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The Slacker's Guide to Getting Rich(ish)
Remember when we thought we'd retire at 55 with a gold watch and a pension? Yeah, that worked out about as well as Crystal Pepsi. Now we're staring down our 50s wondering if our neXt chapter involves greeting people at Walmart or actually building something for ourselves. Enter real estate – specifically Airbnb – where Gen X can finally put cynicism & pragmatism & HGTV together as was always intended.
What to expect: We breaking down Airbnb investing for people who grew up with both MTV and mortgage crises. We'll explore the all-in approach for overachievers and the slacker method for those who'd rather not add "toilet unclogger for a house we don’t live in" to their resume.
The Heavyweight Approach: For Those Who Didn't Get Enough Homework in School
Remember how your parents bought a house for like $30,000 in the '70s and now it's worth half a bazillion? (My parents bought for $33K in 1972 - that house sold for $853K last year - and that wonky ceiling still makes my former bedroom barely usable…) That ship has sailed, capsized, and sunk to the bottom of the ocean. But the Airbnb economy offers a consolation prize if you're willing to become a responsible adult with property responsibilities (OMFG, that does sound terrible, doesn’t it?).
What the Heavyweight Option Involves:
Property acquisition - Convincing a bank you're trustworthy despite that regrettable credit card situation from 1997
Property preparation - Spending weekends at Home Depot instead of binging Stranger Things
Listing creation - Pretending your photography skills have improved since your MySpace days
Day-to-day management - Becoming a concierge on par with Monsieur Gustave H. in The Grand Budapest Hotel
Property maintenance - Finally learning what all those tools in your garage actually do. Quick question - who’s better - Schnieder from One Day at a Time or Norm Abram from This Old House? Very tough call.
Financial management - Spreadsheets. So. Many. Spreadsheets. 🤮
Real-World Example: The Smoky Mountain Cash Machine
While you are probably wondering what’s going to transpire next between Gavin Newsom & DJT, savvy investors like The Short Term Shop are snatching up cabins in Gatlinburg, Tennessee. A standard 3-bedroom cabin there costs around $400,000 but can generate $75,000-$100,000 in annual revenue. That covers your mortgage & leaves a little cheddar for your back door Roth IRA, I think.
Pros of Direct Ownership
Higher potential returns - Like finding a mint condition X-Men #1 in your parents' attic
Complete control - Channel your inner control freak without therapy (tho therapy is still an option…)
Building a tangible asset - Unlike your 401k that undulates with every Truth Social post or jobs data report.
Tax advantages - Stick it to The Man the legal way
Personal satisfaction - Tell everyone at your high school reunion you "own investment properties" (while omitting the part about unclogging strangers' toilets)
Flexible use - Have a free vacation spot when your guests aren't trashing it
Cons of Direct Ownership
Six-figure startup costs - About the same as four years at the college your kid wants to attend
24/7 availability - Remember being on-call for your newborn? It's like that, but the baby is a house
Learning curve - Steeper than figuring out TikTok to spy on your teenagers
Market volatility - One pandemic and suddenly your investment strategy is as outdated as your CD collection
Regulatory risks - Cities changing short-term rental laws faster than Taylor Swift changes eras
Concentration risk - Putting all your eggs in one basket worked great for Enron, right?
How 433 Investors Unlocked 400X Return Potential
Institutional investors back startups to unlock outsized returns. Regular investors have to wait. But not anymore. Thanks to regulatory updates, some companies are doing things differently.
Take Revolut. In 2016, 433 regular people invested an average of $2,730. Today? They got a 400X buyout offer from the company, as Revolut’s valuation increased 89,900% in the same timeframe.
Founded by a former Zillow exec, Pacaso’s co-ownership tech reshapes the $1.3T vacation home market. They’ve earned $110M+ in gross profit to date, including 41% YoY growth in 2024 alone. They even reserved the Nasdaq ticker PCSO.
The same institutional investors behind Uber, Venmo, and eBay backed Pacaso. And you can join them. But not for long. Pacaso’s investment opportunity ends September 18.
Paid advertisement for Pacaso’s Regulation A offering. Read the offering circular at invest.pacaso.com. Reserving a ticker symbol is not a guarantee that the company will go public. Listing on the NASDAQ is subject to approvals.
The Lightweight Approach: For Those Who Want Money Without Actually Working
If your idea of property management is remembering to water your houseplants, there's still hope. You can get some yummy investment income via Airbnb without ever having to wash someone else's sheets.
Ways to Invest Indirectly:
1. Airbnb-focused REITs (Real Estate Investment Trusts) Like buying a stock, except instead of owning a piece of a company that makes electric cars that may or may not explode, you own a piece of a company that owns a bunch of houses. Check out Invitation Homes (NYSE: INVH) or American Homes 4 Rent (NYSE: AMH) – they're not exclusively short-term rentals, but they're dipping their toes in the water.
2. Fractional ownership platforms Remember timeshares? This is like that, but potentially less of a scam and with actual returns instead of a week in Boca you never use - its a shame you never pulled the trigger on that 1 br at Del Boca Vista, tho. Platforms like Arrived let you buy shares of rental properties for as little as $100, while Here lets you purchase fractional ownership in vacation rentals specifically.
3. Private equity funds For when you want to feel like Gordon Gekko without the insider trading charges. Firms like Vacasa (NASDAQ: VCSA) manage over 35,000 vacation homes across North America, Belize, and Costa Rica (and you can book AirBnB stays there too - some of these digs are SWANKY.
4. Host-partnering arrangements You bring the cash, they bring the elbow grease. It's like having a teenage kid who actually does their chores. Companies like AvantStay partner with property owners to manage and optimize short-term rentals while sharing the revenue.
This Is How It Might Work IRL: The Fractional Beach House
A group of six friends (who met at a Pearl Jam concert, natch…) pool $300,000 to purchase a beach cottage in Outer Banks, NC. Instead of arguing over who gets which week in summer (and inevitably ending friendships), they form an LLC, create a formal operating agreement, and hire a professional management company. Each member gets six weeks of personal use annually, and they split profits after expenses. You can use that profit to ramp up another property, or Scrooge McDuck it.
Pros of Indirect Investment
Lower entry point - Start with the money you were going to blow on that midlife crisis motorcycle
Diversification - Not putting all your chips on red (we learned that lesson at Casino Night at the kids school - remember?)
Truly passive income - As passive as pretending to listen to your cubicle neighbor while thinking about lunch
Professional management - People who actually know what they're doing (a novel concept)
Liquidity options - Easier to bail than that gym membership you've had since 2010
Simplicity - About as complicated as setting up a Roku, which you can probably handle
Cons of Indirect Investment
Reduced returns - The price of not having to explain to guests why the WiFi isn't working at 2AM
Limited control - You might not like being hands off - you didn’t cosplay as Monica Geller accidentally, did you now?
Dependency on managers - Trusting strangers with your money (what could go wrong - is it wrong to mention Enron again?)
Less tax efficiency - Uncle Sam always finds a way to crash the party - word has it that passive income from real estate is taxed more than any billionaire that we know is…
Platform risk - Some of these companies have been around for less time than your favorite pair of jeans - so buyer beware
Regulatory uncertainty - Laws written are often written by people who flipped the f&#k out when AOL pulled the plug on dial up
Which Approach Suits Your chapterneXt?
Your choice probably says as much about your personality as whether you were Team Coke or Team Pepsi, you wanted to be a Shark or a Jet, or a Greaser or a Soc.
Anyhow, when deciding between heavyweight and lightweight Airbnb investing, ask yourself:
Financial situation: Is your bank account more "Champagne Supernova" or "Mr. Brightside"?
Time availability: Do you have time to manage a property, or are you still trying to finish Ozark (no spoilers - but you gotta finish…)?
Risk tolerance: On a scale from "still has that US Savings bond from. Grammy" to "bought Bitcoin at $36K & sold at $32K”?
Personal interests: Are you Paige Davis from Trading Spaces, or “I will stop using old CHiPs & Happy Days posters as wallpaper - maybe”?
Timeline: Are you planning for next year or for when Social Security inevitably collapses? (Wait - those could be the same thing…)
Location: Do you live somewhere tourists actually want to visit, or in a town whose claim to fame is a really big ball of twine?
Expert Resources Worth Your Time
If you're thinking, "This all sounds great, but I need actual adults to guide me," here are some resources that won't waste your time:
Books That Don't Suck:
Short-Term Rental, Long-Term Wealth by Avery Carl - Written by someone who actually owns 100+ properties, not some guru selling courses from their mom's basement.
Airbnb for Dummies by Symon He and James Svetec - Because we're all dummies when we start something new, might as well embrace it.
Podcasts for Your Commute:
Get Paid for Your Pad with Jasper Ribbers - Over 400 episodes of actual tactical advice from hosts who don't just talk the talk.
The Short Term Show with Avery Carl - No-nonsense insights from the queen of short-term rentals in vacation markets. Her latest was about VA loans - which are a real boon for anyone who had the good luck to be in the service (yep! thats still AWESOME)
TLDR: Less Reading, More Doing
While your Gen Z coworkers are buying virtual land in the metaverse, you could be building a real estate portfolio that actually produces income. Whether you go all-in with direct ownership or take the slacker route with indirect investments, the Airbnb ecosystem offers legit opportunities for us Gen Xers and Gen X-adjacents to craft our chapterneXt.
Just remember: We're not financial advisors (or life coaches, therapists, or psychics). We're just fellow middle-aged folks trying to figure out how to retire without having to eat cat food. Do your own research, consult professionals, maybe finally read some of those emails from your 401k provider.
Most importantly, get started. Because unlike your high school jeans, financial independence might actually fit you one day.
Clearing the Path Forward
Ready to channel your inner Property Brother or Wolf of Wall Street? Here's how to get started:
For the heavyweight approach:
Research high-performing Airbnb markets (hint: not where you vacationed in 1992)
Find a real estate agent who doesn't use a Hotmail address
Talk to actual Airbnb hosts (buy them a drink first; they need it)
Learn local regulations (as exciting as reading the manual for your VCR was)
Do math that doesn't involve calculating how many beers you can afford
For the lightweight approach:
Research REITs and platforms while pretending to work
Compare fees (they're all highway robbery, just pick the least offensive)
Start small (remember when you invested your life savings in Beanie Babies?)
Diversify (unlike your music taste, which stopped evolving in 1999)
Set up a system to track performance (more sophisticated than the notebook where you track which neighbors haven't returned your lawn tools)
Your chapterneXt doesn't have to involve greeting people at Costco or moving in with your adult children. Whether you go all-in or barely-in on Airbnb investing, the important thing is that you're building something besides another IKEA bookshelf.
Ready to stop watching House Hunters and start living it? Drop a comment about which approach sounds less terrifying, or share your own horror story about that time you tried to fix a leaky faucet and flooded your basement. We're all in this midlife crisis together.