Island Pickle - Interview w/ Owner Bill Russell

What happens when a chance conversation leads to one of Cape Cod's most unique new businesses?

In this episode of Monkey Business Radio, Chris Collins and Dennis "Bobby Downspout" Siggins sit down with Bill Russell, founder of Island Pickle in Mashpee. What began as a vision for Cape Cod's first dedicated indoor pickleball facility has quickly evolved into something much bigger—a destination built around community, entertainment, great food, and unforgettable experiences.

Bill shares how three decades in the corporate world, combined with years in the restaurant industry, prepared him to take a leap into entrepreneurship. Together, the conversation explores what it takes to launch a 37,000-square-foot startup, the importance of branding and marketing, learning from early mistakes, and why the best businesses never stop evolving.

Along the way, you'll hear discussions about building a regional brand, creating customer experiences that keep people coming back, and why successful entrepreneurs are willing to adapt their vision as they grow.

Whether you're a business owner, an aspiring entrepreneur, or simply someone who enjoys hearing the stories behind successful local businesses, this episode is packed with practical insights and inspiration.

In this episode:

• The story behind Island Pickle and its unexpected beginnings
• Why entrepreneurship is often built on opportunity and preparation
• Branding, marketing, and building awareness from day one
• Creating a destination instead of just another business
• Lessons learned during the first year of a major startup
• The power of community in building a lasting business

Transcript

Cold Open And Island Pickle

Chris 0:02

Every so often on Monkey Business Radio, we sit down with the business owners. We're building something unique in the communities where we live and work. Today we welcome Bill Russell, founder of Island Pickle and Matchpick, home to Cape Cod's first dedicated indoor pickleball facility. As you're here today, Island Pickle has become much more than just a place to play pickleball. Bill shares the story of launching a 37,000 square foot destination from the ground up, how a chance conversation led to an entirely new business venture, and why building a successful small business is about creating a community, not just simply opening your doors. Whether you're a business owner, an entrepreneur, or someone who appreciates the people investing in our communities, there's a lot to take away from this conversation. So grab a cup of coffee, sit back, relax, and welcome to Monkey Business Radio. Hello

Hosts Welcome And First Impressions

Chris 0:54

everyone. Welcome to Monkey Business Radio. I'm Chris Collins, and as always, I'm here with my good friend and business partner, Dennis Siggins of the Cape Cod Kedder Monkeys. Or as you may know him on the Cape and the Islands, Bobby Downspout. Hello, Bobby. Chris, how are you doing? Good, good. What's happening today?

Dennis 1:11

Hot day out there today. Yeah. Maybe a warm way.

Chris 1:13

In traffic. Coming over the bridge.

Dennis 1:16

Yeah. I had to run over to Rhode Island and pick up an order of supplies. And um coming back was interesting. Hey, we have uh a really good friend and neighbor here uh in the Mashpee um business community, pickleball Bill. Bill Russell's here. How are you doing, Bill? Good morning, guys. I'm doing great.

Bill 1:35

Thanks for having me over to your complex.

Dennis 1:38

Uh Bill has built the first indoor pickleball facility on Cape Cod that focuses specifically on pickleball per se. Um I first got to know Bill about seven or eight months ago when they opened up Island Pickle here in Mashby. And we went on a Friday afternoon and we had dinner and geez, it was the best burger I'd had in a long time. Um what's up with that, Bill?

Bill 2:07

Well, I gotta tell you that uh we're proud of everything we do, and we can start in the restaurant and in the kitchen. Um our exec chef just won uh American Culinary Federation Chef of the Year for Cape and Islands in the month of May. And that I read that it's a testament to how good the quality is of the food. Oh my gosh, yeah. And you know, our goal was to create a restaurant that was much more than the complex that it sat in, and I think we do that. And the hardest part of our journey right now is to convince uh people who've never come that we're not a pickleball facility, we're a social club that has a whole variety of things that we offer, and the food is top-notch.

Dennis 2:50

I don't play pickleball, and I know you also have simulated golf. I don't golf, but you know I've been into your I I go over there at least once a month, maybe twice a month. When I have people come on the cake, I take them over to your place to have a burger, it's that good. Your restaurant is so much better than what I would have expected out of a pickleball slash simulated golf facility. The restaurant stands on its own.

Bill 3:18

It really does. Thank you. And and we're proud of that. And and it's it's everything down to the you know, the environment you sit in. The vibe is very cool, right? It's an island vibe. Yeah, it is. Island pickle is the name of the facility, and it's not Capon Islands, it's actually Bahamian. It's specifically Ixuma Island. And so, you know, we started this with your discussion of driving to Rhode Island. I hate going over the bridge, and I hate going over the bridge because of the traffic, and I used to do it all the time. And now um I created our own island so that I don't have to go over that bridge to get to a cool vibe and enjoy myself in a great environment. And uh so that that's it's we'll we'll talk about all the things that it is in the in the next uh few minutes here.

The Serendipity Behind The Idea

Chris 4:01

Yeah, let's let's kind of start though. I I'm really curious. Um you've been uh in the restaurant business for a while on the Cape, is that correct? It is.

Bill 4:08

My most immediate past.

Chris 4:10

Yeah. Yeah. So um I'm kind of curious of how you ended up in a pickleball facility and not some other sort of thing with a restaurant built around it.

Bill 4:19

Yeah, so uh the short word is serendipity. Um in January 2023, I'm a Rotarian and uh we had a development company come in to talk to us about what they were going to do on Route 132 at the Kmart Plaza. And one of the Rotarians that was there was a huge pickleball uh fan at the time, and he jokingly said, Hey, where's the pickleball going? to the people developing uh the Kmart Plaza. And then he pointed over at me and he said, That guy over there should run it. And so I I hadn't played and didn't know anything about the sport. Even to today, I don't play. The last time I actually swung a paddle at a ball was Christmas Day. Wow. And uh but I'm a I'm a business guy by by uh trade. And uh thirty years before I was a restauranteer, I I was a corporate guy for 30 years and did a whole bunch of things. And uh Well, that sounds familiar here at the Gutter Monkeys, huh? Yeah, so you combine you know corporate experience with restaurant experience, and then you can put a business plan together around anything. And that's basically the genesis of Island Pickle.

Chris 5:24

Wow, that resonates a lot here because uh if you look around the room or look around this building, it was a bunch of corporate rejects or not rejects, but offshoots or whatever from uh from that world. So if you're gonna work hard, you might as well do it for yourself. That's right. That's our whole thing here. Yep, build real wealth through business ownership and uh yeah.

Dennis 5:42

Okay. So, Bill, you when did you open? Uh November?

Bill 5:45

Yeah, November, uh Thanksgiving week, November 26th.

Dennis 5:48

Okay, perfect. All right. Which for us over here is is our busy season, but I know we made a point of getting over there. We go seven days a week, you know, in November, December. We're so busy. And we were all just too tired to cook one night. And you had been open about a week or two, and we went over, and my partner, Andy, Bruce, a bunch of us, and I gotta tell you, Andy and I were blown away by that first burger we had there. And your chef happened to be around, and he came out and I called him over and I I complimented him on that. And honestly, and your potato chips, oh my gosh, they're off the charts. And we go back there once or twice. I personally go back there once or twice a month. It's a great place to eat. I love the atmosphere. I love watching people play pickleball even though I don't play. Yeah, I don't care, it's different. A lot of the bars you go into or the sports clubs you go into, you got 11 televisions on the wall, and they're all going, but your place is different. I'm watching live entertainment right there in front of me. And even though I don't know the rules of pickleball, it's kind of fun. It's different.

Bill 6:54

Yeah, you know, we set the tavern up to be the nucleus of the facility, and it's become so much more than that uh in the months that followed. But you can sit there and and watch the sport of pickleball as you described through, you know, basically sound mitigating windows, so you don't hear the sport. Not at all. You get to watch and you can listen to the live band that's playing four nights a week, or you can listen to the t television. I mean, we have 42 of them. Um they're all large screen TVs, but and if it's it's you know uh uh the the World Cup right now. So we have watch parties for all these games that go on, and we broadcast the the audio live in the in the tavern. But we're also to have two golf simulators that are adjacent to the tavern, so you can watch guys play golf as well.

Going All In On The Facility

Bill 7:40

Um in total, there's six trackman golf simulators and ten indoor pickleball courts with uh an outdoor patio that's 3,600 square feet. There's 70 seats in the on the outdoor patio with its own separate bar.

Chris 7:52

It's a big place. Yeah, I'm impressed because you went all in on this. And if you go over and take a look at this building, it's an enormous building. How big building? It's just under 37,000 square feet. Okay. What is this Gotamukey building?

Dennis 8:04

It's got ground floor 7,400. Uh the mezzanine is 4,000 or something. This building is three or four times the size of our building. Yeah, that's incredible. It's it's beautiful.

Chris 8:18

Could it give you any pause taking a leap that big? I mean, that's a big leap. I mean, you didn't just open a small bar and put a pickleball cord on the side of it out in the backyard and stuff. Uh go big or go home.

Dennis 8:28

You gotta go on.

Chris 8:29

Yeah.

Bill 8:31

How did you research it? How did you figure it out? Thousands of hours of research. I was, like I said, I had some unique historical skill sets and uh so I didn't take it lightly and I didn't venture into it you know, s you know, with without a significant amount of study and looked at the trends of the game of sp of pickleball, the demographics of the geography in the area, um what what the you know restaurant den what restaurant density is compared and believe it or not, the density of restaurants on Cape Cod is is no different than the restaurant density of Suffolk County, which is 4.9 million people. So we can actually afford it's 310 people per 310 residents per restaurant. Wow. And and so the the the location can afford another restaurant. The um there is not a uh an abundance of true sports taverns where you can go and get immersed in s the s sports on the televisions, and I created that. And yeah, it was all in. Trackman is the state-of-the-art simulator for for uh for golf simulation. Um our court surfaces are and the way we set up the courts in and of themselves are world-class. And uh I don't say that boastingly, I say it, you know, practically. And and if for those people who come and keep coming back, it's because everything we do from the quality of that burger we talked about to the quality of the surfaces and the pickleball courts is done to the best of my ability.

Chris 10:04

Yeah. Yeah. It's really impressive. I

Pickleball Demographics And Youth Growth

Chris 10:06

was kind of, we've gone over just before the show, talking about some of the demographics, and I figured, you know, oh, the cape, uh, pickleball is an elderly sport, a lot of elderly people are playing it, older people are playing it. And I looked at demographics and it's not true at all. And in fact, we were talking before the show, one of the fastest growing diet uh demographics is under 17 because of the schools are implementing it and uh things like that. And I was really impressed with that. And you threw out some numbers that surprised me as well. Yeah, you know, it's uh it's a varsity sport in high schools in two states already.

Bill 10:36

It's incredible. Pickleball is it's a it's I can see it, but that makes perfect sense. It's a sanctioned league sport, which means it's not uh varsity level, but it's a club sport in high schools, including Massachusetts, Santa Massachusetts and Western Mass has leagues for pickleball. Uh colleges are starting to introduce it as a collegiate sport. It's on the ballot for 2032 Olympics as an Olympic sport. And you know, pickleball television is on TV, and and a lot of the drive of the younger kids is uh the result of the number one player in the world turned 19 in in uh January of this year. And she's been the number one player for the last three years. You know, so and Larry. So we see it, but it's our demographic here is definitely skewed right into the you know mid to late 50s. Uh there's a lot of kids. We try to introduce youth play in various capacities, and we see more and more of it, but it's it's uh our focus is on the under-35 market in terms of growth because the growth potential is definitely there. Yeah. And we want to provide the schools an opportunity to come play either formally or informally. And it's just a lot of motion to make those things happen. And now that we're in the holiday summer break, you know, we'll get we'll we'll get our thoughts together and when we get back to the fall, we'll talk to the ADs and the superintendents and the principals around here to see what we can do, you know, either formally or informally with the schools in the upper Cape Region.

Chris 12:04

Yeah, yeah, just like hockey ranks or whatever ballparks you can end up sponsoring or not sponsoring, but hold hosting uh a school or a high school or something like that. Do you do a summer camp or anything for kids or something like that?

Bill 12:16

We we uh we missed it this year. Yeah, we had a lot of moving parts. We will, and we had a lot of debate because we have a a PGA pro uh for golf, he's a 25-year vet. Uh, he got really ill for a while and he's back now. And we have two or um we have three professional um instructors for pickleball. And the the debate we were having was you know, if putting a clinic together for an hour doesn't advantage a parent, you know, in the summer for having their kids learn something. You you gotta put together a half day or a three-quarter day session so that it's meaningful for the kids, but also for the parents. And and we just didn't get there before the summer approached us. So I I think we're gonna still work on getting some some short clinics together for the second half of the summer. I mean, it's July 1st today, right? So and and then uh as we enter into the school year, have better use of the school vacation weeks and then really hit the hard ground for clinics from for kids' clock clinics uh next summer.

Chris 13:15

Yeah, it's interesting. And I noticed uh one of the things I was kind of impressed

Memberships Events And Community Nights

Chris 13:18

with. I liked your idea up there, you've got uh memberships, quite a different array of them. So you if you're into golf or into pickleball, or you just want to come and have a social scene, it's all there for you, and under under your membership program.

Bill 13:30

Yeah, you know, the if we had had this conversation six months ago, I would have been telling you all about how it's a pickleball facility and and and we also do golf. And but but it's so much different than that today. It is we do, you know, so many events. It's a community club. In fact, we did a marketing rebranding. We we just relaunched our website literally this week. And if you go to that website today, you'll see everything that we do. And it includes a number of events that are centered around that nucleus, the tavern that I spoke of. And we do lion dancing on Monday nights, we do cornell tournaments on Tuesday nights, we do mahjong once a month, we'll do um pitch night on Thursday nights and cribbage night on Monday nights. Oh, cool. And cool. And we have you know weekly specials in the tavern for food. And the the uh the pinnacle of our food specials is Thursday night's prime rib. And we've had over a dozen people tell us that's the best prime rib they've ever eaten. And so it's also incredible. The quality of the experience in the tavern, and and then that spreads out to the quality of the experience for everything else that happens in the club. Wow.

Dennis 14:37

If there's one thing that has sustained me, and I have a little bit of a history like you, and the uh no corporate world in my history, but I I owned a restaurant, I've owned a few different businesses. One thing is marketing. Marketing, marketing, marketing. Marketing puts fannies in the seat, and that's what we all want. My younger brother lives in Virginia, but he has a home here in uh Harwick, and they're here for the summer. He called me around Christmas time, and he was asking about your facility if he'd heard about it. And I know you and I have talked a little bit here and there about uh getting together one of these days and doing some co-marketing and co-branding and stuff. My brother who lives in Virginia knows about Island Pickle and you guys were only five weeks old. So I don't know what how that is or what's going on there, but there's some level of brand awareness right out of the gate. Branding takes years. We all know that. What did you do like day one? And I know I saw some stuff, I heard some stuff on the radio. What did you do right out of the gate as far as branding and marketing goes, go?

Bill 15:54

Well,

Branding Gaps And Marketing Reset

Bill 15:55

I'll tell you what I did, but I'm gonna first compliment you guys on what you do because you know, I mean, I I think it was 10 years ago where I or maybe it was it was in that time frame where I needed to get my gutters cleaned and have it got them because of your your marketing. I I you know you guys have been my personal residence, you know, cleaning company on my gutters for all that time because of your marketing, because of you know what Bobby Downs spelled on the radio for the last however many times I've heard him. It's it's countless. And then when I met you the first time, I'm like, oh my god, he sounds just like that. It does happen. I do hear that. I don't think I ever told you that. But uh, but why your was it your brother you said?

Dennis 16:36

My younger brother lives in Virginia.

Bill 16:38

Yeah, and why why your brother heard about it is because in the pickleball scene, we were we were broadly known. It's a niche of people that are really advocates of that sport. And and while we nailed it for pickleball, we failed it on the restaurant. We failed it on the rest of what we did. And and so while it's a success story on people knowing about us from a pickleball facility and what we did and how we got there, I I think we completely missed the ball on advocating for the tavern and advocating for the social elements of what it is we do. And that's what we've gone through this massive, you know, refocus and rebranding uh and spent, you know, a considerable amount of time and effort and money to f to figure out how to get that better. And so everything we talk about now is the social elements and even down to the memberships, you know. You Chris, you mentioned that we have a social membership and it's all around the loyalty program. That you can you can get you know extra points for coming in and being part of the community, you get discounts on certain things, you get other other amenities and other value propositions just by thinking that this is your place to come and and dine. Yeah. And uh so I I think the the key of our marketing right now is social media, candidly. I I don't think that that and how do you get more and more of it? And we just had an influencer night last night and we invited 50 people around and and 40 of them never had been in the place before. So that tells you how much of an opportunity we have to grow because the awareness of everything outside of pickle paw was still somewhat foreign to people. So I I you know I was on I've been on the radio for two years and and uh I have you've been in newsprint and and and solicitations on a number of fronts, but I think that just the constant message of you know who you are and what you offer in as many forms that are relevant to you is is critical. And for us right now, the fastest way to get that adoption, I think, is through a continued presence on on improving our social media communications.

Dennis 18:41

I think it's a great idea because I'll back up a little bit. We did a little bit of work on your building after it was completed, and we had to fit it in on a Saturday. It was busy time. We wanted to get you done, I think, before Memorial Day.

Bill 18:57

Yeah, it was close.

Dennis 18:58

So we had to squeeze it in on a Saturday, and we went in, we got there about 6.15 in the morning, and you guys were packed. Yeah, the parking lot was full. I could not believe it. On a Saturday morning in May, 6.15 in the morning, you got a full parking lot. And we worked for the better part of that day, and every hour we would see the changeover, or every whatever it was, we'd see all these people leaving, pulling out, new people pulling in. This was this was on a Saturday in May. It was impressive. I was really happy. Every time I walk into your place, I'm happy. But this particular day, I was really happy for you guys that this was late May and you guys were booming. And I think that's a testament to pickleball and where you are in that pickleball community. But I also think what you're telling me here is all these pickleball people know about you, they just don't know the full uh comprehensive array of what you do.

Bill 19:56

And so to that point, one of the things we do now, because summer happened,

Indoor Play Value And Seasonality

Bill 20:00

right? And so if it's if it's May and it's rainy or it's cold, you're gonna play indoors. And and the indoor play experience is world-class for what we offer. But if it's summer and it's 72 degrees out and it's you know there's no wind and it's sunny, you're gonna prefer to play outside. And so we've seen a drop-off of the amount of people.

Dennis 20:19

What's gonna happen in these next we're gonna have a 90 to 100, 170 degrees? I presume they're gonna come back.

Bill 20:24

Come back. I think that's gonna be an interesting. But but my point where it was going was well, you know, I have court space that I can make available. And so I've offered you it's called just come play. So you in the in the summer months when I'm not busy, you can why why wait on an overfull court when it's outside and then you're gonna battle the wind and all these other things, and maybe play three times in an hour and a half when you can come and use my facility and do that with actually no reservation, no fee. It's just come play. And the point on that is marketing because I want to have you come in the door because when you come in the door and you realize all the amenities that we have, and then you realize how good the food is, and then you see what's going on there. And if you're in the evening, you can hear one of the bands, which is there Thursday through Sunday. Um, you'll realize that this is not just a pickleball place. It's a place where I can play pickleball, but I can do so much more. And that's the key of what we're transitioning this social element to right now.

Chris 21:24

Yeah. I was just gonna say I was down my sister's down in uh Charleston, and uh I know that they lost a couple of their pickleball courts because some of the noise issues in the community and stuff like that. And I was just thinking as you were talking about being indoor, I can see more and more of that traffic being driven indoors because of issues like that.

Bill 21:42

You know, when I was researching to do this, there was a tremendous amount of momentum around that locally, right? And so, I mean, Thalmouth, the town in Falmouth has had a lot of discussions around it and they had some restrictions and then there was an outcry outlash. Other towns have had um some activities, some discussions. And what a lot of the towns have done is chose to limit the time of which you can play. So they open later or they they're pub, they're they're at least the outdoor facilities. They're hard to get into. So because they limit the total hours that they can play, they are hard to get into. And so we I provide an outlet for that so you can play a longer period of the day, weather independent. Um but the outlash or the outcry of the noise abatement piece, I haven't seen too much of it lately. Um it it's happened, it still happens across parts of the country, but I haven't heard too much about it as a specific complaint recently.

Chris 22:34

Yeah, I think in some of these places they built like 10 courts. Yeah. You know, and so the noise and 10 courts, you know, so they just decide, oh, we'll cut it down to three or four or something like that. So and they're jammed, though. I've gone by the one in Austin, my my son lives in Austin. There's a huge setup there. I was out and I was out running, run, rap ran by one of these places. It was absolutely mobbed. It was like 10 o'clock in the morning. Of course, everybody in Austin, you got to get out early and play. But uh uh yeah, it was absolutely mob. I could not believe the number of people who are out playing.

Bill 23:02

One of the things I love to do when you give a tour to people is when the courts are full and and you can be in the tavern or walking by it, and then you got the glass windows so you can see everybody in there playing, but you can't hear anything. Yeah, that's amazing. And you can, you know, you hear the music in the in the tavern, or you hear the noise or the bustle of the tavern, and then you open the door, and then you hear nothing from the tavern. And all you hear is pickleball noise. And it's it's crazy. And so the whole concept of you know, let's let's allow people to be social and people to play simultaneously really is a home

Leagues Clinics And Scoring Basics

Bill 23:33

run. And it's really cool.

Chris 23:34

Do you have like league championships and stuff like that? We have various leagues.

Bill 23:37

There's a league every Thursday night right now. We'll have more and more leagues. We we we continue to modify the schedule to fit what people ask for or or what doesn't work. And if it works, we keep it up. If it doesn't, we tweak it, we change, we move, and and uh maybe we're six months in, or this is the start of month seven now, right? For us, and so there's still too much to learn. Our first summer, right? And so we we continue to uh evaluate you know what we can do to make it a better experience for our clients.

Speaker 3 24:04

Yeah.

Dennis 24:06

I think you're being a little bit hard on yourself where you say we fail in the restaurant. Yeah, we we opened it, marketing, the marketing piece of it. Yeah, but you you recognize that within five months, yeah, and you and you alter. We've all done that in small business. You open up and you think you're an ex, but you're you're an X slash Y. I I've done that a half a dozen times. Um, even here, and again, I don't really want to talk about my business because that's not what we do here, but Cape Card gutter monkeys opened up with two old guys 12, 13 years ago as a gutter cleaning company. And we realized within a year we should be in the install business too. And I'm a retired builder. I I I you know it's been my world. And we quickly recognized a significant need in the community, and we became a full service gutter company. I don't think we failed that first year. I think that was a learning process. And I think you're still in that learning curve. You haven't even been in business a year, and look at all these new things that we're talking about. That's true, that's fair.

Bill 25:16

It's a good perspective. Yeah, I guess I came from the GE world, right? Where you fail fast, right? And so and and so you think and and failure is not a bad thing. And so I don't when I say the word, I don't think of it as a bad thing. And and but I can appreciate some of your listeners may when I say it about myself. And so I I respect what you're saying, and I agree. We appreciate it. You know, one of the things that uh really strong, you know, you learn, at least I learned in my tenure in in uh GE and other larger companies was that um you you know the the things that you regret is you don't move fast enough. And so you know, you say, well, seven months or five months, that's pretty quick to make these changes.

Chris 25:55

And I sit there and I'm like, wow man, how come I didn't figure it out? Oh, you're hard on ourselves. Right. Of course, of course you're writing checks every month. So that speeds up that process a little bit when you have to write the checks every month for it.

Bill 26:05

Yes, absolutely.

Dennis 26:06

I I remember one time I was having dinner, uh, a group of us having dinner over in your lounge. And you know, one of the things, I don't know, Chris, have you been there yet? I have not been there yet. We gotta get over there. I gotta get over there. And you know, it was in the winter time, I'm I'm guessing, and you know, I see the the crews come in with their um you know, group of four will come in with their golf clubs, like they're going golfing, because they are. And they walk in and you know, they're they're gonna they're next in the golf simulator, and they put their clubs down and they I don't know what the whole golf simulation thing is about, but it's fun to watch. And one person got simulated angry and threw a club. Well, that's the real deal.

Bill 26:52

You know what's cool? And and it's we have a we have pictures of like the whole walkway, and it's you know, 120 feet or whatever, full of golf clubs for people that either are going to play or just finish playing and they're in the tavern then drinking. Because in this in the winter, we were like lights out on the golf simulator. But here's the cool thing.

Chris 27:11

Uh one is there's over 500 courses you can play from Pebble Beach to uh Niantic and uh you can plug that into the I heard you can even play Mount Washington, which is the one I I'm on up in uh up in New Hampshire now, so it's even on there.

Bill 27:23

So there's games, kid games, yes, which are fun with your kids, but also skill games. But then there's a driving range that you can get all these analytics of your your game. And so we'd see people come in to do all of those things. And the thing that's really cool though is when you have a parent, man or woman, come in with their kids, you know, and they're like you know, three feet tall and they're carrying their own golf bags, and you're thinking that these parents are coming in to teach the kids. And now you think about it from another golfer perspective, it's like, thank God they're not in front of me. Right. Because you know, you can teach your kids how to play the game of golf without slowing down the people behind you. And so it's a perfect opportunity. Or another one that's really cool is you know, you'll have a 50, 55-year-old uh man usually coming in with his 85 to 90-year-old father to play around that the father can't, you know, walk or even drive a cart comfortably for nine or eighteen holes. And and but and and the best one was this guy is like, uh, hey dad, where do you want to play? He's like, uh and he p he names the course, I can't remember it. But it's a course that the father played on vacation, like in Europe somewhere. Oh, wow. And they picked that guy. And and so you just see these moments, and it's like, man, that's that's what we do. Yeah, that we create experiences for a community, and that's pretty freaky cool.

Dennis 28:42

And pickleball, as as new as it is, and golf, these are lifelong sports. They are, yeah, right? Yeah, I love lifelong sports. Nobody's playing football much after the age of high school or college, other than a few pros. But and Chris and I we we met in high school, we were teammates on a cross-country and track team. Do you still run? I still run. I still run. It's a lifelong sport. I run with my son a little bit here and there, I don't run too much, and I definitely don't run too fast anymore. But but pickleball and golf are the same thing. I know guys who play with their kids. My friend David, I don't know if you met him, he's he's he's he shoots his age. He's our age, and he he shoots his age a couple of times a year now. Um ever since he retired, he got real good too. He he improved three or four strokes, I think is what he told me. I I think it's safe to say he's probably a spratch golfer. His son is a teaching pro, and I'm sure David is now playing with his grandkids. Yeah. I I know his grandkids are into the 12, 13-year-old range, and I know David's playing golf with his grandkids, and it's a beautiful thing. I don't know that much about pickleball, but I do know I know a lot of tennis players, and tennis is the same thing. You can play that for an awful long time, and and those are two really I love lifelong sports.

Bill 30:02

And the cool thing about pickleball, and there's two phrases that that Kate uh talked to. I'll I'll give you one of them. It's you know, you can play from eight to eighty, right? So you can literally you can want you can come in with your grandchild and play competitively and and really enjoy it. And they both enjoy it. The the grandparent can enjoy it and the kid can enjoy it, and they and if they're at of a similar skill level, they can really have a competitive game. And but the other element of it, unlike tennis, it's half the size of a tennis court, so it's much more social, right? So you're either so you're playing and you can have as much or as little exercise in the game as you want. I see guys completely sweated up that play, you know, that play, that play aggressively, that play, you know, at a very high level and a very fast pace, and they have an extremely hard workout. And then I see other people that are just enjoying the hell out of themselves because it's a social elemental game. And so you can do all of that on the court, which is which is back to the wife long piece of it.

Speaker 3 31:01

Yeah. Yeah.

Chris 31:03

Yeah. I love watching it on TV. I'm really surprised by that. I'm not a big pickleball player. I play once or twice with my wife. My wife really likes it. She's a big tennis player, and now she's playing that with some of her friends. But uh, I love watching it on TV. And I did look up one of these statistics. The longest pickleball rally was 78 minutes. Is that amazing? In professional 78 minutes. It was 40,000 hits they counted. That's good. So you were mentioning sweating. Yeah, 70, it was one rally, 78 minutes long. So you watch them on TV, and I mean it is it is pretty amazing. These guys are are uh good athletes, you know. And uh yeah, I think it's gonna rise in popularity because it's pretty fast pace and it's uh yeah, it's quite a workout.

Bill 31:47

And and you know, b both sports we offer instruction, right? So we have a PGA pro, Tom uh Toby, uh on the golf side, and we have three uh pros that are all extremely skilled and competent. Uh and two of uh actually all three of them are on a it's called PPA Legends team. So P Legends is it over 50 year olds and they're at a competitive level. It's a duper 5-0. I won't get into that. Uh so uh I'll just give you the first names, Todd, uh Nat and Nancy. Okay. Um the Bowtans and the Zukowski, Todd Zukowski and the and Todd Nancy and Nat Bowden. I guess I live. So they do. They actually live in Chatham and Dennis. Okay. And and uh they are part of a professional team which we'll we'll host. It'll start in in August of this year for the uh workouts, and then the league season is in the September to January time frame. And so there's two teams in the state of Massachusetts that are on the legends professional circuit. One of them is called the Boston Dragons, and they're out of um Foxboro, and the other is the um the Cape Cod Sharks, and they're home out of our location. So between now and then we actually have there's uh 10 team women's uh league at the advanced level on Cape Cod. So all the towns have a team. And two of those teams were the host uh club for that. So every Wednesday night, today's Wednesday? Yeah, today's Wednesday. So every Wednesday night from five to seven, we have uh competitive play on six of our courts. And so what's what's great is not only do you see great play uh and you have that team environment, but then when they're done, they all come into the tavern and they kind of enjoy a couple of drinks and and uh and a burger. So pretty cool.

Chris 33:36

I'm dying to know who's your bigger beer drinking demographic, the golfers or the pickleball players?

Bill 33:42

Well, I can tell you this on April 1st, when the um when all the inside golfers went outside, yeah, I felt it in the tavern.

Chris 33:50

I was gonna say because I know I have a few friends of mine. I like to go in uh simulators myself, and I got a couple of friends who can I should bring them down there because they could definitely help your bar bill.

Bill 34:00

Yeah, I lost twice when they left for the outdoors, both in the pickleball or the simulator uh dollars as well as revenue as well as on the tavern itself.

Chris 34:08

But but I know they'll be back. So you mentioned your pros. Can they explain the scoring to me? Because that's the one thing that drives me crazy about pickleball. There's three there's three numbers, and then what do you do with the second with the crazy because we got the yeah? So the first number is your score, second number's their score, and the third number is who's hitting who's hitting on your team.

Bill 34:29

Right. And so what I'll tell you, make it easy, is that um one of the clinics we offer, so we offer beginner intermediate and then advanced clinics, and the advanced clinics are by shot type. So you can do a third child drop clinic, or you can do, you know, uh a dinking and soft hitting uh clinic uh as an example of an advanced clinic. But in the beginner clinic, uh you you learn everything about how the game is played. So you can serve, you can score, you can you you know, learn how you should uh align yourself with your partner on your side and what the overall uh its strategy is of the game. And uh those clinics are forty dollars for a 90-minute session for a person. So you can come in, you know, not knowing anything about the game, and then you can leave uh wanting to come back.

Speaker 3 35:14

Yeah.

Bill 35:15

And so that's the best way to do it. And so those are very, very popular. We offer clinics uh, you know, three or four times a week or three or four days a week, and we offer private lessons, which are one-on-one with the instructor uh at the hours that you both agree to.

Chris 35:29

Do you have uh marriage counseling for afterwards when I go and play uh 45 minutes with my wife on the same team? Yeah, it's called the tavern. Yeah. We're both sort of these A-type personalities. We're hard, it's hard to be elbow to elbow on that little court with her for that long period of time.

Bill 35:47

Could you imagine like what my life was? For 30 years, I was never home. I was always traveling somewhere. And then and then um I worked side by side with my wife Tammy at our first restaurant you know, seven days a week. Yeah. And that was an adjustment for both of us.

Chris 36:02

Yeah. Well, I always say you're meant to be together because when I first met my wife, uh, we were rehabbing, she was rehabbing a house, so I helped her do that. And uh I know her family all said the same thing. They said, man, if he survived rehabbing a house with her, they're meant to be together. So it's fire, you know, it's baptism through fire.

Bill 36:20

I think it took us two years to get through that baptism, but now it's solid.

Chris 36:26

So the other kind of strange thing is the some of the terminology. So and they're all sort of food related. Touching on your you know, your there's the kitchen. Yeah. Which I guess is that little box in the front near the uh near the uh you gotta stay out of the kitchen. There's the golden pickle, which is you lose eleven zero and the other team never serves. As opposed to just the what is the other one? Getting pickled, which is losing eleven nothing. But you get yeah, but there's one serve. And then the weird one, the falafel. Have you heard that term? Actually, I don't know what a falafel is. I know it's a good uh That's a whip. Is that when you fail to get the ball over the over the net?

Dennis 37:13

Like uh like when you duff it in golf. Yeah. Yeah.

Chris 37:15

It's called a falafel. So there's a lot of kitchen uh food related names, I guess.

Bill 37:21

I did mention uh earlier, I think, that the last time I played was actually Christmas Day. And so it's July 1st right now. But uh but um Do your golf? I I haven't played golf that much in my life. Um I didn't do these things because I'm advocate of the sport as much as I'm an advocate of community development and business. And this

Island Vibe Music And Family Fun

Bill 37:42

was an opportunity to put both of those things together, which is pretty cool.

Dennis 37:46

I want to just chime in here and say a few of the times I've been to your facility, and one of them was the day that we were uh doing that roof and trim work for you. You had some beautiful island music going, and we were we were really enjoying it. And really felt like well, I was in the Bahamas. I felt like Jimmy Buffett was gonna wake up and come back around and and join us. Um it was a great vibe. It's a great feel. You know, and Jimmy used to say, and he my kids grew up listening to Jimmy Buffett, uh we we loved his music, we still love his music, and and we miss him. He used to say about his concerts, you know, he he designed concerts, so he'd say, Parents bring your kids, and kids bring your parents. And that's how I feel when I'm over at your place. This is a place where as you said, eight to eighty, and I don't care if you're playing pickleball or simulate simulated golf or you're just there to have dinner, this is a great place for kids to bring your parents and parents to bring your kids.

Bill 38:56

I couldn't have said that any better. I really appreciate it. Jimmy said it. Jimmy said it. Jimmy said it originally. I'm just repeating. Well, that's why you know.

Dennis 39:03

We can we can work that into your next marketing uh promo.

Chris 39:06

Yeah, maybe that's what you guys should do. You should cut a commercial together. There you go.

Dennis 39:09

Well, we'll get a little bit, and I'd love to do it. I would definitely love to do it.

Bill 39:14

Well, let's let's take that one a step further and make it happen.

Dennis 39:17

We we we will do that. We'll we'll talk about that at the end of the show today. But uh Yeah, it's it's it's a great place. I can see that 8 to 80. I think it's wonderful. I I can see kids and grandkids and grandparents and everybody in between.

Chris 39:30

Yeah, it looks like a great opportunity. And the name is great. I mean, we talk about names all the time here. We talk about 1-800 junk and of course the gutter monkey name and stuff like that. But Island Pickle is just a great it's a great name.

Dennis 39:41

It is a great idea.

Bill 39:43

You know, and and that there was a a long journey in the beginning of you know, because we could have called ourselves anything, right? It could have been trap classical, you know, pickleball is something, you know, you see those everywhere.

Chris 39:54

It could have been it would have been some sort of Cape Cod thing. Cape Cod, pickleball, and racket or pickleball and golf or something.

Bill 40:00

But we we chose a name that we could build an identity around. And back to the inside of it, the vibe that you get is not just in the words or the music, but you know, there's swings at our at our um juice bar, right? The the the the roof in the tavern came from a design of a place in Aruba that I saw. You know, Fisherman's Hut, if anybody ever goes to Aruba.

Speaker 3 40:24

We just got banned. I just got it a few months ago.

Bill 40:29

I walked in there, I saw the roof, I'm like, that's what we're gonna make it, you know. And so so this whole theme about make it feel like an island, a Bahamian, Caribbean, you tame, you know, a uh an island in a in a tropical area. And that's it. Music is great.

Dennis 40:46

I really did. I've been to Exuma too, you mentioned that before. Um we have friends right here in Sandwich uh that have their second home in Exuma. It's beautiful, and we spent about a week, week and a half down there. I think it was right before COVID, probably 2019. It's it's lovely, obviously. We stayed outside of Georgetown, but um yeah, that is definitely the feel we get when we're over at Island Pickle. Um on every level. At every level. The the atmosphere, the music, the food. I haven't seen any of your live bands. I've been there when they've been setting up, been having dinner, but for whatever reason on those particular days, I didn't have the time to to hang around and listen to the bands. But so you you got live entertainment four nights a week.

Bill 41:35

We do, yeah. So we technically our our um full size full full bands are on Friday and Saturday nights. So we've got I know I I know um the most is this Saturday night as an example, and they're a very popular local band. So we do you know four or five piece bands on Friday and Saturday night, and there's plenty of place to to dance, and you can I can broadcast it throughout the facility as well as outside. And then on Thursdays and Sundays, it's usually uh duets or a single. Yeah. Uh and like on the Sundays, this this Sunday is actually a gentleman he played um a couple weeks back, and it's fantastic. And so there's a really chill vibe on Sunday afternoon, three to five or four to six, um, where you can listen outside on the patio. And the thing that's great about the patio is one, it's it's large. There's 70 seats out there. There's there's a second bar out there, but it's also uh roofed. So you know you can enjoy the outdoor weather with the breeze, but you're not gonna get baked by the sun. So it's a really nice spot.

Chris 42:33

It sounds great. I was kind of curious what your role is now at this point, now that you've kind of set sail here and kind of pushed it off into the deep end. Yeah. What do you what are you uh what are you standing around just kind of making sure everyone's doing their stuff? Are you just writing checks, or what's what's what are you doing now?

Bill 42:50

So I I you know, it's amazing how fast 14 to 15 hours a day can go by. Because that's what I'm doing. There's a couple of things. One is you know, never back to the earlier point, satisfied with what can we do better? And we we learned a lot. A lot of this whole redesign of our of our memberships, of our website, of our marketing strategies, all that came as a result of Q2. And so we're we're in the thick of that. And so now trying to see where the summer is gonna go, uh it that that dust is settling. Kennedy, I'm starting to work more aggressively on phase two. So

Phase Two Expansion And Community Vision

Bill 43:22

phase two, we have uh plans for a uh 63,000 square foot facility next door. Also, so phase two, if if our building now is 37,000 square feet and they see it and say, wow, that's pretty big. So the the phase two will be indoor turf field facility, soccer lacrosse, field hockey lacrosse, uh flag football, but also um hard surface basketball courts, which can also be futsal or volleyball. And between those two areas is a um uh rock climbing uh area, both uh um boulder and uh the carabiner or uh style. And then um a Irish pub which would be on the second floor overlooking everything. So there's a there's another phase of coming. Wow, that's amazing. Amazing.

Speaker 3 44:09

Yeah.

Bill 44:10

How's the town working with the town? Well it's been great. The town has been fantastic to work with. I I I didn't choose Mash B originally. I think Mashby chose me. I mean, not directly. I mean that it was serendipity. I was planning on building on that Kmart facility that I first mentioned when this story first came about. And I spent seven months trying to figure out how I could put the facility in 42,000 square feet of half of a Kmart. And when that uh didn't come through to lease negotiations with the landlord, um I set my sights looking elsewhere and found land on Evergreen Circle. And from that, now I have a multi-phase journey that uh I hope to execute with uh the town of Matchby.

Chris 44:56

Wow. That's amazing. That's great. Great sort of serendipity where you struck out at the first pitch and then sounds like you hit a home run on this one. Yeah.

Bill 45:04

I I I I enjoy what I do tremendously. So as you guys have kind of touched on and you said it indirectly when you said, well, we jumped around in the corporate world or the o business ownership world and then kind of landed on something that you love doing, and you show it in everything that you do. We've done the same. It's pretty cool.

Dennis 45:22

One of the things about being a business owner is you become passionate.

Bill 45:26

Yeah.

Dennis 45:26

You really do. Yeah. It's not about the money, it's about it's about the business, it's about the growth, it's about the opportunity, the customers and the employees.

Bill 45:38

Yeah, our our goal is simple. It's to leave an indelible mark on Cape Cod that provides a community center, you know. I was starting to write my prospectus for phase two right now, and there's a preface to it, and it starts with um, you know, when our second daughter left Cape Cod for Boston because there was nothing to do on Cape Cod. Right? It's like we somebody should do something about it. And then it goes on to say, well, it took us 10 years, that's when we were running a restaurant, but finally we started to do something about it. Yeah. And uh that's kind of the journey that we're on right now. And and I love that uh and I'm there every day. I'm there, you know, 12, 14 hours a day, every single day, and I I and I just love the community s experience. I I I love to talk to the people that come in and they become you know friends, not they're just not guests, they're not visitors, they're friends, and that's pretty cool.

Dennis 46:30

Well, in in 2010, my wife and I we retired, so to speak, and we moved to Cape Cod from uh up where Chris lives, up in the White Mountains of New Hampshire. And Abs and I had always been self-employed. And now for the first time in our however many 30 plus years together, we didn't have a job. And we were good with that because we were always working as you as you know, seven days a week. It's crazy. And my college roommate and I we started the Gotham Monkeys in 2014 um with our wives, and we were back in business again. I love being in business, I love being a part of the business community here on Cape Car. It's so fulfilling, it's robust, it's dynamic. There is nothing quite like being a part of the local and regional business community. Everybody knows who you are. I talk to people from here to P Town, everybody knows who you guys are, everybody knows where you are. I think it's just a matter of time before you become a household name here in Cape Cod. And I know you're heading in that direction.

Bill 47:43

Yeah, thank you. I mean, that that's the thing is that when I left my corporate experience, and it was 30 years, and I had a lot of big jobs, and I just and I didn't realize it at the time, but when I went to working in the restaurant or our cafe and our catering business, and I just I think retrospectively I shut my brain off for a few years, you know, and I was happy working in the kitchen and and you know, working in my farm because I have a farm as well, and just was kind of complacent and and i I didn't realize it at the time, but in 2023, when that you know Paul made that comment about this potential opportunity, all of a sudden the Noran started firing, and now I can't seem to shut them off. I just love the business experience. I mean, I I love talking to people about business, I love talking about my business. You you've probably figured it out already. I love talking about myself. Um, but uh my my point is is that I am always willing to give somebody a helping hand on their business and their thoughts and their perspectives because it's there's something about you know the process of business for people who love business. It's it's pretty cool. And so I'm certainly having a ball doing what I'm doing. And it's it's not an easy journey. It's daunting. There's a lot of risks on every step and turn, but but it's it's so satisfying. It's pretty cool.

Dennis 49:04

I'm I'm so glad to hear that because it shows. Yeah, yeah. It really does show. I can you know, I've obviously crossed paths with your wife a half a dozen times at least, and I can tell she shares the same passion that you do. Yeah, she always comes over to our table, Cecilo, and and um, yeah, you can tell you guys love what you're doing over there.

Bill 49:24

Yeah, it's a joy. But thank you. And this was a great opportunity too. This was a joy.

Chris 49:28

Yeah. Oh, thank you. Yeah, it's nice to have you. I've been watching that building going up and wondering, wow, that's that's a that's quite that's quite an undertaking. You know, it's amazing too, is that you you have to get past your building before you start to see it. It's as big as it is, you gotta drive halfway down the street to see it. Well, my my uh sister lives in Falmouth and she she comes over here. Uh, I don't know how she heard about it, but she comes over here and plays pickleball. And one of her things is she was driving by the gutter monkeys place. She was like, Oh man, those gutter monkeys, they need to put a bigger sign out front now.

Speaker 3 49:59

It's true.

Chris 50:00

So you're doing the gutter monkeys a favor, dragging all those people by now, put a big sign out there saying, Are your gutters clear?

Dennis 50:07

Well, uh, you guys are doing it right. You guys are doing uh people know who you are. I I think you're gonna show some steady growth. And I think with all these ancillary products and services and atmosphere that you have, um people are gonna love your food. They're gonna love your drink, they're gonna love the atmosphere, and it's it's great to be your neighbor.

Bill 50:29

And it's likewise, and thank you. It's it's great to finally put a face with uh with Bobby Natasva. And uh and uh you guys have have been uh you know truly representing what marketing strategies are for some time. And like I said earlier, is that I started my journey with you because of your marketing. And and uh it's not often that that happens with the company. And and so the fact that you do this as well because of your passion for business and marketing and helping others help themselves is pretty pretty cool.

Closing Thoughts And Thanks

Chris 50:59

All right. Well, we've had a great time. Thanks for being on the show. Thanks for being on the show. Yeah, it's been a great uh it's been very interesting. It's glad to put a face to the to the name, and I guess vice versa. So thank you. All right. So guess we'll head out on that note. No monkeys were harmed in the making of this podcast. That's right. We'll see you next time. Bye. Thank

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Chris 51:23

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