#49 - Reflections & Revelations: A Look Back at our Favorite Episodes to Date

[00:00:00] You do the cost segregation, you get the bonus depreciation from year one. All of the furniture

[00:00:04] that you're buying and all of those expenses that you're putting into the house can go directly to

[00:00:08] offset your W2. So we've seen a number of pilots here at Hawaiian take advantage of that strategy

[00:00:13] this year after hearing about it on the podcast and it's a really great strategy.

[00:00:17] You know, interest rates are super, super high. Like what do you do? How do you pivot?

[00:00:20] What strategies can you partake in to actually take advantage of this high interest rate

[00:00:25] environment that may be clouding maybe your ability to buy a house or you know sell and

[00:00:29] you know, whatever it might be, right? You want to make sure that you're taking advantage of this market.

[00:00:44] Welcome to Passive Income Pilots where pilots upgrade their money. This is the definitive source

[00:00:51] for personal finance and investment tactics for aviators. We interview world-renowned experts

[00:00:57] and share these lessons with the flying community. So if you're ready for practical

[00:01:01] knowledge and insights, let's roll. Hey, welcome back to Passive Income Pilots everyone to the

[00:01:06] 49th episode. What are we nine-ish months into this podcast? Ryan Gibson, how you doing my friend?

[00:01:15] I'm doing great and I'm excited to almost be at our 50th. We actually have an amazing guest

[00:01:20] planned for our 50th episode so we'll be releasing that one shortly but you know today

[00:01:25] I really wanted to have a conversation with you Tate about why we started this podcast,

[00:01:30] you know as we round the corner on nearly 50 episodes and what our goals are here to

[00:01:36] provide the flying community and the investing community at large. Absolutely.

[00:01:39] And some of the feedback we've gotten, I think we can share some of that and then just kind of

[00:01:42] recapping some of the major themes that have come out of this podcast that I think our

[00:01:47] listeners will really appreciate. Yeah, I'd like to go back highlight a few of the things that

[00:01:53] we've gotten to explore on the show and point some of the newer listeners back through

[00:02:00] some older episodes where we brought on some incredible guests and give them a chance to

[00:02:06] just pull some highlights out and maybe point you in the right direction if you'd like to go back

[00:02:10] and listen to some of the older episodes because just because they were a little bit older doesn't

[00:02:14] mean they lack any substance or value. So Ryan, you want to kick us off? Yeah before we do that

[00:02:20] I actually wanted to just kind of remind everybody what the philosophy of this show is all about.

[00:02:25] You know Tate and I have established submission vision values through the podcast

[00:02:29] and one of the things that we want to make sure the listeners know about is we're not here

[00:02:33] with a singular focus. You know, a lot of times you talk to a financial advisor or you talk to

[00:02:38] someone who's trying to get you to sign up for their program or sell you some insurance

[00:02:44] or something like that they have what's called a singular focus. This podcast is not intended

[00:02:48] to do that. This podcast is intended to bring the best and the brightest from the aviation

[00:02:53] community and the investing world and sometimes both they have both flying in and investing

[00:02:59] in their background to the podcast to open up everybody's awareness of all the things that

[00:03:05] happen in the investing world so that they can make great decisions on where they decide to put

[00:03:10] their money. We're not providing any tax-legal or investment advice on the show. However,

[00:03:14] we are trying to bring in guests that can provide a more comprehensive look at the

[00:03:19] market. Stocks, bonds, mutual funds, traditional, non-traditional, alternative investing, syndications,

[00:03:26] going out and doing your own projects. We're trying to bring you all that information

[00:03:31] into one spot because that currently doesn't exist. Absolutely. Then most importantly,

[00:03:35] we're trying to make it actionable. We're trying to say, hey, here's the best vendor

[00:03:39] or here's someone you can go talk to about getting this tax or legal or investment advice

[00:03:44] and here's their opinions on a certain topic. We're really excited to continue building this

[00:03:50] brand and building this podcast so that all of our listeners can say, hey, I can go to passive

[00:03:55] income pilots and find any part of the industry that I'm looking for in a safe environment that

[00:04:01] isn't going to be totally biased to trying to sell you one particular thing.

[00:04:06] Having said that, me and Tate are raising your own money and doing your own funds

[00:04:10] and things like that. But the point of this show is to bring everybody together and have a really

[00:04:16] comprehensive look at the financial environment and just in to show what's out there.

[00:04:21] Absolutely. We are going to do a recap today of some of our big takeaways, big topics that we've

[00:04:26] talked about. If you've just tuned in and you've never listened to an episode, this is the perfect

[00:04:31] place to start because you can get a taste of everything that you've missed in the previous

[00:04:35] 50 episodes. Now that it isn't worthwhile to go back and listen to those, but we're going to

[00:04:40] give you the episode number and say, hey, this is the topic we talked about. Here's a quick overview

[00:04:45] summary. Tate, kick us off. Yeah, I'm going to take us back to episode number 10 with Toby Mathis.

[00:04:50] This actually was the number one downloaded episode. If we look at our stats, that one is

[00:04:56] through the roof. Everybody is looking for ways to mitigate their taxes.

[00:05:01] Episode 10 is reduce your taxes and minimize returns using proven investment strategies

[00:05:06] with Toby Mathis. Toby gave us a 15 minute MBA course on active, passive and portfolio income.

[00:05:15] It's just an incredible episode. I point people back to that one every time. He touches on real

[00:05:20] estate professional status and depreciation, how depreciation works in real estate. Really

[00:05:25] important if you're trying to wrap your head around real estate. There's a reason why we

[00:05:30] are real estate enthusiasts. We don't want to be biased on this show. We want to provide the full

[00:05:37] landscape and let people see what all the options are and be open to every investing strategy out

[00:05:43] there. But there's a reason why Toby is a big fan of real estate as a tax strategist, as a tax

[00:05:47] attorney, and the reason why Ryan and I are such fans of real estate. Ryan, you want to

[00:05:52] touch on that episode because I know you've been working with Toby and Clint at Anderson

[00:05:57] Advisors for a long time and not necessarily promoting them in any way. We don't necessarily

[00:06:04] promote anybody that we bring on the show, but I know you have a relationship with them

[00:06:07] and you might have some takeaways from that show. Yeah. I mean, I would say that every

[00:06:11] pilot out there is trying to figure out how to reduce their taxes and mitigate their risk.

[00:06:16] What a better place to talk to than an attorney that specializes in tax and legal

[00:06:21] strategy. And so we've had these guests on the show that can talk about how to

[00:06:25] mitigate your tax and your legal strategies. And sometimes, as pilots or as high paid professionals,

[00:06:32] there's not a lot of options to reduce your taxes. And if you've started to invest,

[00:06:36] you're kind of wondering, do I need an LLC? Do I need a protection against this asset if I have

[00:06:42] one rental property that I'm using as an Airbnb or running out long term? Or what ways can a

[00:06:48] pilot minimize or reduce their taxes? And so that episode really dives into how you can

[00:06:55] change your facts to adjust your tax, to fix some of your tax strategies where you may be thinking,

[00:07:02] okay, I'm paying through the nose on my taxes. I'm making $300,000 this year for the first

[00:07:07] time ever because my contract and I'm getting a bonus and all this, what can I do to better

[00:07:12] position myself for tax strategies? And so that episode really dives into that.

[00:07:18] I'll take it a layer down and say that if you do decide, hey, to go buy some real estate,

[00:07:23] there are some things you can do like depreciation. And there's a whole episode on that.

[00:07:27] Hey, what number is that? Well, I'll mention that episode 14 was a follow up with Toby and we talked

[00:07:33] about cost segregation and tax savings. But then to go a layer deeper as you're alluding to,

[00:07:38] we then did an episode with Yona Weiss, who is with Madison Spec. And that is episode,

[00:07:46] I'll get the number for you in a second, you break down that episode for us. And that's

[00:07:51] a really good point. Episode 14 is a follow up to some of the more granular tax strategies

[00:07:56] that we can do. So if you listen to the number 10, you're going to learn kind of a high level and

[00:08:02] then 14's a little bit deeper. And then what episode do you have for us on Yona? 32. Episode 32.

[00:08:08] So that even goes a layer down. We only just glaze over depreciation. But Yona actually lays

[00:08:14] it all out and says this is exactly how to do it. And by the way, I actually use Yona

[00:08:20] for all my cost segregation studies. At least I did when we hired it externally. Now we do them all

[00:08:24] in-house, long story short, but we're able to do it in-house. But I did all of them probably over

[00:08:29] 25 cost segregation studies with Yona. And if I was going to go external again, that's the guy

[00:08:34] who I'd use. Give him a call. If you've heard about our Reno Airbnb, he was the one that

[00:08:39] did the cost tag on that. Yeah. So if you're wondering like, hey, I bought a bunch of rentals

[00:08:43] or I'm about to buy a bunch of rentals and I want to make sure that I'm best positioned

[00:08:46] and most tax-efficient on those, that episode is going to save you tens of hundreds of thousands of

[00:08:52] dollars in taxes. So make sure you give episode 32 a look. The next thing I wanted to bring up

[00:08:59] is IRA investing. We've talked about this on the show. Maybe you're at a regional airline

[00:09:05] and you switched to a major and you are like, what do I do with my 401k? What do I do with my

[00:09:11] IRA or hey, Tate, I really want to invest in your project, but I want to do it with my

[00:09:15] retirement account. Can I? And the reality is, when you think about your fidelity or Schwab or Tiro,

[00:09:21] whatever a custodian is housing your airlines 401k, you can't use that to invest in anything

[00:09:27] other than stockpons mutual funds. You can't take that and go buy your own rental property.

[00:09:32] You can't take your retirement account and go buy your own Airbnb. You can't take that and

[00:09:37] go invest in a syndication. You can't use it to go flip houses. However, you can use a

[00:09:41] self-directed IRA to do that. And so we decided, hey, let's record an entire episode and introduce you

[00:09:48] to somebody who or really I should say a company since Derek unfortunately has moved on from Quest,

[00:09:53] but there's a guy Kirk Power, you can call now at Quest Trust Company to talk all about

[00:09:59] self-directed IRAs. We also brought on Kerry Cook who's the CEO of Preferred Trust Company.

[00:10:05] And so we have two episodes that actually dive into how to do all this retirement stuff. So if you're

[00:10:11] thinking, again, hey, I want to use my retirement account to be an investor, we've got a whole show

[00:10:17] on that. And so what number is that? So Kerry Cook preferred Trust Company is Episode 9 and

[00:10:23] with Derek Long at Quest is Episode 36. I think the Episode 36, I have to say, Derek laid

[00:10:30] down the best explanation of true self-directed IRAs I've ever heard. So Episode 36, I think is the

[00:10:36] place you want to go. There are dozens of self-directed IRA companies out there and to be

[00:10:41] clear, in order to invest in non-public market investment opportunities through a retirement

[00:10:49] account, you have to be with a fee based self-directed. And I know there's a self-directed

[00:10:55] retirement account within Schwab that's not a true self-directed. It's a shame that they use

[00:11:00] the same verbiage. But there are dozens of those companies, Preferred Trust and Quest are the

[00:11:05] two that we work with most often. So you have a chance to get to know those people right here on

[00:11:09] the show. Okay, I'm going to call on audible and talk about all the year end tax tips

[00:11:15] that somebody may need or may want to listen to. So every year, guys, guess what? You're

[00:11:20] going to have this tax thing and you have to have a bunch of stuff in by December 31st.

[00:11:25] So if you're thinking, okay, well I got to remember this episode for next year, maybe

[00:11:29] copy and paste this link to re-listen at the end of the year. But we do have a end of the year

[00:11:34] tax tip episode where we literally go through all my favorite strategies on what you need to

[00:11:41] do at the end of the year to save money on taxes. So we had a complete episode on that.

[00:11:47] And I'll go through the highlights of that episode super fast. But number one,

[00:11:52] how to do a Roth conversion or I should say, yeah, a Roth conversion at the end of the year. So

[00:11:57] you may be exceeding the income limits for your retirement account contributions to a Roth.

[00:12:02] I think the limits are like 160 grand or something like that this year.

[00:12:05] That's very low. Yeah, very low. But so again, you're that guy making $250,

[00:12:10] $300 this year with United or Southwest or Delta or Lions or Alaskans new pilot contracts. And so

[00:12:17] now you're in that higher income bracket, right? And so you're saying, hey, I need to make contributions

[00:12:23] but I don't want to be in traditional IRA, but I want it to be a Roth but I can't put it in the

[00:12:28] Roth. So I'm going to put in the traditional and then I'm going to backdoor it into a Roth.

[00:12:31] And then to add it on to that, there's a way to actually save or reduce the amount of money

[00:12:36] that you're taxed on with that conversion. Because remember, when you convert, you actually pay the

[00:12:40] taxes on what you convert because a Roth, you have to pay the taxes before it goes in, right? But

[00:12:45] then it grows tax-free. There's some really awesome strategies and how you can get

[00:12:49] your assets revalued and then save a ton on your taxes. So check that episode out.

[00:12:55] That episode is with who and what was the number? That was number 44,

[00:13:02] mastering your end-tax strategies with yours truly, Tayden Ryan.

[00:13:06] Nice, I love it. Okay, Tate, you have been on a journey. I mean, half these episodes,

[00:13:11] I feel like you're at a U-Haul truck. And it's because you dove in, you've taken massive action

[00:13:18] and you've gone out to Reno, Nevada and you bought an Airbnb because you wanted to pick

[00:13:23] up some huge tax savings and buy an awesome house. What's it called? It's called the

[00:13:27] crib or something like that, right? Or the stoke house.

[00:13:35] We did buy a crib as an amenity but I couldn't buy it on Amazon because I didn't want to

[00:13:42] mess up my algorithm and get huggy dads for the next six months. So yeah, I had to go into a store

[00:13:48] and pay cash now. I'm just kidding. We called that a pack-and-play for those parents out there.

[00:13:53] And we appreciate you putting that in your Airbnb take because the pack-and-plays are always

[00:13:57] a pain to move around. So thanks for putting that as an amenity in your Airbnb.

[00:14:00] Yeah, so the short-term rental loophole is something that's getting a lot of attention lately,

[00:14:06] particularly on social media, among the tax strategy crowd. And it's because the depreciation

[00:14:13] that you can pull out of real estate is super powerful but most people can't use it against

[00:14:18] their W2 income. In order to use it against your W2 income, you have to be a real estate

[00:14:23] professional. And that's a whole thing that we dive into on multiple episodes with Toby Mathis.

[00:14:30] We dive into it as well on episode 42 with Billy Withers, who's a tax strategist.

[00:14:34] And so real estate professional is the holy grail. If you can get that, then you can use all

[00:14:40] of your syndication losses, all of your long-term rental losses against your W2.

[00:14:45] But if you cannot climb that mountain because it's a mountain, it's a quite a bit of paperwork

[00:14:51] that you have to log your hours, you have to spend a lot of time managing your own rental portfolio

[00:14:58] in order to qualify as a real estate professional. If you can't get that status, it's not the end

[00:15:03] of the world because if you own an Airbnb and you actively manage it yourself and as long as

[00:15:09] the average stay is less than seven days, you can take those depreciation losses from

[00:15:14] that particular real estate asset against your active income. So we're seeing an uptick in

[00:15:20] doctors, attorneys, pilots, high-paid W2 professionals jumped into the Airbnb space because they can run

[00:15:27] a cost segregation study on the house. They can write off all the furniture that they're buying

[00:15:31] and they can apply bonus depreciation last year is 80%, this year it's 60%. It's starting to phase

[00:15:36] out but it's still a very accretive tax benefit. And by putting it into service doesn't necessarily

[00:15:42] have to rent, but it has to be advertised. It has to be live on Airbnb prior to December 31st

[00:15:50] and you can take all of those tax benefits from buying it, you do the cost segregation,

[00:15:54] you get the bonus depreciation from year one. All of the furniture that you're buying and all of

[00:15:59] those expenses that you're putting into the house can go directly to offset your W2. So

[00:16:03] we've seen a number of pilots here at Hawaiian take advantage of that strategy this year after

[00:16:08] hearing about it on the podcast and it's a really great strategy. So if you want to

[00:16:13] learn about the loophole go to episode 42 with Billy Withers episodes with Toby Mathis.

[00:16:21] And if you want to learn about Airbnb's themselves, we had a great episode with Dan Templin that was

[00:16:27] episode 41 diving into sort of the nuts and bolts of how to find, renovate and run Airbnb's.

[00:16:35] That's great to say it. And I also, I don't want to miss a good topic but I mean we've

[00:16:39] done everything on this episode from episode two talking about opportunity zones and DST funds and

[00:16:44] how to do 1031 exchanges. Two, if you want to hire a wealth manager in episode number three,

[00:16:50] we talked about wealth management strategies, how people get paid, your financial advisors.

[00:16:56] We talked about an episode six transitioning from active to passive investing with Jeremy

[00:17:01] Roll who's done over 100 syndications. We talked about blockchain. We talked about

[00:17:07] doing investing in crypto that was on episode eight. That was like the best explanation of crypto

[00:17:14] and blockchain that I think I've ever heard, which is super awesome. We've talked about this

[00:17:20] high interest rate environment that we're in, right? Where we're actually, interest rates are

[00:17:24] super, super high. Like what do you do? How do you pivot? What strategies can you partake

[00:17:29] in to actually take advantage of this high interest rate environment that may be

[00:17:33] plouting maybe your ability to buy a house or sell and whatever it might be, right? You want to make

[00:17:38] sure that you're taking advantage of this market. That was episode 11. We talked about investing in

[00:17:44] laundry mats, an episode 13 super fun with our friend Sam Wilson. And I really want to

[00:17:52] talk about the storage industry, right? Because the storage industry is something

[00:17:56] that I'm super involved in. Tate, you've invested millions of dollars with your fund

[00:18:00] into self storage, many millions into self storage. And we've done things where we dive into

[00:18:07] what self storage is all about, how we evaluate deals. We talked about how we find and locate

[00:18:13] those properties to actually build ground up. We even had a general contractor come on who built

[00:18:18] self storage. Aaron Saunders, our president of construction to talk about that. I believe he

[00:18:22] did that in episode. Well, the one where we do a little bit of a deep dive into self storage

[00:18:28] is 43. And Aaron Saunders, boy, if you want a deep dive into the construction aspect of self storage,

[00:18:35] what episode is it with Spartan Construction Management? 27. All right, 27 with Aaron Saunders.

[00:18:41] So with that, we just wanted to make sure that we had an opportunity to

[00:18:46] kind of just lay the land, kind of reinvigorate the reason why we're in this podcasting space

[00:18:54] and what's to come with passive income pilots. There's actually a lot of things that we're

[00:18:57] going to be doing this year. Yeah, let's look to the future. So we've recapped, right? So what's new?

[00:19:03] What are we, where are we going with this thing? Yeah, before we do that too, I do want to say

[00:19:07] episode 46, oil and natural gas investing. By the way, we've scraped the surface of the earth for

[00:19:14] years, I feel like, to find somebody who actually knows what they're talking about.

[00:19:17] Well, and we're going to go deeper on that. I've actually got some guests in my pocket

[00:19:22] that are coming. If you just want to layman's explanation of it, episode 46, Derek Long comes on

[00:19:28] from Eckerd and he talks about how to do oil and natural gas investing. Amazing. I've never heard

[00:19:34] it explained so clearly to me. And that's where I think, Tay, you talk about the future,

[00:19:39] I think what's really, for me, what I'm very passionate about on this show,

[00:19:43] especially is simplifying this stuff because I don't have a big Wall Street back around.

[00:19:47] I didn't have a ton of financial experience previously as an airline pilot. And so we're

[00:19:53] trying to get the people that can help us learn all this stuff together. So, Tay, why don't you talk

[00:19:58] about a little bit more about what our listeners can expect in the next 50 episodes or the next

[00:20:02] 100 episodes for that matter? Yeah, I'm really excited about the next 50 to 100. The next

[00:20:08] years of doing this podcast with you, Ryan, we're just getting started. We're going to bring

[00:20:13] on some incredible guests. We've got a really exciting guest on episode 50 in-store for you,

[00:20:18] so stay tuned for that. We're going to bring on guests that you've never heard of.

[00:20:23] We're going to talk about asset classes that you've never even thought of and investing

[00:20:26] strategies that you've never even thought of. And overall, we're going to provide

[00:20:32] the most unbiased and holistic platform for investing education for the pilot community

[00:20:39] that exists. So thanks, everybody, for being loyal listeners and we'll catch you on the next episode.