Early Retirement - Financial Freedom (Investing, Tax Planning, Retirement Strategy, Personal Finance)

Why Retire Early? History Of The Podcast

• Ari Taublieb, CFP®, MBA • Episode 262

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What if work became a choice, not a requirement?

The Early Retirement Podcast is here to help you navigate the path to financial independence, so you can retire when you want and live how you want. Whether you’re nearing retirement or just starting to plan, this podcast delivers clear, actionable insights designed to simplify your biggest financial decisions.

We focus on strategies that make a real impact—from tax planning moves that may unlock $100,000+ in lifetime savings, to investment and withdrawal strategies that align with your values and goals. It's not about chasing perfection, it's about creating a plan that gives you freedom, clarity, and peace of mind.

Because at the end of the day, early retirement isn’t just about leaving your job, it’s about building a life you don’t want to escape from.

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Advisory services are offered through Root Financial Partners, LLC, an SEC-registered investment adviser. This content is intended for informational and educational purposes only and should not be considered personalized investment, tax, or legal advice. Viewing this content does not create an advisory relationship. We do not provide tax preparation or legal services. Always consult an investment, tax or legal professional regarding your specific situation.

The strategies, case studies, and examples discussed may not be suitable for everyone. They are hypothetical and for illustrative and educational purposes only. They do not reflect actual client results and are not guarantees of future performance. All investments involve risk, including the potential loss of principal.

Comments reflect the views of individual users and do not necessarily represent the views of Root Financial. They are not verified, may not be accurate, and should not be considered testimonials or endorsements

Participation in the Retirement Planning Academy or Early Retirement Academy does not create an advisory relationship with Root Financial. These programs are educational in nature and are not a substitute for personalized financial advice. Advisory services are offered only under a written agreement with Root Financial.

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Ari Taublieb, CFP ®, MBA is the Chief Growth Officer of Root Financial Partners and a Fiduciary Financial Planner specializing in helping clients retire early with confidence.


Speaker 1:

The Early Retirement Podcast started in December of 2020. We are now, as of this recording, in June of 2025. We're nearly five years. We're about four and a half years. This is an episode where I'm gonna tell you about the history of the show, a little bit more about who I am. If you already know all of this because you've been listening for years, you don't need to listen to this episode. If you want an overview, if you're new awesome, I hope you tune in, regardless If you watch my YouTube videos or not.

Speaker 1:

Everything I talk about is for one sole goal I want you to know the earliest time working is optional, where you're working because you want to, not because you have to. That is the biggest thing that I talk about and try to come across. Now, everything I do is for this idea that if you could spend more time with family, or you could spend more time traveling or just on a new career, and if you're smart with numbers, you can get more of that. I mean, how cool is this? I'm not obsessed with Roth conversions. I'm not obsessed with a charitable trust. I'm obsessed with the fact that I'm not obsessed with a charitable trust. I'm obsessed with the fact that, if you use these things well, you can get more time doing what you want to do. That's why numbers are so fascinating to me. You're all humans. You're not robots. I have so many different examples.

Speaker 1:

I've told the story of my dad many times. My dad saved and invested very poorly, but he made a ton of money. He had a great life. He paid for so many things. I'm so grateful. The reason I have the confidence I do today is he paid for so many things, so many private lessons along the way. I'm so grateful.

Speaker 1:

But my dad has concentrated stock. He bought Monster Stock and it's done so well for him. Stock, and it's done so well for him. But I said, dad, do you want that one company to dictate how many surf trips you take in retirement? He's like no way. So I should diversify. I said don't just diversify blindly, do it over time to minimize tax consequences, but also recognize that if there's something that we're seeing that may make you lose sleep, for example, every time monster stock goes down, my dad, he has a notification on his phone. Okay, so his neck starts to hurt sometimes and I go dad, you want your neck to hurt? Now, that's impacting surfing.

Speaker 1:

What's the real risk of holding this monster stock. It's going beyond just okay, the emotional, you know ups and downs. It's now taking up so much of your time and it's is it worth the hassle? What if we diversified it? What if we did sell? What if we did pay this tax bill? Would that be worth it?

Speaker 1:

So I use my parents as examples all the time. I currently am a financial planner. I'm a certified financial planner because my parents were burned by four advisors Now, not burned, as in, their money was stolen. So burned might be the wrong word, but they had many different advisors and my parents great at making money. They needed good guidance. They didn't receive good tax planning guidance. There were conflicts of interest. They were sold products they shouldn't have, in my opinion. Now this show you're listening to right now the early retirement show this was not the original name.

Speaker 1:

Over six years ago, I was working in a company called Nuveen. Nuveen is this big company focusing on tax-free income, municipal bonds specifically. So here I am, learning about tax-free income and optimizing taxes and all this stuff, and I just didn't love it because we're only working with these big institutions. I didn't find a ton of value, I didn't feel I was making a difference, and so I eventually connected with James. James is the founder of Root. I was the first employee to join this company, root Financial. Now we have over 50 team members as of today, and we get to help hundreds of clients optimize their finances where we work directly with them. Help hundreds of clients optimize their finances where we work directly with them. What's also really cool is there are hundreds of thousands of you and millions that actually watch, listen to our content every month who don't work with Root that hopefully still receive tremendous value. So our way of giving back is making all this content for free.

Speaker 1:

Now, if you're listening on the podcast app, no ads. If you're on YouTube, I know there are ads. You can pay for YouTube Premium. I pay personally for YouTube Premium in my life. It is an investment. I found that's worth making, although my fiancee says that I should not have paid for it because now I watch too much YouTube.

Speaker 1:

But beside the point, the point of this episode is to tell you this podcast specifically. You're never going to see me make an episode. Here's the best new credit card of 2025, or I'm going to show you how to travel. Hack with these points and make sure to open a card and then get rid of it after three months and then reinstall a different card and then have your neighbor's dog get a new card. That is not my style. Okay, that is not what lights me up and I don't feel that adds tremendous value. Now there are people that talk about those things and I'm not saying those people are terrible. I'm just saying what lights me up, what really moves the needle in big ways, is helping you understand. Hey, should I be maxing out my 401k because I've done it for 30 years, or should I maybe only put enough money to get the free match, because I love free money, and divert the rest to, maybe, a superhero account where now I have more flexibility around the funds? Maybe I should consider retiring early because of healthcare I normally never would have, but now I see with this superhero account I can massage my income. Guys, these are things that can make big differences in your lives where, if I can give you some actual, actionable insight, you might be able to retire five years earlier and if you get five years earlier with your family. You can't exactly quantify that on some spreadsheet, although I've tried doing stuff like that because I'm an Excel weirdo.

Speaker 1:

My point here. I love what I get to do. Many of you know my joking kind of style. I do not do that to be annoying. I hope my stories don't feel annoying in any capacity.

Speaker 1:

I do this because I had a mentor once who told me, ari, if you do not keep people laughing, no matter what point you're trying to get across, it will not matter. And I challenged him and I said I don't think so. I think if I can clearly make sure my point resonates and give an example, they're going to take away what I need them to take away. And he laughed and said that's so cute, you haven't been in the business long enough. And I then had him show me different examples and I could see through different studies that he was showing me but also the way he was explaining it. I went look, I think you have a point here and it's hard, because I'm a human, to say I'm wrong. I was 100% wrong. I'm seeing him give presentations and I thought he was spitting out gold because I love this stuff. He was saying Ari, there's a spouse who maybe never had a lemonade stand, who probably has never heard of a 401k.

Speaker 1:

The people listening to your podcast, they probably love this stuff. They want to optimize. That's why they're listening. What about that spouse who traditionally is not involved? Are you going to make sure they're completely ignored? How do you get them interested? What questions could you ask them that make them feel heard for the first time in their life regarding their finances? I went that's a powerful question. So I do different jokes. I try to keep it entertaining. I need to educate, because this is what lets me sleep at night. I will wake up and go. There's a point I want to get across. If nobody hears it or nobody leaves a comment or sends me an email, that's okay. I sleep better knowing you heard it. Do I love getting to hear when it's helpful? Yes, because it helps me make different types of content for you guys.

Speaker 1:

But coming up on five years of this podcast, I have no intention to stop. I eventually want to ramp up what I'm doing. I want to have more guests. I very rarely have guests on because I want to do it in my style, and when I bring a guest on, sometimes you guys have shared with me. Hey, ari, it was good, but that person that didn't feel like it was my exact example. I found it was a 30-minute episode that I kind of prefer your 10 to 15-minute style. So I'll do different versions and test it out always. But I would love to ramp it up Right now. On YouTube I'm posting almost every single day, about six days a week.

Speaker 1:

As of today, I am showing you different case studies. I'm going into different examples on how to think about. What are these big levers? What if you retire and get unlucky? You might have head trash. Right now, head trash is one of these phrases I talk about where you might think there's no way I can retire early. I mean, healthcare is going to cost so much and my friends, they're nowhere close to retiring, they're not even talking about it. So why on earth am I even debating this? Am I just being dumb? No, you're not being dumb. You might be really smart and they might not be considering it.

Speaker 1:

There's a joke within my friend group and at the company here, but within the friend group my nickname is the initiator. I'm the one that initiates. Guys, we're taking a trip. I just paid for it upfront. Please pay me back. Here's why we're going to go. I miss you guys If I don't make that action. What happens is we don't go on the trips.

Speaker 1:

Someone might argue okay, well then, your friends aren't that good of friends or whatever. From the outside, it could look like that. That's not the case. They're just not initiators. Someone's got to do it, and I don't mind doing it. Would I like it if all of us talked more about? Hey, let's do it as a team, of course. But that's not the case. Everyone in a relationship has pros and cons, once again, in a romantic and non-romantic relationship. Now, at the same time, whenever I'm thinking about okay, how can I deliver a certain point? What can I do that's going to make this resonate, I'm thinking of analogies, I'm thinking of stories.

Speaker 1:

I've told this one often, but and I think I even told it in last week's episode but I went to a doctor this was a long time ago now, maybe a year and I told the doc what you just said there. I think you believe it sounded great. I really think you thought it hit home and it sounded good. But I'm really sorry, I don't know what you just said, so would you try again? And I will say it that transparently. And then he said I'm so sorry. Yeah, let me explain again.

Speaker 1:

So he starts explaining to me the lab that the pills are made in that he wants to give me. And I said look, I'm really sorry, but I don't want to be difficult here. I don't care about the lab, I just need to know why I'm going to take this pill or why I'm not going to take this pill, and I'm not going to take it blindly. So I'm not trying to be difficult. I don't want to be one of those clients, but I do want to make sure I'm taking this, knowing I can sleep at night. So he said oh, I'm sorry, I didn't know. You didn't want that much detail. So then he did a beautiful job explaining it. I said, doc, you did it. I'm now fully clear. Oh, I'm taking the supplement. That's how you should be working with your advisor.

Speaker 1:

I believe if you have an advisor, you should be able to ask them these questions and go hey, I'm really sorry. I know you seem excited and that says green and not red and I should do the green thing, but I'm just not clear on it. We will ask a spouse who's traditionally never had any interest in financial planning it. We will ask a spouse who's traditionally never had any interest in financial planning If we force you to spend $100,000 this year and if you don't, you can't save it. It's going to your least favorite political party. What would you do? That gets people to open up. Okay, we try to keep it creative here.

Speaker 1:

Some people go Ari, my spouse would have no issue spending more money. It's how do we save more money so we can retire early? Great, different story here. But everything I do is with this concept of an early retirement. There's nothing magical about early retirement. Early retirement to me is are you working because you want to or because you have to? As I see it, I am in an early retirement, yet I don't have enough money to never work ever again. I just love my work so much. If you told me that I would have to pay to do my job, I would. I love what I get to do. Some of you go that's awesome. I don't feel that way. When can I retire? Beautiful, hopefully.

Speaker 1:

The tax strategies I talk about the big ones, guys. I talk about tax gain harvesting. That's how do you pay 0% in taxes when you retire early? Many of you are not even aware that you could create $120,000 of tax-free income. That is an available option to you today. So would you rather work and make $200,000 a year and net after 401ks and insurance and taxes. Would you rather net let's call it 160 on that? Or would you rather do nothing at all and generate $120,000 tax-free? Do whatever you want? Well, that might be more attractive. Now, that option is only available with a superhero account, a reason I preach on this once again, I don't get any commissions on whether you use one account over another. I just want you to make the most money. So, superhero accounts I talk about Roth conversions. This can add hundreds of thousands of dollars potentially more, potentially less over the course of your retirement.

Speaker 1:

Many of you listening, you've saved really well, but you've saved to a 401k. You've saved to an IRA that helps you. Today, you get a tax deduction Over the future. You're going to eventually have to pay taxes on that. Many of you have a lot of money in a single stock. You just sold your company. You have $12 million. You're like, hey, should I deploy this all at once? What about my children? I don't want them to inherit it and now they figure I don't need to work hard. I don't want to create a burden. I also don't want to leave money on the table. I don't want to be so unoptimal that I'm actually looking back at my life going, hey, why didn't I spend more money? So there is a balance, of course, like with anything, but this podcast is designed to help you understand and ensure you're not leaving money on the table unnecessarily.

Speaker 1:

I talk about a lot of different strategies healthcare insurance, estate planning, withdrawal planning. Withdrawal planning is so underrated. Tax strategy I have all my analogies. I have my retirement boxer, where I want you to be dynamic throughout retirement. I talk about cauliflower. Can we eat a little bit of cauliflower, pay a little bit in taxes today to avoid eating a ton of cauliflower in the future, when you're gonna want the steak and you're gonna want the pasta and you're gonna want the good stuff? How do we understand that balance? How can we go deeper and actually understand this concept of recreational employment? Am I working today because I want to or because I have to?

Speaker 1:

This podcast is designed to help you retire early. If I've helped you already in any capacity and you're watching on YouTube, please like this video and comment below what I've helped with, because I love getting to hear from you guys. If you're listening on the podcast app, shoot me a note. There's not a comment section. You can email me at ari, at rootfinancialcom. You can say, hey, this really helped. I'm now feeling this way. You could say you know what.

Speaker 1:

I would love for you to go into more detail on the tax strategy. You used to do it more. Now I want updated brackets. I want to go into healthcare. I want more examples. Should I prioritize healthcare subsidies? Should I do Roth conversions? What if I'm projected to leave 5 million to my heirs? What can I do Roth conversions? What if I'm projected to leave 5 million to my heirs? What can I do to minimize that? Or should I just not even be worrying about that? Should I try to spend more money?

Speaker 1:

One of the biggest things that you guys have told me that I've helped you with is I talk about Roth conversions a lot because a lot of you have saved well to a 401k. You're not getting great tax strategy from other aspects of your life, from your current advisor, and you've learned there's value to eating a little cauliflower today to avoid eating a lot in the future. But you know what a big mistake a lot of you make is. You create this beautiful Roth conversion strategy and you can see if I convert to this bracket for this amount of years and pay taxes today. It could yield hundreds of thousands of tax savings in the future, but you know what you should do instead. Yield hundreds of thousands of tax savings in the future, but you know what you should do instead. You might actually enjoy your life more by retiring earlier, by spending more money.

Speaker 1:

No one has ever come to me at 85 going, ari, I'm just so glad I had the best Roth conversion strategy. I have had people go. I'm really glad I spent more money and helped my kid get that down payment. I'm really glad I retired five years earlier because I got trips that I could never get back because my health took a big shift at 65. Awesome, those are real powerful stories. So it's easy to get lost in this. It's easy to go. Oh my gosh, ari, you have 300 episodes on insurance and tax and estate. Oh my gosh, how am I going to ever get through this? Am I ever going to retire early? No, the reason that I do this is so people like yourselves who save and invest well, reach out and find that when you find it's time to have a partner, so you don't have to have your full-time job in retirement doing this. That's what we do here at Root.

Speaker 1:

Many of you, though, are in your 30s or 40s and you want to retire early, and I'm the weird advisor that says you shouldn't pay us yet. It doesn't make sense to, we can't add value, it's not the right time. Keep saving and investing, but maybe tweak some of these things, giving you some insight, so when it does come time in the future, you might find that this is what you want to do. I have people reach out who go Ari, I love this. When I retire, I'm going to read tax law. This when I retire, I'm going to read tax law. I want to be the one running these projections. And my spouse, I want them to do it too.

Speaker 1:

Okay, I don't hear that too often, but there are people who say that I say great, then don't pay me, it would not make sense. Other people go no, I see the value because I want to spend my time doing what I want, and I want to have a professional, a third party. I want to make sure, if something happens, my spouse is taken care of. I want to delegate and have a partner, because I find value in it, but it's not an all fits one model. One size fits all, should I say the reason what makes Root Root and me me is we're adding this tax strategy component that's so often lost. I cannot tell you how many times people have said I go ask my advisor a tax question, they tell me to talk to my CPA. My, you know. I go ask my advisor a tax question, they tell me to talk to my CPA. My CPA says talk to my advisor. My advisors has talked to my insurance agent.

Speaker 1:

Here I am playing middleman or a coordinator role for retirement. That's not what this is supposed to look like. You're supposed to have a partner, someone who is helping with every step along the way so you can enjoy what you've worked so hard for. Now there is an option that I talk about often in the episodes that I record of this Early Retirement Academy. That is really designed to give you a gut check. There's not specific recommendations. That's a great option if you want to go be your own advisor. Build your own plan, run your own scenario, see what am I on track for.

Speaker 1:

How early could I actually retire? What if it turns out? My inflation assumption should be lower. What if it turns out? You name it. You can go play around. It's a good gut check. What it doesn't do is it doesn't add in that layer of peace of mind, of confidence, of proactive planning. It's not going to say, hey guys, while you're traveling, you should have executed a conversion. And here's the healthcare subsidy that we're going to now shift and, by the way, we're going to do a charitable strategy because you didn't save it, you didn't spend enough money. You told us you wanted to take six trips. You took four. These are the real reasons people work with Root.

Speaker 1:

This podcast, though, is designed to educate you. I hope it's entertaining along the way. Just want to give you some backstory on this podcast, why I do what I do today, and I hope that this was helpful. I'll see you guys next week, back to our normal episodes. Thank you all, as always, for listening to the Early Retirement Podcast. I love getting to host these shows and make different content for you guys every single week. I've not missed a single week in years, and that is because I love getting to do this.

Speaker 1:

Now, please be smart about this. Before you actually execute any strategy that you see me talk about or hear me talk about, should I say Please talk to your financial advisor, your tax preparer, your estate attorney. Please be smart about this. None of this should be construed as financial advice. This is for fun, educational, informational purposes only. Once again, just quick disclaimer here. Guys, please be smart about this. Appreciate you listening, as always, and you can, of course, submit a question on my website, earlyretirementpodcastcom, if you, of course, want me to address a specific case study or topic. I will not promise I can get to it, but I respond to every single person and if I find it will be helpful for a lot of people, I will absolutely make an episode on it, at the very least give you some insight. That's it, thanks, guys.