Introduction
In this Founder Success Story, Jared Benoff shares his journey of how to buy travel agency business specializing in destination weddings. After nine-and-a-half years at Twitter working with Fortune 500 advertisers, Jared acquired his parents’ 15-year-old travel agency business, Vacation Ease. Today, the agency books about $8 million in gross revenue with approximately $1.3 million in commissions, and Jared sees a clear path to scaling it to $5 million in top-line revenue.
Founder Success Story QnA
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 – and second buying a business from your parents. Let’s get into it. I think the Story begins with your parents being entrepreneurial as you grew up?
Yes that’s right. I grew up in an entrepreneurial household and my friends roasted me for a long time that I would have to submit invoices and P&Ls during college to my parents for them to send me money each semester. But that was the mindset I always thought that was normal. One of the things my dad said to me when I was pursuing a career post-grad: ‘Just don’t get a government job.’ He said that somewhat facetiously, and what did I go and do? I went into public service for a little bit, I adored it, and I learned a ton working in the federal government.
Great, let’s unpack some of that. Nine and a half years of Twitter – from what year to what year?
From 2015 to 2024. To the end of 2024, so three months early 2025. Yes, I was there during the Elon acquisition. I was on the sales side based in New York City, selling to Fortune 500 advertisers, selling them advertising.
Your exposure to ETA was via SMB Twitter while you were working in ad sales at Twitter?
Ad sales. We used to joke with our clients that so much of our job is living on the platform, experiencing the content, seeing what people are saying. During the early days of COVID when SMB Twitter really blew up, I found myself gravitating towards that community. I’d reach out to people saying ‘Hey, I’m curious about what you’re doing here, tell me about your story and let’s chat.’ I found myself going down these rabbit holes of talking to different business owners, and I fell in love with it.
Okay Jared, returning to the plot – you say to yourself ‘I’m not going to buy some blue collar business that’s just not me.’ You’ve grown up with computers, been in tech in New York. Why was your parents’ travel agency business a good candidate beyond it not being a blue collar trades business?
That’s fair to invert the question – why was it a bad candidate? It’s largely project-based, there was a lot of keyman risk with my dad running the show, long sales cycles – things that in the traditional ETA community would make people say this business isn’t great. But for me, I love the travel industry, I like the lifestyle it allows, I love the interaction with people. These things that might not be attractive to a normal acquirer I love because I grew up around it. I saw the future-looking arbitrage opportunities – I knew what was working for them, I saw how it was working, and I knew with some fine-tuning, different systems, and marketing, I had a plan to see through the next 10-20 years.
They started this as almost a hobby to expense their own travel. They identified destination weddings as a niche – why was this such a smart move?
I don’t think they intended it to become a business. My dad is a super entrepreneur – he’s built a lot over many decades. After selling some restaurants (which he called a nightmare with so many employees), when he started the travel agency, it was ‘I just want to work with my mom and do this ourselves.’ But they couldn’t handle eight weddings a month, then 12 weddings a month, so slowly they added one person, then two, then three. Coming out of COVID when travel opened up and all that pent-up demand hit, he was capped out – he didn’t want a huge enterprise. He kept joking ‘I’m going to sell the business for six times multiple,’ not knowing that was going to be me.
Let’s get into the numbers. You said 100 weddings or groups a year with average group size of 60 people. What’s the revenue of the business?
Revenue last year was about $8 million in gross booking revenue – that’s all the trips added up. The net revenue, which is our commission before internal expenses, is about 15% – so about $1.3 million on that $8 million. The beauty of this business is it’s low overhead – no inventory, asset light. The only real expense is people. On that $1.3 million in commissions, about $950,000 is SD (Seller’s Discretionary Earnings). The margins are amazing – this is the big difference between a traditional travel agency and one that’s niche-specific and evolved with the internet era.
How do you build a moat in this business? Is it brand or referrals?
It’s a good question that I struggle with. There’s keyman risk – my dad was the face of the business. In this space, there are two or three large companies that plan destination weddings and a bunch of small mom-and-pop companies. There’s not really a moat – it’s hard to say ‘we get exclusive perks.’ What we have going for us is experience – we’ve been doing this longer than most. Eighty-something percent of couples never visit the resort before they get married, so they’re trusting us with that process. You want to make sure we’ve been to that resort, know the wedding team, venues, and all small details. That takes time to learn because things change often. The service aspect is so important – a couple brings 60 people and says ‘trust Jared with this decision.’ It’s important to deliver, but you have to get a thousand out of a thousand little decisions correct, because if one thing goes wrong with a wedding (something people only do once), customers get really mad really quick.
You mentioned YouTube videos as part of your marketing. What role have reviews played in your business growth?
Something I was inspired by from SMB Twitter and home service businesses was how important reviews are. We weren’t asking for reviews – we’d thank couples after they returned home, but didn’t think about reviews because we were afraid of the four-star review for cold french fries (which had nothing to do with us). Inspired by what others were sharing about reviews for rankings and building online trust, I worked with my parents to build systems to ask for reviews, explaining ‘please review how we were in booking your room or arranging transportation’ to make it more concrete. This has become a moat – we have hundreds of five-star reviews on Google, The Knot, and WeddingWire. I can see the increase in trust and it’s helped our lead flow – couples mention seeing our 200 five-star reviews pushed them over the edge when deciding between us and competitors.
You mentioned travel agencies as a category. For niche travel agencies like yours, are they enduring? Are they for sale? What can you share about this business category?
Travel agencies as we knew them have disappeared or will disappear. The ones that do well are geographically constrained – the travel agency in town where older people want that hand-to-hand relationship. I think those will survive. The big online travel agencies (OTAs) like Expedia have billions in marketing budgets – you can’t compete if you don’t have marketing muscle. We’re seeing some success with younger people doing travel on TikTok, turning that into a one-or-two-person show, but I’m not sure how durable that is. The other end of the spectrum are companies like ours that niche down – becoming experts on one specific type of travel. For us, that’s niche group travel. Another thing I learned through Twitter: find businesses that can’t be ‘Amazoned away’ – it’s really hard to plan a destination wedding through ChatGPT. There’s no way to do that right now, and I don’t see how you could through AI in the near term.
How do you see growth potential? What are the levers to pull to get from current metrics to potentially $5 million in top-line revenue?
If we can get to $5 million in top-line, that would be a great place. The levers: first is people – our biggest expense. How do we become more efficient? Working with more global talent is one way – talent isn’t geographically constrained and neither is our business. Second would be marketing. The YouTube channel was fully organic – we’ve tested some paid ads but not meaningfully. We just brought on a social agency for organic social, and we don’t do much partnership marketing. All these levers are sitting there waiting. If I look at the P&L, number one expense is people, so I’m going there first. Then the biggest gap is marketing, so that’s number two. Something crazy: we help 6,000 people plan travel each year (100 groups x 60 people), have their email addresses, communicate with them regularly – then we generally don’t speak to them again. We haven’t leveraged our email list – we should be talking to these people monthly, recommending other travel options. This is low-hanging fruit.
How does one buy a business from one’s parents? How did you approach the negotiation?
It started as a joke but became reality. I did research on reasonable multiples and explained to my dad what some risks were. The purchase price was very generous – 2x SDE. 2024 SD was right around a million, so agreement was 2x SDE – purchased for $2 million. Part of the agreement was he would carry a 10% seller note. The rest would be an SBA loan. I knew the insides of the business – I built the tracker, monitored revenues – so there wasn’t traditional due diligence. The pro is I could trust the seller; I’ve known him for 35+ years. The con might be tunnel vision – maybe I overlooked things someone coming from outside might have seen, but I tried to stay open-minded.
Why do you think your dad gave you such a favorable price? Even 3x would have been reasonable given the margins.
Totally, 3x-3.5x would have worked given the margins. People say ‘you want the terms, not the price,’ but because of how the business is structured and where revenue is now, I’m very comfortable with the terms and feel there’s a path to growth. The obvious answer is it’s because of the familial relationship, and I recognize that’s not the norm – not everyone acquiring a business has that opportunity. He worked hard, built this business over many years, took many angry phone calls – why would he just hand over the keys? I would feel uncomfortable if he did. I tried to negotiate a larger seller note, but I’m actually grateful it’s structured traditionally with an SBA loan – it adds responsibility to carry on their legacy.
How did you choose to use an SBA loan broker rather than going directly to a bank?
I met Heather from Viso Capital on Twitter years ago when she tweeted ‘I’m locked out of my account, can anyone help.’ I helped her, and we talked occasionally over the years. When it came time to purchase, I reached out because I’d seen her content and heard her on podcasts. She was amazing – helped evaluate different banks, explained mechanics I didn’t understand (I come from marketing/sales, not finance). It wasn’t so much ‘use a loan broker’ – I specifically wanted to work with Heather. If I decouple Heather from ‘loan broker,’ the value proposition was 100% – I wouldn’t have known where to start. Being handed term sheets and explanations of pros/cons was invaluable. The same reason people trust us to plan travel – I trusted a loan broker because this is what she does. I’ve never been through this before, so why feel confident doing it myself when she’s seen it thousands of times?
Jared Benoff Business Stats
Vacation Ease has grown from a parents’ side hustle into a thriving destination wedding travel agency with impressive financial metrics. Jared Benoff sees clear pathways to scale this profitable business further while maintaining its signature service quality. Below are the key business statistics that demonstrate why this is a compelling acquisition opportunity in the travel sector.
- Generates approximately $8 million in gross booking revenue annually
- Earns $1.3 million in commission revenue (15% of gross bookings)
- Operates with $950,000 in Seller’s Discretionary Earnings (SD)
- Manages about 100 groups per year (primarily destination weddings)
- Serves approximately 6,000 travelers annually (60 people per group)
- Runs with a lean team of about 10 employees handling all operations
| Metric | Value |
|---|---|
| Gross Booking Revenue | $8,000,000 |
| Commission Revenue (15%) | $1,300,000 |
| Seller’s Discretionary Earnings | $950,000 |
| Annual Groups | 100 |
| Travelers Served Annually | 6,000 |
| Team Size | 10 people |
Jared Benoff Method
Jared’s approach combines leveraging family business knowledge with modern marketing tactics rarely seen in the travel agency space. His method transforms what could be a traditional agency into a scalable, review-driven business with multiple growth pathways. Here’s how Jared executed his method to build a successful travel agency acquisition:
- Leveraged intimate knowledge of his parents’ business gathered over 15+ years of informal consulting
- Applied marketing strategies from unrelated industries (HVAC/home services) to the travel sector
- Systematically built review generation processes after recognizing their critical importance
- Created organic YouTube content that became their top lead source with minimal production
- Maintained strategic vendor relationships while avoiding geographical constraints
- Structured acquisition with seller financing and SBA loan for traditional deal security
Jared Benoff Tools
Jared uses surprisingly simple tools to run a travel agency business that most would assume requires complex systems. By focusing on relationship management rather than expensive technology, Vacation Ease maintains remarkable profitability. Here are the key tools that power their operation:
- Basic CRM tool from 1999 that ‘does the job’ despite ‘ugly UI’ (low cost, functional)
- Google Business for managing reviews and local SEO presence
- YouTube as primary organic marketing channel with minimal production value
- The Knot and WeddingWire for wedding-specific lead generation
- Simple email list management for maintaining post-trip relationships
- SBA financing through Viso Capital for acquisition funding
Key Notes
Several critical insights emerge from Jared’s successful travel agency acquisition that challenge common assumptions about this industry. These key observations can help potential buyers evaluate similar opportunities:
- Travel agencies aren’t dead – they’ve evolved into specialized niches where human expertise matters most
- Destination weddings represent an ideal niche: high-value, complex logistics that can’t be automated
- Reviews are MORE critical in travel than many service businesses realize
- The ‘laptop business’ model works because real expenses are primarily people, not inventory
- Businesses serving ‘experiential’ purchases (like weddings) are AI-resistant for the foreseeable future
- Trust is the hardest currency to build but critical for acquisition success
Get Started in Just 5 Steps
Following Jared’s path to successfully buy a travel agency business requires strategic planning but isn’t complicated. These five steps mirror his journey from tech executive to travel agency owner, showing how anyone can follow a similar path:
- Identify your ‘zone of power’ – a travel niche where your background gives you advantage (like destination weddings)
- Focus on businesses that can’t be ‘Amazoned away’ – complex experiential services requiring human expertise
- Start implementing modern marketing tactics (reviews, content) that competitors in the space ignore
- Structure acquisition with both seller financing and SBA loan for security and reasonable terms
- Commit to relationship building rather than chasing the next technological ‘solution’ for travel
Conclusion
Buying a travel agency business doesn’t have to be the risky proposition many assume. Jared Benoff’s success with Vacation Ease proves that specialized travel agencies, particularly in high-touch niches like destination weddings, remain incredibly viable and profitable businesses. By focusing on what makes travel personal rather than trying to compete with OTAs on price, smart buyers can find acquisition opportunities that leverage human expertise in ways AI can’t replicate. The key is finding the right niche, building authentic relationships, and implementing modern marketing practices that most traditional travel agencies still ignore. For those willing to learn from Jared’s journey, the path to buying a profitable travel agency business is clearer than ever.