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  • Business, Culture, Ethics, Podcast, Society

Your Grind Decade

  • Rick Jordan
  • August 21, 2025

About the Episode:

I was filming a TV show called Two-Minute Drill with David Meltzer last week. Pitch show format like Shark Tank but for pitching not funding. I was a guest judge alongside pro athletes and celebrities. One of them was Austin Eckler. Running back for the Los Angeles Chargers. And this dude’s intensity blew me away. Austin’s face was frozen in concentration the entire time. So intently listening to every pitch that they had to do reaction shots of him after because his expression never changed. You could see how he plays football just by watching him judge these pitches. That devotion to the moment. That intensity. It was insane to witness. After we wrapped Austin comes up to me. Starts asking about my life. Kids. Business. Sports. Then he hits me with this question. What’s your biggest financial tip for me. I’m like excuse me. Here’s a dude making millions of dollars a year in the NFL asking me for financial advice. And I found out he’s only 27 years old. What really struck me was when Austin said he loves getting around people who are older than him. One generation above. Because of the wisdom that takes place. And I truly believe wisdom doesn’t actually start until you get into your 40s. I wasn’t wise in my 20s. Wasn’t wise in my 30s. But now in my young 40s I’m starting to see things differently. There’s no rush to figure it all out if you’re in your 20s or early 30s. Society puts pressure on you but get around people one generation above you. Let their wisdom accelerate your journey. Austin asking me for advice reminded me how powerful that generational wisdom exchange can be.

 

Listen to the podcast here:

Watch the episode here:

 

Episode Topics:

  • Learn why trying to have it all figured out at 18 is setting yourself up for failure.
  • Discover the decade-by-decade blueprint for building real wealth and wisdom.
  • Find out why your 40s are your money-making grind decade according to successful entrepreneurs.
  • Understand how to accelerate your success by getting around people one generation above you.
  • Get the financial strategy that NFL players and entrepreneurs use to never lose money.

 

What’s shakin’? Hey, I’m Rick Jordan, and today we’re going all in. Today I’m coming in hot because I got my espresso with me, and I’m really excited about this. I love pumping up with an espresso every morning. And there’s something that happened last week. I was actually filming a TV program with a bunch of really cool people, David Meltzer and his crew. It’s called two minute drill, and the show is a pitch show. It’s not a funding show like Shark Tank is, but the format’s kind of similar. I was a guest judge in many different episodes, and what was really awesome about this is, on every single show, there was always either a pro athlete or a celebrity who was also one of the judges. And I had just an amazing time. Met a lot of really awesome people, made new connections. And one of the things that really drove me home was this one dude, Austin Eckler. Austin is a pro football player, a running back for the Los Angeles Chargers. And, I mean, he’s well known in the NFL, just an amazing player. 

It was really fun watching him, because his expression on his face as we were listening to these pitches. I mean, you know me, I’ve got a lot of huge facial expressions, a lot of movement, right? But this dude, you could tell how he plays the game because his face was just so serious and intently listening the whole time, to the point to where they had the two reaction shots of him after just because his face was literally stuck like freeze frame in a lot of these shows, just because he was so intently listening and wanting to catch every single word. It was really cool. And you could show how his devotion to what’s going on in the moment, at least on the show, would also be the same thing as when he’s playing on the field. You know, just his intensity was insane to me. It was awesome. 

Though I love this because I pick up things from other people when I look at them, and they inspire me, right? That’s the flip side is what I’m going to talk to you about today, because I didn’t actually know what his age was, you know? And then I found out after we wrapped this one show that he’s 27 years old. That’s it, just 27 years old. And of course, the dude’s making millions of dollars. He’s an awesome individual. We’re going to connect afterwards; we’ll swap numbers and everything. But after the show, we’re out of the studio, and we’re just talking in, like, the common area, and he comes out, and he’s like, “Dude, tell me about you.” He’s like, “You got kids, you know?” He’s like, “How long have you been in business? What do you like to do? Do you play sports and all these other things? And then he’s like, “What’s your biggest financial tip for me?” It’s like, “Excuse me,” and it’s like, “Not that I’m not doing well, right? “But you look at pro athletes, and they’re making literally millions of dollars a year, right? Just lots and lots of money. And of course, that means that there’s a lot more to manage. 

There has to be a lot more discipline or intensity, as you could see in his face, in order to maintain those dollars. Because there are so many athletes, there are so many even that are like in the military or anything, or even winners of the lottery. As soon as they win and that cash flow stops, they end up going broke because they don’t know how to manage that money. You know, they’ve got this huge influx, and they buy all the cars, all the watches, and everything. And this dude, Austin, was just so down to earth. It was incredible. And then he says something to me, and I’m, like, my biggest financial tip.” I’m like, man, like, have you heard of an IUL? I’m like, I just put this in place to use. Like, I just put mine in place last year. He’s like, I locked in at like, 11 and a half percent, he gets all excited, you know? Like, I locked in, like, 11.34, so we’re like, right there, brother. Like, it’s amazing, right? You never, you never lose money on this thing, and it makes you millions in the years to come, because it just sits there. 

And I’m like, Dude, I’m like, You got, like, because you’re, like, 15 years younger than me, you’ve got another 15 years for this to cook, because this type of policy is it’s a compound interest principle, so the longer that it can sit there, the more it builds upon itself. And another 15 years means that he will, in essence, have, like, four times the amount of money that I could have had at 42 years old. Yeah. Yeah. So we’re talking some more, and we’re swapping some interesting business insights, and everything is like, Dude, it’s like, I appreciate you. I love getting around people who are older than me, like one generation above me, so I can hear all the experience and amazing things that they’ve done in order to get where they’re at and what they even see for the next 20 years of their life. And this, this really struck me, because I’m looking at it the same way now, at this phase in my life. You know, back when I was mid-20s, I always thought that I was a little bit weird, because I liked hanging around people in their upper 30s and their 40s, and. 

Is because I didn’t see many other people doing that. And that’s really like, where my business coaches were that age. It’s like I could always look up to them and see where they’re at. And now, being in my early 40s, most of my mentors are in their 50s and 60s, it’s because of that one generation beyond me, where they’ve seen more things than me, experienced more things than me, and even, probably most important, made more mistakes than me. There are things that they’ve gone through that I can’t even fathom yet, but they’ve seen it, or they’ve seen it in other people. And when Austin came up to he’s like, I love getting around people who are older than me. At first, I was like, man, now I feel like I’m old, you know, because he said the phrase, you know. But at the same time, I mean, he’s like, Dude, you look like you look like your young 30s, though, man, that’s what I thought when I first saw him like this, right? I’m gonna maintain this look forever. 

I think, however, he’s saying, you know, I love being around these people who are just slightly beyond me in years because of the wisdom that takes place. And I truly believe, I don’t know if I’ve said this before, I truly believe that wisdom actually just starts to begin when you get into your 40s. And I look back, because I don’t think that I was wise in my 20s. I don’t think that I was wise in my 30s, but now I’m starting to recognize and be more aware in my young 40s; that’s a good phrase. I like that in my young 40s that I’ve actually seen a thing or two, done a three or four, and there’s more for me to do that I can pull on this stuff now, because if you’re in your 20s, that’s a time to just try a bunch of different things, multiple things. And Austin, I mean, he’s dumping money into a restaurant, he’s dumping money into another TV show. He’s investing in like nine or 10 different things to try to dip his hands in all these things. Because pro football or any sport, for that matter, is not a lifelong thing, right? When you’re actually a player on the field. So now he’s actually, I’m looking at this, and I’ve always had this mindset that your 20s is a time period to just try everything you possibly can. 

I don’t believe, and I hate the fact that, at least in America, that in the US, that when you’re 18 years old. You’re expected to have it all figured out. You’re expected to graduate from high school and then go to university, go to college, and know your major decide in, like, a matter of literally three months. Actually even before that, from when you end high school to when you start your higher education, you have to know what you’re going to do for the next 60 years of your life, and not to mention, all of a sudden, hey, you’re a legal adult, and you’re expected to be fully responsible for all of your actions and also figure out what you’re supposed to do for the rest of your life. And society places all this pressure on this demographic, this age, to just have it all together. I think it’s stupid, because it’s just that you’ve got so much time, and if wisdom doesn’t start until you’re in your 40s, because you haven’t had the breadth of experiences yet, your 20s should be a time where you try as many things as you possibly can, whether that’s professionally, personally, hobbies, or whatever. 

Just try everything that interests you, because there’s so much time to recover from huge mistakes after that. And I actually kind of hope that you make some big mistakes, or that you learn from others’ big mistakes, so you don’t have to make those same ones. There’s nothing like making a mistake and being able to recover through it, I’m telling you, and you have to have time to be able to do that. I’ve made my own huge ones over the past 20 years. And then after your 20s, when you get into your 30s, your 30s are a time to kind of like, hone in on a couple of those so you can start to filter out the things that you’ve tried that you’re like, “Well, that sucked,” or “I suck at it,” or “This isn’t something that really interests me anymore,” and you can start to kind of hone in on these things and start to build a foundation for yourself. And then when you get to your 40s, your 40s are really a time, and I’ll never forget this because a client told me—my very first client who owns six Buffalo Wild Wings, the very first client to reach out—told me that, Rick, when you get to your 40s, that’s the decade that is your busiest.

It’s your grind. You make the most money in your 40s. And I start to see this now with everybody that I meet; it’s like the 40s are the years that things start to blow up for you, because you have put in all the mistakes, and you’ve laid the foundation. You’ve tried all the things, and you’ve honed in on something that you feel you actually want to do. And then when you get to your 40s, it’s time to go all in on that thing and continue to crush it and push and push and push and push until you can’t push any more, and then you still have that one more left in you. Yeah, and then you get to your 50s, and it’s like, man, look at all this stuff. And then you can start to have your money make money and begin to just impart wisdom that you’ve gained through your 30s and your 40s into those that are younger than you, like Austin, and show him some cool things. And they can probably show you some cool things too. 

But there is no rush, none whatsoever, to think that if you’re in your 20s, or you’re 18, for that matter, or even in your early 30s, that you have to rush to try to figure these things out. I know there’s this pressure from society around you, but the best tip that I can have for you is to get around those who are just like one generation above you, one generation beyond you in years. It’s something that has imparted wisdom into my life and allowed me to accelerate faster than I could have on my own, and it was accentuated this week and brought back to my intention by hanging out with Austin Eckler when he was asking me for financial advice and business advice because I’m just 15 years older than he is; it was absolutely amazing. And when you get to the 40s, that’s the time to go all in.

Your Grind Decade

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Rick Jordan is CEO & Founder of ReachOut Technology, and has become a nationally recognized voice on Cybersecurity, Business, and Entrepreneurship.

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