PHL The Hathaway Group
The Joys and Challenges of Exploring Florida Waters

In this engaging podcast, Jackson Stern, founder of Marker 26 Boat Rental in Palm Harbor, Florida, shares how his passion for boating and experience in competitive sailing led to a successful business. Initially renting boats on trailers, he moved operations to Island Harbor Marina, significantly improving accessibility and business growth. Stern discusses the joys and challenges of sailing, as well as plans for business expansion and maintaining boats.

Listen to the podcast episode here!

Today Jackson Sterns joins the podcast and he is the founder of Marker 26 Boat Rental a startup boat rental company,  here in Palm Harbor, Florida. Now Jackson grew up in Florida competing and sailing competitions, and spending a lot of time working at marinas. 

So starting a boat rental company seems a perfect fit. Now in this episode, we talked about Jackson’s drive to create his own business, what it’s competing in those ceiling competitions, and Jackson’s favorite locations to go boating,  here in the Palm Harbor dining area. Now, we were recently featured in a top 25 Florida Business Podcast list with a top 10 on the list. 

And I just wanted to say how grateful I am for everybody who has supported me who has listened to an episode who has shared an episode, but couldn’t be in the top 10 there without your support. 

So please help me continue doing this podcast reaching more people in the community, and sharing more local business owners with the people in the community. I love doing this podcast. And I’m so grateful for you to take the time out of your day to listen to this podcast. So thank you. Have a great day. 

So welcome to the podcast. Jackson.

Thank you. Great to be here.

 How’s your day gone?

Doing good. Enjoying the weather and helping people get on boats.

Beautiful day out? This is perfect boat weather. Beautiful. March, April.

Best time of the year. Spring Break. Everybody’s down. What about you? All good?

Doing good, man. Fun Day. I’m excited to record this podcast. 

I’m sure it’ll be great. , but let’s start with the boat rental business. And, where did this idea come from? Why did you want to do this? 

Good question. Been selling software to car dealers for the past couple of years out of Tarpon Springs. And I’ve always been around boats. I’ve always been boating. I’ve sailed competitively for five years and probably ended up not doing as much about a year or two ago, but competitive sailing around Florida. 

I’ve always thought about how can I monetize a hobby that I have, which is boating. They say the best day of a boater’s life is the day buys one and then the day. So I was wondering, I had a boat. And so far, I don’t have the day plan of selling it yet.

Let’s just try and see if I can make any money on the side, renting this boat out. And it’s been great. I found a platform called boat setter, which integrates with Geico and boat us. And it’s kind of if you’ve ever heard of cars or Uber, but you can rent a car private party. And it’s been great, because the insurance, the way the insurance works is pretty much when the person takes out the boat. That’s the only time you’re billed for commercial insurance versus having a rental policy on it month to month. So that’s a great thing about it. 

But just started with one boat, kind of doing it on the side. I had started it on a trailer. And that was funny, that was an interesting idea. Because I’m, oh,  what, let me just keep the boat on the trailer. Anytime a customer wants the boat run the boat, I can just bring it to the boat ramp it’ll be lickety split. And turned out to be not a great idea. 

Because as I was pulling up to the marina on a gorgeous Saturday, and everybody in their mom was there and I’m, oh shoot, I’m  12 people behind the guy at the dump in the boat in the water. And I have these renters over here. I’m on this end of the parking lot. And it just wasn’t working out. And then when the renter’s would come back in they’d be eight in line. They may or may not have driven a boat before, so they’re freaking out. 

So I’m, Hey, I’m over here, just your four people behind them. You should be out of the water in two hours. , that wasn’t working. I only did that for about two trips. Actually, I started the business. Sorry, I started the business about a year ago, last March. Okay. And it only took me about a day or two to figure out that that was not the way so I had contacted a good buddy of mine, Matt Gannon, who I used to run Home Port Marina with in high school. He works at Island Harbor Marina, which is just next door to Ozona Blue and I’m hey man, I need a slip ASAP for this boat. 

I tried this trailer thing it’s just not working out. So luckily he was able to get me a slip there in the water bottom painted the boat and started just marketing out of Island Harbor Marina. And it’s been great ever since because the boat just sits in the water you don’t have to get the forklift to put it in. A super seamless person meets you at the marina. Hey, maybe behind the main office yellow and blue shack and we’ll just go from there. 

I think that’s it. It’s interesting how you started. 

Learn from your mistakes. Quickly and you want best? I mean, that’s the key. 

Absolutely. What’s been what have you enjoyed about the boat rental business? 

There’s a few things to enjoy about it. There are a lot more things to endure with crap breaking, boats sinking, and motors failing and stuff. But the great thing that makes it all worth it to me is being able to take John and Jill from the middle of Iowa and being able to put them on a boat and show them the real Florida experience.

I’m an old school guy, the Marina that I’m at his old school just super simple. And they can go out there for the jet the day and see him leave the dock and they’re smiling. They’re, Oh, I don’t know if I could drive the boat. And I’m trying to get a picture of them leaving, Hey, give me a thumbs up we love Margaret 26. Try to drive the boat. 

When they came back from the day, and they had 2030 pictures, we saw dolphins kids got to play in the sand and collected six trash bags full of shells. And seeing that coming back. It all just reminds me of being a kid and enjoying a boat off the bat and seeing them come back to the dock after a great day of being sunburned and enjoying their trip that’s really what it’s all about. For me, I think it just doesn’t even seem to work at that point. That’s what I did.

You grew up in this area. From Ozona. Originally? 

Nice. So just being around there pretty much I’ve worked at every Marina and Ozona. The big amount of five Marinas? What was the other one? Ozona shores and speckled trout. Okay, pretty much, I get tired of it. Leave to focus on something else. And then I’d get a call from a new Marina. Hey, we heard you have worked at this marina. come and work for us. But that, that’s just that’s pretty much Ozona.

So you grew up around boats?  

Always. pretty much. 

What about sailing? You mentioned you did competitive sailing, what is that?

It’s crazy. I mean, it’s it’s fun and pretty expensive. Especially when you break stuff. But competitive sailing, I started probably mid-seventh eighth grade or something. 

Are you buying the boat,  you own the boat as usual, or you can join a club that has boats there? 

So I was at a club, using the boats there, the boats were called for the 20s. And we would pretty much have a team there. And we would kind of run around Florida, sailing and competing with the other squadrons or clubs around the state. 

Pretty much for fun. And it just got to the point where it was taken up  Saturday and Sunday all day every day. Didn’t really have time on the weekend, and I pretty much kind of stopped doing it around high school but own a few sailboats ever since never let that sight Leave me I just love sailing.

It’s funny love about sailing. I think it’s kind of cool when you can take something wind from nature and have a, I had a 3132-foot sailboat and it’s a 10,000-pound vessel and you can have a gorgeous day out there and you’re hauling ass with people on the boat just powered by wind and it’s feeling over. Or, you get a gust or, storm rolling in and you can just wing it out there. 

Or you can camp you can race other people and you’re only limited to about eight or nine miles an hour, so it’s fun. But it feels like you’re going 1000 miles an hour when you’re on the actual boat. , it’s great. It’s just riding a bike. You’re never gonna get, unused to it. You just love it.

Is it hard to say sailing is it hard a hard thing to pick up?

The Joys and Challenges of Exploring Florida Waters

Let’s see it’s about the same as learning to drive a car there’s a clock pretty much where whichever when way the wind is going. That’s pretty much where you’re just adjusting your sail angle and shooting in and shooting out. But no, I mean, you could pry learn just driving a stick either a couple hours or a couple days of you suck, but ya know, not super hard. Just gotta mainly focus on where the wind is coming out from and from there. You’re just seeing which way to adjust the sails to achieve the most efficient course, pretty much.

That’s cool. Would you ever live on a sailboat?

Definitely thought about it. But at the same time, it’s now it’d be a great time to live on a sailboat because there’s pretty much the air feels fresh AC But in the summertime Oh, I have a buddy that does live on a sailboat and his AC because you can have an AC Oh, wow boats, a portable air conditioner and he’s dude, this thing broke again, it’s  9000 degrees in there. And then during winter, it’s just cold in that thing.

And getting outside it’s windy or cold.  Half the time if you have an older boat, which we’re used to older boats are the most affordable. But, it’s it’d be fun just to do for a couple of years, maybe, save up some money, get a decent boat, fix it along the way, go sail to the Keys Bahamas or something, and then come back. 

But you see a lot of people because you can just justify the price of living in a normal house or apartment you’re only paying for the slip fee, which, decent sized sailboat, probably four to 600 bucks a month. That usually includes Water and Electric. So, if you’re on a whim, it can be a cool way of living. But I think once you take all things into consideration of owning about your s live in the in the house.

Be that have the sailboat to this or just if you’re doing it on weekends I go do that, for sure. 

That’s cool, I’ve always wanted to know if I want to learn how to sail, but just that. So you said just the experience of, being on a sailboat.  I have this idea of vision of, someday I want to own a catamaran. And just cruise around on those whose are great, because they don’t draw much water, you can get pretty shallow, pretty oh, bigger 140, 150, 160 feet because the weights kind of just dispersed on both. , so makes sense.

You can get shallow they’re popular for that. And you can get into most ports in the Bahamas that is, you need a shallow boat. But they’re just so big.  It’s hard to find a slip for it and out of town. 

But you can always anchor or have tender on the back of it a little boat, your golf cart.  

So where do you see, where do you want to? How do you want to grow Marker 26? What’s your vision for what the boat rental could be?  

I mean, at this point, I’ve thought about that a ton ever since I started it about a year ago, up until I’d say, January of this year. It’s been kind of slow,  I’ve had honestly the spring of last year, which is funny enough, the best time last year was when I had the most mechanical issues on the boat, or, of course, just learning. 

So I was only getting two or three rentals a month. And otherwise, I was just having buddies take out the boat. , just go run it, you throw me a couple of bucks for gas. That’s all, go because I have the logo on the side of the boat. I’m, go sell it, go sell it on the sell a great, you don’t have to pay for gas. But up until January, it’s been picking up. Instagram I run a ton of Google ads and, a little bit of Facebook and started just out of nowhere getting one rental a day clockwork from late January to early February. 

And I’m   Where’s this coming from? Because I have this app and it’s boom, boom, boom, you got this booking the others booking online,  now I don’t have to have this thing break down. Thankfully, I did all of the maintenance from last year,  when the time was good. Of course, the boat ran great during winter, which is when nobody used the boats and ended up just picking up a second boat. Late January. I’m all, this thing’s growing. 

Let’s just, save up, keep going and keep working. keep selling at my normal job. And then just kept acquiring boats and luckily, it had a second spot open up at the marina can get the new boat in there. Had my mechanic on standby. Rig it all up, and put the motor on there. And funny enough it’s the same boat as the first one.  

I was planning on having a little 18-foot center console but I was looking for a pontoon or a deck boat because literally month to month I probably turned down 20 People hey,  you got the pontoon. Do you have a pontoon? I’m now. I don’t that’s definitely on the radar. , I was looking for a pontoon or deck boat and my mechanic was my buddy. He’s, Hey, man, I got this, this hole in on trade and I got this new motor on wholesale. I could build it into one boat if you want. 

The only thing is it’s the same boat just a year newer and I’m, Oh my God. , I’m, Al, let’s do it. And, at that point, I was getting substantial every day-a-week rentals I’m, let’s just go with it. So he finally finished it probably early February so it’s been running ever since then. Of course when you finish the boat that’s not when it’s done. You gotta keep going and keep screwing on this bolt that fell off or fix this problem. 

Someone ran into the ground but so it’s been great to have both boats now and one at least goes out per day if not two and I have my buddy Matt at the marina while I’m working I’m hey man,  can you get this read through, please give him the app you can have a manager in there someone that and as similar to what Airbnb or something, exactly. You can have a kid or something. Hey, take this over. Make sure they look over the contract. 

Make sure that they know the boat is still flowing. , the profit is still intact. It’s a running life jacket. Where are the fire extinguishers? Okay, great and have him sign on the line. And then obviously throw him a little bit of that he’s happy he’s working. He’s able to make a little bit on the side but as far as expansion goes, whenever I can, I’d love to keep acquiring one at a time, just one thing at a time. 

Just keep building the customer base from there there are a ton of floating spots at the marina now the biggest factor is just waiting for ways because in Florida it’s crazy there’s no space anywhere for boats. 

So that’s the main concern is just finding space and adding one at a time until I have enough real estate there to consider okay, this is taking 1,000% of my time not sure if I’m into this anymore and I then possibly because that real estate is very valuable for, a boat club or someone that’s looking for Marina space because marker one Marina and Ozona they just had when the last hurricane came in there destroyed all their docks so freedom Boat Club, the one there had  11 or 12 boats there they had to leave they had to move everybody out of the Marina because they had to replace all the docks and they’re saying it’s gonna be another two years before the docks are, they’re gone. I don’t know if you’ve seen it, now gone so they have no floating real estate there. 

And that was probably, half of their frickin monthly premiums coming in. But, so either build it up until I can just get all the spaces there if not look at another Marina for some space potentially trying to see if I can bring another owner and in and depending on how big it is. But  number one it doesn’t feel like work it’s a hobby and number two a second part of it is it just makes money on the side, so let’s kind of just where I’m going, but for now I 

What do you what are some of your favourites growing up here this would be cool but your favourite places or spots to go boating or locations to take the boat out to?

You can I mean thing also just good about where I’m at is that you’re 10 to 15 minutes away from anything, from three Roker and close to Kaladze Island Clearwater Beach honeymoon. But honestly, I mean, really anywhere where nobody’s at which is uncommon these days, especially on weekends, or it’s how can you blame them? 

But what’s funny enough, probably my favourite spot is just outside of I’m trying to think of how to describe where it is, but just south of the Dineen causeway there’s this little island that’s, an eighth of a mile away from the land, it’s in it’s they called it Kellogg island because what’s his name? 

I’m gonna screw it up a J. W. Kellogg. , the guy who invented the cereal used to have an anche mansion? They just unfortunately tore it down. , super cool  20s Pink 7000 square foot gorgeous house by this island and you could if you look at pictures online Zillow and stuff, you can see the island from the little porthole in the house but cool I kind of go on there because you got all the freakin real estate there to look at. 

It’s kind of inclusive there’s only a little bit of beach and not many people there and it’s shallow there. , still run through there. But I mean, he can’t be, three Roker Khaled etc. But as far as just trying to find that local hangout wherever it is now. Probably that little island Kellogg, it’s great. Everybody loves it.

Because there’s a bunch of little spots that we can’t spoil islands,  those are good those are especially for camping we loved growing up and going camping on those islands and doing it zero part of society is out there when you have a bunch of kids camping. But it’s great you can pick up your trash bring it home, whatever. 

But I mean tons of memories growing up and everybody bringing the boats out there Dawn of winter it’s  40 degrees out there but it’s  Oh, Christmas break?  let’s go island camping that was that let’s go island camping. And now is a great time. That’s probably in my opinion, where I would go.

I love that. There’s we I forget how many years ago we went out there for more of my wife’s work trips to get the team together, and whatnot. Oh, cool. And we went to one of the spoil islands. Trying to think where this one was it’s probably close to where you’re talking about, but it was a little bit bigger than I think the one that you’re referring to. 

So we’re getting set up. We got part of the part of part of us out there getting the gear, off the bow and don’t have the tents set up yet probably aren’t. Or they were just getting set up not completely set up. And there’s this massive storm that rolling in and we’re, sure, Gorgeous. And of course,  before we can get set up, it rolls in just to dump a ton of rain. There’s lightning popping everywhere. winds blowing tend to blow over. There’s a or shoot.


So it’s, when was that mid-summer?

It probably was the perfect day. Oh, absolutely. And then it rolls through. And then it’s, okay. Give me five or six minutes, or milliseconds. And you’ll have the best day ever. . Kind of coming into that season now. I know. It’s it’s crazy. Perfect now. Otherwise. 

Yep. So excuse me. I wrote down a couple of stats that I’ll we kind of just talk about because I just try to learn something and find it kind of interesting and stuff. So in the United States, there are 14 and a half million people that own a boat. And then there’s  25 point 2 million boats. In Florida.  

No, but this was this isn’t the United States? So  14 million people own boats. And that’s, 11-12% of the population. owns a boat. 

Seem about. That’s Oh of course.

So most people own two boats. 

So that’s crazy. That’s crazy. , definitely have to pitch that to them. , do you realize you’re the 11%? You’re leaving for marker 26 Bone rental. And their bone was 11%  here. How do you feel now? ,

Here we go. And I thought this was interesting. 31% of us are millennials 31% of boat owners are millennials.

That’s funny. Wow.

So what was the other one was 61% of the annual household income or 64% of the boat owners have an annual household income of 100k or less. That’s either that would be the cost of owning a boat. D Depending on what it is but my little frickin mins of boats.  you’re not near that but anything new, new off the line for sure. , and even, Well, my size both I have 18 footers, but a new 18 footer is  60s  upper 50s It’s nuts. The boating markets nuts.



Do a lot of people buy new or are they buying used cars I see a lot of used boats for sale to Oh apps  Facebook marketplace. Or you can find a used boat anywhere some reasonable some not reasonable of tours. But, it’s funny. I mean, sometimes in high school, I used to Captain this guy’s 36-foot Sea Ray. And it was brand new, but the guy had never owned a boat before that? 

So sometimes you get I feel you just get those guys that are, Oh, I’m just gonna go I gotta go get the newest, flashiest thing, which could be cool.  if you got a captain or if you’re just really dedicated to it, but. This guy that I used to work for, he’d probably bought that thing probably three or four years ago, but to this day,  does not use it. 

Unless he’s got a guy that’s willing to take him out. so he can kick back which I get but, other than just relaxing on the boat, he has zero interest in it. So if I could recommend anybody just buy a used boat, see if you it. , go from there. Start small. Usable. You might run into, a couple more problems depending on how nice it is. But you’re gonna be doing maintenance all day, regardless of the boat. It’s just a boat. 

Breakout another 1000  so it’s crazy. 

Is the engine? Is that the hardest thing to maintain? That always breaks down? 

Kind of It depends. But, usually, it revolves around the motor because if you think about it,  on the one boat, I have a Yamaha which is Japanese. And it’s pretty much a Honda Motor. , in and outboard. But if you think about it, you’re running this motor in the worst conditions running saltwater through it because obviously, they don’t have an external radiator. 

So it’s just cycling saltwater. And just the worst thing for anything metal. And you’re just hoping, hey you’re 60 miles offshore. I hope this thing’s gonna keep going. But no, it’s been good. And I’ve found with the boat rental, that the more you use the boat regularly a car. Usually most times, the more you won’t have to do maintenance on it because you’re running it a normal vehicle. Lot.  probably 90% of boaters are not commercial fishermen or crabbers. commercial fishermen whatever they’re not, boat every day. 

So you got this engine that you’re just letting sit for 28 days out of the month. And you’re just expecting it to keep firing and firing and firing. Meanwhile, on the boat, on a modern bow, you have a million things drawing electricity, you might not have the battery voltage. But even if you do you might need a spark plug, you might need to replace a manifold just eating away these voters. So I come to find that the more often you’re using it, usually the more it’s going to just cooperate with you act a car, you do the maintenance, you get the oil changes, but it’s motor, it’s built to run it’s not built to sit with a corrosive,  laneway water sitting in it. 

And that’s mainly the thing you find is people that don’t use their boats typically tend to just have more problems with it. Sometimes you get that good. Out of the box, a 20,000-year warranty, it’s not going to break down and sometimes you can still break out but, I’ve found that the more you use it, obviously you’re doing maintenance on it more because of oil changes and it goes by hours. Not my miles. But you could probably see, usually out of a good motor, you’ll see three to 5000 hours, which is about I would say I’m sure I’ll go for it before you’re ready to get a new motor just in a car. It’s probably similar to 250 to 300,000 miles. 

Usually so but, I tried to find the best motor which is in my opinion a Yamaha Honda. I have a mercury on the other boat. It’s a 2020 but it came from a crab boat. So it was being used every day, every day getting 200 hours on average a year. It’s four years old and has 900 hours on it now. But that motor has been flawless. I mean I’ve never had Mercury and Uno it’s not Japanese it’s not the normal car you see driving down the road, but it’s been flawless. Been a great motor. Domestic motor. It’s been great.

Cool. Oh, it’s, just sitting in the salt?  

You’re just asking for your rust. And it just goes to show you the Craftsman craftsmanship that goes into it.

What about maintaining it,  if you’re gonna mean if you own a boat, just what are normal maintenance expectations that someone could have?

If you’re a guy looking to get into it, just know that whether it’s new or used, it’s usually called the 100-hour maintenance, which is just a 5000-mile oil change. But you’re going to be doing the oil change filters, gaskets, impeller, which is the thing that pumps the water sucks it from the bottom and shoots it out of the back. , you’re doing that grease everywhere. In my motors minor. I have a 90-horse Yamaha and then the Mercury’s at 115 in here around  678 $100 for that 100-hour maintenance. 

Okay, on average, my boats run out for 50 bucks an hour, give or take. So if you can keep your stuff in line. Make sure you’re maintaining it. Make sure you’re greasing it. You got 1% of profitability in there. A small personal, 100 hours but on average, the average voter does about I think it’s about 100 or 150 hours a year. For me, it’s usually a month, give or take. Okay, so, any year you might spend five 800 bucks if nothing else.  give or take,

Do you do the maintenance by yourself or…?

I don’t, I probably would just ruin everything if I did. Yes. The natural touch hence owning a boat rental company. It just always seems to happen. But  I said, my buddy Aiden, he owns Anchor Marine. He does all my maintenance. I mean, I’ve called this kid at 1 am. Dude, it’s not working. I got a rental first thing in the morning. 

What can you do? So he’s been a godsend for me. He’s a buddy I grew up with in high school. Cool. And he’s been an apprentice for another boat mechanic. He’s probably been in the industry for three to four years and love the guy. I mean, he’s just, any other guy probably would have blocked my number and gone on a suicide watch list with me, but he’s been great. 

I mean, he’s a great guy. You gotta have someone like that. Absolutely. If you got a business that, where it’s just maintenance, man. You got to have that guy. , Stan. , look I’ve got to figure this out for myself. But, it could just, sink the next day motor could fail. But, at least with a guy  Aiden, it’s going to percent.

So where can people rent a boat from you find more info about you follow you? 

Absolutely. If you just look on Google “Marker 26 Boat Rental”. If you’re in the Palm Harbor Area, you can just look up boat rentals near me. I’m usually one of the top 50 that show up. But market 26 boat rental.com Or my cell. You’ll see it there on the Google page. Cool usually.

And what two boats do you have now for I have an 18 foot?

Aqua sport and an 18-foot Aqua sport. Two boats do the same thing. One’s got a little bit more power. One dozen. They both go perfectly, though. So it just doesn’t when you go out on it. It may have just been worked on the whole night previously. Just to fit you for that day. Yes. So that’s the craftsmanship that we do at the marketplace. 

Yes. Always maintaining. Absolutely. I love it. Jackson, thanks for being here, man.

Thank you. Thank you for having me. Absolutely.



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