Airbnb

Sam's wife joined Airbnb as a mid-level manager and got rich on the stock

Sam's wife Sarah joined Airbnb around age 25 as a lower-to-mid-level manager when it had ~1,200 employees and was already worth billions. The stock appreciation made her a self-made multimillionaire before 30 without the stress of founding a startup.

“And before the age of 30, was worth— it was a multimillionaire because of the stock that appreciated from this thing, right? From joining Airbnb, right? So self-made multimillionaire, self-made multimillionaire without eating shit as a startup founder, right? Where you're stressed and you're making no money and you might fail all the time and all that stuff, and you have to make payroll and all that good stuff.”

Tusk Ventures: turn regulatory consulting into equity in Uber and Airbnb

Shaan profiles Bradley Tusk, an ex-policy operator who helped Uber fight taxi cartels and city regulators, then took equity that became one of the decade's best angel returns. He repeated it with Airbnb and built a $100M services firm paired with a venture arm.

“And then he got to invest and Uber was like one of the best investments of the decade for an angel investor. And he did that also with Airbnb, another group that had policy questions. And so any startup that had a regulatory or policy challenge, which actually many do, uh, it was like, oh, we should include Tusk in our round.”

Build Jungle Scout for second-tier marketplaces (Etsy, Poshmark, Airbnb)

Shaan's thesis: B-class marketplaces like Etsy, Poshmark, Mercari, and Airbnb have far less competition than Amazon. Build seller-tooling SaaS (à la Jungle Scout) on top of them, since the existing tools 'exist but they're not great.'

“So I'm really interested in the second tier or like what I'll call B-class marketplaces. I don't mean that as an insult. I mean it more like if you're in real estate, you're like, oh, do I buy an A, you know, A-class property, which is like it's a modern building, fully leased up, blah blah, or do you go for like an older thing that has upside, right?”

Steal thisFind a big marketplace where the third-party seller tools are weak, then build the 'Jungle Scout' for it.

AirDNA: bootstrapped to $9M revenue, possibly ~$30M ARR now

Sam reveals AirDNA, an Airbnb analytics tool he pays ~$100/mo for, did $4.9M revenue in 2018 and $8.4M in 2019 while growing 100%. It bootstrapped to $9M in revenue before raising just $8M — a seemingly 'small' tool that could be a $30M ARR business.

“In 2018, they did $4.9 million in revenue. In 2019, they did $8.4 million in revenue. They said they were growing 100%. So you could probably assume that I would, I would actually bet that in 2020 they probably did $16 million and then '21, I wouldn't be surprised because there's a lot going on with investing in Airbnbs.”

Airbnb photos as a lead-gen middleman business

Sam pitches airbnbphotos.com: since listing photos are the top driver of Airbnb performance, build a national Facebook-ad lead engine and take ~$25 per lead routed to local photographers. He saw a $200 photo shoot dramatically boost his own rental's traction.

“I definitely think you could have airbnbphotos.com or whatever it is, and that— and you take $25 for every lead that you send a photographer, and you could totally crush it that way, right?”

Steal thisRun national ads for a high-skill local service and sell each lead to local providers for a flat fee.

Altman's startup success formula: idea x product x execution x team x luck

Sam quotes Altman's 2014 Stanford class formula for a startup's odds: idea times product times execution times team times luck, where luck is a random number between 0 and 10,000.

“the formula for estimating a startup's chance of success is something like idea times product times execution times team times luck, where luck is a random number between 0 and 10,000.”

Side hustle type 2: own the supply side of an existing marketplace

Justin Mares's second side-hustle category: find a marketplace with existing demand (Airbnb, Amazon, Udemy) where you only have to provide supply. The platform finds the customers; you just learn its ranking rules and feed it inventory.

“look at what is a marketplace with existing demand where you don't have to go out and find the customer. You just provide the supply side stuff like buying, you know, putting a property on Airbnb. All I have to do is understand how does the property like, or how does Airbnb dictate where I rank, you know, and what does it want from me as a supplier? And then my shit is going to get booked up.”

Steal thisPick a marketplace that already has demand and become the supply, learning only its ranking algorithm rather than hunting customers.

The sharing economy basically only works for Uber and Airbnb

Sam argues from looking at the data that the sharing economy realistically only works for ride-hailing and home rentals, and maybe nothing else. Sharing tools, cooking lessons, or garage storage repeatedly fail because the inconvenience isn't worth the money.

“I am almost positive that the sharing economy only works for like 2 or 3 things: Uber and driving, um, Airbnb home rentals, and maybe that's it.”

Long-term sublease arbitrage: master-lease apartments, rent by the month

Sam describes Bill Smith's company Landing: lease whole apartments, then sublease them to people who want to stay a month-plus. The wedge is fees — Airbnb's ~10% fee makes a $10k/month stay cost $1k extra; undercut that and monthly nomadic living becomes normal.

“what it is is they lease out apartments in different places and they take the whole lease and then they sublease it because for people who want to stay for a month. And the thing about Airbnb is that they actually charge— what's the fee? 10% if you're staying for 2 weeks.”

Steal thisMaster-lease units and resell monthly stays, undercutting Airbnb's per-night fee structure for medium-term renters.

A retired cop's mafia crime walk grossed ~$1M on Airbnb

Sam does the math on an NYC Airbnb Experience: a retired NYPD officer's mafia and crime walk charges ~$120-130 and lists 8,000 guests served — roughly a million dollars.

“Second, he charges around $120 to $130 depending on the date per person, and in the description he says that he has had 8,000 guests. So $123 times 8,000 is a million bucks.”

Sam's portfolio: 90% index funds, concentrated HubSpot + Airbnb bets

Sam breaks down his actual holdings: bulk of liquid net worth in publicly traded HubSpot and Airbnb, the rest in the S&P 500, plus planned startup and real estate allocations. A rare candid look at how an exited founder actually invests.

“So right now the bulk of my liquid net worth is in publicly traded companies. Um, I own a bunch of HubSpot right now. I own a bunch of Airbnb. Besides that, I don't own anything else above $50,000. Uh, it's all in, um, so you're super concentrated in those two companies basically. Yeah, but then I have more money in the S&P 500.”

The 'Obama House' playbook: a celebrity Airbnb

Instead of a museum, Sam suggests a Jordan Airbnb. He points to the 'Obama House' near where he's staying — bought for $7M, now its own Wikipedia page — that rents on Airbnb for $6,000 a night or up to $180K a month.

“But they rent it out right now on Airbnb for $6,000 a night. Or if it's booked all the way up, $180K a month. And it's branded as the Obama House. I think that you could absolutely crush it with a Jordan Airbnb house.”

Steal thisBrand a property around a famous prior occupant and command a multiple on the nightly rate.

Peter Thiel's one-line advice after investing in Airbnb: don't fuck up the culture

Shaan recounts that when Peter Thiel put roughly $100 million into Airbnb in 2012, the founders asked his single most important piece of advice. Thiel replied with a one-line email: 'don't fuck up the culture.'

“That's like when Peter Thiel invested in Airbnb, I think he put like $100 million in or something like that. And this was back in 2012 where Airbnb wasn't super proven out. We're so glad to have you on board. You know, you invested in Facebook early on. You know, what's the single most important piece of advice you could give us? He just wrote back a one-line email that just said, don't fuck up the culture.”

Williamsburg house Airbnbs for $30K/month gross

Sam describes a friend, Ryan, who bought a nice Williamsburg house outright (no mortgage) and now Airbnbs it for $30,000 a month gross while living elsewhere.

“he bought this really nice house in Williamsburg. Have you seen it? Like, Ryan's like into architecture and he spent a lot of money on this great place and he's now in Miami or Delaware. He's all over the place and he, um, He's Airbnb-ing his place for $30,000 a month. He's making off of it. Gross, not profit.”

Stalk and Talk: reverse-engineer anyone's email with Rapportive

Sam describes a process he used to land an Airbnb interview: generate ~100 first+last+@domain email permutations in a spreadsheet, paste them into Gmail, and let Rapportive reveal which address surfaced the real social profile.

“And so I invented this thing, this process called stalk and talk. And the idea was I was going to use it to help me get a job at a company. I made this spreadsheet where I would put someone's first name, their last name, and then their URL, like @airbnb.com. And like, I would put Brian and then Chesky and then @airbnb.com, and it would give me like 100 possible combinations of what the name or his email could be. And then I would put it in Gmail and I would highlight each one and Reportive would tell me which email is his because it would show the social profiles related to each email. I ended up emailing the founders of Airbnb, an interview there using Reportive.”

Steal thisGenerate every plausible email permutation for a target, paste them into Gmail, and use an enrichment tool to spot which one resolves to a real profile.

Someone will make a fortune fully automating hotel check-in

Huber predicts that in 5 to 10 years someone will make a ton of money by fully automating hotels, eliminating the front-desk check-in process the way Airbnb already lets guests self-check-in via their phones.

“I think 5 years from now, 10 years from now, somebody's going to make a ton of money by totally automating hotels. Why the heck do you need that check-in process when we have the technology to do all of it on our phones?”

You don't need to join early — join the right pre-IPO company

Sam's wife joined Airbnb at ~1,000-2,000 employees (8 years into the company) and stands to make life-changing, 7-figure money at IPO. The lesson: being a mid-stage cog at the right pre-IPO startup can build serious wealth without founder-level risk or early timing.

“So 8 years into the business. So, you know, not gonna speak on it too much, but it sounds to me like by getting into the right company and not even at the right time, quote unquote, not even like early, you can make pretty life-changing amounts of money when that company goes public.”

Steal thisTo build wealth with less risk, join a high-trajectory pre-IPO company with real equity even if you're 'late' and just a cog.

Airbnb fired Sam the day before he started over a background check

Sam landed an Airbnb job around 2012 (he'd have been roughly the 300th employee) but was fired the day before starting because a background check flagged a reckless-driving case he hadn't disclosed, costing him potential public-offering upside.

“I actually, and then the day before I was supposed to start, they took my, they fired me because I had a criminal record and I wasn't truthful about it. And they found it on a background check. I wasn't not truthful. It's, I was still on trial for a reckless driving ticket and they found out.”

Waze for Wi-Fi: rate the actual internet speed at every Airbnb

Ben pitches a bootstrappable, possibly no-code site where remote workers upload a speed-test screenshot plus location for any Airbnb/VRBO, building a trusted database of real internet quality since listings only say 'has Wi-Fi.'

“And so, I'm thinking this is like a totally bootstrappable, maybe even no-code thing where you just say, hey, to get access to— it's basically Waze for Wi-Fi where whenever you're somewhere, You, you know, upload the geocoordinates. Maybe you put the address in. We'd have to figure out some security stuff around that, but you just take a screenshot of a speed test and then we just have this big database of all these different places and anyone who stayed there and the screenshots they've uploaded.”

Steal thisBootstrap a crowdsourced speed-test database for short-term rentals; monetize via Airbnb/VRBO affiliate links.

Why fixed-lease housing networks can't flex like Airbnb

Shaan's risk read on Landing-style businesses: because they sign fixed leases on every unit, their costs stay fixed even when demand drops, unlike Airbnb whose cost basis falls with revenue, leaving them exposed to vacancy gaps.

“You know, it's one of those, it's one of those situations unlike Airbnb, where for Airbnb, they don't pay to lease all the places. So when demand goes down, sure, their revenue goes down, but their cost basis also goes down. Whereas for these guys, their costs are going to be fixed, essentially, because they're going to be locked into all these leases. So they can't withstand kind of the normal demand fluctuations that other Airbnb-type site could do.”

Steal thisBefore backing an asset-heavy marketplace, check whether costs flex with demand or stay fixed through downturns.

The San Francisco rent arbitrage: live abroad for free

Shaan's playbook for living anywhere without moving: Airbnb your San Francisco apartment for more than your rent, then go live like a local in another city for 5-6 weeks, effectively for free. He did it in Buenos Aires.

“And the way that San Francisco works is like an arbitrage where you can Airbnb your house or your apartment and you could make more, you could literally live for free somewhere else in the world, you know, get a free vacation. So that's what I did. I went for 5 or 6 weeks. We lived in Buenos Aires, Argentina, and we just lived there like a local”

Steal thisAirbnb your high-rent home and live like a local in a cheaper city for free.

Covid will wipe out Airbnb hosts who bought places just to rent

Shaan predicts that hosts who bought or subleased properties purely to put them on Airbnb will be in trouble as Covid drops travel revenue to near zero, forcing defaults or conversions to long-term rentals.

“And so all those people now, there's this thing that was a moneymaker for a couple years has gone to zero. And so I think there's something very interesting that's gonna happen where what happens to all these hosts who got places just to Airbnb them, and now the Airbnb income has sort of totally dried up? Are they gonna default on their mortgages? Are they gonna default on the rent payments if they're, if they're subleasing? Or are they gonna turn into just normal rentals?”

Airbnb's founders became the photographers to fix ugly listings

Shaan retells the Paul Graham 'do things that don't scale' story: Airbnb was stuck with ~20 customers until Graham told them to go to New York where their hosts were. They personally shot professional photos of listings, lifting bookings, and that unscalable hack eventually became a real photographer fleet.

“they would tell their customers, hey, we want to do professional photos of your place. It increases bookings by 40%. Um, are you open to that? And then they would show up as the professional photographer and be like, hey, by the way, I'm the founder.”

Steal thisGo where your earliest customers physically are and do the unscalable manual work that fixes their biggest problem.

The Bezos hiring question: how lucky do you think you are, 1 to 10?

Sam shares the interview question Joe Gebbia asked him at Airbnb, originated by Jeff Bezos: how lucky are you on a scale of 1 to 10. The logic is that people who consider themselves lucky are either genuinely talented or attract good outcomes, and those are the people you want around you.

“people who, uh, say they're really lucky are the people I wanna be around. Right. I was like, why do you think that? And he goes, well, if you're lucky, if you think you're lucky, you must be talented and things just fall in your place or you actually are lucky. And I wanna surround myself with lucky people.”

Steal thisAsk candidates how lucky they feel on a 1-10 scale; favor the optimists who can explain why.

Shaan got an Airbnb offer rescinded for lying about his criminal record

Shaan got early job offers at Uber and Airbnb (first ~100 employees); one offer was rescinded after he lied on his resume about having a criminal record, and he was told not to come to work on Monday after already moving out for the job.

“I had job interviews at Airbnb and Uber early-ish, first 100 people. And, uh, one of them I got employed, one of them I got the offer, but then they rescinded it because I lied about my resume. And the other one I didn't get past the What did you lie about? I had a criminal record and I told them I didn't. Okay, so I moved all the way out here. I moved all the way out here and they're like, oh, all right, uh, don't come to work on Monday.”

The Craigslist Unbundling: every category is a billion-dollar startup

Shaan explains the famous 'Craigslist unbundling' diagram: each category on the homepage (shared housing → Airbnb, apartments → Zillow/Trulia) spawned a specialized standalone company. Hundreds of successful businesses were built by taking one Craigslist feature and going deep.

“And so you can just see how many different businesses just realized that, hey, if there was demand for it on Craigslist, maybe we could build a specialized version for— of just that one feature. We could build a whole site of just that one service that it's offering. And there are like hundreds that are in this.”

Steal thisPick one category on a giant horizontal marketplace and build the best specialized vertical version of just that.

How Airbnb seeded supply with fake personas and Craigslist scraping

Shaan recounts Airbnb's early growth hack: they scraped Craigslist rental listings to auto-create Airbnb listings, then went further by emailing every Craigslist host as fake personas like 'Linda,' insisting they'd only book via Airbnb — pressuring hosts to join.

“They started creating fake personas, Linda or Cindy or whoever it was, and they would go and they would email every listing that was up for rent on Craigslist, and they would say, "Hey, I'm super interested in this."”

Great investments look unclear at the start, then get a retrofitted narrative

Daniel Gross argues the best deals are tenuous at the beginning (Airbnb almost didn't get into YC, Stripe had no proper batch) and that media teams later retrofit a tidy origin story.

“I actually think all good investments at the beginning are super unclear. A lot of the great YC darlings almost didn't get into YC. Airbnb was super on the fence. I mean, even Stripe didn't properly do— I see there's no actual batch they participated in. And this is the truth about the world, I think, is a lot of the stuff that is great always starts humble and small. Then of course their media teams get together and retrofit the whole narrative”

Rebuild Product Hunt entirely in a no-code tool as a marketing stunt

Discussing no-code tools like Parabola and Voiceflow, the pair float rebuilding a full app — Airbnb, Twitter, or even Product Hunt itself with all its logic, database, upvoting and comments — using only no-code tools, which Vlad calls a good marketing idea.

“Like rebuild Product Hunt itself, right? In a no-code tool, right? Where you're, you're doing all the logic, all the database stuff, all the like visual components, all the kind of state changes, upvoting, comments. Sounds like a good marketing idea for you guys.”

Steal thisProve your no-code tool's ceiling by publicly rebuilding a famous app with it.

The art of business is the things that don't scale

Belsky's signature insight from The Messy Middle: founders avoid unscalable work as a waste of time, but the things that distinguish a brand are precisely those that don't scale, like Airbnb sending photographers to every apartment.

“The art of business is the things that don't scale. And then it's like, okay, what is that? Right. Unpack that. Yeah, unpack that. And so that will be like a 2 or 3 page section about how we sort of perseverate over all the science nuances. And actually our instinct is to not want to do anything in our businesses that doesn't scale because we feel like that's a waste of time. When in fact, a lot of the greatest examples of distinguishing a brand or a service are the things that don't scale, like Airbnb sending out photographers for every apartment.”

Steal thisIdentify the deliberately unscalable thing only your company does, and protect it as you grow.

The all-in trait that fuels addiction also fuels entrepreneurship

Sam frames the same obsessive, go-all-in personality that made him an alcoholic as the engine behind his entrepreneurial success. He treats extreme tendencies as a trait to channel, not just suppress.

“I love to go all in on stuff. I get obsessed about things. I can get addicted to things very easily, and those attributes are also what can be part of being an alcoholic and having substance addictions. And I had that and I overcame it and I wanted to talk about that. And interestingly, what made me addicted to alcohol is actually what has made me a pretty successful entrepreneur”

Steal thisChannel your all-in obsessive streak into your work instead of letting it run your vices.

A brand is the story it tells

Brian Scudamore's core branding principle: whether Starbucks, Airbnb, or 1-800-GOT-JUNK, a brand is the story it tells and the hard part is living up to it.

“I think I realized early on in building a business that a brand is the is the story that it tells. Now, as a brand, whether you're Starbucks or Airbnb or 1-800-GOT-JUNK, you have to live up to the story.”

Steal thisDefine the story your brand tells, then build operations that live up to it.

The science of business is scaling; the art is what doesn't scale

A core Messy Middle insight: instinct says avoid anything that doesn't scale, but the things that distinguish a brand are precisely the unscalable ones — like Airbnb sending photographers to every apartment. The challenge is preserving that 'art' as you grow.

“Like, an example is the science of business is scaling, the art of business is the things that don't scale. And then it's like, okay, what is that, right? Yeah, unpack that. And so that will be like a 2 or 3 page section about how we sort of perseverate over all the, the science nuances. And actually our instinct is to not want to do anything in our businesses that doesn't scale because we feel like that's a waste of time, when in fact a lot of the greatest examples of distinguishing a brand or a service are the things that don't scale, like Airbnb sending out photographers for every apartment.”