TTA06-Ben Wolff-Managing Short-Term and Long-Term Rentals During a Pandemic

Ben Wolff

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Episode 6: Ben Wolff

On today\'s episode, we have Ben Wolff. He\'s the co-founder and CEO of Pro Tripper, a full service guest communications and pricing solution for property managers and blink hospitality, a portfolio of vacation rentals. He grew to hundreds of properties across the United States over the past three years. Ben previously ran business development for a global vacation rental management firm, worked as a strategy consultant at McKinsey, and graduated from NYU.

Ben discusses the strategies he used to keep his business alive during the pandemic.

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Michael J. Mahony 0:01

The coronavirus pandemic is really taking a toll on many businesses will not survive. Listen to help link data managed to make it due to some very savvy business. Yeah, welcome back to another episode of the technology Alchemist, your source for technology advice, strategic technology planning, technology coaching, time saving advice, and a pragmatic look at increasing revenue and profit through your technology engine. I'm your host, the technology Alchemist himself, Mike Mahoney. So our sponsor is your virtual CTO. Your virtual CTO is a technology services company specializing in increasing your revenue and profit. Through a close examination of your technology engine. Your virtual CTO offers exclusive coaching for business leaders. That is the only business coaching program that includes technology as part of the program. You want to learn how you can make more money tuning up your technology engine, head on over to get your virtual On today's episode, we have Ben Wolfe. He's the co founder and CEO of pro chipper, a full service guest communications and pricing solution for property managers and blink hospitality, a portfolio of vacation rentals. He grew to hundreds of properties across the United States over the past three years. Ben previously ran business development for a global vacation rental management firm, worked as a strategy consultant at McKinsey, and graduated from NYU stern. Welcome to the show, man.

Ben Wolff 1:38

Thanks, Mike.

Michael J. Mahony 1:39

I'm wrapping your your company

Ben Wolff 1:42

pulled mine out, too. I love these hats. I gotta get some more. We got these before we went to the Philippines to visit my guest communication team over there.

Michael J. Mahony 1:51

It's very white that I will say, but I like it. And I love I love the colors too. But so why don't you tell me? So how did you decide to start your businesses.

Unknown Speaker 2:01

So I kind of got the entrepreneurial itch when I was I would say a freshman in college. It started by, you know, promoting off campus events, and you know, party club parties and things like that. And I also got involved in some, like entrepreneurship classes at the university, and you know, building business plans and things like that. And that, you know, progressed. And, you know, I went to NYU, I transferred from another university to NYU, and like, my junior year, and when I was there, the kind of tech startup scene in New York was really blowing up, you know, I don't know if you remember Foursquare, but Twitter was still relatively new. And, you know, Silicon Alley was kind of blowing up. And so I really would, you know, was drawn to that became very interested in it met a lot of people in that world. So, I mean, I knew I wanted to start something, it was just a matter of when, and I, you know, I've started various other small businesses throughout my career. And this business actually started from I had an event company prior, and, you know, part of my event company, we provide temporary housing for folks in the entertainment industry. So photographers, models, actors, people like that when they were in town. And we had this communal housing concept for them. That was, you know, kind of associated with our event promotion brand. And because of that, I had apartments in New York City. And that's actually what led to the first vacation rental units that we had, before New York City, kind of, you know, really cracked down on an Airbnb ease and short term rentals, we had some properties there, that, you know, we were making more money doing that than what we were doing before with the communal housing. So I kind of stumbled into it, I actually had a job doing business development with a, another vacation rental company, and I got a couple of properties that they were managing for me. And then, you know, after doing that, getting a couple properties, they were profitable, I decided that I wanted to build that portfolio. And over time, they got a little bit top heavy, they had, you know, took on too much cost locally, and they ultimately kind of went belly up. And so I ended up having these units that I had to figure out how to manage on my own and kind of learning from their mistakes, I decided to offshore and kind of keep things as lean as possible and leverage technology where we could to really, you know, keep our operating model very lean and adaptable, which you know, really helped us during COVID as well. So,

Michael J. Mahony 4:36

will you use the term offshore team which scares a lot of people and I find with my coaching clients that they they are afraid of offshore teams. So how what process did you use to build your team?

Unknown Speaker 4:48

So the process that I've actually been outsourcing for a while so I outsource when I had other jobs as well like I would outsource virtual assistants to just help me with like business development work and sales pitch deck. and stuff like that. So I kind of got tapped into it through other jobs where I had these virtual assistants. And, you know, guest communication, I knew was an area that, you know, we could definitely outsource. So I use Upwork, which is a platform that, you know, I've used before to hire virtual assistants. And I put up an ad and invited a bunch of, you know, Top Tier V A's to it, be a virtual assistant, and interviewed them and had them do like test tasks and things like that to kind of vet them and ultimately found one that, you know, actually, I found two that I really liked. And so I hired both of them. And one really turned out to be by far the the shining star who's still with us, and you've probably heard of from from your wife who works with us. Charisse is just, you know, I mean, she, she's just blossomed into not just an amazing VA, but an amazing manager and helped assemble this, you know, whole team, from people that she knows and past people that she's worked with. So it all started from finding her on up work. And, you know, she's kind of helped assemble the team. And, you know, I've tried to take care of them as best I can, you know, as an owner, and by doing that, I think it's led, you know, led us to be able to recruit a lot of talented folks that she knows,

Michael J. Mahony 6:14

well, you know, you mentioned, my wife works with you. And one of the things I've observed, you know, I've been managing offshore teams for probably 15 years now. And I can tell you a story of some I worked at a company that split into two. And the our CEO, was investing in the other company. And he kept saying to me, how come How come you're using the same offshore team as the other guys, you're getting work done, and they're getting nothing back. And I feel like I'm throwing money into this giant barrel and, you know, lighting it on fire. And it turned out that, you know, the difference was, it's similar to what you're talking about a treated them like they were working with me in the physical location where I was, I didn't treat them like they were some contractor that I should just shoot an email to, and the other company was, that's literally what they're doing 5pm here's a list of 10 tasks for you to do tonight. Well, of course, eight of them will have questions attached to them. So the next day, only two things got done, they'd respond to the questions. Now, maybe seven things were left and only one thing got done, it would take forever to get done. Whereas what I would do is have regular meetings where, and I know you do that you have regular meetings with your team. And I think that's the best strategy. I've recently learned. I've tried now three times to have a main executive assistant, who helps me with pretty much everything that I do in my business, but I'm finding that it doesn't work. Because these people are really, you know, if you find somebody, we've been tapping into Belize a lot, and the people in Belize are really good at one thing, or another thing or another thing, but when you try to put them all together, doesn't work. So I've recently converted to I have a person who does one set of things for me, I have another person who does another set of things for me. And while it's a bit more management for me, stuffs getting done, and that's really the objective. Right? So how has technology? Because obviously you have offshore team? How has technology helped you to run your business and manage your team?

Unknown Speaker 8:12

So, you know, I mean, I think that everything from you know, messaging platforms like WhatsApp, I mean, that's primarily what we use just makes it really easy to communicate, have multiple threads, you know, share photos, videos, whatever it is that we need to share to kind of, you know, teach them how to do things or, you know, teach teach amongst themselves as well. I mean, I think they use it for all of that. We also use, we use Trello, you know, as a way to kind of keep track of information about all the properties and you know, so hopefully, they're not asking the same questions over and over again, you know, they get because, you know, the team has grown, you have 20 people now, you have one person who asked the question, you don't want the same person asking the same question, you know, two days later. So we really tried to sort of Express upon them the importance of or impress upon them the importance of, you know, putting that information in Trello. So it's easily accessible to the other folks. So, so yeah, we use WhatsApp, we use Trello. We use, we use Google Voice, you know, we tried to leverage a lot of, you know, free or freemium, you know, products out there. We use Asana, you know, what I mean, just trying to keep costs low and keep things lean, like I was saying, Yes, we use Asana to designate tasks as well and, you know, determine who's going to do certain tasks, we use g drive, I mean, I could go on and on, you know, we use technology and all aspects and most of the platforms we're using are platforms that are free or very low cost and that are very easy to collaborate, you know, like g drive, we can easily collaborate with them in the Philippines and me in all standard Victoria in Southern California. And, you know, there's no version control issues, there's no lag, there's no you know, we're all editing sort of real time on the same documents, you know, and then WhatsApp, you know, and Google Voice and these other platforms that are just allowing us to communicate for free or virtually for free, despite being you know, Hundreds of 1000s of miles apart.

Michael J. Mahony 10:02

What made you choose WhatsApp over say something like slack or Skype or something of that nature.

Unknown Speaker 10:08

So the reason that we started using WhatsApp is B, I think the main reason was that a lot, a lot of cases we are using on WhatsApp with our clients as well. So and it's a much sort of lower barrier to entry to because most people have WhatsApp, or at least have heard of it. Either way, it's free, it's very easy to use very intuitive, it's like, you know, consumer facing, it's not a business, you know, facing product. So it's very easy for us to ask a client to hop on WhatsApp, get an A group thread with them, to be able to communicate with them, I think, at some point, we may develop our own proprietary system and, you know, have it look a little more, you know, like white glove ish, if you will, with kind of the blink branding and whatnot. But I mean, at this point, you know, especially with everything going on, and happy that we've you know, been able to leverage existing technology out there. And, you know, I mean, in some senses, it's a minimum viable product, but it works. And we haven't had the need to kind of, you know, spend to, to, you know, rebrand it to make it look like it's our own.

Michael J. Mahony 11:06

That's it, that's a very smart move, because that that's actually, you know, one of the programs we offer, we guarantee we can increase someone's profit 10% minimum. And one of the one of the easiest ways to do that it's the low hanging fruit like that, I'll find, I'll find people are using five software's that I'll do the same thing. But they're using one for one thing, one for something else. And then you say, Well, what, why, you know, like, just use one. And yeah, maybe that one feature isn't as great as the other one. But why are you paying all this money, for things that are all doing the same thing makes no sense. And like you mentioned, minimum viable product, I think that's the key to is, figure out what your needs are. And then find something that will meet those needs, as best as Can, can nobody, you're not going to get perfection, but you'll get there. And you're proving that you can run a pretty large scale business without having to spend a fortune on technology. And that's, to me, that's a real big key. And when we when we started our business, that was a big one for us, we needed, I'm big on having processes. And Victoria at the time was not real big on having processes. So we, we had to get the software that she would use, and I felt comfortable was controlling what I needed to have control. And we've evolved over time to different to other software, but only because our needs grew more than anything else. But again, just like you, we look for anything that's either as free or super cheap. Because I am of the philosophy that spending all of your profit on stuff like that. It's just crazy. I recently saw a shark tank episode where people were, she was making $120,000. And she spent 100,000 to obtain the customers and I thought, wow, like, how is that sustainable over the long run? Right? So, you know, the world's kind of changed, obviously, as we all know, how has this pandemic changed how you do business?

Unknown Speaker 13:08

I mean, it's really turned it on its head is what I can tell you, from the get go. I mean, certainly nothing any of us saw coming. It's it's decimated our industry, you know, I mean, I'm, I'm grateful that I don't have 50,000 hotel rooms to worry about filling, you know what I mean? Like, I can't imagine being a Hilton or Marriott, or, you know, one of these companies that and you know, they're getting government bailouts, I'm sure at some point to sustain, but I'm grateful that we are small and nimble and have kept our team very lean. And also, because we've offshored, we've actually been able to retain more of our team, because, you know, the labor is so much less expensive, relatively that, you know, firing half that team doesn't really move the needle for us. So I'd rather you know, keep them so I have this strong, you know, cohesive group, as you know, hopefully things turn around. But yeah, I mean, we had to do it, we had to make a lot of shifts, you know, I mean, the first thing I tried to do first two things was how do I reduce costs as much as possible? And then how do I bring some revenue in the door, which was basically trying to convert all of our listings into long term rentals. So instead of short term rentals, weekend stays week long stays? I actually think the industry calls it midterm stays not long term, it's like two weeks to like three months, is kind of the sweet spot of where we've tried to transition. So that, you know, I didn't want to lock up our places for a year, in hopes that, you know, hopefully, things will pick back up a little bit. And, I mean, we've finally started to see that a little bit and some of the markets in the northeast, you know, some of our other markets is having a resurgence. So those are kind of getting hit now and kind of closing down again. But, you know, the midterm stays, it helped a lot month long bookings, two week bookings, things like that. And in sort of concert with that working with our landlords, and basically just, you know, being like this is, you know, for special events, you know, no could have predicted this, we're actually not able to safely conduct business, you know, as we have been let alone if we, you know, had people that were traveling, so we were able to negotiate with the landlord's mean, partially because, you know, I don't think they thought they had much better options, you know what I mean, then to keep us down. So it's like, what are you gonna do if we leave, try and find a long term tenant in the midst of a pandemic, you know, it's not necessarily easy to do. So they were willing to work with us, I think it's also a testament to, you know, relationships that we've built with them, we've always paid on time, we've never asked for consent, you know, never asked for anything before. So I think when I came and ask, this time, they were, you know, ready and willing to listen and work with us, and basically just pitches like, hey, like, if you want us to be around for the long haul, and to kind of make it and survive, and, you know, I need you guys to work with us in this time of need. So, and pretty much all of them were able to do something for us. And I opted for trying to get reduced rent, instead of just sort of, instead of pushing the rent down the road, you know, having to pay it back later, instead of delayed payments, I tried to negotiate just reduced rents. And you know, the pitch to them is like, hey, you're getting some money now. And the benefit for us was that we were not digging ourselves into this pile of debt hole that we have to dig ourselves out of later. So it's like, how do we, you know, reduce our rent to the level that we can actually cover it or close to cover it with these midterm stays. While we're, you know, waiting for think things will hopefully turn around a little bit. So we did that. Like I said, it didn't really cut much of anyone on the team, we trimmed ours a little bit on the offshore team, just because we didn't need the same capacity, you know, so we trimmed ours a bit, though, they were still quite busy fielding all the cancellation requests, and all of that, you know, pretty busy for a while there. So we, we trim to the tee either the hours a little bit without, I don't think we fired anyone that wasn't performance based. And when we looked for government assistance, where we could, you know, we apply for the PPP, or we applied for the EDL, both of which we were able to obtain, which, which is great. And, you know, I mean, that ideal loan, yeah, you have to pay it back, you don't have to start paying it back for a year. And I mean, the interest rate is as low as you're ever gonna find anywhere. So it's basically free money, you know, I mean, in terms of trying to sustain ourselves, and, and make sure we have that, thankfully, we haven't had to dip into that that much yet. Because we've been able to reduce costs so much and, you know, get some of these midterm stays. But you know, with with seeing the second waves and stuff like that, it's definitely nice to have the security blanket.

Michael J. Mahony 17:44

So talk to me about reputation. So both reputation with your clients, and reputation with your team, how important is maintaining a solid reputation with both sides?

Unknown Speaker 17:54

Yeah, so I actually take a try to take a team first approach, because I believe that if the team is happy, then that will flow down to better treatment and willingness to listen to customers and try to you know, improve their experience as much as possible. I feel like if you have a disgruntled team, then it's, it's, it's harder for them to, you know, be be friendly, and you know, willing to bend over backwards to help a club customer. So we really tried to take that approach. And, you know, I picked the Philippines to outsource because in all my dealings with VA is I have found Filipinos to be the most amenable friendly, you know, just just their voices to thing, you know. So I've really found that, that working with the Filipinos has been a great decision in terms of, you know, having good relationships with our customers who they talk to on a daily basis that are renting our units.

Michael J. Mahony 18:49

Well, and obviously, as you spoke to before, having a good reputation with your landlords that you work with, working to your benefit as well.

Unknown Speaker 18:59

Oh, for sure. Yeah, I wasn't thinking on that side. I was thinking more guests related. But yes, certainly, relationships with our landlords relationships with our contractors, you know, the people that, that clean our units and, and, you know, that's actually another area, you know, all of our local contractors, because I talked about our offshore team in the Philippines. But literally, there's a lot of work to be done on the ground with short term rentals, there's cleaning maintenance, you know, guests get locked out whatever it may be sort of issues that happen on the ground. And that was actually another group, another group supplier of us that I didn't try to Penny pinch at all. I mean, I didn't ask them to reduce their rates because the number of cleanings they were doing dropped off a cliff. So I already I already knew how much they were hurting. So you know, I didn't ask them to cut their rates even further. And I actually you know, I encourage them to apply for PPP, ADL, some of the things that we were doing to hopefully allow them themselves, you know, them to sustain themselves as well. But yeah, we built you know, really long term, strong relationships with our local society. With our landlords, we have a lot of landlords that whenever they get a new property, they bring it to us first because they know they're going to get paid rent on time, they know I'm going to be transparent, you know, they know we're going to take care of the property, they know that, you know, if it's a small maintenance issue, we're probably going to take care of it ourselves, instead of asking them to do it, because it's just faster, you know, to just do it ourselves. And as opposed to a tenant that you know, every little thing they're calling on the landlord to come fix. So, you know, there's a real and, you know, there's a lot of reasons that it makes sense for them to want to continue to work with us. So

Michael J. Mahony 20:31

with the pandemic going on, and the concern about, you know, people getting infected. Tell me what you're doing to make sure that any guest that chooses to book a stay with you, feels comfortable and safe.

Unknown Speaker 20:46

Sure, yeah. So we have some of that listed on our listings. So we have it in the description, what we do in terms of our cleanliness standards, we follow the CDC guidelines, we use, we even go above and beyond that we use airborne sanitation. So we use ozium devices in a lot of our, our markets, we started doing it in New York, just because you know, we have some markets, some units in New York and Jersey City. And it sort of height of the pandemic, you know, we wanted to take every precaution that we could. So we use the ocm devices, we also made sure there was at least 24. And in some cases, up to 72 hours between stays, depending on the market. And you know, how kind of severe the surges were and how prevalent COVID was. And you know, normal disinfecting all of our cleaners are wearing masks and gloves. And, you know, disinfecting all services as they would normally. But that in conjunction with the airborne cleaner and having, you know, certain gap between guests. That's what we've done to try to limit risk. Yeah, it

Michael J. Mahony 21:46

makes sense. I mean, advertising, it is really smart. Because we we I had occasion to be in Vegas for a weekend. And there, I actually felt safer there than I do here in California, because we have actually stricter rules here. But they were actually enforcing the rules there. And that's the difference to me is, you know, you go to hotel, and they now have guards at every door that tell you hey, you got to put a mask on, can't come in if you don't have a mask. And then of course people put the mask on walk by take the mask off, and then all of a sudden, there's another guy, hey, you tell it you better put a mask on, you don't put the mask on, you got to leave that and so you find pretty quickly people give up trying to like, you know, game the system, but also just the whole concept. Like they don't, they don't come in and clean your room in between each day anymore. Because, you know, we people don't, I personally wouldn't have cared but people are uncomfortable having a stranger come into the room and, you know, potentially infect them. It was it was interesting to see though, because it was all about the marketing, there were huge signs everywhere talking about these are the steps we're taking, these are the steps we want you to take. And together we can make it safer. And I think that for your industry is going to be huge going forward. Because people have this opinion, when you talk to them that an Airbnb is not as clean as a hotel, I actually kind of think it's the other way. But they they have that opinion. And you're gonna have to overcome that opinion by doing what you're doing, which is brilliant. I mean, you, you have to make people comfortable, or they're not gonna, they're not gonna stay, especially long term, because they're gonna wonder well, who was here before me. So I think that's, I think that's great. So we've talked about your technology,

Unknown Speaker 23:29

I just want one quick thing about the, the hotel versus vacation rental. And we've actually seen a lot of data that's supporting that people are preferring Vacation Rentals these days, particularly urban areas, you know, are just kind of hurting in general, but rural and suburban areas outside of the major cities, they're preferring Vacation Rentals to hotels, I think because it is that much more private, you're not having staff, you know, all throughout, there's just less people that you're sharing surfaces with and, you know, modes of transportation. So, you know, we're actually hopeful that, you know, this will this will help kind of some of that shift from hotels, to vacation rentals, just viewing it as safer and all that, but it certainly is up to the community to express to guess all the precautions that we are taking. Because, you know, we may not be viewed as, as much of a robust, you know, professional organization as maybe a hotel group. So we need hosts to really, you know, present all the things that we are doing to keep guests safe. So that guests think of short term rentals as being as vigilant as a hotel would be as you said, I

Michael J. Mahony 24:31

totally makes sense because that was my one complaint about staying in a large hotel was when I leave there even though there was maybe a 10th of the people staying there that would have been there's still other people you know, whereas in a in an Airbnb in it, I can come and go, I'm not running into crowds of people as I leave and come back. I'm not waiting through, you know, a casino to get to my room. There was a lot of things I mean be uncomfortable about the whole process. Especially someone who's kind of on the close to the riskier side of things, you know, I'm 55 years old. So it's like, I'm right there. And it was nice to see. But what I was What irritates me here in California is I follow the rules wire and other people following the rules, you know, you kind of say that to yourself, at least. And when I was in Vegas, they have, you know, face coverings there, people are doing what they're supposed to do. And so you felt like, Alright, well, you know, I don't mind chipping in and doing my part if everyone else is going to do their part. That's kind of interesting, though. I think maybe that's a marketing move you can use when things start to pick up is comparison to you know, what, we don't have big crowds that you have to go through and things like that. I mean, and it's, it's great, because it's not a scare tactic. It's the truth. You know, I mean, that's the, I think the, you know, my ex wife works for the Marriott hotel chain, and they kind of use scare tactics of, well, you know, you can trust that we are regimented and do these things. But you can't really trust that those people are doing that. And I actually don't agree with that, I think that you're using contractors to clean in there, and that's their livelihood. And so they're going to make sure that they don't mess up. You know, that's just make sense to me.

Unknown Speaker 26:20

Yeah. And I mean, look, we're, we really try to work with good people. And I think, you know, good people are going to do the right thing, you know, they're going to try and limit risk as much as possible right now. Um, you know, of course, they're worried about the reputation, but I mean, all our cleaners, like, cleaning is what they do. So they take it really seriously and anything they can do to, you know, I guess, help to limit the spread of this, you know, through their, their what they do, I mean, they're going to do it, and they have so

Michael J. Mahony 26:48

great, well, why don't you tell our listeners where they can find you? If they want to, if they want to book a stay where they can do that?

Unknown Speaker 26:56

Yeah, sure. So you can find us at stapling comm, you'll see a list of our units there. And, and links to you know, booking links, as well. We also have a service called pro tripper, which is what Mike has shared there, that's kind of covered up, but pro tripper is a service that we offer to other hosts. So, you know, we established this guest communication team in the Philippines and our other I think, biggest core competency and value that we bring to management is dynamic pricing. So you know, we use dynamic pricing software, we also use our own internal pricing experts to sort of improve what the dynamic pricing engines do. So the pricing in conjunction with the guest communication is a service that we've decided to package and offer to other hosts and other managers. So you know, basically you can and it's, it's actually one way to change fixed to variable costs right now. So instead of having, you know, your own increase team that's local, that's pretty expensive, or, you know, revenue manager that's local or something like that, you could outsource pricing and, or guest communications to us. And we do it on a percentage of bookings basis. So for for 10% of bookings, you can have both of those services. And for 6%, you can have either one of them individually. So and those numbers are negotiable. If it's somebody coming to us with 50 properties, or you know, a large number of properties, we'll do, you know, bulk pricing discounts. So yeah, that's, that's appropriate for that that's a brand and an offering that we launched last year, because we had really refined these services within blink. And, you know, we we wanted to offer them to others. We had some people in our space asking us to use our team. So we were like, I guess we should package this and sell it as an offering.

Michael J. Mahony 28:42

That's so interesting, because I actually did a stint as a CTO for a restaurant delivery service. And it was the same thing. We perfected so many of the processes in the industry, that we started packaging them up and selling them as add ons to people along with the software that we built. So yeah, it's kind of interesting to parallel but but thanks so much for being on. We really appreciate it anyone looking to book, you know, definitely stabling calm and and you'll get taken care of really well. Like he says, I think you're probably the one of the few companies that do this that has such good dedicated customer service. And it was one of the things I wanted to highlight about your business because it's impressed me all along. And I feel like people need to know what kind of goes on behind the scenes, you know. So anyway, again, thanks for being on and thanks everyone for listening to the technology Alchemist.

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The Technology Alchemist is your source for technology advice, strategic technology planning, technology coaching, time-saving advice, and a pragmatic look at increasing revenue and profit through your technology engine. Sponsored by Your Virtual CTO, this show is the only one of its kind that blends business coaching and technology advice. The show is hosted by Mike Mahony, the world\'s most user-friendly technologist.

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