Pam Holt: The Happy Host who built a community

Updated on March 6, 2023

When Pam Holt planned a family trip in July 2017 to join her eldest daughter in Cape Town, South Africa, at the end of a school service project, a friend suggested that Pam short-term rent her home in Chicago to travelers while the family was away.

“At the time, I thought the idea was ridiculous,” Pam said, “because it’s just our house. We live here with our dog. It wasn’t set up in any way to host, and frankly, it just never even occurred to me.”

Yet, the idea also intrigued Pam. As a self-employed real estate broker and lawyer, she could make her own schedule, but taking time off also meant she wasn’t earning income to pay for the family’s expenses.

A short-term rental experiment

She posted a listing on Airbnb and quickly landed a booking that covered the week that she would be away visiting her eldest daughter.

And then, the booking requests kept trickling in. Soon, Pam had rented out her home for three weeks instead of one, and the family extended their trip by two weeks. 

“We were going to just stay in Cape Town, but we ended up in three countries,” Pam said. “We traveled around, and we spontaneously went to an uninhabited island. We did all kinds of really fun things that I didn’t see coming, and I certainly didn’t budget for, but because I wasn’t paying for it – the guests were paying for it, it seemed like a great idea.”

Short-term rental host to world traveler

She and her two daughters now travel the world whenever her youngest daughter, who is now 13, is on a school break, and when they do, they rent out their home to travelers in Chicago.

“As a single mom, it was difficult to divert funds to big vacations when I had school tuition to pay for and all kinds of other expenses,” Pam said. “And so being able to host allows us to now take the trips that I would have never thought we would have been able to take. And we really spend time as a family; it’s kind of our thing now.”

The unforgettable adventures with her daughters sparked her passion for helping other women to make the most of what they already have: extra space in their home.

“It might be an attic space, a lower level, a guest house, or your whole home, if you travel like I do. But it’s about learning the foundational components of hosting, which are hospitality, customer service, and guest engagement,” Pam said.

Creating a short-term rental community

In May 2020, she founded the Happy Host Academy, a community for women hosts who want to learn from experts and from each other about running a short-term rental business in their primary residences.

“I tell people, when Airbnb was first launched, it was about hosting guests in your home, and I’m trying to get back to that as a business model,” Pam said.

For a monthly fee, Happy Host Academy offers educational resources, webinars by Pam and special guests from the industry, and a forum where hosts can swap stories, information, and tips.

Pam focused on building a community of women who like her might be juggling breadwinning, child care, parent care, and other responsibilities or are facing some kind of transition in their lives such as a divorce, retirement, or children leaving home.

Women are often drawn to short-term rental businesses because of the flexibility it provides in balancing all of these responsibilities, and statistics back that up. According to the 2022 State of the STR Community Survey, 58% of the STR industry consists of women.   

“Many women are innately hospitable, and it’s not a stretch for us to make it comfortable for guests to stay in our spaces,” Pam said.

“I teach them to maximize the potential of their unused living spaces,” Pam said. “So unlike some of the educators in this space, I’m not teaching how to scale and how to do rental arbitrage and how to acquire a huge number of listings. I’m teaching you how to accommodate guests in a space you already own.”

Principles of responsible renting

Being a good host means anticipating the needs of guests before they realize those needs and operating in a professional manner, from screening guests and personal safety to learning and following local regulations and having short-term rental insurance, Pam said.

When onboarding new members of the community, she discusses the importance of abiding by local STR regulations and explains the hierarchy of regulations from state-level to HOA restrictions. She also believes that everyone in the household needs to agree to short-term renting; otherwise, the business could flop.

One of the areas where hosts often need education is in short-term rental insurance. Many hosts erroneously assume their regular homeowners insurance policy will meet their needs as a host or they purchase short-term rental insurance without checking to make sure it covers everything they need in their business.

Pam partners with Proper Insurance, which specializes in vacation rental insurance. 

She recently hosted Nick Massey, national sales manager at Proper Insurance at the Happy Host Academy to discuss the fundamentals of STR insurance.

Some STR insurance coverage is uniform, but other aspects are site specific to the host’s home, location, and amenities.

“He took us through everything we needed to know about what’s different between a regular homeowners policy and short-term rental policy, and it was really helpful,” Pam said.

“There are a lot of different insurance issues, and if you don’t have someone in the profession guiding you, there’s no way it’s intuitive.”

For instance,“loss of income coverage is not something a new host necessarily would think about,” Pam said. “They wouldn’t necessarily think about hosting as being a business, especially if you’re just renting a room in your home.”

Tips for being a hospitable host

Pam also holds educational sessions on hospitality – which is her favorite part of hosting. 

“Hospitality is anticipating what guests are going to need, and then having that already ready and waiting when they arrive,” she said. “It’s treating them how you would want to be treated. It’s making sure that the check-in process is flawless, there are no issues with the heat or any of the devices, everything is running smoothly.”

One of her special touches is making sure her kitchen is stocked with a wide variety of spices for guests who like to cook.

“Who wants to go out and buy 15 spices to use just once? So that’s the kind of thing I’d like to anticipate for people,” she said.

Her passion for coaching new hosts was also behind her decision to participate in the Hospitable Hosts Project.

Spearheaded by United Kingdom-based host Jodie Stirling, the project collected true stories written by 40 short-term rental hosts from around the world meant to inspire and educate other hosts. 

The stories were published as the anthology, Hospitable Hosts: Inspiring & Memorable Stories From Airbnb Hosts Around the World to Educate & Motivate, in May 2022.

A sequel is scheduled for release later this year.

Pam shared the story of how she became a host and the adventures around the world that she has had with her daughters.

“When Jody approached me, she specifically started talking about how to care for a guest and how to provide the highest level of customer service, and I really felt like it was something that I wanted to be a part of,” Pam said.

She often thinks of her father, who died in 2014, when she is traveling with her daughters. Her father, who worked as a judge in Chicago, had always wanted to travel abroad but had never done so.

“I think he would have gotten such a kick out of this, and I think he would really appreciate me being able to take an asset that we already have and really maximize it, not just have it as something that I’m constantly paying for but something that is giving back to us.”

…