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Managing a short-term rental can feel overwhelming, especially with all the market myths out there. In this episode, John Bianchi joins Russ and Joey to break down why Airbnb is far from dead and how to strategically position your rentals for maximum profitability.John dives into what makes a property desirable, the importance of amenities, and how to create a “destination” experience that attracts guests year-round. We also cover key insights on the short-term rental tax loophole and strategies to maximize cash flow while staying compliant. Whether you're a beginner or a seasoned investor, this episode equips you with actionable steps to navigate the competitive STR landscape. Tune in now and learn how to make Airbnb work for you:Top three things you will learn: -How to identify profitable short-term rental markets-How to choose properties that stand out-How to leverage data to avoid costly mistakesAbout Our Guest:John Bianchi, also known as The Airbnb Data Guy, is a real estate investor who spends much of his time providing useful information on how to scrub data to find your next investment.In 2017, at just 24 years old, John sold a $10 million investment portfolio to start an Airbnb Arbitrage business. He quickly grew that to 15 cash-flowing properties in the Chicago area. By doing that, he developed processes to analyze Airbnb data and identify highly profitable properties anywhere. Since then, he's been teaching people these processes.Disclaimer: The opinions expressed on this podcast are solely those of the hosts and guests and do not constitute financial advice. Always consult a licensed professional for financial decisions.This episode is sponsored by a podcast show partner. We may receive compensation if you use links or services mentioned in this episode.The hosts may have a financial interest in the programs or services mentioned in this episode.Connect with John Bianchi:-Website - strsearch.com
The national housing correction is here but your results will be decided locally. Some markets are cooling gently, others are slipping fast, and a few affordable metros are still running warm. So where does that leave buy-and-hold, flips, STRs, and BRRRRs? We map the dramatic regional split, Midwest/Northeast steadier, Gulf Coast/Texas under pressure, and show how to match your strategy to on-the-ground realities like inventory, rent growth, and affordability. You'll hear why “flat prices + rising rents” can be a green light for cash flow, when to take a calculated swing in oversold-but-strong-fundamentals cities (think Austin/Nashville/Dallas), and where supply and insurance costs are pushing deeper discounts (hello, Florida). We also dig into metro-level forecasts into 2026 and why your underwriting should look different in Milwaukee than in Miami. In This Episode We Cover Local > national: why the same correction looks totally different by region and price tier Affordability & supply: the two signals driving winners and laggards (and how to measure both) Hottest vs. coolest markets: where buyers have leverage and where demand still pops Rents vs. prices: pairing flat/declining prices with rising rents to improve cash flow Risk-on vs. risk-off playbooks: conservative buy boxes vs. opportunistic dips in strong cities Flipping in a slowdown: wider spreads, longer days-on-market, how to price and pace Forecasts into 2026: what recent metro projections imply for your next 3 - 12 months of deals Hold or sell? Handling “paper losses,” market selection, and underwriting for a slower cycle Links from the Show Join the Future of Real Estate Investing with Fundrise Join BiggerPockets for FREE Find an Investor-Friendly Agent in Your Area Find Investor-Friendly Lenders Property Manager Finder Dave's BiggerPockets Profile Check out more resources from this show on BiggerPockets.com and https://www.biggerpockets.com/blog/on-the-market-369 Interested in learning more about today's sponsors or becoming a BiggerPockets partner yourself? Email advertise@biggerpockets.com. Learn more about your ad choices. Visit megaphone.fm/adchoices
What if your next short-term rental deal isn't failing because of the numbers… but because of your reviews?In this episode of Cash Flow Positive, Kenny Bedwell digs into the “curse” of review-driven real estate—how guest expectations, property condition, and first impressions can quietly make or break your returns. He breaks down the two sides of STR investing (real estate + hospitality), shares real-world examples from his own portfolio, and explains why operations and guest experience are just as critical as deal analysis.You'll learn what details guests really notice, how to find properties that support great reviews from day one, and the simple fixes that turn complaints into five-star ratings.If you want your short-term rental to outperform the market, hit play and start thinking like a guest, not just an investor.Timestamped Highlights[00:00] Why Kenny “hates” reviews 4and how they shape investor behavior[01:00] The two-headed monster of STR investing: real estate + hospitality[02:30] Why being a great host directly impacts revenue[04:00] How property age and updates influence guest satisfaction[06:00] Lessons from a historic 1860s home that became a five-star stay[09:00] The hidden cost of ignoring capital expenditures[10:40] When old systems (like HVAC) destroy the guest experience[12:00] How unfinished basements and outdated designs kill reviews[15:20] External factors: neighbors, privacy, roads, and power lines[20:00] Designing for privacy, accessibility, and comfort[23:00] How to impress guests from the moment they arrive[25:00] The power of small touches, like Kenny's ice cream bar idea[27:00] Why first impressions make or break your ratings[30:20] The link between five-star reviews and long-term revenueImportant LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) https://www.strinsights.com/top-investable-short-term-rental-markets-2025-reportInstagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights and Podcast Your Brand. Production and editing by Podcast Your Brand
How to Get Rich Quick with Real EstateIf you've been chasing the next “get rich quick” shortcut in real estate… this episode is your reality check.In this episode of Cash Flow Positive, Kenny Bedwell flips the script on fast money and exposes the truth about building real wealth through real estate. He shares insights from conversations with high-level investors: Those who buy $100M hotels and still play the long game and reveals why the biggest wins come from appreciation, tax strategy, and equity paydown, not just monthly cash flow.You'll learn the four true pillars of wealth in real estate, how to think like an investor instead of a speculator, and why repositioning your assets the right way can transform your portfolio faster than chasing short-term returns ever will.Stop looking for overnight success. Press play now to learn how the smartest investors actually get rich with patience, data, and a long-term plan.Timestamped Highlights[00:00] Back from the flu and fired up about “get rich quick” myths[01:30] The problem with chasing only cash flow[03:35] Lessons from top-tier investors who buy $100M properties[05:00] The four wealth pillars: cash flow, appreciation, tax savings, and equity paydown[07:00] What “repositioning” really means and why it's where wealth is built[09:25] When cash flow should be your priority and when it shouldn't[10:30] Why high-income professionals invest differently (and what that means for you)[12:30] How to calculate true ROI using total return, not just cash flow[15:20] The mindset shift: stop chasing income, start building net worth[18:30] Defining your investment goals before you buy your next STR[21:15] How Kenny evaluates deals now and why forced appreciation beats “good enough”Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) https://www.strinsights.com/top-investable-short-term-rental-markets-2025-reportInstagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights and Podcast Your Brand. Production and editing by Podcast Your Brand
In this episode, Taylor sits down with Katie, marketing leader at Furnish Finder, to unpack how midterm rentals have evolved far beyond the travel-nurse niche. Katie shares her journey from commercial real estate to leading growth at one of the fastest-growing platforms for 30+ day stays, and why MTRs are now a must-have strategy for short-term rental investors.In this episode:The expanding MTR guest base: from medical professionals to relocations, renovations, corporate travel, and insurance staysHow Furnish Finder grew into a powerhouse marketplace connecting hosts and tenants with no booking feesThe key operational differences between STRs and MTRs, and why MTRs can be a “breath of fresh air” for busy hostsWhat amenities actually matter for 30–90 day guests and how to stand outSimple ways to mix MTRs into your STR strategy to smooth cash flow and reduce turnoverIf you've ever wondered how to reduce turnover and still maximize income, this episode shows you how midterm rentals can simplify operations and keep revenue flowing year-round.
A DNA profile is a unique genetic fingerprint derived from an individual's DNA (deoxyribonucleic acid). DNA is the fundamental genetic material found in the cells of all living organisms, and it carries the instructions that determine our physical characteristics and biological traits.A DNA profile is created by analyzing specific regions of an individual's DNA known as short tandem repeats (STRs) or single nucleotide polymorphisms (SNPs). These regions exhibit variations between individuals, making them useful for identification purposes. DNA profiling involves extracting DNA from a biological sample, such as blood, saliva, hair, or semen, and then amplifying and analyzing the specific DNA regions of interest.Law enforcement agencies use DNA profiling in several ways:Criminal Investigations: When biological evidence is found at a crime scene, such as bloodstains or hair, DNA profiling can be performed to create a DNA profile from the sample. This profile can then be compared to profiles in DNA databases or against known suspects to identify or exclude potential perpetrators.Missing Persons and Unidentified Remains: DNA profiling plays a crucial role in identifying missing persons and unidentified remains. By comparing DNA profiles from unidentified remains to profiles of missing individuals or their relatives, law enforcement can establish familial relationships or make direct identifications.Cold Case Investigations: In cold cases, where the investigation has gone unresolved for an extended period, DNA profiling can be used to reexamine evidence and potentially link it to a known individual or identify new suspects.Forensic Intelligence: DNA profiles obtained from crime scenes can be stored in DNA databases, such as CODIS (Combined DNA Index System), which allows law enforcement agencies to compare profiles from different cases. This can help link previously unrelated crimes and provide leads for investigations.In this episode, we take a look at the new claims by Bryan Kohberger's legal team that 3 other unknown male DNA profiles were found at the crime scene and what it might mean moving forward.(commercial at 8:30)to contact me:bobbycapucci@protonmail.comsource:Bryan Kohberger claims DNA from three other men found at scene of Idaho murders | The IndependentBecome a supporter of this podcast: https://www.spreaker.com/podcast/the-moscow-murders-and-more--5852883/support.
What if scaling your vacation rental business could actually hurt your bottom line? This week, Jamie Lane sits down with Ashley Ching, founder and CEO of Inhaven, to unpack her research on why national hospitality management companies—from Vacasa to Ambridge—have repeatedly failed to scale successfully. Together, they dive into the structural challenges of the short-term rental industry and uncover why “bigger” doesn't always mean “better.”Ashley shares insights from hundreds of executive interviews across hotels, restaurants, and vacation rentals, revealing five key pillars that separate thriving, sustainable property managers from those that crumble under complexity. From the myth of economies of scale to the power of local operations and curated portfolios, this episode is a must-listen for any STR professional who wants to grow smarter—not just larger.Whether you manage 10 homes or 1,000, this conversation reframes how you think about profitability, service, and scale—and what true success in hospitality really looks like. You don't want to miss this episode.Key TakeawaysBigger isn't better: Hospitality is a labor-driven business, not a production line—growth often brings higher costs and lower margins.Curate your portfolio: The most successful managers focus on quality over quantity, offboarding “bad” properties that drain time and profit.Stay local: Empowering on-the-ground teams and decision-makers leads to stronger operations and better guest experiences.Choose owners wisely: Aligning with the right owners is as crucial as choosing the right homes.Pick your focus: You can prioritize service, scale, or profitability—but not all three at once. Sign up for AirDNA for FREE
In this episode, Jim brings on Tom Dunkel, founder of Eagle Capital Investments, co-founder of U.S. Mortgage Resolution (11k+ loans transacted), real-estate investor, and author of The Wealth Builders Playbook. Tom left the “corporate penitentiary,” got bloodied in '08, then built durable wealth across distressed mortgage debt, self-storage, STRs, and a fund-of-funds platform. They break down why “now” is always the right time if your horizon is long, how to own the paper when bricks are a pain, and how to evaluate deals with his SAFE method so you compound without blowing up. What You'll Learn Why headlines aren't a strategy: time horizon and cashflow beat “perfect timing” Distressed mortgage debt 101: how banks offload non-accrual loans—and how pros work them out The SAFE due-diligence method (Sponsor, Asset, Financials, Exit) you can apply to any alt deal Active vs passive: “who, not how” for busy owners who want diversification without a second job How tax advantages (depreciation, cost seg) and steady cashflow protect high earners Action Steps 1. Map Your Horizon & Cashflow Decide your hold period (5–10+ years) and set a monthly cashflow target that makes you work-optional. 2. Run SAFE on Your Next Deal Vet the Sponsor first, then Asset, Financials, and Exit. If any letter fails, pass and keep your powder dry. 3. Choose Your Lane Active: commit to learning, mistakes, and reps. Passive: piggyback a proven operator's network (fund-of-funds, co-GP) to diversify now.
Sief Khafagi didn't just build a business—he built a standard.In this episode, he reveals how leadership, culture, and vision turned TechVestor into one of the most respected brands in STR investing.• How leadership shapes the future of the STR industry• Building a culture that scales with integrity and precision• Setting new standards for quality and operations• Why great teams outperform any market cycle• The mindset shift every STR leader needs to make00:03:22 – The Real Problem: Bad Operators Drag the Industry Down00:07:40 – Leadership and Vision: Believing Before Anyone Else Does00:11:56 – Building High-Trust Teams That Scale00:15:38 – Culture Over Everything: The Real Competitive Advantage00:20:25 – Systems That Outlast the Founder00:25:44 – The Truth About Scaling: Leadership vs. Management00:30:57 – How TechVestor Blends Tech and Real Estate to Win00:35:46 – The Future of STR Leadership and Industry Standards00:40:38 – Legacy Leadership: Culture, Vision, and Setting the Bar HigherGuest Bio:Sief Khafagi is an ex-techie turned real estate investor who has helped thousands diversify into real estate. Today, he's the founder of Techvestor, one of the first institutional-grade and backed STR portfolios. With their vertically integrated advantages across acquisitions, renovation, design, management, and more, Techvestor is the leader in short-term rentals as an asset class. Backed by in-house technology, one of the deepest talent benches in the industry, and most recently, institutional backing, they're on a path to 500+ owned STRs over the coming years.Guest Link:https://www.linkedin.com/in/siefkhafagi/Get FREE Access to our Community and Weekly Trainings:https://group.strsecrets.com/
Sief Khafagi didn't just build a business—he built a standard.In this episode, he reveals how leadership, culture, and vision turned TechVestor into one of the most respected brands in STR investing.• How leadership shapes the future of the STR industry• Building a culture that scales with integrity and precision• Setting new standards for quality and operations• Why great teams outperform any market cycle• The mindset shift every STR leader needs to make00:03:22 – The Real Problem: Bad Operators Drag the Industry Down00:07:40 – Leadership and Vision: Believing Before Anyone Else Does00:11:56 – Building High-Trust Teams That Scale00:15:38 – Culture Over Everything: The Real Competitive Advantage00:20:25 – Systems That Outlast the Founder00:25:44 – The Truth About Scaling: Leadership vs. Management00:30:57 – How TechVestor Blends Tech and Real Estate to Win00:35:46 – The Future of STR Leadership and Industry Standards00:40:38 – Legacy Leadership: Culture, Vision, and Setting the Bar HigherGuest Bio:Sief Khafagi is an ex-techie turned real estate investor who has helped thousands diversify into real estate. Today, he's the founder of Techvestor, one of the first institutional-grade and backed STR portfolios. With their vertically integrated advantages across acquisitions, renovation, design, management, and more, Techvestor is the leader in short-term rentals as an asset class. Backed by in-house technology, one of the deepest talent benches in the industry, and most recently, institutional backing, they're on a path to 500+ owned STRs over the coming years.Guest Link:https://www.linkedin.com/in/siefkhafagi/Get FREE Access to our Community and Weekly Trainings:https://group.strsecrets.com/
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This week, Mark sits down with Rachel Allday, co-founder of Abode Luxury Rentals, managing nearly 200 high-end properties across Park City, Jackson Hole, and Sun Valley. Rachel shares how she and her husband built their company from scratch 18 years ago—long before Airbnb existed—and what “luxury” really means in today's short-term rental market.In this episode:How Rachel turned creativity into growth, from her first “wedding invite” mailer campaign to managing $10M+ estatesWhat defines luxury: authenticity, maintenance, high-touch service, and staff-to-property ratios that ensure perfectionWhy attention to detail wins: triple inspections, white linens, local touches, and hospitality that feels humanThe importance of team culture, shared accountability, and never settling for 95%How Abode achieves consistent five-star reviews through inspections, standards, and guest-first thinkingMarketing insights: why professional photography, consistent staging, and aspirational imagery matterVRMA's impact on her business growth, profitability, and network of mentors and peersRachel also opens up about her role on the VRMA Board of Directors, where she's helping shape the next generation of education and professionalism in the STR industry.Connect with Rachel: abodeluxuryrentals.comFollow Abode Luxury Rentals on InstagramCatch Rachel at VRMA International in Las Vegas___Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 265+ profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
Most investors look at bedroom counts at face value. Kenny Bedwell doesn't.In this episode of Cash Flow Positive, Kenny reveals a deal-finding strategy he's seen quietly pay off in competitive short-term rental markets: targeting properties with extra square footage and converting them into higher bedroom counts. From Sedona to the Poconos, Kenny explains why “heads in beds” is the #1 revenue driver, how to legally add bedrooms to force appreciation, and why average-performing STRs will always lose out to top properties.You'll hear how to spot these overlooked opportunities, the math that makes them work, and why moving quickly under contract is often the difference between landing a deal and watching it slip away.Don't settle for average returns. Press play now to learn how Kenny turns overlooked listings into high-cash-flow, high-appreciation wins.Important LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) https://www.strinsights.com/top-investable-short-term-rental-markets-2025-reportInstagram – @kenny_bedwellYouTube – Cash Flow PositiveLinkedIn – Kenneth BedwellCash Flow Positive is an original podcast hosted by Kenny Bedwell. Brought to you by STR Insights and Podcast Your Brand. Production and editing by Podcast Your Brand.
Would require permits, ban parties Philipstown's Town Board received draft regulations on Thursday (Oct. 2) for short-term rentals such as Airbnb and Vrbo that require annual permits, along with a ban on parties, limits on stays and requirements for off-site parking. Judy Farrell, a member of the Town Board and of the Short-Term Rental Committee it created to come up with a code governing STRs, said during the board's meeting that the group reviewed guidelines from Cold Spring and other towns but crafted regulations "specific to Philipstown." Their goals, according to the draft of a local law amending the town code, included ensuring that STRs meet fire and safety standards and avoid harming neighbors with nuisances such as noise and trash, while allowing property owners to earn income from their rentals. "It does ensure that there are safe places for people, for tourists, to stay," said Farrell who, along with the rest of the board, scheduled a workshop for Oct. 29. As drafted, the rules establish five categories of STRs, whose owners must apply annually for permits: (1) rentals in which the owner remains on the property, (2) unhosted rentals, (3) one-time rentals for up to 14 consecutive nights once a year, (4) second homes and (5) tourist homes owned by corporations. Those STRs would be confined to three zoning districts: R-1 and I-1, where owners must provide on-site parking or a designated parking area, and the B-1 district. Except for one-time lodgings, stays would be set at between two and 29 consecutive nights. Unhosted lodgings would be limited to 90 nights a year and prohibit parties and "other gatherings or events." Owners with buildings having more than one residence could only rent one as an STR but would be allowed to rent accessory buildings. They would also have to carry at least $500,000 in liability insurance and pass an annual code-enforcement inspection. Fines for violating the regulations would be $1,000 for the first offense; $2,000 for the second, with forfeiture of the permit for the remainder of the year; and $3,000 for the third, with a four-year ban on an STR permit. In other business… The board voted to extend for another six months a moratorium on the approval of oil tanks holding more than 10,000 gallons. Town attorney Stephen Gaba said newly drafted regulations governing tanks should be ready for review next month. With Gaba retiring at the end of the year, the board approved a resolution to solicit bids for the town and the Planning Board, which he also advises. The town hoped to find a replacement from Gaba's firm, Drake Loeb, "but that is not working out," said Van Tassel. Retaining the firm for the Planning Board means "moving their meeting to a different night," he said. "I have spoken with [Planning Board Chair] Neil Zuckerman about it. He's polling his board to make sure that they're OK with it." The board approved an agreement to provide ice and snow removal to Nelsonville for the upcoming winter. Van Tassel said the village received bids for road maintenance whose prices "they could not cover." The board approved a permit for a film company called Doc in a Box Corp. to shoot at the Manitou School on Route 9D. Filming will take place on Oct. 10 for a project titled Best Medicine. According to IMDB, there is an upcoming Netflix series by that name in which "a brilliant surgeon leaves Boston to become a small-town doctor where he spent childhood summers. Despite his medical skills, his rude manner alienates locals as he battles hidden phobias and struggles with personal connections."
MY NEWSLETTER - https://nikolas-newsletter-241a64.beehiiv.com/subscribeJoin me, Nik (https://x.com/CoFoundersNik), as I interview Taylor Jones (https://x.com/MrJonesSTRs), the founder of strsearch.com.Have you ever wondered if short-term rentals (STRs) are as passive as they seem? I used to think so, but Taylor completely changed my perspective. He breaks down how he went from a sales guy to overseeing over $120 million in STR investments by treating it not as a real estate game, but as an operations business.We dive into his first investment—a cabin in the North Georgia mountains that he bought having never owned real estate before—and how it generated $22,000 in cash flow its first year.Taylor reveals the critical mistakes he made, the lessons he learned about market supply and demand, and how a single amenity like a pickleball court can add $40,000 to your annual revenue.We also get into the incredible tax benefits and how STRs can offer active losses to offset your regular income, something I wish I'd known sooner.Questions This Episode Answers:• How can a single pickleball court add over $40,000 in annual revenue to an Airbnb?• Why is a short-term rental business more about operations than real estate?• How can you use short-term rentals to legally reduce your taxable income?• What is the biggest mistake new STR investors make when choosing a property?• Why are large-group rentals and small, romantic getaways the hottest trends right now?Enjoy the conversation!__________________________Love it or hate it, I'd love your feedback.Please fill out this brief survey with your opinion or email me at nik@cofounders.com with your thoughts.__________________________MY NEWSLETTER: https://nikolas-newsletter-241a64.beehiiv.com/subscribeSpotify: https://tinyurl.com/5avyu98yApple: https://tinyurl.com/bdxbr284YouTube: https://tinyurl.com/nikonomicsYT__________________________This week we covered:00:00 The Allure of Short-Term Rentals02:55 Understanding the Operations Behind STRs05:42 The Journey into Real Estate Investment09:00 Lessons from Early Investments12:09 Scaling Up: From One to Multiple Properties14:56 Market Dynamics and Supply-Demand Imbalances18:11 Navigating the Real Estate Landscape20:55 Investment Strategies for Success26:00 Understanding Market Dynamics and Profitability30:13 Revenue Estimation and Occupancy Rates33:25 Tax Implications and Depreciation Strategies40:27 Investment Strategies for Short-Term Rentals47:31 Advice for New Investors in Short-Term Rentals
Four years, 250 episodes, listeners in 60 countries. Annie Holcombe of the “Alex & Annie” podcast shares how a scrappy launch at VRMA turned into one of the most influential shows in short-term rentals. We cover booking hard-to-get guests, the value of cross-pollinating hotel best practices, and the power of sticking with it. Annie also announces her new consultancy, Annie & Co, and her election to the VRMA Board, with a focus on education and member value.In this episode:How a consistent weekly cadence built momentum and a global audienceGuest strategy that goes beyond operations to branding, tech origin stories, and women leadersLessons STRs can borrow from hotels to level up guest experience and revenueWhy education is the industry's biggest gap and how VRMA can meet itAnnie's leap to consulting: who she helps, first 25 to 50 units, and channel diversification that actually worksSneak peek at VRMA Vegas: more interactive sessions, better engagement, and community vibeConnect with Annie:Website: anniecosolutions.comEmail: annie@anniecosolutions.comEpisode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 265+ profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
Is refinancing your short-term rental a smart move—or a trap that eats away your cash flow?In this episode of Cash Flow Positive, Kenny Bedwell sits down with veteran mortgage broker and STR financing expert Matt Stout. With over 32 years of lending experience and thousands of deals funded, Matt pulls back the curtain on when refinancing actually makes sense. From dropping interest rates and shifting housing trends to creative ways to redeploy “dead equity” into higher cash-flowing properties, this episode delivers the unvarnished truth about refinancing in today's market.You'll learn the right (and wrong) reasons to refinance, how to weigh costs versus cash flow, and why keeping versus selling a property can make or break your long-term wealth.Don't guess your way through one of the biggest financial decisions you'll face as an investor. Press play now to get Kenny and Matt's proven framework for knowing when to refinance and how to use it to build real generational wealth.About the GuestMatt Stout is “The STR Loan Guy” and founder of Consumers Financial, a mortgage brokerage licensed in 48 states. With over three decades in lending and a personal background in real estate investing, Matt specializes in STR and DSCR loans that help investors unlock equity and scale their portfolios. He's known for creative lending strategies, hybrid loan solutions, and his straight-shooting approach to helping investors win deals.
This week I got to speak with Erin Dalton-Cooney, the Head of Property Management Design at Wayfair Professional. Erin is a wealth of knowledge in this industry, and in her role she's gained experience overseeing design and set up for every type of property from STRs, MTRs, boutique hotels, and unique resorts. She shares with us today how Wayfair Professional is the secret weapon that designers are using to take shipping consolidation and install completely off their plates. If the pro designers trust Wayfair Professional, you should too! Erin teases us with what's coming next for Wayfair Professional, what they have to help you now, and how they are saving hosts serious time and money, so you can get back to what you do best – investing! Check out mine and Tatianna Taylor-Tait's official Wayfair Tastemaker collection HERE Connect with @wayfairproffesional on Instagram Thank you to my sponsors! Lodgify - Link Receive 20% off Lodgify's most powerful plans with code NoVacancy20 at checkout Proper - Link Visit the link to claim your free risk assessment with Proper. Learn more about your ad choices. Visit megaphone.fm/adchoices
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Pedro returns to unpack Sunny AI, a purpose-built assistant trained on Summer OS's proprietary data to help investors and operators spot patterns, compare markets, and forecast performance in seconds.In this episode:Why AI fits STRs: fragmented data, shifting markets, and the need for predictive modelingWhat makes Sunny AI different: specialized (not generic) AI trained on Summer OS data to “think” like an operator and investorHow it works: compare cities and submarkets, build comp sets, benchmark a specific home, and translate complex metrics into plain EnglishUse cases for everyone: first-time buyers to 1,000-unit PMs (hours of analysis reduced to minutes)The future: AI for STRs becomes as standard as MLS or Zillow for real estate and GPS for driving___Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 265+ profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
From the cockpit to commercial real estate, Tate's story shows how a high-earning W-2 professional can build wealth outside of the stock market. In this episode of the Tax Smart REI Podcast, Tate shares the lessons he learned moving from single-family to multifamily to syndications and the strategies that help pilots and other professionals put their money to work more effectively. You'll learn: - How Tate's early mistakes shaped his investing philosophy - Why LPs should evaluate sponsors before the deal - Where commercial real estate sits in today's cycle - How oil & gas and STRs can reduce taxes for W-2 earners - Why access to alternatives in retirement accounts could be a game-changer To become a client, request a consultation from Hall CPA, PLLC at go.therealestatecpa.com/3KSEev6 Subscribe to REI Daily & Enter to Win a FREE Strategy Call: go.therealestatecpa.com/41JuQBX Connect with Eckard Enterprises: eckardenterprises.com/taxsmartrei/ More From Tait: Website: https://www.turbinecap.com Co-authored Oil and Gas eBook: https://drive.google.com/file/d/17jUYSuoJGCU2ea4SN6MLgazmp-3LE2Lt/view?usp=share_link Daniel Rusteen's Airbnb book: https://www.amazon.com/Optimize-Your-Airbnb-audiobook/dp/B07R7CCKPK/ref=sr_1_1?dib=eyJ2IjoiMSJ9.RuqABHwSbg5DlqM7IpdbdyWEN0kpPfMH9Zirre2T_2LGjHj071QN20LucGBJIEps.Twgy40bFLaRKl4w4yOQGk7aOq7kWbEn890lz81_OJDU&dib_tag=se&hvadid=693594071991&hvdev=c&hvexpln=67&hvlocphy=1027744&hvnetw=g&hvocijid=18402973686594528136--&hvqmt=e&hvrand=18402973686594528136&hvtargid=kwd-2430861329715&hydadcr=21936_13365930&keywords=optimize+your+bnb+by+daniel+rusteen&mcid=e22c221c33dd3f379af9461f5fcc2624&qid=1757789681&sr=8-1 The Tax Smart Real Estate Investors podcast is for general information purposes only and is not intended to provide, and should not be relied on for, tax, legal, or accounting advice. Information on the podcast may not constitute the most up-to-date legal or other information. No reader, user, or listener of this podcast should act or refrain from acting on the basis of information on this podcast without first seeking legal and tax advice from counsel in the relevant jurisdiction. Only your individual attorney and tax advisor can provide assurances that the information contained herein – and your interpretation of it – is applicable or appropriate to your particular situation. Use of, and access to, this podcast or any of the links or resources contained or mentioned within the podcast show and show notes do not create a relationship between the reader, user, or listener and podcast hosts, contributors, or guests. Any mention of third-party vendors, products, or services does not constitute an endorsement or recommendation. You should conduct your own due diligence before engaging with any vendor.
In this episode of the Real Estate Education Podcast, Erin Spradlin and James Carlson dive into a critical warning for real estate investors: AI is dangerously unreliable for investment advice. James shares his experiment testing ChatGPT's Colorado Airbnb market knowledge, revealing that over 50% of recommendations were completely illegal—including cities that banned STRs entirely.
If $250,000 dropped into your lap today, would you actually know what to do with it?In this episode of Cash Flow Positive, Kenny Bedwell pulls back the curtain on exactly how he'd put that money to work in short-term rentals. He breaks down why your financing strategy can make or break a deal, the five cost buckets most investors forget about, and why setting your ROI goal up front is non-negotiable.You'll hear Kenny think through real markets, from Florida beaches to Shenandoah cabins, and explain how to spot which ones fit your budget and which ones will bleed you dry.Don't guess your way into a $250K mistake. Hit play now to hear Kenny's no-fluff, data-backed roadmap and get clarity on where your money will actually cash flow.Timestamped Highlights[00:00] How a $250K windfall changes your investing strategy overnight[02:14] The financing trap that torpedoes deals before they close[04:18] The five hidden costs every STR investor must budget for[07:36] Kenny's minimum ROI goals—and why cash flow beats percentages[10:53] The “process of elimination” method for picking your markets[14:25] Why Bradenton, FL, might work—and the brutal barrier to entry[21:00] Shenandoah's low-barrier charm vs. beach market competition[24:38] How lakefronts in Michigan and urban rentals in Cincinnati stack upResourcesSTR Insights softwareTop Markets Report (via STR Insights website)Dave Ramsey podcast (benchmark reference)Zillow & Redfin (for market comps)Evergreen LinksWant us to find the deals for you? https://strinsights.com Get Top Markers for STRs (2025) https://www.strinsights.com/top-investable-short-term-rental-markets-2025-report
Welcome to Hassle-Free RE! Today, Dave Menapace and Will Van Wickler break down what it really takes to scale beyond 10 properties in the short-term rental business. From hidden costs to operational complexity, they reveal the challenges no one talks about and the mindset shifts required to build a sustainable, profitable business.Dave and Will discuss why scaling isn't just about acquiring more doors—it's about building systems, hiring the right team, and stepping into the CEO role. They share stories from managing dozens of properties and a boutique hotel, highlighting the importance of financial organization, operations across different markets, and learning to coach your team instead of trying to do it all yourself.This episode also explores the personal side of scaling—how to manage the mental load, avoid burnout, and focus on the few things that actually move the needle. Whether you're just getting started or looking to expand your portfolio, this conversation will help you prepare for the realities of growth and avoid costly mistakes. Tune in now to gain the insights you need to scale with confidence and clarity.TIMESTAMPS1:22 – Scaling beyond 10 properties and the myth of “easy scaling”2:23 – The hidden costs of growth3:09 – The foundation for scaling3:59 – Beach vs. mountain STRs and diversifying across markets4:59 – Managing 40+ properties and shifting into the CEO mindset6:00 – Building a team before you think you can afford it7:56 – Lessons in leadership: coaching, mentoring, and emotional intelligence8:57 – Obsessions that drive business growth: owners, teams, and guests10:00 – Breaking the “grind first, hire later” mindset10:38 – The importance of roadmaps, reps, and purposeful scaling12:00 – Hyperfocus on 1–3 strategies to 10x faster13:14 – Final takeaways: team, mindset, and staying disciplined with growth#ShortTermRentals #BusinessGrowth #RealEstateInvesting #ScalingSTRs #PropertyManagement
Andy Newman shares how a backpacker's curiosity turned into a 140-property, multi-state operation - and why the true moat isn't software, it's a team with years of lived hospitality “stories” you'll never find in a manual. We dig into hiring for heart and skill, right-sizing tech, and building resilient portfolios that survive seasonality, HOAs, and hurricanes.What you'll learnWhy tenure matters: the power of a team averaging 5+ years of on-the-ground scenariosThe tech trap: streamline tools, keep the robust PMS, avoid shiny-object overloadHiring that sticks: HR-led recruiting, multi-interviewer veto power, and benefits that retain A-players (PTO, sick days, parental leave, 4-day weeks for top performers)Culture > shortcuts: why “VAs run it while you sip drinks on a beach” is a mythRisk-smart growth: diversify by seasonality, regulation, and climate (Andy's 50-mile & ~1500-mile rules)Owner advisory: treat STRs like a portfolio—location, amenities, and booking windows tailored to returnsThe road ahead: professional management and selection matter as the industry enters its “third inning”Connect with Andy: andy@newmanhospitality.comNewman Hospitality: newmanhospitality.comNew interviews every Friday + the Monday Market Report!____Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 255 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
Is moving from short-term rentals into boutique hotels the natural next step for savvy investors? In this episode, Jamie Lane sits down with James Savier, SVP at CBRE Hotels, to explore why more STR operators are eyeing boutique hotel ownership—and what it really takes to succeed.Hotels may seem like an entirely different ballgame, but as James explains, the leap isn't as far as you might think. From financing options and valuation differences to building brands that actually command loyalty, this conversation demystifies how STR experience can translate into hotel investment. You'll also hear candid insights on common mistakes, hidden opportunities, and why timing matters more than ever in today's market.If you've ever wondered whether boutique hotels could be your next big play, this episode will open your eyes. You don't want to miss it!What You'll Learn in This Episode:Why many STR investors see boutique hotels as the next logical step.How hotels are valued differently from rental portfolios—and why that matters for your exit strategy.The financing tools available for hotel buyers (and how they compare to STR loans).The role of branding, guest experience, and scale in boutique hotel success.Common pitfalls first-time hotel investors make—and how to avoid them.Sign up for AirDNA for FREE
Investor Fuel Real Estate Investing Mastermind - Audio Version
In this episode of the Real Estate Pro Show, host Erika interviews Corey Mays, a rising star in the real estate investing and capital space. Corey shares his journey into real estate, starting from wholesaling to multifamily acquisitions, and discusses the importance of networking and building relationships in the industry. He also reflects on valuable lessons learned from early deals and outlines his current business ventures and future plans. Professional Real Estate Investors - How we can help you: Investor Fuel Mastermind: Learn more about the Investor Fuel Mastermind, including 100% deal financing, massive discounts from vendors and sponsors you're already using, our world class community of over 150 members, and SO much more here: http://www.investorfuel.com/apply Investor Machine Marketing Partnership: Are you looking for consistent, high quality lead generation? Investor Machine is America's #1 lead generation service professional investors. Investor Machine provides true ‘white glove' support to help you build the perfect marketing plan, then we'll execute it for you…talking and working together on an ongoing basis to help you hit YOUR goals! Learn more here: http://www.investormachine.com Coaching with Mike Hambright: Interested in 1 on 1 coaching with Mike Hambright? Mike coaches entrepreneurs looking to level up, build coaching or service based businesses (Mike runs multiple 7 and 8 figure a year businesses), building a coaching program and more. Learn more here: https://investorfuel.com/coachingwithmike Attend a Vacation/Mastermind Retreat with Mike Hambright: Interested in joining a “mini-mastermind” with Mike and his private clients on an upcoming “Retreat”, either at locations like Cabo San Lucas, Napa, Park City ski trip, Yellowstone, or even at Mike's East Texas “Big H Ranch”? Learn more here: http://www.investorfuel.com/retreat Property Insurance: Join the largest and most investor friendly property insurance provider in 2 minutes. Free to join, and insure all your flips and rentals within minutes! There is NO easier insurance provider on the planet (turn insurance on or off in 1 minute without talking to anyone!), and there's no 15-30% agent mark up through this platform! Register here: https://myinvestorinsurance.com/ New Real Estate Investors - How we can work together: Investor Fuel Club (Coaching and Deal Partner Community): Looking to kickstart your real estate investing career? Join our one of a kind Coaching Community, Investor Fuel Club, where you'll get trained by some of the best real estate investors in America, and partner with them on deals! You don't need $ for deals…we'll partner with you and hold your hand along the way! Learn More here: http://www.investorfuel.com/club —--------------------
Welcome to our latest episode! Today, Dave Menapace and Will Van Wickler tackle one of the most pressing issues in real estate and hospitality—the growing wave of short-term rental regulations. From Boston and Portland to vacation markets like Cape Cod and Bar Harbor, they break down how local governments are shaping the landscape and what it means for investors, operators, and homeowners.Dave and Will explore whether regulations are killing innovation or simply protecting neighborhoods. They highlight the differences between metropolitan markets, where affordability and neighborhood impact are driving restrictions, and vacation markets, where safety and infrastructure are the focus. The conversation also dives into the opportunities these changes create—such as boutique hotels, ADUs, and other creative strategies that thrive within regulatory frameworks.Whether you're considering your first investment property or already operating multiple units, this episode delivers essential insights on zoning, HOA rules, due diligence, and the importance of common sense in real estate investing. Tune in now to learn how to navigate regulation with confidence, spot hidden opportunities, and avoid costly mistakes.TIMESTAMPS01:57 – Why regulation isn't always a bad thing02:58 – Metro and vacation markets03:53 – How regulations shape neighborhoods05:41 – Boutique hotels create opportunities where STRs are restricted07:14 – Creative approaches with ADUs and owner-occupied rentals08:47 – HOAs: hidden rules that can make or break your investment10:37 – Due diligence and using common sense before buying11:40 – Why relationships and neighbor dynamics matter for operators12:43 – Deal analysis, and avoiding bad buys13:53 – Why AI tools fall short on regulation research14:43 – How to connect with Dave and Will#ShortTermRentals #RealEstateInvesting #STRRegulations #BoutiqueHotels #PropertyManagement
Taylor sits down with Alex, co-founder of Whimstay - the OTA built to fill your unsold gap nights inside 30 days. Alex shares his journey from theater to Yelp to startup life, why Whimstay is “HotelTonight for STRs,” and how hosts can add revenue without stealing a single booking from Airbnb or Vrbo.In this episode:Incremental revenue, not cannibalization: Why Whimstay targets 0–30 days to capture mid-week, shoulder-season, and last-minute demand.Host economics: 5% host commission + traveler fee (≈5–7%); you set a last-minute discount and keep bookings from going to zero.Supply → demand flywheel: Early focus on PMS integrations (Guesty, Escapia, Streamline, etc.) and larger PMs; now expanding with an independent host portal.Who books last-minute: Gen Z/Millennial “next-gen” travelers, digital nomads, and retirees seeking value and spontaneity.Distribution strategy reality check: Don't “work for one OTA.” Diversify to reach different booking windows and traveler segments.Growth levers: Google Vacation Rentals partnership, organic community buzz, and a ramped marketing push.Vision: Make last-minute STRs ubiquitous - hosts list on Airbnb/Vrbo and Whimstay to clear expiring inventory.If you've got unbooked Tuesdays or shoulder-season gaps, this convo will show you how to turn them into found money - no new cleaners, no new systems, just smarter distribution.Explore Whimstay: whimstay.comNew episodes every Friday + Monday Market Report___Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 215 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
Welcome to our latest episode! Today, Dave Menapace and Will Van Wickler dive into one of the hottest debates in hospitality—Airbnb versus boutique hotels. With firsthand experience managing both luxury vacation rentals and boutique hotels across New England, they unpack the shifts in traveler behavior, the challenges of guest expectations, and the long-term opportunities for investors.Dave and Will explore whether Airbnbs are truly “collapsing” or if the market is simply evolving. They discuss why boutique hotels are gaining momentum, how guest expectations around cleanliness and consistency are shaping decisions, and the economic pressures impacting both industries. Dave shares insights from managing boutique hotels at scale, while Will highlights the differences in condition standards, branding power, and commercial financing for multi-unit hospitality properties.Whether you're a real estate investor, property manager, or just curious about where short-term rentals are headed, this episode breaks down the pros and cons of both asset classes. Tune in now to learn what travelers value most, why consistency is becoming the key competitive edge, and how to think strategically about hospitality investments moving forward. TIMESTAMPS02:05 – Airbnbs versus boutique hotels: is there really a collapse?03:32 – Shifts in the market and vacation spending trends05:35 – Economic slowdown and what service businesses reveal about the economy06:37 – Why boutique hotels feel safer and more consistent08:18 – Airbnb condition challenges vs. hotel cleanliness standards10:01 – The five-star review pressure for STR hosts versus hotel reputation models11:56 – Boutique hotels versus single-family STRs13:37 – Scale advantages15:29 – Investment considerations: residential STRs vs. boutique hotels16:01 – Commercial financing, seller credits, and due diligence for hotel deals17:23 – Why relationships matter in commercial hospitality investing18:21 – Wrap-up, takeaways, and how to connect with Dave and Will#ShortTermRentals #HospitalityIndustry #AirbnbVsHotels #RealEstateInvesting #BoutiqueHotels
This week on the STR Investing Podcast, Mark sits down with Valerie Gangas, CEO of Juniper Holiday + Home, author, meditator, and lifelong hospitality pro. Valerie shares how a childhood split between Chicago restaurants and apartment buildings shaped her “guests-first” operating system, why there's never a checkout chore list, and how sending a real human (often with a pie!) can turn hiccups into five-star moments. She also opens up about boundaries, meditation, and why taking care of yourself is the first step to taking care of your team, owners, and guests.In this episode:Valerie's origin story: restaurants + multifamily → boutique STR managementDesigning for memories (fresh flowers, cookies, wine, pet-name biscuits) vs. overspending on marbleThe Juniper standard: effortless check-in, zero checkout tasks, and mid-stay service that wowsHiring & scaling: trusting your gut, team consensus, and filling your own gapsMindset for operators: meditation, boundaries, and leading from a calm centerOTAs vs direct: grateful for discovery, intentional about repeat bookingsThe education gap in STRs and why community knowledge-sharing matters____Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 255 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
Are you running a successful Airbnb or short-term rental business… but feeling the burnout from endless turnovers, guest messaging, and unpredictable income? You're not alone. In this episode, we sit down with the founders of Thanks for Visiting, Sarah Karakaian & Annette Grant, who are seasoned STR operators and educators. We talk about how they've integrated mid-term rentals (MTRs) into their business strategy. We cover:Why experienced STR hosts are adding MTRsHow hybrid hosting stabilizes revenue and reduces stressThe systems and mindset shifts that make furnished rentals sustainableTips for maximizing profit while avoiding host burnoutIf you're serious about building a smarter, more profitable hosting business, this conversation will change the way you think about STRs and MTRs. Subscribe for more insights from top operators.Ready to fill your mid-term rental? List your property on Furnished Finder today:https://www.furnishedfinder.com/list-your-property(Use code LLD10 for $10 off new listings)Learn more about Thanks for Visiting and their upcoming bootcamp: https://thanksforvisiting.com/bootcamp⏱️ Episode Timestamps:0:00 Welcome to The Landlord Diaries2:25 How Sarah and Annette met and built TFV4:20 What made two STR pros explore MTRs6:40 Why STR burnout is real and what to do about it8:40 Resourcefulness is your #1 business tool9:35 Real-life STR/MTR hybrid strategy success stories11:35 Pro tip: Give yourself time to find the right MTR guest13:00 When midterm makes more sense than short term15:05 How they were already MTR-ready without knowing it17:00 Can glamping work for monthly stays?18:00 Matching property type to market demand19:50 When a property doesn't work for MTR23:40 Why MTRs are perfect for winter slowdowns25:45 Listing Audit Bootcamp sneak peek29:35 How to price midterm rentals effectively33:20 Where Furnished Finder fits in a hybrid strategy35:50 How MTRs helped reduce burnout and increase freedom38:25 Smart calendar management for STR/MTR combos40:15 No booking fees and full control with Furnished Finder41:10 Why MTRs are part of the future of furnished rentals42:45 Most unique midterm guest stories45:20 Best business advice for scaling without burnoutTrending Midterm Rental Resources:https://www.furnishedfinder.com/Resources/PMResources The Landlord Diaries is brought to you by Furnished Finder, where you can list your property for one low price and pay zero booking fees.
In this episode of STR Like the Best, I sit down with John from Topkey—a financial operating system built specifically for property managers—to talk about the “unsexy” but absolutely essential side of running a short-term rental business: cash flow, expense tracking, and financial controls.We cover why cash (not revenue) is the single source of truth in your business, how to capture every reimbursable dollar without adding admin headaches, and how to keep your favorite rewards credit cards in play while still integrating all your spend into one clean system.John shares his journey from investment banking to Starwood Hotels, HotelTonight, and Airbnb, and how those experiences shaped Topkey's mission to simplify the messy financial workflows in STRs. We also swap stories on leaving banking, building businesses with our spouses, and why the why behind your business matters just as much as the tools you use.Whether you're managing 5 units or 50, this episode will show you how to run tighter books, free up headspace, and ultimately build a business that supports the life you want.LEARN MY STR INVESTING & STRATEGIES
In this episode, Taylor sits down with Zach Busekrus, growth marketer and co-founder of Journey, a game-changing loyalty platform designed for STR operators and independent boutique hotels. Zach shares how his winding path from higher ed marketing and podcasting to nomadic Airbnb living during COVID ultimately led to Journey: a mission-driven platform curating “stays with soul” and giving operators a powerful new way to increase repeat bookings, monetize guest loyalty, and gather data, all without giving 15–30% to the OTAs.You'll learn:How Zach turned a side project newsletter into a startup acquisitionThe behind-the-scenes story of Journey's creation and its big-name backersWhy loyalty programs work and why most independent hosts haven't had access to themHow Journey helps guests earn and redeem points across a curated network of high-quality staysWhy operators benefit from better guest insights, brand credibility, and additional revenue streamsWhat it really takes to get early adopter traction in the hospitality spaceJourney's vision for becoming the “soulful” alternative to chain hotel loyalty systemsWhether you're managing four vacation rentals in Joshua Tree or scaling a boutique hospitality brand, this episode is packed with strategic insights on how to turn direct bookings and guest loyalty into real growth, without relying solely on Instagram or the OTAs.Apply to the Journey Alliance: alliance.journey.comDownload the app or learn more at: journey.comContact Zach: zach@journey.com Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 255 profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
#560 Thinking about investing in an Airbnb but not sure how to know if it's a good deal? In this episode, host Brien Gearin sits down with John Bianchi — founder of STR Search and widely known as “The Airbnb Data Guy.” John shares how he went from financial advisor to short-term rental data expert, helping investors avoid costly mistakes and identify profitable properties using deep data analysis. You'll learn what really makes an Airbnb stand out, how to evaluate markets, the truth about today's STR landscape, and why understanding your numbers is more crucial than ever! What we discuss with John: + How John became “The Airbnb Data Guy” + Transition from financial advisor to STR expert + Why most people buy the wrong Airbnb properties + How STR Search helps investors with data + Common Airbnb revenue-driving features + Importance of pricing strategy and revenue managers + Why many STRs fail — and how to avoid it + Airbnb market conditions in 2025 + The truth behind the “Airbnb bust” narrative + How to use STRs for tax savings and cash flow Thank you, John! Check out STR Search at STRSearch.com. Follow John on Instagram and YouTube. Watch the video podcast of this episode! To get access to our FREE Business Training course go to MillionaireUniversity.com/training. And follow us on: Instagram Facebook Tik Tok Youtube Twitter To get exclusive offers mentioned in this episode and to support the show, visit millionaireuniversity.com/sponsors. Want to hear from more incredible entrepreneurs? Check out all of our interviews here! Learn more about your ad choices. Visit megaphone.fm/adchoices
Short-term rentals (or STRs) like Airbnbs have been a hot topic in the local headlines over the last few years. We talked with two STR owners back in 2023 when they first challenged the County's regulations, but since then, they've taken the County to court, including hearings in front of the Nevada Supreme Court. So where does it all stand now? Are STRs legal in Clark County, and what kinds of regulations would actually make sense for our neighborhoods? Co-hosts Sarah Lohman and Dayvid Figler discuss. Please see below for tomorrow's sponsor show notes: Learn more about the sponsors of this August 25th episode: Woven Want to get in touch? Follow us @CityCastVegas on Instagram, or email us at lasvegas@citycast.fm. You can also call or text us at 702-514-0719. For more Las Vegas news, make sure to sign up for our morning newsletter, Hey Las Vegas. Learn more about becoming a City Cast Las Vegas Neighbor at membership.citycast.fm. Looking to advertise on City Cast Las Vegas? Check out our options for podcast and newsletter ads at citycast.fm/advertise.
What if you could turn everyday travelers into a social media content army - one that boosts your visibility, drives direct bookings, and promotes the local experiences your guests already ask about?In this episode, Mark sits down with Maddie Rifkin, founder & CEO of Mount, to unpack how she's helping short-term rental operators, property managers, and even mom-and-pop vendors monetize recommendations and go viral without relying on big-budget influencers or OTAs.They dive into:How Mount connects hosts with local vendors & turns recs into revenueWhy normal travelers often outperform big influencers in content creationWhat it takes to launch your own “content army” and build massive brand awarenessThe truth about follower count vs. post performanceHow one host added $200K in direct bookings with a single viral strategyThe best platforms to focus on for real ROI in the STR spaceHow to prepare for a viral spike so it doesn't fizzle outPlus: Maddie reveals what makes a great content creator, how her team trains and deploys stewards across the country, and why now is the best time to build your brand on social media before it's too late.If you're tired of the OTA hamster wheel and want to future-proof your business with better guest experiences, content marketing, and direct booking strategies, this episode is your jump start.Connect with Maddie: LinkedIn Learn more about Mount: www.mountlocks.com___Episode Sponsored By:STR SearchSTR Search is the industry leading property finder service. They've helped investors acquire over 255 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, we're joined by Erin Lenhardt of The Brighthouse to talk building, market focus, design of winning STRs, guest experience, investing and a LOT more...Enjoy!⭐️ Links & Show NotesAdam NorkoConrad O'ConnellThe BrighthouseErin Lenhardt
Think buying a short-term rental is the fast track to homeownership? In this episode, David Sidoni unpacks the real math behind Airbnb investing — and why it might be the wrong move if you're still renting.With affordability at an all-time low, many first-time homebuyers are exploring creative ways to get into real estate. One trend gaining popularity: buying a short-term rental like an Airbnb in a cheaper market instead of purchasing a primary residence. But in this brutally honest episode, David Sidoni reveals why that plan could backfire.David breaks down the 2025 short-term rental landscape, explaining how increased competition, regulations, and declining profits have changed the game. More importantly, he highlights the financial risks renters take when they try to become investors before becoming homeowners.This episode dives into the math, the mindset, and the myths — showing you why owning your own home first is the smartest play. If you're tempted by Airbnb hype, you need to hear this before making a costly mistake.Quote: "The golden goose of Airbnb is losing its feathers and turning into a turkey super quick."Highlights:Why short-term rental investing isn't what it used to be in 2025The financial danger of skipping rent replacementHow tax laws, maintenance, and financing make STRs riskier than they lookA breakdown of real costs vs. projected incomeWhat first-time buyers should do instead of chasing Airbnb profitsConnect with me to find a trusted realtor in your area or to answer your burning questions!Subscribe to our YouTube Channel @HowToBuyaHomeInstagram @HowtoBuyAHomePodcastTik Tok @HowToBuyAHomeVisit our Resource Center to "Ask David" AND get your FREE Home Buying Starter Kit!David Sidoni, the "How to Buy a Home Guy," is a seasoned real estate professional and consumer advocate with two decades of experience helping first-time homebuyers navigate the real estate market. His podcast, "How to Buy a Home," is a trusted resource for anyone looking to buy their first home. It offers expert advice, actionable tips, and inspiring stories from real first-time homebuyers. With a focus on making the home-buying process accessible and understandable, David breaks down complex topics into easy-to-follow steps, covering everything from budgeting and financing to finding the right home and making an offer. Subscribe for regular market updates, and leave a review to help us reach more people. Ready for an honest, informed home-buying experience? Viva la Unicorn Revolution - join us!
Blake and Jeremy went from managing shared co-living spaces to running 80 short-term rental properties.In this episode, they share the systems, deals, and mindset that made it possible.• How they pivoted from co-living to STRs• The growth path from a handful of units to 80• Systems they rely on to keep operations tight• The partnerships that accelerated their scale• Lessons learned about market selection and timing00:04:31 - Learning from a high-functioning real estate company00:05:52 - Landing a management gig through direct outreach00:08:04 - Managing a growing number of people00:10:15 - Staying focused while running STR operations00:14:42 - Biggest drags on a short-term rental business00:16:05 - What each founder values most in the business00:18:59 - Identifying problems and fixing them00:20:48 - Preventing issues from stacking up00:23:39 - Taking responsibility for team mistakes00:26:57 - Boutique hotel as a pivotal business asset00:28:39 - Balancing investment strategy with STR management00:34:36 - Staying at your own properties to evaluate quality00:37:18 - Challenges get easier with experienceGuest Bio:Blake Anthony Carter and Jeremy Courtney have both been operating in real estate and property management for over a decade. They initially got started in the co-living space, which led them to short-term rentals. They eventually sold our co-living business and with all-in on short-term rentals. Blake and Jeremy started a Facebook group and a meet-up group that allowed them to become known as the go-to guys for STRs in Austin. Their company is called Cribs. Blake and Jeremy now own a boutique hotel and three SF doors. They manage over 80 listings and have a real estate sales/consultant team.Guest Link:https://www.instagram.com/blake.anthony.carterhttps://www.instagram.com/thejeremycourtneyGet FREE Access to our Community and Weekly Trainings:http://group.strsecrets.com/
✅ FREE community: Join 33K+ hosts growing their wealth with STRs: https://www.facebook.com/groups/284886002732508/?mibextid=oMANbw✅ FREE tool and training to find your own Super Property: https://go.buildstrwealth.com/superpropertygrader
It's our 300th episode, and we're pulling back the curtain on 10 years of short-term rental success! From 50,000+ guests to managing properties in 3 countries, Tim reflects on the real journey—wins, losses, and the seven books that changed everything. If you're serious about STRs, this milestone episode is one you don't want to miss. ● The early days: managing STRs from across the hall to managing globally from afar ● Why falling in love with the problem is the real secret to scaling your business ● The 7 life-changing books that built the foundation of long-term STR success ● How STR management has gotten harder—and why that's actually good news for operators ● What's next: The vision behind building the largest virtual STR management company in the world This episode is a blueprint for sustained success in the evolving world of short-term rentals—perfect for both newbies and seasoned hosts. Check out our videos on YouTube: https://www.youtube.com/@ShortTermRentalRiches Grab your free management eBook: https://strriches.com/#tools-resources Looking to earn more with your property (without the headaches)? Chat with our expert management team: https://strriches.com/management-services/
This episode is a behind-the-scenes look at the latest STR WealthCon.From attracting 30 members to the mastermind to tactical takeaways from a 2000+ person event, we break it all down.• Why raw content works better than polished• The one onboarding question that reveals true goals• STR WealthCon recap: biggest takeaways• How to get ROI from live events• The vibe shift in the STR community-Want to get crystal clear on your goals and scale your STR business?Click the link below to book a discovery call and see if our Mastermind is the right fit for you.Link: https://go.strsecrets.com/podcast?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T023&utm_content=Clear-00:03:01 - Raw Content That Converts00:05:55 - Massive Takeaways From WealthCon00:08:42 - Unlock Event ROI Secrets00:11:32- Mindset Shift Every Host Needs00:14:25 - Behind the Scenes of a Power Launch00:16:54- High-Impact Networking Tips00:19:32- Underrated Gold From Live Events00:22:21 - Mastering the Referral Flywheel00:25:06- Growth Hacks for Ambitious HostsGet FREE Access to our Community and Weekly Trainings:https://group.strsecrets.com/
In this episode, I share why I went all in on short-term rentals and how this business changed my life — from leaving corporate finance at Hilton to building a lifestyle of freedom, growth, and purpose.I open up about how STRs helped me grow as a businessman, strengthen my relationship with my fiancée, support my parents, and ultimately design a life on my terms. I also talk real — the ups, the downs, and why this business isn't for everyone.If you're in this game and wondering whether to keep going — or thinking about getting started — this episode is for you.
In this Hosting Hotline episode, Sarah and Annette answer listener Dayne's two-part question about couch cushion covers and temperature control settings in short-term rentals. First, they discuss the pros and cons of using removable couch covers vs. investing in performance fabric for sofas. Then, they dive into the hot topic (pun intended) of thermostat control—should guests be allowed to set their own temperatures, or is it worth installing smart limitations to avoid outrageous utility bills? Sarah and Annette share real-life examples, hosting philosophies, and best practices to help you make decisions that balance guest comfort with operational efficiency.Resources Mentioned:Eco Mode / Smart Thermostats: Consider models like Nest or Ecobee for features like motion detection, scheduling, and remote access.Performance Fabric Sofas: Brands like Inside Weather, Burrow, and Article offer durable, easy-clean couches perfect for STRs.Hosting Hotline: Have a question for Sarah and Annette? Leave them a voicemail at hostinghotline.com to be featured in a future episode.
What separates a property that barely breaks even from one that dominates its market? It's not just timing, it's strategy.In this episode of the Cash Flow Positive podcast, Kenny Bedwell shares hard-earned insights from his latest experiences in the field and on stage at the STR Wealth Conference. Drawing from real client case studies, personal portfolio wins, and lessons learned from analyzing hundreds of STRs, Kenny emphasizes one core principle: if you want to stand out, you need to do what 95% of people won't, or can't do.Whether it's investing in an unconventional niche, buying undervalued properties with built-in equity, or avoiding oversaturated markets that everyone's rushing into, this episode offers a blueprint for smarter decision-making. Kenny doesn't just talk numbers, he dives deep into mindset, strategy, and the critical difference between copying a great idea and creating one.You will walk away with a sharper understanding of what makes an STR truly resilient and why now, more than ever, real estate investing requires bold moves and creative thinking. If you've been sitting on the sidelines or unsure where to focus your next property search, this episode will give you the urgency and clarity to act.If you've enjoyed this episode of the Cash Flow Positive podcast, be sure to leave a review and subscribe today! Listen now and enjoy!Key takeaways:Why you shouldn't wait until fall to start searching for STR propertiesThe 95% rule and how to apply it to your next investmentWhat it really means to have a moat and how to create oneHow to spot undervalued properties with instant equityWhy copying a good deal isn't the same as creating oneWhat investors are getting wrong in oversaturated marketsThe biggest mistake Kenny sees when hosts chase cash flow aloneHow to structure your next deal to survive any dip in revenueAnd much more...Resources:Connect with Kenny on LinkedInFollow Kenny on InstagramDisclaimer: The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of the Cash Flow Positive podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.
How much money do short-term rentals really make after five years? In this episode, Tim pulls back the curtain on one of his personal properties, revealing actual numbers - gross, net, and everything in between. As the STR landscape shifts nationwide, find out how rising supply and falling rates are impacting returns and what to do about it. • Discover supply surges in major STR markets • Hear the full breakdown of Tim's Memphis STR: gross income, cash flow, and true ROI • Learn why 2022 was an outlier year for many STRs and what's changed since • Get 5 proven ways real estate pays • Walk away with actionable backup plans for when income dips and expenses rise This episode is a rare, honest peek into real-world STR returns. Don't miss the tips that could protect your profits and maximize your property's long-term value. Check out our videos on YouTube: https://www.youtube.com/@ShortTermRentalRiches Grab your free management eBook: https://strriches.com/#tools-resources Looking to earn more with your property (without the headaches)? Chat with our expert management team: https://strriches.com/management-services/
Properties for Sale on the North Side? We want to buy them. Email: StraightUpChicagoInvestor@gmail.com Have a vacancy? We can place your next tenant and give you back 30-40 hours of your time. Learn more: GCRealtyInc.com/tenant-placement Has Property Mgmt become an opportunity cost for you? Let us lower your risk and give you your time back to grow. Learn more: GCRealtyinc.com ============= Sebastian Mysliwiec, founder of The Dream Rentals, explains how he's built a short-term and mid-term rental management company that delivers top guest experiences and maximizes profits! Sebastian talks about cutting his teeth and eventually thriving at a marketing company that helped build his real estate skill set. He provides tactical advice on underwriting, marketing, and managing short-term rentals (STRs). Sebastian explains how his team manages seasonality, shares a STR horror story, and top amenities for guests. He closes with remarks on refinancing considerations for STR properties and his team's growth strategy. If you enjoy today's episode, please leave us a review and share with someone who may also find value in this content! ============= Connect with Mark and Tom: StraightUpChicagoInvestor.com Email the Show: StraightUpChicagoInvestor@gmail.com Guests: Sebastian Mysliwiec, The Dream Rentals Link: The Dream Rentals Instagram Link: Skyscraper Tom's Instagram Link: The 12 Week Year (Book Recommendation) Guest Questions 01:58 Housing Provider Tip - Leverage Freedom of Information Act (FOIA) to request property info during due diligence! 04:25 Intro to our guest, Sebastian Mysliwiec! 08:31 Defining AirBnB arbitrage. 13:28 Underwriting basics of short-term rentals (STRs)! 20:10 Listing platforms for STRs. 26:09 Managing STR seasonality in Chicago to optimize profit. 35:36 STR Marketing Tips! 45:45 AirBnB Horror Story! 47:46 Top STR amenities. 49:23 Mid-Term Rental analysis and expanding to other markets! 55:13 Refinancing STR properties. 56:47 What is your competitive advantage? 57:15 One piece of advice for new investors. 57:42 What do you do for fun? 58:25. Good book, podcast, or self development activity that you would recommend? 58:54 Local Network Recommendation? 59:29 How can the listeners learn more about you and provide value to you? ----------------- Production House: Flint Stone Media Copyright of Straight Up Chicago Investor 2025.
What should you really ask before wiring $100K into a multifamily deal? In this special episode, Michael sits down with Nighthawk's Garrett Lynch and Drew Kniffin to run through 50 of the most important questions every passive investor should be asking—and every active investor should know how to answer.From deal structure and cash flow mechanics to team accountability, tax strategy, and risk mitigation, this is your behind-the-scenes guide to how Nighthawk operates—and how to evaluate any syndicator with clarity and confidence. Whether you're an LP looking to invest smarter or an aspiring operator trying to earn trust, this episode is required listening.Key Takeaways50 Questions Every Passive Investor Should Ask (And Every Active Investor Must Answer), including: Nighthawk's Track Record and Operating PhilosophyHow Nighthawk got started, how many deals they've done, and what makes their model differentWhat happens when a deal doesn't go to plan—and how the team respondsWho's on the core team and how key decisions are made (especially in tough markets)Why vertical integration and boots-on-the-ground operations give them an edgeUnderstanding Returns, Distributions & Deal StructureWhat kind of returns to expect—and how preferred vs. total returns actually workWhen investors get paid, what happens during a refinance, and how long deals are heldWhat happens if the property underperforms or market conditions shiftWhy Nighthawk doesn't do capital calls—and how they plan for uncertaintySyndications vs. Other Investment ModelsThe difference between syndications, REITs, and fundsWhat LPs actually own, how deals are structured legally, and what kind of control (or not) they haveHow profit splits and operator compensation align with investor outcomesMinimum investment amounts and what the onboarding process looks likeThe Passive Investing MindsetThe key mindset shift every new LP needs to makeMultifamily vs. flips, STRs, and self-storage—what makes multifamily the superior playHow to think about diversification across deals and sponsorsWhat to do if you're nervous—or your spouse isn't on board yetTaxes, Depreciation & IRAsHow multifamily syndications deliver major tax benefits (even on paper)What bonus depreciation is and how it offsets incomeWhen to expect your K-1 and how IRA investing works (including UBIT considerations)What happens tax-wise at refinance or sale—and how to defer gains via 1031sHow to Vet Deals and Sponsors Like a ProWhat to look for in underwriting: cap rates, expense ratios, rent growth assumptionsThe importance of fixed-rate debt, cash reserves, and risk-adjusted returnsHow to ask the right questions—even if you're not an expertWhy the best investors don't “return shop”—they evaluate the whole pictureConnect with Nighthawk EquityTake the Free Mini-Course at NighthawkEquity.comSchedule a Call & Join Our Investor ClubConnect with MichaelFacebookInstagramYouTube
