From Yacht Captain to Real Estate Mogul: An Inspiring Journey

Dylan Silver (00:00.706)
Hey folks, welcome back to the show. I’m your host, Dylan Silver. And today on the show I have Scott Kidd. Scott is a yacht captain for the past 20 years, multifamily investor for the past five, and host of the Yacht Captain Investor podcast. Scott, welcome to the show.

Scott Kidd (00:18.52)
Hey, thanks Dylan for having me. I really appreciate you taking the time to speak to me.

Dylan Silver (00:24.106)
Absolutely. No, thank you for coming on the show. I’ve spoken to so many various avatars of real estate investor, people fix and flip, people who have a W-2 job in medical and are also using their income to create a rental portfolio for themselves. I’ve spoken to people who build hospitals. I’ve spoken to hard money lenders. I’ve spoken to commercial real estate brokers. I’ve spoken to mortgage advisors. I could just keep naming.

but I have not spoken to a yacht captain yet. So I’m very excited because I also love to travel. So tell us, how did you get into the real estate space?

Scott Kidd (01:01.242)
Well, I got into the real estate space originally because as a yacht captain or just working on yachts in general, it’s a fickle business that, you know, here today, gone today, it, you know, I work on a wealthy person’s toy. And if they have, you know, a downturn on their business or downturn on the economy, they get divorced, somebody passes away, or they just decide not to have the boat. That could go away at any time. So it was had a…

some kind of side hustle or something to, know, cause it’s not a matter of if you lose the job, it’s when, cause and that could happen today. I mean, it could happen right now. mean, but it’s just one of those things I always had to have a backup plan. I was started with single family homes as a family got bigger, bought another home, rented the other one. And then fast forward, I was with a friend of mine.

We’re on the beach and we’re having some drinks and he told me that he bought and sold a 46 unit apartment building in Houston, Texas. And he had made in the sevens figures with himself and his brother. And I said, well, you can do that. And he said, yeah, you can do that. I did it. Anybody can do it. And I said, OK. And so I kind of.

It was very intrigued with that because I said, well, I need some kind of cash flow. I’d done, you know, the single family, said, you know, I was going to get one every year, like a lot of people, but I didn’t see how that was going to get me there quick enough. Not that it needed to happen quickly, but I saw that I could have economies of scale and multifamily and stuff. So that started my journey. I started slowly. It took a little while.

Dylan Silver (02:41.091)
Right.

Dylan Silver (02:50.69)
I’ve heard this said before in real estate, the fast money is slow money. The fast money is slow money. But what’s interesting is a lot of people talk about breaking into real estate and how to do it wholesale, fix and flip, short term rental, corporate housing, multifamily, Airbnb arbitrage, so many different ways, right? I’m a real estate agent. started off in wholesale, but I’m also someone who’s highly analytical.

Scott Kidd (02:55.875)
Yes.

Scott Kidd (03:13.561)
Yeah.

Dylan Silver (03:20.854)
And I am not opposed to risk, but I wanna be prepared. So if I’m gonna lose my shirt, I wanna be prepared for how that might look. And so when I was initially going into the real estate space, I was selling cars, I wanted to find a way out, and I did so much research for like years, honestly. It was like probably two full years of me researching. And then I discovered, hey, there’s these companies that…

Scott Kidd (03:40.803)
Mm-hmm.

Dylan Silver (03:47.79)
could potentially be hiring in the real estate space, ended up applying to a bunch of them, got blessed and fortunate to get hired by one of these companies, and then I started learning about wholesale, and that was kind of my journey. So for you, that friend was that bridge to here’s the real estate space. If it wasn’t for that friend, do you think you would have eventually made the jump, or was he really the impetus for it?

Scott Kidd (04:15.008)
I don’t know if I would have. mean, I probably would have found out about it eventually, but had you not told me that, you know, that was a possibility, I probably wouldn’t. Cause I didn’t really know anybody that owned apartments other than, I mean, the first person that gave me their, gave me a captain’s job. He was a real estate developer and had been building homes and developments and apartments since the fifties. But you know, that was…

you know, 2000s and, you know, all these deals you really have to be invited in. And he probably would have taught me a lot more about it had I been more, you know, more involved. But, you know, at that point I was busy working on, you know, being the best captain I could be and, you know, building my career, which I, I, I thought that’s what normally you would, you would do, but I didn’t.

I didn’t know that these things were possible. it just goes to show you that if you don’t see it, you may not know it exists.

Dylan Silver (05:19.502)
To your point, Scott, yeah, I had nobody in my vicinity that I, no family, no cousins, no uncles, nobody who was in the real estate space. And so they were all very much so like super stable type jobs, even sales. I was a sales guy. That was like almost outlandish that I would be doing that, selling cars. And so for me then to go into real estate, what it ended up being was,

Scott Kidd (05:28.376)
Yeah.

Dylan Silver (05:46.978)
They had a RIA conference, a Texas RIA conference, and I was very interested in the RIA events, and they had two people who I really liked who spoke at one of the RIA events. It was one of two people. And I was just really impressed by them individually, and so I think it was something like $1,700 or something along those lines, and that was a lot of money for me at the time.

Scott Kidd (06:10.549)
Mm-hmm.

Dylan Silver (06:11.232)
And so I put that money and I went with a buddy and my buddy said, yeah, I’m not I’m not going to that. But I ended up going. And then that was the impetus for like my whole my whole career after that. The last two years ended up being because of that conference. And it was a great conference. It really was. It changed my life. It’s funny enough. Vanilla Ice ended up being there as one of the speakers talking about his, I guess.

Scott Kidd (06:24.974)
Wow.

Scott Kidd (06:35.257)
Nice.

Dylan Silver (06:39.212)
fix and flip or contracting journey. And just me having no deals, knowing nothing. I couldn’t even understand any element of a real estate contract. I did not know what I was talking about. I was just there kind of like deer in the headlights and talking to people and they were.

gracious enough and kind enough to tell me their story and their insight, that really made me believe I could do it. And so for you having that friend, it was like, well, he’s doing it. I’m going to jump in too. So what was the next steps for you? Like, of course, you’re a yacht captain. How do you go and slowly start getting into the real estate space?

Scott Kidd (07:07.706)
Yeah.

Scott Kidd (07:15.46)
Well, the next steps, you know, I had some friends that were, they’re always talking about real estate and stuff like that. And I’d always been, you know, just buying and renting the houses and stuff like that. That kind of, it made sense. So I figured there’s a big learning curve with multifamily and syndications and stuff. I, you know, started learning and I wanted to go to a bunch of meetup groups. And unfortunately,

The first 10 or so that I went to were, well they just try to sell you the course, the books, the phone calls, their coaching program and everything else. And I didn’t really meet people that were actually doing it. It was just more new people that were just like me. So I kind of got discouraged and I said, well, let me just go to one more. And then I went to one more and it ended up just being.

It ended up being a person that I ended up partnering with. She and I are still partners now on a 13 unit. And her meetup was just people hanging out, talking about doing real estate, doing multifamily, doing all kinds of different real estate. And she’s still a partner. She still has the meetup group. And I eventually started my own meetup group because I figured other people on Yonk wanted to learn about it as well.

kind of been a big part of my journey as well is is sharing the experience with other people and want them to know not necessarily for them to invest with me or anything but let them know that there’s options and opportunities out there let them know that hey you can take a shot at something you know don’t think that you’re stuck

Dylan Silver (09:04.46)
And so you have your own meetup. Where is it based out of?

Scott Kidd (09:08.654)
Well, we have three meetups, Fort Lauderdale, Florida, Stewart, Florida, and West Palm Beach. And because we’re collaborated with a group called Like-Minded and they’re going nationwide and they do events and stuff as well. And so I can say that, you know, collaborating with people and partnering with people has really accelerated a lot of things.

Dylan Silver (09:34.222)
You had me at Fort Lauderdale, Scott. I think that is my favorite area in the country. I went to Fort Lauderdale. fiance actually lives in Santo Domingo in the Dominican Republic. And so coming back from visiting her, I’m in Fort Lauderdale on a layover and I’m like, this has got to be the nicest part of the whole country. Someone said Boca is a little nicer. I haven’t been to Boca.

Scott Kidd (09:36.292)
Hehehehehe

Scott Kidd (09:48.035)
wow.

Dylan Silver (10:01.836)
So you being based out of there and having that meetup over there really just makes me super jealous. So you have the meetup and people are coming on in and you’re scaling in the multifamily space. What particularly do you like or find attractive about multifamily versus single?

Scott Kidd (10:21.402)
The economy is of scale and I found that it’s very similar to what we do on the yachts is where we build a team and we build teams. You know, we’re a part of a team because without a great team, the boat doesn’t go anywhere. The boat will probably sink. Without a great team, the multifamily apartment or commercial real estate, that’ll sink. If you don’t have a good team, keep an eye on it, running it, managing it.

acquiring it, selling it, it just will fall apart. If you have a bad team, will be a nightmare.

Dylan Silver (10:59.35)
I completely agree. mean, especially with multifamily, there’s economies of scale. There’s also greater risk, right? So when people, when real estate agents talk about, I would love to do commercial, well, there’s also greater risk in commercial. as to your point, you get the upside, but you also get the downside. So it’s why it’s so important to have those partners.

Scott Kidd (11:06.264)
Mm-hmm.

Scott Kidd (11:14.114)
Yes.

Scott Kidd (11:19.352)
Yes.

Yes, it’s much more expensive when deals don’t go through, when they fall apart, as they do. I mean, we had some deals not go through last year. It was quite expensive, still paying for those, but that’s a part of it. More often than not, a lot of the other deals have been a lot better, more lucrative. And it’s a long game anywhere, I’m not going anywhere, so you have to take your lumps sometimes.

Dylan Silver (11:51.608)
So.

Scott Kidd (11:51.82)
It happens in single families as well.

Dylan Silver (11:54.222)
For sure it does. I’m in that space. For the niche that you’re in, yacht space and then also real estate, are there a lot of people coming up to you saying, do I get into the real estate space? Or are they saying, hey, I heard that you’re doing this. How do I partake in these deals?

Scott Kidd (11:56.41)
Ahem.

Scott Kidd (12:15.798)
Sometimes, know, it’s more they’re curious a lot of times like why are you some people are saying like why are you doing two things why you know once you do one or the other but I look I love both of them so I’m gonna continue to do both of them because I I don’t think you have to just do one thing if you know maybe I don’t get as much traction in both at the same time but I

love both of them, I’m passionate about both. So why not? shouldn’t I be happy doing whatever I want to do? If it takes me longer or it doesn’t, or it takes me longer or somebody’s upset about it, that’s not my cross to bear.

Dylan Silver (12:50.08)
Amen.

Dylan Silver (13:00.29)
I’m a big believer, Scott, in this idea of fanatical networking, or some people say networking junkie, guerrilla networking. And I feel like I owe every ounce of my success, not to, not even to a particularly great work ethic. I think I’m a hard worker, but I know that there’s some people who just grind to the bone and I’m not one of those people. But what I will do is I will go to a, like you mentioned, a bunch of meetups. I have the same story, meetup after meetup after meetup after meetup. And I tell people,

Scott Kidd (13:07.331)
Yeah.

Scott Kidd (13:17.209)
Yeah.

Scott Kidd (13:24.324)
Yeah. Yeah, Yeah, this guy’s everywhere.

Dylan Silver (13:30.058)
everywhere. I tell people that if you’re going to one meetup a month, or even one meetup every other week, it’s not enough. Even at the stage that I’m at now, I try to get to two, two types of networking events. It’s not necessarily directly related to real estate investing. But I’ve been to ones for like, real estate service providers, I’ve been to ones for real estate agents, right. And so I’m just always trying to mingle with

Scott Kidd (13:54.199)
Mm-hmm.

Mm-hmm.

Dylan Silver (13:59.884)
new crowds and different people in the real estate space. But your background being a yacht captain, I almost feel like this is the all time great hack for meeting real estate investors. So do you feel that way? Do you share that sentiment being a yacht captain, of course mingling with people who have great wealth? Are you seeing like, well, this is a really great opportunity to meet investors or is it kind of difficult because it’s two separate worlds?

Scott Kidd (14:30.17)
Well, it can be two separate worlds. More traction I’ve gotten through people that work on yachts because people that have, that own these yachts, you people think, why don’t you just, you obviously know all these people, so they’re obviously going to invest with you. It doesn’t really work that way because, you know, people that are, just because you know a bunch of people doesn’t mean they’re going to invest with you, you know? And they know me as the yacht captain. Like they give me,

Dylan Silver (14:53.39)
Mm-hmm.

Scott Kidd (14:57.348)
you know, sign off on three, $4 million for me to do a refit or, you know, to redo the yacht. But $3 million to do apartments. Like, wow, we don’t know you for that. But, know, so that takes a little more time. It’s like with a family office or a private equity group, those relationships with those larger checks, there’s a huge vetting process. The same way like the yacht owner would have like, they probably have a real estate department. you know, they,

They come to him and say, or her, have, you know, we have this deal, but that’s got to go through Johnny and Steve and, know, and his thing. And then if, if you do get the introduction, Johnny’s not going to really like it so much because you’re kind of stepping into his world. They’re like, Oh, this is the boat captain. What does he know? This is my world. You’re stepping on his toes. So then it’s the ego thing. um, and I, you know, Jen and generally, you don’t solicit the guests because it’s

Dylan Silver (15:36.323)
Yeah.

Scott Kidd (15:56.73)
You’re there for their you’re hired to do their job But if they find out and they ask you about it and you talk to them about it, that’s that’s different, you know, I’ve had Long time charter guests. I’ve had them ask me about stuff before and you know some sometimes stuff comes over and other times, you know, it really doesn’t but it does kind of raise your profile because we get to have these conversations with these high net worth in individuals that will

Most of the time, gladly tell you their entire story of how they made it, the mistakes they made, stuff like that. And they’re curious about what other people are doing. so we get to hear firsthand what’s going on. And we get to hear these big solutions to these big problems sometimes, which I always keep my ear open because I never turned down an opportunity to learn.

Dylan Silver (16:29.624)
Yeah.

Dylan Silver (16:53.324)
the same with you, Scott. So on this podcast, I’ve had so many different real estate investors and entrepreneurs, and just being able to talk with some of them and like, I can’t believe that we’re having a conversation, you know, and here I am, again, talking with a yacht captain and real estate investor. How else am I going to have this conversation, right? The other day, I was talking with an endodontist. I did not know what that was. It’s a it’s a dental surgeon. Okay.

Scott Kidd (17:11.79)
Yeah.

Scott Kidd (17:19.278)
Yeah

Dylan Silver (17:21.848)
who was Columbia, Harvard education, right? And what he does is he helps dentists basically open up their own buildings and their practices. And I don’t know if he does any mentors, if it didn’t sound like he did, but he shifted from that. And what was so crazy about his story was he had an injury which prevented him from doing medical work, from doing dentistry.

Scott Kidd (17:24.825)
Wow.

Scott Kidd (17:35.254)
nice.

Scott Kidd (17:50.106)
Wow.

Dylan Silver (17:51.046)
And I know, so I was like, dude, what? So hearing these stories and like the overcoming and it really made me realize that you can see, and I’m sure you feel this way too, Scott, you can see a lot of your own story and other people’s stories, even if they’re super far ahead of you. You’re like, wow, that’s, I can do that. And so then you start typing out, well, how do I get there?

Scott Kidd (17:54.17)
That’s a pretty cool story.

Scott Kidd (18:09.882)
Mm-hmm.

Scott Kidd (18:14.376)
yeah, that’s definitely true. I mean, there’s so many ways to do it, so many different people doing it. It’s just pretty amazing that, you know, a lot of people get very egocentric about, well, I do this, I do that, you know. But, you know, to me, it doesn’t really matter. It’s just that you are doing it or you’re going after it and it makes you happy. So keep doing it. If you’re just doing it for the money, you’re probably not going to be happy.

Dylan Silver (18:43.948)
Yeah, no, it’s very tough to have a state of well-being. There’s plenty of people, plenty of people who are making a lot of money and are not particularly happy, sometimes even healthy, and they kind of go hand in hand. Like, you could work a 10-hour day, know, nine to whatever, seven or five, or whatever it is, my math is off here, but you could work a 10-hour day and you could still be miserable doing what you thought you wanted to do, but…

Scott Kidd (18:50.127)
Yeah.

Scott Kidd (18:57.027)
Mm-hmm.

Dylan Silver (19:13.194)
If it turns out that it’s not what you thought it was, and I have a great example of this, lawyer, a lawyer, Arizona, very young guy, lawyer in Arizona, was sitting down across from someone else at a law firm that he was working at, fresh out of law school, and the guy was telling him, in 20 years, you can be where I’m at. And he was looking at this guy, and he was like, I do not want that, and I’m unhappy in this job. And so he had, yeah.

Scott Kidd (19:34.362)
I don’t want to be there now.

Dylan Silver (19:39.116)
He had spent all his education, law school, internships, getting this job, Finally out of law school, passed the bar exam, sitting in the room. And so he decided at some point I have to find my way out. And he went, if I’m not mistaken, into either duplexes or multi-family.

and he had a big Airbnb strategy and that was his way out. And so to your point Scott, it’s not just about like making a bunch of money because you can make a bunch of money and be like sick to your stomach. And so you gotta really like to do what you’re doing and if you can find a way to make it a win-win, that’s when you can really develop momentum.

Scott Kidd (20:11.418)
Mm-hmm.

Mm-hmm.

Scott Kidd (20:21.018)
Mm-hmm.

most definitely. it’s not for the faint of heart but I like putting the puzzle together and like I said building the teams and that’s what makes it fun for me and the people part is really the key in any business you know because if you don’t have the right people in the right seats chances are probably won’t go well.

Dylan Silver (20:48.78)
Yeah, no, you have to have the right people. bad partnership can be, cost you a lot. Bad partnership can be almost as bad as a bad marriage. you don’t want to, they can cause, yeah, I mean, I’ve heard, and I don’t even have more than two years in this business, but I’ve already heard so many stories.

Scott Kidd (20:56.152)
Yeah, it can cost you everything if it’s…

Scott Kidd (21:07.674)
Well, yeah, bad partnerships, you know, it’s just pretty stressful. You you don’t necessarily make the other person a bad person. It’s just maybe you’re not in alignment with everything you’re doing. you know, like this in people’s lives change, you know, where people are when you sign up for the partnership may change in a year or two. And you may have to make an adjustment. And it can be, you know.

Dylan Silver (21:27.181)
Yeah.

Scott Kidd (21:36.29)
one of those things where maybe you have to walk away or maybe you have to sell out or, you know, but, you know, think very carefully when you’re getting into a partnership with somebody, because it is, like you said, it is like a marriage. It really is because you’re signing on that contract. It’s five, you know, especially syndication, five, seven, 10 years. You’re involved with these, all these people. There’s quite a few people involved, you know.

Dylan Silver (22:01.688)
Yeah, you’re not it’s not like you just going to the bank and taking your money out or or going on to you know, your your broker account with it with a stock broker and selling your stock you’re in it until the deal sells so it’s gonna be a long a long ride We are coming up on time here Scott. Where can folks go to get a hold of you?

Scott Kidd (22:05.421)
You

Scott Kidd (22:11.555)
Ahem.

Scott Kidd (22:21.21)
You can go and find me at my website investwithscottkidd.com all my social media links all my email contact information is there my podcast everything is there

Dylan Silver (22:35.704)
Scott, thank you so much for coming on the show. Thank you for giving us some value, for telling us about the yacht industry and the yacht space. I don’t even have the vernacular, the jargon to talk about that industry. if I ever come across another yacht captain in the real estate investing space, I’ll have some more stories to tell. Scott, thank you so much for coming on the show today.

Scott Kidd (22:45.946)
You

Scott Kidd (22:55.578)
I have no problem. I probably know there’s a few of us out there. Thank you.