How to Build a Land Investing Business That Lasts | Jessey Kwong & Kevin Rockwood

Jessey Kwong (00:00)

The investors that stick around are the ones who really think about this like a business. And I do wanna stress this is not an easy business at all. just like any other business. I think there was this illusion that it was for a while and certainly it was different, seven years ago when I first got started that means you have to come ready to play this game. I like to say this is a pay to play game. I shouldn’t say game, but like any business, there are costs up front.

coming into this, there’s not a lot of upfront cost to get a business up and running. but if you don’t have the capital to be able to send out marketing, if you don’t have the capital to be able to take down properties or access to capital, this is going to be a very challenging business.

Scott Bursey (01:17)

Welcome back to the Real Estate Pros Podcast, powered by Investor Fuel. I’m your host, Scott Bursey. Glad you’re with us. And today we’re delighted to be joined by Jessey Kwong and Kevin Rockwood. Jessey and Kevin are the founders of Pebble REI, a platform built to help land investors simplify their operations and scale their businesses. Gentlemen, welcome to the show.

Jessey Kwong (01:40)

Thanks for having us on, Scott.

Scott Bursey (01:41)

And to help our listeners get up to speed, please give us the ninety second highlight reel of how your career ignited and where you’re pouring your fuel now.

Kevin Rockwood (01:50)

Yeah. I’ll go ahead. So Jessey and I started this company in 2020. We both come from a land investing background. And I had built this tool. I’m also a software engineer, built this tool to run my own business, and that grew into what is now Pebble. And we have customers all over the world who use us to scale their businesses, so it’s pretty fun.

Jessey Kwong (02:10)

Yeah, I think that really summarizes everything. Kevin was working on the actual product for his own business and that’s when I caught wind of it. I forgot what online group we were in, but we spotted each other and I spotted his work and I was also building an audience and helping with investors with their digital presence and so we connected, decided to

Give this a try and here we are, my gosh, six years later.

Kevin Rockwood (02:33)

Yeah.

Scott Bursey (02:34)

That’s awesome. Thanks for setting the table, gentlemen. And you know what really caught my attention about you two was the way you’ve been able to turn services into software. That path gives you a view of this industry from the builder’s side that most people never get. I guess taking that a step further, and we can start with you first, Jessey. What did building websites for investors teach you that evolved into Pebble?

Jessey Kwong (02:57)

Yeah. I think that there was a bit of catch up to do in the digital world, a lot weren’t used to running their own websites, running their own business online and never mind thinking about processes and systems that really came later. seeing that there was certainly an opportunity to help others

really get into that mindset how to start up a business, how to run a land investing business. This is no different from any other business out there, whether you’re talking about Starbucks to your own real estate investing business, it comes down to processes and systems and experimentation. that’s where things kind of kicked off from.

Scott Bursey (03:32)

And Kevin, what carried over from the agency days into Pebble?

Kevin Rockwood (03:36)

Yeah, as a software engineer, I built Pebble as a tool to streamline my own business. And I just built what I wanted and what I wanted wasn’t there in the market and so I just built it and kept iterating on that and eventually that caught wind and a bunch of people found value out of it too.

Scott Bursey (03:56)

Appreciate you sharing that. Thanks for breaking that down, gentlemen. And Jesse, talk to us about where do you feel land investors are breaking down the operations and what are some of the core friction points that you’re experiencing?

Jessey Kwong (04:11)

Wow. I think a lot of people come into the business thinking that it’s going to be a lot easier than it is, and they don’t really think ahead and fire from the hip type of thing. And

The investors that stick around are the ones who really think about this like a business. And I do wanna stress this is not an easy business at all. just like any other business. I think there was this illusion that it was for a while and certainly it was different, seven years ago when I first got started that means

you have to come ready to play this game. I like to say this is a pay to play game. I shouldn’t say game, but like any business, there are costs up front.

coming into this, there’s not a lot of upfront cost to get a business up and running. but if you don’t have the capital to be able to send out marketing, if you don’t have the capital to be able to take down properties or access to capital, this is going to be a very challenging business. the real operators that stick around.

They understand this and maybe they’ve been through quite a bit where they can make a little bit more calculative steps and understand, why they might potentially lose and what will they potentially gain. that’s some of the friction I see.

Scott Bursey (06:03)

That is an excellent breakdown. And Kevin, if you could expand on that just a little bit, what makes a land business sustainable over the long haul?

Kevin Rockwood (06:12)

Yeah, I think it’s really just that consistency. And this is what everyone will say. it just requires someone who’s going to keep at it, keep going. there’s going to be times where things don’t work out or where something becomes difficult. And those people that are just able to run the marathon and able to just, keep at it, keep going.

and adapt, sometimes the market does change and you do need to change strategy and being cognizant of that and capable of making those changes is really important.

Scott Bursey (06:42)

Jesse, where does technology help most and where does it get in the way?

Jessey Kwong (06:47)

Yeah, I can answer that latter part. I think Kevin and I have been talking about this. it can make things a lot more convenient and allows you to do things at scale and that can also get in your way because you can easily get diluted with your focus.

that’s one thing that Kevin and I think about, especially with the rise of a lot of the AI stuff, is we can do a lot, but what are we supposed to be doing? And this almost forces somebody to be ultra clear with what they wanna do, where the direction of the business is, whether it’s, your strategy or your target audience or whatever,

You really need to be very clear because technology makes it very easy for you to do things, but that also can take away from your messaging, take away from your strategy. that’s where I see technology kind of get in the way. And technology allows you to do a lot of things and just as an example, we send out very highly personalized letters to owners and

we’re able to see what performs well and get hyper personalized things I’ve got an example here, sending, images of their property that they want to acquire. and we can do this at scale and automate a lot of this stuff, but if don’t have the right messaging, it’s not going to cut through all the crap. And that’s the other thing, there’s just a lot more noise now that you have to combat it.

that’s what I see with technology opening and also forcing you to think about

Scott Bursey (08:50)

Thank you for that, Jesse. And Kevin, what have investors and operators taught you about what growth really takes?

Kevin Rockwood (08:57)

Yeah, the cool part is that we get to work with a lot of very active and successful investors. And those ones who are just the dogged they’re just gonna keep going and keep iterating and keep going up that growth ladder. and not that they’re smarter or have some secret sauce.

They’re excited to wake up and get on the phone and start making deals happen. and the ones that we, have been with us for years and years are those ones that are just able to keep it going. they’re phenomenally successful. even when the markets go down, they find ways to keep being successful.

Scott Bursey (09:33)

Jesse, where does Pebble go from here?

Jessey Kwong (09:36)

we’re focused not only helping with investors, but we see there’s a lot of other parallel businesses and industries that are looking to acquire land. whether that’s home builders to property developers, to renewable energy developers, brokers,

data centers, land is needed all the time. And guess what? we come to realize that it’s quite similar. and so there’s a lot of opportunity for us to start now leveraging some of the knowledge that we have working with land investors and start to work with other industries that are also looking to do this, to make use of land or real estate as that’s the end of the day for whatever they’re focused on.

That’s where we see things going. we also, are excited with a lot of the things that are going on in the AI world. how you run Pebble is really exciting. Connecting it to Claude or Grocbot or whatever it is and having, virtual agents manage and run your system has been unbelievably really, really cool.

there’s a lot in both of those.

Scott Bursey (10:35)

Kevin, maybe you can expand a bit on what’s the long term vision of Pebble REI?

Kevin Rockwood (10:40)

Yeah, we’re just gonna keep helping our customers, what we live for is helping our customers do more, get more done, not let deals fall through the cracks. all of these things are where we get our fuel to keep going. so we’re gonna keep doing that. We’re gonna keep helping people.

That’s always the fun thing when somebody signs up and they’re like, my gosh, I can’t believe I can do this with your product. we’re gonna keep building.

Scott Bursey (11:05)

Man, that’s a great way to look at it and to continue to build. Jesse, let me ask you, what does your professional network look like right now?

Jessey Kwong (11:13)

What does my professional network look like right now? I’m not sure how to answer that. we hang out in the land world with land investors. we attend and we talk at conferences, and so a few of our friends in the space run conferences. There’s the podcast as well. I’ve got a network there, and I’ve recently started learning LinkedIn.

a little bit late to the game with that, but certainly a different area and meeting a lot of really cool people and working on content out in that area. And we’re also, gonna be in the room with a lot of people from different industries, again that are focused on land. I guess we’ve kinda got our legs in, a couple of different areas.

Kevin Rockwood (11:50)

Yeah, we’re also part of some business groups specifically around, building SaaS companies. So we meet with a lot of other SaaS founders and a few different masterminds around that. those are always fun. I learn a lot from those.

Scott Bursey (12:01)

Well, absolutely. Thank you for taking us into your circle, gentlemen. And Kevin, let’s dive deep. What’s the one system that keeps a land business steady month after month?

Kevin Rockwood (12:13)

Yeah, I think having what we call the single source of truth is really important. with land, especially those who have been around for a long time, your business is going to change, you’re going to evolve, but at the end of the day, you’re reaching out to property owners, you’re handling leads, and if you

are switching systems or you have some of your leads in a Google Doc somewhere and you have some of your leads in HubSpot and some of your leads in, Trello board, that system you’re really hampering your ability to get the benefit of the data that you have. Pebble’s a great way to do that, but if you’re just gonna choose

any sort of system, just making sure that all of your data, all of your history is in one place. Then five, six years from now, you can look back at that and start gleaning information about it. where are my most profitable leads coming from? And you can start working back. and without having that data in one place, it makes it really tough. So that’s a big one we see.

Scott Bursey (13:09)

I love that. Thanks for taking us down that road. And gentlemen, you have really provided a lot of very good insight here today. But Jesse, is there any additional words of wisdom or two that you’d like to leave with our listeners?

Jessey Kwong (13:23)

Words of wisdom. I think one that comes to mind is be open to experimenting. You can’t come into any business thinking it’s a business out of the box. And I’m sure your audience, a lot of them are real estate investors, and no matter what you learn out there, this is no different. you have to have the skin to be able to experiment and try things, and you’re gonna find a lot of wrong things along the way.

I don’t like making mistakes but you will have to just accept that things won’t pan out the way you would like things to pan out. And so I urge, even in investing, as straightforward as the model sounds, it’s never as straightforward as it sounds. And you do need to find your path. This is no different from any other business. that’s what I have.

Scott Bursey (14:06)

Kevin, do you have anything to add to that?

Kevin Rockwood (14:08)

Yeah, I think that sums it up pretty well. you need to be able to experiment, you need to be able to keep at it, and eventually something will work. it’s really just about running that marathon and getting to the finish line.

Scott Bursey (14:19)

The long haul. Thank you for that. Jesse, for those of our listeners that want to keep this conversation moving, stay in your lane or collaborate with you perhaps on future deals, what’s the best way for them to plug into your pipeline and reach you directly?

Jessey Kwong (14:34)

Yeah, you can literally just head over to Pebble R E I and there’s literally a book a demo button there. it’s probably the easiest way to hop on a one-on-one call with me. don’t flood me just to talk about your day. let’s talk about your interest in land or your land business or maybe whatever sort of real estate investing related. happy to hop on a call with you. And if you are somebody in the space that

wants to talk about your business and anything land related, I’ve also got a podcast which is the Land Investing Business Secrets podcast. So happy to have you on. you can reach me on our website. that’s probably the easiest.

Scott Bursey (15:06)

Jessey and Kevin, thank you so much for joining us today on the Real Estate Pros podcast.

Jessey Kwong (15:10)

Yeah.

Scott Bursey (15:11)

This has been a blast. And to our listeners, we appreciate you. If you receive value from today’s episode, please subscribe. We’ll be feeling your tanks with a lineup of elite guest, just like Jessey and Kevin, who are accelerating and setting the pace for the rest of the industry. Until next time, keep your standards high and your vision clear. We’ll see you on the next episode, everyone.