A millennial couple dipped into their retirement savings to buy a Vermont vacation home. He now runs a 15-member Airbnb empire that generates over $100,000 in bookings a month.
- Lauren Hudson, 40, and Chris Krieger, 39, bought a modern Vermont cabin in 2017 as a second home.
- He turned to Airbnb to cover the costs, then he quit his daily job to run Airbnbs full time.
- The collective now has 15 properties, bringing in over $100,000 in gross bookings a month.
The Vermont cabin that Lauren Hudson and Chris Krieger bought in 2017 for $235,000 was supposed to be a vacation home that they sometimes rent out on Airbnb to help cover the mortgage.
The Connecticut couple hope to rent it out a few weekends a month and maybe even break up—or in the worst case, sell it if their aspirations aren’t met. Instead, the property was so successful on Airbnb that the couple had to start taking the weekend off for themselves on the rental calendar.
It set him on a new career path: building a New England Airbnb empire that includes 15 properties, six he owns and nine he manages for clients of the property management and marketing firm he calls Wildwood Collective.
He hadn’t anticipated how lucrative short-term rentals could be. At the closing table for the cabin in August 2017, both the seller’s agent and their own said the couple can expect vacation-rental income of $15,000 a year. In the first year, they brought in more than their carrying cost of $2,000 a month. In 2018, they brought in $62,000 in revenue. In 2021, that figure nearly doubled to $115,000.
“The house could pay for itself for a year and a half,” Hudson said.
The company’s success has allowed Hudson, a former CPO of a mid-sized consumer-credit union and a creative director for a global market-research firm, to quit his day job to work full-time at Airbnb.
“One of our original goals was to employ ourselves. We were really sick of corporate,” Hudson said. “I left in March of this year, and I’ll never go back.”
The couple broke down how they pulled it off.
It started with the search for a vacation home
Hudson, 40, had returned from living on the West Coast in 2016 when she and Krieger, 39, decided to buy a weekend home that Hudson called their life in Trumbull, Connecticut, with “endless lawns” and “endless traffic.” . 20 miles from New Haven.
“It was a thoughtful project for me. I was really missing that connection to nature and getting some peace and quiet,” she said.
It was also Hudson’s West Coast leanings that drew him to the property he named the Green Mountain Modern House, a jolt of contemporary architecture that’s more Joshua Tree than cabin nestled in the woods of Jamaica, Vermont.
Hudson and Krieger bought the Green Mountain Modern house in 2017 for $235,000. This is the property that launched his Airbnb empire. Wildwood Collective
The property topped his budget at $235,000, but its uniqueness convinced him it was a good investment. The couple were so convinced, they liquidated part of their 401(k) to make a $30,000 down payment.
Hudson and Krieger hoped to rent the house on Airbnb for about $300 a night, to help cover their $2,000 per month costs, which included their mortgage payment and maintenance. The house is a 30-minute drive from Stratton Mountain and three hours from Boston. At least, they thought they’d attract some winter-sport enthusiasts.
Hudson said, “Airbnb didn’t really exist in Vermont in 2017, believe it or not. It was very, very, very limited.” But the couple decided to give it a shot.
“But as soon as we listed it, we were kind of blown away by how much demand there was for it,” she said. “It was constantly booked. We weren’t getting enough time for ourselves.”
The house now rents around $442 a night.
‘We’re driving cash flow into expansion’
The demand pushed him to buy another property (and then a third, and so on).
Hudson and Krieger decided to buy and rent a tiny house the way they had decided the Green Mountain Modern house: It reminded them of West Coast experiences.
He purchased the self-contained property, fully furnished floor model, from the Tiny House Marketplace. It cost $67,000, and they financed 100% of the cost, minus taxes, with commercial-vehicle loans.
“The more we’ve talked to people in the industry, the less cash it is best to pay,” Hudson said.
It is located on a piece of land near Green Mountain Modern House which they rent for around $700 a month.
“We’re driving cash flow toward expansion,” Krieger said.
The Alpine A-Frame is the third property the couple has purchased. Ethan Abitz
And he continued to expand. The idea to launch Wildwood Collective, their vacation-property marketing and management firm, began in February 2020 with their third purchase, a $130,000 A-frame, in nearby Wilmington, Vermont.
Over the past three years, the two had seen an appetite for properties sold as self-contained businesses, so after funneling $20,000 into upgrading the A-frame, Krieger sold it as a marketing asset for $330,000. With listed for sale as a vacation rental.
Hudson said it took a month for the property to find an off-market buyer, who “has become our best and most trusted partner” in expanding the properties managed under the collective.
Wildwood Collective now brings in over $100,000 gross bookings a month at 15 properties, nine of which are client-owned and of which Wildwood collects 20% for its services in a revenue-sharing model.
They also consult on projects other aspiring Airbnb entrepreneurs are seeking to launch, including discovering unique properties, outfitting them with on-trend interiors, and creating branding materials.
There are challenges in the life of Airbnb
Hudson and Krieger are now facing new challenges brought on by the pandemic and, perhaps, their own success. With home prices rising, and competition becoming more fierce for the few homes on the market, all-cash buyers often favor those who rely on financing.
The couple’s business continued to flourish as they acquired unique properties at low price points once in line with the region. Hudson said the pandemic has changed the market in the regions where they operate, with not only more travelers looking for the Instagram-friendly accommodations they offer, but competitors also noticing their success and want to get into business.
“It’s hard to do that now,” Hudson said. “The real estate market is brutal. Too many people want to do what we’ve done.”
Competition from other short-term-rental owners isn’t the only obstacle. Properties for sale are not as plentiful as they once were. “We’ve tried to expand as quickly as possible because real estate becomes more scarce. Now it’s even harder to get land. The land used to sit for years, and now it’s a week,” Hudson said.
Cedar Brook Cabin is one of a handful of tiny homes operated by Wildwood Collective. Ethan Abitz
It has become more challenging for both to find and invest in unique assets that are their hallmarks and that generate those types of returns early in their operations.
“If we were lucky enough to beat 25 other investors on the modern home, we wouldn’t have the same returns,” Hudson said.
All of Hudson & Krieger’s assets are financed, which means they are making monthly payments on them. But now to compete in the market, he said, you need to come up with a cash offer.
The business also bears operating expenses for maintenance and landscaping.
Hudson said, “Let’s say you own a property in New Jersey or New York—owning a property in Vermont is completely different. You’ve never had to deal with septic and well and rural storms and roads Is.” “It’s a whole new level of maintaining an asset in areas like this.”
they’re not in it for the long haul
In October 2021, Wildwood Collective opened Camp Wildwood, a pet-friendly vacation enclave of two tiny homes in Chester, Vermont, with rentals ranging between $175 and $250 per night. In Hudson’s words, it’s the hardest project ever, but it’s also one of the most rewarding.
It’s a concept they are interested in expanding into other states such as Maine or New Hampshire, although Hudson and Krieger also envision retiring from the hustle in five to 10 years by selling their business and moving west. Hudson said she wanted to flex her hospitality background in a different way by opening an agri-animal sanctuary that would also cater to ethical tourism and education. Krieger envisions working in marine-mammal conservation and responsible ecotourism.
“This vision of the future may not be so far off,” Hudson said, adding, “We didn’t even have a business five years ago.”
As for his 401(k), Hudson isn’t worried. Trading has been good for him, and the recent downturn in the market has made him feel strong in his investments.
“I think I’ve taken it out to do more projects,” Hudson said of her retirement savings. “It may sound a little overconfident, but I feel more comfortable doing my own investing with real estate than investing in some magical fund that’s going to provide a 3% return.”
