How Christopher Went from Multiple Failures to $1,700/Month Airbnb Cash Flow in Louisiana (2026)

$1,700
Monthly Cash Flow
Conservative estimate Student Interview, 2023
1
Properties
Louisiana market
50-70
Landlord Calls
Before first yes
3 Years
Lease Term
With renewal option
Pool
Key Amenity
Only 6% of listings
29
Age
Started from scratch

Christopher Bamford earns $1,700 per month in cash flow from his first Airbnb arbitrage property in Louisiana. After calling 50-70 landlords, experiencing multiple failed deals, and pushing through countless rejections, the 29-year-old from Louisiana secured a 3-year lease on a property with a pool, set it up with his fiance, and is now planning rapid expansion. His story proves that grit and determination matter more than background or experience in the rental arbitrage business.

This case study breaks down exactly how Christopher overcame the obstacles that stop most beginners, including his landlord scripts, negotiation tactics, and the mindset shifts that made success possible.

In this article:


Quick Results: Christopher's Airbnb Arbitrage Numbers

Metric Value Context
Monthly Cash Flow $1,700+ Conservative estimate
Properties 1 (more planned) Louisiana market
Lease Term 3 years With renewal option
Landlord Calls Made 50-70 Before first successful deal
Failed Deals Multiple Numbers didn't work
Key Amenity Pool Only 6% of listings have pools
Decor Style Boho theme Competitive differentiation
Goal Timeline 2+ properties by next year Aggressive but realistic

Christopher's Background: From Oil and Gas to Airbnb Entrepreneur

You don't need a privileged background to build a successful Airbnb business. Christopher didn't come from wealthy parents—everything he invested came from what he and his fiance saved themselves. His story demonstrates that persistence and proper education can overcome any starting point.

The Entrepreneurial Spirit

Christopher has always had an entrepreneurial drive. Before Airbnb arbitrage, he started an eBay business with just $70, going to garage sales and flipping items for profit. This early hustle taught him the fundamentals of buying low, selling high, and building something from nothing.

Eventually, Christopher entered the oil and gas industry in Louisiana, which provided stable income but left his eBay business on the back burner. The corporate world paid the bills, but he never lost the desire to build something of his own—something that could provide financial freedom beyond a paycheck.

Finding the Path to Real Estate

Christopher had been interested in real estate for years but couldn't find his way in. The barriers seemed insurmountable: the capital requirements, the lack of guidance, not knowing where to start. Traditional real estate investing with down payments and mortgages felt out of reach.

Then he discovered Airbnb arbitrage through Preston's YouTube videos. The model made sense—rent properties, furnish them, and sublease on Airbnb for profit without needing to buy real estate. Christopher watched videos for months, researching and learning before taking action.

"I've always kind of been in the entrepreneur spirit. I started with like 70 bucks going to garage sales and started an eBay business. I could really never find my way into real estate with the capital that you have to have and just not knowing and not necessarily having guidance on it."

Key Takeaway: Christopher's entrepreneurial background—even just garage sale flipping—gave him the mindset needed for Airbnb arbitrage: see an opportunity, take action, learn from results.


The Airbnb Arbitrage Journey: Christopher's Timeline

The Learning Phase: Months of Preparation

Situation: Christopher spent months watching YouTube videos and discussing the opportunity with his fiance.

The decision to invest in education wasn't easy. Christopher and his fiance watched Preston's videos together, discussing whether this could be their path to financial freedom. The unknown was scary—buying a course, learning a new business model, calling strangers and asking them to let you rent their property differently than traditional tenants.

Christopher committed to the process completely. He watched videos over and over again to make sure concepts set in. He took notes, went step by step, and rewatched anything he didn't fully understand. Market research was particularly challenging—he kept going back to the training videos until he felt confident.

"There was a lot of times that I was just going through market research and I'm not fully understanding—go back and watch the videos. Is it gonna get you—are you going to be able to understand, are you going to get it? And then it got to a point like all right now I've kind of got the market research down, it's time to start calling landlords."

The Calling Campaign: 50-70 Landlords

Situation: Christopher made 50-70 landlord calls, experiencing rejection after rejection.

Calling landlords was where the real challenge began. Christopher's first call went to a lady in Louisiana—he went straight off the script and sounded, by his own admission, almost like a robot. It wasn't terrible, but it wasn't great either. The landlord was nice and respectful, but the call didn't lead anywhere.

The first 10 calls produced no yeses and not even any maybes. Christopher faced every type of response: people who hung up immediately, people who were interested but didn't understand the model, and people who seemed interested until the numbers didn't work.

Rather than give up, Christopher called his father and practiced. For about an hour and a half, they ran through the script over and over, with his father playing the role of a landlord. Repetition built muscle memory—the script started to become natural rather than robotic.

"I called my father and I started practicing with him. I was like hey look you're going to be a landlord, I'm gonna come in—and I probably sat on the phone with him for probably about an hour and a half and just went over the script, went over the script. Just repetition is what it is because it starts to become memory, you just start to be able to spit it out."

The Failed Deals That Built Character

Situation: Multiple deals fell through because the numbers didn't work.

After improving his pitch, Christopher started getting positive responses. But interest doesn't equal closed deals. Several properties fell through at the final stages:

Deal 1: A couple really wanted to work with Christopher. They liked his pitch, understood the model, and were ready to move forward. But when Christopher ran the numbers, the return just wasn't there. The risk was too high for the potential reward. He had to walk away despite the emotional pull.

Deal 2: A landlord who already owned several Airbnbs had fully furnished properties available. Christopher was ready to offer the asking rent price. But the landlord wanted a premium—extra money on top of standard rent—which threw off all the projections. Christopher tried multiple times to negotiate, but the landlord wouldn't budge.

Each failed deal was a learning opportunity. Christopher learned to separate emotions from business decisions, to walk away when numbers don't work regardless of how beautiful a property looks, and to keep searching rather than forcing a bad deal.

"You start getting excited and then the numbers just don't work and you gotta take your feelings out of it because that's what it comes down to—it comes down to the numbers and this is a business."

The Breakthrough: Finding the Right Landlord

Situation: After dozens of calls, Christopher found a landlord with 26 properties who took a chance on him.

The winning deal came through a property listing that appeared in Christopher's saved search alerts. He called and left a voicemail with no response. Then he got a message back saying it was a realty company—typically a dead end since you can't usually reach the actual landlord.

But Christopher persisted. He asked to speak on the phone about the property. It turned out the person he'd been messaging was actually the landlord—someone who owned 26 properties plus an existing Airbnb.

During the pitch, the landlord asked the question that scares most beginners: "So how many of these do you have under your belt?"

Christopher chose honesty. He explained this was his first property, but emphasized his preparation: he'd invested in his education, taken every necessary step, done the research, and had a team with coaches and mentors backing him. He mentioned Preston's name and the Legacy Investing Show.

The landlord's response changed everything. He shared that seven years ago, someone had taken a chance on him when he was just starting out. Now he had 26 properties. He wanted to pay that forward.

"He kind of told me a story where we kind of connected. I was like hey this is my first investment property and he was like a guy took a chance on me seven years ago and now I have 26 properties. If the numbers work and everything's legit on your end, I would love to get you into investing."

The Negotiation:

  • Christopher asked for a 4-year lease

  • The landlord preferred 1 year (too short for arbitrage economics)

  • They settled on 3 years with a possible renewal

  • The landlord was flexible on numbers and easy to work with

  • Christopher started a month earlier than planned (February instead of April)


How to Choose a Market for Airbnb Arbitrage: Christopher's Louisiana Strategy

Starting in your local market reduces complexity for your first property. Christopher focused on Louisiana, where he already lived, allowing him to set up and manage the property more easily while learning the business.

Why Louisiana Works

Christopher chose to start locally for practical reasons. He could visit the property, meet with potential landlords in person, and oversee the setup process directly. For a first-time operator, this hands-on involvement is invaluable for building confidence and learning the systems.

Louisiana offers diverse short-term rental opportunities, from New Orleans tourism to suburban family travel. The market has less saturation than major metros like Austin or Nashville, creating opportunities for operators willing to put in the work.

Christopher's Property Criteria

Christopher's successful property included several key features:

Must-Have: Pool

Only 6% of Airbnb properties have pools. Christopher secured one of these rare listings, immediately differentiating from 94% of the competition. In hot Southern climates, a pool isn't just a nice-to-have—it's a booking driver.

Planned Addition: Hot Tub

Only 6% of properties also have hot tubs. Christopher plans to add one once profit comes in, further reducing his competitive set and commanding premium pricing.

Space and Layout

The property has a large backyard, room for outdoor activities, and space for guests to spread out. This appeals to families and groups looking for more than just a place to sleep.

"I think only six percent of properties have pools. I think only six percent of properties have hot tubs. So once we get some profit back in, we're gonna put a hot tub there immediately and just kind of stand out from the competition."


Airbnb Arbitrage Strategies That Actually Work: Christopher's Playbook

The difference between those who succeed and those who quit comes down to specific strategies applied consistently. Christopher's success wasn't luck—it was the result of deliberate approaches that most beginners don't implement.

Strategy 1: The Volume Game

What it is: Making massive numbers of landlord calls rather than expecting quick success.

Why it works: Most people give up after 5-10 calls. Christopher made 50-70 calls before securing his deal. This volume approach means you'll eventually find the right landlord even if your conversion rate is low. Each call also improves your pitch, creating a compounding effect.

Christopher emphasizes that this is truly a numbers game. Eventually, you will find someone willing to work with you. The question is whether you'll make enough calls to reach that person.

Christopher's Results with This Strategy:

  • Pitch improved dramatically from call 1 to call 70

  • Learned what objections to expect and how to handle them

  • Found a landlord who became a potential long-term partner

"It's really a numbers game. Eventually you are going to get somebody that you can work with that is going to say yes. So it's kind of just getting over that hump."

Strategy 2: Building Rapport Before the Pitch

What it is: Opening conversations by complimenting the property and building connection before presenting the arbitrage opportunity.

Why it works: Landlords receive cold calls constantly. Starting with genuine compliments and interest makes you memorable. By the time you present your pitch, the landlord already likes you and is more receptive.

Christopher evolved from going straight into his pitch (which felt robotic) to leading with rapport. He'd comment on how incredible the house looked, ask about the yard, compliment any renovations. Landlords would open up—"Yeah, we bought it eight years ago, did a few renovations"—and suddenly the conversation felt collaborative rather than transactional.

Christopher's Results with This Strategy:

  • Conversations lasted longer and felt more natural

  • Landlords became more receptive to the business model

  • Even rejections were polite rather than hang-ups

"I didn't really go straight into like hey this is what I want to do—I was kind of starting to build rapport with these people. Hey the house is incredible, it looks incredible, the yard is great, beautiful home by the way, just kind of building a little bit of rapport."

Strategy 3: Removing Emotions from Numbers

What it is: Making decisions based purely on financial analysis, regardless of how much you like a property.

Why it works: Beautiful properties can lose money. Ugly properties can be cash cows. Christopher learned to run the numbers first and walk away from deals that looked great on paper but didn't pencil out financially.

When Christopher found properties he loved, the temptation was to fudge the numbers—maybe occupancy will be higher, maybe expenses will be lower. But that's exactly how people lose money. The data must drive the decision.

Christopher's Results with This Strategy:

  • Avoided several money-losing deals

  • Eventually found a property where numbers and appeal aligned

  • Built confidence in his analysis process

"You start getting excited and then the numbers just don't work and you gotta take your feelings out of it. That's what it comes down to—it comes down to the numbers and this is a business."

Strategy 4: Differentiating Through Rare Amenities

What it is: Focusing on properties with amenities that only a small percentage of competitors offer.

Why it works: When guests filter for specific amenities, your property appears while most competitors don't. Christopher's pool immediately puts him in the top 6% of listings. Adding a hot tub will narrow competition further.

Beyond the pool, Christopher invested in differentiation through decor (boho theme), outdoor amenities (fire pit, grill, giant Jenga), and a game room for kids. Every addition makes the property harder to replicate and easier to justify premium pricing.

Christopher's Results with This Strategy:

  • Property stands out in search results

  • Confident in beating conservative $1,700/month estimate

  • Clear roadmap for reinvesting profits (hot tub)

"We definitely want to hone in on this one and lock this one down and make sure we know exactly what we're doing. We're looking at the competition—that's a big thing—see what's working for them, kind of go off of that, take bits of it, put it in yours."

Strategy 5: Community Integration and Local Partnerships

What it is: Building relationships with neighbors and local businesses to enhance the guest experience and property protection.

Why it works: Neighbors who know you are more likely to watch out for your property rather than complain about guests. Local business partnerships (like gift cards for welcome packets) add value for guests at minimal cost while supporting the community.

Christopher took his laptop to six local restaurants and asked about gift cards for his welcome packets. He was amazed how receptive businesses were when he explained his goal: give guests a great experience and drive traffic to local establishments. He secured gift cards from multiple restaurants and ice cream shops.

He also hosted a grill-out for the neighbors. Some came over, met him and his fiance, and learned about the business. Now those neighbors watch the property and even plan to have visiting family stay there instead of at their own homes.

Christopher's Results with This Strategy:

  • Neighbors agreed to watch the property

  • Local businesses provided gift cards for welcome packets

  • Built potential future booking pipeline (neighbors' visiting families)

"I was like the main thing is I want to give my guests a great experience. I want to improve the area, I want to be a part of the community. I want all of us to come together, work together. And when I explained it like that they were more than happy."

Christopher's Airbnb Arbitrage Results: The Numbers

Christopher generates $1,700/month conservatively from his first property. Here's the complete breakdown of his Airbnb arbitrage setup and projections.

Financial Breakdown

Metric Value Notes
Monthly Cash Flow $1,700+ Conservative estimate
Expected Actual Higher than $1,700 Pool and amenities should outperform
Lease Term 3 years With renewal option
Original Ask 4-year lease Negotiated down
Start Date February/March Started month early at landlord's request

Property Setup Details

Christopher and his fiance personally set up the entire property. The process included:

Furnishing:

  • Used Legacy Investing Show room-by-room checklist

  • Boho theme throughout for cohesive aesthetic

  • Quality outdoor furniture for the pool area

  • Fire pit and grill for outdoor entertainment

  • Game room setup for kids

  • Giant Jenga (Christopher cut 2x4s into 10.5-inch lengths himself)

Deep Cleaning:

  • Scrubbed every door and baseboard

  • Cleaned inside all cabinets

  • Detailed every bathroom

  • Prepared the property as if they were the guests

Operations Setup:

  • Hired cleaners

  • Arranged handyman on call

  • Secured lawn care service

  • Set up pool maintenance

  • Professional photography scheduled

"It's an experience to get out there, put an entire house together literally. My fiance was there a couple weeks before me, and then I was able to get off work, go out there. It starts to become a home—you're sitting here in this beautiful home putting it all together, you're starting to see that vision, that light at the end of the tunnel."

Key Milestones Achieved

  • Made 50-70 landlord calls: Persistence paid off despite early rejections

  • Secured 3-year lease: Long enough for sustainable arbitrage economics

  • Found property with pool: Top 6% of listings by amenity

  • Built local partnerships: Gift cards from restaurants and ice cream shops

  • Established neighbor relationships: Extra eyes on the property

  • Set up full operations team: Cleaners, handyman, lawn care, pool service

  • Getting married in October: Jamaica honeymoon planned


Airbnb Arbitrage Lessons: What Christopher Learned the Hard Way

These five lessons took Christopher from complete beginner to property owner in months. Each one came from real experience and could save you months of frustration.

"You never fail, you only learn. That's kind of how we've been looking at it—and here we are."

Lesson 1: Hard Work Beats Talent

The Mistake: Assuming you need natural sales ability or special skills to succeed.

What Christopher Learned: Christopher admits he's not someone who retains information quickly or naturally excels at talking to strangers. He had to watch training videos over and over. He had to practice his landlord script with his father for 90 minutes. He had to make 50-70 calls before getting comfortable.

But that hard work compounded. By call 50, he was significantly better than on call 1. The skills that felt impossible at first became second nature through repetition.

Why This Matters: Most people believe they either have what it takes or they don't. The truth is that anyone willing to put in the repetitions can develop the necessary skills. Talent is overrated; persistence is underrated.

"Hard work beats out talent most of the time. A lot of us people, we're just not necessarily skilled in talking to people. But repetition—doing it over and over and over—you're gonna develop the skill."

Lesson 2: You Never Fail, You Only Learn

The Mistake: Viewing failed deals and rejections as personal failures.
What Christopher Learned: Every rejection taught him something. Hang-ups showed him his opening needed work. Deals that fell through on numbers taught him to analyze earlier. Landlords who wanted premiums taught him which types to avoid.
Christopher reframed every setback as a lesson. Instead of getting discouraged by the couple who wanted to work with him but whose numbers didn't work, he learned to qualify deals earlier and not get emotionally attached before analysis.
Why This Matters: The people who quit do so because they interpret failures as signs they shouldn't continue. The people who succeed interpret failures as steps in the process.

Lesson 3: Make the Script Your Own

The Mistake: Reading a script word-for-word and sounding like a robot.
What Christopher Learned: The provided scripts are starting points, not final products. Christopher's first call was robotic because he read the script verbatim. Through practice and real calls, he learned which parts resonated and which fell flat. He started building rapport first, leading with security benefits, and adapting his language to each conversation.
Why This Matters: Landlords can tell when you're reading a script. Natural conversation builds trust; robotic pitches create suspicion. The script gives you the what to say; you develop the how.

"From my first call to within the middle to the end, I started realizing like what people like to hear. I never started out with just like hey this is what I'm gonna do—I would kind of give them some of the securities first."

Lesson 4: The Numbers Don't Lie

The Mistake: Letting excitement about a property override financial analysis.
What Christopher Learned: Christopher and his fiance got excited about several properties before the numbers killed the deals. A beautiful home with the wrong rent-to-revenue ratio will lose money no matter how much you like it. A landlord wanting premium rent will destroy your margins regardless of their friendliness.
The discipline to walk away from attractive-looking deals is what separates successful arbitrage operators from those who lose money.
Why This Matters: Airbnb arbitrage is a business, not a hobby. Businesses survive on margins, not aesthetics. Falling in love with properties before analyzing numbers is the fastest path to failure.

Lesson 5: A Supportive Partner Changes Everything

The Mistake: Trying to build a business without support from the people closest to you.
What Christopher Learned: Christopher's fiance was there from the beginning—watching videos together, discussing the opportunity, encouraging him through rejections, helping set up the property. When he came home after a day of nothing but nos, she was there to lift him up.
For those without a supportive spouse, Christopher points to the Legacy Investing Show community as providing similar encouragement. Seeing others go through the same struggles and achieve success keeps you motivated when things get hard.
Why This Matters: Entrepreneurship is lonely. Having someone who believes in you during the hard times—whether a spouse, friend, or community—can be the difference between quitting and breaking through.

"A support system is in my opinion the most important—to have those people, like-minded people. You're seeing what they're going through, they're seeing what you're going through, and you just pick and choose and benefit each other."

Best Tools for Airbnb Arbitrage: Christopher's Setup

Christopher used a combination of training resources, operational tools, and local services to launch his property. Here's the complete stack that powers his $1,700/month business.

Essential Tools Overview

Category Tool/Resource Purpose Why Christopher Chose It
Training Legacy Investing Show Step-by-step education Detailed course with coaching and community
Property Finding Saved search alerts New listing notifications Automated daily/weekly alerts for new properties
Furnishing Guide LIS Room Checklists Setup organization Detailed lists for every room
Cleaning Local cleaning team Turnover management Reliable local operators
Maintenance Local handyman On-call repairs Quick response for guest issues
Pool Service Local pool company Pool maintenance Essential for pool property
Lawn Care Local service Exterior maintenance Curb appeal matters for reviews
Photography Professional photographer Listing photos Quality photos drive bookings

Legacy Investing Show Resources

What it provides: Comprehensive training covering market research, landlord outreach, lease negotiation, property setup, listing optimization, and scaling.

How Christopher used it: Watched videos multiple times until concepts stuck. Used the room-by-room furnishing checklists. Connected with coaches Dustin and Sam when he had questions. Gained confidence from seeing other students succeed.

Pro tip: "If you're missing something, go back and watch it again. It's there for you. You have a community of people, you have the coaches, you have the mentors."

Saved Search Alerts

What it does: Automatically notifies you when new rental listings matching your criteria hit the market.

How Christopher used it: Set up alerts for his target area. The winning property came through one of these automated notifications. By being first to respond, he got in front of a landlord with 26 properties.

Pro tip: Set alerts for multiple areas within your target market to maximize opportunities.

Local Service Providers

What they do: Handle the operational aspects of running the property—cleaning, maintenance, lawn care, pool service.

How Christopher found them: Local referrals and building relationships in the community. Having the cleaners pick up gift cards from local ice cream shops shows the level of integration.

Pro tip: Your cleaners are your boots on the ground. Build a strong relationship with them—they're often first to notice issues.


Christopher's Advice for Airbnb Arbitrage Beginners

"There's a thousand reasons that you can tell yourself to not do it. Every year for the rest of your life there's going to be something out there that's going to tell you how you don't do that. You kind of push those away if you've got a proven plan and you see that it's working for people."

If Christopher were starting over today, here's exactly what he would do:

Step 1: Getting the Right Mindset (Week 1)

Christopher emphasizes that mindset comes before tactics. The same education system teaches most people the same limiting beliefs. Nobody teaches financial literacy, investing, or entrepreneurship in school.

The Mindset Shift:

  • Stop thinking about what could go wrong

  • Start thinking about what could go right

  • Recognize that working a 9-to-5 for life is also scary

  • Understand that if others are doing it, you can too

Christopher didn't come from wealth. His parents weren't rich. Everything he and his fiance invested came from their own savings. If background determined success, he wouldn't have made it. But it doesn't—mindset does.

"People thinking like ah I don't have rich parents that'll invest this kind of money—it doesn't matter. If you apply yourself, it might take you a little bit longer to save up the money, but once you do you'll get in there and that's your first step."

Step 2: Invest in Your Education (Week 1-2)

Christopher strongly recommends buying a comprehensive course rather than piecing together free YouTube content. His reasoning:

Why Courses Beat Free Content:

  • Free videos are scattered across different creators with different approaches

  • You'll miss critical tips trying to learn from random sources

  • A structured course provides step-by-step guidance

  • Community and coaching provide support when you're stuck

  • Seeing others succeed in the same program provides motivation

Christopher tried watching various YouTube videos before joining Legacy Investing Show. The free approach was confusing—different people with different methods, no clear path forward. The structured course changed everything.

"Getting a detailed plan is 100% what I recommend. Having people there to back you up when you're just stepping into this industry—I would 100% recommend getting a detailed plan and going with a course. You got to invest into your education, invest into yourself."

Step 3: Take Massive Action (Week 3-8)

Knowledge without action produces nothing. Christopher emphasizes that you have to make the calls, even when they're uncomfortable.

Action Steps:

Christopher made at least 50-70 calls. Many people won't make 10. The ones who succeed are the ones who keep dialing.

Step 4: Make Sacrifices to Scale Faster (Ongoing)

Christopher and his fiance changed their spending habits to fund the business. He sold both of his four-wheelers—toys he enjoyed—to put money toward scaling faster.

The Sacrifice Mindset:

  • Cut unnecessary expenses

  • Sell items that don't produce income

  • Delay gratification for long-term freedom

  • Budget aggressively

  • Reinvest profits rather than spending them

Most people want the results without the sacrifices. They want to keep their toys AND build a business. Christopher chose differently.

"We're starting to see that light. It's possible—people are doing this every single day and they're just average Joes like us. Let's go for it. Let's start changing things in our life and making sacrifices to get to that point."


Watch Christopher's Full Interview

Video highlights:

  • 0:00 - Introduction and background in oil and gas

  • 3:15 - Starting the Airbnb journey with his fiance

  • 7:30 - The 50-70 landlord calls and early failures

  • 12:45 - Practicing scripts with his father

  • 16:20 - Finding the landlord with 26 properties

  • 20:00 - Setting up the property with his fiance

  • 23:30 - Building local partnerships for welcome packets

  • 26:45 - Advice for beginners


Frequently Asked Questions

How much money can you really make with Airbnb arbitrage?

Christopher projects $1,700/month conservatively from his first property in Louisiana. This includes a property with a pool (only 6% of listings), boho-style decor, outdoor amenities, and a game room. He expects actual performance to exceed this estimate based on his competitive positioning.

Results vary significantly based on market, property quality, amenities, and operational execution. Properties with rare amenities like pools command premium pricing and higher occupancy rates.

Is Airbnb arbitrage still worth it in 2026?

Based on Christopher's experience, yes. He started in a competitive environment, faced numerous rejections, and still secured a profitable deal. The key success factors remain consistent: persistence in landlord outreach, proper market research, conservative number analysis, and operational excellence.

Christopher notes that every year, people say don't do this or that. There's always something that could stop you. The people who succeed push through regardless.

What's the biggest challenge with Airbnb arbitrage?

Christopher identifies landlord outreach as the biggest initial challenge. Making 50-70 calls, dealing with rejections, and perfecting your pitch requires significant mental fortitude. Many people give up after a handful of nos.

The second challenge is removing emotions from decision-making. Christopher walked away from multiple deals where he liked the property but the numbers didn't work. This discipline is essential but difficult.


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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 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 Christopher Bamford's video interview conducted in 2023. All statistics and quotes are directly from Christopher's experience. Individual results vary based on market, effort, and capital invested.

Last updated: April 8, 2026

Preston Seo

Real estate investor and financial educator helping people build generational wealth through smart investing strategies.

Frequently Asked Questions

Christopher generates $1,700/month conservatively from his first property in Louisiana. This includes a property with a pool, boho-style decor, and amenities like a fire pit and outdoor games. He expects actual returns to exceed this conservative estimate.

Christopher called 50-70 landlords before securing his first deal. He experienced hang-ups, polite rejections, and several deals that fell through because the numbers didn't work. Persistence and volume are key to success.

Yes. Christopher started in 2023-2024 and locked up his first property generating $1,700/month cash flow. He secured a 3-year lease with options to renew and plans to scale to multiple properties. Success depends on persistence, proper market research, and landlord negotiation skills.

Christopher's timeline included months of learning, practicing scripts with his father, and calling 50-70 landlords. He secured a 3-year lease and set up the property within a few weeks of signing. Most Legacy Investing Show students get their first property in 30-60 days with focused effort.

No. Christopher came from the oil and gas industry with no real estate experience. He started an eBay business with just $70 going to garage sales before transitioning to Airbnb arbitrage. His success came from following a proven system and persistent effort.

Startup costs include security deposit, first month's rent, furniture, supplies, and decor. Christopher and his fiance saved up over time, changed spending habits, and even sold personal items (four-wheelers) to fund their business faster. The exact amount varies by market and property size.

Christopher's property includes a pool (only 6% of properties have pools), fire pit, grill, outdoor games including giant Jenga, boho-style decor, and plans to add a hot tub (also only 6% of properties have hot tubs). He also secured gift cards from local restaurants and ice cream shops for welcome packets.

Christopher strongly recommends getting a detailed course over trying to learn from random YouTube videos. He credits the step-by-step guidance, community support, and coaching from mentors Dustin and Sam as essential to his success. He's now encouraging his brother and friends to join.

Christopher evolved his approach from robotic script-reading to building rapport first. He compliments the property, asks about its history, then presents the value proposition: better property care, maintenance handling, and reliable income. He was honest about being a first-time operator, which actually helped build trust with his landlord.

Christopher credits his fiance as essential to his success. She watched videos with him, encouraged him through rejections, helped set up the property, and manages aspects of the business. Even without a supportive spouse, the Legacy Investing Show community provides similar encouragement and accountability.

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