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How a Millennial Couple Built a 15-Airbnb Empire in 4 Years

  • Lauren Hudson, 40, and Chris Krieger, 39, purchased a modern Vermont cabin as a second home in 2017.
  • They turned to Airbnb to cover costs, then they ditched their day jobs 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 purchased in 2017 for $235,000 was supposed to be a vacation home that they occasionally rented on Airbnb to help cover the mortgage.

The Connecticut couple expected to rent it out a few weekends a month and maybe break even — or in the worst case, sell it if their aspirations didn’t pan out. Instead, the property was so successful on Airbnb that the couple had to start blocking off weekends for themselves on the rental calendar.

It set them on a new career path: creating a New England Airbnb empire that has grown to include 15 properties, six they own and nine they manage for clients of the property management and marketing firm they founded, called Wildwood Collective.

They didn’t anticipate 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 could expect to make $15,000 in vacation-rental income annually. In the first year, they brought in more than their carrying costs of $2,000 a month. In 2018, they brought in $62,000 in revenue. In 2021, that figure had nearly doubled to $115,000.

“The house could have paid for itself by a year and a half,” Hudson said.

The company’s success has allowed both Krieger, a former CPO for a midsize consumer-credit union, and Hudson, once a creative director for a global market-research firm, to leave their day jobs to work on their Airbnb hustle full time.

“One of our original goals was to employ ourselves. We were really, really sick of corporate,” Hudson said. “I left in March of this year, and I will never go back.”

The couple broke down how they pulled it off.

It started with the search for a vacation home

Hudson, 40, had just returned from living on the West Coast in 2016 when she and Krieger, 39, decided to purchase a weekend home from what Hudson called their life of “endless lawns” and “endless traffic” in Trumbull, Connecticut, about 20 miles from New Haven.

“It was kind of a sanity 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 inclinations that drew them to the property that they’ve named the Green Mountain Modern House, a shock of contemporary architecture that’s more Joshua Tree than a cabin nestled in the the woods of Jamaica, Vermont.

A rectangular home sits on a wooded plot.  The home is lit from the inside as the sun sets outside.

Hudson and Krieger purchased the Green Mountain Modern House for $235,000 in 2017. It’s the property that launched their Airbnb empire.

Wildwood Collective

The property was at the top of their budget at $235,000, but its uniqueness convinced them it was a sound investment. The couple was so convinced, they liquidated part of their 401(k) to make the $30,000

down payment


Hudson and Krieger expected to rent the house on Airbnb for about $300 a night here and there to help cover their $2,000 a month carrying costs, which included their mortgage payment and maintenance. The house is a 30-minute drive to Stratton Mountain, and three hours from Boston. At the very least, they thought they’d attract a few winter-sports enthusiasts.

“Airbnb really didn’t exist in Vermont in 2017, believe it or not. It was very, very, very limited,” Hudson said. But the couple decided to give it a shot.

“But as soon as we listed it, we were kind of blown away with how much demand there was for it,” she said. “It was continually booked. We were not finding enough time for ourselves.”

The house now rents for about $442 a night.

‘We keep the cash flow going toward expansion’

The demand shocked them into purchasing a second property (and then a third, and so on).

Hudson and Krieger decided to purchase and rent out a tiny house much in the same way they decided on Green Mountain Modern House: It reminded them of experiences on the West Coast.

They purchased the self-contained property, a fully furnished floor model, from Tiny House Marketplace. It cost $67,000, and they financed 100% of the cost, minus taxes, with a commercial-vehicle loan.

“We’ve found the more that we talk to people in the industry, it’s best to pay up as little cash as possible,” Hudson said.

It’s situated on a piece of land near the Green Mountain Modern House that they rent for around $700 a month.

“We keep the cash flow going toward expansion,” Krieger said.

A blue A-frame home sits among the trees.

The Alpine A-frame is the third property the couple purchased.

Ethan Abitz

And continue to expand they did. The idea to launch Wildwood Collective, their vacation-property marketing and management firm, took off with their third purchase, a $130,000 A-frame in nearby Wilmington, Vermont, in February 2020.

Over the three previous years, the duo had noticed an appetite for properties sold as a self-contained business, so after funneling $20,000 into upgrading the A-frame, Krieger listed it for sale as a vacation rental with marketing assets for $330,000.

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 they manage under the collective, Hudson said.

Wildwood Collective now brings in over $100,000 in gross bookings a month on the 15 properties it manages, nine of which are client-owned and from which Wildwood collects 20% for its services in a revenue-sharing model.

They also consult on projects that other aspiring Airbnb entrepreneurs are seeking to launch, including scouting unique properties, outfitting them with on-trend interiors, and creating branding materials.

The Airbnb life does have challenges

Hudson and Krieger now face new challenges brought on by the pandemic and, perhaps, their own success. Home prices are up, and the competition for the few houses that are on the market has become more fierce, with all-cash buyers often favored over those who rely on financing.

The couple’s business thrived as they attained unique properties at lower price points once consistent with the area. Hudson said the pandemic has changed the market in the areas where they operate, not only as more travelers seek the kinds of Instagram-friendly accommodations they offer, but also as competitors notice their success and want to get into the business.

“It’s harder to do this now,” Hudson said. “The real-estate market is brutal. A lot of people want to do what we’ve done.”

Competition from other short-term-rental owners isn’t the only hurdle. For-sale properties just aren’t as plentiful as they once were. “We have tried to expand as quickly as possible as real estate becomes more scarce. Land is also hard to get now. Land used to sit for years, and now it’s a week,” Hudson said.

An interior view of Cedar Brook Cabin, a tiny house operated by Wildwood Collective.

Cedar Brook Cabin is one in the handful of tiny houses operated by Wildwood Collective.

Ethan Abitz

It’s become more challenging for the duo to find and invest in the unique properties that are their hallmark and that generate the kinds of returns they saw early in their operation.

“We wouldn’t have the same returns if we were lucky enough to beat out the 25 other investors on the modern house if we bought it today,” Hudson said.

All of the properties Hudson and Krieger own are financed, meaning they’re making monthly payments on them. But to compete in the market now, they said, you need to come with a cash offer.

The business also incurs operating expenses for maintenance and landscaping.

“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 that are being washed out,” Hudson said. “It’s a whole new level of upkeeping a property in areas like these.”

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 houses in Chester, Vermont, that rent for between $175 and $250 a night. It is, in Hudson’s words, the hardest project they’ve worked on to date but also one of the most rewarding.

It’s a concept they’re interested in expanding to other states like Maine or New Hampshire, though Hudson and Krieger also envision retiring from the hustle in five to 10 years by selling their business and moving West. Hudson said she’d like to flex her hospitality background in a different way by opening a farm-animal sanctuary that would also cater to ethical tourism and education. Krieger envisions working in marine-mammal preservation and responsible ecotourism.

That vision of the future may not be so far off, considering “we didn’t even have a business five years ago,” Hudson noted.

As for their 401(k), Hudson isn’t concerned. Business has been good to them, and the recent downturn in the market has made her feel sound in their investments.

“I think I’ve taken most of it out to do more projects,” Hudson said of their retirement savings. “This might sound a little overly confident, but I feel more comfortable making my own investments with real estate than investing in some magical fund that’s going to provide 3% returns.”

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