Preview of what we’ll cover today:

⚖️ Pros & Cons: Why multiple advisors often backfire

🗄️ Financial Junk Drawer: Accounts scattered everywhere

🧩 Consolidation: Getting assets aligned and working together

🧭 Advisor Roles: One pilot vs. too many hands on the controls

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More About This Episode:

Having two financial advisors might seem like you’re getting twice the wisdom, but it often creates confusion instead of clarity. In this episode, Ryan explains why splitting assets between multiple advisors leads to conflicting strategies, inefficient portfolios, and what he calls the “financial junk drawer.” If you want confidence instead of crossed signals, this episode helps clarify who should really be in control.

Go Deeper Into The Episode:

0:00 – Intro

1:57 – Listener Question: Two Advisors, Twice the Confusion

2:17 – Reasons people have more than one advisor

6:28 – Can multiple advisors work?

7:18 – Consequences of conflicting voices

11:20 – How to consolidate

Resources:

Retire Pilots – https://retirepilots.com

Get your FREE Retirement Toolkit – https://bit.ly/3ZmZsaX

Pilot Tax – https://pilot-tax.com/

The Pilot’s Advisor Podcast is also on video. Watch & Subscribe on YouTube: https://bit.ly/3EIEBW2

Connect with Pilot-Tax: https://pilot-tax.com/

Episode Transcription:

(Note, this is an automated transcription. Please forgive any errors.)

Walter Storholt  00:00

You know, some people think that having two financial advisors really means double the wisdom, but it might actually mean double the confusion. I’m going to grab Orion, and we’re going to talk a little bit today about whether there’s wisdom or not in having multiple financial advisors helping guide you to and through retirement. Let’s get started. We’re back again on the pilots advisor Walter Storholt, alongside Ryan Fleming, of course, the pilot’s advisor himself and Ryan. Great topic today that I know you can’t wait to light up actually inspired by one of our viewers on the YouTube channel. And they’re asking, I’m gonna read the question in a second, but they’re asking about, Hey, is it wise to work with multiple advisors? Maybe they’re rethinking things a little bit. I know you’ve run into this before and have some pretty strong opinions on this, right?

Ryan Fleming  00:45

I absolutely have a strong opinion on this. And the best way to talk about it with pilots is, if you pass somebody the airplane and two people are flying at the same time, or you pass somebody the airplane and say, Hey, only use the rudder pedals. It’s not going to work out.

Walter Storholt  01:00

That’s a great point, because actually, someone could assume, if we were connecting the dots here from the pilot perspective, well, hey, a plane has multiple pilots. Why can’t I have multiple financial advisors? But you’re kind of talking about an important nuance already in that, in the plane, it’s not two people literally flying the plane at the same time. You’ve got split duties, right?

Ryan Fleming  01:19

Yeah, one person needs to be flying the airplane at any given time, and it should be very clear who’s flying the airplane. So when I talk to a prospect, I flat out tell them, I said, I I manage all your assets or none, and if you want to, you know, if you want to keep your old advisor, then have at it. But you’re probably talking to me for a reason, right? And I don’t care if it’s your brother, your sister, your you know, cousin, it really comes down to numbers, and if you care about your financial future, then you need to pick one advisor and trust them and go with it, so that you can see the full financial picture. And so all your assets are actually working together in unison, because it really matters.

Walter Storholt  01:56

Yeah, well, let’s look at this actual question from our viewer. The Viewer says, For years, I’ve had half of my money with one broker and half with someone else. They’re both nice guys, and I thought it would be good to get advice from two different people. But now it just seems confusing. Am I better off having it all in one place? We’ll answer this person’s question specifically in a few minutes, but let’s zoom out just a little bit. Ryan, why is this thing happening in the first place. This question asker, the situations you’ve run into before, what’s the motivation? Why do people split their money up like this to begin with? What are they thinking are maybe the advantages, or maybe some of the causes for, you know, the situation?

Ryan Fleming  02:33

Well, it kind of reminds me when I see people with a financial junk drawer, where they have assets all over the place, you know, it’s kind of a mess, and I think it has to do with them wanting to spread, spread their thing, spread things out, so they’re not putting all their eggs in one basket. Per se, I could see multiple, multiple opinions, or also looking at one account versus the other and constantly, you know, analyzing them against each other. And the problem with all those things Number one, if you don’t consolidate your assets and see them and have them organized, then you don’t really know what’s going on. Number two, the way portfolios work, if you actually have a prudently engineered portfolio, sometimes it’s going to be up, sometimes it’s going to be down based off of what it’s invested in. And so I’ve watched people, I mean, this honestly happens all the time, where one year, one of this portfolio, we built up 28% and the s, p is at 16, and they’re like, Oh my God, I want more of that. Okay, well, what you’re doing is ultimately chasing returns, because the very next year, something in the market, maybe International, is a lot higher, and the US markets are down. Well, now it’s flip flopped. That old portfolio is performing much you know, that was performing much better before is now not looking like it sucks. So I think it creates a lot of different problems, and I don’t think it helps a client at all, versus finding an advisor they trust, focusing on the long term and not looking at the short term noise, but making sure your money is consolidated, organized, and working

Walter Storholt  04:05

together, it seems like you’re also describing the fact that this isn’t always intentional. Sometimes this is a default or an accidental thing that somebody falls into.

Ryan Fleming  04:13

Well, I think it most of most cases. Once I start analyzing some of the investments that people have, I think it’s it happened over time. It’s that financial junk drawer. I got a little bit of stuff here at Edward Jones T Rowe Price has this over here. Oh, I forgot about this account over here at Charles Schwab, oh, my god, first command, yeah. You know, back when I was a lieutenant, I started this account. And once again, we call it the financial junk drawer. I think step one is getting organized, getting your assets consolidated, getting them to where they’re actually talking to each other. Because if we don’t do that, we don’t really have a clue what’s going on or what you have the other time you see it is people that worked at multiple jobs, maybe they did a bunch of regional airlines, people. Four. They got to that legacy carrier, and they got four in one case, spread all over the place. Don’t even remember where they’re at. So it, it is, I think, step one and trying to improve your financial life is getting consolidated and getting all your money in one place, so you can see it all and know what’s really going on

Walter Storholt  05:23

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Ryan Fleming  06:36

I really don’t think so. I think it’s actually just setting setting things up for failure, no different than CPAs. I mean, there’s so many CPAs out there that are tax filers, and they don’t strategically tax plan at all. And if somebody has a CPA like that, we’re going to have totally differing opinions, which is why the CPAs I work with understand pilots. Pilot situations are vastly different from the average person out there because of what the company does with be fun contributions and so many other things that knowing an airline pilot’s lifestyle really matters when we’re starting talking about tax planning. So we want to make sure that you have people that are aligned the other the other factor, you know, I think you brought up conflicting advice. Do you really want to two advisors and now they’re saying totally opposite things? Yeah, one says buy, the other says sell. And it doesn’t mean that one’s right or wrong. I mean, you could have different strategies, and that’s why, why Once alone, you need to find an advisor that’s aligned with your with your feelings, with with your values, with your impressions of the market, of the government, maybe even politics, I don’t know, because that’s going to find how you’re going to react to different things. And I think when, like, when I start thinking about tax strategies, I think about, you know, where pilots know that they have to save for retirement, but they really don’t understand the distribution phase, and this is where pilots are vastly different, because you have to have a unified tax strategy between an advisor understanding how that 401 K plans built and a CPA to understand that we’re thinking about something that’s going to affect this pilot when they’re in retirement, right before they’re 73 with RMDs. And what we’re going to do inside their four 1k today is going to be a lot different than said CPA, that doesn’t understand this at all, and they’re just trying to get a small reduction in somebody’s adjustable gross income. I mean, you can see

Walter Storholt  08:35

that going wrong in a lot of like, multiple ways, right? Hey, I’ve got two financial advisors who do the same thing? Well, that’s going to create its own problems, but it’s also going to create issues if you’ve got one advisor who specializes really in just, let’s say a broker, versus someone who’s thinking about the long term and what the consequences are at 73 where the broker probably is not paying any attention to that kind of stuff. And so again, another example of where you would have this split in opinion, this split in goals, understanding of where the client wants to go, decisions that you would make it somebody’s 55 year old birthday are way different than what the broker would recommend because of those two different visions. And so just all sorts of different ways

Ryan Fleming  09:13

it can go wrong. Well, yeah, and you might have overlapping investments that you know, if all your assets aren’t talking to each other, you have overlapping investments that create a bunch of inefficiency could actually get you in a risk tolerance that overall is probably not good for you, harder to track performance, harder to track fees. The only time where I think it could, I still, I don’t think it would ever make sense to have multiple financial advisors, but we’re, I think about it, more of a holistic team. You know where you have your financial advisor, but that advisor needs to talk to your tax attorney. And maybe we have a tax attorney that specializes in estate planning for a high, high net worth individual. All those things together, working together in unison. And can really be beneficial, but two financial advisors that might have differing opinions, absolutely not. You could have two advisors. Let’s say I had a junior advisor on staff, and we had the exact same vision for you, and we discussed it, and we’re perfectly aligned. Well, then it would be okay, because then it’s like, okay whether I’m talking that’s different, yeah, whether I’m talking to Ryan or Dave, you know, we’re on the same page, and we have the same goals and and we might be discussing it internally, just how to get you in the best possible position.

Walter Storholt  10:30

Yeah, I like how you position that. Hey, we’re talking about a team. We’re very different roles, well defined roles, boundaries, not to overlapping financial advisor roles. So that’s a huge difference that you outlined there.

Ryan Fleming  10:43

I think to close it, what I would say is, at the end of the day, having two advisors usually is going to create more confusion than confidence. I think that people tend to do it to try to spread out their eggs diversify. But I think it has the exact opposite effect when you think about not putting in all your eggs in one basket, that’s all about portfolio construction and having true diversification in your portfolio all talking to each other. If it’s all spread out over the all over the place, it actually probably makes the problem worse where you probably don’t have the diversification you’re looking for. I did

Walter Storholt  11:20

want to ask you one more thing, Ryan, before we wrap up, if you can tell me how messy is this? So if somebody comes to you and they’re like, Hey, I’ve got multiple advisors, let’s just say It’s Jeff. I think you know the person who asked the question today. Let’s just say I’m just making up a name, but let’s just say Jeff says, Hey, am I better off having things in one place? Let me get a review with you and see if that’s the case or if, let’s say somebody wanted to do that, is that messy, to undo all of this stuff at different advisors offices and implement a new plan? I mean, it kind of sounds daunting to a lay person, so how would you handle that if somebody came to you and said, Hey, I hear you. I’ve got this situation. I want to consolidate everyone. We’re under one roof.

Ryan Fleming  12:00

Well, I think that’s what I do every day. When somebody comes to me and asks for portfolio analysis, I’ll actually analyze their portfolio and what they’ve been doing, and we can make a comparison, whether it’s just looking at the numbers, looking at performance, looking at fees, but what they ultimately have to do is decide which advisor they want to fly with. You know, do you want me to be your pilot or co pilot, or do you want that other advisor to be your co pilot? And if you decide that you want me to be the man, well, then what we’re going to do is we’re going to consolidate all your assets and get them all together and talking to each other. That’d be step one. If you don’t want me to manage all the assets, and you just want me to manage your 401 K, I’m going to tell you that I don’t do that, and it’s not in your best interest. And I think a lot of a lot of clients or prospects, they’re like, that catches them back like, whoa, I’m trying to give this guy a million dollars. And he’s saying, No, well, because it’s that important, it’s that important to have one person flying the airplane.

Walter Storholt  12:55

Yeah, I like that a lot. If you want to safely get to your destination, this is the way to do it, right. And so much like you have very strict rules, regulations, checklists and plans when you’re flying your plane, same thing when it comes to retirement, you want to be following it to that level of detail, that level of attention, so make sure that you are doing those exact things with your financial future. If you’d like to talk to Ryan a little bit about what that would look like, go through a portfolio analysis and see where you are right now, where you can improve your situation into the future. It’s actually very easy to do that. All you have to do is go to retire pilots.com that’s where you’ll be able to order your retirement toolkit. It’s packed with Ryan’s books, resources, other great information that’s all going to help you better prepare for your financial future. And best part, it comes with a free portfolio analysis where you get to meet one on one with Ryan, and so if you’d like to do that again, go to retirepilots.com we’ve got a link in the description of today’s show that you can find easily as well and set up that time to review your portfolio, get your free toolkit and get in a better place for your financial future. So I appreciate your thoughts and opinions on this particular topic, Ryan, I know it’s one that can be controversial, but I appreciate your perspective on 100%

Ryan Fleming  14:05

Well, thanks for asking me the questions, and I’m always here to help any any listeners out there. I think step one with any of this order the retirement toolkit. But why not have a free portfolio analysis? I mean, why not have somebody else look under the hood and maybe get you in a much better path going forward.

Walter Storholt  14:22

It’s all you have to do. So again, click the link in the description to set that up. Otherwise we’ll see on the next episode. Come back and join us again here on the pilots advisor.

Speaker 1  14:33

Information is for illustrative purposes only and does not constitute tax investment or legal advice. Always consult with a qualified investment legal or tax professional before taking any action.