PILOT’S PORTFOLIO: WHAT’S CHANGING IN 2025?

Feb 3, 2025 | Podcast Episodes

A New Season, A New Name, and a Fresh Look at Your Financial Flight Plan

Welcome back.

As we kick off a new season of the podcast, you’ve probably noticed a few changes. We’ve got a new name, new artwork, and a renewed focus on helping professional pilots make smarter financial decisions throughout every stage of their careers.

What hasn’t changed is our mission. 

We’re still focused on one thing: helping pilots make informed financial decisions so they can build wealth, protect their families, and make the most of the opportunities this profession provides.

Why We Changed the Name

Many of you have asked about the transition from Pilot Money Podcast to Pilot’s Portfolio. The truth is pretty simple. When we began the trademark process, we discovered someone else had already secured rights to a similar name. Rather than fight a battle that wasn’t worth fighting, we decided to move forward with something new, and the more I’ve thought about it, the more I like the new name.

When we hear the word “portfolio,” most of us immediately think about investments, but as pilots, our financial portfolio is much bigger than the balance in our brokerage account. Your portfolio includes retirement plans, company benefits, union-negotiated programs, insurance elections, tax strategies, estate planning, and all the financial decisions we make throughout our careers. 

One thing we’ve learned over the years is that while pay tends to converge at the major airlines, benefits often do not. Two pilots may earn similar compensation, belong to the same union, and fly similar equipment, yet have access to very different retirement programs, healthcare plans, and company benefits, and these differences matter. More importantly, the strategies that serve us well in the first few years of our careers may not be the same strategies that make sense after we’ve built seniority, accumulated assets, and started thinking about retirement.

This season, we’re going to spend more time talking about how to maximize the opportunities available to us, when those opportunities make sense, and how our financial decisions should evolve as our careers progress.

More of What You’re Asking For

Last season, we alternated between solo episodes and guest interviews. I enjoyed those conversations, and I know many of you did too. We had some outstanding guests who brought valuable expertise and fresh perspectives.

However, many of the emails, messages, and questions you’ve sent in revolve around issues you’re dealing with right now. Questions about retirement plans, investments, taxes, airline benefits, and questions about financial decisions you and your families are actively trying to make. Because of these questions, we will pivot and spend more time addressing those topics directly. We’ll still bring guests onto the show, but we’re going to dedicate more episodes to answering the questions that are coming directly from the pilot community. 

Our goal is to create content that both sounds interesting and helps us make better decisions.

Don’t Fall Asleep at the Yoke

Let’s talk about markets. The last couple of years have been good for investors. The S&P 500 has produced very strong returns, and most of us have probably enjoyed watching our account balances grow. When markets are rising, it’s easy to become comfortable, and it’s easy to assume that because things have been going well, they’ll continue going well indefinitely.

As pilots, we know better than that. Recently, I was flying an instrument training flight in a Cirrus. We entered the clouds, and almost immediately we hit a pocket of turbulence that was significantly more aggressive than I expected. The airplane dropped, it rolled, and before I knew it, my head found the ceiling.

Once things settled down, my first instinct wasn’t panic, but rather preparation. I tightened my shoulder harness and suggested everyone else tighten theirs as well because the ride ahead might be rougher than expected. Investing is just like this.

Just because conditions are currently smooth doesn’t mean we should stop paying attention. We know markets rarely move in straight lines, which means now is always a good time to revisit our financial plans and make sure we’re prepared for whatever comes next.

Is Your Portfolio Still Aligned With Your Goals?

One of the biggest risks after a strong market is a portfolio drift. When stocks experience significant appreciation, the original allocation we established may no longer exist. For example if we intended to hold 70% equities and 30% fixed income, then after two strong years in the market, that mix could easily be much more aggressive than originally planned. The result could be that we’re taking more risk than we intended, often without realizing it.

This is why rebalancing matters. Rebalancing allows us to bring our investments back in line with our goals, risk tolerance, and long-term strategy. In many retirement accounts, we can do this without creating immediate tax consequences. The point is to make sure the portfolio we’re carrying today is still the portfolio we intended to own.

Invest Based on When You’ll Need the Money

Another question we should always ask ourselves is simple: When do we need this money? Our answer should influence how it’s invested.

Money needed for a home purchase in the next few years should be invested differently than money intended for retirement twenty years from now. Likewise, retirement planning requires a different mindset because retirement isn’t a single event. It’s potentially a twenty- or thirty-year withdrawal period. 

Too often we focus entirely on returns and overlook timing. The closer we are to needing a lump sum of money, the more important it becomes to protect those funds from short-term market volatility. As pilots, we spend our careers planning ahead. Our investment strategy should reflect that same discipline.

Watching Tax Policy Closely

One area we’ll be spending a lot of time discussing this season is tax planning. The Tax Cuts and Jobs Act provisions are scheduled to sunset, and many of us have spent years preparing for potential changes. What ultimately happens remains to be seen.

However, there are strong indications that we may continue operating within a relatively favorable tax environment for some time. If that’s the case, it creates opportunities. Additional years of favorable tax treatment can give us more flexibility to implement long-term tax strategies and potentially keep more of our hard-earned money working for our families instead of sending it elsewhere. This becomes particularly important for pilots with higher incomes and substantial investable assets. We’ll also continue monitoring estate planning developments and other legislative changes that could affect how we manage and transfer wealth.

LOOKING AHEAD:

I’m excited about where we’re headed this season. The new name reflects what we’ve always believed: financial planning is more than investments. It’s about understanding the full financial ecosystem that surrounds our careers as pilots.

Together, we’ll continue exploring airline benefits, investment strategy, tax planning, retirement readiness, and the countless financial decisions that shape our futures, but most importantly, we’ll focus on practical ideas that we can actually implement.

Thank you for coming along for the ride. We’ve got a lot of great topics to cover this season, and I look forward to helping you make the most of the opportunities available throughout your career.

As always, I love hearing from you. Send your questions to info@pilotsportfolio.com, and we’ll get them answered in an upcoming episode.

Until next time, thanks for listening, and thanks for reading.

TRANSCRIPT

Tim:[00:00:01]I’m looking forward to playing with, this name, Pilot’s Portfolio. Because you guys, a lot of you at the majors, right, we know that the compensation converges but, to be honest with you, depending on who you fly for, your benefits are very different. What the company provides, what your union provides you could be represented by ALPA that are two different carriers and have two different sets of benefits, right? So in this season, I’m looking forward to get going deeper in that and also discussing what types of benefits you should be taking advantage of and when. Because something that may be a fantastic strategy years one through five of your seniority, that opportunity might become less interesting to you as your seniority increases.
Tim:[00:01:18]Well, welcome to the Pilot’s Portfolio everybody, formerly called the Pilot Money Podcast. This is great. New season, new name, new art. This is awesome. great to be back behind the mic. It feels like it’s been a while so excited for today’s episode and then the rest of this season guys. This is the financial show for professional pilots. My name is Timothy P Pope. I’m your host. I’m a certified financial planner specializing in the planning needs of professional pilot. So in today’s episode, a couple of things I want to go over is I want to update everybody, let you know what’s changed, what stays the same and what you can expect throughout the season. I want to talk about last year’s market and what that might mean for you and how you can avoid falling asleep at the yoke if you will and then I’m gonna wrap up with just what’s on the radar that I think it’s interesting to everybody that listens to this show, but probably very interesting for those above a certain threshold and also above a certain investable asset threshold as well.
[00:02:17]So, we are going to dive into those, but first I just want to remind everybody. So why the name change? It’s so funny last fall, you know, going through full reviews and I’d be meeting with clients and then without fail at the end they say hey, so like, you know, what’s the new name gonna be? So to some of you guys knew what the new name was going to be because I would share it. So Pilots Portfolio so the show was formerly called pilots money podcast and last fall, you know, I talked about it during some episodes, but I went to go trademark that name and somebody beat me to it. In fact, they had just trademarked pilot money. [00:02:54]And so Pilot’s Portfolio, is different than Pilot Money Podcast. I do think the, previous name certainly had a ring to it. But I’m looking forward to
playing with, this name, Pilot’s Portfolio because, you guys, a lot of you at the majors, right, we know that the compensation converges. But, to be honest with you, depending on who you fly for, your benefits are very different. What the company provides, what your union provides you could be represented by ALPA that are two different carriers and have two different sets of benefits, right? So in this season, I’m looking forward to get going deeper in that and also discussing what types of benefits you should be taking advantage of and when. [00:03:34]Because something that may be a fantastic strategy years one through five of your seniority, that opportunity might become less interesting to you as your seniority increases. So, we’re going to talk about that throughout the season. But that’s why the name changed, guys. And, another change that we’re going to have this season is you will recall that in season one we alternated episodes. So we had a solo episode and then we had a guest episode. And, that was fantastic because we talked to a lot of interesting people who showed a real expertise in their field and I think brought some action to the table for you guys and for me to think about, I think that was a lot of fun. On the other hand, so many of you have written in and said, hey, Tim, have you you know, have you considered this question or have you done this analysis or, you know, you’ve had questions about things that are going on in your life.
[00:04:28]And so I would love to give you more of the content that you want. And, so one of the ways to do that is to have fewer guests. So I can have more time on the things that you guys are asking about and you guys are talking about. So looking forward to doing that. I suppose we could always go to a weekly show. But I don’t, you know, I’m not, I’m not ready to do that. Father of five and all the rest. No, we’re not ready to go weekly, but I would be interested. I’m trying to figure this out so, maybe if you guys have ideas, but I think a live Q and A could be a lot of fun and valuable for listeners. So I’m still thinking about that. And, I welcome your thoughts. You can drop a note. The link is in the show notes there. So I think the big takeaway here is look, we’re going to have fewer guests this season so we can get to more of the content that you guys are asking about. That being said if you have requests for content or you have questions, just drop a note or send us an email.
[00:05:21]The link is down there in the show notes, or if you have guests that you want to hear on the show, definitely let me know so I can reach out to them or have the team reach out to them and get them on since there is going to be fewer guest spots. Now let’s talk about the markets. So, last year the markets did well. There’s several indices you could choose from, but you know, I’m talking about the S& P 500 is widely considered to be representative of the broad market, although it’s only a large cap, right? It doesn’t get into mid small. And
it’s, of course, it’s only publicly traded companies, but in 2024 the market was up over 23%.
[00:05:54]In the year before that, it was up over 24%. Now, if you only held the S& P in your portfolio, you may have captured this return, depending on your timing of when you got in or when you got out and all of that. However, if your portfolio was diversified or you did not have a 100 percent stock portfolio, your returns could have been less. Or, if your portfolio was very concentrated and just a few, they could have been much higher. The point is that the broad market itself did really well last year and the year before. And, by the way, I want to mention, when you guys log into your 401ks, a lot of times you see your personal performance and, a lot of times that’s different than what the actual market is doing. And, the reason is because your personal performance is calculated using a dollar weighted return. And that considers the influence of cash flows. So, if there’s a quarter where the market’s down, but you still got paid, six times that quarter, then you bought a lot of shares when the market was down.
[00:06:55]And, then when the market rebounded, your performance is going to look better than, say, a time weighted return. So, if you want an honest look when you’re evaluating your portfolio compared to a benchmark, you’re going to want to use the time weighted return.
[00:08:11]So, back to the fact that in 23 the market did well and in 24 the market did well. Most people don’t complain when their portfolios are going up, right? But what does that mean for us? That we’ve had several years of pretty decent market returns. You know, I’m going to tell this story because I think illustrates the point here. So, you know, the other week I was flying the Cirrus an instrument training flight. And the weather was great for instruments, by the way. I got a lot of actual that flight. So we hit 600 feet. Caps is alive. Turn the autopilot on. Controller gives us the cruising altitude. So we’re climbing and we enter the base of the clouds and boom, right? We hit a pocket.The plane kind of drops and y’alls to the right. I expect a bump when I go into the clouds, but that caught me off guard. Okay. I was a little surprised there and I was watching the autopilot cause I wanted to see, like, is it going to disconnect? Is it going to hold?
[00:09:08]Am I going to have to start hand flying it? And during that jolt, I actually, so plane goes down, I go up. We were in the middle of a climb. I hit my head on the top of the ceiling. Okay? And, so after things stabilized. My hands just kind of instinctively came back to the seatbelt and kind of like cinched it down, you know, the shoulder harnesses and, I had two of my kids in
the back and I said, hey guys, you know, you might want to tighten your seatbelt up it could be a bumpy ride. You know, we had the weather up on the MFD and it was just yellow, right? We were going to Charleston. It was yellow from, Charlotte to the coast. And so what’s my point during good market years when the portfolios are rising, times are good and the next downturn could happen. Right? Catch you by surprise. Okay, just like that jolt there caught me by surprise, now I’m not saying that we’re on the brink of a recession or anything like that. In fact quite frankly, there’s a lot of optimism for economic growth, you know we’ve got a business friendly president with favorable tax policies that actually cares how the market responds to his initiatives so, you’ve got that on one hand, but on the other hand, there are a lot of moving parts to our economy.
[00:10:13]Okay? And quite frankly, a lot of times when you enter a recession or enter a downturn, it may not be because of what’s, you know, the policies that are being implemented right now. It’s policies that have been implemented some time ago and that are working their way through the system. So I think that leads us to the question, what should you do? Markets have been great. Portfolios have been increasing in value. What should you do? Number one, you want to make sure that the risk that you’re carrying your portfolio. It meets your comfort level and it’s appropriate for the goals that you’ve set. and I think that that is the biggest thing. And, actually I spent a lot of time talking with clients about making sure that the risk tolerance matches the risk capacity. And then the portfolio is being true to both of those and, you know, rising markets by default. It means that the portfolio is going to need to be realigned. So what do I mean by that? If you set up certain allocations of large cap, mid cap, or small cap, all of those don’t grow at the same rate. You’re going to need to do some rebalancing. Each of those asset classes has a different risk profile.
[00:11:14]If you’ve got some equities and then some bonds or some fixed income, I would be extraordinarily surprised. If your equity position did not pull away from the percentage that you had set it originally, and if your bond position did not shrink from a percentage basis, right? That’s just what rising markets do and so, what you can do is you can rebalance that and bring that back in line with the risk profile that you set up initially. I’ll tell you last year we did a decent amount of rebalancing for clients because of this very fact, right? Markets have been up. What we do, we locked in the gains and if you’re rebalancing in a retirement account, there are no taxes to pay for the moves that you make. You know, as long as you’re not pulling the money out. So, make sure you pay attention. Don’t fall asleep at the wheel there. And pay attention to how the risk profile of your account has changed in a rising market. The opposite is true, by the way but that’s not our reality, so we’re not really talking too much about it. But in down markets, the risk profile also changes, and I
think depending on your personal risk tolerance, it can take some courage to say, hey, you know what? The equities have dropped by a decent percentage, and it’s time to put more into what has fallen and that’s the way to do it.
[00:12:30]So the first thing is, look at your portfolio itself to see what risk changes you need to make. The second thing that you can do is just make sure that your money is segregated appropriately on a timeline of when you’re going to need it. So, if you need these dollars in less than five years, and you’re going to use them for a lump sum and that’s, that’s where it drives all the difference. Say, we’re looking for a house down payment or some other goal where we need the money in a lump sum, we probably don’t want much market exposure. We probably don’t have much market exposure in that case. However, if it’s going to be 5 to 8 years and we need the money in a lump sum, then maybe we’re looking for a balanced portfolio. Right? So we’re definitely interested in doing more than inflation, but it’s okay if there’s some market risk in the intermediate term because we expect the market to go up and to the right, during that time frame And then if you don’t need the money for more than 10 years but, let’s say you need it in a lump sum then we might be more comfortable with risk on.
[00:13:29]And the reason I stress lump sum so much is because this strategy is different than say, when you’re coming in for retirement. So you’re 65, of course, all your money’s not going to be in cash because God willing, you need that portfolio to support you for another 20 to 25 years. Okay? And so kind of tweak the withdrawal strategy a little bit differently for retirement, which is a very long time horizon of withdrawals versus I need the money in a lump sum. So think about that. When do I need the money? And then how should it be invested or not invested, which is an active choice to make that based off when I need it. So, I wanted to mention that just because we’ve had a couple of years of really good market conditions. We haven’t had an extended period of down markets when 22 came and went. But it’s not like, 2007 to 2009, where you really tested your patience with your investment strategy, right, during those years. So, just make sure that you’re keeping an eye on your risk there after these excellent, two excellent years of market returns.
[00:14:31]I want to switch gears now. And talk about what we’re looking forward to. And, I know particularly what I’m looking forward to this year. Is, I want to see how this administration’s tax policy is going to shape up. Okay, we all know that the Tax Cuts and Jobs Act is set to expire at the end of 2025. And for years I’ve been talking to clients about this. and say, hey, we got to prepare for this. But, you’ll remember that in 2017, it was President Trump that put these tax policies in place. So although they’re set to expire or sunset, as we say are they going to go back to pre 2017 levels? Probably not. I think very good
indications that, you know, revert 100 percent back. Okay? And, in fact, I think that whatever the tax policy looks like, we could reasonably expect it to be favorable for a little while longer. And, so what this does is it gives you more time to implement a tax strategy. That’s going to leave more of your hard earned money in your pockets. Right? Because, I think the long term projection for income tax in this country is probably that they’re going higher. Okay? Because there are historically lows right now, and the country needs the revenue none of that is a secret.
[00:15:46]I mean anybody who keeps up with economic policy or monetary policy like that, none of this is a secret. And, so we welcome more time, particularly if you make, you know, $400,000 a year or more. Oh, your investable assets are over 2 million. You are most certainly interested in how you can use some additional time to make sure that you keep more of what you’ve earned, so definitely looking at tax policy this year, I expect to be talking about it a lot, particularly as things heat up and you know how that applies to you the pilot at home that’s flying and listening to the show and tuning in for ideas on how you can implement this, right? The other thing is estate planning changes are scheduled to revert back. So we’re going to keep an eye on that as well to see where that settles. So guys, super excited that you joined me, new season. New name, new art on this show. So excited for all the things that we’re going to discuss and thanks for joining this episode of pilots portfolio.We’ll see you on the next one.
[00:16:49]Thank you for joining this episode of Pilot’s Portfolio. If you found this information helpful, spread the word and share it with a pilot buddy. Or if you have questions and there’s something that you would like to hear discussed on the show, send us an email. You can find the address in the show notes. For those of you who are ready to learn how we help professional pilots with their financial planning needs, schedule an appointment. Until next time, keep the shiny side up and we’ll see you on the next episode.

Financial advisor and author of Pilot's Podcast, Tim Pope

Timothy P. Pope, CFP®

Timothy P. Pope, CFP®, is the Owner and Principal of 360 Aviation Advisors, a firm dedicated to helping professional pilots and their families achieve financial freedom. As a financial advisor for pilots with over 13 years of experience in personal finance and a Bachelor of Science from Wake Forest University, Timothy provides expert guidance on wealth management, retirement planning, and investment strategies tailored to aviation professionals.

An avid pilot himself, Timothy flies a Cirrus SR20 and loves exploring mountain biking trails with his kids, blending his passion for adventure with family time. Follow along for practical insights on financial planning, investing, and building wealth while living life to the fullest.

Timothy P. Pope is a Certified Financial Planner™and principal owner of 360 Aviation Advisors, LLC (“360 Aviation Advisors”), registered investment adviser firm. Investment advisory services are provided through 360 Aviation Advisors, in its separate and individual capacity as a registered investment adviser. Podcast episodes are provided through Pilot’s Portfolio, in its separate and individual capacity.

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