At some point on her flight from Cape Town to Greece, a Grammy-nominated musician who shall not be named realized how close she was to Istanbul.
“I've always wanted to go there,” she said. “Can we go there?”
Fortunately for the artist, her travel advisor — Katy Caldwell-Cole, founder of Touring Folk — was right by her side. The two had just completed work commitments in Cape Town after two weeks on safari with Abercrombie & Kent.
"So I was on the phone, on a boat, booking rooms at the Four Seasons Hotel Istanbul in a day-and-a-half,” Caldwell-Cole said.
Safe to say, Caldwell-Cole is not your usual travel advisor. Though she started her agency in 2023, she spent two decades as a tour manager for rock bands such as Flyleaf, where she handled logistics and all travel bookings for the talent and crew.
“When I started, I always booked our own travel because I am so Type A,” she said. “I wanted to know that if there was a mistake, I made it. I wanted to be able to own it and fix it.”
Early on, she noticed the IATA box on bookings and looked it up. That’s when she realized she could make money off hotel stays.
“So, a few years ago, I decided to transition off the road and start my own firm,” she said.
And the experience has paid off, big time. Last year, with just one newly hired part-time employee, Caldwell-Cole reached $2.5 million in sales. This year, with an additional full-time employee, she expects to reach $9 million. Part of that growth has come from expanding into ultra-high-net-worth (UHNW) clientele, a move that has already resulted in a $6.7 million 12-person charter cruise to Antarctica.
High Touch Is Highly Necessary
Her boutique agency currently serves four entertainment clients, one corporate client and one UHNW CEO she met through one of her musicians.
Serving entertainment clients that she has personally managed on the road means she knows them — and their decision makers — in a way an intake form and discovery call could never achieve.
"It's a family affair — I've been really lucky,” she said, explaining how her son has been joining her on the road since he was 4 months old, has visited all 48 continental states and has formed friendships with her clients’ kids.
She also understands all the nuances of life on tour, from having to book two tiers of hotels for different levels of crew to knowing how to find dependable last-minute transportation.
“My large entertainment client was with a larger firm and they said, 'We're not completely happy — they just don't understand us,'” she said. “The agency was really big, and they had so many people with hands on the booking, and things were falling through.”
I've got a quote on a sticky note on my computer screen: 'The tighter you cling, the slower you will grow.' I look at that every day.
Because this kind of work is so high-touch and prone to last-minute changes, Caldwell-Cole says she will keep her agency small — and does not aspire to have a team of 40 advisors working under her.
"That direct connection with the client is a must when people are trusting you with this much money,” she said. “We're trying to keep the growth from going too fast, to where clients just become another number. You can't use the same formula you'd use for, say, a cruise agency doing group cruises.”
But help is still essential, especially because Caldwell-Cole continues to actively manage tours on the road. She says it has been “life changing” to pass off the work of managing credit card authorizations, pre-keys and hotel folios.
Last year while working the annual music festival at Luck, Willie Nelson’s ranch, Caldwell-Cole got to meet secret musical guest, Kermit the Frog.
Credit: 2026 Katy Caldwell-Cole“I handle the larger outline and the reservations, and [my team] takes over from there,” she said. “But this job is so mobile. As long as I've got my laptop, my extra screen and Wi-Fi, I can do it anywhere. And it's almost like I'm scouting these places — I'm staying in these hotels with these artists.”
She recently completed Sabre training and currently handles most air bookings for her clients “because that’s where things can go wrong.” Recently, though, she realized she needs someone else to act as her air desk.
"That's the big thing I've worked on the past couple years — realizing I can't do it all and knowing what to delegate and what brings me joy,” she said. “I've got a quote on a sticky note on my computer screen: 'The tighter you cling, the slower you will grow.' I look at that every day. If you're clinging to everything and want to be the expert on everything, you're going to stay where you are.”
From Entertainment to Ultra-High-Net-Worth
Caldwell-Cole wants to open up her business to take on a few more entertainers (one established and two up-and-coming) and eventually more UHNW clients, who she says have a lot in common with her entertainment clients.
With her musician clients, she typically works through their tour and production managers, “the people who travel with them day in and day out and live on those buses with them.” And while the CEO structure is different, they are also being handled by a team, made up of their executive assistants and sometimes their chief financial officer and legal teams.
It's last-minute; it's having plan A, B and C sorted out. When something happens and they ask you, 'What now,' you've got to have that answer already.
“A lot of it translates,” Caldwell-Cole said. “It's last-minute; it's having plan A, B and C sorted out. When something happens and they ask you, 'What now,' you've got to have that answer already. And working with the right partners has been crucial.”
Caldwell-Cole says her job is to make sure her clients don't have to think about anything, because their time is worth money.
“You have everything planned out — breakfast is set and ready when they come out of their room,” she said. “They're not ordering, they're not waiting. The car is there; you tell them which car to get into.”
The Road to Landing a Seven-Figure Booking
She tells her friends in tour management that advising is a great next career, but wishes there were more conversations about how to do it. Because her model is so different, there hasn’t been a road map and she’s had to figure it out.
Investing in professional development and forging a community of like-minded advisors has been essential — and something she credits to attending the Future Leaders in Travel event (Future Leaders in Travel is powered by TravelAge West).
"At Future Leaders, nobody was gatekeeping and there was collaboration — everybody was there because they wanted to learn and grow,” she said, noting that she now regularly keeps up with advisors she met there to workshop the back-end parts of their businesses. “You always wonder if you’re doing it right or if there’s an easier or better way, so it was refreshing to see that several advisors were doing a lot of the same things as I was.”
One of TravelAge Wests "5 Future Leaders to Watch," Katy Caldwell-Cole loved getting to learn new ideas from the advisor community at the 2025 Future Leaders in Travel event in Alaska.
Credit: 2026 Katy Caldwell-ColeShe’s also had to learn through trial and error. After leaving a host agency that leaned heavily on preferred suppliers that did not work for her clients, she recently became a fully independent advisor through Network of Entrepreneurs Selling Travel.
“I've always needed that freedom to do my own thing,” she said, explaining that she became a top seller of Joshua’s Worldwide after they were the only supplier that could help her with a last-minute request.
"I couldn’t find anybody, so I called the FBO [at the air terminal] and I said, ‘I’ve got someone landing in hours — who do you guys use,’” she said. “I followed up with a phone call and ended up talking to Joshua who owns the company. His brother actually drove my client — and now they help us source transportation everywhere.”
Another reason preferred suppliers don’t always work is because entertainment and UHNW clients want to travel where their friends recommend — or where they’ve read about, which requires her to create a relationship with the supplier before booking.
"My CEO client doesn’t call it his bucket list — it’s his ‘what’s next list,’” she said. “And that’s where the Antarctica charter came from. His friend had used the company, EYOS Expeditions, and had good feedback.”
She says she has spent a lot of time vetting the company and building a relationship on multiple calls — including one with the client where he could choose from different ship options. With travel about 10 months away, she is now in proactive problem-solving mode, a necessity with a booking of this scale.
"A lot of time is spent going through scenarios that hopefully don’t happen, but if and when it does, we’ve already got the answer and we’re working on it,” she said. “It’s fixed before the client even knows.”
