AI is changing short-term rental marketing—but not always for the better.

In this episode of the STR Investing Podcast, Taylor sits down with Conrad, founder of BuildUp Bookings, to break down what actually drives bookings in today’s crowded STR market.

They discuss how overused AI messaging can turn guests away, where automation still adds real value, and why authentic communication is becoming a competitive advantage for Airbnb hosts and property managers. Conrad shares practical insights from nearly a decade in STR marketing, helping operators rethink how they attract, convert, and retain guests.

Key topics covered:

• AI vs human messaging in STR marketing
• How to improve bookings without sounding automated
• Guest psychology and conversion fundamentals
• Marketing mistakes hurting Airbnb performance

If you want more bookings without relying on spammy AI tactics, this episode delivers clear, actionable insight.

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Episode Sponsored By:
STR Search

STR Search is the industry leading property finder service. They've helped investors acquire over 325+ profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com

In this Monday Market Data Report, co-host Mark Lumpkin breaks down the short-term rental numbers for Austin, one of the most talked-about STR markets in the country.

This episode dives deep into how revenue, occupancy, and nightly rates scale as bedroom count increases, and why Austin strongly rewards larger, high-performing properties.

You’ll learn:

• What 3-bedroom properties earn at average vs. top-tier performance levels
• Why adding a 4th bedroom can unlock a major revenue jump—even with slightly lower occupancy
• How 5-bedroom homes outperform smaller properties by tens of thousands per year
• Why 6+ bedroom homes in Austin are producing some of the highest STR revenues we’ve seen nationwide
• How higher nightly rates and strategic occupancy can lead to stronger net returns

The numbers show massive gaps between average listings and top performers—ranging from under $40K per year to well over $300K—making Austin a clear example of how property size and performance drive outcomes.

If you’re investing in Austin, underwriting a deal, or deciding whether expanding your floor plan is worth it, this episode gives you clear, data-backed insights to guide your strategy.

Have a market you want us to cover next? DM Mark and we’ll bring the data.

Cleaning issues, last-minute cancellations, and unreliable contractors are some of the biggest threats to STR performance.

Chris Rule, VP of Customer Experience at Turno, joins the show to explain how top operators are solving these problems—and what’s coming next for the industry.

Chris shares how Turno is helping hosts and property managers eliminate turnover chaos by connecting guest cleanliness reviews directly to cleaners, automating scheduling, and creating real accountability at scale. The conversation dives deep into why turnovers are one of the most stressful (and most overlooked) parts of short-term rental operations, and how better systems lead to better reviews, happier guests, and fewer late-night emergencies.

We also explore Turno’s rapidly expanding ecosystem, including global contractor coverage, cleaner guarantees, faster payouts, tax compliance, and what’s next beyond cleaning—including maintenance and handyman services designed specifically for STR operators.

Whether you’re managing one property or hundreds, this episode breaks down how professional operators are building reliable, scalable systems that protect performance and peace of mind.

Topics covered:

• Why turnovers make or break guest experience
• How guest cleanliness reviews create real cleaner accountability
• Preventing last-minute no-shows and operational emergencies
• Scaling cleaning and maintenance without growing headaches
• Turno’s expansion into maintenance and contractor services
• What STR operators should expect in 2026 and beyond

If you’re serious about running a high-performing short-term rental, this is a must-listen episode.

Get in touch with Chris:

LinkedIn: Chris Rule

Sign up at Turno here today!

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Episode Sponsored By:
STR Search

STR Search is the industry leading property finder service. They've helped investors acquire over 325+ profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com

In this episode, co-host Mark Lumpkin breaks down the short-term rental numbers for Big Bear Lake, one of Southern California’s most well-known mountain vacation markets.

This episode takes a data-driven look at how revenue, occupancy, and nightly rates shift dramatically by bedroom count — and why Big Bear Lake behaves very differently from many STR markets across the country.

You’ll hear insights on:

• Revenue potential from 3-bedroom through 6+ bedroom homes
• How much income each additional bedroom can unlock
• Occupancy trends that stand out compared to national averages
• The massive gap between average and top-performing properties
• Why larger homes dominate revenue in this market

Whether you already own in Big Bear Lake or you’re underwriting a potential deal, this episode gives you clear, actionable data to understand where the real upside lives.

In this episode of the STR Investing Podcast, Taylor sits down with Nate Klatt — CPA, former startup operator, and co-founder of HomeHop — to break down how he went from flipping houses with thin margins to building a short-term rental portfolio, launching a property management company, and raising STR investment funds.

Nate shares the real behind-the-scenes of scaling: why conservative underwriting matters when you’re taking friends-and-family money, how they structured investor returns, what changed once they brought in real design, and why they’re shifting toward bigger homes and higher-end amenities in their next fund.

In this episode, you’ll learn:

• Nate’s path from Michigan State football + CPA to real estate entrepreneur
• The biggest mistakes (and lessons) from their first flips
• Why they stopped chasing cheap renovations and started building properties people fall in love with
• How promissory notes helped them scale early — and why they eventually launched a fund
• The exact structure they used: preferred return, margins, and staying conservative on projections
• What it takes to build a real property management operation (tools, SOPs, and hiring VAs)
• Why larger homes and “hero amenities” are becoming the clearest path to outperforming in today’s market
• Where HomeHop is headed next: expansion decisions, fund strategy, and growth over the next 12–24 months

Connect with Nate:
LinkedIn: Nate Klatt
Website: homehop.com

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Episode Sponsored By:
STR Search

STR Search is the industry leading property finder service. They've helped investors acquire over 325+ profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com

It’s time for another Monday Morning Market Data Report — and this week we’re breaking down Flagstaff, Arizona.

Mark walks through what the numbers actually say across 3-bed, 4-bed, 5-bed, and 6+ bedroom STRs, including how revenue, ADR, and occupancy shift as you scale up in size. And what makes this one interesting: Flagstaff looks like a “middle-of-the-country” baseline market… until you hit the bigger homes.

In this episode, you’ll learn:

• What a “typical” 3-bedroom in Flagstaff earns vs. a top performer
• Why 4-bed homes can earn more even with slightly lower occupancy (and why that’s not a bad thing)
• The real value of adding a 5th bedroom — and when it becomes a revenue multiplier
• The wildest data point in this report: 6+ bedrooms nearly doubling 5-bedroom top-end revenue
• How to use percentile data to set realistic revenue targets before you buy

If you’re trying to decide what size property you need to hit your STR goals — and whether it’s worth stretching into a bigger home — this Flagstaff breakdown makes it crystal clear.

Taylor sits down with Jacob — a Bay Area tech professional turned short-term rental investor — to unpack the real story behind taking a “big swing” on a remote, high-risk property… and having it pay off.

Jacob shares how growing up in San Francisco made real estate feel impossible, why a single long-distance rental accidentally sparked his investing journey, and what finally pushed him from long-term rentals into STRs.

Then it gets real: an $800K lakefront property in Northern Michigan, a massive footprint (with an indoor pool), limited comps, sky-high interest rates, and the kind of renovation logistics that make most investors freeze. Jacob walks through the stress, the surprises, the launch chaos, and the unexpected part of the business he thought would be hardest… but wasn’t.

In this episode, you’ll learn:

• Why Jacob believes long-term rentals rarely deliver “real” cash flow (and what surprises most first-time landlords)
• How he chose a Midwest market before the data was obvious
• What underwriting looks like when you don’t have clean comps — and how to build guardrails anyway
• The behind-the-scenes reality of renovating and furnishing from across the country
• The launch lessons you only learn when guests are arriving tomorrow
• Why self-managing wasn’t nearly as hard as he expected
• How one deal can change your investing path faster than you think

If you’ve been stuck in analysis paralysis, this one is a reminder that you don’t need perfect certainty — you need the right protections, a real plan, and the willingness to get in the game.

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Episode Sponsored By:
STR Search

STR Search is the industry leading property finder service. They've helped investors acquire over 325+ profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com

This week’s Monday Market Data Report takes us to Miami, Florida, one of the most talked-about short-term rental markets in the country.

Is the hype justified? Mark breaks down the numbers by bedroom count to show where the real revenue gaps are—and why Miami rewards scale more than most markets.

Inside this episode:
• How 3-bedroom STRs range from average performers to nearly doubling revenue at the top
• Why 4-bedroom properties see a major revenue jump with only a slight dip in occupancy
• The eye-opening leap in performance for 5-bedroom homes, including six-figure potential
• What 6+ bedroom luxury properties are earning and why occupancy stays strong across all sizes
• The key takeaway: in Miami, bigger homes stay just as booked and earn significantly more

If you’re considering investing in South Florida or already own in Miami, this data-driven breakdown will help you understand where bedroom count, nightly rates, and performance truly intersect.

Tune in for the numbers, stay for the insights—and we’ll see you Friday for a new guest episode.