It’s good to learn from your mistakes. It’s better to learn from other people’s mistakes.
The legendary investor Warren Buffet is often credited for coining this shrewd snippet of entrepreneurial advice. And while Buffet was not referring to scaling a travel agency, it turns out that travel advisors would be wise to heed his words.
According to industry veterans, it’s not uncommon for business owners on the precipice of their first hire to make frustrating missteps. Here, advisors who have graduated from this phase of their business share how they knew they needed help, how they decided whether to hire W-2 employees or independent contractors (ICs) and what steps they took to ensure that they were following the law.
When Should I Hire Help?
Rebecca Alesia launched Wanderology, a New York-based SmartFlyer affiliate, in 2012. After four years of operating the agency solo, she decided she needed help.
“I had hit $2 million in production that year,” Alesia recalled. “And I was having trouble keeping on top of some of the administrative tasks, such as invoicing, itinerary preparation and some of the concierge communication with hotels.”
At the time, Alesia used a Florida-based virtual remote support agency to hire an independent contractor.
“I started with them at 20 hours per week,” she said. “And then I thought, ‘I need more.’"
Her IC hours climbed to 30, then 40 hours per week. At that point, she realized she needed to bring on someone a bit more regularly. Wanderology has been through some ups and downs since, but today, the agency works with four ICs — three administrative support people and one travel advisor. Alesia is quick to note that she really appreciates the flexibility of working with ICs.
“It enables you to use as many hours as you want, and to reduce if you need to if business slows down,” she said. “And I’ve found the people who work with us are looking for flexibility.”
Kerry Dyer, chief development officer at Brownell Travel, says her host agency offers very specific advice to advisors about when they should bring on help.
“What we recommend is when someone has hit $1 million in annual business or $100,000 in revenue, they need to consider bringing someone onto their team,” Dyer said. “That’s when we find they really start to feel the burn and they need to invest in bringing on a staff member.”
Rebecca Alesia launched Wanderology in 2012.
Credit: 2026 Rebecca AlesiaWho Should I Hire?
Byrd Bergeron, CEO and founder of The Travel Byrds, an Ohio-based affiliate of Travel Planners International, launched her agency six years ago, and today, the company operates with a mixture of employees and ICs.
“In total, we’ve got about 20 W-2 employees, who are support staff,” she said. “And right now, we’ve got 22 ICs.”
Bergeron says she expects her agency will reach about $20 million in sales this year, and she attributes her company’s growth to a committed focus on ample administrative support.
“We have a team that does all of the invoicing,” she said. “We have a team that does all the guest experience work, such as dinner reservations or spa appointments. And then we have a team we call our pre-departure team that rechecks everything right before travel to make sure it all looks good.”
Bergeron says her best advice to advisors looking to scale their travel agency business is to hire administrative support. Instead of bringing on an IC travel advisor and giving them sales leads, Bergeron encourages agency owners to keep those leads for themselves and hire someone to help with work that doesn’t require an expert.
“Get someone else to answer your emails at the end of the day,” she said. “If I could go back and redo it, I would have done that first.”
Brownell’s Dyer agrees, saying her agency also encourages its advisors to first invest in back-end support so they have more time to strategically grow their companies.
“When the advisor is freed up from a lot of the administrative things, it gives them more time to prospect, make more intentional phone calls, reach out to people and follow up on more leads and introductions,” Dyer said.
"Maybe you’re spending more time upselling people. Maybe you’re taking more time learning about a new destination, and so you’re selling that.”
However, both Dyer and Bergeron agree that there is a clear circumstance where hiring additional sales help makes good sense.
“If you’re somebody who is overwhelmed by the number of leads — people are just coming out of the woodwork — and you think, ‘Even with an admin, I still couldn’t handle this,’ that’s a different discussion,” Bergeron said. “That’s where an IC travel advisor may make sense for you.”
ICs Versus Employees
Longtime labor and employment attorney Thomas Carpenter opened Huckleberry Travel — a New York-based Uniglobe Travel Center affiliate — with his husband David Slivken in 2017. The duo works with four IC travel advisors.
What we recommend is when someone has hit $1 million in annual business or $100,000 in revenue, they need to consider bringing someone onto their team.
“They are truly independent, so they can book whoever they want with whatever supplier they want,” Carpenter said. “We don’t tell them how to do their job, and basically, they are all people who just want to sell travel. They don’t want the responsibility of running their own business. So, they sell travel under our business name — under our branding — and we pay them a split of the commissions that come in.”
Carpenter is also still practicing law, and he represents nearly 2,500 travel agencies and small tour operators around the U.S., working regularly with them on the legal requirements of onboarding independent contractors and employees.
“A lot of small-business owners prefer to work with independent contractors because, simply put, it’s less expensive,” Carpenter said. “You don’t have to pay payroll taxes, and you don’t have to comply with minimum wage and overtime regulations.”
He adds that employers also need to pay people using a W-2 tax form, carry workers’ compensation and unemployment insurance for their businesses and — depending on the size of their company — may also need to cover other employee expenses, such as healthcare.
“Whether it’s healthcare, family medical leave or paid leave, all of those things are generally governed by the size of the business,” Carpenter explained. “So, if you have just one or two employees, that’s not necessarily going to trigger a lot of those laws, but when you start getting 15 or 20 people working on a W-2 under your business, then some of those things come into play.”
Carpenter notes that there is a range of services, such as Gusto and Paychex, that agency owners can use to help them meet payroll and human resources requirements. While these programs can be expensive, American Society of Travel Advisors members receive a 25% discount on payroll services from ADP, and the first month is free, according to an ASTA spokesperson.
Martha Rhodes explained that as her business has grown, so have her existing employees’ hours.
Credit: 2026 Martha RhodesMartha Rhodes — owner of Martha Rhodes Travel, a Virginia-based Brownell Travel affiliate — uses Square Payroll to help manage many of the requirements for her four W-2 employees. Rhodes, who started her agency 15 years ago, has only ever hired part-time or full-time employees and has chosen not to work with ICs, in part because of her affluent clientele.
“I didn’t want people to just work on their own clients in a silo,” Rhodes said. “I needed help taking really good care of the clients who were already my clients. So that’s why I felt, for my business model, I wanted employees who were going to help me manage the business I had.”
Rhodes adds that bringing on people part-time has worked well, explaining that as her business has grown, so have her existing employees’ hours.
“Start somebody part-time who is interested in taking on more work,” Rhodes said. “And if or when you find, ‘Oh my gosh, my business is going gangbusters,’ if that person can take on more hours, that’s the best place to get more help.”
Do I Need an Attorney?
Huckleberry Travel founder and attorney Carpenter says that many of the for-pay services are likely to cover most bases for agency owners who hire W-2 workers. But he is quick to encourage advisors who are considering IC arrangements to first consult with a lawyer.
“There’s a lot of scrutiny about independent-contractor relationships,” Carpenter said. “And a lot of people in the travel industry are doing it wrong.”
There’s a lot of scrutiny about independent-contractor relationships. And a lot of people in the travel industry are doing it wrong.
Carpenter says one area where advisors are routinely making mistakes is in the contracts they’re using to onboard ICs.
“They want to have a solid agreement and not something they’ve pulled off the internet — not something that’s AI,” Carpenter said. “They really want to understand what’s in the contract. Talking to an attorney can help them with that and with best practices, so they’re not putting systems and processes in place that are going to burn them if they get audited.”
Wanderology’s Alesia has worked in the past with Carpenter on legal issues, and she is also quick to encourage consultations with an employment expert before finalizing any hiring decisions.
“As travel advisors, we’re always telling our clients, ‘You should really consult a professional,’” Alesia said. “And yet, if you talk to 100 travel advisors and ask them, ‘Did you speak to a lawyer or an accountant before you started hiring?’ most will say no. So, we need to take our own advice and retain professional help before doing these things.”
