Preview of what we’ll cover today:

🚀 Aggressive Investing: Why speculation isn’t a strategy

💵 Playing It Too Safe: The hidden risk of cash

📈 Power of Compounding: Time is your greatest asset

⚖️ Finding Balance: Taking risk with a purpose

✈️ Pilot Perspective: Why discipline beats prediction

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More About This Episode:

Risk is unavoidable. The real question is whether the risk you’re taking makes sense for where you are in life.

In this episode, Ryan explores three common financial personalities among people in their 30s and 40s, and the steady contributor quietly building wealth over time. If you’re trying to figure out whether you’re taking too much risk—or not enough—Ryan offers a practical framework for evaluating where you stand and where you want to go.

Go Deeper Into The Episode:

0:00 – Overview of the 3 types

2:42 – The aggressive investor

3:51 – The cautious saver

4:55 – The steady contributor

5:28 – Why consistency often wins

6:42 – Free portfolio analysis

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 0:00
On today’s episode of The Pilot’s Advisor, we’re talking about risk. It’s unavoidable, but you’ve got to make sure that you’re taking the appropriate risk for where you are in life. What we’re going to do on today’s episode is look at a specific stage of the financial journey. We’re going to look specifically at younger folks, those of you who are in your 30s and 40s. We’re going to look at the different approaches that you might be taking to risk right now with your financial plan. Are you aggressive, cautious, somewhere in between? Which one’s the right one? And we’ll break all that down coming up next. Back on the pilot’s advisor, Walter Storholt, alongside the pilot’s advisor himself, Ryan Fleming. And Ryan, good episode today. We’re gonna jump right in. We’re talking about those that are in their 30s and 40s, aggressive, cautious, are you somewhere in between. We’re going to describe what those look like in this age bracket, typically, and maybe you’ll self-identify with one of these as you’re watching or listening to today’s episode. And then I’m going to be curious, which one of these concerns you most, Ryan, as a financial advisor, if someone’s finding themselves in one of these positions, sound good,

Ryan Fleming 1:05
sounds wonderful. Let’s do it

Walter Storholt 1:07
all right. So, the aggressive one might feel behind, you’re trying to make up for lost time, you’re heavy on individual stocks, crypto, high risk plays intrigue you. The logic is, hey, I’m young, and I’m young enough to recover if things go wrong, all right. And that’s the aggressive one, cautious one. I’m spooked by market swings. Those don’t feel very good. I keep most of my savings in cash or low-yield accounts, things that don’t go down very often. And my logic is, you know, what I’ve saved money, I’d rather not lose what I have. And then we have the somewhere in between folks that maybe they’re consistently contributing to that 401 k, maybe a Roth. They’re not thinking about it too much, and they’re kind of taking that slow and steady approach. First of all, you work with a lot of pilots, Ryan. Do you see people falling into these different categories more one than the other? And is there one that concerns you the most?

Ryan Fleming 1:58
Yes, and yes, and yes, and yes, the first thing I’ll say is I’ve been, I’ve been a financial advisor. It’s scary to think about, but I’ll be pushing, you know, 20 years here in the next couple years of doing this, and so I’ve seen a lot, I’ve learned a lot, because I’m one of those people that constant education, you know, you constantly want to educate yourself and get better, find a better way, and I think about, I’m trying to think back to me being in my 20s, 30s, and 40s, and, and all the mistakes that I made, or what if I could go back now, it’d be totally different, right? And so, not only am I going to talk about the different ones that you just brought up, but, but how, God, if I could go back and I do it better, right? So, the aggressive one you talked about, heavy on individual stocks, you talked about crypto, high-risk plays, right? So, immediately makes me think about Vegas, right? You know, we got, we’re at the table, we’re going to double down. What are we doing with our money, if we’re doing that, we’re speculating and gambling, we’re big or we’re going to lose big, right? There’s a reason why there’s so much, so many great, nice hotels at Vegas, right? It’s because, because you’re paying for those and you lost that money, and you’re going home with, you know, with your head down, because you made some stupid plays, and it didn’t work out for you. So, in your 30s and 40s, I’m all about being aggressive, but you got to do it with calculated risk. You have to have diversification, you have to have a portfolio to handle the ups and downs of the market, but Who cares if that that company or this company over here failed? Because you have diverse diversification, we don’t want leverage in individual positions. So, the aggressive one can definitely relate to that. I see it a lot with Robin Hood and Betterment. I’m glad you’re investing, but let’s do it the prudent way. You’ll thank me later, you’ll thank me later, because you won’t have those huge market swings. The cautious one, when you’re that cautious in your third 30s and 40s, that’s not good, because you need to let your money work for you, you need to let your money grow, and if you’re putting money in cash, you’re going broke very safely. I can just tell you right now, you’re going broke very safely. If you put in low yield accounts, high yield savings account, I like to think of it as you’re in, you’re in that swimming pool, and you’re just treading water. Is that, is that a life? Where do you are you going anywhere? You’re not, you’re really not helping yourself out, and you got to get out of your own way and let your money work for you. I think it’s great that you’ve been saving and put money away, but you’re going to be in no different position, maybe even a worse position if you keep doing this when you’re in your 50s and 60s, because you’re losing to inflation, so your time horizon is so long you have to get in the game, and I think the people that can’t do this, they just don’t really understand the markets, and they don’t understand how to have exposure to the markets, but also not hurt themselves. So, a lot of that might just be education, somewhere in between consistently contributing to a 401 k, maybe. In a Roth, but not thinking about it too much. The funny part is, is this – this might be the person that’ll win in the end, because they’re not speculating and gambling and losing half their money every couple years. So it’s almost like the target date fund, or you’re not doing very well, you could be doing a lot better, but you’re not making those mistakes to keep starting over. You know, it makes me think of a Paul Abdul song, three steps forward, two steps back.

Walter Storholt 5:25
Yeah,

Ryan Fleming 5:26
yeah, we want.. we don’t want to be that person. So, so 30s and 40s, be disciplined, but don’t speculate and gamble. And, man, if I could go back, if I could have more consistently put money away and done it in a prudent manner, because of the power of compounding interest and the time factor being the biggest factor. Oh, I wish I could go back, because then life would be so much better right now.

Walter Storholt 5:48
Yeah, so the somewhere in between person is kind of getting it right, maybe, maybe pay a little bit more attention, but that slow and steady consistency is where it’s really at. The aggressive one and the cautious one, you’re concerned about both of those, for those various reasons, we need to come toward that middle a little bit.

Ryan Fleming 6:04
It reminds me of the pilot that is constantly online and analyzing stocks and trying to do it all himself, versus the person that’s just consistently putting money away, and they’ve almost said it and forget it. They tend to be way better off than the person that is constantly buying stocks in and out of the market, you know, constantly messing with it, and I get to see the balances over time of the difference between those two individuals, you know, and the somewhere in between person is much better off when they come to me in their 40s or 50s, because they didn’t lose 80% of all their money in one year,

Walter Storholt 6:37
yeah,

Ryan Fleming 6:38
and I get to see it all, but I, unfortunately, I could see the good and the bad.

Walter Storholt 6:42
Well, if this is you, you’re in your 30s, your 40s, and you’re kind of putting yourself in one of these categories, and say, yeah, maybe I’m maybe I’m that aggressive one, maybe I’m too cautious, I need some help coming back toward the middle. That’s where a free portfolio analysis with Ryan and the team is really helpful and important. You can get that by ordering your retirement toolkit, packed with Ryan’s book and other great information. There’s a link to it in the description of today’s show. And again, when you get the toolkit, not only to get all that good stuff to help you learn about retirement, but you can also get a review and that portfolio analysis as well. So schedule that and get your toolkit by clicking the link, and you can also go to, of course, Retire pilots.com Ryan, thanks for the help. On our next episode, we’ll break down people that are in their 50s and 60s, what they look like if they’re too aggressive, maybe too conservative, and what the middle ground looks like there as well. So, that should be fun.

Ryan Fleming 7:34
Sounds good.

Walter Storholt 7:35
Awesome. We’ll tackle it next time. Thanks for joining us here on The Pilots Advisor.

Speaker 1 7:43
The 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.