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- [00:00]
Will Smith
Rumors of their demise were greatly exaggerated. I'm reminded of that famous Twainism when.
- [00:07]
Jared Benoff
Thinking about travel agencies, which the Internet.
- [00:10]
Will Smith
Had supposedly killed off long ago. But today's interview is the second in recent months where my guest bought a healthy travel agency business. You'll recall Shell Zhang's interview in January. Shell bought Nada's Italy, a business that.
- [00:25]
Jared Benoff
Does group tours to Italy.
- [00:27]
Will Smith
The business that today's guest Jared Benoff acquired also targets a niche destination, weddings. This niche focus does seem to be the key for modern day travel agencies to thrive. And the subject of today is indeed thriving.
- [00:43]
Jared Benoff
Great margins, a completely virtual business, around.
- [00:48]
Will Smith
A million dollars in SDE and of.
- [00:51]
Jared Benoff
Course expensed trips to Cancun.
- [00:55]
Will Smith
Another feature of Jared's story that we spend time on the sellers of the business he bought were his parents.
- [01:02]
Jared Benoff
We learn all about that dynamic.
- [01:04]
Will Smith
For another story on an acquisition entrepreneur buying his parents business, see my interview with Jordan Evans.
- [01:11]
Jared Benoff
From July.
- [01:12]
Will Smith
Jordan's parents had a language services business which he has taken from 700,000 in revenue to 12 million. Okay, here is Jared Benoff, owner of Vacation Ease. M and A Launchpad is back for its spring show. M and A Launchpad is a one day event that brings together searchers and independent sponsors, seasoned business buyers, owners and private equity investors to go deep on buying businesses, finding financing and closing acquisitions, meeting investors and lenders, learning value creation from those who have done it. These are just a sampling of the workshops and panels that are packed into.
- [01:57]
Jared Benoff
A very full day and that day is May 3rd.
- [02:01]
Will Smith
The show is in Houston. The organizers are running a promotion just for US$200. Off with the code acquiring minds. Go to malaunchpad.com and use the code acquiring minds.
- [02:16]
Jared Benoff
All one word or use the link.
- [02:18]
Will Smith
In the show Notes welcome to Acquiring Minds, a podcast about buying businesses. My name is Will Smith. Acquiring an existing business is an awesome opportunity for many entrepreneurs, and on this.
- [02:40]
Jared Benoff
Podcast I talk to the people who do it.
- [02:42]
Will Smith
What do the following Acquiring Minds guests all have in common? Doug Johns, Morley Desai, Tim Erickson, Chirag Shah, Shane Ursum. They all went through the Acquisition Lab, the accelerator in community for people serious about buying a business. But they represent just a sliver of the Lab's success stories. The number of deals across the lab's cohorts now stands at over 120, with over $300 million in aggregate transaction value. The Acquisition Lab was founded by Walker Deibel, author of Buy Then Build, the book that introduced so many of you to the very idea of buying a business. The Lab offers a Month long, intensive, almost daily Q and A sessions with.
- [03:29]
Jared Benoff
Advisors, live deal reviews with Walker, deal.
- [03:33]
Will Smith
Team introductions and in an active community of serious searchers. Check out acquisitionlab.com link in the notes or email the lab's co founder, Chelsea Wood.
- [03:44]
Jared Benoff
Chelsea buythenbuild.com Jared Benhoff welcome to Acquiring Minds.
- [03:52]
Jack Benoff
Thanks, Bill. Thanks for having me.
- [03:54]
Jared Benoff
Jared, two big themes to your story today. First, the industry that you bought into, the travel agency niche, which I think is bound to surprise people as it did me.
- [04:07]
Will Smith
And second, buying a business from your parents.
- [04:11]
Jared Benoff
Let's get into it, Jared. I think the story begins with your parents being entrepreneurial and you're as you grew up.
- [04:19]
Jack Benoff
Yes, that's right. Yeah. So it, it started, I mean, I grew up in an entrepreneurial household and, and my friends roasted me for a long time that I would have to submit invoices and, and P L's during college to my, my par, you know, send me some money for college each semester. But that was the mindset. I always thought that was normal. And so I grew up around this. And you know, one of the things that my dad said to me when I was pursuing, you know, a career post post grad is it just don't get a government job. And he said that, you know, somewhat facetiously. And what did I do? I went and did public service for a little bit and I loved it, I adored it. And I learned a ton working in the federal government and that actually propelled my career. And I was able to then go from the government to working at Twitter where I worked with many government partners across the aisle and up and down government and helped them leverage social media tools. And again, like, that was the early days of me kind of figuring out, like, what is my sales pitch and, and how do I work with partners. And from there I moved closer to the sales side and that's what I did for about nine and a half years at the company. But I always had this itch and I always thought about, you know, what would be next. And my wife and I had these discussions, you know, what do we want with our lives and what do we want for our careers? And, and I always knew that, you know, my upbringing had a massive influence on me. And I, I thought, you know, I, I want to do this entrepreneurial thing. And I, I looked around, I looked around, I would talk to brokers, I'd, I'd be one of those tire kickers. Honestly, like, I had this moment of reflection where I was like, what am I doing? Like, I'm not About to go buy a pressure washer business or, you know, an H vac business. Like, that's not me. I'm, I'm, I've grown up around computers. I'm a social media guy. And, and what I realized over the course of a few years was like, the business that I wanted to acquire was right in front of me. It was started by my parents. And so that's when I had that moment of, okay, take a step back, look in front of you, and recognize the opportunity right there.
- [06:08]
Jared Benoff
Great. Well, let's unpack some of that. First of all, nine and a half years of Twitter.
- [06:12]
Jack Benoff
Yeah.
- [06:13]
Jared Benoff
From what year to what year?
- [06:15]
Jack Benoff
From 2015 to 2024 to the end.
- [06:19]
Jared Benoff
Of 2024 to the end of. So three months ago.
- [06:22]
Jack Benoff
2025. Yeah. Yeah.
- [06:24]
Jared Benoff
So you were there during the Elon acquisition?
- [06:27]
Jack Benoff
I was, yeah. Our team, I was on the sales side, based in New York City, selling, you know, working with Fortune 500 advertisers, selling them, advertising. And so I was there throughout the transition, you know, late night emails from Elon and his new team and trying to understand the business and working through that was a wild, wild roller coaster.
- [06:48]
Jared Benoff
Wow. Well, given, you know, that it's its own podcast, so we're not going to spend much time there. But given that you experienced that, that front lines from within Twitter, slash X and also that you have this government experience from before you went to Twitter, you just probably have a very unique perspective on all these emails that are going out to federal employees like you. You probably can understand better what that experience is like than even people experiencing it. Because you, you've received emails like that only at Twitter.
- [07:18]
Jack Benoff
Yeah. I definitely empathize with everyone with what's going on. You know, the pace of Elon and his team is incredible. And so I empathize with everyone trying to grapple with that.
- [07:28]
Jared Benoff
Yeah. And then you, as you were, you know, going through your tire kicking phase. So it sounds like the entrepreneurial itch that you had was always going to manifest in buying a business as opposed to starting something. Being that you were in, at Twitter, exposed to tech in tech in New York, you didn't, you didn't have a startup idea that was the path instead.
- [07:53]
Jack Benoff
Not really. I thought about this a lot and, you know, early days, I would think about starting a business, you know, whether that be an agency or something more service driven or even product driven. But I realized my skill set is more in growing things and, and building, you know, taking it from one to a hundred. I realized I'm not A zero to one guy. Like, it's just not my strengths. And so I, I honestly, through a lot of the SMB Twitter community, saw these stories of people buying businesses and acquiring businesses, and that seemed to resonate much more with me in that journey than even being around, you know, so many people in the tech community, both at big companies like Twitter and Facebook and Google, as well as some of the smaller startups in the ecosystem. Like, I just found myself gravitating much more towards the acquisition space.
- [08:39]
Jared Benoff
So your exposure to ETA actually was via SMB Twitter? Via Twitter, where you were also working as ad sales?
- [08:47]
Jack Benoff
Yeah. I mean, yeah. It's so funny. We used to joke with our clients when I was working on Twitter that so much of our job is living on the platform and experiencing the content and seeing what people are saying, you know, what's the meme of the day? And for me, it happened a lot during the early days of COVID when SMB Twitter really blew up. I found myself just gravitating towards that community. And I would reach out to people just saying, hey, I'm curious about what you're doing here and tell me about your story and let's chat. And I think people were very open in those days to chatting and just sort of talking to other people. And I just found myself going down these rabbit holes of, of talking to different business owners and different people in the ecosystem, and I fell in love with it. Like, I thought it was the coolest thing and such a great way to build a life.
- [09:32]
Jared Benoff
Well, probably some of those people are. Have been on this podcast. Yeah. And you talk about it. SMB Twitter, as that was kind of the golden age. Do you think that it's changed?
- [09:43]
Jack Benoff
I think it's evolved. I think the platform's evolved. I still think there's so much great content out there and people are so generous with their time. And so many people who I've talked to over the years and many who I haven't even talked to are just generous with education and knowledge and experience. And I've been the lucky benefactor of that, as I'm sure many others have been, you included. I mean, you do this podcast and get people to share their stories. And I think the platform has changed, but, like, I think there's still these niche communities out there where people are collaborative and engaging and doing it for all the right reasons, which is great to see. And it's partially why I stuck around for nine and a half years, because I love the platform and there's so much value that People can get when they use it to the in the right way.
- [10:28]
Jared Benoff
Okay Jared, so returning to the plot then. So you, you, you, you say to yourself I'm not going to buy some blue collar business. That's just not me. I've grown up with computers. I've been you know, in tech land and been basically, you know, sponsorship sales and so on. So the idea of buying a power washing company just doesn't, doesn't quite make sense. It's interesting that I don't have more people kind of hit that wall because many, most probably of my guests are coming from a white collar environment and yet they plow forward with the, with those types of businesses. I digress. You have a business right in front of you, your parents business that seems like the best candidate of all other than it not being a kind of blue collar trades business. Why else was it a good candidate?
- [11:17]
Jack Benoff
I mean let's invert the question like why was it a bad candidate? Is it, you know, it's largely project based which I'll speak about. There was a lot of key men risk that. It was like my dad running the show for a long time and you know, everyone else sort of supported him long sales cycles and so many other things in the traditional like ETA community that you'd look at this business go eh, it's not great. But for me again like I had heard so many people talk about just do your first deal and like get that experience. And this seemed like the logical path forward where I love the industry travel, I like the lifestyle that it allows, I love the interaction with other people and I love you know again these things that might not be attractive to a normal acquirer. I love because I grew up around and I saw my parents do it and I was like I could do this and you know, I knew the things that they were doing and I saw the sort of future looking arbitrage opportunities with the business to say okay, this is what's working for them and I see how it's working and I know that you know, with some fine tuning with some different systems, with some marketing and I know that's sort of like a cliche thing like oh, just like ADD marketing, like sprinkle it on top. Yeah. And in this case like there is a lot of that that rings true. And so I saw that opportunity working and supporting my parents in some ways that like okay, if I take this over like I have a plan to sort of see through the next 10, 20 years.
- [12:41]
Jared Benoff
Yeah, well I, I think another part of the. Your appeal Here is because you, you were already very familiar with the business. I mean meaning not just because your parents, it was your parents business but you'd actually helped them a lot and worked inside the business as an unpaid consultant. I guess so. So you really knew the inner workings. This is probably. Why don't we get the history of the business and this involves your, your dad a lot. Because that I think is just helps paint a picture too of how you perceive the opportunity. So. So maybe give us his story in this and this.
- [13:18]
Jack Benoff
Yeah, it's interesting. So again like I grew up in this entrepreneurial household and so when I was younger my dad had started a website where you could book honeymoons online. At the time, you know, this is like 1999, 2000, it's a novel idea. You nowadays we're like well duh, of course you can do that. But at the time no one was doing that. And so he started this website, he sold that to the Knot which if people aren't familiar it's you know, one of the largest companies in the online wedding space. They were publicly traded for bit I'm not sure if they are anymore but so he sold to them in around 2000, 2001 and had just been tangentially involved in the wedding and travel space ever since. You know, through consulting, through helping other travel agencies, things like that. And about 15 years ago my parents were empty nesters. Me, my brother and my sister were off at school and I think they were kind of like yearning for that next thing and they were like well we have, you know, our clients who we still help with travel on the one off basis. Let's just give it another, another go and build up another travel agency. And what they did was they, they just started out just sort of serving everyone and they realized like that's not going to work on that traditional travel agency model that you know, you and I might think about was disappearing very quickly. And so they decided to focus on specific niches, particularly around destination weddings. You know, this was starting to be a more popular. And so they went all in on destination weddings, particularly in Mexico and the Caribbean and just became the go to experts. And my dad to his credit was like I'm just going to educate people. Because people didn't know that you could save a lot of money by having your wedding abroad, that there were all these other ancillary benefits. Plus who wouldn't want to go away for three, four days with some of their great friends and family and enjoy a vacation together. And so they specialized in that and grew the business pretty quickly again because there weren't many people specializing that during that time. Again, this was really just my parents sort of side thing just so that they could do some fun travel and, and get paid to do it. And you, they'd come to me for help, they come to my brother for help and it was like, hey, build us a website or hey, like help us, you know, send PDFs to people. Like they were doing that at the time and all these little things over time and you know, I just kind of fell in love with it. I never again, like at this point, 10, 15 years ago, I never thought like, oh, I could do this one day for myself. Um, but I loved helping them and I loved, you know, the limited interaction. If they were going on a two week trip and they're like, hey, do you mind if people call? Just like sort of screen the calls and just send us an email after. I'm like, yeah, for sure. Or if, you know, so and so wants help with a honeymoon, can you do that on the weekend? So yeah, for sure. Um, and so all these little things over time just sort of snowballed into me falling in love with the, the nuances and intricacies of the business. Fast forward today. I mean, they're doing about a hundred weddings per year and some ancillary other travel. And I'm, I'm happy to like unpack what that looks like, but it's obviously a bit larger than when they just started it and it was just the two of them.
- [16:08]
Jared Benoff
Okay, so just to, just to distill some of that, they kind of started this as a side thing, almost, as a, not a side thing, almost like a hobby in a way to, in a way to expense going, you know, doing some of this travel themselves. And, and, and they also identified a niche because the traditional travel agency where you pick up the phone and you say book me a flight to Paris is long gone.
- [16:33]
Jack Benoff
Right.
- [16:33]
Jared Benoff
But, but, and this is key to the opportunity here, these niches within travel. Still, certain consumers, certain markets still seek consultants, if you will, to help them plan a trip. And your parents identified destination weddings as just such a niche. And obviously you can imagine why that's, that's much more than just booking me a flight. It's, it's a huge amount of logistics, it's international, et cetera. It's also high ticket, something that we'll return to again. And while we hear a lot about destination weddings today, in 2009 and 10, it was, it was not as common. So they so they were also riding a trend that they saw growing. It is today. We're going to get an update on where things are today. But it's actually, it's not just the two of them. It's a team. It's a proper business. It's not just them as kind of consultants, if you will. And you were helping them all along the way, getting to see inside the business and indeed interacting with, with clients a little bit. These 15 years of growth, did they.
- [17:37]
Will Smith
Intend for that to happen?
- [17:39]
Jared Benoff
You said why they started it was just to kind of feed their scratch their own travel itch. But did they, in their fantasies imagine building a business here?
- [17:47]
Jack Benoff
I don't think so. My dad's always, he's done a lot. Like I said, he's super entrepreneurial. Like, I'm so impressed with everything he's built over many, many decades. And like at one point he owned a few restaurants and he's like, that was a nightmare. Like I had so many employees and so I think sold the restaurants and was doing some other stuff and started the travel agency. It was like, I just want to work with, you know, my mom and just do this ourselves. But then it was like, all right, well we can't do eight weddings a month. We can't do 12 weddings a month. And so slowly it was like, all right, let's go find like one person to help them. Two, then three. And ultimately like coming out of COVID when things were just absolutely mayhem and travel opened up and all that pent up demand that people have heard about, you know, he was sort of like, well, now we're capped. Like, I don't want any more people. I don't want a big business. Like, I don't want, you know, 50 people working for us. And so he kind of capped, he was like, all right, if we can just do 12 weddings a month, I'll be, I'll be thrilled at sort of what he. So he capped it. I mean, during 2022 and 2023, when things are really rolling, he was turning away many couples every month just because he didn't want this huge enterprise. And then he was like, well, maybe I'll retire and sell the business to someone not knowing that that was going to be me at the time. And so he was like, all right, like, let's think about what growth and systems and things like that look like. But yeah, I mean, when they started, you're, you're spot on. Like, this was really just a, a lifestyle for them to travel and get paid to do that.
- [19:08]
Will Smith
You know that one of the most common levers to pull in a target acquisition is technology updating the systems of a business that may still be running off a spreadsheet or even pen and paper. But tech is complicated with tons of solutions out there. So choosing the right cloud platform, CRM, telephony, compliance and cybersecurity, not to mention implementing all that, is a job in itself. Acquiring minds Guest Nick Akers knows this firsthand. As a former searcher who now owns Inso Technologies, Nick has seen the tech challenges searchers face when acquiring businesses. His team at Inzo regularly works with searchers and their acquisitions, offering a complimentary IT audit of the target company. Nick takes a personal interest in all their searcher clients, drawing from his own experience in the search phase. Enzo dates back to 1989. So this is a company that has managed the tech for hundreds of small businesses over decades. And one last thing, no long term contracts with Enzo. A big differentiator. Check out enzotechnologies.com I N Z O or email Nick directly@nickzotechnologies.com and don't forget to tell him you're a searcher.
- [20:31]
Jared Benoff
Okay. And so bring us back up to the present or basically when he sold it, what did the business look like at that point?
- [20:38]
Jack Benoff
Yeah, so the business does about 100 groups a year, a little bit less. And when I say group, you know, that's. Sometimes it's mostly weddings, but that might be a 50th birthday, that might be a bachelorette trip, things like that. But typically, like, where we specialize in, like our zone of power is, is with small niche group travel. The average group has about 60 people in it. So you can imagine what that looks like. We've got about 10 people on the team now. Most of those folks are helping the, the clients with their travel. And like I said, like a few years ago when I sort of came to this realization that I was interested in acquiring the business, and my dad was thinking, I'm tired, I'm like ready to be done with this. He kept joking with me, I'm gonna sell the business for six times multiple and yada, yada, yada, private equity. I was like, okay, well what about me? Like, I'll buy the business from you. And like, it started out as a joke. And then eventually we both kind of came to the middle and we're like, all right, well, like, maybe I will acquire this business. And here's. And he was saying, maybe I will sell it to you. And so, you know, over the course of A few years we became more serious and had many discussions about that and what that would look like and, and how to sort of operationalize that so that I could have a smooth transition. But yeah, I mean, it started as almost a book and, and obviously became more real in the last few months.
- [21:56]
Jared Benoff
Well, let's get into the numbers of the business then. Let's spend some time on a travel agency business and why it's appealing and then we will get to how one actually buys from their parent and, and the obviously delicate negotiation there and how, how can you be arm's length, et cetera. So you said a hundred weddings or groups a year. The average group size there is 60 people. So that's. So that's 6, 000 trips.
- [22:27]
Will Smith
Individual trips.
- [22:28]
Jared Benoff
You're planning a year or selling a year. What's the average? Can you give us what revenue is of the business?
- [22:34]
Jack Benoff
Revenue last year was about $8 million. And that's gross booking revenue. So that's sort of all the trips added up.
- [22:41]
Jared Benoff
That's all the tr. And so that's gross booking. So if you book a hotel, that's what you're basically paying to the hotel.
- [22:48]
Jack Benoff
Exactly.
- [22:48]
Jared Benoff
Customers are paying you. What is your, what is your net revenue? So your cut before your own internal.
- [22:54]
Jack Benoff
Expenses, it's about 15%. So about on that 8 million is about 1.3 million.
- [22:58]
Jared Benoff
Okay.
- [22:59]
Jack Benoff
And the beauty of, I mean to your question, like the beauty of this business is it's low overhead, there's no inventory. It's asset light. Like the real only expense is people. And so your margins off that, you know, sd, when I was talking to my dad and we got more specifics about the deal on the $1.3 million in commissions paid to us, about 950,000 of that was SDE. So you're. The margins are pretty amazing. And again, this is the big difference between what you would consider a traditional travel agency and something that is more niche specific and has evolved to the Internet era. In some ways, you know, in some ways we still haven't completed that cycle. But that's what was super appealing when I started to understand these numbers. It's like, okay, I'm, it's a laptop business. Like I can be anywhere in the world and operate this business. The only expenses are other people. And you pretty much know, I mean, things are fairly predictable. It's like, okay, if you have a group, you know what your average ticket generally is, you know how much people are typically paying, you know, on average about twelve hundred dollars per person for a Hotel stay three or four nights. And we know generally those commissions are going to be about 15%. So it's a pretty fairly predictable business. Which, again, was appealing to me.
- [24:14]
Jared Benoff
So not. So we're going to unpack these numbers a little bit, but just Top Line is not only is a travel agency surviving in 2025, which may surprise some people, it's a great business. It's. It's a very high. It's a highly profitable business. So one point. So I think to really apples to apples, this with other businesses, it's really 1.3 million revenue business because we don't. Yeah. So the commissions that drop to your Top line, your top line is really 1.3 million. And then 950,000 is the SDE that goes to your father. And your mom was involved as well.
- [24:48]
Jack Benoff
She was. She was.
- [24:49]
Jared Benoff
Okay. So that. So they're splitting 950,000. So that's. What is that, 3, 350,000 in expenses, which is basically just people. And are the people, how are they, how are they compensated? And are they stateside? Are they. Are they offshore?
- [25:08]
Jack Benoff
So most people are stateside. We happen to have a woman in Cancun. She's. Well, she's amazing. We love her. But yeah, most people are primarily hourly. They'll earn commission if, you know, they book their own trips or let's say you have a wedding and the bride and groom come back to you a year later and say, hey, we want to go away for our anniversary, then, you know, the person who helped them would make commission on that. But most people are hourly and right now most people are stateside and.
- [25:37]
Jared Benoff
And so you have about 10 people.
- [25:39]
Will Smith
That manage all of these logistics.
- [25:40]
Jack Benoff
Yeah.
- [25:40]
Jared Benoff
Okay.
- [25:41]
Jack Benoff
Yeah. Typically the way it works is, you know, one person is assigned for each group. Each person will manage about 10. Around 10 groups per year because each group's going to be at a different life cycle. So, you know, one group might be just booked and they're under deposit versus another group might be further along and they're under final payment or submitting flights, things like that. And so ideally, you know, you have a steady workflow for each of the groups that you're managing.
- [26:02]
Jared Benoff
And you met you as one of your employees maybe managing sort of for. At any given time at various stages of their. Of their cycle.
- [26:10]
Jack Benoff
Yeah, just about.
- [26:11]
Jared Benoff
Yeah. Yeah. Okay. You don't have anybody on the ground at any of the destinations. So you're not managing any of the we'll pick you up from the airport stuff. You're just. Now you're Just booking? Essentially, yeah.
- [26:22]
Jack Benoff
Again, this is like very much a laptop business. We have calls with clients, emails with clients, and we work with local partners. So for, you know, let's take Will's wedding for example. If you're getting married in Cancun, you're going to land in Cancun and we're going to have arranged the transportation for you. So we'll have a local partner who will have pick you up. They'll have, you know, a sign with Will's wedding on it and you're going to get whisked away to the, to the hotel. And that's all taken care of. But we're not actually present at most of our events. Again, it's largely just behind the scenes taking care of all those logistics and administrative things to get everything squared away for them. But a destination wedding is a lot more complicated than an at home wedding. I always tell couples, like, if you're gonna get married in your hometown, you might go to your venue 8, 10, 12 times and you know what, inside and out because you visited so many times. But if you're getting married in Mexico or wherever, like you may actually not go to that venue at all up until three days before your wedding. And so they're putting a lot of trust in us. And so I take that really seriously. And we want to make sure we're buttoned up through the process to make sure all those little small details are taken care of for them.
- [27:27]
Jared Benoff
Yeah, yeah. And are you the kind of single throat to choke sort of thing? So if they have a problem on the ground, do they call you or do they go to the hotel or the transportation provider, the local whomever, it.
- [27:39]
Jack Benoff
Depends on like what the issue is. But there's a few different times in which, you know, they might need to contact the transportation if their flight chain, you know, flights are a mess right now. If your flight changes, it's sometimes easier to call the transportation company or they're at the resort already, you can just go talk to the guy in the lobby and say, hey, my flight changed. It's often much quicker to do that. Then send us an email. We send them an email and the guy's right there. So it just depends.
- [28:02]
Jared Benoff
Fantastic. And so given that this is a laptop business and it's logistically very complicated, but it is something that the barriers to entry are non existent other than your lead, your own, you know, the customers that you bring in. How do you, how, what is the moat of this business? Or how do you build a moat? I assume it's Brand. It's, it's referrals. I'm not sure that qualifies as moat.
- [28:30]
Jack Benoff
But please, it's a good question. That's something that I struggle with. And when I was thinking seriously about acquiring the business for my parents, I thought about that. You know, like I said, there's keyman risk. My dad was the face of the business. People generally booked because they talked to him. And there wasn't really mo. You know, there's. The space is interesting. There's like two or three large, large companies who planned us initial weddings and there's a bunch of small mom and pop companies who do this. And there's not really a moat. It's hard to say, you know, we can get X, Y and Z exclusive perks. Yeah, we have some of that, but that's not enough of a kicker for most people. And so the way that we like to think about, again, like this is more qualit than quantitative, is we've been doing this a lot longer than most people. We have a ton of experience and it's all about the relationships. Again, 80 something percent of couples that we work with never go to the resort before they actually get married. And so if they're trusting us with that process, you probably want to make sure that I've been to that resort or someone on my team has been to that resort and knows the wedding team, knows the venues, knows all the small, important details for wedding couples. And that takes a lot of time to learn because these things move quickly and they change often. And so we take pride in, you know, I was just down in cancer last week, going back down in a few weeks. Like it's important for us to be there with our partners and not everyone can do that or does do that. And I think that when we talk to couples and we talk about these things, that goes a long way and so look like, is it a, a sustainable mode? I don't know, but it's worked so far. And I think the more we can continue to showcase that and educate couples about the importance of that, the better off we'll be.
- [30:10]
Jared Benoff
Well, I, I don't think, I think most small businesses, most categories of business that show up on acquiring minds don't really have a moat. They differentiate basically on service, which is, which is kind of what, what you just described. And so, you know, we, we like to, we like to, you know, stress test a business and try to figure out where there might be mode. But realistically, it often just comes down to delivering better, better service than the next Guy.
- [30:34]
Jack Benoff
It's also the, the other challenge, again, like listening to your podcast a bunch. Sometimes it's a geographical. Again, we're not geographically constrained. Sometimes it's like, oh, we're the number one partner of this resort. And that's not the case. We work with about 35 to 50 different properties, generally speaking, in a given year. And so to your point, like, it's hard to define what that moat looks like. And the service aspect is so important. Again, like, a couple comes to us and then they're bringing 60 people and saying, hey, trust Jared with the decision we've made. And so it's important for us to, to deliver for not just our business, but for the couples really well.
- [31:10]
Jared Benoff
And I think that is one of the. Despite how compelling the numbers of this business are and the flexibility and the ability to travel, all the stuff that we're talking about, that does feel like one of the weaknesses of the business, where a single. I mean, you've got to get, you've got to get a thousand out of a thousand little decisions correct for every single client. Because if one of those little things goes wrong, you get angry. Customers, you know, they're only getting married once, we hope, and, you know, we all, we all understand this. Like, if what, there's one little hiccup in your travel plans, there's a ripple effect and it can throw a lot of things off and people get really mad really quick. So being under that pressure seems rather unpleasant.
- [31:54]
Jack Benoff
Respond, yes, it's tough. Like, there's no. Again, I come from the tech world where I'm working with Fortune 500 advertisers. I came from government before that, where I was working with senators, members of Congress. And so, like, I understood the pressure cooker. It's like you walk into a meeting with a senator and they're upset about their Twitter account being hacked or whatever it is, you know, whatever the thing is. Or you walk into a meeting with an ad agency and they're mad because, you know, their campaign was terrible, whatever it is. And so I'm used to that. But it's. In a lot of ways, it feels even more magnified when someone's wedding, you know, it could be the most important day in their, their life. And when they have 60 people who are there bringing, and you know, now their friends are upset, whatever, like, it happens. There's no way around this. And it's tough. It hurts. Like, I won't sugarcoat that. Like, every time I get a less than five star review, I feel like a little sting Inside and oftentimes it's things that are out of our control. You know, my, my parents and I always joke we'll get a four star review because the French shies at the resort were cold. And it's like that had nothing to do with us. We can't control that. And that really hurts. And I think it's, you know, partially like educating people what we do and where we sit in the process, but also understanding that people are people. And the more we can do to just make sure that we deliver upon these like champagne experiences and, and sort of surprise and delight people with the good. Hopefully any small hiccups along the way will be forgotten or you know, they're okay to look past them because look like I remember my wedding. Like things go wrong. It happens. Right, right. And, and that is certainly one of the downsides of this business is it's a people business and it's all about relationships and it's all about delivering service. And it's hard because we aren't the only piece in the supply chain. And so making sure that we nail as much as we can control and work with partners who can deliver upon that is really important.
- [33:44]
Jared Benoff
Yeah, it's got to be very frustrating to be held accountable for things that are completely outside of your control. You're, you're kind of face of this entire experience. Even if there's like 20 vendors involved.
- [33:54]
Will Smith
On the other hand.
- [33:55]
Jared Benoff
And so you know, you get dinged because of the cold fries, on the other hand, your competitors suffer the same dynamic. So, so, so if, if you're getting the occasional lost star for something out of your control, so too are your competitors. And so if you're held up next to your competitors, there's a level playing field, at least to the point about reviews that is where we would hope there would be some, some moat or some, some built in, built in value there. What does it look like? What did that look like? A 15 year old business in the YouTube videos.
- [34:24]
Jack Benoff
Yeah, I, I'll talk, I'll touch on the YouTube videos after. So something that honestly I was inspired by SMB, Twitter is, and a lot of the home service businesses was how important reviews are. We weren't asking for reviews. We didn't really think about that. It was kind of like we thank our couples after I turn home, send maybe a note to guests saying thanks for traveling with us, whatever. But we weren't concerned about reviews. In, in some ways it was like, well, we don't want people to see how many weddings we're doing. And we don't want people to give a reviews because again, we were afraid of the four star review because the french fries were colder, the view wasn't perfect or it rained, you know, all these things that aren't in our control.
- [34:58]
Jared Benoff
Yeah.
- [34:59]
Jack Benoff
And again, inspired by SMB, Twitter and all the home service business who are sharing how important reviews are for rankings and different things like that and just trust on online, I worked with my parents, I was like, look, we gotta double down on this. And so we built systems to ask people for reviews and to encourage people to leave reviews and, and in doing so would explain, hey, please review how we were in booking your room or arranging your transportation so it was more concrete and it wasn't just like how was your time at the resort? And over time, going back to your remote question, like that has become a moat. We have hundreds of five star reviews on Google, hundreds of five star reviews on the Knot and Wedding Wire. All these sites where wedding perspective, wedding couples look to, you know, see what this online business that, you know, they've never met before might be about. And so that has become a mo over time. And we're really proud of every review that we get because we, we whether good or bad, honestly, like the feedback is helpful and hearing from couples and seeing their pictures and any guests too. Like I love seeing guest reviews because it shows they had such an amazing time celebrating their friends and, and it means a lot. And so the reviews have definitely been a big focus for us over the last few years.
- [36:14]
Jared Benoff
I was just going to ask, so have you. It's been a big focus. Have you noticed the benefit of that? So as your, as your reviews across the Internet increased, you saw more leads come in?
- [36:24]
Jack Benoff
Absolutely. I mean I can see it on the Google business page. But I also talked to couples who say, oh, I saw you and I saw you have 200 five star reviews or whatever it is. And they mentioned that and how helpful that is that they did the research. Because every couple now, you know, they're scrolling Instagram, they're scrolling TikTok, they're looking online, they're looking on YouTube, like they're hitting all these different channels to make their decision. And it's a really thoughtful research process for a lot of people. And I think in a lot of ways our reviews may be the thing that pushes them over the edge when they're sort of debating between us and another competitor of well, these people clearly know what they're doing because they've got all these reviews. And we like to think we do but it's, it's helpful that, you know, so many of our clients over the years have also totally fed into that and sort of supported that, that we do know what we're doing, we do have the tools in place to help this all come to life, which is certainly helpful. So yeah, I mean we've definitely seen an increase in trust and probably has helped our lead flow as well.
- [37:25]
Jared Benoff
I'm getting the impression that the travel agency business industry might be a little bit behind on proactively asking for reviews.
- [37:32]
Jack Benoff
Yeah.
- [37:32]
Jared Benoff
Versus home services where it's like it's, it's table stakes at this point. You, you can't really differentiate on that. You have to have it to compete. Good reviews online.
- [37:40]
Jack Benoff
Yeah. And again, it's one of those things that for most, the average travel agency owner is probably in my parents demographic. You know, they're probably in their 50s or 60s. They've probably been doing this for 20 or 30 years. They probably get most of their leads through referrals and they're probably not in a specific niche. They're just sort of doing a little bit of everything. And so the things that again, like I go back to Twitter and X, like so many of the lessons I learned by just observing and being a part of the community were, you know, the average person would say, well, like what does an H Vac business have to do with a travel agency? All the lessons learned in getting reviews, if I apply them and no one else does, that's going to give us that edge. Yeah. And so that's been again, a huge help.
- [38:22]
Jared Benoff
Really cool. Well, thank you H vac business owners for helping Jared here.
- [38:28]
Jack Benoff
It's, it's so funny. It's like even to the point where I've considered doing some of the other H vac Ask or home service ask marketing things. So whether that's mailers or some of these more traditional marketing tactics, you know, I, I tested recently sending handwritten thank you notes to a group when they returned home and some other, again, marketing tactics that I've seen others do not in the travel space at all and just using it as inspiration to test. And again, I know that other people in the travel space aren't doing this. Yeah. And so if we can cut through and reach people, then it's, it's a massive win.
- [39:03]
Jared Benoff
Well, it is a win, Jared, and it's something that you should really run toward because as I understand the, you know this from, from kind of being in marketing essentially or selling marketing, that marketing is so competitive and so dynamic and the Best tactics are eventually competed away. We saw this in home services. You'll hear people talk about H Vac was essentially where travel is back in 2016. And there was a window there from like 2016 to 201819 where you could really leapfrog your competition if you were savvy online doing the best digital marketing, best practices. And that window has long since closed and it's now table stakes and it's highly competitive and, and lead cost is really high and everybody has good reviews. So. So any marketing tactics that you can employ, you should employ quickly because they're, they're, they're kind of by their nature transient. Yep. So pretty cool opportunity for you, the YouTube channel.
- [40:00]
Jack Benoff
Yes. So it's interesting again, one of these things that just happened by accident during COVID you know, everything shut down. As everyone remembers, travel was, was probably one of the worst hit industries and we had tons of weddings booked and my dad was getting calls left and right from couples and guests saying, well, what do I do? What's going to happen? What should I tell my friends and family? And he's like, I know maybe as much as you, maybe a tad more, but like I don't have the answers. And he got frustrated and he was sort of just sitting around like I'm just gonna record a video and answer some of these questions for people. He again, this is a 60 something year old guy who's been in this industry for a long time. He didn't have a YouTube channel, he wasn't a YouTuber. And he's like, I'm just gonna do it. And so he's sitting and he records these videos. He starts answering people's questions and it just takes off. It wasn't just the clients that he was sending the videos to. These videos were taking off. He was talking about, you know, what does this mean for my wedding in the future and what resorts are handling, you know, post Covid well and all these new things. And, and as his travel came back, his channel just took off and his organic YouTube channel become became probably our top source of leads over the course of a few years. Really, really just a dynamic way for him to educate people. And again, there was no selling. He actually started under not even the Vacation Ease brand, which is the name of our company. He started under this Desta Wed Tips brand because I don't really want it to be affiliated. I just want to help people who don't know what to do and have a bunch of questions. And he would mention our company like once in each video, maybe Once and it wasn't even in the bio or anything and it took off. And again, I think it's because no one in this space is doing stuff like this to just educate people and arm them with information. And he was serving that need. And so the YouTube channel he wound up posting and like once a week he'd record and edit his videos himself. I mean it's super impressive. Like I'm, I'm always in awe of both my parents and it's really, really cool what he's been able to do by creating a YouTube chann. And like by the standards of a YouTuber, having 3,4000 subscribers isn't huge. But when you're talking quality of subscribers and how valuable you know, one wedding is to us, getting a few leads a week from the YouTube channel is massive. And so it's been cool to see the growth of that channel as a, as a organic marketing tool for us.
- [42:25]
Jared Benoff
Well, the last point you made there is so it's such a good lesson in content marketing because when you say it took off, you know, we think of a YouTube channel that takes off as something that goes viral and we think, we think in the millions now because TikTok and the stories we hear about TikTok are those are the types of numbers we hear. This channel, I'm looking at it right now, has four and a half thousand subscribers. Yeah, this is a tiny channel by totally, you know, mainstream standards. But it's all about, you know, it's, it's a cliche now in Internet, but in Internet marketing, but it's all about that long tail. And if you are in a long tail where there isn't already a kind of a few authoritative voices and you're crucially, your average ticket price is really high. It just, it makes sense all day long. I mean like, you know, he just makes a few sales off of these and it's, it's can be really a game changer but you know, and these I'm looking at the most recent looks like he's still doing it. I mean the most recent video is seven days ago. He loves these have a few hundred, you know, a few hundred views. Like nothing huge, but such a, such a good example of long tail content marketing.
- [43:33]
Will Smith
And, and by the way too at.
- [43:35]
Jared Benoff
Least like the, the intro video or the one that first comes up when you visit the channel, it's not at all overly produced.
- [43:42]
Will Smith
He's not speaking in, I think he has a lapel mic.
- [43:45]
Jack Benoff
Yeah.
- [43:45]
Jared Benoff
But it's not like it's super high quality or super well produced. It's very human and it's exactly what you said. It's like your dad just kind of.
- [43:52]
Will Smith
Turned on the mic and started talking.
- [43:54]
Jared Benoff
And it's really cool. It's, it's really. And it's nice to hear and realize that like, that sort of content marketing for a small business still works in 2025. Because this is like what Gary Vee has been talking about for 15 years, still opportunities to do it.
- [44:09]
Jack Benoff
It's so interesting. Like, I, again, my career up until this point was working with Fortune 500 advertisers who, you know, do spend millions of dollars on highly produced content and will think for a year about what their next video will look like. And here's my dad in the basement shooting footage on, you know, a camera he bought on Amazon. And it's, you know, resulting in tons of revenue for him. And I was, at first we were like, this is crazy. This isn't going to work. And then, you know, I start doing calls with prospective couples and they, they'll say, hey, I just watched 7 hours of videos from Jack. I know. Well, we, I laughed about it too. And then they go, I know exactly what resort I want. I know when I want to get married and all that. So he was not only taking them through the funnel through his videos, but they were so much more, they were so much better informed. And it was remark. I mean, the funniest story is he was sitting at a resort one time this a few years ago, and he's sitting there and a woman's kind of looking at him and he, he, my mom and him notice it, and they're like, this is weird. Like, why is she looking at us? Like, do we know them? And she comes up and she says, hey, are you Jack? He's like, yeah, do I know you? She said, oh, I watched your YouTube videos. I'm actually down here checking out the resorts to potentially get married here.
- [45:21]
Jared Benoff
Oh, wow.
- [45:22]
Jack Benoff
And like, she recognized. And again, like, this is. He's not an influencer by any means, but it's, it's remarkable the, to your point, like the, the power of these smaller channels and the watch time. Again, like, my world, I was always working with clients were like, we need, you know, a CPM of X and Y amount of video views. And if a video gets 100 views, it could be like the best video of that month. Because those hundred people could be prospective couples. And so people always sort of poo poo. B2C versus B2B. But, you know, in this sense the B2C having a high quality audience and talking to the right people with the right message, it resonates. I mean, it's authentic, it's real, it's human. And that's what we want. When we talk to couples again, we want to build that trust. And the way to do that isn't with highly produced content. It's to be real and to show them the blemishes of resorts and to show them, you know, that, that this won't be a perfect planning process and, you know, maybe this thing won't be exactly how you envision it, but like we're going to help you through that and we're there with you to make it as great and as stress free as it can be. And we really try and hit home that ethos and philosophy.
- [46:28]
Will Smith
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- [47:40]
Jared Benoff
Turn to the theme of buying, acquiring a business from your parent, there's a lot there anything more to say about travel agencies as a category? Are they, are they, are they enduring? I mean, we've already talked about how the Internet killed kind of the mainstream undifferentiated travel agency for these niche travel agencies like yours. Are they enduring? If the, you know, it's kind of like, I guess if the Internet hasn't killed it yet, it's probably not going to. Are they for sale? Are, is this, is this something that people should look at? Do you see them on Biz by Sell when you were going through your tire kicking phase? What can you, what can you share broadly about this category of business? For the listener?
- [48:24]
Jack Benoff
I think it's undoubtable that, that travel agencies as we probably knew them, you know, many years ago have disappeared or will potentially disappear. I think the ones that do well are the ones the tr again this is sort of the traditional model. The ones that still do well are geographically constrained. So they're the travel agency in town and you know, as the population ages, people want to go have that hand to hand relationship and they want to go into a store, they want to call the guy down the street who they know through the community. And so I think there will be a place for those. And those tend to be sort of the will help you with any type of travel business for that town. So I think those will survive because people still want that human touch. I think the online travel agencies or OTAs, you know, the big ones being obviously like Expedia and some of the other brand names that we all know. You know, if you're trying to compete against them, it's just a massive uphill battle. Those companies have billions of dollars of marketing budgets every year and you can't compete against that if you don't have the moat, you don't have the marketing budget. Like it's just so hard. We're seeing some success with it. Like there are again mom and pop or individuals who are coming out. You know, there's a lot of people actually in sort of a younger demographic who are saying, well I'm going to do it on TikTok and they're going to blow up on TikTok and then they're going to turn that into sort of a one or two person show travel agency. I think there's some success. I don't know how durable that is, but people are having some success. And then the other end of the spectrum I think would be companies like ours that sort of niche down and become an expert on one specific type of travel. For us, you know, that's niche group travel. For some of your other guests that's been group tours to Italy, different things like that. And so I think those will be good. And again, another thing I learned through SMB Twitter is like find the business that can't be Amazon away, that can't be commoditized. And it's really, really hard to plan a destination wedding. It's impossible, let's be honest, through chat GPT like there's just not a way right now. And maybe, you know, in five years I come back and I go, oh crap, I was so wrong about this. But I really don't see a way in you can plan this through an AI tool right now or through Amazon for example. And so I think the industry has evolved and again like there's probably those traditional players that will try and survive as long as possible. But the industry as we knew it 20 years ago is not the same. But there is this whole new evolution of the industry that's super appealing and I don't think it's the most acquisitive space. I think partially because of some of the issues that we talked about earlier. But there are.
- [50:47]
Jared Benoff
What issues are those which I think.
- [50:49]
Jack Benoff
That it's largely project based. I think that it's hard to compete with the big OTAs that there's a lot of key man risk. You know, it might be Will's travel agency and everyone just wants to talk to Will and those people are kind of just retiring and winding down or they're just selling it to, you know, the guy next door and the next town over, whatever it is. So it's not, you know, if you look on biz by selling and I've looked over the years like there's maybe one or two for sale at a given time and a lot of them skew again more towards the group niche which obviously is a theme that we're. We're are coming to of groups is kind of where it's at because it's, it's more scalable, it's more predictable and you avoid some of those issues of competition. So it's not something that's just filled on biz by sell. We're just going to see hundreds of these for sale. It's just not how it is in this industry.
- [51:38]
Jared Benoff
Yeah. And frankly maybe that's a good thing. So for the listener who is finds this type of business appealing, they're could be. If they're not all over biz by sell it probably means that, you know, you could reach out, you could do a lot of proprietary outreach and these owners are not hearing from searchers or other people who want to buy their businesses and there could be great opportunity. Your point about the group travel and that's really where this niche lives and thrives or that's where travel agencies, smaller travel agencies live and thrive is such a good one. It's, it's, it's, it's a benefit to you. It's also, it's also where the type of travel where the customer is really going to look to have a consultant is the word I keep. I haven't. You haven't used that word. I keep using that word. But that's kind of what it feels like.
- [52:25]
Jack Benoff
100.
- [52:25]
Jared Benoff
It's like you're kind of your Personal your concierge experience. Even if chat GPT gets to the point, AI gets to the point where it could do an entire plan for your destination wedding. You could imagine people just not wanting that. They just want to deal with a human for an experience like that and a purchase that large. So it does, it does seem pretty well protected against AI. And another point about the group agencies you just. Or excuse me, group travel and how that's kind of the niche where travel agencies work. You mentioned Shell, Shell Zhang of Not as Italy. So a couple months ago we, we aired her interview. Shell also bought a travel agency and we had a somewhat similar conversation to the one you and I are having now. Jared and her not as Italy. Does group travel to Italy. One thing in her case that I think is also a trend that you haven't mentioned is that her demographic, her target demographic trends older.
- [53:22]
Jack Benoff
Yeah.
- [53:22]
Jared Benoff
So it's kind of the, the retiree folks who want to do group travel and don't want to deal with pointing and clicking and maybe maybe want the group experience because they want to meet other people. That's kind of. And now in destination weddings that's going to be less the case. So that's maybe not your. But I think that is another trend to call out. That's kind of where she plays that, that, that age group. What. One other trend that you touched on that, that I, I just don't want to leave hanging.
- [53:47]
Will Smith
So.
- [53:47]
Jared Benoff
So there are other travel agencies that thrive that are like the local town travel agency. And so, so what are they retail. Like they have a retail presence and everybody like walks in and does their travel that way. Okay.
- [54:01]
Jack Benoff
Most of them have been around for a long time, maybe second or third generation even or they're, you know, a franchise. And again, it, this probably skews towards an older demographic and they're, they're going in, they're talking to a person, they're saying, hey, I want to go to France this summer. What. What can you help me with? And so again, I think that similar to Notice of Italy, like that's probably marketed towards an older demographic who they know their person in the store and they go and they talk to them and they help arrange the travel.
- [54:29]
Jared Benoff
Yeah, fascinating. I mean, I feel like I haven't seen.
- [54:34]
Jack Benoff
They're disappearing, but yeah, they're still out there. They're still out there. Okay.
- [54:39]
Jared Benoff
And also we're talking about how this, the business model still works and is. Is protected from the future. But in terms of upside, you've already touched on it a little bit but just flesh that out for us. You. You see the levers to pull. You see, market more marketing to do. Tell us more about how you could get this business from, you know, 1.3 in top line to 5.
- [54:59]
Jack Benoff
Yeah.
- [54:59]
Jared Benoff
And assuming you do want to grow the big enterprise, dad was resisting. Okay. All right.
- [55:04]
Jack Benoff
So, again, like, I'm not imagining a world in which we're the number one in the space. Like, that's not, you know, maybe that's bad for me to say, but I'm not envisioning hundreds of people on our team. I think if we can get to 5 million in top line, that would be a great place to be. So the. The levers one is people. Again, if people are biggest expense, how do we look at that to. To become more efficient? One of the ways is by working with more global talent. I've done this a little bit already, but again, talent isn't necessarily geographically constrained, and our business isn't either. So we should be thinking about that more. More holistically. So that's the first. Second would be marketing. Again, like, the YouTube channel is fully organic. We've tested some paid ads over the years, but not really in a meaningful way. We just brought on a social. Organic. Social agency to help with some organic social. We don't really do a ton of partnership marketing or anything like that. So all these different levers that we can pull are just sitting there and waiting. So those are probably the two big things. Again, if I look at the P and L, the number one expense is people. So I'm going right there first, and then the biggest gap is marketing. So that's sort of number two for me.
- [56:13]
Jared Benoff
I was just gonna say exciting. Jared. I love the business, and I love the opportunity. And of course, we all love to hear about a business that. I mean, we shouldn't say that. Your dad hasn't been marketing because he has this amazing YouTube channel, and you guys got savvy about reviews a few years ago. So it's not like none of the levers have been pulled, but it sounds like there's still so many more to pull, and that's always just such an enticing prospect.
- [56:32]
Jack Benoff
Something crazy I'll share is again, you. We talked about the math earlier in the show, but in a given year, about a hundred groups. Each group's about 60 people. You're talking 6,000 people who we help plan their travel every year. We have their email address. They've paid. We've communicated with them a few times. They return home. We generally don't Speak to them ever again after we welcome them home. We, for the longest time, haven't leveraged our email list. And again, like, if I think back to what works in other, other industries, we should be talking to these people every month, at least recommending other places that they can travel. You know, if a new resort just opened up down the street of where they went last time, if, hey, we know that, you know, you're in a certain demographic, maybe you want to go on a golf trip, or maybe you want to go to Italy, or maybe you want to do a river cruise. You know, all these other things that we are also fairly good at and have team members who know this stuff, but we don't make that request and we don't showcase that. And this is low hanging fruit, right? These are the things that, coming from a digital marketing and a sales background, I look at this, I go, okay, so we have 6,000 people each year just organically being added to our network that we're talking to regularly. And then we just cut it off and that's it. I'm not even talking a paid acquisition channel. I'm talking people who are already in our network. And so there's little things like this that it. I look at this and I'm, I'm sort of like, all right, let's, let's get going. Sort of getting the systems in place, make sure we have everything ready to go and slowly testing that out.
- [57:53]
Jared Benoff
And. And you would want to be slow there because of all the 60 people who go on a trip, only a few of them, or maybe even two, the principals, the husband and wife, let's say in the case of a wedding, are the ones that interacted with, with you guys, right? No.
- [58:08]
Jack Benoff
So actually the other 58 aren't gonna know.
- [58:09]
Jared Benoff
Or they are.
- [58:10]
Jack Benoff
They all. Yeah. So we interact with every single guest. We help them with their travel, we help them with their transportation. So we probably email them over the course of the life cycle, probably six, seven times.
- [58:19]
Jared Benoff
Oh, great.
- [58:20]
Jack Benoff
Yeah. So, no, it's not just a couple. It's. It's all the guests. So it's everyone. So, yeah, we have that relationship already. And so they should be a little familiar with us. They may not think of us in the vein of, you know, what their next trip looks like, but it's our job to educate them of, you know, this is also what we can do for you down the road.
- [58:37]
Jared Benoff
Cool. Really? Yeah. Love, love that. What a list. Okay, Jared, how does one buy a business from one's parents? Do we need more context? Here. Do we, do we, did we already get enough of the plot as to like how it zeroed in? You guys kind of were zeroing in on this possibility, joke becomes reality sort of thing.
- [59:03]
Jack Benoff
Pick.
- [59:04]
Jared Benoff
Pick us up. Where, where do we start? Here.
- [59:06]
Jack Benoff
Yeah. So again, as we were saying earlier, it started as a joke, became closer reality. I had done, again, I'd done some research on what reasonable multiples could look like. I explained to my dad what some of the risks are and you know, him being key man, things like that. We talked about what deal terms and a purchase price could look like. I won't sugarcoat it. Like I, I was very lucky in the purchase price he gave me or he wanted. And again, this is pro and con of, of buying a business from your parents is. It was due diligence because I knew the, the insides of the business. I'd seen I'm the one who built the tracker, I'm the one who sort of monitors the revenues. Like I knew a lot of the, the nuances. And so there wasn't a qov, there wasn't some of the other more traditional due diligence things because I already knew a lot of that, that. And so, yeah, pro, again, pro and con for sure. But the.
- [60:03]
Jared Benoff
What's the con? That sounds nothing but good.
- [60:06]
Jack Benoff
The con is maybe I had some tunnel vision, right? Like maybe because I've already knew the business, that I could be coming in blind to some things that I overlook or that someone coming from the outside more objectively might look and they go, oh my gosh, that's a huge red flag. Granted, that's where ideally, like the bank that I worked with, I worked with Heather from Visor Capital, like she would have called these things out. So, you know, there's other things along the road that hopefully would have come to come to light, but I wanted to go in as open minded as possible to understand the pros and cons of this business and what potential risks. You know, if we go from 100 groups a year to 30, what does that look like? If we go from 100 to 200, what does that look like? And I really wanted to be clear minded and open minded about what that could look like and honestly talk to my dad about it because again, he knows this business way better than me and I wanted to make sure he was aware that, hey, I'm not just asking for a discount, I'm asking for, you know, a reasonable valuation on what this business looks like if he steps away or when he steps away and I take over things.
- [61:04]
Will Smith
Well, aside from.
- [61:06]
Jared Benoff
The fact that you didn't have to spend money on a qov, you could save some, some serious outlay that most people shouldn't when they're going through an acquisition, you could trust the seller. And I just had an interview, which will air a couple weeks before yours, with Jed Morris, whose acquisitions went sideways and lost it all. Terrible story. And he's since connected with a lot of other acquisition entrepreneurs who had bad outcomes and he's probably a couple dozen of them and he's tallied some data. It's not statistically significant, but it's enough to, to, to draw some conclusions. The majority of these stories gone wrong, more so more than 50% of them are due to a fraudulent or unethical seller. I was at MIT's ETA conference last week and on a panel about this very topic. And I think in three of the four cases of the panelists who's had, who had had terrible experiences with their acquisitions, it was about a bad seller. So this really is reason number one why acquisitions fail. Of course there are other reasons, but, and so you, and it's just very, very hard to, to know in advance. Of course if you just have a totally shady seller, usually you'd walk away anyway. But sometimes, sometimes you just, you can't tell until you get inside the business and then it's too late. So you didn't have that. You know, that was the biggest risk of all, was a non risk for you.
- [62:41]
Jack Benoff
Yeah. And again that's why I feel so lucky and grateful because I, I've known, I've known the seller for 30 something years and we have a great relationship and he loves me and I love him. Like it's, it's, it's again like I, I, I'm joking or half joking, but like it's, it's, it's such an important thing. And again that mattered. When I was thinking through a few years ago, like should I acquire my parents business? That was one of those themes that came to light as I was doing more research that I need to trust the seller. And I, I, I felt most comfortable going down that road again. Like no acquisition is perfect. And there's things where now that I'm in the driver's team, like oh my gosh, I gotta fix this or I gotta pick this thing up or my dad did it one way and I'm like, I totally want to do it a different way and that's normal. But knowing that I can trust him and, and frankly he has my best interest in mind, he's carrying a seller note and he is still happy to jump on call. He's like, hey, if you want me to talk to that couple, I will. And you know, if you want me to still make YouTube videos, like, I will. So those things go. It's hard to quantify them, but they're invaluable. And so I feel, I felt really confident going in knowing that that was the case.
- [63:47]
Jared Benoff
Yeah. Yeah. Well, I want to continue unpacking this because, because those are all the pros now that there are going to be some cons about, for example, stepping on the toes or changing the way the seller did it. You know, if it's, if it's dear old dad, it might be even more awkward than it can sometimes be when the seller's involved.
- [64:04]
Jack Benoff
Solved.
- [64:05]
Jared Benoff
We'll get there. But first, the numbers. You mentioned that it was a generous to you, a beneficial to you purchase price. Can you shed more light?
- [64:13]
Jack Benoff
Yeah. So 2024 SDE was right around a million. And so the agreement was 2x SDE, so purchased it for $2 million. Part of that agreement was that he would carry a 10 seller note. I do 10 equity. And the remaining like 1.7 ish would be an SBA loan. So it did structure it in a more traditional way. But again, that multiple was certainly very reasonable in my favor.
- [64:39]
Jared Benoff
And why do you think your dad, Is it because it was his son that he gave you a good price? Because you probably would have bought it for. Yeah, I guess.
- [64:48]
Jack Benoff
Yeah, that's obvious. The obvious answer is yes, I think.
- [64:51]
Jared Benoff
But, but even, but, but Jared, even 3x would have been, you know, a good price sort of thing.
- [64:55]
Jack Benoff
Totally. And again, when we were going through the diligence phase and working with the bank and we stress tested it, you know, three, three and a half still would have worked given where the, the margins are in this business. Right, right. So, yeah. And people always say, oh, you want the terms, not the price. And in this case, I think because of how the business is, he, he named the price. And I sort of said, okay, that's fine. I wasn't about to roll up my sleeves and start arguing with him because how the business is structured and where the revenue is now, it's something that I'm very comfortable with and feel like there's a path to growth. So, yeah, the obvious answer is like, it's largely because the familial relationship and I recognize, like, that is not the norm. Not everyone acquiring a business has that opportunity.
- [65:39]
Jared Benoff
Right.
- [65:40]
Will Smith
No, of course.
- [65:41]
Jared Benoff
But, but, and you understand and it's great. And this is, this is where we're all trying to build generational wealth. And, and this is, you know, the, the discount that you got on this business is kind of part of that and that's a wonderful thing. And I, I, I, I suspect and hope that your father feels a lot of gratification to be able to do that. The so the way it came to that price, there was no negotiation. He came to you with a price and you said yes, effectively. Yeah. Just curious because in other words, what I'm trying to get at is like, how does one negotiate against dad? And there wasn't much negotiation.
- [66:17]
Jack Benoff
You know, I would, I would rib him. It's so funny. Again, not a normal situation, but we'd be like standing in the kitchen of my childhood home and he's like, oh, I could just go sell this for 4x the private equity. And I'm like, no, dad, like you don't understand. Like if you walk away from the business, it doll disappears and you know, there's no marketing, there's no managers. Like all these things that, you know, again, would be more traditionally looked upon as a massive negative. And he's like, I don't care, I'll just go sell it to someone else. And again, like it was in just and on both of our sides. But the negotiating was, was largely like he named his price and this was before he said this three years ago. He said, he said whatever the 2024 SD. He didn't call it that. Whatever I take home in 2024, just 2x that. And so when we sort of went down that road, I didn't know what that would look like, but that's where we netted out on things. But yeah, the negotiation was, was fairly non existent again. And I think largely because I had done the research and, and because of your podcast and some of the other podcasts that I've listened to and the, the SMB community. Like, like I knew that it was a multiple in which there was room to be stress test and, and room for me to feel more comfortable.
- [67:37]
Jared Benoff
Yeah. You mean the low multiple meant that you or you already having a lot of room there.
- [67:41]
Jack Benoff
Yeah.
- [67:42]
Jared Benoff
No reason to squeeze.
- [67:43]
Will Smith
Right.
- [67:45]
Jared Benoff
You know, I'm gonna, I'm gonna talk out of the other side of my mouth here. Not sure because so on the one hand you got a great deal because it's dad.
- [67:52]
Will Smith
On the other hand there, there are.
- [67:53]
Jared Benoff
Probably some people who are like, well.
- [67:55]
Will Smith
You should have just given you the.
- [67:56]
Jared Benoff
Business business or he should have 100 seller financed seller finance. Not the cult, not my perspective and not the culture of my family. Not the way. But you can imagine that there are voices out there who are like, well, why didn't he just give it to you, you know, you know, inherit the business as an inheritance.
- [68:12]
Jack Benoff
Yeah.
- [68:12]
Jared Benoff
Now you've also mentioned you have siblings, so there's maybe that's a function slash, he, he just shouldn't do it. Anyway, it's not my. But to, to those people, you would.
- [68:21]
Jack Benoff
Say, look, I don't, I don't know exactly what's in my parents minds at any given point, but I, if, if I'm thinking about it. And again, knowing the seller for a long time, he worked hard. Like he built this business over many years. He took many angry, a phone call from a client. He had to figure these things out himself. And so why would he just hand over the keys to me and like, why am I deserving of just being handed, you know, this business that exactly on the market would be probably a three, three and a half million dollar business. Like he, that's his money. He earned that. Exactly. I would feel uncomfortable frankly if he just handed me the keys. I, knowing I have. And you mentioned the larger seller and that was the one point where I tried to negotiate with him a little bit, saying, hey, can you carry a larger note? And in a way I'm grateful. Obviously I'd be appreciative if it was a larger note. But I have this SBA loan, which is terrifying, don't get me wrong. But it makes me feel an additional layer of responsibility to help carry on their legacy and what they've built and to make sure it is sustainable because, you know, the government will come after me. And so I'm, in a way, I'm grateful. Again, this is maybe a little strange, but like, I'm grateful that it's structured in like the traditional way, even though the multiple is lower and whatnot, because I feel that the responsibility does weigh heavy on me, that I do want to make sure that I, you know, make my parents proud and can continue what they've built. And I wouldn't have expected him just to hand me the keys. And, and that's not the way I was raised and that's not the way that I would want, you know, in the future. Maybe if I, if my kids want this, whatever. Like, it's just not in my ethos really.
- [70:04]
Jared Benoff
Yeah, mine either. Maybe I overestimate how many people out there are, would, would think that because I'm, I'm with you I wouldn't think that for. For a second. Second, but we just hear about inherited businesses. Yeah. And maybe those. Maybe when we hear that, we shouldn't assume that there was no transaction. Maybe there was some. Some kind of transaction at a discount like yours was structured.
- [70:26]
Jack Benoff
Totally.
- [70:26]
Jared Benoff
Who knows? But very interesting. And to the point of the siblings, there was no inkling by them that they would. No. Okay.
- [70:33]
Jack Benoff
No. My brother runs his own business. My sister's a rabbi. So they're. Everyone's doing their own thing. Thing.
- [70:39]
Jared Benoff
They're taking. They're spoken for.
- [70:40]
Jack Benoff
Yeah.
- [70:41]
Jared Benoff
Okay.
- [70:42]
Jack Benoff
We're.
- [70:42]
Jared Benoff
We're gonna start wrapping up here. Jared, fascinating.
- [70:45]
Will Smith
The.
- [70:46]
Jared Benoff
But a couple more mechanics of the deal itself. You mentioned using Heather Anderson, Advisor, who is a loan broker. How did you choose to use an SBA loan broker as opposed to going directly to a bank? Give us a little bit of that experience.
- [70:58]
Jack Benoff
It all comes back. I feel like I'm just doing an advertisement for my previous employer. I met her on Twitter. I think I had. She had tweeted, you know, many years ago, like, I'm locked out of my account. Can anyone help? And I was following her. I was like, hey, I can. I can help you out. And then we just wound up talking a few times over the last few years. And then when it came time to purchase this business, I again, I'd seen her content, I heard her on podcast, we had talked, and so I, I reached out and she was amazing. She helped me through the process. She helped evaluate different banks and really helped me understand, again, I don't come from a financial background. I've worked in like, marketing and sales and social media. And so she helped me understand some of these mechanics of the process and what a deal looks like. So I really. It wasn't so much like using a loan broker or not. It was like, I want to work with Heather. And that was kind of what it came down to.
- [71:44]
Will Smith
And, And.
- [71:44]
Jared Benoff
But when you reflect back, if you can, if you can decouple Heather from working with a loan broker, that question. Working with a loan broker and having somebody on, you know, on your behalf, kind of reach out to the banks and try to find the right deal bank fit for you. I'm not trying to, I'm not trying to spoon feed this to you, but did you feel there was. There was value to that 100 proposition?
- [72:09]
Jack Benoff
I wouldn't have known where to start. I mean, again, like, you hear the, the popular banks who are marketing whatever, but being handed term sheets and being explained, you know, this is the pro of this. This is the con of this. We should wait for this other bank for this reason. She's been through it before. Again, it's the same reason why people trust us to plan their travel. I trust that said a loan broker, because this is what they do. And so it's, it's. I'm, I'm always okay paying for. And in this case, you don't even pay the loan broker. I always prefer to have the expert on my side and her being able to navigate that process. I've never been through this before, and so why should I feel confident that I can do this myself? When she's seen this, you know, hundreds, thousands of times.
- [72:47]
Jared Benoff
Yeah. Yep.
- [72:49]
Jack Benoff
So, yeah, great. Putting a fine bone. I would certainly recommend it to anyone. You don't pay any extra for it. So it's. It's definitely, definitely recommended.
- [72:57]
Jared Benoff
Actually, this was something else I wanted to touch on earlier. Because you bought a business from dad and mom, is there more awkwardness in terms of doing things differently?
- [73:08]
Jack Benoff
I don't think so, no. They're very understanding that, you know, they did their things their way and I'm going to do things my way. And again, like, I'm. With any seller, you trust what they have to say and, and you who. It's their experience. Right. So the things that they built worked for them, and the things that I'm going to build are going to work for me. And I think they're very understanding that some things are going to change. And even if they're. They have some limited involvement, like, they are okay with that because again, they've sold to me and, and they're okay with that. But, yeah, I mean, there's. There's a little bit of awkwardness of, you know, thinking about some things that they did. I'm like, I don't really want to do that that same way, or I want to tweak that. But again, I, I try to be reasonable and thoughtful about it and take. And try to understand. You know, again, I think back to some of the conversations on your podcast or other podcasts and online, and I think about how some people say, oh, you just sprinkle in marketing or just add AI or whatever it is, or just, you know, add offshore talent, whatever it is. And oftentimes it's not that simple. And the reason a seller had a thing was because it worked. And because they've done it for 10, 15, 20 years and they know that thing works for that reason. So it's helpful to understand why it is that way and then figure out, okay, Is, is. Does that actually make sense or should we find a different path? For example, the CRM tool we use looks like it's from 1999. And for a long time my dad and I have talked about we should switch and all these other things. And it's like, well, the cost of it's super low. It does the job. It's just an ugly ui. Again, I come from a tech world, so I'm like, yeah, but it could be so much more beautiful and work so much faster. And it's like, but it works and it's not a huge line item on the P and L and it does the trick. And so if it's ugly, it's. That's kind of okay for right now. That's not my number one priority. And so things like that, you know, there's no awkwardness. And it's helpful for me to know the background and the context of these things so that I can have better informed decisions on, like, the systems and things I do want to change.
- [75:00]
Jared Benoff
Fantastic. Jared, anything that you wanted to say about your story that we didn't get to.
- [75:05]
Jack Benoff
No. Thank you for having me on. Thanks for letting me share my story. I'm super excited about the travel space. I think one of the reasons I originally reached out to you is I think there's a lot of misnomers about the travel industry and travel agencies. And I, I love talking to people who are in this space and, and shedding light on, you know, actually travel is a really cool space and there's a lot of innovation that could be going on and maybe isn't yet. And I'm just excited to, to share that journey.
- [75:32]
Jared Benoff
Well, just to. To repeat, we had Shellza a couple months ago, so we've got now got you and Shell two recent stories of travel agency acquisitions. And then you introduced me to somebody else who may come on later who also bought a travel agency. Different actually with retail, so a different model, but similarities, group travel. So it's definitely, there's definitely a changing of the guard in this industry. And of course, it's a fun industry if you can, if you can deal with the pressure of. Of delivery, bring perfect experiences or near perfect experiences to your customers. Who doesn't like the idea of being able to, you know, go to Italy and Cancun on the company's dime or have that actually be your job. Good stuff, Jared. And so in terms of people reaching out, we'll include your LinkedIn. But you have also agreed to come to a live Q and A with listeners to this episode. So we will have promoted the exact date and time of that that in the introduction to this episode and in the outro and in the show notes. So that'll be a lot of fun listeners. If you want to come ask Jared a question and over zoom, we'll be. We'll be hosting him to do that. Thank you for saying yes to that, Jared. Any other way that they should contact you? LinkedIn Live?
- [76:51]
Jack Benoff
Q A?
- [76:52]
Jared Benoff
Twitter, I guess.
- [76:52]
Jack Benoff
Yeah.
- [76:53]
Jared Benoff
Are you still active?
- [76:54]
Jack Benoff
Yeah, I'm still, you know, I'm a lurker for sure. I don't post a lot, but my handle is Jay Ben Off. Um, so just my first initial, last name and yeah, I'm on there. Feel free to DM me. It's how I made connections with a lot of people in the community. So happy to chat with people from there.
- [77:06]
Jared Benoff
The name of the business is Vacation Ease. E E Z E. That's correct. All one word. Vacation.
- [77:13]
Jack Benoff
Yep.
- [77:13]
Jared Benoff
Got it.
- [77:14]
Jack Benoff
Yeah.
- [77:15]
Jared Benoff
Jared Benoff, congratulations on a really neat business. Great acquisition, Great multiple. What a story. Thank you for sharing all the detail with us.
- [77:22]
Jack Benoff
Thanks for having me. Will appreciate it.
- [77:23]
Will Smith
Hope you enjoyed that that interview. Don't forget to subscribe to the Acquiring Minds newsletter. We send an email for every episode with an introduction to the interview, a link to the video version on YouTube, and soon, key takeaways, numbers and more essentials from the interview. For those of you who don't have time to listen or watch it, subscribe at Acquiring Minds Co. You'll also find.
- [77:49]
Jared Benoff
All our webinars there on the website.
- [77:52]
Will Smith
Both those we have coming up and recordings of past webinars. At this point, There are over 30 webinar recordings, a wealth of information on all the technical nitty gritty of buying.
- [78:04]
Jared Benoff
A business Acquiring Minds copy.