Pickleball Strategy, Drilling & Business Lessons with Jennings Smith

[00:00:00] Trust me, I've rated more people than anybody listening to this podcast right now. And I'm telling you right now, if I ask you what level of pickleball player you are, you're going to tell me you're a 4-0 player. Let me tell you right now, you are not a 4-0 player. With that being said, you know without a shadow of a doubt when you walk onto this court what it's going to take in order for you to be a 4-plus-0 player. And it's not going to be just showing up to the court. You have to have a plan. You've got to work. You've got to dive in. You've got to get a lesson. You've got to adjust. It's just like business. There's so many parallels to it that I love so much.

[00:00:50] Good morning. Good morning. Hey everybody, Coach Tommy here live from the Pickle Rage in North Charleston with a special edition, believe it or not, hard to believe this, 50th episode of Smashing Plastic Podcast. And we'll have a round of applause by Sean, our producer, that'll put in after that. But yeah, 50 episodes. And I couldn't think of a better way to have our 50th episode than to have our returning guest, Mr. Jennings Smith. You guys know him. You guys love him. He was our first guest. Now he's our 50th guest. 50 episodes, Jay.

[00:01:16] Hey, you know, you're in the top probably 5%, maybe 2% of podcasts. Like most podcasters quit after like 10 episodes. So to make it to 50 is huge.

[00:01:27] Well, I remember you specifically telling me this and I have the luxury guys of being with Jennings almost on a day-to-day basis, but I remember him, me and him kind of read each other and it's a, I think it's a good pull. But I remember him making that statement to me when we were talking podcast, because if you don't know, and we'll make sure we drop it in the, in the notes, but Jennings has a fantastic podcast himself. And I remember him telling me that specifically of, Hey man, the secret of this thing is, is to keep going, right? Like to legitimately keep going. And we're going to talk a little bit in this episode about that.

[00:01:55] But I do fully want to let you know that I acknowledge when you told me that of, Hey man, you get past 10 episodes, you've done something. Cause most people don't do it. Yeah. My, my 20 listeners are really counting on me to keep producing my podcast. Well, your wife and your children really enjoy your podcast. This is mind you as well. My mom thinks it's great.

[00:02:16] I, uh, I think it's fantastic. If you haven't listened to his podcast, you gotta, you gotta, it's called unlock your life. And there's a lot of great stuff that he goes over. And of course you talk business and you talk real estate, but there's a lot of nuggets that you go over there just on your day-to-day grind. And I think that's what I want to talk about because I do think that it's parallel. And I think you would agree to pickleball.

[00:02:33] Like again, so just so you guys know, we do two episodes a month. So basically two years is what we've been doing this podcast. And me and you were playing pickleball two years ago. You were just, I want to say, we want to use the word series, but you were getting like to the point where you were hooked. And now legitimately, I think two years later, I'd love for you to got just to tell everybody, Jenny's where you're at in your pickleball journey from two years ago. What does that look like?

[00:02:57] Yeah. You know, I got addicted to it, just started playing, loving it, um, playing a lot of rec play. And I was probably around maybe a three, five, three, six, you know, at that point. And, um, and I really was getting frustrated. Um, and I would say the breakthrough was drilling. I started drilling with Noah pretty consistently with you pretty consistently.

[00:03:25] And, and, and that broke me above the, the, uh, the four O level. Um, and I will say there's a lot of comments on this pickleball. Isn't as fun. We know the better you get because you're kind of restricted with, this is the level of players that you can play with now.

[00:03:46] I agree. And, you know, for me to go out to Laurel street and just, you know, not have a crew that I'm rolling with, but I'm just going to show up and play with random people. It's like, okay, it, it, at this level where I'm at now, you know, that's, that's not going to be so fun. And so, you, you know, you got to evolve with who you're going to play with. And you want to play with people that are better than you. So you continue to get better. Um, but I still got a long way to go as was exposed yesterday by Felix. Uh, he was making me run around like a clown, popping up his dings, hitting everything.

[00:04:16] Yeah. So I got a ways to, as there's still progress to be made for sure. But I, and I will give you your flowers, man. You are definitely a much better player. Um, you're leaner, you're more fit. You've stayed way more, you know, regimented into your workout, which is a big part of it because your athleticism obviously is able to show you're nice and big at the net. But more importantly that I feel like your pace of play and what you're trying to do is so much more planned and you kind of legitimately, you and I will converse or whoever you're playing with will converse on a tactic of what you're doing, which is very parallel to business, right? Like we don't just go in there

[00:04:46] and hopefully wing it. A lot of times you need to have a plan. And I personally believe that's one of the biggest separators. If you guys are listening to your pickleball game is you will get to a point to where you start legitimately strategizing what you're doing. And I don't mean just the X's and O's, but I mean, playing against the Jimmies and the Joe's that you're playing with. You, you agree?

[00:05:05] Yes. And I see that where some people are, they're more committed to personal growth in, in all areas, right? It's like, if I'm going to do something, I want to get better at it, whether it's real estate, um, you know, apartment complexes, uh, raising capital or pickleball, right? You know, it's, it's like, uh, I don't want to just stay in the same place. And if you just play rec constantly,

[00:05:33] with the same people at the same level, you know, there's not going to be any, any progress. And so it's like, you know, I'm, I'm watching reels, I'm watching videos, I'm looking at new shots. I'm trying stuff. Like something that was really difficult was the drop, like a third shot drop. Like I'm not good at it. And so I would just blast it up there and hope that they would miss it. And as you play better players, that, that hard drive, that's too high, honestly, for most of the time for me, they're just, I mean, they're just blocking that right.

[00:06:03] Your feet or angle and the points over, it's not going to work. But because my third was bad, I didn't want to use it too much. And, and so it's like, okay, well, you're never going to progress unless you just start drilling that third, getting to the net. And then, then my dinking was really, really exposed. And so I'm like, okay, I got to move my feet. I've got to get way better at this. I still have a ways to go.

[00:06:24] Sure. I know. Sure. I know. Sure. I absolutely agree with that one. But, but yeah, it's like, you got to be willing to do the things that you suck at to get better at them. If you're going to progress, you can't just like stick with the one thing. It's like, okay, I got, I got fast hands at the kitchen and I like hands battles and I've got a really hard drive. So those are my two components. That's not enough. You've got to become a holistic player.

[00:06:49] And also it's, it's calming down. Like, you know, when it's eight, eight, you know, are you tensing up? Are you forcing shots? Are you taking, you know, things that aren't there because you want to end the point quickly? Or are you like settling in saying, okay, you know, let's do the drop. Let's get to the net. Let's think, let's wait for them to get something a little high. Okay. Speed up's not really there and I'm not going to take it. It's that decision making that I didn't have before where it was like, I'm just going to smash everything and try to,

[00:07:19] you know, end the point. Hey everyone. Coach Tommy live here from Smashing Plastic Pickleball. Some of you know this, some of you don't, but I actually own a construction company by the name of First Class Painting and Restoration. One of the things that we have ventured into over the last couple of years is court building. Believe it or not, we've done it for municipalities. We've done it for homes. We've done it for businesses. So if you are in the need or in the desire, I should say, of having a court either built or resurfaced, we would love to give you an estimate. Come out and take a look at that project.

[00:07:45] If you would just simply shoot an email, DM, or you can text us and we'd be more than happy to get out there and line you up for a fantastic, beautiful first class court. Talk with you soon. Coach Tommy out. Yeah, I feel like it's super easy to get into what I'll call like absolutism. And I see this in baseball. I see this in pickleball. I see this in business. Like this is the way that we've always done it. So we're going to continue to do this win, lose or draw. And most of the time that's going to yield into losing.

[00:08:11] And I feel like, especially when I did the clinic with Dane, Kenridge, because shout out to, you know, coach D. But also it really like exposed me to how much you need to be able to open up your mind and talk with your player, whether it's your female partner that you're playing with or your male partner in pickleball.

[00:08:27] You need to really have those conversations back at the net of like, hey, let's let's try this. We don't necessarily need to stack or maybe we do stack like having the ability to mix things up and have conversations to plot through this beloved world of the game to 11. I think is something that most pickleball players, especially four or five and under don't even really entertain. They're just literally playing whack-a-mole. Let's let's hit the ball. It's fun.

[00:08:50] But if you really do want to get better than it does become. And Dane said this better than anybody. It's putting the puzzle together on each point and then putting the puzzle together on each match like it literally is. You need to look at this as a puzzle that's laid out to you on a table and you're figuring out the edges and then you're figuring out how to fill in the middle. I thought that was a great analogy for me. And he even made the point of where he breaks his matches up into quarters.

[00:09:13] So if you're playing to 11 points, basically every three points, you're kind of acknowledging where you're at and you're either staying with that plan because you're working or we're adjusting this now. We're not waiting till we get to 8-0 and we're down of, oh, my gosh, maybe we don't need to stack on this match. Yeah. And shout out to Dane. I don't know what he did to you, but there was a definite change in your play style after that. Right. Right. Where, you know, it used to be Machine Gun Tommy. Yeah, while I'm out of control.

[00:09:42] And you are a far better player in the last three, four months just from going to that event. Yeah. I talk with, you know, when we were playing yesterday, you know, one of the things that we got done, I talked with Jasmine, one of the female players that we're playing against, who, by the way, shout out to Jasmine. She is, gosh, she's become so much better of a player.

[00:09:59] But what I was telling her is exactly kind of what you just said is like, hey, you're so much better now with your skill set that you really, in all honesty, now it's the mind stuff of understanding that you really do just need to start setting up the points per point to your angle to win because you are far. You have all the shots, right? Like, even back then when I was wild and out of control, like I have all the shots, but are you playing them when you need to play them? Or are we just going into smash and crash? Are we just going to try to hit winning liners, liners?

[00:10:27] Or like you said, I think at the end of the day, that's the biggest difference for me is I feel like the pace of play. So wherever you're at right now, my tip is the pace of play in which you're playing really does determine so much more of the output of what you're going to be able to get from your game. And what I mean by that is you don't have to be just wild and out of control and trying to win a shot with one swing. It can be tactful. And when you learn that and you can strategize like what you're tactfully trying to set up, which I feel like Felix does better than probably any player that we play right now.

[00:10:57] I mean, every single point is a tact, something as I'm setting up for the next shot. I feel like I do that better now than I did four months ago. Yeah, yeah. And the strategy, you know, I've played with some players and they're really good at identifying what's going to work in that match, right? They poke around, okay, the right side player has a weak backhand. This person doesn't like to be sped up on. Yeah, it doesn't like the drive or whatever.

[00:11:27] And if you never poke around and find that weakness, because once you find it and then you can target it, it's far easier to win. And, dude, I never even thought about like, well, let me poke around and find out where they're bad. But like Sager, he's really good at like identifying opponents' weaknesses and then targeting those things. And I'm trying to get better at it. I'm not as good as some.

[00:11:50] But once you figure it out, because I have been beat by players that I feel are less athletic, not as good, but they poke around. They find the one thing that I'm bad at, which is, you know, the corner drop to my backhand. And I either speed it up, which is stupid, or hit in the net. But for me to hit a really controlled kind of passive dink right back to the middle to set us back to equal, you know, that's what I'm trying to do now. It's a tough shot, yeah.

[00:12:20] But that's a tough shot. And so it's like they can beat me if they continue to do that over and over again versus the players that just continue to drive at me and try to bring power to me. That's what I want. You're feeding right into my game, you know. Yeah. Dane, you know, talked a lot about like the superpowers and identifying your superpower. And I believe 100% that is definitely your hands and your counters are, I think you would say the same thing. That's like the super power that you have in your game. So me playing against the net from you, it would be unwise for me to feed into that, right? Like I need to make you move.

[00:12:49] And you'll hear me say this to you all the time, but I literally do. I try to play behind you. Whenever me and you are across from each other, I'm always trying to play behind you. I'm never playing in front of you. I don't want to get into the counter battles and watch you smash a third shot drop. I don't want to do that because we're going to lose the match because you're so lengthy and so long. And it is literally the strongest part of your game. It is wise for me to go the opposite way of that.

[00:13:11] And so many pickleball players that are listening right now and that I watch, you continue to do the same exact shots and you get the same results, which I think is the definition of insanity. Like mix it up, right? Mix it up. What do you got to lose? And going back to the drive versus the drop, like the drive might be the shot. If they're popping up your drive and you're getting, you know, points off that. Yep. Stay with it. Go with it. And you got to poke around to see, oh, wow, they got a really good counter. That it's not going to work. I got to, you know, I got to get up to the kitchen in a more tactical way.

[00:13:42] To transition from that, man, what I love, and I know there's a lot of listeners that are into this stuff like I am. And how does that work in business? Because you and I can agree, and everybody that's listening to this podcast, the last 24 months of our business careers are different, right? It's different today, especially in the scene of real estate. What do you do in regards to even how we do pickle? What are you doing right now in the world of real estate and your multifamily and all of the different stuff that you have rocking and rolling that's parallel to this poke, prod?

[00:14:10] We'll use the word pivot. Like, what are you doing right now that you weren't doing 24 months ago? Yeah. I mean, that's an interesting question. Good parallel. I think you have two ways to go. So, like, you can make excuses. You can say, well, you know, the economy is not as good as it was. Rates are going up. You know, commercial real estate sucks right now. Gas is high, whatever.

[00:14:40] Gas is high. Yeah. Trump is screwing up the economy or whatever. Or you can look at, like, okay, where are the opportunities? Because there are opportunities in every market. So, it's kind of like that poking around. And so, what I'm doing, you know, is I'm getting better, right? So, with multifamily, a lot of our properties were under third-party management. Okay. So, third-party management, you know, a property manager, they report to you.

[00:15:07] And you have just another layer of disconnection from your property and how it's performing. So, we've taken the property management in-house on all but one property, and we're taking that in-house this fall. So, it's like we've built a team around that. And it's like drilling. Like, this is how we do the rent rolls. This is how we do the delinquencies. This is how we read the reports. We've got key people that are running that now.

[00:15:32] And our properties have become more profitable in maybe not as good of an economy than they were when the economy was roaring because our expense ratios are lower. You know, so even though our rents aren't necessarily up, our income coming in from those are because we got better at what we do. You're more efficient at what you're doing. Right. And so, that's one thing. Another thing I've looked at is, you know, pivoting with more of the commercial side because when you buy something, you've got to think about the whole package, right?

[00:16:01] So, when you buy an apartment complex, it's going to be a lot of hands-on management and a lot of dealing with toilets and tenants and evictions and delinquencies, et cetera. And so, one of the things I've done to add to my portfolio is higher-grade commercial tenants. So, we bought a retail suite in downtown Somerville. We've got a financial advisor and like a siding and roofing company as our tenants. We bought a dental office. Tenant is a dentist, believe it or not.

[00:16:31] Imagine that. And, you know, those guys pay. They pay before the first every month and they are also on triple net leases. So, the expenses like rising taxes, rising insurance costs, rising maintenance costs, those are passed along to the tenant. Got it. So, you can say, well, he's paying me $12,000 a month in rent plus he's covering my expenses. So, I know that as long as he pays, I'm going to actually make $12,000.

[00:16:58] You collect $12,000 on a multifamily, you know, you may have $6,000 of expenses. You may have $8,000 of expenses. You may have $13,000 of expenses. You know, it's harder to gauge what you're actually netting because those are all-inclusive leases where you're covering all expenses of the landlord out of the rent. And so, you know, there's pros and cons to each asset class.

[00:17:19] But getting more into commercial where it's like I can continue to buy these things without overloading my team with the management responsibilities but still keeping it in-house. And then the development, I don't know if you want me to touch on that. I would love to. I think you would agree, and I'm hoping that you and I are having another conversation of this about a year from now. But I don't know if you chalk this up as your biggest win.

[00:17:45] I know for me working with you personally on this, it's really cool, you know, not to get emotional. But you've been grinding for this next thing. So, I want you to get your flowers on it. So, tell people what you're working on and where we're at with that. So, last summer, late summer, I identified a four-acre parcel in Somerville. Okay. And it was zoned mixed-use community. So, it was zoned commercial. Okay.

[00:18:14] Got a great deal on it. And my vision was to build these contractor warehouses. Okay. They're 22-foot wide, 50-foot deep. And they've got a bathroom. You can put an office in them. And it's small bay flex. Got it. Flex warehouse space. And the reason that I was keen on doing this is, you know, I'm kind of pivoting. Like, I'm going where who moved my cheese. I'm going to where the cheese is moving. Good book, by the way.

[00:18:42] Small businesses, they need spaces, right? And there are more service businesses than ever. And there's, like, a lot of people growing in that field with the advent of AI and that threatening white-collar jobs. There may be more and more people going into this industry. And so, these guys don't need 20,000 square feet. No. They don't need a massive warehouse. But they do need something. They need an HQ. They need an HQ. They need a bathroom. They need a warehouse. They need an office.

[00:19:11] And they can't spend $1.5 million to go buy, you know, their own place. And so, I thought, if I can build 34 of these all in one, you know, business park, essentially, and do it under a condo association so that, you know, we're sharing some of the costs there. But they still own their real estate. I think it would sell. And so, I ran test ads. Got a huge response from that. Okay. That gave me the confidence to put this thing under contract.

[00:19:41] We've now closed the land. We've developed out the plans. And the whole time, I'm trying to mitigate risk. Because development is, I mean, it's kind of the big boy world of real estate. It's the major league of real estate. You can make a lot of money. You can also crash and burn. Right. And so, we are pre-selling these units. And we started out, you know, at a certain price point. And we got nine of them pre-sold at that price point. Okay. Then we moved the price point up.

[00:20:10] We got another six sold. Then we moved the price point up again. And we sold another one. Got two more in the hopper that may or may not happen. But at this point, we got 16 of them pre-sold, which is enough to cover our entire loan and then some. And so, we still have, you know, the investor capital that's going into the deal. But that gave me a lot of confidence that, okay, I'm hitting a winner here. People want this. They need this.

[00:20:37] Some people are buying them to rent them out, you know, to small businesses as investments. But yeah, it's a big undertaking. And I've learned a lot. You know, if you're not a little bit queasy and scared of what you're doing, are you really growing? And, but I've learned, you know, how to source land, the development process. Like, it is a huge deal to get a land disturbance program.

[00:21:01] And we are now just got the final approval from Dorchester County Public Works on our stormwater. And our LDP will be issued in the next week or so. So, I'm really excited to get over that hurdle. We can break ground on the project. But, but, but it's also trended towards, I've got another pad under contract in Somerville, you know, and I probably wouldn't have seen the value in that pad had I not been educating myself in this, in this field. And that's just what I'm talking about.

[00:21:31] Like, the growth of how do I get better at commercial real estate? Instead of saying, well, I don't understand land, entitlement, development, and how that stuff works. It seems hard. It seems complicated. It's like, well, who does know about that? How can I pick their brain? How can I talk with them? How can I mitigate the risk on this, on this thing? And hopefully it works, you know. Well, I, I'm proud of you, man, as, as your buddy and as your compadre on the side, it's really inspiring for me to see kind of how you've navigated,

[00:21:59] not just through your business, obviously through your pickle, but obviously this one big project that has really been something that you've been really sold out and dedicated to. I'm excited to see it come to fruition. And I hope and pray that, you know, 12 months from today, not only is it, you know, well underway, you might be really close to being done, right? I mean, what's, what's your projection on how long is it going to take for that thing to be done, done? Yeah. I mean, initial projections were done by December of this year.

[00:22:25] But we, that was getting the permit in, you know, May or, sorry, sorry, March. So, you know, we're, I'm, I'm hoping by, yeah, 12 months from now, we should be wrapping it up and hopefully have them all sold. All sold and done done. And it's operating, which is a huge win. Huge win. I've set the expectation with the investors of a two-year timeline because sometimes, you know, it may take longer. We may have construction delays, et cetera, et cetera. So I want to give myself some, some leeway there. Yeah, it gives you, give you a runway.

[00:22:55] And I think at the end of the day, one of the things that I want to, and again, I don't want to, you know, I think that we're tying our listeners with pickleball, but how much of this relates into you and your game when pickleball is the same exact way? Because there really are, like, if you truly, one of the, one of the things and caveats that's going on right now with pickle, and I'd love for you to feed on this because you hit on this a little bit earlier, is you hear the word clicky now, right? Like, that's a thing with pickle. Like, well, you know, it used to be this, now it's that. And my personal opinion on this is, is simple.

[00:23:20] I think that from what I have seen as a coach, and I have coached, you know, a lot of players, and I have seen a progression of a lot of players that are choosing to get better. And I've seen a lot of players who have chosen not to get better. And the disconnect between those two is where I believe these clicks start happening to where, like you just said, it's tough for a guy or a gal that's really a 4-0 or 4-5 to have a whole lot of fun with a 3-0 player. Yeah. Yeah. Yeah.

[00:23:50] And, I mean, the clicks are, they're necessary. Right. You know? Right. And as a lower level player, you need to have the self-awareness that that is a group that I don't need to play with because I haven't earned a spot there yet. Right. You want to play with people that are, you know, better than you. But not like you can't win a single point against them. Right. Right.

[00:24:13] And so, you know, when you have three great players and one 3-5 or 3-0, it's like, you know, it's not going to be an enjoyable time for really for anybody. Right. I agree. And that goes with me. It's like, I don't need to be going out there and trying to play with, you know, Ben Johns. Right. It's just, not that he would play with people, but I'm just saying.

[00:24:36] So, but you, there is a demographic of people that are like, hey, I just want to play when I can play, when I got free time. And I think that's fine. I do too. You know, that's what you want to be. And I'm at a level where I'm not going to go out there and play six, seven times a week and drill for two hours. And I'm trying to make it onto, I guess, the senior tour. One of my shots are. But no, like, and I've had to back off a pickle a little bit with the increased business responsibilities I've had.

[00:25:06] But when I'm playing, I want to be intentional of this is what I suck at and I'm going to try and work on this even in this rec game where we're going to, you know, drill drops or dinks or whatever. And there is a mindset of, hey, I don't care. I'm just going out there to, like, blow off steam, which is totally fine. Sure. Versus I would eventually like to become a 5-0 player is sort of my vision in my head. Yeah. I think people, you know, if you can hear me when I say this, I think that there's definitely got to be a happy medium.

[00:25:34] I never want anybody to be a tool that, you know, that's at the rec courts or whatever. And I feel like, like you said, the awareness is part of the battle here. It's just truly understanding what level that you're at, what level that you're playing at, what level are playing on the particular court that you're at, and just having that kind of awareness. I do think that pickle still is one of the greatest social activities that you can absolutely do and play with any and all folks. And there are times and places that you and I do this at, you know, Laurel or other places like a pickle rage that we're at right now.

[00:26:01] But that's one of the beautiful things that I do love about facilities like this that we have behind us is they, when they're managed correctly and they have these groupings, it's very, very harmonious for the whole facility to have their court set up to where you have beginners, intermediates, advance, and then becomes not clicky. It's just based on the level of play that you're at. It has nothing to do with, you know, who that particular person is. It's all based on level. Yeah. Yeah.

[00:26:25] With that being said, as we navigate and start getting into the wonder world, I got some quick fire questions for you because I want to make sure that everybody gets a chance to hear some of this stuff. What are you chasing over the next five years, both pickle and business? Hmm. So pickleball, you know, I want to still be healthy. Okay. You know, I still want to be able to play and I want to keep like, keep my weight where it's at, keep working out, doing my stretches and strengthening exercises.

[00:26:55] Because pickle does take a toll on you if you're not doing that, whatever, physical therapy or whatever to it. So, yeah, I mean, I would hope I'd definitely be at a 5-0 level. And that's a thing. That's a thing for you is 5-0. Yeah. I want to make it there. I think I can without having to like sacrifice my whole life. Sure. And then business. Five years. Five years from now.

[00:27:25] Well, something that I'm really working on is the liquidity aspect. Okay. Right? So you've got, I've got a stable of commercial real estate that is working well and stabilized cash flowing and being paid down. Okay. That's going to continue to work. As long as I keep my eye on the ball and go forward with that.

[00:27:51] That's like the long-term horizon of when I'm 60 years old. Right. It's paid off or paid down. And then we'll see what we do with it. But, you know, my focus over the next couple of years, and one of the reasons I'm doing the flex warehouse development, is the liquidity aspect. Because for the last seven years, literally almost every dollar I've made, I've plowed into real estate. Right. You know, it's like I'm buying another this, another that. And that's fine.

[00:28:21] You know, that's good. But when you have a certain level of liquidity, you're able to make pretty bomb-proof returns to pay that base salary without having to worry about, you know, where's the next monthly check coming in from. And I'm getting some of that from the real estate, obviously. Sure.

[00:28:44] But I want to really shore up that component into the multiple seven figures. And so that's one thing. And then I want to keep doing deals that I like to do. You know, I found that what gives me joy is the thrill of the hunt. You know, the negotiations, the finding opportunities, putting the deals together, gathering the investors, and executing.

[00:29:11] You know, the ongoing day-to-day management and maintenance, that's not, like, my favorite thing. And that's why I've brought on Crystal, my sister, and Yadin, and Stacey. They helped me with that back-end maintenance of this stuff. But I want to still be doing deals. I mean, I want to still be doing deals into my 70s if I can. A hundred percent. Charleston beat the heat this summer at Pickle Rage, offering a premium indoor pickleball experience at competitive rates.

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[00:30:10] Founder pricing will not last forever. No rain delays. No summer heat. Just the best indoor pickleball experience in Charleston. Visit Pickle Rage today and secure your founder rate before it's gone. Your podcast that is unlike your life talks a lot about this kind of stuff. But if you were talking to somebody that's at the starting line, which is a scary spot for all of us, no matter what we're in, whether it's starting. You have somebody that's listening right now that's in, you know, Tampa, Florida that hasn't played pickleball that might hear this.

[00:30:39] That's entertaining playing it. Or you have somebody that's in Tampa, Florida that's really thinking about buying their first piece of real estate, whether that's commercial or you're going to buy their first house. What do you have for them to get them off that starting line, man? Just give them a little bit of bump. You know, I think people that are, quote unquote, ambitious and accomplish a lot, they focus on the outcome that they want. And they don't think about all the work and hurdles and obstacles that it's going to take to get there.

[00:31:09] The people that don't, that's what they focus on. Well, I'm going to have to do this. I'm going to have to do this. And when I talk to people and they start bringing up, well, I can't do this because of this and this and this and this. It's like they're done. They're crippled already. Like I can't. They're not going to make it. They're going to make it, but this may not be the field for them. Got it. Right.

[00:31:33] When I have 300 units paid off, you know, that's cash flowing $150,000 a month and I don't have any debt and da-da, like that'll be amazing. You know, when I have X liquidity and I'm making $500,000 a year without lifting a finger and I can travel with my wife and kids, that's going to be amazing. When they're focusing on that, it doesn't matter that this stuff is going to be really, really hard and probably the hardest thing you ever did.

[00:32:00] And there's going to be things that go wrong and banks are going to be a pain in the butt and investors are going to pull on you and on and on and on. They don't think about that. And so I would say like to really lay out and dream a little bit about what that looks like five years, 10 years down. People overestimate what they can accomplish in 12 months, but they underestimate what they can accomplish in five or 10 years. Sure.

[00:32:24] You know, what I've accomplished over five, seven years in commercial real estate is far beyond what I thought I was going to be able to do. But when I looked at the micro, it's like, oh, I'm so far behind. I'm not doing enough. And then the other thing I would say would be, I think it's important to crawl before you walk and walk before you run.

[00:32:46] You know, we've seen a lot of commercial guys going down because they grew way too fast with not enough experience, not enough liquidity. And it's hurting them. You know, they're losing properties or losing investors money. And so I think that there's no shame in, hey, I want to go out there and flip a house. I want to go out there and get a single family rental. I want to go out there and buy a mobile home and rent it out. Then I'm going to buy a quadplex.

[00:33:14] Then I'm going to buy a 12plex and a 24plex. And I'm going to grow into that. And I'm going to learn the lessons along the way. Sure. But people, they don't execute, right? It's like whatever your hand finds to do, do it. Like whatever's in front of you, that's the next step. Do it because then the next step will be revealed. Instead of just dreaming and thinking, well, I need to do this. I didn't need to do that. Like just start.

[00:33:40] You know, I went to Ohio, went to a meetup, met a guy who had built a hundred of these flex warehouses. I was like, that's a pretty good idea. When I got home, I just started looking for land. I identified a piece of land. I called the guy. He's like, oh my gosh, yeah, this will work. This is a good deal. And then I'm like, okay, well, what do we need to do next? What do we need to do? And I've started to execute and figure it out as I've gone. And I thought about, well, what's worrying me? What's bothering me about this? Well, the risk level. Okay, how do I mitigate that?

[00:34:07] Well, if you had a good bit of these pre-sold before you even broke ground and before you took the loan on, you'd probably feel better about it. Okay, let me start working on that. You know what? I'm just going to put out a Facebook ad. Sure. I don't know if I want to hire a broker and blah, blah, blah, and get an OM, but I can put up a Facebook ad and I can start talking to business owners and I can get market feedback. And people try to build something often that the market doesn't want.

[00:34:30] And they go so far down this road and by the time they produce it, it's not what the market wants it because they didn't start with a little bit of market feedback in the beginning and starting action. So that's what I would say. Dude, there's so much to unpack there and I hope you guys were paying attention to that because there's some great stuff in that. But to hit on that, man, one of the things that I love about you, and I think that you'd probably say the same thing about me that I have noticed in entrepreneurs, is the pace of play that they play at.

[00:34:57] If me and you right now had a good deal that was brought to us from whatever, somebody that's on the counter here at Pickleball Rage, it takes me and you like all of 30 seconds to go, we need to pursue that. We don't linger on it. Now, whether we choose to do it or not may be done within a minute or two, but there's no lingering. I feel like so many people at the starting line, like you said, get unindated with worry and doubt and fear of things that between you and I are never going to ever happen to begin with.

[00:35:24] But they don't even take the initial step to go over the line because all of that stuff even stopped them from taking the first initial step. I think like Pickleball is realistically the same exact thing. I feel like if you really want to get better at Pickleball, it starts today. Like it literally starts with what you're putting in your mouth right now that you're listening to this podcast. If you are 5% lighter than you were next week than you are right now, it's going to be easier for you to play Pickleball.

[00:35:47] If you'll get with a coach to learn how to do drop shots and when you need to hit the thirds and when you can learn the true how, if you did that literally today, you signed up for a $40 lesson or a $50 lesson somewhere at Pickle Rage or wherever it may be, I am telling you this time next week you would be a better Pickleball player by that one particular lesson. I can guarantee it. In real estate, it's the same exact way to where if you'll get on the internet tonight and find something that literally whets your whistle, whether it's res, whether it's a commercial, whether it's, hey, you want to be a developer, whatever it may be,

[00:36:17] you got to take the initial start to do it, which is going to require you to take the first step. And one of the things that you do better than anybody that I know is you are very quick to pull the trigger. Now, you're not quick. Be the first person to tell you this guy drives me crazy with how many T's he crosses and I's he dots. He dots it all, but he is literally going to hop in the water and then we'll figure out how to swim. And if it ain't where we want to be, then he hops out the pool. Yeah. Yeah.

[00:36:42] I mean, if you don't have a sense of urgency, you are not going to succeed in business. And then going on to that, if you're not growing, right, there are people that they get into something. It's not great. You know, I'm going to use the example of single family rentals. Like it's fine. You know, I started there. I had five or six of them.

[00:37:08] But I recognized to scale this to 100 is going to be a nightmare. It's 100 tax bills, 100 roofs, 100, you know, mortgages. And I don't want to do that. And I want to grow. I don't want to. If you want to own five or 10 rental homes and that's where you're going, that's fine. That's a great vehicle for it. But the next step is scary. You know, like multifamily. Well, that's going to be more complicated. And, okay, well, is it really like how do I learn that? Who knows how to do this stuff?

[00:37:37] Who can I connect with? Same with pickleball. It's like, yeah, the first step is just get out there and whack the ball and play around. But then, okay, who knows how to play? Who should I be coached by? What are the better players doing? You know, what are videos I can watch? How can I improve? And that's what I've tried to do with real estate is instead of just camping around like, well, I did this. It wasn't great, but it worked okay. And so my whole life, I'm just going to kind of stick with flipping houses or single family houses.

[00:38:07] It's like, are there better opportunities? Because I'll tell you that the opportunities in commercial real estate are far, far better. You know, and there's far less competition too. You know, everybody and their brother wants to flip a house or have a single family rental. And the reason why is because it's easy. It seems easy. It's like, okay, just do this. And that's why there's more people in multifamily than there are in say, like industrial real estate, because that's easier to understand. And it's like the next logical progression. And I think it's a good progression.

[00:38:36] That's the way I went. But if you're never willing to push yourself and grow and get outside of your comfort zone and learn things that you don't already know, you're not going to uncover some of the things that me and some of my colleagues have been able to do. I mean, I got a guy who he had an 80,000 square foot vacant warehouse that he put under contract for 1.2 million before they closed, they signed a lease with a new tenant at $6 a square foot

[00:39:06] and increased that building value to 3.4 million day one. Before he had even, before the inks even dry on the closing paperwork. He had that lease signed before he signed the purchase agreement. Okay. He had to put $150,000 in, you know, outfit. So his basis is like 1.4 in this deal. It's not worth 3.4. He can either put that on the market and resell it as like, hey, we got a tenant in place. It's just a coupon clipper.

[00:39:33] Or he can refinance and a bank will probably give him $2 million in cash or in refinance proceeds. And he can pay off his old loan and put $600,000 in his pocket. That doesn't happen in residential real estate. In parallel to that, though, I feel like how, how compared to that is the players of pickleball, though, that are, we'll say 4-0 and under. It's so easy for every, everybody that you talk to. Right now you're listening to this pickleball pass and I, and I was, I trust me, I've rated more people than anybody listening to this podcast right now.

[00:40:01] And I'm telling you right now, if I ask you what level of pickleball player you are, you're going to tell me you're a 4-0 player. I promise you, you won't tell me you're a 4-0 player. Let me tell you right now, you are not a 4-0 player. I promise you, you're not a 4-0 player listening to this goddamn thing. With that being said, that's what drives me crazy, though, in pickleball to where you know, without a shadow of a doubt, when you walk onto this court, what it's going to take in order for you to be a 4-0 player. And it's not going to be just showing up to the court. You have to have a plan. You've got to work. You've got to dive in. You've got to get a lesson. You've got to adjust. It's just like business.

[00:40:29] There's so many parallels to it that I love so much. But at the end of the day, if you just continue to show up at the recreational place and play with Martha and Steven and Perry, that's great. But it's not going to make you where you want to be. You can say that you're a real estate developer or that you're a business broker or that you're a flipper all day long. But until you actually legitimately do it, you are not. Same thing with being a 4-0 player. You have to actually put in the work to do it. You can't just wing yourself to being a 4-0 player. You can't. You can't do it.

[00:40:59] With that being said, hook us up with a book. I know you're a reader because leaders are readers. What's your favorite book, man? Well, I'll tell you the book I'm reading right now. I've got to hear it. Lord of the Rings. Lord of the Rings. The Two Towers. It's like this thing, right? Yeah. Well, it's... Yeah. So all I read is business books, self-help, self-improvement, nonfiction. And my wife's like, you need to read something that's enjoyable. And I'm like, why? That's stupid.

[00:41:28] Are you enjoying it? I'm enjoying it. I'm actually... I'm reading The Two Towers. I'm liking it. But it's pretty good. And I dug up Rich Dad, Poor Dad. I've never heard of everybody who talks about that. Yeah. I gave that to my son. I was like, listen, I'll give you 10 bucks if you read this book. Just read this book, yeah. So I don't give him money for grades, but I want him to read. Rich Dad, Poor Dad is a really good eye-opener of a different way to see the world.

[00:41:58] I agree with that. I feel like... I don't want to mention it because I feel like everybody knows it, but probably everybody doesn't know it. Rich Dad, Poor Dad, it's like this guy was raised by his poor dad who was... He did everything right. He went to the universities. He got the degrees. He got the job. And he's kind of just eking and scraping by. Where his friend's dad, the rich dad, owned a business, owned real estate, was doing deals,

[00:42:26] taking on some risks and succeeding at that. And just the way that he thought about things. And it's cool to see the comparison. You know, man, we can't afford that versus, well, how can I afford that? This, you know, this never works versus, well, how could it work? Having that possibility mindset to look at problems and look at the world from a different perspective. And I look at the world now where it's like money is infinite. Opportunity is infinite.

[00:42:55] And it can be created out of thin air. Like, I was there on the site with my son on Orangeburg Road, the flex site. And we're putting up the sign. Contractor sale or contractor garages for sale. And I said, Jennings, you can just do things. You can just create things. Like, we picked up a piece of land for $380,000. You know, raw land, but zoned correctly. Now we've gone through the entitlement process. It's now worth $1.2 million.

[00:43:22] We're going to build, you know, $4 or $5 million worth of buildings on it. And it's going to be worth $9.5 to $9.7 million. Like, you can do this. You can just create value out of thin air if you have the creativity and the drive and the knowledge to do that. And I think people, it's like, I've got to trade one hour or 40 hours or one year to make $50,000, $100,000. And that is the equation. And that's the only equation that they know.

[00:43:49] Whereas, they can make $100,000 in a month, you know, given the right opportunity. I love it. One of the books that I'm going to add on to that, man, is going to be a book that you all guys got to get. It's called Who Not How. If you haven't read that book, you need to get that book. I highly recommend The Rich Dad, Poor Dad, though. And I do think like, as you do, learning the differences between the mindsets for me is where it starts and stops with everything. And that's pickleball included. Do you have a favorite, like, realistically, I want to talk a little shop with you before we get you wrapped up.

[00:44:19] Right now, man, do you have like a favorite paddle? Do you have a favorite, you know, skill or drill that you can share with our people that you really feel like, I know me and you work on a lot of stuff, but is there anything that you can share with folks that you could, to help them with their pickleball game as we're wrapping this thing up? Yeah. Paddle-wise, I always had like the Yola, Hyperions, the Illegal One. That that guy gave me in Atlanta. Yeah. I don't remember. Yeah. Yeah. I don't know. Yeah.

[00:44:47] But what I found is the way my game is, I don't need more pop. I don't need more power. I don't need more put away power. I'm not playing players at that level yet. And my biggest issue was high drops and high dinks. Okay. And so I bought the, I don't even know what it is, Vanquish or Manage? Yeah. Vanguard or something. Vanguard. I don't know what it is. It was a cheap paddle. It was like 130 bucks. It's got a lot of grid on it and it's soft.

[00:45:15] I bought the 16 millimeter one. It's by Pickle, right? Is that right? Yes. P-I-K-K-L. That's right. And so I've been liking that paddle. I've been keeping the balls lower. And so I think it's kind of, where are you? You know, if you need more zip, maybe you get a loaded paddle. But most players, I think they need more control than they need power. Okay. Like the high power paddles should kind of be the last thing that you're working into once you are over 4-0.

[00:45:45] I think below that, you need a soft paddle. Because if you can just keep the ball low, dude, you're going to win way more. All you got to do is just keep the ball low. I love it. And what do you work on for this? So what do you give these guys, like tip of the day? Yeah, for drills. What would you give them? So I used to love 7-Eleven. You know, we played 7-Eleven. But what I've found is a better drill is the skinny singles. Yeah. You know, where, because in 7-Eleven, you don't have the serve. You don't have the return.

[00:46:12] And it's not as competitive as I feel like a skinny singles game is. Which is competitive, right? Yeah. So skinny singles, if you're not, you know, you're playing on half the court. You really have to control your ball placement. You got to get your returns deep. Deep angles. You're also moving back to the court. You're cross-dinking. You're forward dinking. You know, straight on dinking. You're getting the speed ups. You're getting the hands belt. You're getting everything in one drill game with two people.

[00:46:37] And I don't really love like full-on singles because I'm too old and slow for that. I get it. But the skinny singles, I feel, is a really good drill to help you improve. No, I want to add a boy on that. I think that's a great. If you guys don't know what skinny singles are, there's lots of videos on it. Maybe we'll do one. That would be great. But skinny singles is a great skill set drill that has everything that you need that we can incorporate, you know, getting you to become a better pickleball player. Well, dude, I could sit here and talk shop with you for three and a half hours. I know the people listening, too. First and foremost, thank you so much, brother, for coming on and being my 50th.

[00:47:06] That's a really big deal. I appreciate you having me. I do appreciate that much. And most importantly, guys, if you would, go on to Sean, where our producer's going to make sure he's got our link for the Unlock Your Life podcast that Jennings does. It's weekly, right? You do yours weekly? Well, I bi-weekly. You're bi-weekly as well. Slacking off. So maybe we can alternate. But yeah, he's got some great content on there. So if you enjoy Jennings and all that he's got to talk about, please make sure you check out his podcast. Hey, appreciate you guys. Coach Tommy out. We'll see you next time.