The Calendar Funnel That Turned Warm Leads into Booked Guests – Founder of STR Insights, Kenny Bedwell Explains

Summary and Highlights

👤 About Kenny Bedwell

Kenny Bedwell is the founder and CEO of STR Insights, a consulting and data firm helping investors locate high-performing short-term rentals across the U.S. A former Citibank data analyst, Kenny started investing in STRs in 2017, growing a diverse portfolio through ownership, co-hosting, and arbitrage.

Today, he’s known not just for deep market knowledge but for his content-savvy presence on Instagram @kenny_bedwell, @strinsights, and as the host of the Cash Flow Positive Podcast. Whether sharing data-backed insights or a Where’s Waldo STR skit, Kenny leads with authenticity and measurable ROI.

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🎯 Direct Booking & Lead Generation

Lead flow first. Kenny’s golden rule: “Your property is not the destination.” Sell the area, not just the stay.

• 📌 Lead magnets that convert: Kenny creates local experience calendars with events, activities, and things to do every day of the year. This free PDF becomes an email lead funnel.
• 📊 Segmenting your audience: After download, he asks if the lead is family-oriented or wine-focused. From there, he delivers tailored content and booking offers.
• 📢 Avoid cold Facebook ads: Focus on building a social presence before spending. Want to retarget visitors later? That’s a win—but only if your funnel is warm.
• ➞ For more on guest trust and conversion, read: 5 Proven Strategies to Build Trust Pre-Arrival

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🪜 Personal Branding That Sticks

• 😀 Make it unforgettable: Kenny’s viral Where’s Waldo skit during a STR keynote helped him realize the power of humor + value.
• 😎 Introvert-approved influence: Despite being shy, Kenny uses his unique voice to grow his brand and differentiate.
• 🎥 Reels that educate + entertain: Follow @kenny_bedwell to see skits that feel more like SNL than a sales pitch.
• ➞ Want to build your own content brand? Start with Building a Social Media Brand for STRs that Converts

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⚖️ Balancing Business & Family

• ⏳ Say no often: Kenny uses a “zone of genius” framework. He hires experts and avoids being the bottleneck.
• 🏠 Set boundaries: Mornings and weekends are sacred for family. Communicating those values builds trust—not resentment.
• 💼 Empower your team: Learn each team member’s goals. Help them win, and they’ll grow your business in return.
• ➞ For more off-peak growth tips, visit: Maximizing Off-Season Demand in Your Market

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📖 Mindset & Book Recommendation

• Mindset advice: Pick a path, say no to everything else, and execute with focus.
• Book rec: The Pumpkin Plan by Mike Michalowicz — essential reading for hosts looking to niche down and scale up.
• ➞ For similar focus strategies, check out: The Direct Booking Revolution

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🎧 Listen to Kenny Bedwell

Catch Kenny on the Booked Solid Podcast or listen to his collaboration with Gil Chan on:

• 🔴 May 20 – Should You Take Direct Bookings?
• 🔴 May 22 – Direct Booking Tactics with Gil Chan

Explore his Cash Flow Positive Podcast and find him on Instagram @kenny_bedwell.

Connect with Kenny:

• 🌐 STRInsights.com
• 🎬 TikTok: likewise @kennybedwell — expect dad jokes with a twist!
  Need the lead magnet templates? He’s happy to share them free. If you’re ready to invest, he’ll help you analyze and close deals—shift from planning to earning.

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✨ Ready to Build Your Booking Funnel?

Let CraftedStays help you create a direct booking strategy for short term rentals that actually works.

📅 Schedule your crafted session today and start attracting the right guests—with the right messaging—all year long.

Transcription

Kenny: And I’m feeding them information of what to do. And so I’m telling them, Hey, you’ve gotta check out this glass museum nearby where you can like cut your own glass and make really cool products. There’s like all these things, I’m like pitching other businesses and stuff and events and people are like, wow, this is a lot.

Kenny: And then I get them in an email funnel and I’m sending them this information and then I drop in. Oh, hey, by the way, if you need a place to stay, here’s the place to stay. If they’ve never heard of Watkins Glen, why they should come to Watkins Glen. And lo and behold. I get traffic, I get bookings, actual bookings, I get actual money from doing that.

Kenny: And that’s the whole point of it. Right? And so you’re, you’re warming people up to why they should come to your area. You’re selling ’em on ’em, and because they trust you, meaning they’re like following it. That’s a form of trust. And they’re reading it and they’re like, wow, this is really cool. And it’s free.

Kenny: It’s not like, oh, I need, I need you to pay for it. I just need your email so I can send the information. They’re now more engaged.

Gil: Hey folks. Welcome back to the book Solid Show, the podcast where we bring in top operators to discuss marketing, revenue management, and guest experience to drive towards being book solid. On today’s show, I have Kenny Bedwell, the founder and CEO of STR Insights. He’s a host himself and has a wealth of knowledge to share with us.

Gil: Today we started to really talk about. How he’s balancing all the different parts of his life. But we started to take a tangent towards really how he’s thinking about direct bookings and how that differs from a, where a lot of folks will focus their attention on specifically in marketing. So I’m really excited to have him on the show and really have him share what he’s learned throughout the years of really marketing himself.

without further ado, let’s bring him in.

Gil: Hey, Kenny, welcome to the show.

Kenny: Yeah, thanks for having me, Gil.

Gil: Yeah, it’s, uh, it’s great to finally have you on here. It’s been a, it’s been quite a, not a struggle, but definitely we’ve been, we’ve been trying to manage our calendars together to, to make this happen.

Kenny: yeah, yeah, yeah. I just, uh, I think I mentioned earlier I was just moved and set up a bunch of properties and it’s been a crazy past two months, so yeah, it’s good. Good to finally connect and beyond.

Kenny: So. Yeah. It’s amazing that, um, even today, like you’re, you’re still buying, buying properties. I think a lot of folks are like, are they holding on the sidelines? And I think also, like a lot of entrepreneurs that get into our space, um, that are not just hosts themselves or property owners, but they’re actually doing something else, serving the market a lot of times, like we kinda get distracted on that stuff.

Gil: Like for instance, like I haven’t been able to acquire for the last year because I’ve been focused on my business. But it’s actually very good to hear that you’re still acquiring on your side.

Kenny: Yeah. You know, um, it’s a, it’s funny, I had, I just had a conversation with, um, someone on my team and I’m a big believer in working with people who have ownership mindset, you know, and so everyone on my team, I call ’em, like, I don’t call ’em my employees. It’s not how it’s structured, you know, like I have, so I have the business at CR Insights, we do data and consulting, and I was, it was always actually speaking to my engineer and he does a bunch of like, side hustle things.

Kenny: And we were talking about like, um, you know, this idea of like, you can’t necessarily put all your eggs in one basket. And expect to be successful. It’s like you diversify your portfolio, but the caveat is you can’t say yes to everything.

Kenny: You know what I mean? You, you, you can’t, you have to be able to know like what’s gonna be beneficial for you and also things that sound like a good idea, but you just don’t have the bandwidth to do so.

Kenny: Um, I understand I a hundred per, I actually put, when I was, uh, in 2023, I put, um, acquisitions on hold until 2024. And so that’s when I started picking it back up again. But when I was growing the business and now it’s like I started to get the right people in the right seats, uh, to kind of help and offset, like, so I don’t have to be on calls all day, every day and I can focus on, you know, other investments and, and family time and other things of life.

Kenny: So yeah. Yeah.

Gil: Yeah. Um, kinda like when I, when I look back at, even from the outside, all the different things that you do, you’re the founder and CEO of STR Insights, you’re a host, property manager. I don’t know what the team of team makeup is there. But you’re also an influencer, and I won’t dive a little bit in deeper into that, but like, and you’re also a, a father as well too.

Gil: Like I, I, for me, I find that really, really hard. Like I’m constantly, my mind is bouncing from one thing to another. I am also a founder and CEOI am also a host. I’m a very, very active father. And I think that’s to my point where like, as an entrepreneur, you’re not just clocking into like your W2 job, you’re having to really evaluate what’s worth it right now.

Gil: And you can’t kinda like your diversified diversification. Like you can’t just put all your eggs in one basket. Like I want to be. The Father of the Year award, like, I wanna win that. But like, at the same time, I’m also, I want to grow my company. I wanna do all these different things. It’s, it’s, that’s a huge challenge for me that I have to evaluate every single day.

Gil: I.

Kenny: Right, right. I, I agree and I think I, you know, it’s, it is priorities, right? And understanding, you know, like putting limits on your calendar and, and those little pieces, I think all, but what you just said is like, if you. Say it out loud and you tell people, and you’re not afraid to tell people like, Hey, I’m a parent first or father first.

Kenny: Um, and also I have all these other hats I wear. People respect that, you know, and, and so when you’re like, Hey, look like I’ve got a field trip I gotta go on, or I gotta go do this or that, I gotta take my kid to school. I do that every day. Like, you know, just stuff like that. Like people, people are like, yeah, makes sense.

Kenny: Go do it. You know? And, and I, because everyone wants that, wants to be that. I think at the end of the day, most people do. And, um, and so for me it’s been just a part of like, just saying it out loud, you

Kenny: know, and, and trying to put it like, not just think I need to put this first, but like literally trying to prioritize it first, you know, and being smart

Kenny: about it.

Kenny: So yeah, I’m definitely pretty vocal. Like, like I don’t hide that. I’m a parent, like behind my, behind my scenes, you can’t really see on the floor, but there’s a huge marble maze, like right there on the Oh, nice. Yeah.

Gil: Uh, so like for me, I am like, it’s also being like proud of, of, of the things that you really prioritize as well too.

Gil: Um, and my, my kids know, like, I probably volunteered at school more than any other parent, but yes, I’m also probably the hardest working probably one of the hardest people in that room. Um, but you just kind of balance, balance it all. And like sometimes you have to take, take away from one, depending to another.

Gil: But at the very end of the day, like I’m still pretty proud of like, just how involved I am as, as a parent. So like,

Kenny: Good, good, good. Cool. Yeah.

Gil: Yeah. Um, so I think like one of the things I mentioned was that you’re also an influencer as well too.

Gil: And I, I gotta bring this up because it, it cracks me up every single time. I, I watch one of your reels, like, Here we go. you, you knew this was coming. Yeah, yeah. No, it’s fine. It’s fine. Yeah. It gets brought up a lot, but go ahead.

Gil: No. Like, dude, like, I, I don’t know how you sustain that. And just like, I, you live definitely the, all the dad jokes and, and just the, the vibe there, but what, what kind of led you down?

Gil: Like, it was almost like a, not a switch, but like, there’s almost like a, a wake up one time where your post prior, maybe a year and a half ago were just like anyone else’s post. And now it’s nothing like anyone else’s post. So talk to me about that transition.

Kenny: Uh, yes. Okay. So I am a really, really big numbers guy, and especially when it comes to dollars that you spend and as doing a startup, any dollar that I believe, any dollar that you spend it needs to have some sort of ROI like accounted to it. And, um, I, uh, about a year and a half ago I was. Paying for a videographer, I was paying for someone to post reels or whatever for me on, and I’m not a big, I’m really not a big social media person.

Kenny: I, it’s, it’s kind of, I, I, you could, everyone’s like, oh, your stuff’s so funny. If you, if you don’t follow me on social media, it’s at Kenny Bedwell. Just go look at my past post and you’ll, you’ll get what he’s talking about. But, um, I, I was just kind of posting like, I was like, here’s the facts. Like here’s what you need to know.

Kenny: Like, I’m a very, like, here’s, you know, let’s lay it down, bullet point, like boom, boom, boom, efficient. And, you know, I was just noticing it’s like a hundred people watched it. I’m like, that’s like nothing. You know, like I’m seeing all these other people who have like thousands of followers, thousands of views, and no offense, I don’t think what they have to share is like that valuable.

Kenny: You know, it’s just like kind of basic stuff. And I’m just like, I’m giving pretty good information. I don’t know why, like people aren’t really responding to it. And I went to an event, um, some, and sometimes I get in like these like creative head spaces where I’m like. I, I need to go embarrass myself or do something stupid. Um, and so I went to an event and I did a, i I was gonna speak on where are the best STR markets to invest in? And I walked up on stage, uh, and I was wearing a Where’s Waldo costume, head to toe hat, glasses, shirt, pants, everything. Head to toe. Where’s Waldo? And the whole presentation was themed. Where’s Waldo?

Kenny: But all around were the top SCR markets. And people thought it was so funny, they wanted to take pictures with me. They wanted to, um, like people were all engaged in the presentation. And it was just like, and then afterwards people were still talking about it. Like, everyone who’s been to that event, they bring that up today.

Kenny: They’re like, Kenny, you remember that time? And I was like, yes. I remember that time. Like, you know, like, it’s like this thing that happened. And um, and it was like talked about and it dawned on me. I was like. Don’t go, like, don’t just like do the boring stuff. Like people want, like some sort of entertainment or something catchy that makes it fun and exciting and brings out like the awkwardness and the weird humor that you, that you uniquely have, not necessarily the same humor as somebody else.

Kenny: And so that’s really where I was like, okay, I need to start doing that in social media. Um, and, you know, publicly embarrass myself because that’s how I feel about it every time. Like every I get, I’m like, I gotta pump myself up before I do. I’m like, all right, I gotta go sing some stupid song, or do some stupid dance or do something embarrassing.

Kenny: And, uh, but you know what, like people will love it, enjoy it, and they’ll remember that stuff and, and have a chuckle from it, you know? And,

Kenny: and everyone’s better for it. So, yeah.

Gil: I definitely have a chuckle on it. There’s, there’s, I, I don’t know anyone in the industry that does it quite like you do. Um, and like if you think back, like high school, if, if you were to meet anyone from your high school class, would they associate that person to who you are, to who you are at least on, on Instagram today?

Gil: Or did you actually have to like, change your behavior and kind of get yourself out of that shell.

Kenny: Um, I think there’s definitely, like, I definitely need to get it out, out of i, out of my shell. So like, I will s this might be hard to believe, but I am naturally an introvert. And, um, like, so the way I know this is when I go to events and conference, just networking things. Like, at first, like I have to warm up, you know, I gotta like go and like, I’m like, oh man, I gotta to like go talk to people, you know?

Kenny: And like, same thing with like, um, and I’m always like exhausted afterwards, you know, I’m like, oh, that was so much. Uh, and everyone’s like, oh, well you speak and you do all these. And I’m like, yeah, I just do it so much that you get used to it. Um, but I’m still like, that’s not like what I. Love, you know, like with, if I could choose to, I would not.

Kenny: It’s the same thing with social media. And so growing up in high school and then even college, like maybe I’d take a picture and post it of me smiling with some like, awkward thumbs up. But like, that’s it, you know? And so I think people who knew me well, they knew I had some of this humor, like talk about it, but then like, seeing me execute on it, they’re like, whoa, like, what’s going on? So it’s so funny. Um, and what’s, what’s even better though, is in the community or like if I go to church or, or just public places where people don’t know who I am, you know, from a business standpoint, they just know, like, you know, like they have no idea. And then sometimes I’ll see one of them catch up and be like. Hey, I found you on social media. And I’m like, oh boy. So, and then they start, they love it. They’re like, actually, I really like it. Oh. So it’s, uh, it’s always a fun, fun conversation, but, uh, yeah, it’s, it’s different than maybe my more like, uh, normal, what people see in my day to day.

Kenny: So Yeah. Yeah. I, I wonder, um, I don’t know if your kids have seen any of your reels before and, and their reaction to what dad looks like on, on social media.

Kenny: Not, not yet. Not yet. They’re not old enough yet to quite like, connect the dots on it. So, so one day they’ll be like, what? Oh, my wife, she’s like the biggest, like, she’s always like, you’re, you’re an idiot. Like, she’s like, no one, no one, no one thinks that’s funny. I was like, trust me. They think it’s

Kenny: funny. yeah,

Gil: I, I think that’s our job, though. I think that’s our job to kind of chain tame you down.

Kenny: yeah. It’s true. She tries to give me ideas and I’m like, okay, no, that is. Is literally the lowest of lows that I could be. So I’m not gonna do that. So,

Gil: Do you come up with your own skits or do you have kind of your, your team to kinda help you out there?

Kenny: um, I come up with a lot of this stuff, believe it or not. Uh, sometimes I’ve started to get requests. I’m like, yeah, why not? Like, that’s pretty funny. I’ll do that. And other times I’m like, eh, that’s not me. Um, and so some people will send, people send me stuff all the time. They’re like, Kenny, can you do this?

Kenny: And they’re like, this would be so funny. And I was like, yeah, I’ll try that. Um, but yeah, I’ll come up with my own stuff. I’ll follow other people who do like in the real estate industry and some of the skits that they do, and I’m like, oh, I can do that. Um, so I get a lot of like, different ideas. And then sometimes my team comes up with ideas too.

Kenny: So,

Gil: Yeah. Yeah. Yeah. That’s awesome. But, Um, yeah, I

Kenny: by ’em where I’m like, Hey, like, is this too, is this over the line? Is this not? Like, how far are we gonna go here?

Gil: is is there really a line though, at this point?

Kenny: Well, you know, I’ve got a couple that I’ve been saving. I might, yeah, I’ll, I’ll do, I’ll do one and send it to you. Be like, I think I crossed it here, but

Gil: I, I wanna see that because like, I almost feel like there’s no line that cannot be crossed at this point other than like, indecency. But,

Kenny: yeah, there you go. Yeah, that’s, that’s fair. That’s very fair. Yeah,

Kenny: it’s, uh, it’s, You gotta, you gotta share with me the next time you, you have a, you have a, a wacky idea. I wanna see it.

Kenny: I, yeah, all I, I’ve got a couple saved that I’ve just been hold on to like, just, it’s a confidence thing. It’s like I gotta, I gotta, I gotta do it. I just don’t know if I have the guts to do this.

Gil: Yeah.

Kenny: anyway.

Gil: I want to get back, I want to get back to kinda like what you were saying earlier about the different parts of your life. And I wanna understand kind of like how you’ve created the structure that allows you to do all the things that you want to do. Um, but before I go there, I want to catch our listeners up that might not know.

Gil: All the things that you’ve kind of built over the years. So talk to me a little bit about your portfolio, which you’ve grown so far. I definitely want to hear kind of how you’ve started SDR Insights in the first place. So talk to me about that.

Kenny: Yeah. So I am, first and foremost, um, I am an investor that’s, I like to consider myself a hundred percent investor, meaning I own my own properties, I manage my own properties or with teams, um, or business partners. I, I am a hundred percent investor and that’s always been the goal. Um, I worked at Citibank as a data analyst.

Kenny: I’m not, you know, that’s about as exciting as it got. Uh, and, uh, I, I was able to kind of, uh, start investing in real estate, uh, in 20 20 17. And that’s when I got my first short term rental and started growing a portfolio from there. I did rental arbitrage, I did co-hosting, I did property. Like, I, I tried a lot of, dabbled in different things, um, and it was good, but I always was kind of this eye towards, you know, being an investor and growing a true portfolio and having, you know, inevitably financial freedom of however I define what that means.

Kenny: And so, um, I, in 2021, I started SCR Insights and it really started from me gathering data and using the skills and techniques I learned from what I did at Citibank, um, and applying that into. Our space for finding short term rentals in markets of where to invest in. One of my biggest problems I had early on was just knowing where to go after.

Kenny: Like when I grow, like meaning like, I wanna buy a property, but my local, my backyard doesn’t make sense, and the markets I’m looking at, maybe they’re too expensive or, you know, it just, it’s not feasible. So where can I go, where can I invest? And I was able to pull data from various sources and put it together to understand the best markets, the most affordable markets.

Kenny: That gave me the best ROI to invest in. And I started buying properties like that. And I was in some small investor groups, uh, for short term rentals. And I shared that there’s just spreadsheets, the spreadsheets, with everybody, and people started making investment decisions based on ’em. And they started making a lot of money, especially the ones who had a lot of money to begin with.

Kenny: They were like, wow, I just bought this house and it just went from x, you know, 1.1 million. Now it’s worth like 1.8. And I just grew, you know, netted a hundred thousand dollars on it, or 200 or whatever. And just all these like really great things. And people were just like, Kenny, like this group was like, Kenny, this data needs to go out to the rest of the world.

Kenny: Like you need to make this public. And so that’s where like they really pushed me to start and start a business, a data company originally. Um, and then that’s what I did. I started SDR insights. And lo and behold, what I found though is people, the data was helpful, but they were still struggling to kind of get the results and finding the properties.

Kenny: And so I, I went more consulting. And so right now we focus, we have data, but we also have, we do a lot of consulting and I help people identify markets that fit them and properties. So people in 10 31 exchanges, people who are looking to buy their first ones, who have analysis paralysis, just looking to find that property that’s gonna make money. My job now is to help them and we actually go and identify those properties and help them negotiate and get the teams and the resources to be successful. So that’s what we do today. Um, and our goal, my goal personally is to help people feel confident in the decisions they’re trying to make and have a good property that’s gonna work towards their goals. So, yeah.

Gil: awesome. That’s awesome. Yeah. I, I, I think just as you’re starting at D sites, I think even before you went public with it, I think it was really hard for me to buy and get into my first property and I ended up purchasing in Gatlinburg and it was actually a, a good decision. It was right at the right time.

Gil: Um, and I don’t regret it whatsoever today, but like in the very beginning. I still remember that first analysis where I was scraping Redfin and Zillow and median prices, and then comparing that to, um, air DNA and comparing like, okay, what, what is that sweet spot of how much I’m gonna invest into and the type of properties in terms of returns there?

Gil: And just trying to figure that all out. And I, I went down a similar path of view of like sharing that with my community, but like, I don’t think I was quite as, I, I don’t come from a data background, like that’s, that’s not my, my forte, but like I had to try to figure out all the different pieces to figure like how to dive into it.

Gil: So it makes a ton of sense that like you kind of went down that path and it feels like it’s almost a little bit of serendipity that you went into where it was your background, the right place, the right time, this huge influx of events, investments coming, coming in, and you were just in this almost like an incubation of a ster size was bound to happen because of that.

Kenny: Right. Yeah, yeah.

Kenny: yeah. And it, yeah, it was, uh, yeah, it was, there was a lot of learning lessons and we, like I said, we pivoted, we pivoted away from just doing data. Um, because I, I just kept, remember I’m an investor first. I kept seeing people, they’d pay for access to the data, which is great for the business, but then they just couldn’t get the result, which is the

Kenny: property. And they just needed a person with experience to look at it and go, Hey, this is a good deal and here’s why. And, um, once we started doing that, um, we really started to see a change in the business, and especially growth. Um, you know, uh, you know, obviously people come and they pay us. They pay us a lot more money to help help them find properties rather than just a subscription to the database. Um, but we’re now hearing success stories. You know,

Kenny: it’s like, I use SDR insights, but I use the team and I have relationships with these people, and that’s also helped me too, connect and, and grow my own portfolio, because now I’m meeting people and just kind of, you know, it’s more relationship built. So,

Gil: Yeah, you, it also feels like you’re also getting that feedback loop of like, okay, you’re not just giving advice out there, but then you’re also seeing them actually play out over time. Because if you’re just the data company, you only get the input side of it. There’s no feedback loop. But I, I, I feel like right now where you are doing consulting on that, you’re starting to figure out like what’s actually working for which folks, which assumptions that you made that are spot on, which ones could have need adjustments or which one were you off by actually where you underestimated the impact of something that could have been bigger.

Gil: And each one of those iterations, you and your team is getting better and better at really figuring out what is that right recipe for successful investment.

Kenny: Right. And it also puts you in a place too, where you’re forced to basically look for deals. So what happens when you’re looking for deals from other people? You go, maybe I want that one. You know, like, wow, that’s a really good one. Like, I want that. And that’s exactly what we’re doing. Like I, it’s funny, I, I, I, um, I tell my clients all the time, I said. If I call you and I send you this property, and I say, if you don’t buy it, I will. I’m not kidding. I will buy it. Like, and, and I tell, like, I share stories, I’m like, this one, like, show ’em these properties. And I said, these are ones that people looked at. And they just said, you know what? Like, I don’t know.

Kenny: And then I told ’em that and they were, they thought I was kidding. And then they go buying it, setting it up and launching it. And they’re always like kicking rocks up and they’re like, I dang it. I wish I had bought that one. Like, oh, I should have just done it. And you’re just like, I’m sorry. I dunno what to tell you.

Kenny: Like, so

Gil: I gave you first right of refusal.

Kenny: Yeah, exactly. Like, you know, and it’s, I was the one who found it, but, you know, so I, I, I think that, um, that, and that’s, that’s, that’s a great part is like I get to, I get to be in it, um, with other people kind of side by side rather than just like, oh yeah, like here’s some data. Good luck. So,

Kenny: but uh. Um, kind of like, I think that’s a good primer to the, the second kind of question I had for you was like, so you’re all, all of these different things. You’re the host property manager, you’re, um, acquiring your properties, you’re setting them, you’re setting them up. Um, you’re also the founder and CEO of your FDR insights.

Gil: Like how do you and, and a, and a family man as well too, like how do you balance all that stuff? Like how do you make sure that you’re, you’re not burning out yourself.

Kenny: Yeah, a really good calendar. So funny, funny love look. Um, about a year ago I, uh, started studying this concept of zone of genius. Like what is your zone of genius? Not before, sorry. Let me disc claim this before I go into anything. I don’t have anything figured out, like to a t I’m not a perfect person. I don’t have my life perfectly juggled.

Kenny: I think that’s really important to say. ’cause I don’t want people to think like, oh, I’m, I’m like a magician and have everything figured out. I really don’t. Like, I have some things figured out. Um, but it’s like, it’s a work in progress, right? And I think that does really important. We need to, number one, recognize how far we’ve come with gratitude, right?

Kenny: Be grateful for how far we’ve come. Um, but then also realize like, we have improvements. We can continue to make, you know, we’re not perfect and we never will be, but we can improve. And so that I’m still improving. Um, but here are the, here’s the progress that I’ve made that I’ve been able to recognize. So number one, one of the biggest things I’ve learned in my business is focus on what you’re good at and get other people who are good at the other things and then get out of their way. Micromanagers or micromanagement essentially. Is one of the biggest bottlenecks in your business? One of the, like when I realized I was the biggest bottleneck in my business, it was just like this eye-opening experience for me to realize like, how can I get out of my own way and put the right people in to take care of these things for me? So, you know, you, you mentioned you manage your own properties. I do manage my own properties, but I don’t communicate with guests. I don’t do my own pricing. I don’t clean my properties, I don’t maintain my properties. But I don’t have a property manager because I’m just the CEO, I’m just overseeing these things.

Kenny: But when it comes to like what amenities I should add and you know, like the maximizing return on investment, that’s where I step in because that’s my strong suit. But I surround myself with the right people who are, who are the experts at what they do. You know, and that’s something important to understand as well, is I don’t look for Swiss army knife individuals to be on my team. I look for people who are really good at like one, maybe two things, you know? And it’s like, look, you can maybe learn something else, but a Swiss Army knife, someone who’s like supposedly good at everything, they’re really not good at one thing in particular. And I want the best of the best. And that’s kind of one of the lessons I’ve learned as well as surrounding myself with the best of the best to, that I can find in specific areas to take that off my plate, because they’re gonna do way better than I ever could.

Kenny: You know, I can be a Swiss Army knife too, but it’s just not as effective in my business. And so tying all that in, getting outta my own way, frees up a lot of time, you know? And then also just having some like, set like rules with my family and saying like, okay, these are the hours I’m gonna be working. Um, you know, and then I’m gonna take weekends off.

Kenny: And then if I travel, you know, I’m only gonna be gone for 24 hours. And like, just all these little things. It really helps, it allows me to be able to be more present, especially during important moments. You know, in life. So

Gil: Yeah. I think to to one of your points of like really finding the right folks, what’s been kind of your approach towards talent acquisition? Like where do you seek. Or maybe they come to you of like, how do you find the right folks to help you build that army around you?

Kenny: man, that is a multimillion dollar question right there. Multi, not million, multi. And if you can figure that out, you’ll be a very rich man. But in my experience, the best people, um, that I hire are usually either people that are like, I vague, like I will post, like I, the, I don’t do job postings. Like I don’t do complete strangers because

Kenny: whether I know them or not, that’s not, not the point.

Kenny: But it’s like, I don’t do job postings because they’re a bunch of people who kind of come outta the woodworks who maybe aren’t necessarily qualified or, or. Okay. Character and, and, and attitude. Like all these things like kind of play into it. Um, what I have found that works is internally like networking and spreading the word, Hey, I’m looking for someone who does X, Y, and Z. Um, you know, who do I like? Just telling people about it and usually they might know someone or whatever. And I found people through that. Um, and just being very cautious. Also not like one, one of the lessons I’ve learned with a, with a small business is, um, you know, hiring people on full-time, like W2 benefits without knowing like what they’re capable of actually doing. You

Kenny: know, it’s like the people can tell you all day long, like, yes, I can do X, Y, and Z, but until they prove it, you don’t really know it, you know? And so it’s like you gotta protect yourself and it’s, it’s a gamble to hire anybody. And so for me, um, it’s feeding, you know, finding these individuals and then feeding them smaller tasks at first to kind of test the waters.

Kenny: Before you have like a formal like bring on relationship. Once I started doing that, I, it started clicking where I started finding people. I was like, wow, they’re really good. Like, I want this person to stay on my team. Like, what can I do to keep them on my team? Um, being very transparent with them and trying to help them be successful.

Kenny: One thing I started to do in the last year with, with everyone I work with is I try to learn their goals. What are you trying to

Kenny: accomplish in life? You know, what are you like, is it, you know, like one of my, you know, my sales rep, she’s like, I just want to go on a cruise for a week, you know, once a year.

Kenny: And I’m like, okay, well how much money do you need to make? I need to make X amount. Okay, cool. Like, let’s, you know. And then each month I’m sitting down with her, how much money did you make this month? How, how can we make you more money? Like when you want your people to be successful, they’re gonna make you successful.

Kenny: So I, I’ve stopped worrying about what’s my success and I’m worried about their success and. Boom. Like the business is gross and it gives me more time to not have to worry about things because they reciprocate. You know? They’re like, well, what do you want? You know, what are you trying? It’s like, it’s like this, this atmosphere where everyone’s trying to help each other and it’s just lifting.

Kenny: It’s lifting where you know where we are all together rather than just like one person excelling. So,

Gil: Yeah, I think that’s, that’s such a powerful management. Um, I don’t know if technique, is it belittles it because it, it’s, it’s more than that. I think when you really care about your team and you understand what their goals and ambitions are, and we started doing this ourselves, uh, at Kraft Estates where.

Gil: I told them what my goals were and I was very, very honest about like both the company ambitions, but also my personal ambitions, like the places I want to take my kids. And, and in order for me to really feel comfortable doing that, like the revenue targets that I, I want to hit for me personally, and like if I don’t hit those revenue targets, I don’t get a chance to, to take the trips that I want to take because I don’t, I didn’t, I didn’t earn it.

Gil: Um, and like when I was being that transparent with my team, they understood like where one and where I was headed and two, kind of like the, the driver for it. And I encouraged them to share what their ambitions are. And I, I was surprised to find out like some of the things that my team was juggling on the side and the things that, the ambitions that they have and why they’re doing that thing.

Gil: I had one of my team members asked, tell me that they wanted to start a business and I was like, whoa, I did not know that you wanted to start a business. Um, and I dug, I dug a bit deeper on like, what kind of business are you trying to do? And kind of the reason why, and I ended up finding it that he wanted to start a business because he wanted to really make sure that.

Gil: His grandmother had something to do that met, made him, made her like, continue to thrive, even in the elderly age. And I was like, wow, that’s amazing. Like, how can I help in that? And just like, just checking him in with him every so often.

Kenny: Yeah. Yeah. I, I mean, if you approach it from a, how can I make them successful, and you’re worried about that, that will, like, you’re, you’re basically problem solving with them, but it impacts you in a positive way as well. It’s not, how can we make more money or the company make more money? It, it’s like, how can I make you more money? You know, and it’s not, oh, just gimme a pay raise. Like that’s, and that go, going back to your original question of like, how do you find the right people? I look for people who have an ownership mentality. I don’t look for the employee mind, meaning like, check clock in, clock out. You know, what’s, what’s this?

Kenny: You know, like I just want an hourly wage. You know, we do have hourly people, I’m not saying we don’t hire them, but like even our hourly people, they’re mo like, I give them incentives to make more and it’s like, ’cause they want to make more. And I ask those same questions of them. What do you want to obtain beyond just money? What are your goals? You know, one, our youngest employee, she’s like 20 years old. Um, and she’s, she wants to, you know, be, have a full on property management company. And right now she’s like managing her, her parents’ properties and she’s like trying to make calls, like cold calling people and stuff too. And you know, I just said, look, like, you know, we have clients who need managers.

Kenny: You know, it’s a good opportunity for you to introduce yourself and, and start that and be there. And she know she’s really excited about that. We’ve made several connections to her already. And so that, like, that, those little things goes beyond just a paycheck, you know? So

Gil: Yeah, and I think that kind of goes back to like the, the major theme of what you said earlier about really finding the talent in the right, in, in the first place. I think I, I’m starting to realize more and more that I think the folks that are successful are the ones that vocalize where they’re trying to go, what they’re doing, and really talk about that pretty openly about what their, what their ambitions are.

Gil: I think if you have, if you’re surrounded by the right, with the right folks, you sharing that isn’t being boastful or, or what, but it’s really allowing other folks to kind of help you in that journey.

Kenny: Mm-hmm. I love it.

Kenny: Yeah. Um, slight, slight tangent there. I, I, I, I definitely want to kind of dive into kind of some of the strategies that you have and that you’ve employed on the direct booking side, but maybe before we go there, there’s, in the last six 18 months. A year and a half or so, there’s been this big rise in, in ai, um, and I’m, I’m sure you’ve seen it all over the place, but I’m interested in hearing kind of how that has impacted your business and kind of how you do, how you do what you do.

Kenny: Yeah. So over a year ago, we actually implemented an AI tool into, we created our own like integration essentially with, uh, Chad GBT into SCR Insights data. And so basically what you could do is communicate with a chat bot and ask it questions that had our data, and you could ask the questions, here’s my budget, here are my goals. You know, where should I invest? And it would tell you the markets, and you could ask it, where in the market should I invest? And it would tell you the zip code and the type of property you could get. You know, it’s like you should buy a three bedroom, two bath in this market and this zip code in this market. And, um, you know, here are the types of amenities that property needs to have. So, really cool. Like, and, and this is the entire country, you know, if

Kenny: you’re like, I mean, it would like, it’s like 12 over 12,000 markets in the country and like, it, it had it all. The problem that I noticed in the vacation rental space is that people aren’t quite there yet with understanding how to use the ai.

Kenny: So we had like very, very tech savvy people eat it up and leverage it. But everyone else was kinda like, you have to break this down to me, like I’m a 5-year-old, which is fine. I get, it’s

Kenny: new, it’s new technology. And so. The AI component, it we’re, we realized like people just weren’t there yet and they

Kenny: weren’t able to like fully leverage the power of it on a general level. Um, and so we took it out, you know, and believe it or not, like, I mean, we tracked usage and everything and it just really wasn’t like beneficial, you know, and it was costly. And so we took it out and maybe in the future we’ll put it back in if it becomes more like useful. But I think people have to be taught how to like, use ai. Um, especially in our space. I think we’re, we’re kind of, we have a bit of a laggard, I call it la you know, the tech adoption timeline. We’re like laggards, like most people in the short-term rental space are laggards towards like certain technology. And, um, I think it’s time to like, you know, we’ll, we’ll get there, people will get there, but it, we just have to understand where people are at and to, you know, get, uh, get excitement around it before we go all go all in.

Kenny: But there’s some really cool resources and tools out there, in my opinion,

Gil: Yeah. Yeah, I a hundred percent agree with you on like the the taught AI thing where I think a lot of folks are playing with ai, but they’re playing with ai. Not in the most productive way to play with ai. And I think that if you do understand how AI works, how you’re able to leverage it, it actually could be much, much more powerful than folks really realize there.

Gil: Um, and I think like, not not to put down or, or anything, but like I see people using AI to generate images or, or, or, or whatnot. Um, and there’s actually a lot more power there, like what you’re just talking about, of leveraging AI to comb through thousands and thousands of rows of data to synthesize it to really, I see it as like almost like bridging, bridging almost a technological technological gap and an execution gap there.

Gil: Whereas like if you did not have ai, it would’ve been really hard for you to write a SQL query that helps you understand all those different things and help you filter around ex exactly what you need. But with that, you now have a much more powerful tool that. It is much more accessible, but at the same time, I think folks aren’t really understanding really how to tap into that just yet.

Kenny: Right. And one of the biggest places people can start with ai, this is one of my tips for everyone to do with their market research. Any research whatsoever go into comparable properties, reviews on Airbnb, VBO, whatever, copy their reviews, and paste in the ai, and it will tell you so much valuable data. Um, one of my favorite things to do, like, especially for those of you, you know, like we’re, we’re talking about direct bookings coming up.

Kenny: Like, you know, what, where are people coming from? If you’re gonna do direct bookings, you need to, like, all this is like focused on your target audience and your, you know, who you’re trying to target. Well go grab an Airbnb. When you have the reviews, it says where the people are from. You know, grab that or grab, copy the reviews, throw in the chat, GBT, and it will literally tell you like, where do most people come from?

Kenny: What regions or cities or whatever. It will summarize everything for you. And Airbnb even tells you like, they stay with kids, they stay with a pet, they, you know, like group trip or whatever. And it’s like you can get so much good data from that, uh, to be able to leverage for your plan of how to attack direct bookings.

Kenny: So I, I just think that like, starting with the reviews and then not only for direct bookings, but also like market research. Like what amenities do people, like, they’ll tell you in the reviews what, um, what do things, what do, what are things that people don’t like about these properties? You know, they’ll tell you in the reviews.

Kenny: Like you, you’ll learn everything you need to know about what’s important. And what isn’t in the reviews. It’s a really good data point, and I don’t see many people leveraging that. And you can get hundreds, thousands of reviews because these markets, there’s thousands of properties and you can just learn so much and chat.

Kenny: GBT can summarize it for you in seconds,

Gil: Yeah, I, I think that, that, that’s a very strong point where I think the folks that have harnessed AI is really around really knowledge understanding there. It’s not necessarily just like content output, but like if you’re able to leverage AI to be. What I’m starting to realize more recently is being almost a companion to you.

Gil: Someone that’s sitting next to you, that is an expert at a lot of different things. Actually using it to go back and forth. Like if I were to go to you, I wouldn’t just say, Hey Kenny, I wanna be able to learn this. And just like dump everything. Like if we were having a conversation and I’m trying to learn, learn like how do you do deal analysis for a brand new market that you never got into?

Gil: We’re probably gonna go back a few times. You’re probably gonna gimme a high level summary about things. You’re gonna break down different tasks. I’m gonna start to ask you different questions and we’re gonna probably the, the conversation’s gonna lead in very different ways based on what I already know and what I need to know there.

Gil: And I think like if you’re able to leverage AI where you can actually have a conversation and actually have them give you a high level summary, dive deep into certain things that you really wanna learn more about, you’re able to gain a lot more knowledge that is tailor specific to what your end goal is.

Kenny: Mm-hmm. Yeah, I agree.

Kenny: I Yeah. And I, I definitely agree with you on the whole review things. We actually, we have a prompt here where if I’m working with a client and we’re trying to figure out the, their brand, we will actually extract their reviews and figure out who’s staying at their properties, where are they coming from, what amenities do they like, and we use that along with like Donald Miller’s like StoryBrand to figure out like, okay, who’s the avatar that’s going there?

Gil: How do we create a persona where when they land on the website, it feels like the website is made specifically for them. And that’s kind like how some of our clients use ai.

Kenny: Mm-hmm. Yeah. Yeah. I love it.

Gil: Awesome. Um, can you, moving on to like the, the direct booking side, what’s some of the things that you found that worked really well for you, uh, while you’re building your direct booking engine? I.

Kenny: Yeah. So the, the, the biggest que, so I mean, there, there’s a couple components to it I want to focus on. So there’s, you know, getting it set up and like getting your repeat guests to use it and everything. And I’m sure you’ve probably had people talk about that before. I wanna talk more about if it’s okay, I wanna talk more about lead generation because. I as someone who does stupid stuff on social media to gain followers and attention and traffic. Um, and also I’ve tried a few things from my end too with my own properties. I, I’ve learned a lot about lead generation and I think I actually have some really good tips that I wanna share on here about that.

Kenny: And so I’m gonna focus on that like more so on the lead side, uh, for direct bookings, because I think that, um, you know, the site’s really important, but if you’re not getting the traffic to the site, it’s like, what the heck is the point? You know?

Gil: Yeah. Yeah.

Kenny: So that, like I said, everything you do has gotta have an ROI that’s, that’s in my head.

Kenny: I’m like, I’m gonna do this. It’s gotta make me money. Um, so for me, one thing I realized is like, you are essentially, so number one, this is a business, you know, surprise, spoiler alert, this is a business, right? And you’re selling a product, it’s a service product, right? So you’re selling a, an experience.

Kenny: Your property is stay at your property, whatever. And. You know, you need to market it as such, but you have to understand the leads in lead flow. Every business has leads in lead flow and it varies business to business. And, um, I see a lot of people talking about, you know, Facebook ads and marketing and things like that. I personally, based on my experience, do not believe in running Facebook ads to my direct booking site because it’s never worked for me because of who the types of leads are. And what I have found is that those leads at Facebook, I’ll get clicks. People will click on my site. Oh, that’s really cool. Maybe they’ll comment on the ad, oh, that’s a really cool property, but they won’t stay.

Kenny: I’ll make zero money from it. And it’s like, well, I just spent, you know, a hundred bucks or whatever. Um, and you know, people are, oh, well you need to spend more money. And it’s like, no, I need to get conversion. So what I have found is that in order to get direct bookings. You know, from leads, we need warm leads.

Kenny: We need people who are interested in coming to the area and who are looking for a property to stay at. Too many people are trying to like, pitch their property as like through ads or social media. It doesn’t, it doesn’t have to be specifically ads. It could just be like a TikTok video or, or Instagram reel or whatever on like, Hey, this is my cool property. But unless it’s crazy unique, people don’t really have a desire to just go stay at a nice luxury place in the middle of like somewhere that they weren’t planning on going to. So the first lesson I want everyone to understand is that your property is not the destination. If you can, if you wrap your head around that meaning like people aren’t coming to your market to stay at your property because of your property. They’re coming to your market to do something in that market, to have an experience, right? So you just going online and trying to pitch your property is trying to say like, Hey, come to, you know, uh, I’m gonna, I’ll pick some random vacation markets that are super obvious, like, come to the Smokies because I have a really cool cabin.

Kenny: And it’s like, no, go to the Smokey’s because there’s a national park there. There’s, you know, all these things to do in the area, Dollywood, uh, you know, all this stuff. And it’s like, and then the cabin is, supports the experience of what you’re gonna have here. And, and so when I see people trying to like, promote their direct booking sites on Facebook or whatever, uh, on social media, at least it’s, it’s trying to say, come to my property because it is the thing to come to, and that’s not the case.

Kenny: And so number one, lead flow. You need to warm people up to selling the area. In the experience rather than the property. So what I personally do, lemme give some examples. What I personally like to do is I will run ads, but I’ll run ads of top things to do in my area, in my market. And the point isn’t to sell the person on the property today is to sell them eventually, but I have to convince them to come to the area first.

Kenny: So, for example, the one that I do this on is Watkins Glen, New York. I don’t know, have you ever heard of that market before?

Gil: I have not.

Kenny: No. So if I just sent you images of my property, it’d be like cool property, Kenny. But my family and I are probably not gonna go there or plan a trip there. However, if I said, you know, Hey, we’ve got this check out, this really cool. State park. It’s like a, it’s like caves that you walk through and there’s waterfalls. It’s really, really pretty and gorgeous. This area, it’s right on a lake. You can go boating, swimming. There’s the hiking through the, the, the, the state park trail thing that’s got all the waterfalls. There’s a NASCAR stadium nearby. Um, you, you probably don’t drink wine, but there’s wineries there too. But you know, like there’s, there’s different avenues, but like literally it turns into like, Hey, my family can go to a NASCAR race. And they have like a, a, it’s not just nascar. They have like Ferrari racing and, uh, they do a, um, it’s really cool.

Kenny: They do, what are the, the, the punch buggies where they, the, the, the, not BMWs, I’m thinking the, you know, the small, like the bug cars, you

Kenny: know what I’m the mini.

Kenny: Yeah. The, yeah. The many. Yeah. They, they’ll do those like racing, just of those, um, and they’ll do a race through the town too. It’s, it’s like there’s a lot of cool stuff that goes on there on top of all these outdoor stuff. Uh, you know, as I’m pitching this to you, you’re like, that sounds kind of cool, you know, and you’re like, maybe I could go, I, you, you still probably won’t go there, but it’s fine. But like, it depends on how far away it is, but

Gil: probably more the thing, how far it away it is.

Kenny: it, well, that’s a huge component of it. So if I know who, where my people are coming from, so like, it’s in New York, okay?

Kenny: So the people that go there are in Pennsylvania, New York, New Jersey, Vermont, New Hampshire, and that’s who I target. I don’t target people in, you know, west coast, Southeast or whatever. They don’t wanna go to New York for that. So I target that area and that’s fine. And I’m convincing people why, if they’ve never heard of Watkins Glen, why they should come to Watkins Glen.

Kenny: And I’m feeding them information of what to do. And so I’m telling them, Hey, you’ve gotta check out this. You can go, there’s a glass museum nearby where you can like, cut your own glass and make cool, really cool products. There’s like all these things I’m like pitching other businesses and stuff and events and people are like, wow, this is a lot.

Kenny: And, and then I get them in an email funnel. All, and I’m sending them this information and then I drop in, oh, hey, by the way, if you need a place to stay, here’s the place to stay. And lo and behold, I get traffic, I get bookings, actual bookings. I get actual money from

Kenny: doing that. And that’s the whole point of it.

Kenny: Right? And so you’re, you’re warming people up to why they should come to your area. You’re selling ’em on ’em, and because they trust you, meaning they’re like following it. That’s, that’s a form of trust. And they’re reading it and they’re like, wow, this is really cool. And it’s free. It’s not like, oh, I need, I need you to pay for it.

Kenny: I just need your email so I can send the information. They’re now more, they’re more engaged. And if you’re sending it over and over and over, you slip something in, it doesn’t seem like a sales pitch or like, Hey, it is just like, oh, wow, yeah, I could go to this place too and it’s got everything I need and we can enjoy this.

Kenny: Yeah, let’s like book this now. You know, and you can do discounts and things like that. That’s given me the most success and generating cold traffic to my direct booking site. From, I, I say cold traffic, it’s really not at that point, it’s now

Kenny: warm, you know, but it wasn’t friends and family warm. It was like complete stranger warm. Um, and I just found that, that like creating, they’re called lead magnets, free ways to track people in to why you should do that. And you don’t have to do emails. One of my good friends, he does, uh, he, he created a Facebook group called the, um, the Bourbon Sherpa. It’s in Kentucky. On the Kentucky Bourbon Trail.

Kenny: He started a Facebook group. All they talk about is, uh, bourbon, drinking, bourbon. Well, all the distilleries there, there’s tons of distilleries in like 50 distilleries in this area. He’s, his, his main source of income is short-term rentals. Okay? So he doesn’t talk about short-term rentals. In this group, he talks about bourbon and people see him as the lead expert on like tours and things going on in the area.

Kenny: Like he’s the source of news about all these distilleries and stuff. And there’s over 40,000 people in his Facebook group about bourbon.

Kenny: Okay. Every now and then he slips in, Hey guys, like, you know, we just had an opening at our place. It’s near this distillery. If you’re planning to come for these dates because of this, you can come stay him.

Kenny: But he’s always booked. He makes a ton of money from it. Like he, he’s like, he’s like, it was the smartest thing idea I’ve ever had in my life. Like, ’cause he is like our bus. We are a hundred percent in short term rentals. We don’t do anything else. But I started this group, 40,000 people now is my audience.

Gil: Yeah.

Kenny: You know what I mean? And, and so he is really built this brand and it ties directly into his, his short term rental. But it’s a compliment. It’s not just go book my short term rental. It like compliments what, what the other things are. So.

Gil: Yeah. So, so, so what you’re saying there is kinda like summarizing a lot of folks, they, they focus a bit too much or if, if not all of their attention really around the stay itself. And what you’re saying there is like, people that have not heard about you before, they’re not necessarily interested in the stay.

Gil: What they would be interested is, is, is really around the experience and probably things to do in that market to, to really experience that. And that’s where you should be generating your content in. That’s where you should be drawing people into. And from what I heard, Facebook ads is possibly one way that you can start to draw people in.

Gil: It could be creating content around something, but really understanding what that deal flow is and really figuring out, okay, how do you get top of funnel there? How do you actually draw people into your ecosystem? How do you nurture them over time? And then at the very end, how do you provide them value?

Gil: And possibly if they needed someone to stay, that’s where they’re thinking about you, but not necessarily thinking about the discounts and stays all over the top of the funnel. That’s at the very end.

Kenny: That is a hundred percent correct. Yeah.

Gil: That’s awesome. That’s awesome. Yeah, I, I’m glad you, I’m glad you shared that and you went deep dive directly into that. Um. That’s, that’s pretty powerful. Uh, well, what else do you do kind of to really amplify that. There’s, there’s one thing that I have in mind. I’m interested in kind of hearing whether or not you, you do.

Gil: I, I feel like a lot of folks don’t run Facebook retargeting ads, and I think that that, that is actually a really powerful way, is if you actually have, not the cold leads, but if you have like, warm leads that are coming to your website, people that are intending to stay at your place. Actually using Facebook retargeting ads is a very economical way to really make sure that you’re top of mind for someone.

Gil: Because a lot of times they’re, they’re constantly all over the place or on social media, but then when you start seeing the same logo all over the place, when you’re starting to see things, you’re like, oh man, actually this place, this, this, this, this brand is everywhere. But no, it’s not. It’s just everywhere for you.

Kenny: Right. Yeah, no, I, I get that all the time. I’m looking for a sectional right now and there’s this stupid brand that keeps popping up, but they got bad reviews online and I’m like, I, I, you know, like, I like, part of me is like, kind of questioning the reviews now. They’re like, well, I just keep seeing it.

Kenny: You know, it’s like, it must be like, it must be legit. Like they’re business, like, you know, it’s like this thought and I’m like, no, no, no. But yeah, I, it, it makes sense. Um, I think though, I’m gonna say this, I would rather see someone, especially someone new,

Kenny: brand new, just create a direct booking site. I would rather see someone create a really, like start a good page, you know, a social media page.

Kenny: Start posting content on that page before they go down the ads route. ’cause you’re gonna lot, you’re gonna lose a lot of money doing, like, it’s, there’s a lot of trial and error and I think there’s more value in having a good page that people can follow first. ’cause it’s free, a hundred

Kenny: percent free. You just have to post the content. And, um, we can talk about like, actionable steps like right after the first thing I would post. But, um, the reality is like creating a page in a brand and starting a pre like a presence is, is gonna be more impactful than just trying to like, send traffic to a site via paying ads. I think you’re gonna get destroyed, in my opinion, um, in terms of like, the audience won’t be right.

Kenny: Like there, there’s just a lot of like, rookie mistakes that people make and it is very, it’s complicated to run ads sometimes, and the audience is, you know, if you start out brand new, you probably don’t even have an

Kenny: audience, so you’re gonna rely on Facebook to tell you yikes, like they’re just gonna take your money.

Kenny: Um, so I, I’m a, I’m a really big believer in keeping it very simple because simple can work,

Kenny: but you gotta start promoting the area, so,

Gil: I hear you on that one. And I think, like for listeners here, Facebook has a lot of data on everything that your business does or even that you do. And the more information that it knows about your specific audience, the better that it can run as. So even if for instance, kinda like to what you’re said there, if you don’t have a following there, Facebook really doesn’t know who’s interested in seeing the product that you may even want to run ads on.

Gil: So if you start to build up that following there, like I bet you yours, your specific following there are surrounded a lot about short-term rentals. And so Facebook knows if I’m gonna run this ad, even without configuration, it knows exactly who to target there much more than a fresh new account.

Kenny: Right, right

Gil: Oh, uh, you mentioned action steps after, after you do your first post.

Gil: What did, what did you mean by that? I.

Kenny: Okay. Here’s the number, the best lead bang I’ve ever created from my short term rentals. It’s a calendar. I wish I could share my screen. I’ll show it to you. It’s a, it’s a calendar, a seven day calendar for every month of the year, and each day is like something that you can do. So basically it’s like, what can you do in your area for a full week, for every month of the year? And it’s, it’s A-P-D-F-I made in Canva and it’s, so it’s 12 pages. Um, well, it’s a little more than that ’cause I have like festivals and other things going on too. But it’s literally like, just think of it simply like 12 pages. So every month a year, and on each page, Monday through Sunday, an activity or two multiple activities, a full day.

Kenny: So someone can literally go, okay, cool, I want to come in January, what can I do in January? On a Thursday? And boom, there’s an activity, there’s a link to this. Like, whatever it is, do this activity. So like, they changed throughout the year, obviously ’cause of seasonality or the, you know, like stuff’s open and closed during certain seasons and, um, but they’re, and it’s all different. So there’s something and, and you can literally go and create that and then go and share that and people will eat that up. It’s like, what are the, what’s the top thing you can do? Or like, what can you do on a, on a Wednesday in Watkins Glen, New York in February when it’s like 20 degrees outside,

Gil: Yeah,

Kenny: you know?

Kenny: Like, it, there’s, there’s, there’s an activity, a really fun activity, you know, so. Yeah.

Gil: I mean, that also goes full circle of being like a host as well too. Like you as a host, you’d know what are the hotspots and what people can do that allows you to actually, to serve your guests much more intimately than, than without that.

Kenny: yeah. Well, and, and it’s also like people, you’re, you’re probably sitting there like, who the heck would want to go to? I mean, I get this all, well, who wants to go to New York in, you know, the winter time? Um, you know, and when it’s like, you know, 10 degrees out or 20 degrees outside and there’s a ton of snow, you’re right.

Kenny: No one wants to do it when you, when you say it like that. Um, but when you share like, oh, well, did you know that, you know, we have a really cool, like. Ice skating rink that they do, and there’s like a lot of snow and sledding activities and they have these like, uh, like uh, Bob Sled things you can go down and, and just like really cool, like things going on in the area.

Kenny: It’s like, oh wow, like that, that actually sounds kind of fun, you know? And if you’re not that far away, you know, two to three hours, you’re like, well, maybe we can make a weekend trip out of that. And guess what? My weekends are always full even in this, even in the winter time, you know, on my property. And it’s because I’m positioning my property in a way that it’s an all year round property rather than just like only summer, you know? Um, and relying on what demand naturally sees. So it’s educating people and, and building a presence around that property of not just the property, but like the area. Like, Hey, there’s cool stuff to do here all year round. Here’s, here’s everything you need to know. Um, and you’ll get a follow from it and people will stay. Uh, and as you post more stuff, they’ll see it, you know? So,

Gil: Yeah, that, that’s an awesome tip. I, I, I love kind of like how that kind of threads back into your, your lead flow too, because you’re actually adding people to your top of your funnel that you can start to nurture over time as well too.

Kenny: Right. Yeah. And Right, exactly. And I always like something like that. They gotta gimme their email. It’s like, you’re gonna put in the work, like gimme your email address. And, but it’s worth it though. It’s a, it is a little bit of work. Um, it is a little, you know, a little bit of effort on your part, but the reward, once you make it, you made it right.

Kenny: And the reward is there at the end, um, to get the emails and people will gladly give their email addresses for that free information of, holy crap, I can do these things in these areas at any time of the year. It doesn’t have to be in July, you know, so,

Gil: Yeah. And are you dripping them every month and you’re sending out them in your new release? Or you say, okay, here’s the leak magnet. I’m gonna give you one packet that have all the different things to do in the year. Like how do you, how have you kind of made that, uh, workout effectively for you?

Kenny: so yeah. So I start with the lead magnet. So they fill out a form, they gimme their email address, and then I send it to them. And then I follow up and I’m like, Hey, uh, I started to get a little bit eccentric with it, where it’s like if you, because like you said earlier, guest avatar, right? And we have different guest avatars.

Kenny: We have people who are families, and we have people who are going on group trips to do the wineries. And so I’ll say like, Hey, I’ll ask ’em the email next. Like, Hey, do you, are you interested in learning more about wineries or more about like, the family stuff? And they’ll tell me. And then now I’ve segmented ’em, and then I have drip campaigns for each of those, you know, where it’s like purely just winery information or purely like just family events and things going on, and the communication.

Kenny: Like, I’m getting people like, hey, like, you know, are, they’re planning trips out like a year or two years in advance and they’re, we’re communicating via email, Hey, what do we, you know, like, how can we book your place? Like what, you know, and I’m telling ’em all the good tips, learning a lot about the wineries in the area.

Kenny: I don’t even drink, I don’t, I don’t know what wine tastes like. Well, you know, try to like, like, I, I don’t know what the wine, if it wines in the area is good or not. But like, you know, I, I can read reviews and go online and. And see stuff. And so, um, you know, and, and people are looking to me as like the source of information.

Kenny: They trust me, they’re gonna stay at my place,

Kenny: you know, so, um, yeah, it’s just being tackled about that. And so at first when I did it though, I didn’t segment it out and that’s fine. You don’t have to. Um, but I did have like, yeah, these are the top things going on in the area, sitting, you know, monthly updates.

Kenny: Uh, I try to send an email out at least once a month, if not every other, you know, like twice would be I, that’s the ideal situation. But, um, you know, just sitting and then sending reminders about, and then a discount every now and then about for the property. Uh, and then people get it. I mean, and they stay on because the free information I’m giving,

Kenny: so, Yeah. Yeah. I think it’s uh, Alex or Mo’s and is like hundred, hundred million leads actually. Yeah. Leads, it’s really around like when you’re trying to nurture someone, you wanna get them. Five times as much value before you give them even that first offer there, you really want to make sure that you’re nurturing them so that, that you see you as a trusted advisor rather than someone that’s always gonna be there to sell them something.

Kenny: Yes. Yes. Exactly. Exactly. So you want to be that like expert for the area, not I’m a STR host.

Gil: Yep. Absolutely. Kenny. it’s crazy cause I don’t even live in the area. It’s like

Kenny: there are locals who are probably like really upset that like, I’m like, they feel like I know more than them and I’m like, I don’t even like, you know, I go to my property every once in a while, but it’s like not often. So it’s just the power of the internet now, you know? So,

Kenny: yeah. Anyway.

Gil: all right, Kenny, we, uh, we usually end the show with three questions. First one, uh, what’s a book, a good book recommendation that you would have for me and the listeners here? I.

Kenny: Um, so the best, oh man, this is a tough one. Okay. The one that’s changed my business the most. Is definitely The Pumpkin Plan by Mike Mcit. I love that book. Um, it’s all about niching down, you know, and being unique and, um, how to grow a business without, um, you know, just like really focused on the, like the target audience.

Kenny: You know, I, when I read that book, I started focusing more on the consulting side and we just shot up from there in terms of our growth with my short term rental. I was like, what can I do to be slightly unique in the area and target the audience better? What would they like, what would they enjoy at my property?

Kenny: Not what I think would be cool for me and my family, but what would be cool for the people staying there and did that And boom, revenue jumped up So that my, um, that book was really influential, uh, amongst, uh, some other books. But that one was a, that was a big one. So the

Gil: I love it. All right. I love it. All right. Second question. What’s uh, one piece of mindset advice that you would give to someone that’s starting something completely new? I.

Kenny: Yeah, that’s a good one. I guess the first thing that comes to mind is there is, and you’ve probably gotten this advice before, but it’s really, it’s been, it’s easier said than done. And, and I almost say like, I’m not really a great example of this, but I, I understand it and I’ve used it and it’s helped me, but I learn to say no sometimes. You know, when you’re, and, and it goes back to, you know, what we were talking about earlier, Gail, with like families and priorities and things like when you’re starting something new, it’s e very easy to consume yourself with that. Um, it’s very easy to take on other projects too. At the same time. That might conflict with what you committed to already. You just can’t do it all. And the people who realize that they can’t do it all and like, fully understand that, not just, oh yeah, I can’t do everything, duh. But like you’re saying that, but you’re not doing that. You’re trying to do everything. Um, when you realize that you, you actually free up a lot of time and you’re the, the things that you are working on get better and perform better because you’re dedicating the appropriate amount of time to them, you’re not getting distracted with other things. Um, and for someone just starting out, you know, I think there’s a lot of cool investing techniques out there. You know, we hear sub two, we hear rental arbitrage. We hear co-hosting, property management, you know, obviously buying and acquiring. Pick one. Don’t, don’t distract yourself with all these different things ’cause you’re, you’re not gonna be, you know, you. You can’t be the, the jack of all traits isn’t successful. It’s the people who are really, really good at that one thing, and they just take it to the next level. So learn to say no. Pick your lane that you want to take, pick the path and then go like, execute, jump, dive, do something. Take action. Like if you’re gonna say no, that’s great, but don’t say no to everything.

Kenny: Say yes to something and then go. So,

Gil: Yeah. I think to kind of layer back to what you were saying, I think the, the other, I think when that starts to get really amplified is like when you start to surround your people, that will help you kind of point in the right direction. So when you do say, when you do say yes to something, you have a lot of conviction on how to proceed forward with things.

Kenny: Right?

Gil: Yeah.

Kenny: Yeah. Yeah.

Gil: Awesome. All right, Kenny, last question. We talked a lot about direct bookings. We talked about your, your lead funnel. What’s one piece of tactical takeaway that you would give to someone that’s either starting their direct booking engine for the first time or trying to amplify it?

Kenny: Go, gotta create a social media page like asap. It’s free, easiest way to generate leads. And then I would say go. And so create a social media page. Start posting about the area on your social media page.

Kenny: So pictures, not at a bunch of properties.

Kenny: not a bunch of properties. Who cares? It’s not Oh, cool. Like, you know, uh, Tina’s, you know, beach getaway name. That’s what we’re talking about. We’re talking about like the market area. And it is, you obviously can’t just, you know, say the market, uh, by itself. I created something unique, but like my buddies, the, the Bourbon Sherpa, you know, um, my, my page and it was branded off ’cause it was a business before, it was actually a bed and breakfast, um, for Watkins Glen.

Kenny: It’s called Lake Valley Legends. And it’s all about the legends of the lake, that it’s Cynical Lake and Watkins Glen. But anyway, like it’s, it’s just like, like it’s got its own brand that like people recognize in the area. Um, and so like, but it’s not about the property,

Kenny: you know? It is, but it’s not like, it, it’s like this subtle, like we know what we’re trying to do, but like, and, and so like create that at, you know, like get that social media going and make a few posts about the area, what’s going on in the area.

Kenny: Like start just talking about it and people will just naturally follow you and, and boom, now you start having leads for your direct booking site. You know, like it’s, it’s that simple. Um, but it takes consistency though. So that’s what I would start with.

Gil: Awesome. Awesome. All right, Kenny. Um. For folks that wanna either work with you or get to know you a bit more, where can they follow you? Where can they learn more about you? If there’s any interesting projects that you’re working on or specific clients that you want to engage with, where can they engage with you?

Kenny: Yes. So, um, I focus on helping people find properties short term rentals. So if you’re interested, if you’re listening to this and you’re like, Hey, I need help finding a short term rental that’s gonna make me money, that’s where I, I am going to be able to help you. So if you want to go to my website, just STR insights, so STR insights.com, um, you can follow me on social media, you can message me there at Kenny Bedwell. Um, you can get a chuckle. Have a chuckle, and also learn some stuff too. It’s, it’s, uh, laughter and education in one. So, uh, and you can message me on there and we can chat as well. Um, I’m gonna be, I, you know, it’s really funny, Gil, people tell, ask me all the time because I share the lead magnet stuff with people and people ask me all the time to, can I help them build that out? Um, can I do this, this, and this form? The answer’s no. I don’t do that. I can do it, but I don’t have time to do it. It goes back to the learning to say no thing. Um, and I want you to do it, and I want people to figure out, I will give you the templates for free because I literally do not like, have the time to set aside to help people do that and get paid for it. Um, but I do set aside the time to help people find properties. So if you’re interested in that, please reach out to me and I can help, you’ll do that. If not, I can send you the templates and the info for free. But that, that’s as far as it goes. So,

Gil: I love that. I love that saying yes and saying no at the same time.

Kenny: exactly. Exactly. I’m just, I know it, I know if someone’s gonna reach out and ask, and so it just, it happens every time. So spoil, uh, I don’t want to, like, I’m gonna let everyone down right now in sooner later.

Gil: Yeah. Yeah. yeah. Kenny, I appreciate you being on the show. It was, uh, it was actually really good to kind of see how you’ve progressed through years and how you juggle all the different facets of your life and actually give us a lot of good information where we can start to take away and think about really how do you market your, your properties and the market themselves more effectively than just talking about your properties alone.

Kenny: Yeah. I appreciate it. Thank you for having me on. That was really good. Good conversation.

Gil: All right. And I, I’m sure I’ll see you at some of the conferences or if not a, a few of the conferences later this year too.

Kenny: Yeah, absolutely. Absolutely. So I look forward to

Gil: Oh, all right. Talk to you later. Bye.

Kenny: you. Bye.