How Rob Made $100K from 3 Airbnbs While Working a 9-to-5 and Raising Two Kids (2025 Case Study)
Preston Seo
Rob earns over $100,000 per year from 3 Airbnb arbitrage properties while working a 9-to-5 job and raising two kids. Starting with his MBA nearly complete and looking to deploy his savings into something meaningful, he joined Legacy Investing Show in August 2020 and had his first property under lease by October. Today, Rob manages properties in Louisville, Kentucky and St. Simons Island, Georgia, with systems so automated he barely thinks about the business day-to-day.
This case study breaks down exactly how Rob built this Airbnb arbitrage business, including his specific strategies for convincing landlords, setting up properties remotely without ever visiting them, and creating automated systems that let him balance work, family, and entrepreneurship.
In this article:
Quick Results: Rob's Airbnb Arbitrage Numbers
| Metric | Value | Context |
|---|---|---|
| Annual Revenue | $100,000+ | Year one gross revenue |
| Properties | 3 | Louisville KY & St. Simons Island GA |
| Q1 2024 Revenue | $92,000 | On track to exceed prior year |
| Time to First Property | 2 months | Joined August, lease signed October |
| Time to Go Live | 5 months | First booking in January |
| Scale Timeline | 1 year | From 1 to 3 properties |
| Management Time | Minimal | Automation handles day-to-day |
| Employment Status | Full-time 9-to-5 | Plus raising two children |
Rob's Background: From MBA Student to Airbnb Entrepreneur
You don't need to quit your job to build a successful Airbnb business. Rob is proof: he built a six-figure Airbnb arbitrage business while working full-time, finishing his MBA, and raising two kids. His background demonstrates that the right systems and strategies can make this business truly passive.
The Discovery of Airbnb Arbitrage
In mid-2020, Rob was finishing up his MBA and looking for ways to deploy his savings into something meaningful. He had already started one business alongside his 9-to-5 and kept seeing Preston's videos on Instagram about what he calls "the bridge method" - Airbnb arbitrage.
The concept immediately appealed to Rob because it represented a relatively low-risk entry point into real estate. Unlike buying property, which requires massive down payments and ties up capital, arbitrage let him test the business model with limited exposure. After researching the opportunity, he decided to join Legacy Investing Show in August 2020.
"It's like anything that you jump into - you can sit on the sidelines and try to speculate how it's going to go, what you need to be prepared for. Just take that first step. We bumped our heads along the way but we figured it out."
Finding a Turnkey Airbnb Property
Rob's first property was a stroke of strategic luck. He initially researched several markets in Florida where he had family, found plenty of properties, and even got agreements from landlords. But ultimately, he pulled back to his home base of Louisville, Kentucky.
What he found there was remarkable: a property where the owners had already run it as an Airbnb. Unfortunately for them, they launched in February 2020 - possibly the worst timing in history as travel ground to a halt. They pivoted to long-term rentals, but the property remained fully furnished and set up for short-term rental operations.
When Rob pitched them his idea, they immediately understood the model. Even better - they had already gone through the permit process, so Rob didn't have to worry about any of that. The property was essentially turnkey, requiring minimal upfront investment to go live.
That first deal set a tone for Rob's approach: find opportunities where much of the work is already done, focus on creating win-win situations with landlords, and move quickly when the numbers make sense.
How to Choose Markets for Airbnb Arbitrage: Rob's Strategy
The best market for Airbnb arbitrage is one with year-round demand, not just seasonal spikes. Rob analyzed multiple markets before settling on Louisville and St. Simons Island, focusing on diversification and consistent revenue potential.
Why Louisville Works for Short-Term Rentals
Louisville, Kentucky might not be the first market that comes to mind for Airbnb investing, but Rob discovered it has significant advantages that many overlook.
Year-Round Programming: The city does an exceptional job programming events throughout the year. While people think Louisville is just the Kentucky Derby, Rob found there's much more. Louisville hosts some of the biggest rock concerts in the country, including Louder Than Life, and numerous other events that pull visitors consistently.
Consistent Demand: Unlike seasonal markets where you make all your money in a few months, Louisville provides ebbs and flows throughout the year without dead periods. Rob's Highland House in Louisville is his best-performing property specifically because of this consistency.
Pro Tip from Rob: Look at markets where Danny Wimmer Presents (the concert promoter behind Louder Than Life) hosts events. These cities typically have both the infrastructure and population to support year-round tourism.
"For my thing, I like markets that kind of have something going on throughout the year. You're going to have ebbs and flows, but if you can find something that's relatively consistent, you don't have to worry about - well if I didn't kill it in this month, is my season pretty much over?"
St. Simons Island: Seasonal Diversification
Rob's second market, St. Simons Island, Georgia, represents strategic diversification. The island has clear seasonality - the high season runs from April through September - but Rob chose it deliberately to balance his Louisville properties.
The opportunity came when he found a 4,000 square foot house on Zillow where the owners had accepted a job in Michigan and were moving away for three years. They didn't care what Rob did with it, creating perfect conditions for an arbitrage arrangement.
The Risk Mitigation Strategy: By having properties in both year-round (Louisville) and seasonal (St. Simons) markets, Rob protects himself against local market fluctuations while maximizing revenue potential in different seasons.
Airbnb Arbitrage Strategies That Actually Work: Rob's Playbook
The difference between getting landlords to say yes or no comes down to how you frame the conversation. Rob's sales background gave him a significant advantage in closing deals, but his strategies can be learned and replicated by anyone.
Strategy 1: The Win-Win Landlord Pitch
What it is: Rather than asking landlords to let you use their property as an Airbnb (which sounds like you're taking advantage), Rob frames the entire conversation around what the landlord gains.
Why it works: Most people approach landlords defensively, already expecting rejection. They focus on what they want rather than what the landlord gets. Rob flips this entirely by leading with benefits.
The Core Benefits Rob Presents:
1. Free Property Management: Landlords typically pay a percentage of gross revenue to property management companies. With Rob's model, cleaners visit the property 2-3 times per week, providing constant oversight that landlords would never get with long-term tenants. Standard landlords might do one annual inspection if they're lucky.
2. Better Property Condition: Because Rob is incentivized to maintain five-star reviews, he keeps properties in excellent condition. Any issues get addressed immediately, not left to fester for months like with long-term tenants.
3. Risk Mitigation Systems: For every objection landlords raise ("What if guests throw parties? What if they jump off the roof into the pool?"), Rob has a specific answer. Ring cameras, guest screening questions ("What brings you to the area? How many in your group?"), and professional communication all address concerns before they become problems.
"If you only look at it through the lens of 'why would a landlord let me use their property as an Airbnb' as a negative aspect, you're never going to come out ahead. You have to go into it with - how do I create a win-win for me and the landlord?"
Strategy 2: Remote Property Setup
What it is: Setting up and managing properties in markets you've never visited, using local teams and technology to handle everything.
Why it works: Many people limit themselves to their local market, missing opportunities in better-performing areas. Rob's St. Simons Island property was set up entirely remotely, proving this business can be location-independent.
Rob's Remote Setup Process:
1. Build Your Team Through Referrals: Rob started by vetting cleaners. Once he found good cleaners, he asked them for referrals. If they're already operating in that market and doing well, they know the local handymen, maintenance people, and other service providers.
2. Order Furniture Through Wayfair Pro: With an EIN for your LLC, Wayfair gives you access to a Pro account with a dedicated salesperson. Rob built his cart, called his rep for a discount, and had everything shipped flat-packed to the property.
3. Create Visual Instructions: Rob drew floor plans on notecards, took photos with his phone, and sent them to his handyman showing exactly how each room should look. The handyman assembled everything, arranged it according to Rob's plans, and sent confirmation photos.
4. Use Ring Cameras for Oversight: Cameras let Rob monitor deliveries, confirm work is being done, and verify the property is ready for guests - all without being physically present.
5. Visit After Setup (Optional): Rob and his wife eventually flew to St. Simons in February to do a walkthrough and stay there for a few days. This helped them write the guest book and house manual because it's hard to document how a house operates without experiencing it yourself.
"Once you do it, it's like - I can do this anywhere. It might be a little jarring but you've got FedEx tracking, you know where stuff is. Set up the Ring cameras so you can make sure things are coming in accordingly. It's not hard."
Strategy 3: Automation Through Guesty
What it is: Using Guesty for Hosts as a central management platform to automate messaging, calendar syncing, and operations across all properties and booking platforms.
Why it works: Without automation, managing multiple properties while working a 9-to-5 would be impossible. Guesty handles the repetitive tasks that would otherwise consume hours of Rob's day.
Key Guesty Features Rob Uses:
Channel Management: Guesty pulls all listings into one centralized place. If someone books on Vrbo, it automatically blocks those dates on Airbnb and Booking.com, preventing double bookings without any manual intervention.
Automated Messaging: When someone books, they get an automated message. The day before check-in, another message. The day before checkout, another message. Guests know what to expect, and Rob doesn't have to manually type anything.
Smart Lock Integration: When someone makes a reservation, Guesty generates a unique door code. On check-in day, it activates automatically. Rob is never tied up somewhere unable to let a guest in - the system handles it.
Revenue Tracking: Guesty provides income reports, occupancy statistics, and property-by-property breakdowns. Rob can see he's already at $92,000 revenue by March 2024, tracking ahead of the prior year.
"Could not possibly run this business without it. You don't have time to sit there and send a million messages to guests. The day they check in it turns the code on live so I'm not somewhere tied up where someone's knocking on the door."
Strategy 4: Turnkey Property Hunting
What it is: Specifically seeking properties that are already set up for short-term rentals or require minimal work to go live.
Why it works: Rob's first property was already furnished and permitted as an Airbnb. His downtown Louisville condo was also fully furnished when he found it. By targeting these opportunities, Rob minimizes startup costs and time to revenue.
Indicators of Turnkey Opportunities:
Previous STR operators: Properties that were Airbnbs but are now listed for long-term rent
Fully furnished listings: Owners who don't want to deal with moving furniture
Price reductions: Properties sitting on the market - landlords getting desperate
Owner relocation: People moving away for work who just want reliable tenants
Rob's Downtown Condo Example:
Rob found a condo a block from the Yum Center (Louisville's major arena) that had been sitting on the market. He watched the listing, saw the price tick down, and made his call when they were getting desperate. Listed at $4,000, it had slowly dropped.
The building's condo association wasn't initially favorable to short-term rentals, but after Rob talked to the real estate agent, the board completely changed their mind. He signed a two-year lease, and everything inside - furniture, appliances, decor - was already there. He just added a new TV and some kitchen amenities.
"Was I looking for something like this? Not really. But you got to keep your eyes open because opportunity comes when you least expect it."
Rob's Airbnb Arbitrage Results: The Numbers
Rob generates over $100,000 per year in gross revenue from 3 properties. Here's the complete financial breakdown of his Airbnb arbitrage business.
Complete Financial Breakdown
| Category | Value | Notes |
|---|---|---|
| Year One Gross Revenue | $100,000+ | From 3 properties |
| Q1 2024 Revenue | $92,000 | By March, tracking ahead of prior year |
| Best Performing Property | Highland House | Louisville, year-round events |
| First Property Investment | Minimal | Turnkey - only TVs, Roku sticks, fire pit |
| St. Simons Investment | Significant | Paint, landscaping, full furnishing |
| Downtown Condo Investment | Minimal | New TV, Roku sticks, kitchen items |
Portfolio Performance Summary
Property 1: Highland House (Louisville, KY)
Best performing property in portfolio
Year-round demand from events, concerts, and tourism
Turnkey when acquired (previous owners ran as Airbnb)
Features: backyard with pond, fire pit, outdoor staging for photos
Property 2: St. Simons Island House (Georgia)
4,000 square feet with pool and massive backyard
Seasonal market (April-September peak)
Required full furnishing from scratch via Wayfair
Set up entirely remotely before first visit
Property 3: Downtown Louisville Condo
Block from Yum Center (major arena)
Fully furnished when acquired
Rob uses it for basketball games and concerts
Two-year lease signed after board approved STRs
Key Milestones Achieved
Built a six-figure business from scratch in year one
Scaled from 1 to 3 properties within 12 months
Manages everything while working full-time 9-to-5
Raises two children alongside business operations
Systems so automated he barely thinks about day-to-day management
Properties in multiple states (Kentucky and Georgia)
First property landlords now considering selling to him directly
Airbnb Arbitrage Lessons: What Rob Learned
These five lessons took Rob from MBA student to $100K/year Airbnb entrepreneur. Each one came from real experience and could save you months of trial and error.
"Anybody can do this guys. I'm nothing special. If I can do this, you can do this. All you got to do is just be willing to do it. It's not as hard as you think - it's all in here."
Lesson 1: Just Take the First Step
The Mistake: Analyzing properties endlessly without ever making a single phone call.
What Rob Learned: The biggest barrier to success is analysis paralysis. Rob emphasizes that you'll never feel completely ready, you'll never have perfect information, and you'll definitely bump your head along the way. But that's how you learn.
Why This Matters: Many people in the Legacy Investing Show program analyze hundreds of properties but never pick up the phone. They're waiting for certainty that will never come. Meanwhile, people like Rob who take imperfect action build six-figure businesses.
Lesson 2: Frame Everything as Win-Win
The Mistake: Approaching landlords defensively, expecting rejection, and focusing on what you want.
What Rob Learned: Every objection landlords throw up "really aren't that big of a deal - they just don't have an answer for it." When Rob provides solutions (Ring cameras, guest screening, professional cleaners), landlords realize their concerns are addressable.
The first landlord Rob called literally "chewed him up and spit him out" about potential problems - guests jumping off roofs into pools, parties, damage. Now Rob has answers for every single objection because he learned from that experience.
Why This Matters: Your sales approach determines your success rate. Rob can call five landlords and get at least one or two interested. That conversion rate compounds over time into a portfolio.
Lesson 3: Build Your Team Through Referrals
The Mistake: Trying to find every service provider from scratch through cold outreach.
What Rob Learned: The saying "rockstars know rockstars" proved true. Rob found his St. Simons cleaner, then asked the cleaner for references. From those references, he learned who else was operating successfully in the market and who they used for handymen, maintenance, and other services.
Why This Matters: One good team member can unlock your entire local network. Instead of vetting dozens of providers, you get pre-vetted recommendations from someone already succeeding in that market.
Lesson 4: Invest in Professional Photography
The Mistake: Using iPhone photos or basic real estate listing images for Airbnb listings.
What Rob Learned: Professional Airbnb photography is completely different from real estate photography. Real estate photos show off the house; Airbnb photos show off amenities and help guests imagine themselves in the space - more like hotel photographs.
Rob found his photographer by Googling "Airbnb photographer Louisville Kentucky." She lived two doors down from his Highland House and had experience shooting other properties in the area.
Key Photography Tips from Rob:
Stage the property: champagne glasses in the kitchen, place settings on the table
Show amenities in use: bourbon on the porch (it was actually sweet tea), fire pit lit at night
Return for evening shots: string lights illuminated, outdoor spaces glowing
Create a shot list: know exactly what you need before the photographer arrives
"People are just going by the pictures, and if your pictures suck, they're not clicking it."
Lesson 5: Keep Your Eyes Open for Opportunity
The Mistake: Having rigid criteria that causes you to miss exceptional deals.
What Rob Learned: His downtown Louisville condo wasn't something he was actively looking for. He wasn't planning to scale beyond two properties. But when he saw a fully-furnished condo a block from a major arena, with prices dropping because it wasn't renting, he recognized the opportunity.
Sometimes the best deals aren't the ones you're hunting for - they're the ones that appear while you're paying attention to the market.
Why This Matters: Rob's willingness to act on unexpected opportunities contributed to his rapid scaling. Within one year, he went from zero to three properties, building momentum that compounds over time.
Best Tools for Airbnb Arbitrage: Rob's Tech Stack
Rob manages 3 properties while working a 9-to-5 using these tools. Here's the complete tech stack that powers his $100K/year business.
Essential Tools Overview
| Category | Tool | Purpose | Why Rob Chose It |
|---|---|---|---|
| Property Management | Guesty for Hosts | Central command for all operations | Calendar sync, messaging automation, revenue tracking |
| Smart Locks | Various (Guesty-compatible) | Automated check-in | Codes generate and activate automatically |
| Security | Ring Cameras | Remote monitoring | Verify deliveries, monitor property, guest screening |
| Streaming | Roku Sticks | Guest entertainment | Guest mode lets visitors use their own accounts |
| Furniture | Wayfair Pro | Furnishing new properties | Dedicated rep, bulk discounts, flat-pack shipping |
| Communication | Google Meet | Landlord video calls | Face-to-face builds trust, proves you're legitimate |
Guesty for Hosts: The Core Platform
What it does: Centralizes all listings, automates messaging, syncs calendars, generates door codes, and tracks revenue across properties and platforms.
How Rob uses it: Every booking triggers automatic messages. Every checkout triggers automatic cleaning coordination. Every new guest gets a unique door code that activates on check-in day. Rob barely has to touch anything.
Key features:
Channel management across Airbnb, Vrbo, Booking.com
Automated guest messaging with customizable templates
Smart lock integration with automatic code generation
Revenue and occupancy analytics by property
Unified inbox for all guest communication
Pro tip: Invest time upfront creating message templates. Once set up, you'll rarely touch them again.
Ring Cameras: Remote Eyes
What it does: Provides live and recorded video of property exteriors for security and operational monitoring.
How Rob uses it: Monitors package deliveries during remote property setup, screens guests as they arrive, and addresses any issues without being physically present. For his St. Simons property that he set up remotely, cameras let him verify everything was happening correctly.
Pro tip: Install cameras before anything else when setting up a new property. They provide peace of mind throughout the entire setup process.
Wayfair Pro: Furnishing at Scale
What it does: Provides trade pricing, dedicated sales reps, and organized purchasing for business accounts.
How Rob uses it: When furnishing his St. Simons property from scratch, Rob built his entire cart on Wayfair, called his Pro rep for additional discounts, and had everything shipped flat-packed. His handyman then assembled everything on-site according to Rob's notecard floor plans.
Pro tip: Sign up for a Pro account as soon as you have your LLC's EIN. The discounts and dedicated support are worth it even for one property.
Rob's Advice for Airbnb Arbitrage Beginners
"If I can do this, you can do this. All you got to do is just be willing to do it. It's not as hard as you think - it's all in here."
If Rob were starting over today, here's exactly what he would do:
Step 1: Take Action Immediately
Don't wait until you feel ready. Rob emphasizes that the learning happens through doing, not through watching videos or analyzing properties. Make your first call, experience rejection, refine your pitch, and keep going.
Step 2: Practice Your Landlord Pitch
Even if you don't have your LLC set up, even if you're not ready to sign a lease - make calls. Every conversation sharpens your skills. Rob became one of the best closers in the program because he practiced relentlessly, not because he had natural talent.
Step 3: Look for Turnkey Opportunities
Properties that were previously Airbnbs, fully furnished rentals, and motivated sellers all reduce your startup costs and time to revenue. Rob's best deals came from finding these opportunities rather than starting from scratch.
Step 4: Build Systems Before Scaling
Rob's ability to manage 3 properties while working a 9-to-5 and raising two kids comes entirely from automation. Set up Guesty, create your message templates, connect your smart locks, and establish your team before adding more properties.
Step 5: Diversify Your Markets
Rob strategically chose Louisville (year-round demand) and St. Simons Island (seasonal) to balance risk. Consider similar diversification as you scale - don't put all your properties in one market.
Mindset Advice from Rob
Success in this business is mostly mental. Rob built a six-figure business while managing a full-time job and raising two children. If he can find the time and energy, so can you.
The people who fail are the ones who never start, who analyze forever without acting, who let rejection stop them. The people who succeed are the ones who take imperfect action, learn from mistakes, and keep moving forward.
"Anybody can do this guys. I'm nothing special."
Watch Rob's Full Interview
Video highlights:
0:00 - Rob's background and how he discovered Airbnb arbitrage
5:30 - Finding his first turnkey property in Louisville
12:00 - The win-win landlord pitch that gets yeses
18:45 - Setting up St. Simons remotely without visiting
24:30 - Guesty walkthrough and automation setup
28:00 - Highland House property tour
32:00 - Downtown condo opportunity and advice for beginners
Frequently Asked Questions
How much money can you really make with Airbnb arbitrage while working full-time?
Rob generates over $100,000 per year in gross revenue from 3 Airbnb arbitrage properties while working a full-time 9-to-5 job and raising two kids. By Q1 2024, he had already generated $92,000 in revenue, tracking ahead of the previous year. Results depend on market selection, property quality, and operational efficiency.
Is Airbnb arbitrage still worth it in 2026?
Based on Rob's continued success and growth trajectory, the fundamentals remain strong for operators who execute well. His key factors for success: choosing markets with year-round events (like Louisville), building automation systems that don't require constant attention, and creating win-win relationships with landlords who appreciate the free property management.
What's the biggest challenge with Airbnb arbitrage?
Rob identifies several challenges he navigated:
Landlord Objections: His first call resulted in being "chewed up and spit out" about potential problems. The solution: prepare specific answers for every objection (Ring cameras, guest screening, professional cleaning).
Remote Management: Setting up his St. Simons property without ever visiting required building a trusted team entirely through referrals and using technology for oversight.
Balancing Life: Working full-time while raising two kids means time is precious. Rob solved this with aggressive automation through Guesty - he barely thinks about day-to-day operations anymore.
Start Your Airbnb Arbitrage Journey
Ready to build your own Airbnb arbitrage business like Rob?
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Helpful Resources
About Legacy Investing Show
Legacy Investing Show is Preston Seo's comprehensive Airbnb arbitrage training program. Since founding, the program has:
Trained 2,000+ students across the United States
Generated $10M+ in cumulative student revenue
Built an active community of short-term rental investors
Produced numerous students earning $10K+/month
Preston Seo built a $15 million real estate portfolio and generates $400,000 per year in net profit from his Airbnbs. He created Legacy Investing Show to teach the exact systems that scaled his business, providing the mentorship, scripts, and community that accelerate success.
Learn more about the program | Watch free training
This case study is based on Rob's video interview conducted in March 2024. All statistics and quotes are directly from Rob's experience. Individual results vary based on market, effort, and capital invested.
Last updated: February 1, 2026
Preston Seo
Real estate investor and financial educator helping people build generational wealth through smart investing strategies.
Frequently Asked Questions
Rob generates over $100,000 per year in gross revenue from 3 Airbnb arbitrage properties while working a 9-to-5 job and raising two kids. His Highland House in Louisville is his best performer, generating consistent revenue year-round thanks to Louisville's event programming.
Yes. Rob started in 2020, secured his first property in October, went live in January 2021, and scaled to 3 properties generating $100K+/year by 2024. His success depends on market selection (year-round events), landlord relationships, and automation through tools like Guesty for Hosts.
Rob uses a win-win sales approach: 1) Free property management - cleaners visit 2-3 times per week, better than annual inspections; 2) Year-round occupancy with constant oversight; 3) Ring cameras and guest screening to prevent parties; 4) Professional maintenance coordination. He addresses every objection by showing how he mitigates risks.
Yes. Rob manages his St. Simons Island property in Georgia from Louisville, Kentucky without being there. He built his team through cleaner referrals, had his handyman assemble furniture from Wayfair, drew floor plans on notecards, and set up Ring cameras. He only visited after everything was operational.
Rob found his first property already set up as an Airbnb - the owners had launched in February 2020 but pivoted to long-term rentals when travel stopped. The property was fully furnished and had permits in place. He looked for properties on Zillow where owners already understood the STR model.
Guesty for Hosts is an Airbnb management platform that centralizes all listings, syncs calendars across Airbnb/Vrbo/Booking.com to prevent double bookings, automates guest messaging, generates door codes for smart locks, and tracks revenue/occupancy. Rob says he "could not possibly run this business without it."
Rob joined Legacy Investing Show in August, had his first property under lease contract by October, and went live in January - about 5 months from program start to first booking. By year one, he was on track for over $100K in revenue across 3 properties.
Based on Rob's results, the ROI speaks for itself: from zero properties to $100K+/year in revenue within one year. He credits the course for providing the roadmap, landlord scripts, and confidence to take action. His advice: "If I can do this, you can do this - it's all in your head."
Rob chose Louisville, Kentucky because the city programs events year-round - not just the Kentucky Derby. They host major rock concerts like Louder Than Life and other events that create consistent demand. He diversified with St. Simons Island, Georgia (April-September seasonality) to balance risk.
Rob's first property required minimal investment because it was already furnished as an Airbnb. For his St. Simons property, he invested in paint, landscaping, furniture from Wayfair (with Pro account discounts), and assembly labor. He negotiated with landlords to reduce security deposits and invest the difference in property improvements.