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Join Teaching Tax Flow for episode 190, where Chris Picciurro and John Tripolsky explore the intricacies of life insurance and its notable impact on tax strategies. In this riveting discussion, Jason Weiss from Symphony Life shares invaluable insights into the role of life insurance beyond the conventional view, illustrating why it's a critical component of smart financial planning.
Throughout the episode, Jason illuminates the audience on when life insurance becomes essential, challenging the typical perceptions tied to family circumstances. With keywords like "tax-free income," "cash flow management," and "insurance acquisition," the conversation delves into life insurance's dual advantage as a secure asset and a tax-sheltering vehicle. The episode also navigates the complexities faced by business owners, emphasizing the significance of insurance for protecting both personal and business interests.
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Throughout the episode, Jason illuminates the audience on when life insurance becomes essential, challenging the typical perceptions tied to family circumstances. With keywords like "tax-free income," "cash flow management," and "insurance acquisition," the conversation delves into life insurance's dual advantage as a secure asset and a tax-sheltering vehicle. The episode also navigates the complexities faced by business owners, emphasizing the significance of insurance for protecting both personal and business interests.
Your Life Insurance Connection:
https://bit.ly/life-insurance-srp
"Defeating Taxes" NOW Available on Amazon
https://www.defeatingtaxes.com
⸻
EPISODE SPONSOR
REPStracker
⸻
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- (00:01) - Exploring Life Insurance and Tax Planning with Jason Weiss
- (03:57) - Understanding Life Insurance Acquisition and Its Importance
- (09:08) - The Importance of Life Insurance for Business Owners and Families
- (12:07) - Exploring Life Insurance Options and Financial Planning Strategies
- (19:10) - Discussing Taxes, Life Insurance, and Financial Conversations
- (21:16) - Investment and Advisory Services Through Cabin Entities
Creators and Guests
What is Teaching Tax Flow: The Podcast?
Welcome to “Teaching Tax Flow: The Podcast”, the show that’s all about demystifying taxes and helping you keep more of your hard-earned income in your pocket.
Hosted by tax experts from the Teaching Tax Flow team, this unfiltered (but clean) podcast is designed to empower you with the knowledge and tools you need to confidently navigate the world of taxes. We’ll cover everything from understanding tax laws and regulations to maximizing deductions and credits.
In each episode, we’ll break down a specific tax-related topic in a clear and accessible way, providing practical tips and strategies you can use to optimize your tax situation. We’ll also answer listener questions, share the mic with amazing guests, and share real-world examples to help illustrate key concepts.
Whether you’re a freelancer, small business owner, real estate investor, or just looking to understand your taxes better, this podcast is for you. So tune in, take notes, and start building your confidence in taxes today.
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www.TeachingTaxFlow.com
Hey, everybody, and welcome back to the Teaching Tax flow podcast episode 190. That's right. We're only 10 away from the big two o o. You know, it's not like it's our 20 birthday. We'll call it the 200. So it's another milestone for us. Today though, as you probably read in the title or somebody shared this link with you for this specific podcast, we're going to go back a little bit and re answer and elaborate and dive deeper into those questions that relate to when do I need life insurance? And actually how that ties in with taxes and why you're here as a whole as part of teaching tax flow in the community. We're gonna get into it here in just a moment. But Chris Picciurro, welcome back to your own show, sir. I know we've a great guest joining us. And if I remember right, he has a great way of explaining, you know, an analogy of how life insurance is. So I look forward to that. But how are doing, man?
Chris Picciurro, CPA:I am doing great. Very excited to have our special guest on today. I know I talk about this sometimes, but in the private CPA firm where I'm helping clients one on one, I get to interact with strategic partners and people that that we work with, we eat our own cooking with. And and then once in a while, I get to bring those people into the podcast for the masses, and those and everyone has that opportunity to glean that knowledge that's usually set for these private rooms and these private, you know, meetings. Now, of course, we're not gonna use names in the as far as clients, but just excited to bring you into that world.
Chris Picciurro, CPA:So we have an amazing special guest. John, you nailed it. Life insurance is part of tax planning. Make no doubt about it. In teaching tax flow, we know that the goal diagnosis, which is tax free income and growth, is very, very important.
Chris Picciurro, CPA:And the goal remember, legally and ethically reducing the tax you pay in your lifetime. It doesn't say legally and ethically reducing my my income tax, we're talking about estate tax planning. We're talking about making sure that people that are relying on you are taken care of financially. And and so we're gonna be, you know, we're gonna be diving into this topic. Jason Weiss of Symphony Life is joining us.
Chris Picciurro, CPA:Someone that we've but, John, you both you and I have had the pleasure of working with, meeting with. So I will without further ado, welcome, Jason. Thank you so much for joining the
Jason Weiss:Chris, John, awesome to be here. This is gonna be a lot of fun. Thanks for having me.
Chris Picciurro, CPA:Well, we are excited to have you, as I said. Before we dive into that question, when do I need life insurance? What what got you into this this type of business with Symphony Life? And I know you've, you're very accomplished professionally. I know you're you, have a you're an attorney as well, but, obviously, this is a passion for you.
Chris Picciurro, CPA:So we'd love to hear a little bit just about a little history and and how you got to the the pinnacle of your career being on this podcast.
Jason Weiss:Yeah. Yeah. This is it it truly has been a good career. And and quite honestly, being on your two hundredth podcast and your two hundredth year, you don't look a day over a 100 and nineties. Chris, you look great.
Jason Weiss:So as you alluded to, attorney by trade, twenty seven years since I, became an attorney. Kinda early on, we would help clients on a lot of different things. And and if you're a business owner watching this, you probably experienced this problem, which is you're looking to scale, you're looking to grow, but you always have to manage cash flow today. And that's kind of what the name of the podcast even. It's you you're managing cash flow always.
Jason Weiss:So we looked at it as a bunch of attorneys. Hey. Listen. Any asset you're buying, insurance I know today, but any asset, it's a car you're gonna buy or a piece of machinery, you could acquire assets one of three ways. You can rent an asset, I can rent a car, I could go buy an asset all cash, or I could buy an asset with financing.
Jason Weiss:There's three ways to buy an asset. And when we found out early on, when we started applying that to insurance, we played the insurance, most people, they kind of had their head cocked. They go, What do you mean? I know I can get term insurance, or maybe I can buy insurance, but you can get a bank to buy it or bank to buy it and pay the premiums? And we said, Yes.
Jason Weiss:And we found out early on, Chris, is if we knew how to acquire asset, but the insurance agent doesn't, What else doesn't that insurance agent know? So again, we took a deep dive again, this is twenty years ago, to the insurance space and not just the asset, which is insurance, but the best and most effective ways to fund and acquire that asset. So we truly come at it both ways, which is what is the what type of policy should you get, and then what's the most efficient way to buy and acquire that asset?
Chris Picciurro, CPA:Right. And based on your seasonal life and maybe where where you're at with your family structure or maybe you're single, that can drive this. So what are some of the main trigger points for someone before they figure out how they're going to finance or or acquire the insurance to realize I do need insurance? Because I think that a lot of times people just unfortunately assume, oh, once I start having a family, once I have a child, now all a sudden, I magically need life insurance. You you know, what are some of those triggering points that people might not be aware of and some of the ones that are pretty common?
Jason Weiss:Yeah. So so so broadly speaking, and I kinda say this, my daughter is 14 years old. She does not need car insurance. She's 14. But you could argue she could get life insurance.
Jason Weiss:So the broader question of when should I kind of take a look at life insurance is kind of any time. Now, when we say any time, there's a couple moments of your of your career where things will happen where, you know, life insurance is something I I should really have a strong conversation about. And that is as you alluded to. If you're acquiring assets, a home, cars, as you're acquiring assets, having insurance around those assets is a is a conversation we had. Then as you kind of move down the trajectory, if you have a business, kind of those kind of things, as you're growing a family, those kind of things.
Jason Weiss:And then quite honestly, insurance, aside from even being life in the death benefit comportion, is one of the few tax free assets that we have available for us. So if you're interested in tax free money, it's, again, one of those things that you should look at. So the the answer to your question, Chris, you can have that conversation anytime. Now it's different policies and different ways to acquire it, but I if you're listening to this podcast and you have not had a a life insurance conversation in a couple years, I would encourage you to have one.
Chris Picciurro, CPA:You know, I find from personal experience, to be very transparent, I started my CPA practice when I was 27. I would was not yet married, didn't have children, and I had a a a policy through my employer. Right? And I was a CPA, you know, and then and then a master's in business administration. I'm not trying to pat myself on the back.
Chris Picciurro, CPA:I'm just saying, I was in that world, but kind of forgot to realize, wait. My I left my job, started my practice. I don't have life insurance. And then I thought, you know, four months later, I end up buying a small book of business that had a couple of employees, and it hit me. If I get hit by a beer truck right now, I'm putting the livelihood of people that were were shedding blood, sweat, and tears together for.
Chris Picciurro, CPA:And I felt at that point, even though I didn't have dependence, I had people relying on me. And and I went out and, you know, got life insurance at that time, and then it ended up evolving into, you know, into a more advanced, structure. However so the point is, you know, there's a saying you're never gonna be as healthy and as young as you are now. If you're thinking, should I need it? I would on the side of caution and at least look at it because, you know, even for people on a budget, couldn't couldn't they, potentially, you know, lock into maybe a term policy and convert it to to a more permanent policy later?
Jason Weiss:Chris, you hit the nail on the head right there. Is I if you look at insurance in general and all the different insurances from homeowners insurance, a car insurance, a commercial insurance, you can buy any insurance anytime except for life insurance. Life insurance is the one you have to qualify for. So if you say someday I'll get life insurance, well, day may be dictated by an insurance carrier that says you don't qualify. So I always say is get the optionality today of getting the the ability to get life insurance in the future by to what Chris you just alluded to is simple term insurance.
Jason Weiss:Term insurance is basically one of those things you have as a placeholder. I call it as an option to one day converting it, dropping it, doing whatever you wanna do, but it locks in your health rating at whatever age and health you are today.
Chris Picciurro, CPA:In doing tax and estate planning from my side, I I can't tell you how many times I've had the situation worse. I've had teachers. My my wife's a teacher. Now she's a school counselor. But teachers, you know, have retire, and they realize that they might not have any life insurance because they're depending on their situation.
Chris Picciurro, CPA:Their employer sponsored life insurance is is not there. And quite frankly, let's be honest. When you're, you know, 60, 65 years old versus 25 years old, your health is you know, everything could be could be different. So kind of other situations, you know, I I think a lot of times business owners forget that, especially if you have business partners or people relying on you, it's not only something that you should consider. It's something that you to me, the people that you're not just your family, but your people that you're working with.
Chris Picciurro, CPA:And, let alone it could be an asset as well.
Jason Weiss:That's right. And inside the business, you've got two concepts working with you. If you're a business owner and you've got partners, one of it is if you have partners, a lot of people have what's called buy sell agreements, which is if one of the partners something happens, the other partner gets to buy or sell the other shares. What I always say is if you have that, but you don't have life insurance, where are you getting the money to buy that other person's shares? Number is number one.
Jason Weiss:And number two is if you have a surviving if you have a partner in your business and that partner dies, you're now business partners with that person's spouse. So having life insurance in that context allows you, if you already be the surviving owner, have the money from the life insurance, the ability to pay off the spouse, therefore making a clean transaction. The second part is this. You ask any business, any business, Chris, your business, my business, anyone listening's business, the most important assets to most people's business is their people. Is their people.
Jason Weiss:It's not the piece of machinery. It's not the building you're in. It's the people that make up the business. So I always say is, if we have commercial insurance, heck, if we have insurance on the copier behind us, we have insurance on our on those hard assets. Why don't we have the same level of insurance on the people that make up our business?
Jason Weiss:And again, this is not expensive things. These are just things that I would be doing. We don't think about as far as like ensuring key people in our business. Absolutely. And and and if you're married, you have
Chris Picciurro, CPA:a key person in your you're you have a spouse. You're in you know, again, another piece of transparency. My wife doesn't want listen to podcast, so that's which is probably a good thing because I'm gonna confess some things. But, no, in in all seriousness, if whether being a teacher and I've had I've had buy sell agreements funded. I've I've taken care of a lot of things business wise.
Chris Picciurro, CPA:However, you know, it hit me once we had our the children. I'm thinking, okay, if if I'm the, you know, I I had the higher income and she actually stayed with the kids for a while. If something happens to me, I wanna make sure she's taken care of. What if something happened to her? I can't work the hours that I'm working.
Chris Picciurro, CPA:I can't I would have to change my lifestyle especially when my kids are super younger. And at that point, we started we looked at insurance for her. So if you are were you know, in a in a marital situation or even if you have a, you're unmarried and you just have a significant other you live with and one person, you know, is makes makes a good I don't wanna say breadwinner, but has a significant amount of income, and the other one maybe is more of a homemaker, you need you need coverage on the homemaker. And I'm always looking for those gaps, you know, those buy sell gaps, those situations where I've seen it from a financial and tax perspective blow up in a bad way because people weren't properly taken care of.
Jason Weiss:And, Chris, on top of that, I I I said, if you're listening to this, remember what I also said, there is three ways to acquire the insurance. This is not about having a big sum of money being tied up, that kind of thing. We can look at renting the insurance for a period of time you need it, or quite honestly, if you haven't looked at it, we can look at having a bank pay those premiums for you, and that's another option. Remember, every asset could be acquired one of three ways. Rent it, buy it all cash, or having a bank finance it.
Jason Weiss:If you haven't looked at all three, you haven't looked at the best way to fund potentially that liability.
Chris Picciurro, CPA:Well, and and remember that 99.9% of the time, your insurance proceeds from life insurance, guess what? We're all gonna pass away. So someone's gonna get these proceeds. That's gonna be tax free to someone, and that is very powerful. I wanna take a step back.
Chris Picciurro, CPA:It it's kinda tied together to that that person that has never thought about life insurance that that maybe they have a little anxiety about even stepping forward. Maybe they've got a health issue. What's, like, the first step someone should consider, in in some of their best practices to and I we got you know, to be transparent. And and at what point do does medical underwriting come into play in general? I know each carrier is a little different, but I'm trying to maybe put people's mind at ease at that are watching.
Jason Weiss:Yeah. And and that's one of those and misconceptions about life insurance is that is they've heard about one product or one type, and they go, it's all that way. And I says, there is different products, different carriers for every type of situation. So if you're somebody and I would say is this, the analogy kind of would be also is this as well. If I walked into the Chevy dealership looking for a car, I walked into the Chevy dealership looking for a car.
Jason Weiss:Am I walking out with a Ford? Probably not. I've walked into a Chevy dealership. And I always say is this people something that says I've walked into whatever insurance carrier they've walked into. That insurance carrier is selling that product of that carrier.
Jason Weiss:When quite honestly, the best product for you may be a totally different insurance company. So you wanna get with somebody like ourselves that kinda independently looks at all the carriers because if you've got a health issue or if you're extremely healthy or what or if you've got two kids, no kids, you've got a business, you don't have business, like, you need somebody that's gonna advise you of the all the carriers and the best product or car that fits your needs at your time, and then marry that with the best way to acquire that product. You wouldn't just look at an asset and be like, there's the asset I want, but I have no idea I'm gonna buy it. You'd kinda look at it in tandem, and that's what we do.
Chris Picciurro, CPA:And to wrap it up, I as as you just gave me the car analogy, you and I love to use analogies. You know, many vehicles come with a warranty. Right? And maybe part of a life insurance policy, especially for my wife and I who we have are are both of our parents living out of state, is a disability rider. Right?
Chris Picciurro, CPA:Because the, quite frankly, the chances that you become disabled are much more than you pass away under, you know, let's say the age of 50 or 40. So, I look at the disability as pieces is kind of a like like a warranty on on the policy. Are you finding the most, you know, policies or most, you know, I say taxpayers all the time. Right? You know, most people look for that disability rider as part of their life insurance as well?
Jason Weiss:They do, Chris. And I think that the biggest gap in the marketplace is is this.
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Jason Weiss:Is most people, against life insurance. They're not against disability insurance. They're not against long term care insurance. We're not against it, but we just don't want to pay maybe those premiums. We want to pay that sizable premium.
Jason Weiss:And it's no different than I said to everyone listening, hey, the house you're living in today, if I said you cannot have a mortgage, you cannot have a mortgage, you had to buy that house all cash, and you had to tie up all your capital in that house, you might say, let's look at renting. I don't have to tie up all my money.
Chris Picciurro, CPA:Right.
Jason Weiss:And so I'm saying is a lot of times we want the insurance, but we've never been exposed to the different ways that are available to fund that insurance. So again, if I could say to you, hey, let's get disability insurance to cover if you got sick or injured. Let's cover the life. Let's cover long term care expenses. Let's cover it, Well, let's not tie up our dollars today.
Jason Weiss:That might be a conversation worth having.
Chris Picciurro, CPA:And and I agree. And just as we we put a put a bow on this, I'm telling you that it's so important as we talk about in the teaching tax law community to build your broader directors. And, you know, in looking at when you're doing tax and financial planning and risk management, they all tie together for, you know, and and I can't tell you how many times that we've we've worked with with people that are, you know, that that maybe they're gonna get a pension. Maybe they work for the state and and they're married and and they're concerned that, you know, they wanna get the best result possible so you can so they wanna have theirs you know, if when they retire, they get the highest amount of monthly capital, but they're worried about their spouse, and you can hedge those bets with life insurance. So it's really a important piece of someone's puzzle is my point.
Chris Picciurro, CPA:And and That's right. We're we're excited that that, yeah, you're to get provide us with with the knowledge you have. And again, we're excited that you're part of teaching taxable community.
Jason Weiss:I'm excited to be a part of it. I will also say parenthetically is if you haven't looked in life insurance with the cash value component of life insurance, we've talked a lot about the death benefit component, why it have a death benefit life insurance. But the cash value associated with life insurance, again, is a liquid, tax free, tax free on the growth, tax free on the distribution. I'll also kind of say this. Anytime anyone has ever heard of super creative tax strategies around distribution of assets like so and so paid no taxes on this, It always involves an insurance based product.
Jason Weiss:Always, always, always because it's the only thing that comes out tax free. And so I always say is if you haven't looked at life insurance as a tax free distribution vehicle, it may be something you want to take a look at.
Chris Picciurro, CPA:Absolutely. And, you know, it's funny because. People look at their mortgage and refinancing their mortgage all the time. And so final thought is if you have a policy in place. Take a look at it.
Chris Picciurro, CPA:We always take a look at our board. Like, you know, take a look at a a restructuring that or refinancing it, and to get you maybe the better results. So, Jason, again, thank you so much. John, thanks for thanks for all your input today, John. We appreciate you.
Chris Picciurro, CPA:Oh, yeah. You know, this this is a rarity and my wife does not listen to this show, but she should because that way she realizes that I can't actually shut up and not say anything for an extended period of time. She'd be proud maybe. We'll see. But honestly, both of you, I think we accomplished the goal
Jason Weiss:of this.
John Tripolsky:Right? Like, we took something that a lot of people actually, we took two things that maybe a lot of people avoid. They avoid taxes or try to, and they avoid having any conversations around life insurance. And I'll wrap with this one. If I'm I almost guarantee a lot of people are listening to this or watching this, and they say, oh, man, I don't wanna talk to anybody about this.
John Tripolsky:And I'm glad I can say this because we're recording this virtually, and both of you are about, I don't know, 600 miles away from me. For the longest time, I tried to avoid anybody that's a financial adviser or tax related and anybody that wanted to talk to me about insurance. And those are probably the most impactful conversations you can have. And Jason, I really appreciate you talking about it and and really emphasizing the fact that you don't you're not gonna walk in. You're gonna have a conversation with someone.
John Tripolsky:They're gonna say, yes. This is the water bottle for you. This is the only one we have. You have to go with this one or don't get anything at all. That's there's options for everything.
John Tripolsky:So I look forward to the rest of our conversation, man. We'll, we'll have to have you back here if we didn't scare you off.
Jason Weiss:Thanks, John. Thanks, Chris. I I hope to be around for 200 plus someday.
Chris Picciurro, CPA:Alright. Let's do it. Let's do
Chris Picciurro, CPA:it. Hope they're here.
Chris Picciurro, CPA:Current policies don't pay before then. Right?
Chris Picciurro, CPA:Yep. Awesome, guys. Well, I appreciate it so much. And everybody that's watching this or listening to this, subscribe to the YouTube channel, check out the content. You're gonna be seeing a lot more from this gentleman over here, Jason, for joining us.
John Tripolsky:And everybody, you have a great, great week. Again, we're coming up on that, that milestone number of our episodes, so we'll we'll pop out some pretty good content and some pretty good, topics for you. So have a great week, like I said, everybody, and we'll see you back here again on the Teaching Tax Flow podcast. See you soon.
Disclosure:The information in this podcast is educational and general in nature. It reflects the opinions of teaching tax flow and does not take into consideration the viewer's personal circumstances. It is not intended to be a substitute for individualized financial, legal, or tax advice. Consult the appropriate qualified professional prior to making any decisions. Securities are offered and supervised through Cabin Securities Inc member, FINRA SIPC.
Disclosure:Investment advisory services are offered and supervised through Cabin Advisors LLC, an SEC registered investment advisor. Chris Picciurro is a registered representative of Cabin Securities and an investment advisor representative with Cabin Advisors LLC, teaching Tax Flow as an independent entity and is not affiliated with Cabin Securities or Cabin Advisors.