How Smartflyer is turning travel advice into a $1bn business

Smartflyer’s penthouse in New York’s Chelsea neighbourhood is a far cry from a traditional travel agency – indeed, it’s a rather nice place for a party. Since moving here in February 2025, the company has thrown more than 30 events for customers and partners. Glass doors open onto a terrace overlooking Manhattan’s West Side and the artworks on the walls speak to the wonder of travel: pots from a Brooklyn-based Sudanese ceramicist and a hanging sculpture by a South African artist. Each piece comes from the collection of Erina Pindar, Smartflyer’s managing partner and chief operating officer. “As the travel space evolves, we want to be part of that evolution,” says Pindar as she gives Monocle a tour.

Smartflyer is no stranger to change. It was built in the 1990s on air travel – the speciality of its founder, Michael Holtz – helping travellers to secure premium cabins or solve complex flight routes. “At the time, the entire concept of travel agencies was very transactional,” says Pindar, who joined the firm in 2010 and now owns it with Holtz. “Everyone approached it like taking orders. For me, though, it was always a no-brainer that it should be based on the travellers’ needs and be a little bit more ‘advisory’ in nature.”

Pindar helped to develop the business not only in scale but in terms of shifting its strategy from airline travel to a full-service booking advisory: creating itineraries, arranging one-of-a-kind experiences, grabbing the last table at an in-demand restaurant, ensuring that clients are first on the upgrade list. Since 2010, its headcount has grown from five to 60 employees and from just a few overseas advisers to 250, spread across every continent. These entrepreneurs run independent agencies within the Smartflyer platform and earn a commission on any trip that they create. “We connect travellers with these incredible experiences and people,” says Pindar. “Collectively, we have been everywhere so if I don’t know a destination, I can go to a colleague who does.”

Clients are mostly US-based high-earners. Some want a straightforward trip to St Barts, while others want a complex itinerary in northern Kenya. Providing unrepeatable adventures – from special access to galleries during Art Basel in Hong Kong to seeing the Sistine Chapel without another tourist in sight – is where Smartflyer shines. “We all want bragging rights,” she says. “But you can make anything special. It’s about what the traveller deems valuable.”

Smartflyer’s projected revenue in 2025 is expected to hit $1bn (€860m), though this reflects the total travel revenue booked across the company’s network rather than an official line in its accounts (“the industry standard for measuring scale and buying power”, says Pindar). The founder-led, privately held business is profitable and channels “a lot” of what it makes every year back into the company. “Education is a really big part for us – adviser advancement and investing in the team members, as well as technology,” she says.

Does the company’s renewed success hint at something broader? Online booking platforms were meant to have rendered the travel agent obsolete but the industry might be entering another golden age in which it becomes, for discerning travellers, more crucial than ever. “Tiktok is terrible for travel but a lot of people see it as an authority,” says Pindar. The same goes for review sites. “If you don’t know who these people are, why are you taking advice from them?” she adds. In a business increasingly driven by algorithms, she is betting on the human touch. “Advice from a professional is very important today,” she says. “Technology misses the nuances.”

Demand for airline bookings – Smartflyer’s original business – is also coming back. Flight disruptions and cancellations have become customary, particularly in the US, where a long-term air-traffic-control shortage and ageing technology have resulted in chaos. “Having someone watch over your logistics while you travel is the most luxurious thing you can give yourself,” she says. “I never want to be in a place where a flight is cancelled and I’m running to the desk with 100 other people.”

On a recent trip back from Los Angeles, Pindar asked her team to book five flights over the course of six hours during a single day. “I wanted to get home,” she says. “That’s how we work with our clients – they want to be where they want to be when they want to be there.” When Monocle bemoans a recent cancellation, she says, with a wry smile, “Maybe we should have booked your flight?”