirement 16:14

4M ago16:14

16:14

There is an account that can give you ultimate flexibility and help you reduce taxes in retirement... and no, it's not a Roth IRA. It gives you the flexibility you've dreamed of when it comes to retirement income planning and tax planning. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ If you want the Important Numbers 2025 PD…

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Little Bits of Happiness: With Guests Sally Millington & Ellen Evers 28:27

4M ago28:27

28:27

Were you the kind of kid who devoured all your Halloween candy in one sitting—or savored it daily until, somehow, it was Easter? And when it comes to bad news, do you prefer it all at once or with some time in between? Turns out, the way we bundle or separate life's highs and lows can influence our happiness. In this episode of Choiceology with Kat…

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Why Converting Everything to Roth is a MISTAKE 17:40

4M ago17:40

17:40

Are you making this mistake with your Roth conversions? In this episode, I explain why having some money in your Traditional IRA could save you thousands in taxes. Video on Social Security Taxation: https://youtu.be/fvrpISbRVak?si=-tF8oULLC7t7GmD7 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ If you want the Important Numbers…

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What Most Retirees Don't Know About Social Security Survivor Benefits 25:38

4M ago25:38

25:38

Social Security survivor benefits are really confusing, but in this episode I break down everything you need to know about survivor benefits to help you make more informed decisions. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ If you want the Important Numbers 2025 PDF, send me an email! Submit your question to have it answ…

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Cents & Sensibility: With Guests Melina Palmer & Devin Pope 32:49

4M ago32:49

32:49

Would you pay more for a car with 29,999 miles than one with 30,000? The answer should be no—it's a negligible difference, after all—but research shows that people often do pay more than they should for cars that are just short of certain odometer thresholds. In this episode of Choiceology with Katy Milkman, we look at why a price or an age or a te…

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Social Security Spousal Benefits - Avoid These Common Mistakes 14:54

5M ago14:54

14:54

Most retirees assume they are entitled to 50% of their spouse's Social Security, but that is not true... In this episode, I outline the rules for Social Security spousal benefits, how it works, and why your decision to take Social Security impacts your spousal benefits. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ If you wan…

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What You Can Do To Avoid The IRA Pro-Rata Rule 8:29

5M ago8:29

8:29

Do you have after-tax money in your Traditional IRA? Well, when it comes time to make distributions or do Roth conversions, you could unknowingly pay more in tax that you otherwise have to if you aren't aware of the IRA Pro-Rata rule or how you can fix this issue before it becomes a problem. In this week's Friday Q&A, I answer James' question on th…

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What The Top 1% of Retirees Do Differently From Everyone Else 15:12

5M ago15:12

15:12

The top retirees approach retirement completely different from everyone else. They have an abundance mindset and live with intentionally, and that's what I discuss in today's episode. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ If you want the Important Numbers 2025 PDF, send me an email! Submit your question to have it ans…

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Hooked on Streaks: With Guests Chloë Hamilton & Jackie Silverman 31:27

5M ago31:27

31:27

Streaks have long been logged in the world of sports. And for tracking habits, like daily writing. But now apps encourage us to keep streaks going for just about anything. Messaging friends, learning new languages, meditating, exercising, you name it. In this episode of Choiceology with Katy Milkman, we explore the motivational power of streaks. An…

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Why Your Roth Conversion Could Trigger Unexpected Tax Penalties 17:01

5M ago17:01

17:01

Roth conversions are a powerful tax planning opportunity for retirees, but the devil is in the details. Missing a couple small things could end up costing you. In this Friday Q&A, we answer the following questions: How are dividends taxed in different account types? If I do a Roth conversion, do I need to make estimated tax payments or can I just p…

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10 Retirement Hacks That Will Save You Money 29:07

5M ago29:07

29:07

There are a few simple ways to save money in retirement and keep more of your hard earned money in your pocket. In this episode, I share 10 hacks that will help you save money and reduce taxes in retirement. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ If you want the Important Numbers 2025 PDF, send me an email! Submit your…

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Recession-Proof Your Portfolio By Doing THIS 11:39

5M ago11:39

11:39

What if the market tanks right after you retire? It's important to be prepared and have a plan in place for the 'what-ifs' that could happen. In this weeks Friday Q&A, I answer Carolina's question and share how I like to build portfolios that are recession-proof. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ If you want the I…

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Why You Should STOP Doing Roth Conversions 14:56

5M ago14:56

14:56

Roth conversions might be causing you to pay more in taxes compared to simply not doing any Roth conversions. In this episode, I explain how RMDs and your future tax rate could be much lower than the tax rate you would pay today on any Roth conversions you do. Roth is great, but it isn't always better. 👉 Book a call with me: https://www.rivertreewe…

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Obstacle Illusions: With Guests Daniella McCahey & Tom Gilovich 30:41

5M ago30:41

30:41

First-born children tend to believe that their parents were harder on them than their siblings are willing to grant. Football fans take disproportionate note of the challenging games on their team's schedules. We're wired to interpret our challenges as bigger than our advantages, even if the reality is more balanced. In this episode of Choiceology …

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Planning for Travel Expenses in Retirement? Ask Yourself These Questions 9:22

5M ago9:22

9:22

Trying to figure out how to plan for travel expenses in retirement? That's the question that I address on this week's Friday Q&A. I share a few things to consider as you plan how much you are going to spend on travel in retirement. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ If you want the Important Numbers 2025 PDF, send …

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This is the BEST Way To Do Roth Conversions 14:55

5M ago14:55

14:55

What if you could do a Roth conversion completely tax-free? Would you even believe me if I said this was possible? In this episode, I share how you can use a charitable gifting strategy in tandem with your Roth conversions to eliminate the taxes on the conversion. It's like magic, but it's not... It's just strategy! 👉 Book a call with me: https://w…

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How To Plan For Long-Term Care in Retirement 12:51

6M ago12:51

12:51

Long-term care planning is difficult to figure out. There is no "right" way to do it because some prefer to self insure while others prefer to purchase insurance. In this Friday Q&A, I address Theresa's question about long-term care planning and how I think about it. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ If you want t…

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Stock Market Crash? Take Advantage of These 3 Opportunities 18:01

6M ago18:01

18:01

The stock market might be taking a hit, but that doesn't mean there aren't opportunities out there. In fact, it's times like these the top 1% make the smartest moves. In this episode, I share 3 opportunities that you can take advantage of during market crashes. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ If you want the Imp…

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The Reality Trap: With Guests Ken Adelman & Julia Minson 38:22

6M ago38:22

38:22

Is it ever possible to see the world objectively, as it is? Turn on the news, open social media, engage with that family member at Thanksgiving, and it appears to some the answer is yes. But what if our biggest blind spot is thinking we don't have a blind spot? In this episode of Choiceology with Katy Milkman, we look at how we can easily be fooled…

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How To Invest AFTER You Retire 21:22

6M ago21:22

21:22

You've been investing throughout your entire career and trying to grow your portfolio so you are ready for retirement. But what happens to your investments when get to retirement? Should you make a bunch of changes? Should you be more conservative? Join me as I discuss how to approach investing during retirement and a few different things you need …

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DO THIS To Spend Confidently in Retirement 15:59

6M ago15:59

15:59

The fear and unknowns of retirement make it hard for most retirees to spend confidently. In fact, I think spending with confidence in retirement might be the hardest thing to do. Will you run out of money? Are you spending too much? What if the market crashes and you never recover? All of the "what ifs" lead to under spending in the prime retiremen…

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A Numbers Game: With Guests Linda Chang & Stephen M. Colbert 29:37

6M ago29:37

29:37

Workplaces often rely on numerical ratings for performance reviews. Election debates focus on poll numbers and approval ratings. Your watch counts your steps in a day. Numbers increasingly influence our decisions. In this episode of Choiceology with Katy Milkman, we look at our very human tendency to fixate on digits even when words or graphs repre…

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Sequence of Returns Risk: Should You Retire During a Recession? 19:14

6M ago19:14

19:14

What happens if the market goes down dramatically right when I retire? That's a big question on most retirees & pre-retirees minds, so in this episode, I walk through how you can combat this risk and what you should do to be prepared. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ If you want the Important Numbers 2025 PDF, se…

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Roth IRA 5-Year Rules & A Little Known Fact You Should Know About 9:58

7M ago9:58

9:58

In this episode, I share the two Roth IRA 5-year rules that you should know about. Additionally, I provide a HUGE tip that will help you out when doing Roth conversions in retirement. (Most people don't know this) 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ If you want the Important Numbers 2025 PDF, send me an email! Submi…

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6 Financial Goals to Reach By Age 60 23:35

7M ago23:35

23:35

If you can have these 6 things figured out by the time you are 60, your retirement will be that much more successful and enjoyable. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ If you want the Important Numbers 2025 PDF, send me an email! Submit your question to have it answered on the podcast: https://www.rivertreewealth.co…

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How To Avoid The RMD Tax Trap 28:05

7M ago28:05

28:05

If you aren't paying attention, a huge tax bomb could arise later in retirement. This tax bomb comes in the form of RMDs... But finding ways to minimize your RMDs will help lower your lifetime tax bill. Most people only look at RMDs at surface level, but these forced distributions impact other items such as Social Security taxation and IRMAA, to na…

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Every Retirement Plan Has This MAJOR Problem 14:03

7M ago14:03

14:03

As you approach retirement, you likely want to have everything planned out perfectly... When you are going to start taking Social Security? When to do Roth conversions? How to use tax-gain harvesting? What your portfolio allocation should be? And so on The good news is you aren't alone in your desire to have it all figured out before you jump in re…

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5 Hidden Costs That Catch Retirees Off Guard 17:23

8M ago17:23

17:23

Do you ever wonder what you might be missing as you plan for retirement? There's so much to think about and plan for that certain things can easily slip through the cracks. In this episode, I share 5 hidden costs that catch retirees off-guard based on what my clients have told me. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅…

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The Complete Guide to Backdoor Roth IRA Contributions (And Common Mistakes to Avoid) 22:54

8M ago22:54

22:54

The Backdoor Roth might be the greatest tax loophole for high income individuals… But 99% of people have no idea how to do it correctly. So, in this episode, I’m going to tell you exactly how to do a backdoor Roth contribution without messing it up. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ If you want the Important Numbe…

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6 Common Tax Mistakes Most Retirees Make (And How to Avoid Them) 27:36

8M ago27:36

27:36

Taxes could very easily be your largest expense in retirement. So, having a strategic tax plan might prove to be the most important thing you can do. In this episode, I share 6 common tax mistakes retirees make around withdrawals, Roth conversions, capital gains, & Social Security. 👉 Book a call with me: https://www.rivertreewealth.com/get-started …

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Create Up To $126k of TAX-FREE Income in 2025 Using Tax-Gain Harvesting 12:27

8M ago12:27

12:27

Wait... You're telling me I can sell $126k of gains in my brokerage account and pay no tax on those gains? Yes! (And the best part is... it's legal) Join me as I share how tax-gain harvesting works so you can learn how to implement this tax savings strategy yourself. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ If you want t…

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Every Good Retirement Plan Includes These 6 Things 28:11

8M ago28:11

28:11

How do you know if your retirement plan is good or not? And what are the different things you need to include in your plan? That's what I discuss in this episode because I share 6 things that every good retirement plan includes. 👉 Book a call with me: https://www.rivertreewealth.com/get-started ✅ If you want the Important Numbers 2025 PDF, send me …

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If You Want to Retire in 2025, Do These 5 Things First 22:20

9M ago22:20

22:20

As you prepare for you upcoming retirement, there a few thing you can do to give you the best chance at the retirement of your dreams. In this episode, I share 5 things (plus a bonus tip) that you should BEFORE you retire to help you make the most of your new adventure and rest at night knowing your money is taken care of. Enjoy! 👉 Book a call with…