Life Lessons from Pickleball™
Meet Shelley and Sher, the dynamic duo, who found more than just a sport on the Pickleball court - they discovered how Pickleball was weaving its magic, creating connections, boosting confidence, and sprinkling their lives with amazing joy. Inspired by their own personal transformation and the contagious enthusiasm of their fellow players, they knew this was more than a game. Join them on their weekly podcast as they serve up engaging conversations with people from all walks of life, and all around the world reaching across the net to uncover the valuable Life Lessons from Pickleball™.
Life Lessons from Pickleball™
E19: Dean Matt: The Pickleball Pilot's 48-State Challenge
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How far would you go to share your love of pickleball, meet people across America, and prove that joy, community, and adventure can all fit into one unforgettable journey?
In this episode, Dean Matt Dean shares the remarkable story behind his 48-48-48 Challenge, an ambitious pickleball adventure that took him by plane to 48 states in less than a month to play pickleball with people from every walk of life. A longtime CFO, pilot, filmmaker, author, and proud owner of his own aircraft, Dean talks about how he first discovered pickleball after moving from the Chicago area to Florida, and how the game quickly became more than just a hobby. What started as curiosity soon turned into a big dream inspired by endurance athletes and his own desire to combine flying, travel, and pickleball into something totally unique.
Dean explains how he planned the route, coordinated courts, transportation, housing, and local players in nearly every stop, and ultimately traveled more than 9,000 miles while playing pickleball with senior pros, local club players, public officials, Special Olympics athletes, and even a 97-year-old woman who became one of the most memorable people on the trip. Along the way, he shares stories from places like West Virginia, New Mexico, California, Wisconsin, Idaho, and beyond, revealing how each stop offered its own version of hospitality, joy, and human connection.
This is a fun, uplifting, and inspiring conversation about pickleball, aviation, the 48-48-48 Challenge, Florida pickleball, senior pickleball, community, travel, friendship, resilience, adventure, and the life lessons that remind us there is nothing quite like pickleball for bringing people together, softening our edges, and showing us the best of what people can be.
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An uplifting collection of short reflections and life lessons inspired by our podcast conversations with people from around the world. Through stories of community, empowerment, and joy, the book offers inspiration both on and off the court. about community, empowerment, and joy through the game of pickleball.
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48-State Pickleball Challenge by Flying CFO
Speaker 1Hi , I'm Shelly Maurer and I'm Cher Emrick . Welcome to Life .
Speaker 2Lessons from Pickleball , where we engage with pickleball players from around the world about life on and off the court .
Speaker 1Thanks for joining us . Welcome everyone to Life . Lessons from Pickleball . We're so glad to have you and we are delighted to have a high-flying pickleball player with us today , dean Matt Dean , for the past 20 years , you've held the position of CFO in a variety of industries and you've been a pilot since high school , which I find absolutely amazing and you've owned your own aircraft for 25 years . Also , you are a filmmaker and an author my gosh .
Speaker 3And I love the nicknames . You're known as Mucho Dinero , A-E-R-O . Great play on words , Mucho Dinero and the Pickleball Pilot , and we're looking forward to hearing how those nicknames came about . But first , how did you learn about Pickleball and what was going on in your life at the time ?
Speaker 4So I think the first time I heard about pickleball was in Chicago . I was at a Dick's Sporting Goods with my wife . We were probably in the golf section and I strolled over to the racquetball section and saw pickleball paddles and wondered who plays this stupid game . It's a stupid name so I thought it was pretty sophomoric . But anyway , put that aside , my wife and I decided to move down to Florida to get away from the high taxes and the politics of the Chicago area and we moved down to the Sarasota area and we moved into a country club community to play golf , a lot of golf , and probably after six months we didn't play too much golf and we played a lot of pickleball .
Speaker 4We got introduced to pickleball Down here . There's not a lot of racquetball going on . You know that's really up north for the most part and you know , but it's easily going on . You know that's really up north for the most part and you know , but it's easily transferable . You know , when you learn how to play tennis or racquetball or table tennis for that matter , you could play pickleball . So that was my first introduction .
Speaker 1And when was that ? What year were you ?
Speaker 4introduced , so we've been down here three years .
Speaker 1We moved in March of 2021 . I think the first time I had a pickleball paddle in my hand was probably January or February 2022 . Right ?
Speaker 4away . And so what level do you play ? Typically I would . I'm about a 3.25 , I guess . So I'm right between a three and a three and a half , just average , you know , nice , and I thought I would get better . You know , as I started to play , I'm like , okay , well , I'm like a three . Now in a year I'll be a four , you know , and I'm not getting any better , and so I'll just be a three and a quarter for the rest of my life , which is fine yeah , I'm plateaued too shelly continues to improve .
Speaker 4My wife improves . It's fun watching her improve , whether it was when she was first golfing . I'm golfing the same that I did in fifth grade . She started golfing 10 years ago and it was fun watching her improve . And same with pickleball . Everyone says how good she is . When I left for my trip , I took this trip around the country . I come back and she's like I'm like is this the same person ? Because she got better over a month so , hey , you've just mentioned this trip .
Speaker 1We are dying to hear about it and we we know it as the 48 , 48 , 48 challenge . So where did , where did you get this idea and then tell us about it ?
Speaker 4so I got the idea in chicago , um , with a plane . Uh , I always wanted to figure out a way to play , uh , 48 rounds of golf in 48 states and in 48 days . But the 48 48 concept really came from a guy named the Iron Cowboy . And look him up , he has a great documentary . The guy is a phenomenal athlete . This guy did 50 Ironman triathlons in 50 states in 50 days and there was a documentary . It was just an awe-inspiring mind over matter that this guy could be able to do that . He's doing 126 miles a day in 50 different states in 50 days and the documentary just captured the human spirit of how somebody could do this . He subsequently went on to do 100 Ironmen in 100 days in his home state in Utah . Crazy guy , look him up , the Iron Cowboy .
Speaker 4So my goal in Chicago was well , I got a plane , let's do this , let's do 48 , 48 , 48 . But it will be golf . And so I tried to find some sponsors in golf . And then I had hip surgery that got in the way and we moved to Florida . So that idea was toast , but it was always in the back of my head . So when I got down here , I met a few people , a few pilots and kicked around the idea and they say , yeah , that's good . So then I made some calls to Selkirk , who was my main sponsor on this trip , and they said this is just stupid and nutty enough that we want to be part of it . And we found other great sponsors Tyrell Shoes and Chicken and Pickle . We played at three of their facilities . So in November of 2022 is when I started putting the pieces together .
Speaker 4It took six months of planning Every state I would go to . First , I had to do my route and I couldn't visit Seattle , the home of pickleball , but that was just too far out of the way . Nor would I play in Miami , and you know I wouldn't play in San Diego , california . I kept my route to the interior of the United States as much as possible and just skimmed along some of those states just to keep it as short as possible . The route ended up being about 9,000 miles .
Speaker 4It would be about 90 hours of flying and at each stop I had to find transportation to and from a pickleball court . I had to find pickleball courts , I had to find people to play . If it was an overnight stop , I needed them to put me up overnight , et cetera , et cetera . Wow , so it was a ton of fun . It was a lot of planning and I left May 1st 2023 from Sarasota , florida . I hung a left over the Gulf of Mexico and went clockwise around the United States and I got back here May 26th and I got back here May 26th , oh my .
Speaker 1So you went to 48 states , but you found places to play pickleball kind of close to the inner borders so that you didn't have to go all the way across the state .
Speaker 4And did you find these places to play before you got there ? You arranged for these games and all before you arrived , we played at the Greenbrier in West Virginia , which is a five-star resort with its own tennis stadium . We played where the pros play in Scottsdale , for instance . We played in just a lot of different venues and as far as who we played , we played Special Olympics people . We played a guy in a wheelchair up in the Boise Idaho area . We played a guy in a wheelchair up in the Boise Idaho area . We played pickleball professionals in Salt Lake City . We played NBA pros , nfl pros , governors , mayors and lots of normal folks like you and me . The oldest person we played against was a 97-year-old woman in Kalamazoo , michigan . We play regularly with a 94-year-old gentleman down here . Vince Golden is his name . I played with him today and he was him and my wife and another gentleman were on my last stop here , the 48th stop here in Sarasota , may 26th 2023 , over a year ago .
Speaker 1So every day you flew to a new state .
Speaker 4I would do two or three states a day . Oh no , kidding yeah . So out West , you know , it's one to two states . The states are bigger , a little bit more transportation , a little bit more flying , and out East , like I knocked off New York , vermont , new Hampshire and Maine all in one day .
Speaker 3Oh my gosh , so was it just always one game .
Speaker 4Yeah , so officially it was one game . The goal was to not so much about me but give the local pickleball club or the local facility private facility that just opened up Get a reason to get the media out there to cover this . So we had media at all the stops . We had national media . We were on Fox and Friends on national media and my website's just full of a lot of memories and TV cameras and people we played against and things . Whenever I would play against a governor or a mayor , I wore a bow tie . You wore what .
Speaker 1A bow tie .
Speaker 4I wanted to show them some respect .
Speaker 1That's awesome . Oh my gosh , what a terrific opportunity to see the country and meet people from all over . What were some of the surprises that you came across ?
Speaker 4Well , you know , after six months of planning , you know I thought long and hard is my hangar door going to ? Is the electricity going to work when I go ? It was a Monday morning at 7 o'clock and I was going to have a bunch of headwinds , so I had to take off a half an hour earlier . My first stop was Mobile , alabama , and it actually turned out to be one of the longest legs . It's about three hours to get to Mobile and we had just tremendous headwinds and it took a little bit longer . So , will the plane start ? Will the hangar door open ? Will they be waiting for us in Mobile when we land ? Am I going to be able to make the schedule and be there ? Are my calculations correct as far as how long it would take to get to these places ? Did I have enough downtime to be able to have them pick us up ? I didn't want too much of a buffer , you know cause I had to keep this train moving .
Speaker 4But , um , some of the surprises . Um , well , when we got to Salt Lake city , uh , which was about our 12th stop , I guess you know , I went up the coast to California , played in Oregon and whatnot . Um , well , before we got to Salt Lake City
Pickleball Journey Across America
Speaker 4. One of the surprises was my wife has been to 48 states . She's never been to Oregon or Idaho . So I flew her up to Idaho on Southwest Airlines , or , I'm sorry , to Portland on Southwest Airlines . So now she's in Portland . We played together in Portland , we played over the river in Vancouver , washington , and then we've gotten our plane and flew to Idaho . Now she's got our 50th state the mayor out there in Eagle , idaho . When we played against him he presented her with a 50 state plaque . So she was surprised about that . I've been to 49 states . I haven't been to Alaska I'll get up there one of these days but that was her 50th state and good for her . We just had a lot of fun .
Speaker 4When we got to Salt Lake City then she was going to hop on a plane and go fly to Chicago and meet me there a couple three days later , after I kind of worked through the Midwest , me there a couple three days later , after I kind of worked through the Midwest , we got , so she left and then I got stuck in Salt Lake City for two days because of icing in the mountains . There was really no way out of there . So what I had to do instead of . I still had 30 or 40 states left , so I would have had to have pushed each one of them back , yeah , two or three days , and some of these places were advertising . I'd be coming , you know , for months and the news media was going to be there . So I had to make a tough decision . I actually had to cancel four states , so there's four states that I've been to before , um , but I didn't get to go to North Dakota , wyoming , montana and Nebraska .
Speaker 1Oh , wow .
Speaker 4Just to get back on schedule . Yeah , so that's the one disappointment I had is I couldn't really do the 48 . But we still set a world record in the most number of states playing pickleball in less than a month .
Speaker 4I dare say you did make a world record , and the other thing that was fun is I was going to go with one pilot , a friend of mine , across the whole country and then we kind of changed it up . I ended up flying with about five friends of mine who hopped in and out of the plane at various times . So on the first four days I had a friend from Sarasota here . We played all the way through Kansas City and then I was by myself all the way to Portland . My wife joined me for a little while . I flew all the way , and the longest leg of the trip was Salt Lake City to South Dakota , sioux Falls , south Dakota . That was about a five and a half hour flight . And then I picked up another friend who I met down here , who lives up there in the summer . He was with me all the way through Indianapolis , picked up another friend who lives down there in Indy and then he flew with me all the way to the East Coast .
Speaker 4And then , something that was really neat , when I first started doing this , I was on instagram and I saw this guy . He actually sold his house , I'm sorry . He rented his house and bought a like a hundred thousand dollar band and his goal was to play a hundred places of pickleball throughout the country . I'm watching him a little bit . I'm like , well , he's kind of doing what I'm doing , so .
Speaker 4So I got the nerve to call him up . I said , hey , this is what I'm doing . What's your schedule like ? Where are you going to be ? So he shared the schedule with me and we were actually going to be in Colorado Springs at the same time . I said , well , why don't you play there as one of our guests ? And so we played and I said , hey , jimmy , this is weird , but can you make it up to Providence , rhode Island , somehow on May 20th or whatever ? Fly the last leg down with me to Sarasota . And he says , yeah , that is doable . So he actually drove his van , worked his way down to Sarasota while I was up in Providence . He flew up to Providence on Southwest Airlines and then he hopped in the plane with me and we flew the last eight stops , the last eight states , all the way down here , and he was the fourth person at our last stop here at our country club in Sarasota .
Speaker 4That is so cool and along the way it was . You know I watched the politics every day and you just get so after a while . And for 26 days I was just unburdened by what's going on in the country and really enjoying meeting my fellow citizens . It's like , and you know , I kind of came back thinking , you know , there's nothing that we can't solve on a pickleball court , I mean you don't care if you're a Republican or a Democrat .
Speaker 4You're just out there having fun and you know , I'm pretty confident that if our Congress and senators just played pickleball , they'd find I'm serious , they'd find a lot of common . I know they do , I know some of them do , but I think there should be a bigger effort and just have a big love fest in this country .
Speaker 1I'm with you . I'm all for building like three dozen courts or more out there and just make sure they have to each play pickleball every day , and we would have a whole different country .
Speaker 4A couple of places I went to I mean everywhere I went to they rolled out the red carpet . They thought , because I'm doing this , I was good , so I go to some places and I would . Just if I had a traveling partner with me at the time . It would usually be me and him or him against whoever the local town brought to the party and some of them brought 5.0 players . We just got our butts kicked . Other times we knew they were good players and we just switched the teams up a little bit , but it was more exhibition than you know . But people always ask you know what's your record ? I think technically I won about 45% of my games , but it didn't matter if you win or lose . That's not what it was all about . It was , you know , getting the media out there and meeting people and having some fun yeah that is that is so cool .
Speaker 3Like you said , pickleball , I just love the way it brings all walks of life together and we have fun together and like you say we just learn to love and appreciate each other , and I love that you said it does give you the feeling that we can accomplish anything together . I love that .
Speaker 4Yeah , we can another couple memorable stops I had in , uh , amarillo , it was on cinco de mayo , and they , you know , they had the whole community that , the whole pickleball club out there , uh , and I get there , and they had an event going on and they called it Dinko de Mayo . I never heard of that before . That was a big event , a lot of news media there . I went to Albuquerque , played with the mayor there , and they had beautiful courts there , big , they must have had 20 courts or something . There he made a speech , I had to make a speech , and there , 20 courts or something . There he made a speech , I had to make a speech , and there were hundreds of people there watching all that . I played out in sacramento , california . California was always kind of a hole for me . I was going to go to palm springs and , uh , that didn't pan out . And then somebody heard about what I was doing and they reached out to me and they said hey , dean , would you be interested in ?
Speaker 4playing here in Rio , linda , california . I said , sure , what do you got going on ? Well , our son is in the USA water ski team and we live on a water ski lake and then we just built a private pickleball court on our property and , oh yeah , our son's also learning to fly and we live on a runway as well . So that checked a lot of boxes , yeah . So I'm like , okay , we're going to play there and we had a great time playing there .
Speaker 4Another kind of funny story is one of my favorite stops was almost my last stop in Hilton Head , south Carolina . So I heard about this trailer , a mobile home park , and it's high-end homes . They're these buses , basically right , they're $400,000 million vehicles and I'm like this is going to be something . And they had their own pickleball courts too . They were permanent courts . They had about eight of them and a beautiful pool , and every place where you park your RV or your big bus is a deeded lot and it's a very nice facility . But I always wanted to . I'm like this would be a cool place to stay . I want to stay in a mobile home . Now , that never panned out and I almost got kicked out of there as I'm making final arrangements to play there , because I made the mistake of calling it a trailer park to play there because I made the mistake of calling it a trailer park and the general manager was like , dean , you're on a Zoom call with our board of directors and I got to tell you , don't call it a trailer park anymore , and when .
Speaker 4I got there , I found out why . It was a beautiful , beautiful facility . There were three states where I landed once and overlapped , just went over the border . One of those was in Portland . I landed in Portland and we drove over the border to Washington . In Providence , in Rhode Island , I landed south of Boston and played Massachusetts and then played Rhode Island in that same landing , and then , our next to last stop , savannah and Hilton Head . I landed in Savannah and we played South Carolina and Georgia . You know , on one stop . Well , other than that it was , you know , 44 different states .
Speaker 3Wow , wow , how fun Makes me want to do it . I know 44 different states . Wow , wow , how fun Makes me want to do it .
Speaker 4And , like I said , I've flown to most of these states before or flown to uh , I think I've never flown in Idaho before . That was about it but all the other states and Washington .
Speaker 4But no yeah , in Washington but all the other states . I've been to one one way or another by myself , but it's just really refreshing just to see the topography change . You know from the dense forests of Mississippi Then we went up to Memphis . That was a very , very windy and bumpy landing , I remember . Then the Midwest I've done a lot of flying over the Midwest and of course then you start to roll out west and you get the mesas of Texas and Colorado and you see your Rocky Mountains and the mountains . And I came into Scottsdale from a different route that I haven't taken before , so that was kind of nice . Then you get up into the northern California , the mountain lakes , and there's still snow on the mountains and it was coming back east . I've never flown up into the New England area much before , but it was just nice and refreshing . A lot of people asked at every stop what are you going to do when you get home ? The news media would ask and I said I'm going to take a vacation .
Speaker 4As much as you think this was a vacation , it was a lot of work . I mean , we'd be in the air about 7 in the morning , meaning we'd leave the hotel at 6 or something like that , and the night before I had to do all my routing and pre-flight planning and file my flight plans and make my calls yes , we're on time , there's no weather delays , things like that and then at night I would typically upload a lot of videos to the Instagram and that . So they were full days . You know it was full days , but they were fun days .
Speaker 1And the people that you met . Are there a few people in particular that kind of captured your heart or you got to know them in ways that you were surprised ?
Speaker 4Yep ways that you were surprised . Yep , well , I played um , uh , several professionals and uh , up in kalamazoo . Uh , I played james and yvonne hackenberg and I guess they're senior professionals . And uh , yvonne's mother is , uh , minnie lapointe and she was the 97 year old woman . And uh , and of all the people that I met on the trip , she , for for some reason , is the most memorable .
Speaker 4What a kind soul . She cuts her own grass , she drives her own car and she was out there playing pickleball with us . The news media covered her more than me . It was fun . Here's an example of her soul she's up on a little bit of a hill hill and the news media is doing a little story with her while I was finishing up and then it was time for them to interview me . So I extend , so I'm going up this hill , I'm extending my hand helping to guide her down the hill and she's pulling me up the hill . She extended her hand to help me get up the hill . We played governor ex-governor lynch up in new hampshire and uh , we played ex-governor george allen in virginia at a private residence . Uh , and , like I said , everyone rolled out the red carpet and it was just uh , it was fun for them to be part of it and it was definitely fun for me to be part of it , and it was definitely fun for me to be part of it .
Speaker 1So what are some of the life lessons from pickleball that you've gathered ? Either that you learned on the pickleball court or in this journey , or you learned in life and you've taken to the pickleball court . What are some of the lessons ?
Speaker 4Well on the pickleball court , you know Well , on the pickleball court , you know I guess I'm not as competitive when I don't need to be . You don't need to beat 80-year-old ladies , for instance . You're out there just to have fun and you make people feel good about themselves . God knows , they make me feel good about myself when I play better people . So it's just a lot of kindness out there and yeah , I mean you can be competitive and whatnot , but you could also I didn't know I could congratulate people as much as I do . I didn't know I had that in me . So it's kind of made me a softer being in finance and CFO and corporate corporate , you know environments and all that stuff . It's a little cutthroat and competitive . It could be a little cutthroat and competitive and this just gives me a little bit softer edge , which is which is nice .
Speaker 1So Very nice .
Speaker 4And the other thing is everybody , everybody could play . You know , we played specialics , folks up in jonesborough , arkansas , and they're out there , they have fun and we raise a little money out there .
Across America
Speaker 4Uh , the adaptive wheelchair athlete , kevin I think his last name is klein up in eagle idaho he played wheelchair tennis and the difference is if you're in a wheelchair you get two bounces of the ball . But this was the first time he played wheelchair pickleball . That's the first time I played with anybody like that and we got , we got . I tried to cheat a little bit . If I couldn't hit the ball on one bounce , I hit it on two bounces . I would say , hey , well , we get two bounces you don't get two bounces kevin gets two bounces , but you don't .
Speaker 4But you know , and he had such a great time and we did as well on that trip .
Speaker 1Wow , Dean , what a tremendous journey you took and that you included all the people along the way . I love that you did so much planning in advance and you let communities become aware of what you were doing , and that helped raise the level of their awareness to pickleball , but also the community's awareness to what was going on there wherever you were playing . I love that you brought the country together .
Speaker 4Dean , yeah right . Another memorable stop was Madison , wisconsin , and we played a senior pro there . But when we landed they were ready for it . They thought we were rock stars . They had a polka band going , they had a bratwurst festival going , you know , and they had beer there and everything , and it was just like the community was just there were hundreds of people waiting for us to play . You know , I'm just a normal guy , I'm not that , I'm not that good , but we put on an exhibition , um , and we just had a good time up there as well that is so cool ?
Speaker 1is there anything you want to promote before we our time is is just coming to a close Is there anything you want to be sure that the viewers and listeners are aware of ?
Speaker 4You know not at this time . Everyone asks me are you going to do this again ? And I don't think so .
Speaker 1Once is enough .
Speaker 4Once is enough . If someone wants to beat my world record , maybe then I'll challenge them again . Beat my world record , maybe then I'll challenge them again . But no , I'm retired now and my wife and I are just flying all over still , and every time we go we do bring our pickleball . We go up to St Simon's Island , georgia , which is on the coast , the Atlantic coast , so it's between Savannah and Jacksonville , and we've gone up there a half a dozen times already and we've got friends up there now with the local pickleball community up there , and we were there a month or so ago . I asked her if she wanted to go today . We'd go up there and stay for two or three days . But yeah , everywhere we go now we bring our pickleball stuff . And whether you know anybody there , I know people in all the states . Now , if I wanted to stay overnight someplace , that's right .
Speaker 4And I'm on the road . It's so fun . It's nice to have friends , right .
Speaker 3Pickleball brings us together For sure it does indeed .
Speaker 4Out in Utah , the guy who I never met before he let me use his house . He wasn't even there , oh my gosh . He says , hey , if you want to use the house , here you go , you can stay overnight here and use the house and just lock the door on your way out .
Speaker 1So I mean , that's the kind of people that we have in Pickleball , people that we have in pickleball . Well , this has been really inspiring , dean , just to hear how you have been able to tap into all of these different communities and discovering the heart of America , and you've been able to share that story today with our audience , and we're so appreciative that you took time out of your busy schedule of pickleball and flying to talk with us today . Thank you so much .
Speaker 4Well , thanks for tracking me down , sharon Shelley , it's been great to be on your podcast .
Speaker 3Yes , I hope to play pickleball with you someday .
Speaker 4Yeah , you know where to find me .
Speaker 1Come to Seattle , yeah , okay . Well , thank you so much , dean , and thank you all . Wow , how fun . And yeah , if you want to challenge Dean's record , he says go for it and then he'll challenge you back . Thanks , everybody , we're looking forward to our conversation next week . Bye , bye .
Speaker 2If you love our podcast , we'd be so grateful if you'd take a few seconds to follow or subscribe to Life Lessons from Pickleball . This ensures you'll never miss an episode and helps us continue these wonderful conversations .
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Speaker 2Thanks so much . Hope to see you on the court .