How Rob Made $100K from 3 Airbnbs While Working a 9-to-5 and Raising Two Kids

Rob generated over $100,000 in revenue from 3 Airbnb properties in his first year—all while working a 9-to-5, finishing his MBA, and raising two kids. His secret? Finding turnkey properties that required minimal setup, building reliable remote teams through cleaner referrals, and using Guesty automation to manage everything in minimal time.

This case study breaks down exactly how Rob built a six-figure Airbnb arbitrage business across two markets (Louisville, KY and St. Simons Island, GA), including his win-win landlord pitch, the importance of Airbnb-specific photography, and why he's already at $92,000 YTD by March of year two.

In this article:

• Quick Results Summary
• The Starting Point
• Market Selection Strategy
• The Win-Win Landlord Pitch
• Finding Turnkey Properties
• Remote Team Building
• Listing Optimization
• Financial Results
• Key Lessons for Beginners
• Tools & Systems Used
• FAQs

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Quick Results: Rob's Airbnb Arbitrage Numbers

Metric	Value	Context
Year 1 Revenue	$100,000+	Gross from 3 properties
2024 YTD (March)	$92,000	Already tracking ahead
Properties	3	Louisville + St. Simons
Property 1 Setup	Minimal	Turnkey, previously Airbnb
Property 3 Setup	Minimal	Furnished downtown condo
Family	Wife + 2 kids	Built around family life
Background	MBA + Sales	No prior STR experience

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Rob's Background: MBA, Sales Experience, and No Time to Waste

You don't need to quit your job or sacrifice family time to build a substantial Airbnb business. Rob proved that strategic property selection and ruthless automation can produce six-figure results while maintaining career and family commitments.

Rob came to Airbnb arbitrage mid-2020, while finishing his MBA and looking to deploy savings into a new venture. He'd already started one business alongside his 9-to-5 and was searching for a relatively low-risk entry point into real estate.

Preston's Instagram videos caught his attention. The "bridge method"—using rental arbitrage to build cash flow before potentially acquiring properties—made sense as a low-capital starting point.

"After doing the research I decided to join the course... I joined in August and then by October I had my first property lease under contract, and then that went live in January."

The timeline from decision to live property was roughly 5 months. From there, Rob added two more properties within the same year, scaling to over $100,000 in revenue while maintaining his full-time job and raising two children.

His sales background proved invaluable for landlord conversations, but Rob emphasizes that the real skill isn't sales—it's reframing. Instead of "selling" arbitrage to landlords, he presents genuine win-win scenarios.

Key Takeaway: Rob didn't wait for the "perfect time" (MBA done, kids grown, more savings). He started during one of the busiest periods of his life and built systems that worked around his constraints.

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Market Selection: Year-Round Events vs. Seasonal Tourism

The best Airbnb market depends on your goals and risk tolerance. Rob operates in two distinct markets, each with different demand patterns.

Louisville, Kentucky: Year-Round Consistency

Louisville wasn't Rob's first choice—he initially researched Florida markets where family lived. He got yeses from landlords and agreements ready to sign. Then he pivoted to his home base.

Why Louisville works:

Year-round programming: Unlike markets that depend on one season, Louisville has events throughout the year:

• The Kentucky Derby (major, but not the only driver)
• Louder Than Life and other massive rock concerts
• Multiple festivals and conventions
• University sports events
• Business travel to corporate headquarters

"People think Louisville is just the Derby. We have some of the biggest rock concerts in the country... there are a handful of other events that happen really throughout the year."

Consistent occupancy: Rob doesn't have to make his entire year's revenue in 3 months. He can book steadily across all seasons, reducing stress and cash flow uncertainty.

Home base advantage: Being local means Rob can visit properties, meet teams, and respond to emergencies if needed. His first two Louisville properties benefit from this proximity.

St. Simons Island, Georgia: Seasonal Beach Market

Rob's second property is in St. Simons Island, a Georgia barrier island with distinct seasonality:

• Peak season: April through September
• Off-season: October through March

This creates a different business model—maximize revenue during peak months to cover the slower winter period.

Why Rob added a seasonal market:

• Diversification (Louisville slow months ≠ St. Simons slow months)
• Higher peak-season rates can offset lower volume
• Beach properties command premium pricing
• Willing sellers exist (the landlords were moving to Michigan for 3 years)

The Two-Market Strategy

Rob's portfolio balances consistency and upside:

• Louisville provides reliable, year-round cash flow
• St. Simons provides seasonal spikes and premium rates

This diversification means a slow month in one market doesn't tank his entire portfolio.

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The Win-Win Landlord Pitch: Reframing Arbitrage

The question isn't "how do I convince landlords"—it's "how do I create genuine value for them." Rob's sales background helped him develop a pitch that addresses landlord concerns before they're raised.

The Wrong Approach

Many beginners think: How do I get access to their property for my business?

This mindset creates defensive, extractive conversations. Landlords sense you want something from them and resist.

Rob's Approach: Lead with Value

Rob enters every conversation thinking: How is this a win-win?

Value proposition for landlords:

1. Guaranteed occupancy: "Someone is staying in your property 365 days a year, keeping an eye on things."

2. Free property management: "I'm essentially providing property management at no cost to you—typically landlords pay a percentage of gross to a management company."

3. Regular maintenance checks: "I have someone in there after every guest turn to clean and verify everything works. That's weekly (sometimes more) inspections that you'd never get from a long-term tenant."

4. No tenant turnover hassle: "You know the expense and uncertainty of turning over a unit between long-term tenants. With me, you avoid that entirely."

5. Invested tenant: "I'm paying you rent AND making money from this property. My incentives are perfectly aligned with keeping it in excellent condition."

"In effect the landlord is getting free property management... they get their rent, they get their place taken care of, it's an absolute win-win."

Handling Objections

Rob has encountered every objection—parties, property damage, noise complaints, insurance concerns. His approach: every objection has a mitigation strategy.

"What if guests throw parties?"

• Ring cameras on exterior entrances
• Guest screening questions (What brings you to the area? How many in your group?)
• Noise monitoring devices
• Clear house rules with financial penalties

"What if something breaks?"

• Immediate response through local team
• Documentation of condition before/after each guest
• Reserve fund for repairs
• Communication protocols with landlord

"I've never done this before / it seems risky"

• Walk through the process step by step
• Offer references from other landlords (after you have them)
• Start with shorter lease terms if needed
• Propose a trial period

The First Rejection

Rob's first landlord call was brutal. A Fort Lauderdale property owner "chewed him up and spat him out," imagining worst-case scenarios: people jumping off roofs into pools, wild parties, property destruction.

But Rob learned from it. Every objection that landlord raised became a talking point for future calls—because now Rob had answers ready.

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Finding Turnkey Properties: Minimal Setup, Maximum Speed

Not every property requires $15,000 in furniture and weeks of setup. Rob found deals that were ready to list almost immediately.

The Highland House: Previous Airbnb

Rob's first property was essentially handed to him ready-made:

What the owners had done:

• Operated it as an Airbnb (went live February 2020—terrible timing)
• Fully furnished to short-term rental standards
• Already had permits in place
• Pivoted to long-term rentals when COVID hit travel

What Rob inherited:

• Complete furniture package
• Kitchen fully equipped
• Decor and staging in place
• Operational knowledge of what works

What Rob added:

• A few TVs and Roku sticks
• Fire pit for backyard ambiance
• Outdoor string lights for evening photos
• Cornhole and activities
• Bed configuration optimization (swapped twin/trundle for queen)

Total additional investment: Minimal—probably under $2,000.

"The first one was kind of like a very easy, no barrier to entry type of deal... they had fully furnished the place and set it up to operationally run as an Airbnb."

The Downtown Condo: Another Turnkey Win

Rob's third property followed a similar pattern:

The situation:

• Downtown Louisville condo, one block from the Yum Center (major arena)
• Owners weren't using it and didn't plan to return soon
• Fully furnished and updated
• Sat on market with price declining (from $4,000/month down)

The opportunity:

• COA (condo owner association) initially opposed short-term rentals
• Rob reached out anyway, explaining the business model
• The condo owner happened to be on the COA board
• After Rob's pitch, they reversed their position

What Rob needed to add:

• New TV
• Roku sticks
• Kitchen amenities for guests

Again, minimal investment for a property that's now consistently booked—especially during events at the arena literally one block away.

"Sometimes you just got to do it... I wasn't necessarily looking to scale beyond two, and then I saw this and I was like, well, why not?"

The St. Simons Property: Full Furnishing Required

Not every deal is turnkey. Rob's St. Simons property required complete furnishing of a 4,000 square foot house with a pool—a significant undertaking.

But even here, Rob minimized friction:

• Ordered everything through Wayfair (Pro account for discounts)
• Shipped flat-packed furniture directly to the property
• Had his handyman assemble and place everything
• Drew floor plans on notecards and sent photos
• Verified setup through pictures before going live

The lesson: turnkey properties exist and dramatically accelerate your timeline. But when you have to furnish from scratch, systems and teams make it manageable even remotely.

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Remote Team Building: Cleaners Know Rockstars

Your first great hire unlocks an entire network. Rob's approach to building remote teams starts with one person: the cleaner.

Why Cleaners First

Cleaners are your most critical team member:

• They're in your property after every guest
• They see everything (damage, wear, problems)
• They determine guest experience through cleanliness
• They often know the local service provider network

If you have one reliable cleaner, you have a foundation to build on.

The Referral Method

Once Rob found a great cleaner, he asked a simple question: "Who else do you recommend?"

What good cleaners can refer:

• Handymen they've seen work on other properties
• Contractors for larger repairs
• Other cleaners (for backup or additional properties)
• Photographers who specialize in Airbnb listings
• Local suppliers for restocking

"Rockstars know rockstars... from those referrals I got, that's how I built my team."

The referral carries weight because the referrer's reputation is on the line. A cleaner who values their relationship with you won't recommend unreliable people.

Communication is King

For remote properties especially, communication makes or breaks your team relationships. Rob's expectations:

For cleaners:

• Update after every turnover
• Flag any issues immediately
• Send photos of completed cleans
• Respond to messages within reasonable time

For handymen:

• Provide repair timelines before starting
• Document work with before/after photos
• Communicate honestly about scope and cost
• Be available for emergencies (with appropriate compensation)

Rob trusts his team because he established these expectations upfront and selected people who meet them.

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Listing Optimization: Photos Are Make or Break

Guests decide on photos before reading a single word. Rob invested in professional photography that sells the experience, not just the space.

The Photography Difference

Rob distinguishes between real estate photography and Airbnb photography:

Real estate photography shows:

• Room dimensions
• Property features
• Square footage impression

Airbnb photography shows:

• What guests will EXPERIENCE
• Amenities in action
• Lifestyle moments

"A real estate listing is going to be one thing... what an Airbnb photographer—a good Airbnb photographer—is going to do is they're going to show off the amenities so that as a guest or traveler you can imagine yourself in this space."

Staging for Photos

Rob doesn't just photograph his properties—he stages specific shots:

The backyard evening shot:

• Fire pit lit
• String lights glowing
• Bourbon glasses staged (actually sweet tea—pro tip)
• Cornhole boards visible

The kitchen shot:

• Champagne flutes staged
• Coffee maker prominently displayed
• Table set with place settings showing capacity

The bedroom shot:

• Pillows fluffed and arranged
• Lighting warm and inviting
• Skyline watercolor print visible (Etsy purchase)

Night Photography

Rob brought his photographer back at night specifically to capture:

• The fire pit ambiance
• String lights on the porch
• The property "in action" during evening hours

This extra effort pays off. Guests searching for "weekend getaway" or "romantic retreat" are drawn to listings that show nighttime atmosphere.

Finding the Right Photographer

Rob's method: Google "Airbnb photographer [city]." His photographer literally lived two doors down from one of his properties—convenience plus local expertise.

For remote properties, Rob uses the same referral method as team building. Cleaners often know photographers, or other Airbnb operators can recommend their favorites.

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Financial Results: Six Figures and Growing

Year one exceeded $100,000 in gross revenue. Here's the complete financial picture.

Year 1 (2023) Results

Metric	Value
Gross Revenue	$100,000+
Properties	3
Best Performer	Highland House (Louisville)
Markets	Louisville, KY + St. Simons Island, GA

The Highland House—Rob's turnkey first property—was the strongest performer. Louisville's year-round events kept it consistently booked.

Year 2 (2024) Tracking

By March 2024, Rob's portfolio was already showing acceleration:

Metric	Value
YTD Revenue (March)	$92,000
Projected Full Year	$140,000+
Growth Rate	40%+ over Year 1

The improvement comes from:

• Full year of St. Simons bookings (first year had setup time)
• Optimized pricing through experience
• Review accumulation improving booking velocity
• Downtown condo fully operational

The Investment Perspective

Rob views year one differently than most: it was an investment year.

St. Simons required substantial upfront capital for furnishing, pool maintenance setup, and landscaping. Rather than extract profits, Rob reinvested everything to scale.

"Coming from the Highland House where everything was pretty much done for me... the St. Simons one was a totally different story. We had to furnish it from top to bottom."

His philosophy: year one is for building infrastructure. Years two and beyond are for reaping returns.

Why Arbitrage vs. Buying

Rob articulates the arbitrage advantage clearly:

Capital requirements:

• Arbitrage: Security deposit + furnishing ($5K-$20K per property)
• Buying: Down payment + closing costs + furnishing ($50K-$100K+ per property)

Risk profile:

• Arbitrage: If it fails, you lose a security deposit and can exit the lease
• Buying: Forced to sell a property in potentially unfavorable market conditions

Scale speed:

• Arbitrage: Can add properties as fast as you find deals
• Buying: Limited by capital accumulation and financing

Tradeoffs acknowledged:

• Arbitrage doesn't build equity
• Arbitrage doesn't have tax depreciation benefits
• Arbitrage requires ongoing landlord relationships

For Rob, arbitrage was the right entry point. Future plans may include acquiring properties for ownership benefits.

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Key Lessons: What Rob Learned Building to Six Figures

Lesson 1: Create Your Own Luck Through Action

The Myth: Rob got lucky with turnkey properties and easy landlords.

The Reality: Rob created opportunities through consistent action. He researched multiple markets, called numerous landlords, and stayed alert for deals that others would miss.

The downtown condo that "fell into his lap"? He'd been watching it on Zillow for weeks, tracking the price drops, waiting for the right moment to reach out. When the COA initially said no to short-term rentals, he didn't give up—and they reversed their position.

"You're not going to get lucky by just sitting there and running a bunch of numbers. You're going to get lucky by actually putting yourself out there and putting in the action."

Your Action Steps:

1. Save properties on Zillow and watch price changes
2. Reach out even when circumstances seem unfavorable
3. Follow up when initial answers are "maybe" or "not yet"
4. Stay ready to move quickly when opportunities emerge

Lesson 2: Frame Every Conversation as Win-Win

The Mistake: Approaching landlords as if you need something from them.

What Rob Does: Leads with value. Free property management. Regular maintenance checks. Guaranteed rent. Aligned incentives.

Every objection has a mitigation. Every concern has a response. The conversation isn't adversarial—it's collaborative problem-solving.

"You have to go into it with how do I create a win-win for me and the landlord."

Your Action Steps:

1. List every benefit arbitrage provides to landlords
2. Prepare specific answers for common objections (parties, damage, noise)
3. Practice reframing from "I want" to "here's what you get"
4. Think of yourself as solving the landlord's problems

Lesson 3: Turnkey Properties Exist—Find Them

The Assumption: Every property needs $15,000 and weeks of setup.

The Reality: Previous Airbnbs exist. Furnished units sit on markets. Landlords have furniture they don't want to move.

Rob's first and third properties required minimal investment because he identified situations where furnishing was already complete.

How to find turnkey deals:

• Search for listings that mention "furnished" or "turnkey"
• Look for properties that seem over-improved for long-term rentals
• Ask landlords if they have furniture included or available
• Watch for price drops indicating motivated sellers/landlords

Your Action Steps:

1. Add "furnished" to your search filters
2. Ask every landlord: "Is there any furniture included?"
3. Research property history—was it previously an Airbnb?
4. Consider slightly higher rent for fully furnished units

Lesson 4: Your Cleaner is Your Most Important Hire

The Mistake: Treating cleaners as interchangeable commodities.

What Rob Does: Finds one exceptional cleaner, builds a relationship, then uses them as his gateway to the entire local network.

Good cleaners know good handymen. They know good contractors. They know other cleaners. One relationship unlocks an entire team.

"From the referrals I got, that's how I built my team."

Your Action Steps:

1. Spend extra time vetting cleaners thoroughly
2. Test communication responsiveness before hiring
3. Ask every good hire: "Who else do you recommend?"
4. Pay fairly—good people are worth premium rates

Lesson 5: Think Like a Guest When Staging Photos

The Mistake: Photographing empty rooms and basic spaces.

What Rob Does: Stages his properties to show experiences, not just rooms. Fire pits lit at night. Tables set for dinner. Activities visible. Atmosphere captured.

Guests don't book square footage—they book experiences. Photos should answer: "What will it feel like to stay here?"

Your Action Steps:

1. Stage every room before photography
2. Capture night shots with lights on
3. Show amenities in use (fire pit lit, pool ready)
4. Highlight what makes your property different

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Tools & Systems: Rob's Operations Stack

Automation makes six figures manageable alongside a 9-to-5 and family. Here's Rob's complete toolkit.

Guesty: The Central Command

Rob cannot overstate Guesty's importance to his operation:

What Guesty handles:

• Calendar synchronization across Airbnb, Vrbo, Booking.com
• Automated guest messaging (booking confirmation, check-in instructions, checkout reminders)
• Smart lock integration (codes generated and activated automatically)
• Revenue tracking and financial reporting
• Cleaner scheduling notifications

Why it matters:

"I cannot possibly run this business without it."

Before automation, every guest would require manual messages. With three properties and constant turnovers, that's hours of repetitive work per week. Guesty reduces it to near-zero.

Price Labs: Dynamic Pricing

Price Labs automatically adjusts rates based on:

• Local events and demand spikes
• Seasonal patterns
• Day-of-week variations
• Competitor pricing
• Booking velocity

Rob sets the parameters and lets the algorithm work. He reviews periodically but doesn't manually adjust prices for individual dates.

Smart Locks: Seamless Access

Integrated with Guesty, smart locks:

• Generate unique codes per reservation
• Activate codes only during guest stay
• Eliminate key handoffs and meetups
• Provide access logs for security

Rob never meets guests in person for check-in. The code is sent automatically, works during their stay, and deactivates at checkout.

The Full Stack

Category	Tool	Purpose
Property Management	Guesty	Central hub for all operations
Dynamic Pricing	Price Labs	Automated rate optimization
Smart Locks	Various (integrated)	Keyless guest access
Photography	Local Airbnb photographers	Listing-quality images
Team Coordination	Text/Call	Direct communication with cleaners and handymen

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Watch Rob's Full Interview

Video highlights:

• 0:00 - Introduction and background
• 5:30 - Market selection (Louisville vs. Florida)
• 10:45 - The win-win landlord pitch
• 17:20 - Finding turnkey properties
• 22:00 - Listing walkthrough and photography tips
• 27:30 - Financial results and future plans
• 31:00 - Advice for beginners

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Frequently Asked Questions

Is $100K in Airbnb revenue realistic for a side business?

Rob proves it is. His three properties generated over $100,000 in year one, and he's tracking to exceed that in year two (at $92,000 by March). The keys are:

1. Market selection: Choose markets with consistent demand (events, tourism, business travel)
2. Property selection: Turnkey properties reduce startup costs and time
3. Automation: Tools like Guesty eliminate repetitive manual work
4. Reliable teams: Cleaners and handymen handle physical operations

The business doesn't require 40 hours per week. With systems in place, Rob manages everything alongside his full-time job and family.

How do you balance Airbnb, a job, and family?

Rob's approach:

Automation handles repetition: Guest messages, pricing, and access codes are automatic. Rob isn't glued to his phone responding to inquiries.

Teams handle physical work: Cleaners turn over properties. Handymen fix issues. Rob coordinates via text, rarely needing to visit properties.

Strategic property selection: Turnkey properties and year-round markets reduce stress. Rob isn't scrambling to make his entire year's revenue in 3 months.

Clear boundaries: Airbnb tasks have their time. Family time is family time. The business fits around life, not the other way around.

What if the COA or landlord initially says no to short-term rentals?

Rob's downtown condo deal started with a "no" from the COA. Here's what happened:

1. The property sat on market with no takers
2. Rob reached out anyway, explained his business model
3. The owner (who was on the COA board) listened
4. The COA reversed their position
5. Rob signed a two-year lease

The lesson: "No" often means "not yet" or "convince me." Circumstances change. New information changes minds. Persistence—respectful, value-focused persistence—can flip initial rejections.

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Start Your Airbnb Arbitrage Journey

Ready to build a six-figure Airbnb business while keeping your day job?

Rob proved that strategic property selection, reliable automation, and consistent action can produce $100K+ results—even while working full-time and raising two kids.

Learn more about Legacy Investing Show →

Related Success Stories

• How Gary Built a $35K/Month Airbnb Portfolio
• How James Made $7K/Month from 3 Properties in 57 Days
• How Micah Found His First Property with One Facebook Message

Helpful Resources

• Complete Guide to Airbnb Arbitrage
• Win-Win Landlord Scripts
• Guesty Setup Guide for Beginners

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About Legacy Investing Show

Legacy Investing Show is Preston Seo's comprehensive Airbnb arbitrage training program. Since its founding, the program has:

• Trained 2,000+ students across the United States
• Generated $10M+ in cumulative student revenue
• Helped students achieve six-figure portfolios while maintaining careers
• Built a community where strategies and wins are shared freely

Preston Seo has personally built a $15 million real estate portfolio generating over $400,000 per year in net profit from short-term rentals. He created Legacy Investing Show to teach the exact systems that scaled his business.

Learn more about the program → | Watch free training →

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This case study is based on Rob's video interview conducted in February 2024. All statistics and quotes are directly from Rob's experience. Individual results vary based on market, effort, and capital invested.

Last updated: January 23, 2026