Preview:

When the market is crashing, it’s easy to feel like you’re the only one who’s ever felt this anxious. But the truth is, some of the greatest investors in history have lived through chaos, and they left behind wisdom that still applies today.

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More About This Episode:

In this episode, Ryan responds to wisdom from experts like Warren Buffett, Benjamin Graham, and Jack Bogle to remind us how to think, act, and stay grounded when everything feels uncertain.

We’ll connect each of these great quotes to real investor behavior, showing how fear and emotion are the biggest threats to your long-term success. From staying the course to avoiding market timing traps, we’ll use this wisdom to discuss relatable examples and mindset shifts for investors who want to win by being steady, not reactive.

Here’s what we cover in this episode:

📉 Buffett’s “greedy when others are fearful” lesson

🧠 We can be our own worst enemy

📊 Jack Bogle’s ultimate advice: “Stay the course”

⚠️ Why timing the market usually backfires

📚 An expert’s advice on handling unseen risk

0:00 – Intro

1:45 – Warren Buffet

3:53 – Benjamin Graham (author of The Intelligent Investor)

4:35 – Jack Bogle (founder of Vanguard)

8:57 – John Templeton

9:53 – Peter Lynch

10:49 – Morgan Housel (author of The Psychology of Money)


Resources:

Retire Pilots – https://retirepilots.com

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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 

You know, when the market’s crashing, it’s pretty easy to feel like maybe you’re the only one who has ever felt this anxious. But the truth is that some of the great investors in history have lived through this kind of chaos before, and they left behind some wisdom that still applies today. So what we’re going to do with today’s episode is talk to Ryan Fleming, the pilot’s advisor about some of the great quotes from voices like Warren Buffett, Benjamin Graham, Jack Bogle and others to remind us how to think, act and stay grounded, hopefully, even when times feel very uncertain. I’ll grab Brian and we’ll get started. Ryan, Ryan, great to be with you again here on the pilots advisor, looking forward to covering kind of a fun episode today as we talk about crashes in the market downturns, but learn from some of the greats how to react, how to stay calm, maybe during these times, and a little bit of what to do. So this should be pretty fun. How’s life treating you? My friend, and outside of the markets in the financial world, life’s

Ryan Fleming 

pretty good. I have young kids, so I’m constantly between soccer games and track meets and you name it. So just busy, busy time, busy time of year. Of course, the topic today, I think, is an amazing topic, because investing is all about keeping your cool and being unemotional. And, you know, I like to tell my clients stuff like, you know, on average, the markets up three out of every four years. So, and to be honest with you, most years there’s a 10% correction that happens, but we fail to realize that when it happens like and we forget the pain that we felt when, when it, you know, if it was a couple years ago, and when the market’s down. So I think it’s a great topic, and I’m excited for it Excellent.

Walter Storholt 

Well, here’s what we’re going to do. Whether we at the time of this episode, markets are down, it may still be down. By the time you’re watching it, we may have come back up out of it. So the whole point here, though, is that this is going to be some pretty timeless advice. So if the current crash or the current downturn has fixed itself? Well, take and absorb all of this information and put it in your brain and use it for the next time there’s a downturn in the market. So I think that’ll still be applicable here. All right. Well, let’s start with the greatest of them all, Warren Buffett, and it’s a pretty popular quote, so it’s an easy one to start with here, be fearful when others are greedy and greedy when others are fearful. The wisdom here seems pretty sound, but it’s still hard advice to follow, isn’t it?

Ryan Fleming 

Well, for sure, it’s very hard, hard advice to follow, because, you know, when there’s blood in the streets, it’s hard to not react. And we all know to buy low and sell high, but we just don’t do it. Us as human beings. And I love behavioral finance, because that behavior, the human behavior, is normally what hurts us. That natural reaction, fight or flight, is what hurts us. So like I was saying, we all know to buy low and sell high, but that emotion inside of us causes us to do the exact wrong thing with the market. So it’s really tough to battle, and I think it’s important, you know, for those listeners that may not know who Warren Buffett is, or may not know who some of these investors are, he’s probably known as probably the one of the best investors of all time. And I think some of his other quotes that I think of is, you know, basically, you want to be doing the exact opposite of what everybody’s thinking, you know, the the hurting effect. Yeah, I think

Walter Storholt 

that makes a lot of sense. What do they call Warren, the the Oracle of Omaha? Is that sort of

Ryan Fleming 

monitor? Well, he still lives in like, a 1300 square foot house, and he’s like, a, you know, I don’t know, what does he have? Like, $48 billion and he’s never moved out of his house, yep.

Walter Storholt 

And I think still drives his old truck around, you know, that kind of thing. So he’s frugal in some ways, in addition to the greatness in the investing side. Well, that’s great advice. Interesting. You talk about liking, kind of the behavioral finance side of things. I think you’ll really like the next quote here the author of a book called The Intelligent Investor, Benjamin Graham, once said that the investor’s chief problem and even his worst enemy is likely to be himself. How does that one speak to you?

Ryan Fleming 

It speaks to me, because I immediately think about PILOTs. Pilots will not get out of their own way. Or, you know, you’ve heard me say it before too. Like, you know, I’m going to cut off my nose to spite my face, right? You know, there you go. And you know, whether it’s emotions in the market or fees, or whatever it might be, sometimes you gotta get out of the way and let the let the market do its thing. And I kind of, I kind of relate it to flying too. I mean, sometimes you just need to take your hands off the controls and let the plane do what it was designed to do. And that’s fly, you know, versus if you’re over correcting and, you know, just trying to fly too much of the airplane, let just back off and let it be a little bit so 100% I mean, if you look at dal bar, who, you know, Dow bar is a firm out. Boston, and all they do is study investor behavior. And many of my clients and prospects have probably heard me talk about this, but the average investor is getting well below market returns. I mean, it’s around 4% which is sickening. I mean, that’s barely beating inflation. And so if the average investor is getting 4% the question becomes, what are they doing to screw this up? And if you start digging into the data, it’s all the worst enemy you’re, you know, stock picking, market timing, track record investing and just not being a long term, unemotional, disciplined investor.

Walter Storholt 

Well, talking about long term and discipline, it dovetails very nicely into the next piece of advice from the founder of Vanguard, Jack Bogle, he said, Stay the course. No matter what happens, stick to your program. I said, Stay the course 1000 times, and I meant it every time. It is the most important single piece of investment wisdom I can give you. Jack

Ryan Fleming 

Bogle, when I hear that name, Vanguard. Love it. Love that company, low cost, ETFs, index fund, index funds. I think that what’s crazy about this, though, is I think the investment environment has changed, and I’m going out on a limb here, but this is what I truly feel. I feel like for the longest time, that passive portfolio, you know, low cost ETF keeping your expense ratios very low, set it, forget it, and just let, let it do its thing. With modern portfolio theory, I think it might be a thing of the past. I mean, I really do, because with with technology, with AI, now there’s so much automated trading in the market, if you I mean, even if you look at it, as soon as there’s uncertainty, all sudden, there’s a massive sell off, and a lot of that is because of automated trading. And so the up and down, I mean, it’s wild and crazy. And I think for the first time since I’ve been in this business, I really think active trading is having a little bit more of a piece, and you can see it with some of the long term returns of what we do. And once again, the narrative of doing something versus nothing probably helps the investor as well, versus having that passive portfolio when the market’s in turmoil and you’re just riding it all the way down. So you know, it’s tough because I see Vanguard, and I think it’s been such a pivotal piece of the investment world. But I think, I think things might be changing.

Walter Storholt 

It’s what, it’s one of the kind of a bit of a new normal sort of feeling to it with the way that the markets behave now, yeah,

Ryan Fleming 

yeah. I mean the massive volatility, the, you know, spiking up, spiking down. I mean, it’s, it’s definitely much harder to trade, for sure, but at the same time that volatility also creates a lot of opportunity, and if you could figure out how to unemotionally take advantage of that, or you have a system to take advantage of that, you can really get some fabulous returns

Walter Storholt 

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Ryan Fleming 

think we were just talking about that on a podcast, and I was mentioning that, yeah, it doesn’t matter. You know, 2000 was different from oh five or oh eight, or, you know, 2019 2022 it’s always a different narrative. And you see all the pundits, well, this time, it’s different. I don’t care what the circumstances are, we’re going to come out of it. There will the sun will eventually come up. I constantly say I don’t know if the next 20% is up or down. I have no clue, but I know the next 100% up because it always is. And if you can stay true to that and be unemotional and not look at the, you know, the two week outlook, the 90 day outlook, or even the six month outlook, and look at markets. I mean, it is the greatest wealth creation tool known to mankind, if you’ll just get out of the way and let it do its thing. Good

Walter Storholt 

lessons there, for sure. We got two more to go, Ryan, this next one’s from Peter Lynch. Far more money has been. Lost by investors preparing for corrections or trying to anticipate corrections than has been lost in the corrections themselves. I,

Ryan Fleming 

I 100% agree. I feel like you should read it again, because it I don’t know what else to say about that is, except, you know, don’t try to time the market like you. You trying to, you know, Miss 5% of the downside, ultimately, probably causes you to miss 15% of the upside, you know, and it’s a loser’s game. Yep, we

Walter Storholt 

saw this, you know, during the prior downturn, where there was that one day where the NASDAQ spiked 10% plus. And if you’d been trying to get out of the way at that time, you would have missed that, run up and you would have fallen victim to exactly what Peter Lynch is talking about here. So fits right in with that. Stay the course mentality. Of course, one more behavioral finance. One for you. This one’s from Morgan Housel, who is the author of psychology of money. Really good book, by the way, if you ever want to check it out, folks, definitely a good one to recommend. Risk is what’s left over when you think you’ve thought of everything. That’s pretty interesting. One,

Ryan Fleming 

no, it’s very interesting. I don’t even know how to respond to that. What do you think about that one? Walter, well,

Walter Storholt 

when I hear that one, risk is what’s left over when you think you’ve thought of everything, it just means that it’s always it’s always present, like you can never ignore it, you can never get rid of it, you can never solve for it. Risk will always be a part of anything you do in life, and it’s the true for investing, at least that’s what it speaks to me as, yeah,

Ryan Fleming 

absolutely. I think of it too. When there’s a big market downturn, or you hear me say all the time, you know, pilots want all of the upside and none of the downside. And it’s, it’s so interesting to me, how you find out what somebody’s true risk tolerance is when you have a market downturn. Let’s say a portfolio has a 10% return, but the s, p is up at 15% a pilot is going to instantly go, Well, why the hell? Why am I not getting 15% what do you know? This, this portfolio sucks, you know. And then, no different, when the markets down, you know, why is my why is my account down? Like, if there was some magic pill when the markets down 15 or 20% that you’d miraculously have, like, positive returns somehow. And so you really get to see what someone’s true risk tolerance is in bad markets, and that’s why we actually reach out. Not everybody chooses to fill it out, but we constantly send out a risk tolerance questionnaire, and I think we do it every six months just to test the waters and say, hey, you know where you at? Here’s here’s how your money’s invested. Do you want to make any changes? I

Walter Storholt 

want to see you send that out during a crash and see what the how different the responses are. But it brings up a great point, because it’s one thing to say, Oh, I’m comfortable with a 20% downturn, and then when what happens, you’re going,

Ryan Fleming 

yeah, exactly, living through it, and the pain that you feel right now, while it’s happening, and you feel like, quote, unquote, I just lost, you know, 20% of my money and, and, but you know, all the data supports it. I mean, if you go back and look at any of these crashes or pullbacks, if you stayed the course and you didn’t panic, you’re gonna win. Yeah.

Walter Storholt 

Well, there’s the lesson for today. Stay the course. We’ll go back to that quote from Jack Bogle, the founder of Vanguard, even if times are changing a little bit, that advice certainly has not gone away quite yet. Just stick with your strategy. Don’t make knee jerk reactions. All the greats agree that that’s the way to get through these things when they happen, if you don’t have a plan in place for the next market downturn, Well, time to get acting. It’s never too late to get started and start making the right decisions. But if you wait until the next crash happens, well, then it is too late, so jump on it while you’re thinking about it right now, meet with Ryan and have a conversation about your financial plan. Get guidance on how to better prepare for your financial future. Where does it all begin by going to retirepilots.com. Retire pilots.com. We’ve got it linked in the description of today’s show go and order the retirement toolkit that Ryan has created for you, for pilots, specifically, you can get that for free. That’s the starting point for everybody. So go check out the toolkit today. Retire pilots.com. Your place to pick that up. It’s linked in the description of the episode, and it’s that easy, Ryan. Thanks for the help today. Appreciate it. Appreciate it.

Ryan Fleming 

As always. Walter, and for our pilot types out there, I just want to leave you with this. If you’re flying an airplane and you hit some turbulence, you got to stay the course. You don’t just go grab the parachute and jump out the window, right? So get a little turbulence. Ride it out. Things will be okay. Take a deep breath.

Walter Storholt 

That might be fun for the pilot and not so much fun for everybody else on the plane. And

Ryan Fleming 

that’s why we fly boxes around at FedEx. I don’t have to worry about that. There you go. All right, have a good one. Thanks, as always see, right? Thank you.

Speaker 1 

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