Interview #14 David Simmons-The Call of the Ocean: A Journey of Reinvention

Transcript, May 13, 2025

Rick Barron (00:01.189)

Hi everyone. I'm Rick Barron, your host and welcome to my podcast. That's life. I swear. 

My guest today is David Simmons, a former high-tech executive who swapped the corporate life for salt air in the turquoise seas. 

Growing up surfing the waves of Santa Barbara, David always had a deep love for the ocean. Now after retiring, he took that passion to the next level. What do I mean by that?

He launched a very successful charter tour sailing business in the Caribbean. Today we're going to explore his bold journey of reinvention, the realities of navigating uncharted waters, and what it means to truly follow your dreams. 

Please join me as I have my conversation with David Simmons. David, welcome to the show, my friend.

David S (00:55.224)

Thank you, Rick. It's great to see you.

Rick Barron (00:58.393)

Yeah, I just thought I'd share with the audience. The last time I saw David was about 22 years ago, and I think we both shared it. We don't understand where the time went. And the way I the way I found you, David, was I was just cruising or cruising Facebook one day and I saw one of your postings and I thought, wow, he's got a sailboat. 

What's he doing out there? At first, I just thought you were on a tour with someone else. then I realized as time progressed, I thought, I don't know, this guy has started his own business. So that's what really prompted me to want to get some time and talk to you about how you got into that. But now are you originally from California?

David S (01:44.238)

Um, I like to think so, but actually not. Um, I was born in Jackson, Mississippi, and, uh, my mother was a Californian who married a, uh, a sailor in the Navy and, uh, they met in San Diego and, and it was, we ended up eloping and moving to the deep South for a few years, but it was a very stressful time in 1960 through 64 in in the deep south and my mother really didn't want to raise her kids in what felt like an unhealthy environment. 

And so she grabbed the kids and jumped on a train and made way back to California. So, I've been in California ever since, but I still have lots of family in the deep south and some great memories of fishing and hunting and hanging out with close family and eating good food in the south.

Rick Barron (02:29.435)

I like it. So I understand you grew up in Santa Barbara and I guess you spent a good portion of your time living there or where else did you live besides Santa Barbara?

David S (02:54.284)

Yeah, we moved there when I was about nine or 10 from, I don't know, I think we were in the LA area. My childhood was a little bit tumultuous. In 1970, my mother enrolled at UCSB to get her PhD or work on her degree, eventually her PhD in medieval history. And she was a widow by then because she'd remarried and my stepfather had passed away. He crashed on a motorcycle. yeah. 

So, you know, she bought a little small modest home in Santa Barbara near the ocean. It's probably worth, it's definitely worth a couple million right now. And I grew up there and she was busy and I had two brothers and the three of us got in a lot of trouble and had a lot of fun. 

Eventually my mother decided she wanted to complete her PhD work in England or France and we ended up the whole family moving there and we moved to London and both my brothers were in school there and I took the year to travel in Europe and North Africa, I actually spent a winter in Morocco and southern France and Spain surfing, so that's kind when I got my travel bug was during that time living over there.

Rick Barron (04:14.801)

You know, it's just about to say it sounds like you've been around the world. I think I read somewhere, I don't know what was your website, where you've took, where you have surfed, you've done deep sea diving and boating in places such as Europe, Mexico, Africa, Hawaii, Central America. So how do you describe that adventure? I mean, going to all these places at that time, I guess when you were fairly young.

David S (04:45.068)

Yeah, so my travel was kind of bookending my career and my family time. you know, out of college I traveled quite a bit. Again, my mother was in Asia at that time and I spent time in Southeast Asia at her place after I graduated. And I just, you know, always loved the water and got scuba certified.

I mentioned to this a while ago that I actually was a whitewater rafting guide too for about 10 or 12 years. I met some really good guys in the Santa Cruz area that ran their own boating business and they taught me how to be a guide and I spent many years with them on weekends. When you and I were working at Sun, I'd go away and do trips down all these California rivers. I just kind of always had a...

I don't know, a need to be outside, to be in the water. I find the water's really, I don't know, it soothing and, and healing and exciting and all of the things combined. And of course, surfing in Santa Cruz was a revelation for me because Santa Barbara is quite small and protected and doesn't get much in the way of big waves. And then you get to Santa Cruz and it's like, my God, that the waves are huge. The water's freezing.

There's you know, giant sharks in the water and it's just, it's so intense. And, you know, I, I don’t know, I, I did that for a while too. And so, yeah, that's, that's kind of where I got the love. And then, you know, I, I worked for, I can't believe it, 30 years in tech of which 21 were with you and others at Sun, where I also encountered a bunch of great people. 

Had some really fabulous bosses that, I learned so much and love son so much and, you know, and then, started a family and, know, started doing long commutes and didn't have time for that much, you know, travel and exploration, but, I didn't, I didn't quit doing it. I just did it a lot less. Yeah. So, after I retired, I, I just kind of gravitated right back towards the stuff I love.

David S (07:05.89)

I had lost a little bit of that enthusiasm and excitement and feeling of adventure in the many years of long commutes and long work hours and all that stuff. And I just decided it was time to try and recapture some.

Rick Barron (07:22.811)

Did you always have this dream that one day you wanted? To buy a boat and it wasn't right after you retired and if you like, OK, what do I do with myself? Because it wasn't until I saw those photos on your Facebook account that I started seeing this guy, he sure goes down there a lot and I mean, that's a good piece of traveling. You know from Santa Barbara to the Caribbean. But when did you get that bug that you know this is what I want to do?

David S (07:51.926)

Yeah. a lot of people assume that I must've been a sailing guy in my whole life because I bought a boat and I've been living on it. But the truth is, is that I was a seasick surfer. I, I would go out on dive boats and fishing boats and I'd be like, my God, I got to be sick. 

You know, because there's something about the way those boats, you know, heal and, and handle and in, in the surf, know, when you're sideways to the seas and you're on a boat full of live bait and diesel smoke and you know looking down at your gear tying your fishing lines or putting on your scuba stuff that always made me feel nauseous. just thought I thought I was cursed with seasickness and I still dove and I didn't fish that much but I still went out on boats to dive but I really didn't like being on boats.

It was kind of pure chance how I got the boat bug and some friends of mine, one of my best friends and we go every year, we have an annual boy backpacking trip. I think we're going to do number 43, you know, this year and it's kind of morphed, right? And it's not just backpacking, but we decided to charter a 45-foot Beneteau, a monohull and out of Long Beach and we sailed to Catalina for four days.

It was right at the beginning of COVID and, you know, there, there were all these fires up in Santa Cruz. lost 900 homes up there in Santa Cruz in the community. And, like the sky, even all the way down there in Santa Barbara area or the Channel Islands was, was red, you know, within brown with the smoke. And so, it was kind of surreal. 

And we went out there and I just remember that feeling of the sailboat, you know, being under sail and how stable it was and how beautiful and peaceful, know, without the engines and you know, I always thought sailing was going to be kind of boring, but there was so much going on. And so, I have sailed small boats and catamarans and things like that. But I don't know. It just, it just got me. And one of the things that got me, was like at night, I didn't like being below deck. 

I still don't really love being below deck, but I hung my hammock on the, jib to the mast and I spent the night looking up at the full moon swinging in the hammock for a couple nights and it was just magical and I just asked myself why am I not doing this and so that started me on my journey and I back in Santa Cruz I was teaching high school then and things were shutting down because of COVID and I started taking all of the American Sailing classes ASA 101, three, four, five, six and then eventually 114, which is catamaran sailing. 

And at the same time, I did a couple of charters in the US and British Virgin Islands over the summer because as I was teaching school, I had summers off and I actually had a rental place that required me to be out for the summer because they turned it into like a really high-priced beach rental, but I got it for cheap during the year. So, I had to disappear for three months, right? And so, it was perfect. 

You know, I got time off work. Gotta leave my place, buy a ticket, I'm heading to the Caribbean or Mexico. And I just spent the summers going and checking out boats and doing some chartering with a good friend of mine. And that's when I realized, you know, I want to buy a catamaran. And the catamaran's different than a monohull. It's just got a lot of space and it handles different and purists don't always like them. 

But for me, it's you know, I don't get seasick. Like once or twice, like probably twice in the last three years when the weather's been really

Rick Barron (11:46.747)

Yeah, was going to ask you, you know why the catamaran, but I think you already answered that question. So, before you started your charter tour business did you have the mindset; I have to get all this training and understand that the various idiosyncrasies of what it takes to sail a boat before I even begin to think if I can start my own business. I mean, did that all happen prior or was it kind of in parallel?

David S (12:22.176)

You know, I just kind of, could, I didn't really have it in my mind to start any sort of business yet. I mean, was probably, it was in the back of my head that boats are expensive and it'd be nice if I could make some money with my boat. But I took all of the ASA courses because I just wanted to know what I was doing and I wanted to be able to charter boats and not have to pay a captain wherever we went. I wanted to be captain, you know, I like it. like sailing and I like being in charge. I wanted to be the boat captain and I wanted to know what I was doing. I took all the ASA stuff, but I also decided to get my merchant marine credential, the MMC. They call it a six pack because you're a captain's license. I'm allowed to take it to Coast Guard.

Rick Barron (12:59.119)

I kind of got that notion.

David S (13:21.262)

License allows me to take up to six passengers on an undocumented vessel. So, something that's not like a ferry or a commercial boat, I could take them out with the license. it was a lot of work and I did it online and it took, you know, like eight or nine months to do it while I was sailing through the Caribbean. I was online all the time. And in the end, you take proctored exams where they take over your computers and make sure you aren't, you know, looking at notes or the internet. They watch you and then you have to send in your work, all your notes and copies of your, the chart plotting that you do. And it was pretty extensive and I learned a ton. And now I'm working on my master captains, which is, so you have to have 360 days of sea time for the first thing. And that's a lot, right?

And then you have to have 720 to get your masters. And so, I'm pushing that right now. I think I'm there because in the last two and a half years, I've, you know, when you live on a boat, you can self-certify a bunch of that time.

Rick Barron (14:32.145)

When you talk about getting your license, is that like getting a driver's license where, okay, you have to renew it every four years or is it just one time and it's like, you're good to go now?

David S (14:43.948)

No, you do have to do some renewals, but usually if you keep it current, you don't have to take like the exams all over again. There are some remedial stuff that you need to review. You also have to get an extensive health certificate and do drug testing and all that like every two years. So, they're really trying to make sure that people with commercial or even non-commercial captain's licenses are safe and healthy. And that was part of the process too, know, and then going back and I had to find a new doctor and do a whole bunch of tests and whatnot. And so that was interesting.

Rick Barron (15:27.441)

So, when you arrived at that time where you felt like, I'm ready to take this casual sailing now into a full flown business, what was the process of getting that started? And what did you learn along the way as you were doing all that?

David S (15:43.426)

Yeah, well, it's been a journey and I know you introduced me as highly successful and I'll take that, but it's also a bit generous because my business is still nascent and you know, for me...

David S (16:02.702)

What I had struggled with is like, okay, am I a circumnavigator? Am I someone who's going to circumnavigate the globe because I can, because it's a challenge and I'll learn so much and it'll be fabulous and I love sailing. Or am I a charter boat captain that makes money by chartering my boat and other boats? And there's really three kind of business opportunities for a captain. You can charter your own boat and take people out on it, or you can be a captain on other people's boats, even like just for rent for the week, and just be a captain for hire, or you can do boat delivery, and that could be long term or short term. You could just move a boat across the ocean, or you could manage a boat for someone who's got a bunch of money, but can't be on the boat all the time, but maybe wants to fly to someplace every two months and have you take them sailing for a week or two.

To me that sounds like a super sweet gig and I haven't found one yet but I've met some guys doing some pretty amazing stuff and they're super seasoned and yeah, they're few and far between but man, I met this one guy, he was sailing a Sunreef 80, which is huge, 80 foot, top of the line, primo cat. I don't know how much I it was worth, like 10 or 12 million and he was...

I think he was Norwegian and he takes care of the boat, him and his girlfriend. They move it around for him and when the owner and his family come on board, they take care of him. When he's gone, he just keeps the boat in ship shape and enjoy it, living on it. There's some pretty incredible opportunities out there. For me, it's evolving. I don't really have a... I'm not locked into any model yet.

That's the good news and the bad news.

Rick Barron (18:02.521)

I see. So, there's a lot of options more than I could have imagined, to be honest with you.

David S (18:08.812)

Yeah, I've done a little bit of the two things. I've had people on my boat and taken them out. I've done a lot of that, though I've only had a handful of paying customers that kind of went through the whole, let's sign a contract and get you provision and do all that. I've also been doing sort of informal charters for friends and family friends and things like that for a while. And those are always fun. I love doing that.

The perfect charter guests for me are not people who want to be weighted on hand and foot, but people who are like-minded, you know, people interested in sailing and having a good time. And I know there's way more money in the very, you know, high end, high touch, but I need more crew to do that than just myself. And that's not really my target audience for, for things.

Rick Barron (19:02.619)

Well, yeah, I I think I don't know if it's called, you know, your limitations, but you know what you have a real passion for that. Yeah, I could do this, but am I going to be happy doing it?

David S (19:13.23)

Yeah, that's right. I've also asked about things I've learned. One of the things I've learned is that it's hard to make your boat your home full time and your charter business. There's not lot of extra space. Just to keep it clean and tidy and welcoming for guests, really have to just isolate your stuff and your living, you know, and you have to create some guest space that's really theirs. And luckily the catamaran I have allows for that because one side of the boat is my side, the other side is the guest side. And so, there's a nice, you know, we have shared living spaces, but they have their own space. So that works out really well.

Rick Barron (20:02.853)

I notice on, again, looking at your Facebook account, I've seen a few pictures where you're kind of tinkering with some of the parts of the boat, so to speak. I guess where I'm going with this, and I think you kind of alluded to it, it's almost like it's like a 24 by seven operation because there are things you have to do in preparation for your guests. You have to take care of the boat. And I guess you've got to be a Jack of all trades when you're dealing with boat parts, I would imagine because sometimes you just can't take it down to your local hardware store and say, hey, can you fix this for me?

David S (20:41.326)

No, that's understatement of the year. Yeah, if you don't like to work on stuff and if you're not handy and a problem solver and like using tools and stuff, don't buy a book unless you've got an endless credit card and hire some people to work on it for you. 

There's always stuff that needs maintenance and there's times when things break and sometimes, they happen like in threes and tens when like everything's just going wrong and you're going, my God, get me off of here. But I've always enjoyed building stuff and working with my hands. And I taught robotics in high school and I ran a factory at Sun and before Sun for 10 years and I've worked construction and all that. I do like fixing and building.

Luckily this boat I had, like so many tools, the previous owner was kind of a tool freak like me and so I've got like a tool for everything except for a good multi-tool. And so yeah, I'm often fixing things and sometimes I'll post like 10 pictures of me working on stuff just to remind people that it's not all rainbows and unicorns. you know, sometimes it's hot and messy and stuff's not working and you just got to get it fixed. There's not a lot of debate, whether it's your anchor, your windlass that raises your anchor, you can't not have it working. It's really hard to pull up 300 pounds of chain and another 60 pounds of anchor by hand every time you drop anchor. You got to get your stuff working.

Rick Barron (22:31.197)

So, it's a lifestyle that you can't sit there and wonder what you're going to do. No, I got to figure this out. I mean, I have to imagine that there's been moments where you've been out in the middle of the ocean and something happened. It's like, how in the hell do I get back to port now? 

Has that ever happened to you?

David S (22:51.822)

Yeah, I've had a couple. mean, people think that sailors like me who've traveled 10,000 miles in the last three years spend a large amount of their time in the open ocean. the truth is, know, it's 98 % of the time I'm within sight of land, you know, because you know, the Caribbean has got so many islands, you know, beginning with the Bahamas, which is not the Caribbean, North Atlantic, you know, all the way down the Bahamas for hundreds of miles. 

There's like just the Exumas. There's a stretch of islands in the Bahamas. There are 650 islands in the, just the Exumas. So, it's a hundred mile stretch of island. There are 650 islands. It's, it's fabulous. It's an ocean and land sea wonderland. It's called the Land and Sea Park.

Most of Exuma is and it's the most stunning clear water, blue water I've seen. You can see it from space. It's so insane, the Mahama Banks. But anyway, the point is that you're almost always within sight of land unless you're making a big passage. And fortunately, you know, 95 % of things that go wrong, go wrong when you're inside of land. 

And, you know, you get to an anchorage, a safe anchorage or marina or whatever, safely and then you can deal with it. But a couple times I've had stuff go wrong. Once we were in, were actually my first week in the actual ocean outside of Chesapeake when I bought the boat and stayed in the Chesapeake for two months, basically learning how to single hand sail the boat. Chesapeake has 12,000 miles of shoreline. It's incredible. It's such a big bay and it's beautiful. It's easier than being in the ocean when you're learning.

So, the first big sale I did was from Hampton, Virginia, out the Chesapeake and around Cape Hatteras, the graveyard of the Atlantic, and then 800 miles south, including crossing the Gulf Stream to Marsh Harbor Abacos. And I did it with two other crew that I had just met. And it was a six-day passage. 

And about midway, we were about 300 miles offshore and we lost the bolt that holds the boom into the mast fell out and it was because we were, because my handheld Garmin, I turned it on and it overrode the settings on the autopilot at the helm because they all talked to each other, Laurent, Simrad, Garmin, and turned the boat around into a really stiff wind and high seas and it slammed the boat around so much it knocked this pin out. 

And so, we had to figure out it was jammed and we had to get it loose. We had to put new bolts in and nuts on it and do all that in the middle of 35 knot winds and 12-foot seas and yeah, and turn the boat around and keep going. You know, and we ended up three days later flying into Marsh Harbor with a tropical storm, Nicole kind of breathing down her neck and you know, it was exciting. It was exciting, but you know, it builds your confidence when you, deal with these problems.

Rick Barron (26:18.641)

I would imagine you have to have a steady mind knowing that this is no time to panic. 

David S (26:26.85)

You know what, I'm glad you mentioned that because for some reason, I have this thing where I stay calm when everyone else is panicking. And the other thing I do is like when there's a fire and everyone's running away, I kind of walk towards it and like, okay, does somebody need help? I'm not saying I should be a firefighter. 

I'm not, but yeah, even in rafting or whatever, I've learned that there is really no situation that panicking will make better. And that's the thing you learn scuba diving is that whenever something goes wrong, you stop. You stop whatever you're doing. You a, breathe, right? You got to take a breath because you're underwater and you think, what is the problem? What am I going to do about it? 

And if you can do that in you know, a crisis or what could be a crisis, you can avoid it or you can deal with it. that's, I think one of the things that's important if you want to do what I'm doing is you do have to have the ability to just sort of like look at things analytically and calmly and sort of like, okay, what do I need to do to fix this? Yeah.

Rick Barron (27:49.137)

Absolutely. You said something I want to go back to just briefly. You were a teacher?

David S (27:56.206)

Yeah, well, yeah, so after I retired from Oracle, because know, Sun acquired Oracle and I was there for eight years at Oracle, and I retired in 2018, I didn't really know what I was going to do next. And I did some volunteer work around ocean stuff. And I was like, OK, well, what's going to bring me inspiration and be useful to people?

Rick Barron (27:57.123)

I didn't know that.

David S (28:26.454)

And one of the things I tried was I tried substitute teaching for a little while and I tried some younger years and I'm like, no, shoot me, right? And then I ended up filling in at high school at the San Lorenzo Valley SOV High School in Felton and they had a computer science and robotics program where they'd lost their instructor, founder and, I filled in for a few weeks and they asked me if I was interested in the position. 

And at first, I said, no, there's no way I can do this. There's way too much. then, so they had me interview some candidates and I thought I can do better than these guys. I'll take the job. And so, I ended up doing that for four years. ran their computer science, robotics and AP computer science classes for a few years.

Rick Barron (29:17.627)

Wow, that's amazing.

David S (29:19.278)

And then COVID hit and everything changed. It was teaching remote and then kids with masks and they started, enrollment was down and they started cutting hours and classes and fun. And I just couldn't do it anymore. So that's why I decided to go sailing.

Rick Barron (29:34.383)

Yeah. Well, those are some tough years for a lot of people. Now, I think I saw on your website, where you promote your tour business, that you also provide boat delivery services. I think you mentioned that early on, but I didn't know you actually do that yourself.

David S (29:56.386)

Well, so it's aspirational. I basically have the skills and the credentials to do it, but I haven't done any boat delivery yet. But those are the three services that I promote in my business is, you know, I'll be captain on your boat or your charter boat. So, I have friends in Australia that I was over there with another friend on a trip last January, not this one, the one before.

They said, well, we're chartering a boat in the Whitsundays in the, you know, the Southern barrier reef, but we don't have a captain and you're going to be over here. Do you want to come captain our boat? And I said, well, sure. So, you know, I went and did that for them and it was fabulous. I loved it because it wasn't my boat. You know, I can take good care of it, but you know, when shit broke, I was like, yeah, I'm taking it back and I'm going to tell them this isn't working and it's not my problem, you know, and, and, I loved doing that and I've done a couple other trips. 

I've done it in Mexico and Virgin Islands. I've done a couple of short trips where I've acted as captain for friends and family and whatnot. I have not done the boat delivery thing and it depends on what kind of boat it is and how far. 

If it's a boat that's very difficult to single hand, then of course I'd have to have crew and if it involves overnight passages of any significance, I would have to have a crew to help because it's, you know, maritime law says you always have to have someone on watch. And I can't stay awake for four days, for 25 days.

Rick Barron (31:45.105)

Right. Now in, in, in the time you've been doing this business, even with your, uh, adventures prior to starting a business, I have to imagine you've come across a lot of individuals who are like you. They love being out there in the ocean. And I know you mentioned a couple that were taking care of a boat because it was like, a dream to be.

David S (31:58.531)

Yeah.

Rick Barron (32:14.097)

Can you share a story or someone that really was a big influence on you as you've been sailing thus far that really had an impact on, gosh, I was fortunate to have met this person because he or she gave me so much insight into the world of sailing that I thought I knew, but I've learned something from them.

David S (32:42.286)

Well, there's one entity that has taught me more than anything and her name is Mother Ocean. 

And I will tell you, my first year of sailing, I had a motto, which is I learn something new every day, every single day. You know, whether it was big or it was little, it's just stuff would happen, you know, it'd be like, yeah.

I didn't, I didn't press the latch on that cabinet in my bathroom before I made a passage that day and the seas got big and that cabinet door swung open and all of the chemicals in there fell on the floor and one of them cracked and leaked boat polish all over the floor. And then I came in to go to the bath... And then I came in to go to the bathroom and I tried to clean it up and it was slippery everywhere and it made me nauseous and I almost was seasick for the rest of the trip. 

And then when I cleaned it up, I, you know water got in, the shower overflowed and it made the slipperiest surface on the planet of the earth and I almost fell and broke my neck. You know, it's like, it's like all it was, was that one button. I didn't press that one button. I didn't latch that cabinet. didn't secure it before making way. And, and I could have broken my neck or whatever, you know, I seasick for 24 hours and, and stuff like that used to happen to me every day. Or maybe I didn't quite tie a knot, right? I was lazy or something like that. 

And then that knot came loose and that line could have got caught in the prop and then I would have lost steering on my boat as I was going through the harbor and would have rammed into all the boats on the dock. Stuff like that would just happen all day long to me. And the key for me is that you've got to make those mistakes to learn. And it's just time on the water and I see now why the captain's license requires 360 days of sea time. 

Because you really can't have that experience if you don't spend the time and make the mistakes and pay attention. So, I would say that is probably the biggest teacher to me is just experience. With that said, there's a couple of standout folks that I've met along the way that I've cruised with.

But you know because I'm a solo sailor and a lot of the people that come on my boat aren't that experienced It's hard for me to learn that much It's more of a challenge for me to teach them enough to be of use on the boat and to also feel useful Which is something that's really important when you have people on the boat you need to do it So, you know, yeah, there's a handful of guys. 

I've learned some good stuff with my brother, my older brother Jerry has come on the boat multiple times with me and he was a sailor before me. He owned a small Catalina, but it's completely different. And we learned a lot about working together because he's my big brother, you know, and he's a sailor and I'm not, and you know, and he had to learn, no, I'm the captain and I own the decisions. And so there was some really interesting power plays, but you know what? He is great crew and I'm a better captain for it.

Having had him on board multiple times. And anytime I need him, he's retired, I can call him up and he'll come down and he'll help me move the boat. You know, I sailed from Bonaire to Puerto Rico with him. my God, it was such a rough ride. was four days across the Caribbean from Venezuela, basically up to Puerto Rico. we had rough seas and high winds and we were actually pointing to the Virgin Islands. We couldn't make it because the wind was too northerly and we ended up in Puerto Rico.

It ended up being fabulous because the Puerto Rico Virgin Islands are so cool and nobody knows.

Rick Barron (36:57.039)

Yeah. So, you were working in the Caribbean for quite a while. Now you, you took a pivot and you went to Panama. How did, how did that come about?

David S (37:06.542)

Yeah. You know, I had made the circuit around the Caribbean to, know, there's the northern, you know, the Antilles and then there's the leeward and the wind words and then the ABCs, they kind of circle the Caribbean and I don't really like staying in one spot for extended periods unless there's something there really fabulous. And I'm always looking for that next new adventure. So, I had gone, my first goal was to get from the Bahamas to the Eastern Caribbean. And that's quite difficult. It's known as the thorny path. most, a lot of sailors say, you can't do it. You got to go to Bermuda and go straight down if you want to go to the Eastern Caribbean. 

You can't go down the Bahamas and sail into the trade winds. But there's a way to do it and it's pretty well documented and it's tricky. And it took me six weeks but I got it done. And then once I was in the Eastern Caribbean, I was kind of in a hurry to get down to Grenada because of my insurance. I have to be south of 12 degrees after July 1st. 

So, you know, I had to blow through the Eastern Caribbean and there's some fabulous islands along the way, you know, English, French, Dutch, colonizers, and a lot of them are still independent, the French still hold a few territories that are actually arrondissements in departments of France, know, like Martinique and whatnot. But they're interesting and I had a good time, but I was in a hurry and I liked Grenada a lot, but after a while I kind of just you're kind of restricted to Southern Grenada. I got a little bit kind of bored with it. 

And so, I decided to go check out the ABCs and Aruba, Bonaire and Curacao are really unique islands. They're right off the coast of Venezuela, about 30 miles, and they're very dry and the water is super clear and some of the best diving in the world and they're Dutch territories, but they have a really unique culture, speak Papamiento, it's the only two countries in the world, Bonaire and Curacao, where they speak it. It's combination of African, Portuguese, Spanish, English, and Dutch. And it's just a really amazing place. And Bonaire, the island of Bonaire, the whole island is a marine park with like over almost 100 dive sites just on the leeward side. 

The whole island is, you can't drop your anchor, have to pick up a mooring ball, you could dive, dive, dive all day long. Love it there, I had a really great time. And Curacao's different. They live off extraction industries there. They've got, Bonair had a bunch of salt mines. I mean, they were called the useless islands by the Spanish. they used them basically for, well, the Dutch took over and used them for slave transport.

They moved eight million African, West Africans to Brazil through Curacao. And over in Saba, they moved six million to North America. you know, in Curacao, they have giant oil refineries, I enormous oil refineries, and they're usually doing Venezuelan oil. The sanctions complicate things, but anyway.

I really loved being in those places and I've had friends and family come and stay and I would say if I was to put down roots somewhere that I would definitely consider those places. They have kind of a European lifestyle and standard of living, fabulous weather and water. I'm not sure what the immigration restrictions are, but I wasn't ready to settle down when I went through there, but I really love those places. 

But again, I wanted to go back and see, you know, other parts of the Caribbean that I had to go through in more of a hurry. So, my brother and I, went, we went back to the Puerto Rico, the U.S. Virgin Islands, and I wanted to do work on my boat. You're always working on your boat. I had to get my boat hauled out and bottom pane. And, you know, I had about 20 grand worth of work done on the boat in the BVI's. then I went back and did that whole circuit again. And by the time I got too curious, thought, well, I might as well go see Aruba. 

And Aruba is totally Americanized and it's okay, you know, it's got its charm, but its kind of wasn't a place I wanted to stay. So, I was like, well, where to now? I guess I'll keep going west because that's downwind and I'll head to Panama. And that was a quite an adventure. That was five days. 

And, you know, it goes along the coast of Columbia, Venezuela and Columbia, and I'm not allowed in either of those countries for insurance purposes, because there's not a lot of safe anchorages, and there's some piracy and crime. And so, it was five days of traveling downwind with a young Austrian man that came with me. We had a great time.

Rick Barron (42:34.193)

You know, this listing to you describe the various islands, places that you've been to the people. Did you anticipate this is what it would be like when you went down there to start your business and to start sailing to various parts? Because the way you are describing things, I could just hear the excitement in your voice and in your face that it displays these places just resonate or resonated with you that it's like, wow, this is even more that I could have hoped for.

David S (43:10.604)

Yeah, you know, for me, I love the natural beauty. I am just stunned by how much natural beauty there is in these places. And I love being in the water. I used to spend two or three hours a day just with my, know, I do my work on my boat, you know, whatever I need to do my shopping, do some chores, go online, because I'm Starlink, so I'm super connected. But I will always save like an hour or two, sometime during the day to just jump in the water with my snorkel gear and my GoPro and go look for stuff. And I'm never disappointed. I mean, I always would see something, especially in the parts of the Caribbean before. 

There are a few places that are, it's just murky and rough, kind of like parts of Panama I'm in right now. But man, a lot of these islands I would go to, I would hop in, know, and I'd see Caribbean reef squid or a slipper lobster or a couple of, you know, really beautiful, you know, southern stingrays or a couple of turtles, you know, snacking on the bottom or maybe a nurse shark asleep under a ledge, you know, or these really friendly, cute trunk fish, you know, one of my favorites and just...

I can name them all. I mean, it's like I made friends with them. It's like I know them, right? And I don't do that much fishing, spear fishing. Occasionally I do, but I don't like random line fishing where you have a lot of bycatch and stuff. 

I'll take fish either deep sea or, I'm sorry, trolling for specific species or going and spear or something that I know what I'm taking. yeah, just, I'm in love with the wildlife and the beauty and I fly a drone for some great aerial shots and that keeps me busy. The people, I meet a lot of really nice people but I all because I don't go into marinas and pay for a slip on a dock, I anchor for free in like a beautiful anchorage and

David S (45:23.274)

Everybody has space, you know, you don't park your note your boat within speaking distance of the next boat unless you want to crash into them, right? And so, you know, you're you only have a chance really to engage with other sailors and people on shore when you make the opportunity and you get in your dinghy and you go to a dock and you walk to a restaurant or you go to an event that you heard about on Facebook or something and  there's some really cool sailing communities like in Curacao. 

There's a lot of fun community activities we would do, know, sundowners we call it where we'd have a little bonfire on the beach and share some food and drink and someone bringing guitar and you know, that'd be fun. I mean, I love doing that. 

We had trick-or-treaters in Curacao that all the kids would come on in dinghies to the back of your boat all dressed up looking great because people spend the whole, you know, hurricane season in Grenada and Curacao because they have to because you can't be in the in the hurricane pass. so that whole stuff, had no idea what that was going to be like. And it's really joyful just to discover these things along the way.

Rick Barron (46:35.041)

In the time you've been down there, you know, from the time you made that transition to go to the Caribbean and starting your business and where you are today.

What have you learned about yourself? What thoughts flowed through your head that while I was here and now, I'm here and in between that, I learned the following about yourself. What sticks out?

David S (47:03.938)

Hmm.

David S (47:09.294)

That's a really good question.

For me, the last four five years have been really transformative.

You know, I think being in sort of the Silicon Valley, you know, hustle and bustle and, you know, pursuit of status and wealth and recognition and all that can be distracting from some of the other rewards of life, like family and friends and community and personal sort of health and peace of mind and serenity, you know, a lot of that stuff. I traded some of those things to get ahead and save enough money to go and live my dream, you know, and some of it was a conscious decision to defer and to reprioritize and some of it was unconscious. 

But what I realized is that you know, some of the things that are available in life are priceless. You can't put a price on them, whether it's time with your kids and your friends, or doing things in life that inspire you and that create a sense of wonder and awe. There's something about looking up at a starlit night and seeing the Milky Way in great detail and stuff to just remind you of our place in the universe. And for me, being in nature is kind of that cathedral, you know, for appreciating those things. And in some ways, it's like I appreciate the miracle of my life by seeing how insignificant it is in the scheme of things. 

And that's one of the things that that this adventure has brought to me is that sense of wonder and awe, again that maybe I had when I was a kid or younger. The other thing I've learned is that I like my alone time, but I am a social creature and being alone and isolated for me, there was a time and a place when I was learning so much and I was seeing so much new stuff and I had friends coming and going and using like Facebook and stuff, I'm able to share what's going on. And that whole discovery and learning process was enough. 

But now that I've kind of matured into it or whatever, I'm more comfortable, I know, you know, some of the challenges. I'm really just craving, you know, being part of a community again and, and, you know, having some relationships. You know, I have friends back in Santa Cruz that I really miss.

I got a girlfriend back there I want to go spend time with. I realized that I can't be this lone wolf guy sailing around solo and taking on occasional charters or friends and really be content with that indefinitely. I would love to circumnavigate. I'd love to go through the canal, go exploring Costa Rica.

And they made me head down to the Galapagos and then do the passage over to the Marquesas and up to Tahiti and Fiji and Tonga and whatever and keep going. But not alone. Not, not without, you know, some crew long-term and a soulmate to share it with. And so, you know, I, I wasn't ready for that three years ago, but I kind of am now. And it's just taken me a while. It's a process that I had to go through. 

And, you know, now I'm trying to figure out what's next and maybe my boat business shifts over time. As I mentioned to you, I'm going to be doing sailing instruction in Santa Cruz at Pacific Sail for at least the summer into the fall. And I expect to learn a lot, make some contacts. I will be back in Panama to do periodic trips on my boat, hopefully with clients. And then beyond that, it's hard to tell.

I think if I do go do the South Pacific thing, it's going to be a little while and probably on a different boat than this one. I love my boat. It's a great boat for what I'm doing. But if you're going to go cross the biggest ocean in the world, know, there's certain things you want in a boat that maybe this Caribbean queen doesn't have.

Rick Barron (52:04.537)

Maybe that's a dream that will come one day. You know, you don't know what life is going to throw at you. I mean, it could happen next month for all we know. But there was one other question I wanted to ask of you. Again, I think I saw this on your website. It was regarding a poem by Charles, I hope I get this right, Bukowski? OK, and you said that you loved it because it resonates with you. Can you share what that means? Only if you want to.

David S (52:44.012)

Well, no, no, no. I don't want to pretend that I'm some deeply-read philosopher who has chosen Bukowski as my guiding light. I'm more of a Facebook Reels viewer who sees something, a squirrel, I go, that's a cute squirrel.

The thing that resonated about the Bukowski quote, I probably should have reviewed it, it's something along the lines of, don't ever let life's challenges and pressures rob you of living a full life. And basically, always strive for living the fullest life you can and finding your joy, finding your place in life. And sometimes you're going to feel beaten down, but don't ever give up. And I mean, I'd be quoting it right, but I think it was along those lines. I also saw, what's his name? Gosh, I'm drawing a blank on him. He's an actor. He was on Jurassic Park. He's a, he's a comedian, yeah. Anyway, basically he was saying, you know, the way he views life is that life is like this, this torch, this beautiful, you know, flaming torch of beauty and light and excitement. And, and, you know, he doesn't feel like aging is like your torch dimming and snuffing out.

Rick Barron (54:11.985)

All right. But yeah, go ahead.

David S (54:37.112)

He feels like you keep carrying that torch until your time is over and then you hand it to the next generation to carry it and to keep it bright and exciting. that's inspiring to me too, being a parent with kids, with wonderful kids and just hopefully passing on some of my insights and joy to the people around me and my friends and clients and everybody is that life is like this fabulous, you know, fireworks display and you know, my time is to celebrate it and hand it off to others, you know, when it's their time and that's kind of how I want to live my life going forward is to not, you know, don't fizzle out. Don't, don't give in. Don't, you know, lose your, your joy and your sparkle.

Rick Barron (55:29.115)

Yeah. I mean, you're only here really in reality, kind of like a blink of an eye, because you think of how many people have come before me and how many people are going to come after me. It's yeah, it's it's, when you, when you break it down into years, days, hours, minutes, it, you don't want to have to look back and say, man, I could have done it, but I didn't. Why?

You know you don't want to have any regrets. You know, even if you attempted even if you attempted and failed, you know you learn from the failure. You do.

David S (56:01.486)

That's right. Yeah.

That's right. No, you remind me of a quote. So, I'm going to plug a YouTuber that I really love. His name is Colin McCray and he's got a YouTube channel and he sails his boat is called Parlay and his sailing channels Parlay Revival. He's a Kiwi and He was on life below deck. I guess he's super yacht engineer, you know young guy So cool, so smart bought a hurricane damaged Lagoon 450 and the beavers and fixed it up and he's been sailing it going for about four years now and I love the guy every week. He puts out a new episode every Sunday and he says in the beginning of is the opening is that it's not the things in life that you did that you'll regret. In the end it will be the things you didn't do. And I agree mostly. We all have our regrets about things that we did wrong. But the truth is that I don't want to regret all the things I never tried that I really wanted to because it's now, baby. This is it. Go try it. See if you like it. If you don't, move on.

Rick Barron (57:19.057)

Well, it's like, you know, really quickly, when I turned 75, my wife, God bless her, pulled together a birthday party for me at our house and had so many people over here. prior to people showing up, she said, Oh, I want to show you something. I said, okay. So, she was decorating the whole house of balloons and everything. She took me into our living room and over the, the fire place was this big banner is saying, happy 70th birthday. David, when I saw the word 70 or the letter 75 or the number 75, me, I thought, dang, I've arrived. And it made me think, not that I never thought about it, but just it hit home more to make me understand, brother, you got a lot of living to do and don't waste it. Do not waste it.

David S (58:14.616)

No, that's absolutely right. A very good friend of mine just turned 70 a couple weeks ago and I was at his 70th party and all the stuff that he's got planned and that he's doing is just amazing. mean, he's in Corsica right now riding like a thousand miles around the island you know, on bike. He's a he's a bicyclist, you know, at 70s. 

Just he does 100-mile rides. And yeah, it's just it's just crazy. And it's he's an inspiration. He is an inspiration. My buddy Conrad is an inspiration to me. And he he's been on this boat quite a bit. I've worn his ass out. But he doesn’t like the heat. It could be it can be tough. But yeah, you're right. You know, and as I get older, I feel a sense of urgency to do more. It's not like I want to slow down; it's like I want to speed up.

Rick Barron (59:05.925)

Will you become more, and speaking for myself, more sensitized to when you hear someone that you knew passed away, whether they were younger or older, and it's like, wow, I just talked with them two weeks ago and now they're gone. It just, it makes you wake up to the fact that life is here to be cherished and just dive in, you know.

David S (59:31.938)

Yeah. And that doesn't mean simple things don't, you know, bring great joy too.

you know, and sometimes just being present in a simple moment, you know, whether it's with yourself or with nature or with a puppy in your lap or whatever, you know, it's just appreciating life's moments. They don't have to be peak experiences all the time. And that's that's something I struggle with because I'm kind of a I'm kind of a I wouldn't say adrenaline junkie, but I'm kind of a peak experience junkie. I'm always like trying to find something new and inspiring. But sometimes it's just right there.

Rick Barron (01:00:09.521)

Yeah. So, so David, I guess in closing, I want to ask you, I don't know, pearls of wisdom that you might want to pass on to somebody who may want to look into what you're doing today, you know, in sailing. What maybe, you know, two thoughts come to mind that if you're going to do this, keep this in mind.

David S (01:00:34.508)

Yeah, I think if you feel like you have an interest in doing something like this, the best way to find out is just to get started. You know, it's that old journey of a thousand miles starts with the first step and go take a sailing course or go volunteer on a, you know, afternoon sailboat trip. 

There's a lot of yacht harbors that are, you know, yachting clubs that are always looking for crew and, you know, just go out and try it. And if you find that you enjoy it and it's inspiring, don't be afraid to invest some time and some money and, you know, follow the path, you know, figure out what, you know, are the steps to getting to where you're skilled enough to actually charter your own boat and then try chartering a boat and see how you like it.

 Then you know take a look and see you know what you can afford and don't feel like you have to have the biggest baddest boat you know just get started with something and try that for a while and don’t be afraid to start the process because it'll become clear pretty quickly whether you love it or not you know so that.

You know look up Captain DaveSailing.com if you want to come down and see, you know, sloths and monkeys and turtles and go sailing on beautiful ocean, the white sandy beaches.

Rick Barron (01:02:10.801)

So, David, I really want to thank you for taking the time out of your busy day to sit down and talk about your life in the world of sailing and the adventures you're having, you know. again, it's been a long time, but it's damn great to see you again. And it's good to see you, that you're in good health and that you're enjoying your life and you're having a blast. I really applaud you for that.

David S (01:02:41.186)

Thank you, Rick. It's great to see you and to see you running this podcast series. I was really impressed when I looked at all the various guests and topics you've covered and all that. And it's a real honor for you to ask me to share my experience with you and your viewers.

Rick Barron (01:03:00.821)

Thank you for that. And to the audience, I appreciate you joining in with us and tune in next week and we'll have another guest. We'll have a great conversation. And to that, we'll talk to you soon.