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.
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Hey, everybody. Welcome back to the Teaching Tax Full podcast, episode 177. I kind of feel like I need to get my ring announcer voice maybe going on because we're going to talk about Roth versus traditional. However, the voice wouldn't really be too appropriate here because you're not a boxing ring. You're not going toe to toe battling out for who wins. This is more of a team sport, I guess, would probably be the best reference. Right? Not even a relay race because you're not handing it off and the other person's finishing it. I'm trying to think of some cheesy way to explain this, but it's a it's a two person team sport. So we'll leave it at that. Chris Fakuro, I'm gonna let you talk a little bit more about what we're gonna talk about here, but then even more importantly, we have somebody on here that knows more about this, of course, than me, but somebody that you work with a lot.
Chris Picciurro, CPA:Right? Exactly. Well, John, we just had the Olympics finish. As long as you and I aren't in spandex and a bobsled together, I think we're gonna be alright. We'll just avoid that.
Chris Picciurro, CPA:We'll avoid that.
Andrew Charipar:It would be clickbait, but I don't know.
John Tripolsky:It would be more of a harassment than people actually wanting to see, you know
Chris Picciurro, CPA:We're gonna go down that that sled path quick, but we'll probably kill ourselves in in the process.
John Tripolsky:I'll hold the gravity seat. I got you covered, buddy.
Chris Picciurro, CPA:I'm excited about this topic. This is one of the most commonly asked questions from taxpayers. Should I contribute money to a Roth retirement account or traditional retirement account? Roth is gonna be what we call our gold strategy. It's gonna you're not gonna get a deduction today, but the money's gonna grow tax free or tax deferred and the distributions tax free.
Chris Picciurro, CPA:We're a traditional retirement account. Your any contributions in the current year, you're gonna get a deduction for that. It's gonna be pretax, so you get that immediate tax benefit. However, the and the growth is tax deferred, but when you take the money out of the account, it's tax taxable at that time. Now, again, there are different rules as far as nondeductible IRAs and all this other stuff.
Chris Picciurro, CPA:This is this is for 99% of people. That's that's how it works. And remember, the goal is legally and ethically reducing the tax you pay in your lifetime, not just this year. So we are real I'm really excited for Andrew Sharper to visit us, and be a guest on this week's podcast. Him and I, work together a lot in our private practice, and, and he's got a great perspective.
Chris Picciurro, CPA:And and and I obviously, I talk about the tax side of it, but he's a licensed financial adviser. So we're gonna we're gonna bounce things around from the tax part and the financial advising part because a lot of times, as tax professionals, we're really only looking at that one element. So Andrew, first of all, thank you for joining us.
Andrew Charipar:Thanks for having me on, fellas. I appreciate it. I'm pumped to talk about this today. You know, it's something that we You know, when I sit down with a client and we do any sort of financial planning or even before that stage, an introductory question, Hey, should I be contributing to my Roth? Should I be contributing to my IRA?
Andrew Charipar:And I think one of the questions where people might get frustrated at is it depends, right? There's so many variables that go into this. And I think from my perspective, versus a CPA, like you had just had mentioned, where it might be just maybe a little bit more black and white. And we can have all of these things in the vacuum. If we knew exactly what the return was gonna be, we knew exactly what our taxes were gonna be, we knew all of these things, it would be easy to say, Hey, you know, max out your four zero one ks on the pre tax side this year, or, go all in on the Roth this year.
Andrew Charipar:But that's obviously not the case. And what, you know, probably maybe glorifies this profession to me a little bit more, it's a little bit of an art, right? There's a balancing act to some of this. And so I think, you know, for everyone, it's gonna be a little bit different. I think that's why it's nice working with someone like Chris.
Andrew Charipar:And, you know, this isn't a slight on any CPA in particular, but, you know, a lot of the times they're looking backwards, right? And so, with Chris and the team, they're looking forward two, three, four years. So we can kind of take a look at some of these questions and start to tailor them, so that way clients are paying less taxes over time and getting the benefit of compound interest in some of these accounts. So I think depending on what the market's doing is a huge factor in this. It can change the variable a lot.
Andrew Charipar:You know, when the market's at all time highs, you might see, you know, one thing. And when the market's down 30 or 40% in a COVID type situation, you know, the playbook might be reversed there. So it really just depends on everyone's, you know, individual financial situation. But yeah.
Chris Picciurro, CPA:That's awesome. Love that you
John Tripolsky:came right out of the gate and said that it depends. Because Chris says that, you know, we're gonna talk about an episode coming up that even the ideal identical situations, there's no such thing as an easy tax return. So some people might think like, woah. Why do why do people tell me this is frustrated to me? It seems like a cop out, but it's not.
John Tripolsky:Right? I mean, it's it's across everything.
Andrew Charipar:Yeah. I think once you work with enough clients, right, you you see that, you know, this thing exactly. Right? John and Chris might have very similar income profiles, family profiles, write offs, tax situations, but maybe, hey, their personalities are way different, where John is way more conservative, wants to take just, Hey, let's get our four to 6% return. Let's not do anything crazy.
Andrew Charipar:And Chris, say, I wanna push the envelope. I think the market's down 20 or 30%. I may be paying a little bit more taxes on a conversion or putting money into my Roth now, but I know that in three, four, five years, based on historical assumptions of market returns, that there's a pretty good chance, you know, I could squeeze out a little bit more returns putting money into a Roth at this point in time.
Chris Picciurro, CPA:Well, before we jump into that, give us a little bit of his per of family history. I know you're you're from big big 10 country like John and I
John Tripolsky:originally. Originally.
Chris Picciurro, CPA:I I got got out out of of I I went went into into SEC country, but I still wave my or, saw my Michigan State Spartan flag proudly, out on our porch along with our Detroit Tigers. But how did you, yeah, tell us a little bit about your, you know, how you came into financial advising and a little bit about your practice.
Andrew Charipar:So I am from the Eastern Iowa area, Cedar Rapids, kind of a, you know, flyover country traditionally. Born and bred Hawkeye. Never even had a second guess or doubt that I was gonna go to the University of Iowa. Visited zero schools, knew I was gonna go there as a kid. Went there, did my economics degree, and then through just a network of knowing people, actually ended up in town here in the Iowa City area.
Andrew Charipar:I'm at an advising practice. And I originally wanted to I was a little bit more fascinated from the number side of things. I loved putting portfolios together. You know, the classic, you get maybe some money that you put together from bartending over the weekend in college. You you open up a Charles Schwab account and think you're gonna retire in the next two years by betting on a bunch of options.
Andrew Charipar:You know, I think maybe a decent chunk of us have been there, done that. A lot of us end up maybe becoming a little bit more realistic with options, and and and and that sparks an interest in this field. So I wanted to come into that side of things. I started at a small RIA here. You know, in this world, you know, 150, 200,000,000 is pretty small.
Andrew Charipar:You know, they would probably call it boutique to make it sound a little bit fancier. But, you know, in these smaller firms, you get a chance to cut your teeth on everything. So, I quickly realized that I really, really enjoyed the people side of things as well. And in this field, you can kind of wrap all of those things into one. So, helping clients put a portfolio together, trade, do some of the financial planning, some of the estate planning, tax planning, and then obviously the advising thing, too.
Andrew Charipar:Helping families walk through tough situations where, Hey, my spouse died. You know, what are these things that I need to do? I don't know how to, you know, I don't know anything about, What's a ten ninety nine? So, think this field changes all the time with the market. You see all sorts of different complex problems.
Andrew Charipar:And at the end of the day, it's fun to sit down with people. While we're obviously sitting here virtually, you know, one of my favorite things about this is getting to sit down and kinda connect with people in person. The Zoom stuff is growing on me quite a bit, but, you know, fortunately, been super blessed between the clients here and the clients that I've partnered up with Chris on. Just super great people that make you feel good about what you do, and it's just it's a true pleasure and true passion.
Chris Picciurro, CPA:Well, thanks for sharing that, and we're gonna you know, I wanted to mention this direction, should mention this in the opening. We are aware that there are a lot of rules. Like, there's there's rule there's phase outs on can you contribute pretax to an IRA and how much you could do in your employer plan. This episode's not about the rules. We're assuming that we're making contributions within the rules.
Chris Picciurro, CPA:What the why we wanted to have someone like Andrew on is that we wanted to walk through what should be going through your mind in in different seasons of your life. So I'm gonna start. So, Angel, let's say you start working with with taxpayers in their twenties, which would be great if someone took the time to meet with a financial adviser in their twenties. What are some of the things that you're talking to them about when it comes to traditional versus Roth? Because yeah.
Chris Picciurro, CPA:I mean, they have they have, in theory, a long road ahead of them.
Andrew Charipar:Yeah. Again, it's going start with one of those things as it depends. When I sit down with someone, the first thing is, Hey, are you working as a W-two? Do you have an employer that's matching? If you're not contributing to your plan and at least getting the match, whether it's pretax or the Roth side things, please take that free money.
Andrew Charipar:Please, please, please. Usually, the second question's going to be, What's the income like? What's your spouse making? Is it just a single person? Do you have kids?
Andrew Charipar:What's the tax situation? For people that are earning a lot of money early on, we've got some people that might be a software engineer making mid 6 figures in their mid to late 20s. It makes a whole lot of sense if you're going to be in a 12 or 15 or 20% bracket twenty, thirty years from now, to take the advantage of maybe if you're in that 37% bracket now, getting that right off there. I think that's a huge, huge thing. On the other side of things, hey, if you're sitting here in the 12 or 22% bracket, you've got a long runway, you're probably just going to build a really nice nest egg over time, you can afford, it's not going to make a massive difference on taxes, you might want to take the Roth route.
Andrew Charipar:I think one of the things, and I'm not a gambling man, but I would wager that taxes are probably gonna go up over the course of the next ten, fifteen, twenty years. So, I think a lot of people see that and say, Hey, it might not make the most sense today. I might be able to squeeze a couple percentage points off, putting it in the pretax versus the after tax. But if I look twenty years from now and taxes are eight or 10% higher, and I've been growing, compounding for free, tax free at that time period, it might make a whole lot more sense to do that. And I think a lot of younger people specifically, maybe even some of the higher income earners there, are starting to realize that.
Andrew Charipar:And I think everyone that's older, right, has already realized that that but it might be a little bit too late or that those things weren't as as readily available twenty, thirty, forty years ago.
Chris Picciurro, CPA:Right. I mean, someone that's, let's say, in their late twenties and we is a tech exec tech they don't even need to be a tech executive. They could be someone that just kinda got in, has a bunch of stock in the in the company. Or let's say they are a thriving entrepreneur. Or let's say they're a child actor or or they, you know, they're they're make tons of money in their twenties.
Chris Picciurro, CPA:There's a difference between as you hit the nail on the head talking about is are you gonna be an actor, like, for the next twenty, thirty years? Is your income gonna be high? Or are you gonna be one of these actors that makes a boatload of money, pockets it, and then basically goes and lives a normal life and doesn't have a lot of active income in the future? Because if if that's the case, the pretax makes a little more sense than the Roth. But if your income's gonna continue to grow and you expect to be in that higher marginal tax rate in the future, and then you also have to think about state tax too.
Chris Picciurro, CPA:Right? Because by little actor people might be in New York or California versus, the beautiful state of Tennessee. So we, you know, we've gotta think about that.
John Tripolsky:And, Chris, a good example of that too, you know, would probably be I'm taking NIL or any of that stuff, but, like, some sports. Right? Like, you have some guys getting into this early twenties, and the average professional career might only be four, six, eight years, ten if you're a dinosaur in some some sports. Right? So, like, that's that happens more often than not.
John Tripolsky:Right?
Chris Picciurro, CPA:Yeah. Yeah. Professional. Yeah. So anyone that your peak earning years are in earlier earlier than normal, you may have like Andrew says, it depends.
Chris Picciurro, CPA:Different considerations. So so then and so let's talk about someone in their thirties as they as they move into that decade. This is the decade from a tax perspective. Again, everyone's different, but this is the decade of change typically. You know?
Chris Picciurro, CPA:Your marital status might change. You might start having a family. You might start getting more serious about your career. You you could you might look into home ownership and start truly adulting, if that makes sense. What are some of the things someone in that age should I know it all depends, but should consider differently because, you know, they're ten years older than they were in their mid twenties.
Chris Picciurro, CPA:Now they're in their mid thirties.
Andrew Charipar:Absolutely. And this is something huge. Right? Know, I think that's one of the big positives of just flexible financial planning in general. Life changes, whether it's you're getting married, you're having kids, you're getting divorced, someone dies, things that aren't as fun to talk about, but it certainly changes the picture there.
Andrew Charipar:I think a lot of people, and it probably falls in a couple distinct crowds. One of the ones that I mentioned earlier, and you're kind of seeing this in news recently, with this software engineering, everyone's worried that AI is gonna take their jobs, they've got these really nice incomes, they're worried that, Hey, five or ten years from now, I may either have to completely transition to something else, or my income may be substantially reduced. And so that's a conversation piece there. I think the big thing as well is, if you've got two people that have been doing the right thing, they've been saving a bunch in their early 20s, they make good income, they finally get together. They maybe want a little bit more liquidity, and they've put a bunch away early on.
Andrew Charipar:They know they've got, at least for now, somewhat stable careers, and maybe they want to maybe just contribute just a little bit. They're not as worried about that. They wanna build up some funds for kids. Maybe they want to take a step back from work and not make as much. Or they realize that, Hey, over the next ten, twenty years, I'm going to keep working super hard, building my firm.
Andrew Charipar:My income's going to continue to grow. That's going to be the expectation that this is gonna be a little bit of a longer term thing. But again, I think for each person, it's gonna depend on year to year. I think the other crowd is gonna be kind of the commission crowd. I've got people that might make absurd, like you're the athlete thing.
Andrew Charipar:They might make absurd amount of money in one year, and then the next year, might be flat, right? Some of these farm clients that I have out here in the flyover country, their income just varies so much year to year. And so this is something that I think at the beginning of the year, everyone should kinda sit down, take a look at, maybe do You don't need to know exactly what your income is gonna be for the year, but if you have a pretty good idea, we can start to make some assumptions. Then I think sitting down with a Chris, whoever your financial advisor is, having a quick conversation and touching base on that. And then I think touching base towards the end of the year again, Hey, how much income has come in this year?
Andrew Charipar:Where are we at? What does it look like for the next couple of years? Just that ongoing planning is gonna make a huge, huge difference in really kind of helping put money into these separate buckets as time goes on. And I think, and this may be not even a topic for this episode, right? But I think one thing we're seeing as well is, Hey, I've maybe maxed out my four zero one ks from the year, whether that's traditional or post tax in your Roth, but maybe we're retiring early.
Andrew Charipar:Maybe we want to build up a joint brokerage account. That way, we have some flexibility if one of us wants to retire or we want to invest into some real estate. So, I think all of these things start to tie in. Again, that's why that it depends is actually a real thing because there's just so many variables that go into this. Mentioning the actual market itself and what's going on there.
Chris Picciurro, CPA:Well, in an and I'm I'm typically pro Roth, but an argument to to the pretax account is this. Assuming you're in a high marginal tax rate, you can always convert from your traditional to Roth in a low income year, but you can't can necessarily go the other way. So, gosh, it's tough, you know, sometimes. And and we see that especially for clients like you're mentioning the farm clients, clients that are self employed. I mean, you you could easily have someone that that owns a towing company.
Chris Picciurro, CPA:Okay? And let's say they make a good living, a $150,000 a year. They're self employed. Let's say they don't even have any employees, but every four years, they need to buy a new truck. That truck's gonna be a $180.
Chris Picciurro, CPA:Right? That year that they buy the truck, they're gonna give a huge depreciation deduction, and that's the year they might wanna convert all their pretax money to a Roth. But in the active years, where they're $150 of income, they're hammering a solo k or a or a sap and then convert it into a low year. But that's that that doesn't matter what age you are. That's just planning one zero one.
Chris Picciurro, CPA:You know? So so someone moves out of their thirties into their forties. This is the year these are the this is the decade from a tax perspective where it's a decade of distraction. You you have your children could be getting older. They could be getting close to college depending on when you started your family.
Chris Picciurro, CPA:But you also when I say distracted, they're they could be playing different sports or being involved in other activities. And a lot of times, though, at that age, your parents start needing you a little more. Maybe not just financially, but maybe just being there for them. Maybe they don't if you don't live in the same same town like me, maybe they it's harder for them to travel to see you, and you you need to be more and more flexible and go see them, which is which is an expense, especially when you have a large family. So how does that change thirties to forties from you know?
Chris Picciurro, CPA:Because now you have also, have less time you know, your less time before in in thirty year to retire.
Andrew Charipar:Yeah. I think you hit the nail on the head there. I think that's, like, one of the big inflection points other than maybe right before retirement, those last three or four years where people are like, Oh crap, either I prepared a bunch or I didn't prepare, and what do I need to do to catch up over the last ten or fifteen years? So, as people progress into your 40s, you're right. I think everything should be at that point.
Andrew Charipar:If you've been prudent, you've sat down, you've got a CPA, you've got a financial advisor, things are on coast. You're really usually, for most people, starting to ramp income, right? Those are those years that you're seeing income usually explode maybe into the early 50s until you start to see that kind of wind down. Again, it just depends on businesses and people's careers, but I would say on average, that's typically that time where you really start to see income explode. So we typically see people really maxing out.
Andrew Charipar:A, they've got the liquidity, right? To just max out those 401s, the solo 401s. If your income's again that high, we're typically seeing people continue to load money into the pre tax side of things. And then that spark goes off, right? We start talking about the after tax benefits, or, Hey, in five or ten years, maybe we want to start building out a Roth conversion ladder if you're going to retire early.
Andrew Charipar:That's a tax strategy that we can implement. Or just straight up getting tax dollars into that bucket from there. Or, again, I'll kind of defer to this as well. People are saying, Hey, I've got a really beefed up 04/2001. Things are great.
Andrew Charipar:Job's secure. Maybe at this point, we're looking at retiring early or diversifying or taking a step back. Liquidity wise, maybe we max those things out, or maybe we pause for a year or two, or at least get the match, and we put some money into a brokerage account. And that way, it gives us a little bit of flexibility with things going forward. But I think as people in those accounts start to grow, you start to see And I preach with clients all the time, in returns and in portfolios, let's focus on percentages.
Andrew Charipar:At that point in time, you're starting to see those portfolios where a 15% swing in the market is no longer maybe a couple grand. It's starting to become annual salaries, right? So people really start to see that compounding take effect. And when you can talk about, Hey, this thing's gonna compound for another ten or fifteen years. In a perfect world, historically speaking, we might double another one or two times that portfolio.
Andrew Charipar:If that's tax free, you're looking at quite a few dollars saved over the course of the next decade or two. And so I think at that point, people are starting to have these really in-depth, more hands on things that you're doing, we're doing, tax conversations on really trying to put the pieces together and plan plan for the next, you know, the next decade the best we can given the information we have now.
Chris Picciurro, CPA:But the last the last group I wanna talk about is gonna be 50 and older, but we've got two little two buckets. Right? Because there the sixties is tough to say because, really, I look at it like this. When do you go I don't know if I'm ever gonna retire because I I love something, but kinda I look at it like when that pre taking Social Security and that post taking Social Security time. Obviously, after taking so you know, drawing Social Security is on until unless you have earned income, you can't contribute to the Roth versus traditional.
Chris Picciurro, CPA:But what are some of those things that are we're thinking about post 50, we'll say? Let's just put them in all all in one category. Instance, yeah, I'm in that category now, but I'm getting down proud of it that I made it this far. But but from the IRS perspective, that's when you could do catch up contributions and that sort of thing.
Andrew Charipar:Yeah. Again, I I think if you can you know, in in any world, right, from a financial adviser perspective, from, you know, planner perspective, you know, if you can put that money away and you're not gonna be spending it, it's not gonna be a liquidity crudge, put that money away. You can always take that stuff out later. Obviously, there's penalties and things like that involved if you're gonna take it before 59 and whatnot. But I think as people transgress into that age, again, this is gonna fall heavily on planning.
Andrew Charipar:If you don't have enough saved, you need to make sure. At that point, it's not about return, right? When you're in your 50s, and you're trying to play catch up, and you haven't put as much away as you would've liked, it's not about return. It's about putting those dollars away and getting that money saved. So I think that's one of the big things maybe in one crowd.
Andrew Charipar:I think the other thing there, especially if people are maybe taking their foot off the gas pedal, right? Income might be coming down, you're in your late 50s. Hey, you're in the 12% bracket or 22. Maybe let's either contribute to the Roth, or maybe we can start talking about maybe doing some Roth conversions, and maybe taking and moving money from the pre tax bucket to the post tax bucket. But I think for a lot of people, just continuing to hammer, if you're getting a match, please, please, please take advantage of that.
Andrew Charipar:I think everyone that's probably listened to this is, right, there. But as people get later on, if income's falling, they're probably putting money into the Roth brackets. If they're continuing to pump up that income, income's still really high in those 32, 37% brackets, probably on average still just maxing out what they can in those before they either quit working or they transition to another phase of life
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John Tripolsky:Sitting from my perspective, right, I think the coolest thing is is just watching your conversation kind of volley back and forth. Right? Like, Chris, it seems like I know, Andrew, you mentioned early on. It it's great working with a tax professional that has the foresight or or not just the knowledge, but the the I wouldn't say the guts either. I'd I'm looking for the best term here, but, like, that's how they they run their practice and their their way of doing it.
John Tripolsky:Right? And then, Andrew, I think it's great too. Like, what you were saying, and you said it multiple times. Right? Kinda solidifying that relationship between, you know, not only those two professionals like yourself and Chris, but just people's perspective of things as the taxpayer, as the, you know, the person that's moving along.
John Tripolsky:And I do like how you guys Chris, I think you might have started off that way, chunking it out into, you know, phases of life because everybody can really relate to that. Even if it's not exact, it kinda gets the point across. Right? So it was cool to watch you guys do that. So if anybody thought they were gonna battle it out, sorry, sorry to disappoint.
John Tripolsky:There were no gloves. There was no bloodshed. And, yeah, it was a pretty good conversation. So I appreciate it.
Chris Picciurro, CPA:Well, no. I appreciate Andrew coming on. I know we're gonna have some more content, and I I think that that the most important thing to understand is there there isn't a perfect answer. It is it depends, and you could contribute to a Roth and traditional together. They complement each other based on your situation.
John Tripolsky:100%. 100%. I'll close with this before I let everybody go. Think about this what we've talked about, like building a house. Right?
John Tripolsky:And and imagine your architect never talked or never understood what the guy who's framing it up or, you know, pouring concrete before the framing goes in, your plumber, your electricians, all this stuff. If they didn't talk to each other or even if they thought they could one person can do it all, you're gonna end up with a different result at the end. Right? I mean, down to somebody playing how you're gonna use this house. You know, you might think you need laundry in the basement because it's out of the way, but you don't realize in ten years, you're not gonna wanna go up and down the stairs anymore, so you need it in the war.
John Tripolsky:Little things like that, I think, really, again, solidifies is probably the best word I can use here, but solidifies the value of that relationship, you know, your personal board of directors as we talk about. So people working together, understanding and respecting each other, frankly. So we'll keep this train going. Some great topics. I know we're gonna dive a little bit, little teaser for the upcoming episodes.
John Tripolsky:We're gonna start diving into that defeating taxes book a little bit, pulling some content out of that and discussing it kind of chapter by chapter. So, Andrew, we look forward to having you back, man. Thanks for joining
Andrew Charipar:I appreciate it, fellas. Thank you for all your work you do. And yeah, I just read it what you said. I think having these people on your team doing that work, it's small little conversations over the course of the year. Let the professionals flex their expertise, save you money over time, make the right decisions, and, know, go do what you do on a regular basis.
Andrew Charipar:But, yeah, appreciate the time and looking forward to future content.
John Tripolsky:Awesome. We are absolutely pulling that for real for social media. Flex your expertise. So you can do a mic drop there, buddy, and we will talk to you soon. Everybody who's listening in, have a great week.
John Tripolsky:We'll see you back here again on the teaching tax flow podcast.
Disclaimer: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.
Disclaimer:Investment advisory services are offered and supervised through Cabin Advisors LLC, an SEC registered investment adviser. Chris Picuro is a registered representative of Cabin Securities and an investment adviser representative with Cabin Advisors LLC, Teaching Tax Flow is an independent entity and is not affiliated with Cabin Securities or Cabin Advisors.