Bubba Booking

Watch: Bubba Booking

Joe Benjamin (00:00):

Started cool. We're recording. So, hey, this is Joe with Capture. We have a founder interview series today with Kaitlyn and Carl. Kaitlyn and Carl, why don't you give the audience a little background on who you are and what your company does?

Kaitlyn (00:17):

So I'm Kaitlyn. I guess I'm the co-founder of Bubba booking with CJ. Our app and our website is all about if you're on vacation and you're looking for something to do, you come over to us and we'll show you all the tours and activities happening near you with availability for the week you're on vacation.

Joe (00:35):

Very nice. And what, go ahead. Sorry.

CJ (00:40):

No, I'm CJ. And we're husband and wife, you know, co-founding team. Like Kaitlyn said, we have a last minute tours and activities marketplace.

Joe (00:51):

Very nice. And where's your coverage area?

Kaitlyn (00:55):

So right now we're mainly based in Florida, but we do have tours all across the United States.

Joe (01:01):

Awesome, and so what made you start this business?

Kaitlyn (01:05):

So we started this because we're honestly not good at like relaxing. So on vacation, when we would go on vacation, we're always looking for something to do, but it would take me like a week or two weeks before a trip to find all those activities. And on our honeymoon, one of the trips that we were really looking forward to got canceled, it was swimming with dolphins in Hawaii. They're wild dolphins, so no one can hate me for that one. So it got canceled and it took me probably like two hours that morning to find something else to do. And when we went on the boat that afternoon, it only had three other people on it and it could have fit 20. And we were like, all right, there has to be something broken here because it took me hours to find this boat and this guy's losing money because he doesn't have enough people that he's taking out. So that's where the idea came from.

Joe (01:56):

Very interesting. And how long have you been at it?

Kaitlyn (01:59):

We've been at it for two and a half years.

Joe (02:03):

Two and a half years. So you've probably had a lot of ups and downs. Why don't you share like one of the moments where it was a really scary opportunity and you guys were like, maybe unsure about moving forward?

Kaitlyn (02:14):

So I feel like, yeah, over the last two and a half years, there have been a ton of ups and downs. And I think it's not even so much as like, there's been like a low point when we've been wanting to give up. There's been a lot of points where we've had to like make decisions that we probably wouldn't have, if we didn't have the business. So when we first got married, we took all of our wedding money and we dumped it into the company. 

Joe (02:33):

Oh, wow.

Kaitlyn (02:35):

And we just started it from that. And then we were living in this beautiful apartment in Boston and we then made the decision, okay, let's move into like a less nice apartment because you want to be able to spend money on the company. And then we even took it a step further and said, when COVID happened, let's just like, cancel our lease completely. And we moved into one of our parents' houses.

Joe (02:55):

Oh, that's a sacrifice for a lot of people.

Kaitlyn (02:57):

So, and I know during COVID, a lot of people were like, should we buy a house? And we had that conversation. And we always have this conversation of, you know, should we do something personally for ourselves or should we do it for the company? And we've always chosen the company. So I feel like that's probably the hardest thing about it, but we have nothing else to do. Like, we love doing this, we want to make it work.

Joe (03:21):

That's great. So what keeps you going? Like we know that starting a company from scratch has those ups and downs. It can be a grind. You have things like COVID that come in and, you know, probably affected your industry a lot. What keeps you going? Like what allows you to just like get up every day and follow that grind and push forward?

CJ (03:38):

I think it's probably like the little validations along the way. Like when we got our first customer after we went live after COVID or really towards the tail end, that was a big milestone. But I mean, it's just like the little things of hearing good feedback from like tour operators that you work with and you hear that, you know, a lot of them are husband and wife, businesses, small businesses that are grinding to make it. And, I don't know, I think it's like little things that you celebrate that keep you motivated. I- Neither of us really want to work for somebody at the end of the day. So like being your own boss and kind of choosing your own destiny, that's- that's definitely empowering.

Joe (04:19):

I had a SAS business and I remember the first time we signed a customer, we didn't even have a bank account set up yet. And it was like an amazing feeling. We were like, wow, we created this product. Someone was like, I want to buy this product from you that you came up with, like out of your head. Tell me how it felt like when you guys got that first sale and someone was like, I want to do business with you.

Kaitlyn (04:39):

Yeah. Oh, sorry.

CJ (04:42):

That’s our other co-founder, Walter, the dog.

Kaitlyn (04:44):

When we got our first sale, we were like, do you know this person?

CJ (04:48):

Is this your mom? Is this my mom and dad?

Kaitlyn (04:50):

Do we know them? Wally. Sorry, he's very noisy. 

Joe (04:56):

Bring him in. Is that a Bernedoodle? Very cute.

CJ (05:09):

But yeah, when, when the transaction first came through, we were on the phone with our developers and it was a $425 jet ski riding Clearwater purchased by someone named Crystal Shanka. So Crystal, if you're out there, thanks for being, yeah, thanks for being our first customer. And I remember we both like were huddled around the phone, like, well, what, what do we say to confirm it? Like, what, is she going to ask where to park? Cause I don't know where she's supposed to park. And like these little things that you didn't realize before become very big things in the moment.

Joe (05:42):

Yeah, absolutely. And I imagine that like once you got that sale, you like became true believers and you were like, we need to get our next one. So how long did it take from the first sale to the second sale?

CJ (05:52):

Well, that first sale was meaningful too cause that was like the point where I felt like I was a real entrepreneur. Before that I felt like I was building something. And like until we had somebody else validate it by purchasing and using a credit card, like that completed the cycle. And then I think it was probably another month until our next sale. So it's been, it's been sporadic. I mean, we're still scaling the business now and we're just trying to get that run rate more consistent.

Joe (06:17):

So what's been your biggest challenge so far running the business?

Kaitlyn (06:22):

Our biggest challenge is the industry that we work in isn't as software focused. So when we started this, me and CJ both have worked in SAS software, so like APIs are something that, you know, it's an API like you don’t have to explain it. But in this industry it's a brand new thing. So new API calls, working with other people's API, that's been the biggest challenge and updating our software. I think we thought, hey, we'll build it one time and it will be done. And it's amazing like how many times you have to keep changing and iterating and redesigning things. So I feel like that's our biggest challenge, but also what like gets you going in the morning.

Joe (07:05):

Cool. So the space that you're in obviously you probably had some headwinds in the past 12 months, now you probably have some tailwinds with travel just exploding. You know, how do you feel like you're going to be able to take advantage of this opportunity where everyone is vaccinated, people are going out and they have all this pent up demand for travel?

CJ (07:23):

Yeah, I mean the last time there was a big pandemic similar to this was the Spanish flu and what followed that actually was the roaring twenties. So I think that there are big things on the horizons in terms of people moving and crossing borders. Every year since World War II, with the exception of last year, more people crossed an international border than the prior year. So it's grown every single year. I think that's going to return in full force. And I think it's going to be on the backs of an increasingly mobile consumer that's valuing experiences over goods, especially since they haven't had those experiences. And they're pent up to go out and see the world again.

Joe (08:01):

Yeah, I just saw some data about travel domestically. It's like the highest it's been in a long time. Travel’s up over 2019 numbers by like 9% just domestically, which is crazy. And it's just gonna explode. I think you guys are in a great spot. What is something that people that are not in your space would find really interesting about the space that you're in?

Kaitlyn (08:23):

This is CJ’s favorite topic.

CJ (08:25):

So there's no global distribution system that links it all together. And what I mean by that is think about like when you book a flight or you book a hotel, there's like this invisible railroad underneath that shows availability and that makes it so you can't double book things. It also means you can get instant confirmation. Tours and activities is the third biggest travel sector after that, but there's nothing, there's no glue really holding it together. So what we learned was there was an opportunity for us to start patching together our own mini global distribution for instant confirmation. So like, think about it today. If you went to the supermarket and you want to buy a canned soup, it's kinda like if you took that can, you buy it, and then you go home and they call you 24 hours later and say, confirmed, you have that canned soup, it's actually filled. Right now, like you don't really know what you're getting. And so like that time that Kaitlyn was describing in Hawaii of our tour being canceled, we thought that, you know, we had purchased something and we'd gone home with it, but like, it really, there was nothing underlying it.

Joe (09:27):

So that sounds like it's a huge fragmented market that you guys are looking to kind of tie up all the loose ends so people have more reliability in their travel experiences. Is that fair to say?

CJ (09:37):

Yeah. And I mean, it's kind of an angel problem in the sense that you know, it's, it's, it's small businesses that want butts in seats and there are people that want to be in those seats and it's all happening at the last minute. In order to aggregate it in an efficient and accurate manner, you need a third party to step in and kind of quarterback it. And that's where we come in.

Joe (10:00):

Very cool. So you mentioned earlier that you both had jobs before this, can you tell me what it was like when you were like, okay, I'm quitting my job and how it felt like the moment you either put in your resignation or you just were like, I'm done doing this?

Kaitlyn (10:15):

So we actually have not gotten to that point yet. You’re probably surprised. So we have always said like, okay, when we get our first customer, like, I'll be the first one to quit. And that was always the plan. But now we're, you know, a few, you know, we're past that point and because we can work from home now and no one actually knows that we do this on the side. So we've just been able to kind of collect our paychecks and continue working on this.

Joe (10:43):

Very smart. So it's a fully funded, self-funded bootstrap business. 

CJ (10:48):

A hundred percent. And I mean, we both are very dedicated to this and without funding, it's hard to, you know, we pay for an engineer to work on this full-time and that, you know, comes out of my paycheck. And so, to this date, fully self-funded and honestly, a lot of what we learned and continue to learn in our current jobs, I think help us structure our thinking around where the market's going.

Joe (11:18):

Interesting. So how do you balance that, because I know a lot of people have dreams of like the side hustle, but what they probably don't realize is like to actually get a full on business going, it's more than just like a side project. You have to dedicate a lot of time and resources and you know even money. You know, explain how you guys are able to balance that and then what sacrifices have you made? Are you giving up like family engagements or like not going out with your friends socially on the weekends to work on business?

Kaitlyn (11:47):

Yeah. I mean, probably, for probably the last like year and a half, we pretty much just do this. So on the weekends we take our weekends right now, we're driving around to all different hotels to get them to sign up and work with us. And we'd go to like 25 hotels, every single Saturday and Sunday. 

Joe (12:04):

Oh wow. 

Kaitlyn (12:06):

My job is much easier than CJ’s. So I can block off my time in the morning where I only work two or three hours. And then I get to work on Bubba the rest of the day. And then CJ does a lot of night stuff, but we have had to like come up with rules for ourselves like, okay, we will not talk about this past 10 o'clock unless, like it never ends.

CJ (12:29):

I'm more of a night owl. So I'll grind through whatever needs to be done until whatever hour it needs to be completed. And I mean, sacrifice wise, I mean, we, you know, like Kaitlyn said, we downsized our apartment then gave it up entirely. And then a month ago we just packed up the car and drove from Boston to Florida to move down here. So, I mean, it can be a bit of a lonely existence. Like we don't know anybody in St. Pete beach, but at the same time, I think when you say like, “Hey, I'm an entrepreneur, I'm trying to build something,” people gravitate towards that and it's a good conversation starter.

Joe (13:05):

So what's going to be the point where you guys are like, we have to go all in on this, we have to quit our jobs, like we have to dedicate a hundred percent of our available time to this business?

Kaitlyn (13:14):

I think either two things will happen: one, we'll raise funding and we'll be able to do it, but we honestly could raise funding and then hire people to do the things that we're not able to put all of our time into, or two, it just takes off to a point where we just can't handle this anymore. And that point could come pretty quickly when, you know, the marketing side starts to kick in. Like we can already, I can already feel on some days where we have a feature on the app where you can text us and I'll text you back recommendations. 

Joes (13:43):

Oh cool.

Kaitlyn (13:44):

And if five people are texting me, I'm like, okay, like I can not handle this anymore. Like I have to quit my job. So I feel like the time will quickly come and we'll know when that time is here.

Joe (13:54):

So when it's almost like it's a good problem to have, you'll have to solve it with more availability. 

Kaitlyn (13:59):


Joe (14:00):

And as far as goals are, as far as goals are concerned, you don't have to get into like specific KPIs or anything like that, but do you have like a one-year goal, a three-year goal, a five-year goal for the business?

Kaitlyn (14:10):

He's the finance guy. I'm just the fun one.

CJ (14:14):

I think we've said a lot of numbers in terms of how many transactions we want to have a month, how much, you know, gross merchandise volume we want to see flow through it. But I think at the end of the day, it's something you can't really measure and that's more Mindshare. And what I mean by that is like seeing Bubbabooking our company, like see somebody holding it and using it as like the hub for their vacation, for their end destination activities. And that's something you can't really measure. I know people will tell me, you can, in terms of how many downloads and stuff there are, but it's something that I think you just can feel once it's achieving that product market fit and people are living in it for that whole week.

Joe (14:53):

Sure. As far as advice goes, what advice would you give to people who are thinking about starting something on their own while they have a full-time job? Like what is something that you think they need to know?

CJ (15:03):

Take however long you think it's gonna take and multiply it by three or five, because it's always going to take longer.

Kaitlyn (15:12):

And I feel like a lot of our friends ask us this question now cause we're pretty much the only ones who have done something like this and they'll always have ideas and we're like, just, just try it. Like probably the idea you have right now, isn't going to be THE idea, but that idea will turn into something else. So just start and just try it and people don't because it's like, well, what is someone going to think if we fail? But it's like, who cares?

Joe (15:39):

Nobody cares. I always, yeah. I always tell people nobody's thinking about you, they don't care about you, they're thinking about themselves. And if you don't, and if you don't try, if you don't try, like you'll never know. And failure is really not that big of a deal when you're starting your own company. It's just more like, you know, don't burn through all your personal savings with an offshore developer in like a week because you want to build a product. Talk to customers, figure out where the problems are and, you know, decide how you want to solve it. Test, iterate, and kind of move forward. So that was great advice. I think a lot of people could benefit from hearing that, you know, you just gotta have that initial nudge and figure out what's a problem you want to solve and help people. And then you guys are clearly solving a problem.

Joe (16:16):

I was actually just in Costa Rica and we booked a sailboat one day. Definitely not a seamless process. Didn't know really until the day of if it was going to go through, so completely feel that pain. But more importantly, we had nothing to do on Sunday, “nothing to do” we were at a beach resort, but I would have loved to have been able to book like an activity or at least had the options to book an activity just kind of on-demand that was like convenient and reliable. So it sounds like, yeah, no, it, it’s definitely something that you know, you guys are onto something here. It's just a matter of like, how do you get the eyeballs in front of this? How do you get people to use this? And then how do you grow the marketplace? As far as books, I'm a big reader of business books. What are your favorite books or what's some, what are some books that you would recommend to people who are either considering taking a leap or already starting their own business?

CJ (17:06):

We both really like the book, The Innovation Stack by Jim McKelvey, he's the guy who founded Square. That book's amazing just because he tells the story of how they went up against Amazon and their product and their company won out because of, you know, all these different layers that they added on as they built the company. And I think that's something that resonated with us because like, we didn't really, we knew kind of what we were building when we started, but there are like so many things that like, we always say, like, this took so much time or like we wouldn't have seen this if we didn't meet this person. And those are the things that you can't really just copy by, you know, reverse engineering something. I think it's the whole way that you run your company, um, that makes you unique.

Kaitlyn (17:52):

And then another book that I love is They Ask, You Answer by Marcus Sheridan, and it's a marketing book, and we have a blog, and it just talks about like answering the questions that people are asking so that you can rank higher on Google. And he just talks about the way that he built his business. He's a very smart guy when it comes to marketing.

Joe (18:12):

Very nice. And then there are only a couple more questions. Are there any tools that you guys cannot live without that help you build your business?

Kaitlyn (18:22):

So we use Wistia to send out like videos to people that we're trying to get in front of. Illustrator, it's legit up on my computer right now, that's how we make all of our redesigns through. Slack, obviously. We hate it, but we love it. Our developer’s in California now so we're Slacking him all day.

Joe (18:41):

That's easy. Yeah.

Kaitlyn (18:44):

Zoom, that way we can like, see him. We've never met him in person, but at least he knows what we look like. 

Joe (18:48):


CJ (18:49):

I would say anything that allows you to do videos instead of just cold emails, that's worked really well for us meeting people.

Joe (18:57):

For your outreach to book meetings?

CJ (19:00):

Outreach to book meetings. Yeah.

Joe (19:03):

Okay, great. And then last question, how can people find you?

Kaitlyn (19:08):

They can find us, they can visit our website, Bubbabooking.com. We also have an Instagram page @Bubbabooking and it's me and CJ in bathing suits at the beach, telling you tips on wind surfing versus kite surfing. I don't think CJ ever thought he'd be in a bathing suit on Instagram, but-

CJ (19:26):

It's an, it's not a bikini, so don't worry. And then you can also download the app, both iOS and Android, Bubbabooking tours and activities near me, in the app store.

Joe (19:38):

Awesome. Well, thank you both for joining me today and Bubbabooking.com. Check it out.

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