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We’re excited to sit and chat with Jonathan, TopKey Co-Founder, and CEO, about his journey from growing up in a vacation rental town to building a tech-enabled financial operating platform for lodging and short-term rental operators.

Episode Highlights

  • We discuss the growth and development of vacation rental destinations over the past decade, particularly the Gulf Coast of Florida.
  • Jonathan explains how TopKey initially aimed to create a marketplace connecting property managers and homeowners and hit on the shift in direction after joining Y Combinator, which led to a deeper focus on the vacation rental industry.
  • TopKey’s recent $5.2 million raise and how different rounds are today compared to just a couple of years ago.
  • The conversation explores how Jonathan’s background led to the creation of TopKey, a financial operating platform for property managers and hotels.
  • TopKey’s primary focus is on helping operators streamline financial processes, such as expense tracking, account management, and owner transactions.
  • Jonathan explains how TopKey issues Visa-issued credit cards tied to individual units, enabling real-time transaction tracking.
  • TopKey’s platform integrates with major accounting software and PMS systems, simplifying the monthly close process for bookkeepers and property managers.

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Show Transcript

[00:00:00] **John:** Good morning, mate. How are you?

[00:00:02] **Mateo:** Good morning, John. Fantastic, brother. As usual.

[00:00:05] **John:** That’s good. That’s good. Tech exec series, episode 107. We have a great guest. We’ve got lots of amazing things to talk about. It’s been busy. This transition to doing this on our own and figuring all this out has been exciting. For those that don’t know who didn’t listen to last week’s episode, Mateo and I founded No BS Productions. We are legit now, and we’re doing this on our own, so we’re excited. Long story short, we’re excited and we’re changing some stuff up a little bit. But without further ado,

[00:00:34] **Mateo:** Yeah, we got a great guest.

[00:00:36] **John:** Joining us today is John Sukhia. I hope I didn’t murder that, even though he just told me like a minute ago what it was, from TopKey. How are you, man?

[00:00:45] **Jonathan:** Good, man. Thank you guys for having me. I’m really excited to be here.

[00:00:48] **John:** We’re excited for you to join us as well. TopKey has been in the news with a recent raise. So we definitely wanna go ahead and talk about that. But I wanna talk about when I first met you in Missouri at Spring Forum. And I was fresh into, like, two weeks or something like that at Direct. I hadn’t been there that long. Maybe a month or so. I had just come over. And then you guys were—I remember building your booth.

[00:01:15] **Jonathan:** I don’t know how you’ve become the guy that built the booth, but—

[00:01:18] **John:** No, I didn’t build a booth. I remember you—

[00:01:21] **Jonathan:** Oh,

[00:01:21] **John:** but,

[00:01:21] **Jonathan:** you helping, assisting in—

[00:01:23] **John:** You’re the TaskRabbit.

[00:01:24] **Jonathan:** Yeah.

[00:01:25] **John:** And it was—we, that’s how we met though. You were, you had yet to build your booth.

[00:01:30] **Jonathan:** Right, we had a we had a TaskRabbit that I hired to help me build this thing because I’d never built it before. And apparently the organization that sponsored the event required the TaskRabbits to have insurance, and they wanted you to pay two grand to have their guys do it. And I was like, and this guy was like a complete pro. And he showed up and he had three insurance levels. And I was like, you’re amazing, man. ‘Cause I was gonna—I was gonna be paying like two grand out of pocket to have the labor, or I would’ve had to do it. But yeah, it was funny.

[00:02:00] **John:** VRMA doesn’t mess around. Any of those organizations don’t mess around either, because even like I had to go rent a circular table because ours didn’t come together, and it was like, 600 bucks or something ridiculous like

[00:02:11] **Jonathan:** It’s unreal. Yeah. You’re just hemorrhaging money when you go to those things if you’re not careful. But yeah.

[00:02:16] **Mateo:** Shady though. Like I feel like they’re taking, they take advantage of you being in peril, right? Like you really want this table $600, How?

[00:02:24] **Jonathan:** You need that waste basket like,

[00:02:27] **Mateo:** Like you need a power strip.

[00:02:29] **Jonathan:** Yeah, we can get you in a really good wifi situation. About $300 a day, but it’s.

[00:02:35] **John:** So that’s where we met. It was an interesting show because there was nobody there. But because of that. I get to know you and your team and learn a little bit about TopKey. And it’s been exciting to see you start popping up and showing up in the news and, hey, now you just raised 5.2 million. So who’s this TopKey? This is one of those startup stories that outta nowhere and we know better that you’ve been working your ass off for years behind the scenes.

[00:03:02] **Mateo:** We gotta start at the beginning, man. ‘Cause he’s got an amazing hospitality journey that actually speaks to my heart. Finance background, hospitality. One of the things we really do here is we want to get the full view of who you are, right? And in this space. And like, where’d you grow up? How’d you get here? You didn’t just wake up one day and say, you know what? I’m gonna be in this short-term rental business, and I’m gonna bring my finance experience and make the lives of property managers easier through technology. Tell us your story, how’d you get here? And how’d you get into hospitality?

[00:03:34] **Jonathan:** Yeah, no guys. A broad question, so I’ll try to make it as succinct as possible. My background started in—I’m from Florida, from Tallahassee, Florida originally. Went to Florida State for undergrad, and then I was an accounting major in undergrad. Ended up shortly after graduating basically doing a bunch of my own work to get into grad school. And I had a couple buddies from college who had gone to do some really interesting things in finance, and I knew I was inclined toward that arena, but I didn’t know how to make that shift from accounting to doing something a little bit more intense in finance.

I ended up taking like a six-months I studied basically every night for the GMAT. And I ended up going to Duke for business school. And then at Duke, I did a, like an unpaid internship, went to New York, and then I ended up getting an investment banking role. I did like a one-year master’s program at Fuqua. So it was designed for folks coming from undergrad versus a full two-year MBA, but effectively the same exact coursework. And it’s called a master of management. So it was a very natural place for me. ‘Cause I had a business undergrad degree, but it was like, really gave me a different perspective on the world being it’s such a great institution and all that.

So I ended up doing a getting a job at Wells Fargo Securities on the investment banking desk. And I was in between Charlotte and New York for about two years to Charlotte where Wells Fargo Securities is based. Classic investment banking, 60 to 80 hours a week, just grinding for two years. Just a really great place to develop a strong analytical skill set. And also just a professional, I think like a base of skills that just serve you well wherever you end up.

 After two years, I was covering industrials, so I was covering like paper packaging, forest products, timber REITs, and my a, a guy I worked with on the desk at Wells had left to join Starwood Hotels up in New York.

And I had wanted to go to New York had lived there for a few months and New York’s a great city to be, when you’re young and single. And I was like, I wanna go back to New York. So my buddy got me an interview and ultimately, I was able to secure a role in the corp dev team at Starwood. It was a really interesting position because that team basically helps Starwood or helped Starwood at the time buy and sell assets. The Starwood, there’s two kind of Starwoods that are well-known in our industry. They’re Starwood hotels and then the Starwood Capital Group, which both were founded by Barry Stern and I was at Starwood Hotels.

So the M&A team there. And I was just really fortunate to be there at a very good time because we were active. I was focused on like doing a lot of their capital markets work. So building their commercial paper program and bond, they had some specific bond deals that I worked on. But then separately really digging in on the hospitality space. ‘Cause we were at the time selling our timeshare business, which was Ana and then it ultimately got sold to a company called Interval Leisure. So Starwood and I was just the junior and then mid-level director on that team that managed that process. So worked with a lot of the folks on that team. Fast forwarding separately worked on Starwood and Marriott ended up merging, worked on that as well. Just being in that team. And so it was just really fortunate to see at the time, one of the largest acquisitions in the hotel, I think still may be the largest in the hospitality space, Starwood getting bought by Marriott. Fast forwarding I ended up having the opportunity just to. Just to take a step back and either join Marriott or decide to do something different. And so I left to go to California and I moved to a company called Hotel Tonight. I took a role in partnership, so very different position, but I knew that was something I was really interested in.

[00:06:50] **John:** Hotels tonight was that pre-being acquired by Airbnb?

[00:06:53] **Jonathan:** Yeah, pre-being acquired by Airbnb. So this was 2017 when I joined and ended up, managing a team of folks who oversaw the supply on the hotel management company side. So worked with a lot of the leading hotel management companies. Hotel tonight. Last-minute booking engine ended up expanding to a full suite of booking calendar, and we were mostly focused on like inventory in mainly Western Europe and bigger cities in the US. So Miami, LA, San Francisco, New York of course.

So managed a team across several different markets in that area. We got acquired by Airbnb which was an awesome experience to go through. It was deja vu going through another acquisition. Yeah, it was a, again I’ve just always felt like been blessed to be in good positions and worked with awesome people. But anyway, when I joined Airbnb the acquisition as part of that transition was mostly around Airbnb buying Hotel Tonight for a couple reasons. One of which was to build out the hotel’s inventory platform on Airbnb. I ended up just had a couple really cool roles there. Did a lot of interesting things in addition to just managing that team. But effectively middle manager at Airbnb. I was looking at the future there, a lot of my time there was like, man, I just, I wanna start something.

I’m excited about entrepreneurship. And spent the better part of. I call it a year just thinking about ideas. I had a friend who was an engineer at Airbnb who I was talking to pretty regularly. And fast forward, we decided to leave to start TopKey. And initially, we were building something very different. We started a marketplace to connect property managers and homeowners. And so that was the initial big idea that we had. I left Airbnb in the fall of 2020 to start that. And then suffice it to say, basically we went through and got into Y Combinator, which is a startup accelerator based in Silicon Valley that had previously backed like Airbnb, Stripe, Instacart, a bunch of great startups. And then over the summer of that year, 2021 now just decided that we really, I. Didn’t see the viability of that type of business as a venture-backed company. And we hadn’t raised a lot of money. So it was a really good spot to be in, frankly, as an entrepreneur. ‘Cause we had just raised a tiny little amount of money. I could pay myself a bit of a salary, but I didn’t have the obligations or the pressure to go out and scale something that wasn’t gonna work. Which is a real challenge if you get into that position. And that sparked the journey. Yeah.

[00:09:03] **John:** Investors are excited to get behind something that’s actually gonna go ahead and make them money too. Not just, so before you go too far down that path,

[00:09:11] **Mateo:** That’s what Rented was, pre, pre-rented Vacation Rental Futures. Did that. If you, and it’s interesting, like I don’t know if you came across that

[00:09:19] **Jonathan:** I did. I talked to a couple of them. Michael Golden. I talked to Andrew, I talked to a few others on that team, just to get like insights around it. We had, we dug in pretty deep. I know we were talking before the, before we started recording, but at the time I was living in San Francisco decided to in 2020 and during Covid basically moved we, we bought a car and we lived in different vacation rental towns.

This was before I left Airbnb and then, we were living in like Boise and Bozeman and Austin, Texas. It was just like figured, Hey, when else can we do this? My wife was a consultant. I had a lot of bandwidth to do stuff, remote Airbnb, of course. Ended up buying a house down in Santa Rosa Beach, so in 30A. And we just thought what better market, one of the highest concentrated markets of vacation rental managers and we were fully remote at Y Combinator. In that time, that was a place for me to really just focus on this without a lot of distractions. There was no startup parties or anything of that nature. There was no talking to VCs, it was just, I’m in a vacation rental market meeting really cool people, building some amazing company that, in my world, people have not a lot of context for like that. But the tech world doesn’t really spend a lot of time with that cohort. And obviously we do, and our all of us do. But it’s It’s a bit still underserved, I would argue so

[00:11:25] **Jonathan:** That Grayton Beer Pub there, that’s pretty fantastic.

[00:11:28] **Jonathan:** Yeah. We lived right around the corner from there, or a little bit down the street. But yeah, it’s become like a—I so I grew up going there as a kid, right? And it was

just destined, a sleepy town. There were still people that would go there, but now it’s, yeah, no way.

Like you, you were down there, right? Not long ago, John. It’s like

[00:11:43] **John:** 

[00:11:44] **Mateo:** Yeah.

[00:11:45] **Jonathan:** guys? Yeah, it’s just, it’s exploded down there. And I love that area. Have a ton of friends down there and. It’s just such a great place. This is like still un to me, it’s still a lot less developed, of course, than like South Florida or anything

[00:11:58] **Mateo:** Oh,

[00:11:58] **Jonathan:** that area, so you still have a lot more room to

[00:12:01] **Mateo:** And you’ve seen the development over the past 10 years, right? Like it’s developed a lot, here (in) Atlanta, so many people still don’t know about 30A, so we’re like

[00:12:09] **Jonathan:** Yeah.

[00:12:09] **Mateo:** the Gulf Coast of Florida and then you’re like

[00:12:13] **Jonathan:** guys from Chicago, but I noticed when we were there, it was like

[00:12:16] **Mateo:** snowbirds,

[00:12:17] **Jonathan:** Midwest folks, Canada. Growing up, it was like, all right, you’re in Birmingham, Atlanta, maybe New Orleans. Like now it’s just the floodgates have opened. Hey, like that’s, It’s great for that area for many respects, but yeah.

[00:12:29] **John:** Now you’ve moved to Nashville.

[00:12:30] **Jonathan:** Yeah. We recently decided to move to Nashville and the reason was not for anything negative about that area. We decided as a company we wanted to be in person. And so had spent a lot of time thinking about where we wanted to be and then just. Personally, my wife she’s from Sweden, so we go there, she goes there a lot in particular.

And we just, we were struggling to be at a place where, we had to take three flights to get to Sweden. And so anyway, we had both had family up in Nashville, that were from that part of the country. And we’d spent a bunch of time here and just really liked it and thought it’d be a great place to recruit really good tech talent. So that, that’s how we ended up here. And we moved here about a month and a half ago. So we’re still pretty new.

[00:13:10] **Mateo:** I think you have an interesting perspective and what I want to hear how you, how we get to TopKey

[00:13:16] **Jonathan:** Sure.

**[00:13:17] Mateo:** Especially with your experience where you were going, where you ended up, you grew up in vacation rental towns, like you said, you grew up in Destin. So you have a dual perspective of where the industry was and now how the industry is transforming right now at the tech level, and maturing through a next generation of people coming into this industry that are tech-enabled, that are a different type of traveler with a different type of viewpoint and worldview. So, how did your experience turn into TopKey and like where you are today?

**[00:13:51] Jonathan:** The thing with, for me at least, is just seeing our industry. I growing up seems so cliche because it’s not. It’s a very established sector of the economy in some respects. But then you have so many newer folks and so many newer both on the demand and the supply side getting into the market, right? Of course, on the demand side, Airbnb was at the forefront of this and just bringing in a sector to the zeitgeist in a way that there’s just been a huge influx, of course, as you guys are aware. But then separately what I’ve seen is there’s been a real shift in terms of the type of folks who are entering the market. We’ve seen it at TopKey. We’ve also seen it just certainly getting to know the sector. I was seeing it at Airbnb where we worked with a lot of these companies and I was relatively joining from Hotel Tonight. We were just jumping into a company that was already way farther along. It was like walking into a roaring river. This thing was going on. And you could see that there was no stopping it. But from a tech perspective, what’s been really interesting is that I think there’s a lot of folks who recognize the power and then recognize all of the tools that are out there to basically streamline your operations and do things more efficiently. And I think tech admittedly can get a bad rap for certain aspects of how people perceive technology and of course the leverage that some tech companies can exert on smaller vendors. But as a strategic operator, I think the thing that I find really exciting, and I also see this with a lot of our customers, is there’s a whole host of people that recognize where they should offload work that they recognize they’re not gonna do the best, and then where they should try to take on more work that’s to the best and highest use of their skill. And it’s really hard to build a vacation rental management company, build a hotel, build any sort of hospitality, furnished apartment company, and then also try to manage and manually oversee all of the aspects of your booking strategy, channel management, your financial operations. So those things just become very almost zero-sum, like you can only do so much so well in my opinion. So that’s to me the thing that really struck me about the last, I’ll call it a year and a half, building this version of our business.

**[00:16:01] John:** The interesting thing, John, is that these property managers, whether whatever size they are, and you, the size that you’re going after are a little more established, a little bit larger than a little more step in structure and how they’re built. But you’re still only as you’re only a pro at what you’re a pro at. And then there’s a certain tech and there’s certain things that you have to outsource. And what are those, whatever those things are, let’s and for. What you guys do is you come in and you help with the finances and you help with expenses. Let’s go ahead and why don’t you give us your thirty-second elevator pitch. For those that are listening, that what the heck is TopKey, right? They’ve been listening for 20 minutes, now, whatever, and they still don’t know what TopKey is. Why don’t you go ahead and let our audience know what TopKey is and then we can go ahead and talk a little bit more.

**[00:16:50] Jonathan:** Sure. So we are building a financial operating platform for vacation rental operators and hotels. So what we do is we offer property managers the ability to create both FDIC-insured checking accounts as well as secondary trust accounts that they can create with for owners. We have Visa-issued credit cards that we issue to our customers for them to basically use in the field as well as online that allow them via text integrations to track every transaction back to individual units. To ultimately close their books faster. And then we have built a number of direct accounting and PMS integrations, and we’re in the midst of building our PMS integrations to help streamline that flow of information and ultimately to save mainly bookkeepers, owners, and financial operators time during the monthly close process, which is arguably one of the most cumbersome and challenging aspects of the day-to-day operations folks are constantly flagging. So yeah, that’s in a nutshell what we do. And there have a lot of other things that are in the pipeline or on the product already. But that’s a synopsis.

**[00:17:54] John:** So I love this. So let’s dive a little bit deeper into that. So you issue Visa credit cards that can go, or they’re debit cards of sort. Are credit cards that, but any sort of transaction that happens on the card, those cards are tied to units or are they tied to individuals, so this is my question. I am Joe, somebody I work on the hospitality team, maintenance guy at a vacation rental company.

**[00:18:16] Jonathan:** Yeah, a company signs up for TopKey. We allow the owners of the business, whoever is an admin on the team to issue cards both physical and virtual to their team. So you can create unlimited virtual cards and individual employee cards just the same way you would create with an Amex or Capital One or what have you, those cards in the field at authorization. Joe, the maintenance guy at Beach Sun and Fun in the Sun Management company in Amelia Beach, Georgia. I’m just making it up. The company, let’s say on average, is managing 70 units. On average, they’re gonna be spending anywhere between 70 and a hundred thousand dollars a month on transactions that are going back to that, those units and meaning those transactions need to be reimbursed by those owners typically. And, every company has different structures. Some companies manage inventory that they own. Some companies manage inventory that is owned via an investment entity. But generally, everyone’s faced with the same challenge, which is, I need to allocate all these transactions back to those properties and do that every month in order to close my books and make sure that I can get clean reporting on those units. So what the team is basically doing is in the field, what we’ve built is a tool that whenever a card is swiped, we send a text directly to that cardholder. So Joe, the maintenance person in this case, gets a link to a web form that he can open up on his phone anywhere and he, Google, Android iOS, and he can select and upload a receipt and upload a memo. And then we have all the properties preloaded.

**[00:20:01] John:** Oh nice. So you can just go ahead and tag it

**[00:20:02] Jonathan:** We can easily tag it to a property. And then he also, we also have these categories that we’ve predefined. So effectively what they’re doing is it’s build to own or build a guest, build a corporate or assign inventory. And you can think of that as like the action that needs to be taken on that transaction for the bookkeeper or for whoever is dealing with the close of the books.

**[00:20:22] John:** It’s like QuickBooks, tied directly to that credit card, which in turn plugs it right

**[00:20:28] Jonathan:** You got it. Yeah. You hit basically do that. Takes two seconds to do this. We also then have direct integrations to all the major accounting software. So for instance, with QuickBooks, if you’re using class, for instance, to code your properties and QuickBooks, we have the ability for you to map one-to-one to the class category, and then we’ll push that transaction over. And we have auto rules to set to assign the general ledger category in QuickBooks. So for instance, it’s expenses maybe it’s maintenance expenses. We can auto-assign that, and then the transactions are staged. The bookkeeper can go in, they can filter down to very specific, they can filter for let me see all their transactions from the last month that are assigned to a property but don’t have a receipt. This is the type of thing that bookkeepers are thinking about every day. I have 18 transactions. Now what do they do today? And again, it’s what they do today is they have a spreadsheet, maybe it’s a Google spreadsheet, maybe it’s some sort of like hack together, Expensify, maybe they use Divvy or something like this. Then they’re going and like texting someone on their team and going, Hey, can you send me the maintenance person who’s probably got a million things on his plate? Can you send me a receipt from three weeks ago? Do you remember where this, what property was this for? It’s just a messy kind of manual process. And then they’re going in and manually inputting this stuff into either QuickBooks or often in QuickBooks, and then separately in their PMS, if they’re producing owner statements out of PMS. That’s the last piece of the equation. Certain managers do it in the PMS, others are doing it manually. So there’s just a really cumbersome process that

**[00:21:51] John:** It’s messy.

**[00:21:54] Jonathan:** Then you lose money if you’re not careful. And certainly what we’ve seen is a lot of managers are just leaking money because not every transaction, as everyone knows who runs a business, are you sure that every dollar that you’re making on behalf of your owners? This isn’t, for instance, with TopKey, we have a team, we have expenses. We don’t have to get reimbursed for every dollar that we spend. I need to make sure that the dollars are accounted and assigned to the right general electric category. But for managers, our industry doesn’t run at like software margin. So these are real costs that like at the bottom line can become a real drain on the business if you’re not careful. So that’s the initial product. And then we have a really cool bill pay product that we’ve just released to basically allow you to pay vendors, use AI to populate invoice line items, assign them to properties, and effectively in the same way, you can track a credit card purchase, you can track a bill pay purchase back to a property, sync it to the accounting software. So we have the ability to basically pay all kinds of transactions out of the platform. And then these kind of very thoughtful ways to connect that information to the right systems that you need. A mouthful, but

**[00:22:59] John:** It’s necessary. It’s one way to get the end result that everyone’s trying to look for. They’re, you’re either going to use your product, which sounds fantastic, or you’re gonna go through it the way you’re doing it and hope that most are doing it probably today is through their PMS and hoping that they have a solid solution that is in place. And, it’s those, you’re, you hit the nail on the head with the margins thing, right? The margins are so tight, and they’re getting tighter and tighter as days go on. So to be able to allocate every one of these expenses correctly and get reimbursed for them the way they should be and not be losing a little bit, pennies on the dollar is, in tech margins isn’t necessarily. The same as it is for PMS, so it makes a ton of sense.

**[00:23:42] Mateo:** And it matters to the smaller companies, right? Like you said, that impact is real and they can’t afford to just let those things slip through the cracks. It’s interesting though. When you see the adoption of this, do you find that you’re still having to convince people the value of. These types of, ’cause, in our industry, and I think we’ve talked about it a little bit, this changing of the mindset, this kind of new approach to where you came from a tech optional background to a tech essential and a tech-enabled fu necessary, right? These are the things that are the differentiators that could keep people in business versus not. Understanding that. Are you seeing that in the adoption of what you’re doing and an adoption of your product? Are you still getting a lot of resistance for people who are a little overwhelmed or understand?

**[00:24:33] Jonathan:** We took,  I think a genuinely like thoughtful approach to beta testing this for a better part of a year. I think in a lot of respects, financial products in general just require a lot higher bar to release versus just like even a SaaS products and in general, just because of the nature of the compliance we’re partnering with an FDIC-insured bank. We have Visa has their own massive I would say in initiation process that you gotta go through just to get like approved and all this. So we spent about a year building the product. I spent a large part of that period basically going and signing up companies that I got connected with all, mostly through my network, people in the industry and really vetting companies almost as much as they were vetting us. ‘Cause I was like, I wanna make sure I’m working with really thoughtful, sharp managers who also recognize we’re in a beta and I wanna be able to work with them you need that because at the end of the day, like I’m not day-to-day managing a vacation rental company. Our customers are. And so having that for. A good while was really valuable ’cause it, a, it gave us a ton of really unique insights about other problems and pain points. B it really allowed us to work out kinks in the product.

**[00:26:41] John:** This is your advisory board. Yeah, it’s essentially helping you with your roadmap. They’re helping you make these decisions. This is working, this isn’t working. Oh, why didn’t we think of this? And it’s invaluable. And these beta users that you got the balls to go talk to and figure out work with. They’re the reason, and you’re smarts and your team smarts. They’re not the only reason, but having that relationship with them is the reason that you’ve been able to go ahead and you just raised $5.2 million, which I wanna make sure that we talk about like how relatively quickly come to the table with some money to do something pretty substantial here.

**[00:27:22] Jonathan:** Yeah, I mean we, we were super grateful for our investors. It’s like really awesome. I think folks we’ve gotten on the, around the table Felicis led the round there. They were the initial investors in Shopify and Canva and a bunch of like other startups. And then Andreesen Horowitz, led our pre-seed about a year ago and then as well, participated in this round. What we’ve seen is that this raise doesn’t change like much in terms of like our approach. It’s just I can basically roadmap more products and like we can go out and we, I, one thing about the venture capital landscape, which, I think a lot of people are learning and I’m certainly learning as well, is like the capital raises that happened in the past are way are going the way the dodo bird, like you’re not gonna have huge rounds and the kind of idea back in, even 2021 was like, Hey, you raise a round and then just show a little bit of inkling of revenue growth and is assuming you have some positive momentum, you can probably raise another round. It’s a very different landscape. So we’ve not gone and hired a bunch of people and we’re not like ramping up a huge team to build out build the market. We’re thinking about this as, and in the way you think about it’s, Hey, if this was the last money I ever raised, what would we do with this money and how would we be responsible? It’s still like a learning process. But Mateo, I wanna mention, go back to one of your questions, you had asked about with respect to how do you think about pushback or like maybe… Are there concerns? What we’ve seen as we talked to a lot of managers is a, there’s certainly a cohort of people that are like, I’m not ready to make this shift yet, because this seems like a lot of work. That’s one thing we hear. And I think a lot of people are used to the kind of the major PMS transitions that occur and how much work goes into that. And so what we’ve tried to flag and what we’ve shown, I think we’re doing more of this with like demos and Marketing’s not my forte. That’s the area that I’ve struggled with the most in terms of it’s just not something that comes natively to me. I don’t have those chops. And so we’ve tried to really show people, hey, it’s two onboarding calls. It takes you 30 minutes, we send you cards. There’s not a lot of complexity to this. You, it’s like opening a bank account, but and if you don’t want to use the bank accounts, for instance, you can use the credit cards. We offer 1.5% cash back on every purchase. We’re giving you, basically a really competitive. Right there that beats any mileage program we can get you set up really quickly. So that’s been one. And then the other I would say is there’s a certain subset of the market that I do think is a little bit reticent just because they’re cut from a different cloth and it’s Hey, this is, I wanna see this product. And it’s just like adoption curves. You can start to tell, but what’s been cool is we’re starting to see folks even in that category, I would classify them as starting to say, wait a minute, we can do this, we can test this. And that’s exciting to me because it shows me that there’s all you’re thinking about as a founder is do we have product market fit? That’s really the name of the game. And, until this is proven out, it’s not like this business I can’t say that until we’ve proven that. Thesis out through adoption, and so we’re starting to get to the point where I’m feeling confident saying that we have certainly a really good line of sight into that with the existing products. And we haven’t had any companies churn since we launched. We’ve never had a we just continue to like, grow the number of companies and also grow the user base in terms of activity. So like folks, Adoption curve for something like Taki is initially maybe they put a little bit of spend on their cards and then they go, wait a minute. Let me really start like ramping that up. As I see this is working, my team’s saving time. I’m, I got a text the other day from a manager saying, Hey, I, we caught like $3,000 last week in expenses that we would’ve just completely missed. And this is a big company. They had 150 plus units, and so he said, yeah, every day. They’re, he is, I think they have, they’re onboarding new employees pretty regularly, and there’s just stuff that gets dropped in the shuffle. So anyway, all that to say I think we’re seeing more and more adoption, but pushback remains. It’s just something you’re constantly thinking through and how do you mitigate those questions and stuff.

**[00:31:02] Mateo:** I think you hit the nail on the head by picking up the phone and not doing what you think is good for managers. But listening and doing a listening tour, you’re a hundred percent the beneficiary of anything that you get from that feedback and It’s something that I’m sure that you’re gonna want to do, but seeing, your idea and your leadership. Kind of style. I see that going. It’s interesting though, like I’m a partnership guy, so to me it seems like these are a lot of partnerships and it seems like that’s a lot of the way that you operate too. Talk to me a bit about like how that’s defined your vision for the culture of the business and as you’re growing, are there more partnerships that you have to offer and like, when I’m looking at the model I see a kind of limitless platform for what you’re doing around that space.

**[00:31:46] Jonathan:** Yeah. I look at it from the concept of a partnering with our customers, and obviously there’s like a, that, that word gets used a lot I think a little bit, with respect to customers. It’s are you really partnering with them, or, so I think we’re trying to truly do that and just show that, hey, we’re. We wanna learn from you. And also if you like the product, you’re gonna use it. And we’re gonna learn a lot more from that process. So just being very like open to that design partner concept and having folks on the board that are not just design partners, like for spec for the whole platform, but it’s like, Hey, will you be a design partner for this integration? Would you be a design partner for this specific feature? And I really will like press upon you. The only thing I’m gonna ask is I’m gonna do a call with you. We do We’ve done maybe seven or eight now, companies that we do like a standing either weekly or biweekly call with typically their bookkeeper or their accounting person. And it’s really intended to be a open-ended forum to just talk about what are your issues, what’s going on? Any flags on the product that we can fix or things that maybe you want to improve. So a lot of our insights, for instance, we had a company say to us, Hey, I’m going back and forth with managers with my team on pulling receipts down. So we built a little function where if you can open a transaction, you can hit a button and it’ll send a text for that specific transaction. And it’s just like a little thing, but it makes such a difference. They don’t wanna be the guy that has to go back and like bug their owner or bug their maintenance person or whomever. And then on the, so that’s one piece. And then the other piece to your question is just on like other companies and what I’ve seen is, a, we have a lot of interesting inroads there because of our card product I, I can’t count how many people have reached out about Hey, we should do a partnership where, we get we’ll give you companies like 2% cash back. We all do discounts and mar we’re all in each other’s marketplaces, right? Like, why not make the discount just a cashback component and if we, just something like that. So there’s unique things there. And then trying to, I’ve spent a ton of time with a lot of other founders that I’ve gotten to know in our sector. And I found this area of. Our business to be very generous people are really willing to open up and help if there’s any lessons for this podcast, as much as I could think of, it’s just just ask people to help and be generous to like, turn it around and give it back. But like people really do go outta their way. It’s amazing how many people have come outta their way to make an intro or make a call that I wouldn’t have. Expected them to. So that’s, to me, been the coolest part about this. And I know that sounds hokey, but it honestly is, to me, that’s just,

**[00:34:00] Mateo:** It’s our space. It really It’s not finance. You would not see this on Wall Street. Like you would not see this at banks like in No it’s very different. But it’s very honest and authentic. One of the Things I love about the space. Honestly, a hundred percent.

**[00:34:14] Jonathan:** yeah. For sure.

**[00:34:16] John:** We’ve come close to the end here, but what’s new for TopKey and what’s new for you? Where are you going? And what’s on the horizon?

**[00:34:23] Jonathan:** The biggest focus for us right now is just continuing to refine the existing product. So building out more integrations, building out a lot more functionality for folks who are using the card product. We have some really interesting things around project based spending. We built a feature to allow you to attach a card to a property. So not required here. So the idea is not to create 150 cards if you have a hundred, but if you’re doing onboarding, which a lot of companies that are signing up to us are, they’re growing, they’re scaling, they’re, you hit these inflection points where you need more support and the systems that you’re using break. What we’ve done is you can very easily create a card, have it attached to a property, and then the follow up to this is like actually be able to download an output that shows you all the different spin. It’s not tied to a specific date, but it’s tied to a project. And that way you could send that to your owners and here’s the onboarding spin for, fun in the sun. 22. And here’s the onboarding spin that we incurred. We bought all this furniture. We spent money on, upfront.

**[00:35:19] John:** Love that. And is that something that you could build a, a temporary thing, right? Hey we’re gonna go ahead and turn this on for this onboarding time. You’re gonna see everything. And just the data and analytics behind that alone is is invaluable, to be able to have that there it’s just it’s pretty phenomenal. I like that idea a lot.

**[00:35:37] Jonathan:** I think lot more trust around Being able to just pull down report. We’ve not built a ton of reporting today. That’s an area that I we wanted to get as much information as we can to understand like what we have. And then another piece of product that we’re pushing out is gonna be just like more insights so we can drill down on product property level, spend really granularly, there’s a lot of folks who are investing in properties. Signed up some companies that you know that are much bigger and they have like really interesting businesses where they don’t need the same type of like owner level reporting, but they actually need they have LPs and they have like investors. And so there’s a different level of reporting that’s required therein. And so what we’re thinking through now and in the midst of beta testing is , how can we go get really granular reports that help them better process their. Monthly statements that they ended up, pulling back to LPs, so there’s a, there’s another piece of the business. There’s some things around man, there’s so much that I could delve into, but there’s a lot around the product that we see, we built V1 and the hard part is like building the bank, building the infrastructure. Now there’s just like improvements to the existing stack. We’re excited. Actually one more thing I can mention. We’re starting to partner with accountants to help potentially, like folks basically close their books. It’s, there’s a subset of folks who maybe, aren’t big enough for the big PMS systems where they’re doing full trust accounting, but need. To make sure they’re accurately accounting for every transaction. They’re closing their books, they’re following the right rules in their state or in, in their market. So we’re in a very early trial with a few folks to basically do this and then figure out how to productize some of that stuff to help the bookkeepers. It’ll save them money. ‘Cause we can. Basically pass off a lot of the time savings and the bookkeepers and toxic folks that we’re talking to are like this. We totally get it. And then on the other side, it saves the owners because, or the manager side ’cause they don’t have to pay some crazy cost for both. It’s like a much more

**[00:37:27] John:** Right, so you can come in, use it as a. Product or as a product and service essentially is what you’re looking at.

**[00:37:34] Jonathan:** that’s right. And it’s just still, trying to make sure you’re not biting off more than you can chew. But so far, so good. I think.

**[00:37:39] John:** Love it. Hey Jonathan, thanks so much for joining us, man. We’ve had a blast and learned a ton and. I know, we’re gonna keep seeing TopKey. We’re gonna see you partnering with more PMSs, seeing you pop up with, who are you guys using? Oh, we’re using TopKey. Oh, no, shit. It’s gonna be exciting to see your growth and we’re excited to go ahead and watch you scale and what’s next for you?

**[00:38:00] Jonathan:** I really appreciate. It’s awesome. Meet like-minded folks on the journey, right? Yeah, would love to, would love the next time I’m guessing we’re all gonna be in in some conference soon together. I don’t know if you guys are gonna be in Orlando, but I think there’s a couple down there.

**[00:38:12] John:** Yeah. Yep. I’ll be FAVR. We’ll be at in VRMA International in Orlando, so I’ll be at both of those. Yep.

**[00:38:18] Jonathan:** Awesome. I’ll see you guys there at both. All right. Thank you guys.

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