How Brian Makes $2,000/Month with Airbnb Arbitrage While Working Full-Time in IT (2026)
Preston Seo
Brian O'Leary earns $1,500 to $2,000 per month in cash flow from one Airbnb property in Iowa while working full-time in IT. Starting with zero short-term rental experience, he joined Legacy Investing Show in early January, secured a historic 4-bedroom home by month's end, and went live on Airbnb in February. Today, Brian manages his property with just 1-2 hours per week thanks to automation, while planning to scale to four properties by year-end.
This case study breaks down exactly how Brian built this Airbnb arbitrage business, including his landlord negotiation strategy, property selection process, and the automation systems that make it possible to host while working full-time.
In this article:
Quick Results: Brian's Airbnb Arbitrage Numbers
| Metric | Value | Context |
|---|---|---|
| Monthly Cash Flow | $1,500-$2,000 | After all expenses |
| Properties | 1 | Iowa market |
| Bedrooms | 4 | Historic home |
| Guest Capacity | 10 | 3 queens + bunk beds |
| Time to First Property | 30 days | From joining program |
| Time to Cash Flow Positive | 2 months | February launch, March positive |
| Weekly Time Investment | 1-2 hours | With automation |
| 2026 Goal | 4 properties | One per quarter |
Brian's Background: From IT Professional to Airbnb Entrepreneur
You don't need to leave your full-time job to build a successful Airbnb business. Brian O'Leary proves that the arbitrage model works perfectly as a side business for professionals seeking additional income streams.
Long-Term Rental Experience
Brian works in information technology in Iowa and enjoys his job. But like many professionals, he was looking for additional sources of income beyond his salary. He had previous experience with a long-term rental property that he still owns today, but that property wasn't situated in a good location for short-term rentals.
His long-term rental experience was positive overall, but he noticed a pattern: the longer a tenant stayed, the more work required when they eventually left. His longest tenant stayed for three years, and the turnover when they departed required significant effort to get the property rent-ready again. The accumulating wear and tear over extended tenancies created larger maintenance projects between tenants.
Why Short-Term Rentals Made Sense
Rather than purchasing additional properties to expand his real estate portfolio, Brian decided to explore the arbitrage model. The appeal was clear: higher cash flow potential without the large capital requirements of purchasing properties, the ability to test markets before committing to ownership, and generating income that could eventually fund property purchases.
Brian saw Airbnb arbitrage as a stepping stone. He wanted to use the arbitrage model to bring in more cash, then eventually purchase properties that make sense for short-term rental use. The strategy allows him to build capital and experience simultaneously.
"I wanted to expand and instead of expanding into purchasing more properties, I decided to check out this arbitrage model. I'm using it to bring in more cash, and then properties that make sense, I'll see if there's an opportunity to switch from renting to owning."
Key Insight: Brian's IT background gave him an advantage with the organizational and automation aspects of the business. He approached the setup systematically, following checklists and implementing automated systems from day one.
The Airbnb Arbitrage Journey: Brian's Timeline
January 2026: Joining Legacy Investing Show
Situation: Brian joined the program in early January with a clear goal and no short-term rental experience.
Brian came into the program looking for a structured approach to starting an Airbnb business. He had researched the model and understood the basics, but wanted the confidence that comes from a proven roadmap and community support. He set an ambitious goal: one property per quarter, meaning four properties by year-end.
The Property Search Process
Situation: Brian searched Zillow in his target market and found 4-5 properties of interest.
Brian's search strategy was methodical. He focused on his local Iowa market, searching Zillow for properties that met his criteria. Of the 4-5 properties he identified as potential fits, he was able to get three landlords interested enough to continue the conversation.
Importantly, none of the landlords said "no" outright. Brian got them to a point where they were open to discussing the business model and scheduling property viewings. This intermediate step was crucial: getting landlords from "maybe" to "let's talk more" before pushing for a commitment.
Convincing Multiple Landlords
Situation: Brian used Legacy Investing Show scripts and community credibility to close his preferred landlord.
Brian's approach to landlord conversations was strategic. He used the scripts provided in the roadmap but tailored them to his personality and conversational style. As he puts it, you need to have a natural conversation rather than sounding like you're reading from a script.
The biggest hurdle was proving he could deliver on his promises as someone new to the business. His solution was leveraging the community. He told landlords that while he was new to short-term rentals, he was part of a team that had done this for dozens of homes. He provided links to other community members' listings showing the quality of photos and five-star reviews they achieved.
"That's where just having a group of people behind me was really helpful. I was able to tell her, 'Yes, while I am new to this, I am part of a team that has done this for dozens of homes and they are Superhosts. Here's a link to a few of those you can check them out. The level of quality photos and reviews you're seeing on these listings - that's what I'm going to bring to your property.'"
After visiting all three properties, one stood out dramatically. Brian and his wife didn't want to leave the property - they wanted to buy it and stay there themselves. That emotional response became his selection criteria: if he was excited about the property, it would be an easy sell on Airbnb.
February 2026: Going Live
Situation: Property closed in January, went live on Airbnb in February.
Brian moved quickly after selecting his property. He closed on the lease in January, spent the remaining time staging and photographing the space, and went live on Airbnb in February. The winter timing meant photos were taken with snow on the ground, but Brian planned to update outdoor photos in late April or early May to showcase the property's beautiful front porch and views.
February didn't generate many bookings - expected for a new listing in winter. But by March, the property was cash flow positive in the $1,500-$2,000 range. The trajectory was clear: as they approached summer (the busiest season in his market), bookings would continue to increase.
How to Choose a Market: Brian's Iowa Strategy
Iowa works for Airbnb arbitrage because of its historic properties, tourism appeal, and landlord-friendly environment. Brian chose to start in his home market for hands-on experience before expanding to more competitive areas.
Why Iowa Works for Short-Term Rentals
Brian's target market is a part of Iowa along the Mississippi River with significant historical appeal. The area attracts visitors looking for unique experiences in historic properties, and the views are remarkable - Brian's property offers views of three states from the front porch.
Demand Drivers in Brian's Market:
Historic tourism along the Mississippi River
Weekend getaways for families
Scenic views and outdoor activities
Less competition than major metro areas
The Strategic Advantage:
Brian's approach was to start local for his first property. He wanted to be hands-on with staging, setup, and the complete guest experience before attempting remote management. Once he had reliable boots-on-the-ground (cleaners, handyman), he could leverage that infrastructure for additional properties in the same market.
"We started in this market because I wanted to start somewhat close to home. I really wanted to be there, to stage it, to see what things were looking like from beginning to end. I'm probably going to set up more properties in this market just to take advantage of everything we have in place - cleaners, handyman, all that footwork that's already been done."
Future Expansion Plans:
After establishing his local market presence, Brian plans to expand into more profitable cities using remote setup strategies. His goal is to leverage the local team he's built while also applying what he's learned to manage properties hundreds of miles away.
Brian's Property Selection Criteria
Brian's property selection was specific to his market's appeal:
The Excitement Test:
Brian's most important criteria: Would he and his wife want to stay there? When they visited the property and didn't want to leave, he knew guests would feel the same way. That emotional response became his decision-maker.
Airbnb Arbitrage Strategies That Work: Brian's Playbook
The difference between struggling and succeeding with Airbnb arbitrage often comes down to following a proven system. Brian attributes his success to four core strategies that new hosts frequently overlook.
Strategy 1: Following the Roadmap Exactly
What it is: Brian followed the Legacy Investing Show roadmap step-by-step without trying to reinvent the wheel or skip ahead.
Why it works: Many new entrepreneurs try to customize or shortcut proven processes, often causing problems they could have avoided. Brian took the opposite approach: he trusted the roadmap and followed it precisely, from LLC setup to bank account creation to landlord scripts.
The roadmap provided checklists for everything: getting the business bank account open, setting up the LLC, creating a website, and all the small tasks that are easy to forget. Brian marched through the list systematically, completing everything in a short period of time.
"He didn't overcomplicate anything. He just followed the roadmap to a T and now he has a property cash flowing him two thousand dollars a month."
Brian's Results with This Strategy:
Property secured within 30 days of joining
Live on Airbnb within 60 days
Cash flow positive within 90 days
No major mistakes or setbacks
Strategy 2: Community Credibility for Landlord Pitches
What it is: Using successful community members' listings as proof of what you can deliver, even when you're brand new.
Why it works: The biggest fear for landlords is that a new operator won't deliver on promises. By showing existing Superhost listings from community members, Brian demonstrated the quality standard he was joining - not just making empty promises.
How Brian Positioned This:
Acknowledged being new to the business model
Emphasized being part of a team with proven results
Provided links to community members' listings
Highlighted Superhost status and five-star reviews
Set expectations that he would deliver the same quality
This approach transforms the conversation from "trust me, a stranger" to "trust us, a community with documented results."
Brian's Results with This Strategy:
Got 3 out of 4-5 landlords to continue conversations
Closed his preferred property despite being brand new
Built landlord confidence that led to a signed lease
Strategy 3: Property That Excites You
What it is: Selecting properties based on your own excitement level, not just the numbers.
Why it works: If you're excited about a property, guests will be too. Brian turned down two viable properties to choose the one that made him and his wife not want to leave. That emotional response translates directly to compelling listing photos, enthusiastic descriptions, and five-star guest experiences.
Brian's Decision Process:
Visited all three properties that landlords agreed to show
Evaluated each objectively but also emotionally
One property created an immediate "wow" response
Turned down two good options for the exceptional one
"When I was able to get them to the point where we could look at these properties in person, out of the three, one just got me really excited. I didn't want to leave the property. My wife and I wanted to buy the property and stay there. I thought, okay, that's the type of place I want to put on the market as a short-term rental, because if I'm excited about it, it's going to be an easy sell on Airbnb."
Strategy 4: Listen to Guest Feedback
What it is: Actively responding to guest requests by adding amenities and features they ask for.
Why it works: Guests tell you exactly what would improve their experience. By listening and responding, you continuously improve your listing and can say "yes" to future guests with the same needs.
Improvements Brian Made Based on Feedback:
Dedicated office space: Added for remote workers (photo update pending)
Crib and child gates: Purchased immediately when a guest asked
Kid-friendly amenities: Built out family features for the 4-bedroom house
Brian's philosophy: when a guest requests something reasonable, say "yes" and buy it. Then you can immediately say "yes" to future guests with the same question, and your listing becomes more competitive.
"We've had guests that asked if there was a crib or a child gate and we just said yes, went out and bought it. This is a four bedroom house catered to families, so it's going to be good to have those things and be able to say yes to future guests."
Brian's Airbnb Arbitrage Results: The Numbers
Brian generates $1,500-$2,000/month in net profit from one property. Here's the complete breakdown of his Airbnb arbitrage business.
Financial Breakdown
| Metric | Before Airbnb | After (March 2026) |
|---|---|---|
| Monthly Side Income | Long-term rental only | +$1,500-$2,000 Airbnb cash flow |
| Properties Managed | 1 long-term rental | 1 LTR + 1 short-term rental |
| Weekly Time Investment | Varies | 1-2 hours |
| Guest Capacity | N/A | 10 guests per property |
| Income Consistency | Fixed monthly rent | Variable (higher ceiling) |
Short-Term vs. Long-Term Rental Comparison:
| Factor | Long-Term Rental | Short-Term Rental |
|---|---|---|
| Cash Flow | Moderate, consistent | Higher potential, variable |
| Payment Timing | Monthly, sometimes late | Upfront before arrival |
| Turnover Work | Heavy between tenants (1-3 years) | Light after each stay (professional cleaning) |
| Property Condition | Issues accumulate over time | Maintained after every guest |
| Time Investment | Low during tenancy, high at turnover | Consistent 1-2 hours weekly with automation |
Key Milestones Achieved
Joined Legacy Investing Show in early January
Identified 4-5 potential properties on Zillow
Got 3 landlords to agree to property viewings
Closed on preferred property by end of January
Completed staging and professional photography in February
Went live on Airbnb in February
Achieved cash flow positive status in March ($1,500-$2,000)
Narrowly missed Superhost status (needed 10 guests by April 1)
Added dedicated office space for remote workers
Added family amenities (crib, child gates) based on guest feedback
Scheduled outdoor photo reshoot for late April/early May
What's Next for Brian:
Achieve Superhost status in next review period
Update outdoor photos to showcase front porch and river views
Add second property in Q2 (cash flow permitting)
Reach four properties by end of 2026
Eventually expand to more profitable markets remotely
Airbnb Arbitrage Lessons: What Brian Learned
These five lessons took Brian from IT professional with zero short-term rental experience to $2,000/month cash flow. Each one came from real experience and could save you time and money.
"You need a community, and this roadmap from Preston - I can't tell you how many times early on I just needed someone to go to with a question."
Lesson 1: Don't Overcomplicate It
The Mistake: Overthinking the process, trying to reinvent strategies, or skipping proven steps.
What Brian Learned: Brian's success came from following the roadmap exactly as provided. He didn't try to customize the landlord scripts beyond tailoring them to his personality. He didn't skip the business setup steps. He followed the checklists in order.
Why This Matters: Many aspiring hosts spend months in analysis paralysis, researching endlessly, or trying to create their own approach. Brian went from joining the program to cash flow positive in under 90 days by trusting the process.
Lesson 2: Community Support Is Essential
The Mistake: Trying to figure everything out alone or lying to landlords about experience.
What Brian Learned: When facing the moment of signing a lease - the biggest commitment in the arbitrage process - Brian needed someone to review his numbers and validate his decision. Having community members look at the market, assess the property, and give a "thumbs up" provided the confidence boost he needed.
Beyond decision support, Brian used the community as credibility for landlord pitches. Instead of lying about his experience or making unsubstantiated promises, he could honestly say he was part of a team with proven results and show evidence.
"That was the big step - I had done all the research and made phone calls, not a big deal there. But then when you're about to sign a lease, you're like, 'Man, am I about to do the right thing?' Just having someone else there to look through your numbers, look at the market, do their own assessment, and then say 'thumbs up, I think this is a solid property, if it was me I'd go for it' - that just gave me the boost that I needed."
Lesson 3: Short-Term Rentals Can Be Better Than Long-Term
The Mistake: Assuming short-term rentals are more work than they're worth compared to traditional rentals.
What Brian Learned: Brian's long-term rental experience taught him that tenant turnover every 1-3 years creates significant work. With short-term rentals, professional cleaning after every guest actually prevents the accumulation of issues he dealt with in long-term properties.
Key differences Brian observed:
- Payment timing: Short-term guests pay before arriving; long-term tenants sometimes pay late
- Property condition: Regular professional cleaning prevents long-term damage
- Guest quality: Properly vetted short-term guests often treat properties better than long-term tenants
- Cash flow: Higher potential with short-term rentals
Lesson 4: Start Local, Then Expand
The Mistake: Trying to set up properties remotely before understanding the hands-on aspects of the business.
What Brian Learned: Brian intentionally started with a property close to home so he could be hands-on with staging, photography, and the initial guest experience. This let him learn the business thoroughly before attempting remote management.
Starting local also let him build relationships with cleaners, handymen, and other service providers. Now he can add more properties in the same market efficiently, leveraging the infrastructure he's already built.
"I really appreciate the advice and guidance you give on remote setup. For me personally, I just wanted to be really hands-on with my very first property. I wanted to be there, I wanted to stage it, I wanted to see what things were looking like from beginning to end."
Lesson 5: Automation Is Key
The Mistake: Managing everything manually and burning out on guest communication.
What Brian Learned: By following the automation strategies in the roadmap, Brian manages his property with just 1-2 hours per week. Automated messages handle most guest communication, and he only steps in for special questions or unique situations.
The automation Brian implemented:
- Automated messaging: Welcome messages, check-in instructions, and follow-ups
- Professional cleaning: Scheduled automatically after each checkout
- Guest notifications: New booking alerts that trigger automated workflows
Why This Matters: Without automation, Brian couldn't run this business alongside his full-time IT job. The systems make it possible to host while working 40+ hours per week.
Best Tools for Airbnb Arbitrage: Brian's Tech Stack
Brian manages his property with minimal time using automation and professional services. Here's his approach to running the business efficiently.
| Category | Brian's Approach | Purpose |
|---|---|---|
| Property Search | Zillow | Finding rental properties in target market |
| Guest Communication | Automated messaging | 24/7 guest support without constant monitoring |
| Cleaning | Professional cleaner | Consistent quality after every guest |
| Photography | Professional photographer with STR experience | Listings that show real guest experience |
| Platforms | Airbnb + Vrbo | Maximum exposure to potential guests |
Professional Photography
What Brian did differently: Brian hired a professional photographer specifically experienced with short-term rentals. The key instruction: stage for photos, but make sure the photos show what guests will actually experience when they arrive.
Too many listings have staged photos that don't match reality, leading to disappointed guests and negative reviews. Brian's approach ensures his listing photos are beautiful but authentic.
"We made sure everything looked good, that it was staged nice, but then that's how it's going to look when you enter this home. You're going to get exactly what you were hoping to get when you looked at the photos on our listing."
Automated Guest Communication
How it works: When a new booking comes in, Brian gets a notification. Automated messages go out for booking confirmation, check-in instructions, during-stay check-ins, and checkout reminders. Brian only handles special questions that fall outside the automated responses.
This system is what makes 1-2 hours per week possible while working full-time.
Professional Cleaning
Why it matters: Brian's experience with long-term rentals showed him that infrequent turnovers led to accumulated issues. With professional cleaning after every short-term guest, the property stays in excellent condition, preventing the major turnover work he experienced with long-term tenants.
Brian's Advice for Airbnb Arbitrage Beginners
"You need a community. I can't tell you how many times early on I just needed someone to go to with a question, and it gave me that confidence to move forward when I was able to have someone respond directly to me with advice about the property I was thinking about leasing."
If Brian were advising someone starting today, here's what he would emphasize:
Step 1: Get Organized First (Week 1)
There are organizational skills required to set up this business properly. Brian recommends having checklists and knowing what you need to do first, second, and third. The Legacy Investing Show roadmap provided this structure, including tasks many people don't think about: getting the business bank account open, setting up the LLC, creating a website.
Key tasks to organize upfront:
Business entity formation (LLC)
Business bank account
Business website (for landlord credibility)
Target market identification
Property criteria definition
Step 2: Find Your Community (Before Property Search)
Brian emphasizes joining a community before searching for properties. The community serves multiple purposes: answering questions, reviewing potential deals, providing landlord pitch credibility, and offering support when you're about to sign a lease and second-guessing yourself.
Step 3: Start Hands-On (First Property)
For your first property, Brian recommends being physically present for setup. Stage it yourself, attend the professional photo shoot, experience the property as a guest would. This hands-on approach teaches you what guests experience and helps you create better listings.
Step 4: Build Local Infrastructure (Properties 2-3)
Before expanding to new markets, leverage the infrastructure you've built locally. Brian plans to add more properties in his Iowa market specifically because he's already done the footwork: reliable cleaners, handyman relationships, understanding of local demand.
Step 5: Expand Remotely (Properties 4+)
Once you understand the business thoroughly and have proven systems, you can expand into more profitable markets remotely. Brian plans to eventually target markets further from home, following the remote setup strategies in the roadmap.
Watch Brian's Full Interview
Video highlights:
0:00 - Brian's IT background and why he chose arbitrage
3:30 - Long-term vs. short-term rental comparison
6:45 - Finding properties on Zillow
9:15 - Convincing multiple landlords
12:00 - Property walkthrough and design choices
16:30 - Cash flow numbers and projections
19:00 - Standing out from competition
21:30 - Future goals: one property per quarter
24:00 - Lifestyle impact and time investment
26:30 - Advice for beginners
Frequently Asked Questions
How much money can you make with Airbnb arbitrage while working full-time?
Brian generates $1,500-$2,000/month in cash flow from one 4-bedroom property in Iowa while working full-time in IT. The key is automation: automated messaging handles most guest communication, and a professional cleaner maintains the property. Brian spends just 1-2 hours per week on property management.
The actual income depends on your market, property type, and occupancy rates. Brian chose a historic property that appeals to families and weekend travelers, with premium positioning for the local tourism market.
Is Airbnb arbitrage still profitable in 2026?
Based on Brian's experience, yes. He started in January 2026 and was cash flow positive by March - just two months after launching. His Iowa property competes successfully despite some competition from other large homes in the market.
Success factors Brian identified:
Choosing a property that genuinely excites you (and will excite guests)
Professional photography showing the real guest experience
Responsive listing updates (adding office space, kid amenities based on feedback)
Competitive pricing while establishing reputation
Working toward Superhost status for better ranking
What's the biggest risk with Airbnb arbitrage?
Brian identifies the lease signing moment as the biggest psychological hurdle. You're committing to monthly rent before having proven you can generate bookings. His risk mitigation strategies:
Get community feedback on the deal before signing
Run conservative revenue projections
Have reserves for slow months (he launched in winter)
Build toward Superhost status to improve booking velocity
Brian also notes that short-term rental guests, when properly vetted, often treat properties better than long-term tenants. Regular professional cleaning prevents the damage accumulation he experienced with long-term rentals.
Start Your Airbnb Arbitrage Journey
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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 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 Brian O'Leary's video interview conducted in 2026. All statistics and quotes are directly from Brian's experience. Individual results vary based on market, effort, and capital invested.
Last updated: March 30, 2026
Preston Seo
Real estate investor and financial educator helping people build generational wealth through smart investing strategies.
Frequently Asked Questions
Brian generates $1,500-$2,000/month in cash flow from one 4-bedroom property in Iowa while working full-time in IT. He spends just 1-2 hours per week managing the property thanks to automation systems and a professional cleaner.
Brian contacted 4-5 landlords on Zillow, got 3 to agree to meetings, and used Legacy Investing Show's scripts tailored to his personality. The key was showing confidence in the business model and providing links to successful Superhost listings from the community as proof of quality.
Yes. Brian started in January 2026 and was cash flow positive by March. His Iowa property targets family travelers and weekend getaways. Success depends on market selection, property appeal, and operational efficiency.
Brian joined Legacy Investing Show in early January, secured his property by end of January, and went live on Airbnb in February. Most students get their first property in 30-60 days following the roadmap.
No. Brian had one long-term rental but no short-term rental experience. He followed Legacy Investing Show's roadmap step-by-step and relied on the community for guidance. His IT background helped with organization and automation.
Brian chose a historic 4-bedroom home with a front porch overlooking the Mississippi River. He selected it because he and his wife "didn't want to leave" - if you're excited about a property, guests will be too. The home sleeps 10 guests and targets families.
Brian spends 1-2 hours per week on his property. Automated messaging handles most guest communication, and a professional cleaner maintains the property. He only handles special questions and backend tasks like bookkeeping.
Short-term rentals require more turnover but offer higher cash flow potential. Brian's long-term rental had issues with damage accumulating over 1-3 year tenancies. With short-term rentals, professional cleaning after every guest prevents long-term damage, and you get paid upfront before guests arrive.
Based on Brian's results, the program provided crucial landlord scripts, business setup checklists, and community support. He used the community to prove credibility to landlords and got direct feedback on his deal before signing. The structured roadmap helped him launch in under 60 days.
Yes. Brian chose Iowa specifically for its historic Mississippi River properties and tourism appeal. Smaller markets often have less competition, landlords more open to arbitrage, and unique properties that stand out on Airbnb. His property offers views of three states from the front porch.