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Brian Chesky is no stranger to starting a business in tough economic times.
Chesky cofounded Airbnb in 2007 and built the business during the 2008 financial crisis. In a recent podcast conversation with Michelle Obama and her brother, Craig Robinson, Chesky said it was challenging to get the business off the ground during a recession, even with some of the advantages and connects he and his founders had that other entrepreneurs might not have.
However, he said there was one "silver lining" to growing the business during tough times, which might resonate with founders facing today's economic uncertainty.
"A lot of great companies have been started in a recession," he said in a Wednesday episode of "IMO with Michelle Obama & Craig Robinson."
"And the one, I don't want to say it's a good thing, but what it does is it teaches you a certain type of discipline," he said. "A tough economy teaches you a discipline that gets institutionalized into your culture."
By comparison, a strong economy might give founders more cushioning to "perpetuate bad strategies and be a little less disciplined," Chesky said.
"I think the good news is a lot of great entrepreneurs are incredibly resourceful, and they will find a way to work," the Airbnb cofounder said. "But we absolutely need like a very stable economy."
Chesky said that entrepreneurs he's spoken with recently told him "a lot of fundraising, for all intents and purposes, was kind of on hold."
"A lot of limited partners and investors are just like hunkering down. And what we know about investors, they don't like uncertainty," he said.
He believes investors will "sit this one out until things stabilize."
"And if they don't stabilize, we're going to be in for a very prolonged kind of dry spell for fundraising," he said. "If you did not go to a prestigious school, if you weren't, like, purely a team of technical engineers, if you're not trying to create an AI company, you're just trying to create a business, that will be more difficult."
Airbnb isn't the only successful business to emerge from the Great Recession. Companies like Uber, WhatsApp, Venmo, and Square also started around the time of the 2008 financial crisis.
"It's always a great time to start a business — and some of the most successful businesses are started during recessions," certified financial planner Cary Carbonaro previously told BI. "Adversity is the mother of invention."
Airbnb
Airbnb is trying to expand beyond just vacation rentals — and it's enlisted some celebrities like Megan Thee Stallion and Patrick Mahomes to get some buzz going for its new offerings.
I have some questions.
It seems like these big names are only here to tout the new "Experiences" — things like throwing the pigskin with Mahomes or hanging out with Megan for the day. These all cost nothing, but go to only a handful of contest winners.
The celebs are obviously only going to be around for this promo period. After that, are people going to turn to Airbnb for a day tour of Philadelphia or a cooking class in Honolulu? Maybe. I have my doubts.
Meanwhile, another one of Airbnb's launches — called "Services" (think private chefs and photographers) — could make a lot of sense for people on vacation who need to find a trusted … well, service person.
There's also something big in all of this for Airbnb: your data. More on that later.
For now, let's look at a couple of these "Airbnb Originals" that are part of its new Experiences.
Toss a football and have a barbecue lunch with the Chiefs quarterback at a rental cabin near Kansas City.
Only four people (and their plus-one ) will get to do this.
Airbnb
This is the most exciting option (to me), but also one of the more confusing ones. Twelve winners will get to make ramen with the rapper, dress up in a costume, and play Xbox with her.
The description of the actual run of events looks like this:
Airbnb
There are a handful of other slightly less famous celebrity experiences that do charge. Brooklyn Peltz Beckham (son of David and Victoria, son-in-law of billionaire businessman Nelson Peltz) offers a cooking demonstration for $150 per guest. Pro wrestlers Nikki and Brie Garcia offer a chance to sit in on their podcast taping for $195. Chance the Rapper is having a listening party for $110.
A rep for Airbnb told Business Insider that pricing was up to the celebrity and that another A-list celebrity would soon be doing a paid event, with the fees going to charity.
There's a disconnect here between these star-studded promotional things and the new Experiences Airbnb is trying to promote. These are largely contests to win a free prize, not an experience or service you pay for.
It's not unlike a classic radio station contest where the 25th caller gets to meet Paul Stanley, or the 1990s MTV contests where suburban teens can win the chance for a big band to perform in their backyard.
The actual product Airbnb is launching is more practical and down-to-earth: high-quality tours and food experiences from vetted providers.
Even charging a nominal amount makes these celebrity experiences very different. Airbnb subsidizes the event, likely cutting the celebrity a big check to participate. This is a different business model from the regular tour guides, who make their money from customers.
Well, there is something that makes sense about all of this. I figured it out when I started the process to sign up for Megan Thee Stallion's event on the Airbnb app.
It's about getting your sweet, sweet data.
As part of my application process, I was asked to continue to fill out my user bio — adding things like my favorite song from high school, my hobbies, where I went to school, and my pet's name (as a tech journalist, I must warn you here not to put information in a public bio that is commonly used for password reminder questions).
Tens of thousands of people want to hang out with Patrick Mahomes and Megan Thee Stallion. Only a handful will get to, but many will fill out their expanded bios, giving Airbnb lots of information on prospective users.
Airbnb
These expanded bios are part of Airbnb's new ambitious rebrand: to be a place not just for vacation rentals, but for people to hire other people for anything. And part of that is building out is convincing customers to make personalized bios, so that the vendors can better see who they're dealing with and vice versa.
I think the new feature called Services actually seems like a great idea — things like a hair stylist or makeup artist to come to your home or Airbnb rental for a big event are the kind of things people only want once in a while. And it will certainly open up tons of opportunities for chefs, trainers, stylists, etc., to get themselves in front of more clients.
But the Experiences? I'm not sure what this will all look like in a year after the celebrity buzz has died down.
Darrel Maxam and Patrice Maxam
When Darrel and Patrice Maxam moved from Connecticut to Georgia, they bought a 1956 bungalow for $249,400. Because they'd used most of their money to buy the home, they struggled to afford the $1,400 monthly mortgage payments.
"When we moved to Atlanta, we were really broke," Darrel Maxam told Business Insider. "We literally spent all of our money on a down payment — we had $1,000 in our bank accounts."
They decided to list a bedroom in the three-bedroom bungalow on Airbnb. Then they rented the entire house. Later, they began renting out a tiny house on the property. Eventually, the Maxams filled their two-and-a-half acres with nine different short-term-rental units: the main house, a tiny home, a converted barn, a triplex, and three "treehouses."
Darrel Maxam.
Now, the Maxams build and operate short-term rentals full-time. They sold the Atlanta property in September of 2024; Fulton County property records show it sold for $655,000. Their focus is a village of 13 custom-built cabins and properties in upstate New York that brings in between $30,000 and $60,000 a month.
Read on to see how the Maxams built their Airbnb empire.
Renting out rooms brought in about $1,000 a month in profit, Maxam said, and renting out the entire home doubled that amount.
Maxam recalled packing up every weekend during the summer and vacating the premises while Airbnb guests were staying in their Atlanta home.
He said the couple would take 10% of his weekly paycheck, 10% of his wife's weekly paycheck, and 10% of the amount they were making from Airbnb and use it to find a hotel within 300 miles that worked within that budget.
"If we only had $400, we were going to plan a trip for $400," he said. "We would go as far south as Destin, Florida, as far east as Mississippi, and as far north as the Carolinas and Tennessee area."
Maxam figured the more units they put on the Atlanta property, the more money they would make.
First, the Maxams partnered with the HGTV show "Tiny House, Big Living" to build a tiny home on their property, which Maxam said earned them an extra $2,500 a month in profit.
"I was hooked at that point," Maxam said. "We had a barn in the backyard. I converted that barn to another livable space. Then, another year after that, I ended up building three more units. After the fifth unit on the property, we were generating roughly $15,000 a month."
At one point, the Maxams had their main house, a tiny home, a barn, a triplex with three rentable units, and three treehouses on the property. They took the tiny home with them when they left.
Patrice Maxam and Darrel Maxam
Maxam resigned from his full-time job working for the Department of Aviation and made hospitality his career.
In 2022, the Maxams' main project became Finger Lakes Treehouses in Sodus, New York, a small town 33 miles east of Rochester.
Courtesy of Darrel Maxam.
They partnered with Red Falls Timber, a New York-based firm that sources its wood from Finland, to build five A-frame cabins.
Each one has a kitchenette, a bathroom, air conditioning, and a private wood-fired hot tub. Nightly rates are around $250, according to the Maxam Hotels website.
Each A-frame structure cost him about $65,000, Maxam said. Since launching in 2023, the five cabins have brought in anywhere from $30,000 to $60,000 a month, he added.
Courtesy of Darrel Maxam.
"We don't touch a project unless we can be cash-flow positive within 18 months," he said.
The Maxams are planning to build five non-A-frame cabins with Red Falls Timber on the Sodus land this year.
Both cabin styles are prefabricated, which means they can be put together quickly, cutting down on both time and cost per unit.
"It'll take about three days to get them erected," Maxam said.
"You, right now, can come on site, look at my plans, and be able to put my building together," he added. "That's how easy they are — they're like Lego."
The Maxams have other dreams for the Sodus development.
"We have three Airstreams on the property right now, so by the start of the season, we'll have 13 units total," Maxam said. "Next year, we're going to go into phase three. We have these really luxury-style safari tents, and we'll build a bathhouse for them, also."
The plan is to have 19 total units in Sodus by next year, he added.
Courtesy of Darrel Maxam.
The couple has also purchased land in Belize with plans for a beach-centered venture in 2026 or 2027.
The Maxams entered the short-term-rental world humbly, but now feel like they are thriving.
Maxam said to get here, they took their time, using proceeds from one unit to build the next one.
"Everyone wants to rush and rush and race to do the largest project — and they don't know what they're getting themselves into," Maxam said.
"The only advice I have to someone starting out like me is to stay small enough, long enough, because soon enough you'll be big enough," he added.
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