How a Millennial Couple Built an Empire of 15 Airbnbs in 4 Years

  • Lauren Hudson, 40, and Chris Krieger, 39, bought a modern Vermont cabin as a second home in 2017.
  • They turned to Airbnb to cover the costs, then left their day jobs to run Airbnbs full time.
  • The collective now has 15 properties, generating over $100,000 in gross bookings per month.

The Vermont cabin that Lauren Hudson and Chris Krieger bought in 2017 for $235,000 was supposed to be a vacation home they occasionally rented out 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 scenario, sell it if their aspirations didn’t come true. Instead, the property has been so successful on Airbnb that the couple have had to start blocking weekends out of the rental schedule.

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

They hadn’t anticipated how lucrative short-term rentals could be. At the cabin’s closing table in August 2017, the seller’s agent and theirs said the couple could expect to earn $15,000 in vacation rental income per year. The first year, they brought in more than their $2,000 per month holding fee. In 2018, they brought in $62,000 in revenue. By 2021, that figure had nearly doubled to $115,000.

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

The company’s success saw both Krieger, a former CPO of a midsize consumer credit union, and Hudson, once creative director of a global market research firm, quit. their daily job to work full-time on their Airbnb scramble.

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

The couple explained how they succeeded.

It all started with finding a vacation home

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

“It was kind of a mental health project for me. I really missed that connection to nature and I was getting some peace and quiet,” she said.

It was also Hudson’s west coast inclinations that drew them to the property they named the Green Mountain Modern House, a clash of contemporary architecture that looks more like Joshua Tree than a cabin nestled in the trees. Jamaica Wood, Vermont.

A rectangular house sits on a wooded lot.  The house is lit from inside when the sun sets outside.

Hudson and Krieger bought the Green Mountain Modern House for $235,000 in 2017. It was 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 good investment. The couple were so convinced they liquidated part of their 401(k) to earn $30,000

advance payment


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

“Airbnb didn’t really 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 blown away by the demand there was,” she said. “He was continually booked. We couldn’t find enough time for ourselves.”

The House rent now for around $442 a night.

“We keep the cash flow towards expansion”

Demand drove them to buy a second property (then a third, and so on).

Hudson and Krieger decided to buy and rent a tiny house the same way they chose Green Mountain Modern House: it reminded them of experiences on the West Coast.

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

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

It is located on land near the Green Mountain Modern House which they rent for around $700 a month.

“We’re keeping the cash flow toward expansion,” Krieger said.

A blue A-shaped house sits among the trees.

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

Ethan Abitz

And continue to grow, they did. The idea of ​​starting Wildwood Collectivetheir vacation property marketing and management company, took off with its third purchase, a $130,000 A-frame in nearby Wilmington, Vermont, in February 2020.

Over the previous three years, the duo had noticed an appetite for properties being sold as stand-alone businesses, so after investing $20,000 in the A-frame upgrade, Krieger put it up for sale as that vacation rental with marketing assets for $330,000.

It took the property a month to find an off-market buyer who “became our best and most trusted partner” in expanding the properties they manage as part of the collective, Hudson said.

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

They also consult on projects that other budding Airbnb entrepreneurs are looking to launch, including finding unique properties, outfitting them with on-trend interiors, and creating branded materials.

Airbnb life has its challenges

Hudson and Krieger now face new challenges posed by the pandemic and, perhaps, their own success. Home prices are on the rise and competition for the few homes that are on the market has become fiercer, with cash buyers often favored over those dependent on financing.

The couple’s business flourished as they secured unique properties at lower prices, once compatible with the area. Hudson said the pandemic has changed the market in the areas where they operate, not only as more travelers seek out the types of Instagram-friendly accommodations they offer, but also as competitors notice their success and want get into the business.

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

Competition from other short-term rental owners isn’t the only obstacle. Properties for sale simply aren’t as plentiful as they once were. “We have been trying to grow as quickly as possible as real estate becomes scarce. It is also difficult to get land now. Land had been sitting for years, and now it is a week,” said Hudson said.

An interior view of Cedar Brook Cabin, a small home operated by Wildwood Collective.

Cedar Brook Cabin is one of the few cottages operated by Wildwood Collective.

Ethan Abitz

It has become more difficult for the duo to find and invest in the unique properties that are their hallmark and that generate the kinds of returns they saw when they first started operating.

“We wouldn’t have the same returns if we were lucky enough to beat the other 25 investors in the Modern House if we bought it today,” Hudson said.

All properties owned by Hudson and Krieger are financed, meaning they make monthly payments on them. But to be competitive in the market now, they said, you have to present a cash offer.

The company also incurs operating expenses for maintenance and landscaping.

“Let’s say you own property in New Jersey or New York – owning property in Vermont is completely different. You’ve never had to deal with septic and rural storms and roads that wash out,” Hudson said. “It’s a whole new level of maintaining a property in areas like these.”

They’re not here for the long haul

In October 2021, Wildwood Collective opened Camp Wildwood, a pet-friendly vacation enclave of two tiny homes in Chester, Vermont that rent for between $175 and $250 a night. It is, in Hudson’s words, the most difficult project they have worked on to date, but also one of the most rewarding.

It’s a concept they want to expand to other states like Maine or New Hampshire, although Hudson and Krieger also plan to retire from the turmoil in five to 10 years by selling their business and moving to the West. Hudson said she would like to flex her hospitality experience in a different way by opening a farm animal sanctuary that would also cater to ethical tourism and education. Krieger plans to work in the preservation of marine mammals and responsible ecotourism.

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

As for their 401(k), Hudson is not concerned. Business has been good for them and the recent market downturn has made him feel good about their investments.

“I think I took most of it out to make more plans,” Hudson said of her retirement savings. “It may sound a bit overconfident, but I feel more comfortable making my own investments in real estate than investing in some magic fund that will deliver 3% returns.”

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