Pickleball Business Life
Based on Long Island, NY, Pickleball Business Life brings the worlds of pickleball and business together. Hosted by Rocket Rich (Richard Simanoff), a wholesale insurance broker and Pistol Pete (Pete Avella), a furniture broker, the show features conversations with people from all corners of the business world who also share a love for pickleball.
From careers and entrepreneurship to success, setbacks, controversial takes, and pickleball talk, Rocket Rich and Pistol Pete keep the conversations fun and unpredictable.
Whether you own a business, work in one, love pickleball, or just enjoy a good conversation, there’s something here for you.
New episodes drop two Fridays a month.
For guest inquiries/collabs, email pickleballbusinesslife@gmail.com
Pickleball Business Life
Episode 5: What Happens When You Quit Your Job to Open a Pickleball Facility
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Today on Pickleball Business Life, Rocket Rich and Pistol Pete sit down with Lauren Redmond from Harbor Pickleball. Lauren shares how her father's obsession with the sport pulled her in, how her media career led to an unexpected entrepreneurial pivot, and why she set out to open a pickleball facility.
Lauren brings her husband Tom and their two kids, Peyton and Brooks later in the episode. Tom shares his initial reaction to Lauren's business venture and the couple's competitive dynamics on the court. The rapid fire round gets real including a surprise question from their daughter Peyton to wrap things up. Lauren also opens up about her brother Brian, who was diagnosed with early onset Parkinson's at 28 and remains her biggest inspiration.
You can find Harbor Pickleball on Instagram @harborpickleball, Facebook @harborpickleball, and their website harborpickleballli.com. They are located in Commack, Long Island, NY.
Find Pickleball Business Life on all podcast platforms, Instagram @pickleballbusinesslife, TikTok @pickleballbusinesslife, and YouTube @pickleballbusinesslife.
For inquiries, email us at pickleballbusinesslife@gmail.com.
Everybody would kind of laugh it off and they'd be like, yeah, Lauren, you have a successful career. Like you're not gonna open a pickleball facility.
SPEAKER_04Okay, we are here now with Lauren Redmond from Harbor Pickleball in Comac. And uh let's start Hey Lauren, how you doing today?
SPEAKER_00Good. Thanks for having me.
SPEAKER_03Yeah, we've been waiting for you to come on, and here it is. Here we are. Very excited.
SPEAKER_04Very excited. So how'd you get hooked to pickleball?
SPEAKER_01So my dad was playing this weird sport called pickleball all the time. Couldn't get him on the phone. So when my husband and I went down to Florida, we were like, What is this, what is this pickleball that you're playing? Show us. And we went and we played. And Tom, my husband and I are very competitive with each other. And he wanted to get me into golf, but he's been playing golf since he was young. I'm like, I'm not, I'm not built for golf. Okay. But we tried pickleball, and it was something that we were both starting at the same time together, and we became hooked. We started How long ago was that?
SPEAKER_03A couple of years ago?
SPEAKER_01A couple of years ago, probably I don't know, three, four years ago, maybe four years ago. And then it became like, all right, you take the kids to swim, and I'm gonna go down to the park and play, and we'll meet at the park and we'll switch, and then you play, and and it kind of just escalated from there to put it mildly.
SPEAKER_04Got it. Wow. That's interesting. I didn't realize that your father is the one that got you hooked to pickleball.
SPEAKER_01Oh yeah. He's big, big into pickleball, you know, spends half his time here. You know, my parents are halftime here, halftime in Florida. When he's up here, it's like the offseason. When he's in Florida, he plays every single day, and he's a good player. Oh, yeah, we're sure. We saw his name's Rich.
SPEAKER_03We just met him and we played with him, and he's a solid player and a really nice man. Well part of Florida. Yeah.
SPEAKER_01They live on the Gulf side, on the Gulf Coast. Uh-huh.
SPEAKER_03West side, right?
SPEAKER_01Yeah. It's in between Tampa and Orlando. It's called Fernando.
SPEAKER_03Oh, okay.
SPEAKER_01I mean, I get why they love it. We my brother and I say it's like them, they're at camp. Like we can never get them on the phone. They're doing pickleball, golf, they're going out to trivia night. So, like a lot of what they do in Florida was the inspiration behind programming and things, like social aspects of Harbor.
SPEAKER_04God, it's so what made you decide to open up Harbor or become a you know to start this business? Harbor. Yeah.
SPEAKER_01Um, well, like everybody else, I was playing at the local parks. I used to play at Terry Farrell Park every day that my schedule would allow. And um I was commuting into the city, and I have two young kids, and I was going to Pickle and Parr in Smithtown, and you know, you'd lose an hour, you know, 25-30 minutes going there, 25-30 minutes coming back. And at the time there were no other facilities. So I just sensed that there was really a local need to have a facility that wasn't a multi-purpose facility, that wasn't tennis courts that were converted or on basketball courts. And um, you know, just from living around here and then talking to everybody that I played with, and they were like, Yeah, we need a place locally, essentially located, dedicated pickleball facility.
SPEAKER_04Got it. So since you've been open, is there anything that has surprised you about running a business? Running a pickleball, pickleball business?
SPEAKER_01I never thought the community would be as supportive as they are. I am just so taken aback. Like I thought, you know, my friends would be supportive and everything, but there's, you know, so many people that I've met doing this venture that really don't know me at all. And the way that they come in and greet me and the feedback that they give me is just I'm really blown away by it. Like I like everybody acts like I'm their best friend, and we go way back and they want to, you know, welcome me and protect me and give me advice, and it's just it's really heartwarming. Like I love it. That's wonderful.
SPEAKER_03And we're part of your pickleball family. I know you're building this beautiful pickleball family, and we like the feel of your club. It's in Cormac, and we just you know like the whole passion of behind it when we walk in there. We feel good.
SPEAKER_01Well, you guys are included in that. When I say that, you know, I didn't know you guys before I opened this place, before I opened Harbour.
SPEAKER_03You have a very big family feel there. Yeah, yeah, absolutely. Absolutely. It's great. Well, yes, it's great. Yeah, sure. Next question, um, uh, what makes Harbor pickleball different from other pickleball clubs in your eyes? I think we talked about that a little, but can elaborate a little bit.
SPEAKER_01Well, I just wanted it to be, you know, good quality pickleball first and foremost. So I really paid attention, you know, when designing the facility, that we did it right, that we had proper spacing on the courts. Because what it's always such a letdown for a place to say they have X amount of courts, and then you go there to play, and you know, there there's no room on the side, or you know, it's just not what you would say.
SPEAKER_03It's a spacious layout.
SPEAKER_01How many courts do you have? Seven. Seven. We have seven quartz. And then the other thing is everybody always wants to play as much pickleball as their schedule, bodies, and wallets will allow. So for me, it was a no-brainer to do the pro-cushion quartz. The pro-cushion quartz, you know, absorbs the impact on the body, lets you play longer without feeling as fatigued. So that to me was like we need to invest in top quality quartz that just make the impact less on people's bodies. So that was a big part of it. And then, you know, kind of selfishly as a pickleball player, I was like, what do I love? I love the social aspect of it. So I want a place that is the cheers of pickleball. Oh, I love that.
SPEAKER_03I like that. Great analogy. Great analogy, super analogy. Oh, I like the way you set up the area, the dining area, and the way you have all the taps set up with the different drinks and everything. Tell us a little bit about that. The cheers of pickleball. It's like a built-in you know, greeting area there, bar, a little bit of everything. And it's just laid out really nice. Thank you.
SPEAKER_00Yeah, I wanted everybody to walk in and be like, oh, there's my friend, you know, Rocket Rich and Pistol Pete. Like, let me go say hello. Let's grab a beer, you know.
SPEAKER_03We noticed there's a lot of camaraderie there. I mean, it like you said, because you've created that environment for that camaraderie with everybody. It's like and again, it's I'll say it again, it's like a pickleball family. I'm watching it build before our eyes each week when we come in. We we have the group that plays on Thursday nights, and then Sunday mornings are great, and it's just a great way to finish off the weekend, especially on Sunday mornings, is to get up and go there, and I think you're building your clientele really nicely from what we've seen, right, Rich? I agree. 100%.
SPEAKER_04I I can definitely see it from the day I first came. I mean, you know, you could see how things have grown, and I literally love the cheers analogy. Really, I I asked you feel that way there. So it's really kind of funny.
SPEAKER_03We love playing with your husband Tom. And not just that, yeah. And he, you know, he'll be on in a little bit. I mean, it's just great. It's great. Your kids are always there. It's a real family-oriented place that you know has a great foundation, we see.
SPEAKER_00Thank you. I appreciate it.
SPEAKER_03Really mean it. And look at this little cutie pie, Peyton. Peyton, how old are you?
unknownSeven.
SPEAKER_03Seven, wow. And this is Brooks, right? And Brooks. Son Brooks. And how Brooks, how old are you? How old are you, Brooks? Wow, what a great family. Cool, cool. You got a great mommy and daddy, right? You enjoy being around the whole pickleball uh atmosphere. Uh oh, thanks, baby. This is wonderful.
SPEAKER_04So, where do you see pickleball five years from now and in the business in general? I mean, there's definitely becoming, there's definitely getting more competitive out there, more and more places are starting to open up. What do you where do you see like the saturation of the clubs and the competition? Where do you see it going?
SPEAKER_03On Long Island, right? We have five million people here. So it's like a lot of people.
SPEAKER_01I mean, I think it's just gonna continue to grow. I know that you know it feels like it's getting saturated, but there's still so many people that haven't experienced pickleball yet. And the amazing thing about pickleball is the word of mouth. So somebody plays and then they go and tell their friends how much they enjoy it, and then they hear it from other friends, and at a certain point, it just can't be denied. Everybody's like, all right, let me check out that's 100% true sport that everybody's playing, no matter what their age, demographic. So I think it's gonna continue to grow. Um, I think the quality of the facility is gonna become more and more important because again, like people just want to play and they want to play as often as they can, and they want to go to places that you know, check all the boxes for them. And it might be different, you know. Some people might just care about how often they can play and budget. Other people, I mean, I find a lot of people care about the social aspect. So um, I feel like there's a lot of facilities are gonna kind of find their, you know, niche, there, have their drawer to kind of differentiate themselves, where at a certain point, you know, it was just people opening pickleball facilities who knew nothing about pickleball. And I think that some of those facilities have been struggling because they don't understand what makes pickleball so great and what the huge appeal is. So um I think it'll continue to grow, but I think facilities will continue to morph to speak to the different audiences.
SPEAKER_04Got it. Great answer. Yeah, great. We talked about this briefly, but why don't you just, you know, that way you have enough people on now that can hear. What were you doing before Harbor?
SPEAKER_01So I worked in media for about 25 years. Um, I started as a graphic designer, animator. I designed the Harbor logo is my handiwork.
SPEAKER_03Love it, right?
SPEAKER_01Yep. Um I worked in news. Um, I had a creative content team, and um, and it was animators, branders, video editors, producers, um, I had a promos department, and um, I had a fantastic, fantastic team. Um, but it was I I loved what I did. It was a grind. It was a grind every day. And and after having kids, as tends to happen, and commuting to the city every day, you know, you kind of ask yourself, can I do this for the rest of my life? You know, do I want to do this for the rest of my life? And for me, the answer was always no. Like, there's gotta be something more sustainable. There's gotta be something that brings more fulfillment to me. And as I was doing that every day, and on paper, it looked like, you know, I've made it, I have all the things. I started telling my coworkers at the time, you know, that I would love to open a pickleball facility. And everybody would kind of laugh it off and they'd be like, Yeah, Lauren, you have a successful career. Like, you're not gonna open a pickleball facility. And here I am.
SPEAKER_06Here you are.
SPEAKER_04You are here you are. Here you are. You know, listen, you know, if Ellie ever quits, we can also maybe hire her part-time to run.
SPEAKER_03I mean, with her expensive, I mean definitely, or you can join them up as a team, both of them.
SPEAKER_04Yeah, maybe. I don't, yeah, that's right. She's busy right now.
SPEAKER_03So you're not still grinding to the city like now? You've leave that. Okay, so now your new focus is harbor. All in on harbor.
SPEAKER_04Fall in on harbor Manhattan, no more grind.
SPEAKER_01What's your what's been your proudest moments so far in the short time you've been open as far as harbor's concerned, as far as uh well, I mean, we opened during the start of the slow season.
SPEAKER_00Okay.
SPEAKER_01So, you know, everybody again like embracing me and like welcoming, you know, myself, my partners, the facility into the community. Everybody was like, you know, I'm worried for you. This is the beginning of the slow season where people go outside and like prepare to struggle. And you kind of touched on it a little bit, Rich, but like week after week, even without having any data, like you just feel it in there. You just feel it get busier and busier, and like the the slow times are no longer as slow. And and it's it's that, and like word is getting out, but it's just also for me the most fulfilling thing is how much everybody's enjoying it, like, and everybody is so vocal, and that's the thing about pickleball players. Like, all you have to do is listen, they tell you exactly what they want and what they don't want.
SPEAKER_03Yep, and you have a good vibe in that place. You really I'm not just saying it, you really have a great vibe, and we enjoy it. Oh, yeah, totally.
SPEAKER_01I just feel like life is tough enough. Like there's enough hard, sad things that go on in life. Like, this shouldn't be that. So I just want everybody to really enjoy themselves and have a good time when they come visit us at Harbor. Yep.
SPEAKER_03Sports feel good therapy at Harbor. Yeah, we have some rapid fire questions for you. Are you an early bird or are you a night owl?
SPEAKER_01Early bird.
SPEAKER_03Yeah, like real early.
SPEAKER_04You gotta choose. Yes, she's definitely an early bird, but like I mean, I know you also you're also, yeah, you're out there at night too. You're closing the place down at times, stuff like that. But what are you, what's your preference if you had to choose early bird? You're more of you're more of an early bird than a night owl.
SPEAKER_01Well, working in news the last 20 plus years, I was waking up at 3 a.m. to commute to the city. Right. So that kind of gets in your blood. But I I don't know, there's something about the mornings and the quiet and like getting a jump on the day. I feel like my mind is so clear. I just I I love that.
SPEAKER_04I love the mornings. Cool. So what other passage do you have besides pickleball?
SPEAKER_01Um interesting. I just you know, it's it's tough because you kind of lose yourself like when you become a mom and you throw yourself into your family and everything. So I'm just really getting back to basics and like what makes me happy and what makes my family happy, you know, and and I do enjoy, you know, design and photography and those kind of things. But I also I I enjoy, you know, anything social. Like I'm just I feel like I was kind of lost in like motherhood for a while and like really devoted to my career. So um, you know, as a as a mom, as a woman, I think you kind of lose yourself in that. And now I feel like I'm back better than ever, and I'm kind of like I'm living my best life right now. Like I've never been happier.
SPEAKER_04Yeah, I think that that's great. You said for a lot of people that play pickleball and that run pickleball facilities. I totally agree. Why don't you ask the next story?
SPEAKER_03Definitely. Uh favorite post-game meal after playing a lot of pickleball against your husband. I just came up with a name for him, Tenacious Tom.
SPEAKER_06Double T. That guy is amazing. Tenacious Tom. I like that. Kudos to him.
SPEAKER_03We're having him on soon. So after playing with your husband or playing in a good game, what's your favorite post-game meal?
SPEAKER_01Can I drink my meal?
SPEAKER_03I love a liquid beer. Yeah, there you go.
SPEAKER_01I love a cold, ice cold beer after playing. I mean, the the alcohol part of Harbor.
SPEAKER_03Yeah. Um Six Harbor's brewing. Yeah, there we go.
SPEAKER_01This is what more and like a partnership with Six Harbor. Yeah. Mark has been absolutely fantastic to us.
SPEAKER_04Okay.
SPEAKER_01Um, yeah, I feel like, you know, after playing, and you know, you're a little dehydrated, you can only drink so much water at a certain point.
SPEAKER_06It's true.
SPEAKER_01Just nothing tastes better than that first sip of an ice cold beer. But for those who don't like beer, we have cocktails and wine too.
SPEAKER_03That's right. That's right. That's great.
SPEAKER_04Rich, next question. Who would you say has inspired you the most in life?
SPEAKER_01I mean, a huge inspiration to me is my brother. Okay. So my brother is two years older than me. Okay. He was diagnosed with early onset Parkinson's at 28. And he just doesn't let it stop him. He doesn't give up. He's never in a bad mood. He just every day is just happy and positive. And he was a huge supporter of this endeavor and really of me. And a sounding board when things were tough and really um, you know, stuck by my side the whole way. And like there's he has so many reasons to be in a bad mood and to just really feel bad for himself, and I've never seen him feel bad for himself.
SPEAKER_03He overcomes that. Yeah.
SPEAKER_01He just, and I mean, he's a spokesperson for the Michael J. Fox Foundation.
SPEAKER_03How old is he today? He said 28 was when he was diagnosed.
SPEAKER_01He's 46.
SPEAKER_0346. Wow.
SPEAKER_01He's 46. What's his name? Brian Roberts. And hi Brian.
SPEAKER_03Brian.
SPEAKER_06Wow.
SPEAKER_01He just doesn't let it stop him. And he's just got great drive. Positive force. Yeah. Um, so yeah, my brother, for sure, without a doubt.
SPEAKER_04Now we are joined by Lauren's husband, Tom. That's who that young man is. Yes, exactly. We've been talking about him. Yeah, we've been and we've been practicing these questions. I I can't wait to ask each of them. Me, you know. I am like really excited. All right, here we go. All right, Tom. Yes, sir. First off, when Lauren told you, or maybe you decided to get him, but I'm gonna assume this was more of a Lauren thing. When Lauren said she was interested in opening up Arbor Pickleball, what was your reaction?
SPEAKER_05Your initial reaction.
SPEAKER_04Your reaction, sorry, your initial reaction.
SPEAKER_05I was so happy for her.
SPEAKER_03But she just come one night and paint the picture.
SPEAKER_05That was uh listen, it it uh it took me some time to accept. Okay. And uh I'm I'm typically a a risk-adverse person. So it was something new for me to I kind of had a sneaking suspicion something was going on. Okay. And then when it finally when the truth finally came out. In fact, I remember a conversation that I was having. I was driving down the LIE and I was having with somebody I work with, and I said, I don't know what she's up to. And I just remember saying to him, it better not be a pickleball place. Sure, I had some intuition that was telling me. Okay. That's funny. All right.
SPEAKER_01I don't think Tom realized at the point like how determined I can be when I set my mind to something. And I think he was hoping that I wasn't gonna be so determined about this, but like my career was established before I met Tom. So I don't think he really saw this side of me, you know, in its full glory before. Like my parents weren't surprised, or like, you know, I've had the same one of the same best friends since grade school. She was like, I knew that, like, come on, Tom, you knew that this was gonna happen. Um, so I think he was just hoping it wasn't, and then it was like, okay, come on.
SPEAKER_03You were happy. You were right, Tom? You were like, hey, this is this is good stuff.
SPEAKER_04Exactly, yeah, yeah, 100%. All right, cool. All right, you can ask the next question. But this is the one, this is the one to ask, ask this one right here.
SPEAKER_03Yeah, this is this is for Lauren.
SPEAKER_04No, this is for Tom. Do it for Tom. Do the one that do the other one.
SPEAKER_03Tom, what's the one pickleball habit that drives you absolutely crazy when you're playing with your wife, Lauren? You gotta think about this for a while. Dig in.
SPEAKER_01I'm perfect.
SPEAKER_03What drives you nuts when you're playing with her? You're playing with her, and what just makes you go bonkers?
SPEAKER_01Playing with me, probably.
SPEAKER_05I I've got to always be careful. I can't cr if I cross that center line, I'm in trouble. And uh and I'm a big guy, I've got long arms, so I should be able to I should be able to go get go get some balls with my forehand. There you go.
SPEAKER_01Right. Yeah, when you're 6'5, every ball is yours. Like I'm just gonna go over here and sit down.
SPEAKER_03So basically, you think that she encroaches on your big reach?
SPEAKER_05I mean, like what she has Lauren is very sensitive to me encroaching on her. And that's what drives me nuts. Because I have to constantly be concerned that I'm I'm I'm going a little too far.
SPEAKER_04Okay. Okay, so Lauren, what bothers you the most? Habit what with Tom when you play with Tom? What's the one habit that he does that annoys you?
SPEAKER_01In the same vein. Same thing.
SPEAKER_04He just is just like there's nothing in.
SPEAKER_01Every ball is Tom's ball until he mishits it or something, and then it's my fault.
SPEAKER_00So truth's out, Tom.
SPEAKER_04All right, there we go. There we go.
SPEAKER_05Love it. All right. Love it. Tom, I know you're a big beer guy. What's your favorite beer? Oh, help me think about this for a few minutes. Um, Miller Light. Miller Light. Yeah, I think. 100%. So I told Lauren I saw in the refrigerator. 100%. Home of the $5 Miller Lights. And then second is Six Harbors. Six Harbors Brewery. Mark makes some of the greatest beer on Long Island. Cool. Lauren, do you have a favorite beer or wine?
SPEAKER_01I mean, Tom like has this like force, like this like gravitational pulse.
SPEAKER_04I'm asking her the question, and she's talking about Tom. I don't know.
SPEAKER_01Tom, like Tom, like I was never like a big beer drinker, but now I enjoy Miller Light. Like I do. I enjoy um, I do enjoy Six Harbors um Blood Orange. Um, yes, thank you. You're welcome.
SPEAKER_03Thanks for bringing the beers.
SPEAKER_01I mean, if you know me. you know I'm always cold so in the winter I prefer red wine okay and from the Napa Valley region. Okay yeah yeah yeah yeah just had that nice wine tasting last week and that was a great event yes yes enjoyed that yeah all right so this is a question we'll start with Tom dream dream celebrity dream female celebrity pickleball partner who would it be who would it be if you had to choose a dream celebrity dream celebrity female partner I um I'd have never thought about that it could be anybody a Hollywood star or a celebrity okay so we can let's go to Lauren then okay Lauren dream celebrity male pickleball partner I mean I feel like I'm gonna be so basic here but like Ben Johns like he just seems like when he plays with Annalie like they're good at communicating they work well together like he's not too dominant of the court you know um if you saw she she sort of entree you into that with the hand holding I'm I'm I'm I'm I'm numb to it immune to it all right all right so there there you go that's basic but good okay okay so it could be anybody it doesn't have to be it could be anybody it could be an actress it could be uh who would I pick who if she was somebody that laughed at all your jokes oh my mother and here's the Redmond family and Peyton is gonna ask mom and dad a question.
SPEAKER_02Final question I try would you before we leave the kitchen tell us one more thing you're you've never admitted on a pickleball court perfect mommy you're first you're first I've never admitted yeah on a pickleball court yeah I mean it doesn't matter who I'm playing like I always get butterflies before I play.
SPEAKER_03Okay like always wow that's pretty cool to say yeah yeah it doesn't matter I always get like a little little bit of the jitters a little bit of the nerves that like you know even when you play with even when you play with Toms with him still butterflies in the belly yeah no I do I do because I just you know because you're competitive and it's competitive um but yeah that's that's my thing I come here baby um I always get I always get the jitters before I play no matter no matter who I'm playing with thank you thank you Tom um look at a smile on it come on Tom tell us one thing you've never admitted on the pickleball court question from your daughter do you know she never gets the jitters I'm an open book but uh I I would say I I've I don't know something I've never admitted on the pickleball court yes um I've pretty much admitted to everything um when you hit the ball hard you hit the ball hard you hit the ball hard you hit the ball hard I've hit it at people on purpose before wow okay there we go I know last week when you hit me I told it all it was I totally know it was and I hit you back in the chest afterwards totally yeah I I got you know totally an accident maybe a little subconscious I don't know but I was nervous to tell Lauren I don't want to take her customers not customers and and you were concerned and you stopped the play even said oh Pete go home and ice that thing and I was okay everything was good. I still didn't let you in though it was awesome you didn't we are competitive people here this is the Harbor Pickleball Club Premier Pickleball Club in Comac. Absolutely we loved having the Redmond family on this is like iconic American family right here we love it there we go exactly thanks for being on the show thank you for having me definitely this was awesome