• Airbnb's CEO said he's heard from founders facing a challenging fundraising landscape amid economic uncertainty.
• Brian Chesky said that while a stable economy is needed, there's a "silver lining" to building a business in tough times.
• The Airbnb cofounder said on Michelle Obama's podcast that a tough economy bakes "discipline" into your company culture.

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 has an ambitious new plan to help you book anything.
• It's using celebrities like Patrick Mahomes to promote its new "Experiences."
• Those "Experiences" aren't quite like the ones you'll actually book — but its new "Services" seem useful.

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.

Spend a Sunday Funday with Patrick Mahomes

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.

Become an Otaku Hottie with Megan Thee Stallion

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:

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.

How to actually win these free experiences

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.

A prompt to fill out your user bio with more information

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.

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.