On April 11, SmartFlyer set out to do something no other host agency has done before: connect with industry partners, clients and consumers via the digital publishing platform Substack.
Substack’s reach is impressive — it boasts more than 50 million active subscriptions, and 5 million of those are paid, meaning readers pay a fee to access select content. A Substack creator can write stories and share photos and videos that are published online and then sent to subscribers via email. Connecting with those readers is made simple through a comments section, and users can monetize all or part of their content via the platform.
Kayla Douglas, director of content for SmartFlyer, says that “Stay Awhile, a Substack by SmartFlyer,” will take advantage of all of the above. Here’s why.
Why SmartFlyer is Leaning into Substack
Douglas has been a Substack user herself for years, and that experience helped her see an opportunity for SmartFlyer. Though the host agency already has (and will continue to use) a digital newsletter, Douglas knew Substack could be a means of creating differentiated content.
Kayla Douglas, director of content for SmartFlyer, sees Substack as a means of creating engaging, of-the-moment content.
Credit: 2025 SmartFlyer
“Our newsletter is short and tight, and it sends people to the website for the full story,” Douglas said. “Everything we create for the site is quite evergreen. And while the newsletter has been great, we're boxed in to some extent.”
SmartFlyer’s newsletter goes out once a month, so the team only has 12 chances per year to get in front of their audience. For that reason, they select topics for each letter judiciously.
“Our latest newsletter, for example, was all about privacy being the ultimate luxury,” Douglas said. “We try to source interesting, unique brands that showcase that month’s theme. In this case, that was a niche villa company called Ultima Collection.”
Douglas realized that SmartFlyer was missing a platform for more timely and unique stories — ones that wouldn’t need to live forever on the website but that were still worth telling.
Ideally, “Stay Awhile” is the solution. The team will publish the Substack weekly, and each post will have five sections that highlight the musings and experiences of SmartFlyer team members. For example, in the first-ever post, readers will find a Q&A with Michael Holtz, CEO and founder of SmartFlyer, about two different airlines (All Nippon Airways and Japan Airlines) that he flew with when traveling to Japan twice in one month. Another section quotes SmartFlyer advisors who recently experienced the new Orient Express La Dolce Vita train experience and the Orient Express La Minerva Hotel in Rome.
“These stories feel relevant this week, and much more in-the-moment, but maybe they won’t be relevant in six months,” Douglas said. “They are based on current feedback from our agents on the ground.”
While SmartFlyer advisors have their own microsites on the agency website, there hasn’t been a place for them to author their own stories. “Stay Awhile” gives them that space; they can share tidbits from trade shows, advisory board meetings, property inspections, familiarization trips, personal vacations and more.
Douglas says that, as SmartFlyer approaches its 35th anniversary, sharing the voices of the people who make the agency successful is the goal.
Erina Pindar, chief operating officer of SmartFlyer, was featured in the agency’s inaugural Substack post.
Credit: 2025 SmartFlyer
“Our advisors can come to us [and use our Substack] to get exposure to a new set of eyes,” Douglas said. “And the platform feels a little bit more like a conversation — you can't cultivate community without engagement from those within your community. So, shouting into the void, whether the void is Instagram or another platform that feels stale, isn’t really giving us that reciprocity.”
Right away, the first edition of “Stay Awhile” made its mark.
“One of the most exciting things about the launch is that we got comments from people we don't hear from on Instagram,” she said.
A client in his 70s was among the first readers to reach out to Holtz and compliment the new project.
“To me, that is the ultimate use case,” Douglas said. “Connecting with somebody who's been working with us for decades and is very much open to a new platform is really exciting.”
The SmartFlyer team will use different metrics to measure the success of the project over the coming months. Primarily, they’ll track the number of new subscribers who find them through organic Substack search and use, and they will measure open rates and views.
Why Travel Advisors Should Consider Starting a Substack
Douglas sees Substack as an ecosystem any agent can use to amplify their expertise. She likes that readers can quickly connect with an advisor via the message function, and she imagines that even simple posts can bring in leads.
"I think the point of this platform is to be a bit more nimble,” she said. “We want to have the ability to respond to someone more quickly. And things are more interactive when users consume content within the Substack ecosystem. There are cool features in the app — you can engage with polls, you can comment, you can like other people's notes. There’s a social media element to it.”
Substack allows advisors to monetize their content, too, and Douglas thinks this could be a good way to entice an audience travel advisors might not reach otherwise.
Take a DIY traveler, Douglas says. If that traveler finds an advisor’s Substack, they might not make a booking, but they may very well conduct trip research via the advisor’s Substack. And an advisor can place certain information behind a paywall, restricting what content a reader can see without paying a subscription fee.
This option opens up a completely new revenue stream for advisors, Douglas says. SmartFlyer intends to put “micro guides” behind a paywall. Instead of a guide to New York City, they’ll do a guide to Chelsea, for example.
“We want these to be really niche,” she said. “Our guide to Chelsea, which is where our office is, will have completely different recommendations than a guide to the West Village. And you can take that same approach to the Marais in Paris, or the Trastevere in Rome. And maybe that draws in somebody who's never heard of SmartFlyer.”
Ultimately, Substack is another way for advisors to demonstrate their value.
“A lot of people outside of our industry would be amazed at the level of detail and the logistics that are involved in the trips advisors plan,” Douglas said. “How can you make that interesting? How can you earn people’s trust and make them want to work with you, but not give them so much that they don't need you at all?”
Douglas says that putting micro guides behind a paywall is less about revenue and more about intrigue and protecting SmartFlyer’s “secret sauce.”
“I pay for guides all the time, because I almost trust a recommendation more when the person is like, ‘I don’t need to just give this out,’” Douglas said. “There's a level of exclusivity to that.”
If the idea of helming yet another marketing tool feels daunting, Douglas is ready to give you a pep talk. First, she says, using Substack is straightforward. Second, she wants advisors to remember that marketing shouldn’t be on the back burner, and Substack stands to be a great way to market yourself.
“You have to treat marketing as a part of your business calendar block, and set aside time for it,” she said. “Then, remember that there's a difference between promoting content and creating it. You have to be in a different kind of space for those two things. It’s easy to deprioritize that, but don’t. Sit down, create the thing and stop doubting yourself, because people will value your insight so much more than you realize.”
